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“Your business brought in more revenue in the first six months of 2026 than your W-2 paid you all of last year.”

A few weeks ago, I was on a call with my accountant when he said this to me.

He was sharing his screen and walking me through the income statement, balance sheet, and cash flow statement for my business. They were the same three statements I used to pore over for other people’s businesses in finance and strategy, but now they were for something I was entirely responsible for starting and running.

I knew my business was doing well this year, after growing my Instagram following by 150K, landing deals with dream brands and starting to diversify my income streams.

But creator business money is lumpy and irregular, making it hard to see how the whole business is doing at an exact point in time. A partnership can be negotiated in one month, signed in another, published later, and paid months after that. Meanwhile, money is also coming in from Substack, coaching, product sales, TikTok, Meta, and several different payment systems.

I could find every number if I went looking for it, but I’d never seen all of them organized into one full picture, beyond just cash flow.

Seeing it in the three statements I’ve been used to seeing since my earliest days in business and finance felt surreal. I had started creating as a side project in October 2024; less than two years later, I was looking at the same three financial statements that “real companies” had, but with my own business’s name at the top.

I debated sharing any of this, and ultimately decided to because I wouldn’t be here if other entrepreneurs hadn’t shared how their businesses worked. Today I’m sharing the exactbreakdown of where my revenue comes from.

How my creator business makes money

A quick caveat on the numbers: These percentages represent revenue, not profit or take-home pay. The business also pays editors, assistants, contractors, software, professional fees, and taxes.

2%: Platform Payouts

Only 2% came directly from platforms like TikTok, Meta, and YouTube. TikTok pays for views through specialized reward programs; Meta pays (very little) for views and has lately been prioritizing carousel views. YouTube is my latest, smallest revenue stream.

This was expected, as I’m building a creator business, not an influencer channel. The difference is that I’m not optimizing for maximum views but rather the right mix of content that will attract and engage my target audience for both brand partnerships and my own offerings.

I use platforms for distribution. Most of my revenue comes from the business I’ve built from that distribution, but I always see these payouts as a nice bonus for work I’m doing anyway.

4%: One-Off Coaching and Office Hours

This came from calls with people who wanted my help with personal branding and founder-led marketing.

I didn’t actively promote coaching or try to fill my calendar. People reached out, and I took a small number of calls when I thought I could help. It’s still a small percentage of revenue, but these are the conversations that shape what I want to build next, which feels even more valuable than the current dollar amount in the long run.

5%: Digital Products

I have one paid digital product that helps professionals with nonlinear experience build a personal brand on LinkedIn through a 14-day guided sprint in Notion. I only started selling it a few months ago, so this represents a relatively new part of the business.

5%: Paid Substack

Another 5% came from the newsletter you’re reading right now! I also only started charging for it a few months ago, when I started publishing longer guides in which I package up weeks, months, or even years of work and experience building my business and personal brand.

I’m excited about this one because a paid newsletter lets me go much deeper than I can in a 60-second video. I’m investing more in the content here, more tactical guides, and more live engagement with paid subscribers moving forward.

This has also been a great reminder that sometimes the least strategic, but most joyful things you do end up being what you do best, and thus feeling like “easy money”! For me, that was and is Substack.

84%: Brand Partnerships

The remaining 84% came from brand partnerships across all of my platforms. That includes the content itself, paid usage when brands run my content as ads, exclusivity, and other contractual parts of a partnership that add to its value.

Brand partnerships are the biggest part of my business today and will continue to be an important source of revenue. I’m focusing more on longer-term partnerships with brands I love that not only fit my audience but also bring it real value, cross-platform campaigns that leverage the channels I’ve built across Instagram, LinkedIn, TikTok, and Substack, and new collaboration formats like community events and speaking, so this bucket feels less concentrated.

What I’m focused on next

I don’t want to create five random businesses. I want one focused umbrella or portfolio with multiple related income streams laddering up to it and compounding with each other.

• Brand partnerships: These will remain a core part of the business, with more emphasis on longer relationships and work across platforms.

• Substack: I’m putting more into the newsletter, including deeper guides and more live engagement for paid subscribers.

• Personal branding: I recently started working 1:1 with a few founders and experienced professionals on their personal brands and am building more ways to help ambitious people build personal brands around their expertise, particularly those with nonlinear life experiences. Fill this out if you want to get updates on this!

• Speaking: I have my first paid speaking engagements coming up in September, which is relatively new for me.

All of this feeds into the same body of work: helping ambitious people use what they know to build a name for themselves beyond corporate, create new opportunities, and make money from their expertise. My content, newsletter, coaching, partnerships, and speaking are all different ways of doing that same work.

5 things I’d tell anyone serious about building a 5-9 business

1. Get financial clarity early

I couldn’t have written this post a year ago. The money was technically there, but the information lived across contracts, payment confirmations, spreadsheets, invoices, and a running tally in my head.

You can’t make a good decision about what to grow, cut, or invest in when you can’t see what each part of the business earns and costs.

Relay helps me keep my business and personal finances separate and split money into different accounts for things like income, taxes, and contractor payments. I don’t look at one big balance and accidentally treat all of it as money I can spend.

Relay also makes contractor payments cleaner, and it has built-in bill pay and invoice management. The invoice tools would’ve been extremely useful when I was self-managed: I used to send brands some truly ugly DIY PDFs, then track whether they’d paid me in a spreadsheet (not my finest ex-banker moment). Relay also lets you give your accountant or team members their own access as more people become involved in the business.

Your first monthly finance review doesn’t need to be complicated. Look at four things: cash received, payments still outstanding, major costs, and money already set aside or committed. Then break revenue down by source. You’ll quickly see which part of the business is carrying everything else.

2. Build something that compounds with your 9-5

A creator business isn’t the right 5-9 business for everyone. If you haven’t started yet, the best place to begin is with the skills, customers, and problems you already know.

I worked in marketing during the day while building a content business outside work. My job made me better at positioning, storytelling, understanding brands, and selling partnerships. Building my own audience made me a better marketer because I had to test those skills on myself, in public, with immediate feedback.

Each side made the other better. Starting from something I already knew also meant I didn’t have to learn a new skill, industry, customer, business model, and distribution channel at the same time.

List what your job has already taught you: the problems you understand, the people you understand, and the work people already trust you to do. Build from one of those instead of starting from zero or forcing yourself into a business model that doesn’t align with your zone of genius.

3. Get clear on your positioning and customer

Whether your business is content, products, services, a community, or fractional work, your positioning and customer are two of the most important things to get right.

I know because I didn’t get this right until a year into my creator business. “I make career content” (where I started) is too broad to guide what you create or sell. A clearer version is: “I help ambitious professionals build nonlinear careers and turn what they know into a business.”

For a strategy consultant, “I help companies grow” could become: “I help early-stage B2B fintech companies turn complex products into clear go-to-market plans.”

The more specific versions tell you who the work is for, what they need, and why your experience makes you useful.

My creator business started growing again when I stopped thinking only about a niche and got much clearer on my audience and positioning.

Start mapping your positioning by writing this down: the person you serve, the urgent problem you help solve, and the part of your background that makes you the best choice. Use it to decide what to make, sell, and decline. I wrote the full breakdown here if you want to dive into this more.

4. Delegate earlier than feels comfortable

I hired my first editor around 6 months after I started creating content, well before the numbers felt big enough to justify it. Hiring early is a major reason the business eventually grew big enough to justify the cost.

The same was true with assistants. I didn’t hire them as a reward for growing; they gave me the capacity to grow while I still had a demanding job.

One of the best things about starting a business in your 5-9 is being able to put your W-2 income toward the business by investing in resources like editors and assistants.

Track every repeatable task you do for two weeks. Start with something frequent, teachable, and outside the work that needs your judgment. For me, that was editing and repeatable admin.

5. Accept that your free time is paying for the business

Building a business alongside a full-time job isn’t easy, and your time becomes a scarce resource.

For me, that meant working on weekends and vacations. I’m not as consistent with hobbies. As an introvert, creating content, going to events, networking, and taking calls also used a lot of the social battery I might’ve spent with friends and family. Not all the tradeoffs are bad, though: having less time has also reduced my online shopping habit!

Delegation and better processes give you some of that time back, but the beginning is still hard, especially when you’re building as a solopreneur alongside a full-time job. Decide what can receive less attention for a while, what stays protected, and revisit the tradeoff periodically to decide what’s worthwhile.

You got this!

If you’re building a business, I hope sharing my breakdown made the path feel more concrete. I posted my first video less than two years ago with no idea what it would become. It took a lot of nights, weekends, ugly invoices, and help from other people, and I’m still figuring out what comes next. But it’s possible, and I’m more energized than ever to help you build yours.

—

Thank you to Relay for sponsoring this newsletter and supporting the practical business content I want to make more of. If you’re building a business alongside your 9-5, you can sign up for Relay here.

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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Last week, I hosted a Q&A for paid subscribers on building a personal brand. We talked about:

• How to position yourself for brand deals

• How I personally make money from my personal brand

• Whether to choose one niche or talk about everything you’re interested in

• How to make a nonlinear or portfolio career feel cohesive

• Which platform to start with

• What content workflow to use when you’re starting

• How to research content ideas without scrolling all day

• How to build a personal brand while working in finance or another regulated industry

• How to post on LinkedIn without feeling “cringe”

Here’s the recap! Become a paid subscriber to join the next one and ask your own questions.

And sneak peak at the end…I’m sharing early details on a new way to get more hands-on help from me for building your personal brand.

Read more

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

Subscribe now

Today’s newsletter is a guest post from Sneha Rampalli, founder of Money Whispers, a community built around more honest conversations about women and money. Sneha left Google last year and now coaches women through career transitions. She also hosts Off the Table, a filmed dinner series about women’s real relationships with money.

I connected with Sneha through Substack a few months ago. Her work stood out to me because she tackles two questions that tend to pull in opposite directions during a career transition, and that a lot of us agonize over in our careers:

Will I find the next thing fulfilling? And will it financially support my life?

A lot of career advice tells you to follow your curiosity without mentioning your bank account; most financial advice tells you to protect your paycheck without asking what it might be costing you mentally and emotionally to stay.

So I asked Sneha to share how she approached both, together.

This is for anyone thinking about stepping off the linear path—whether you’re considering a startup offer with a lower salary and uncertain equity, a fractional or freelance career, a sabbatical, or any other move away from a predictable W-2. It won’t tell you whether to leave (only you can decide that), but it will give you three better questions to answer before you do.

A year ago, I left Google.

Every time I’ve picked up my phone in the last month, it feels like I have a new message asking me (I’m paraphrasing here): “How has your first year since quitting your job been, Sneha?”

Underneath that is usually another question: How did you know it was the right decision to leave?

The short answer is that I didn’t.

I left Google after five years, working on teams I had once dreamed of joining: Google Maps, Sidewalk Labs, and then Google Earth.

I still remember taking long walks around the Mountain View campus as an intern in 2018, daydreaming about what it would be like to work on the Geo for Good team. When I finally got there seven years later, I felt an amalgamation of emotions saying goodbye to the dream I once had.

Google had felt like the perfect combination: working on cool products, earning enough to be a financially independent woman, and being surrounded by some of the most intelligent people I’ve ever met, many of whom I feel lucky enough to call friends.

But making the decision to leave took three years of constant back and forth.

That is what makes golden handcuffs so effective. Your job doesn’t have to be terrible. It can give you interesting work, good people, excellent benefits, and a salary that makes leaving feel increasingly irrational.

One 26-year-old woman described the feeling to me this way recently:

“What is another promotion going to do? I get more money, it feels good for a day or two, and then the feeling fades. I get shuffled around to a new team to do work I don’t care about. But this is what pays for my life, and I’m not even sure what I want to do next. I just know I’m interested in autonomy and purpose.”

Maybe the next step for you is a startup with a lower base salary and equity you’re not sure how to value. Maybe you’re thinking about going fractional or freelance. Maybe you need a sabbatical after burning out. Or maybe you finally want to take a chance on working for yourself instead of someone else.

Whatever it is, working out the numbers can feel secondary to the bigger question: Can I actually trust myself to make this decision?

Everyone tells you to calculate your runway. But what about the opportunity cost of leaving your high-paying job? How does that runway actually sit with you? How do you decide what comes next?

Leaving your job is one of the few pivotal moments in life that is both deeply financial and deeply psychological. You can’t separate the calculations from your own relationship with money and financial ambiguity.

You can’t avoid the messy middle of figuring out what comes next. But you can go into it with better questions.

These are the three that helped me.

1. Are you making this decision from clarity or exhaustion?

Exhaustion and clarity can induce similar feelings but produce completely different outcomes.

Exhaustion can make you stay too long because you’re too tired to move. It can also make you leave impulsively because you’ve finally hit a wall.

That’s why I always say: before you touch your Excel spreadsheet, check what state you’re making the decision from.

If you took a real break, would you still want to leave? If your manager or team changed, would you feel differently? Are you moving toward something you want, or do you mostly need your current situation to stop?

As I’ve talked to people about leaving their jobs, I’ve noticed that many already know they need to calculate their runway. But it’s almost as if they need permission to take the next step.

The longer they delay the decision, the more they slowly lose their self-efficacy. They want to do something, but they aren’t acting on it.

You need to be bored first

People frequently think the antidote to exhaustion is optimism, but when you’re in that fog, anything optimistic can sound like toxic positivity.

The missing step between exhaustion and optimism is actually boredom.

I know “being bored” may sound oversimplified, maybe even a little insulting, especially if you’re someone who has time-blocked every 15min slot from Monday through Friday and you “don’t have time”. For someone wired to be hyperproductive, myself included, doing nothing on purpose is a discipline.

Your brain will reach for your phone before you’ve consciously decided to. That resistance is signaling how starved for idle time you actually are.

So I reiterate: go on a walk without headphones. Sit somewhere without your phone. Let your brain have space for emptiness.

I’m not saying you’re guaranteed to see a change within the first day, week, or even month, but diffuse thinking eventually allows you to gravitate toward what you want when you finally have the mental capacity to do so.

I’m a big believer that boredom reinstates creativity. Eventually, you feel restless. You want to do something. And guess what? Once your brain has that space, it feels a lot less daunting to ask questions about your bank account and credit card statements.

Before you make the decision, try writing down two lists:

• What am I trying to move away from?

• What am I trying to move toward?

If you have ten answers to the first question and none to the second, you may need recovery before you need a resignation letter.

2. What will it actually cost you to leave…and to stay?

Once you have enough capacity to look at the decision clearly, we can start talking numbers.

And I mean actual numbers, not a vague sense that you have “some savings” and a vague fear that it “won’t be enough.”

This is when you calculate what I call your Financial Oxygen Mask.

Your financial oxygen mask is the amount of time your savings can support you before earning income becomes urgent. It doesn’t tell you whether you should leave, but how long you can “breathe” while you figure out what comes next.

Calculating your Financial Oxygen Mask

Pull the last three months of bank and credit card statements from every account.

Add up everything: fixed expenses like rent, subscriptions, insurance, and loan payments, plus variable expenses like groceries, dining, transportation, therapy, and entertainment.

Average those three months. That number is what your life actually costs.

One month might contain an anomaly: a flight, a birthday dinner, or a car registration, so looking at three months allows you to see the pattern.

You can also calculate two versions:

• Your minimum baseline: what you need to cover your obligations and live acceptably.

• Your comfortable baseline: what it costs to maintain roughly your current lifestyle.

When I ran my numbers, I calculated that I needed $86,400 per year after taxes (or $7,200 per month) to live comfortably without adding anything to savings or investments. Here’s my real calculation:

How much of your savings is actually accessible?

Accessible means money you can get right now without a penalty: checking, savings, high-yield savings, and severance, if you have it.

Not your 401(k) or unvested equity. And not necessarily a taxable brokerage account you would rather not touch.

Technically, money in a taxable brokerage account (index funds, ETFs, or individual stocks) is accessible because you can sell it. But accessible and willing to access are two different things.

You might have $30,000 in index funds you’ve been building for years and decide you would rather extend your timeline or find income before touching them. That is a completely valid choice.

Be honest with yourself about which money you would actually draw from. Your real runway is built on money you would use, not money that technically exists.

Now divide

Financial oxygen mask = savings you are willing to use ÷ monthly baseline

That gives you the number of months you can support yourself before you absolutely have to make another move.

When I left Google, I ran this calculation and discovered that my runway was longer than my anxiety had been convincing me it was.

A few things may adjust your number (both up and down):

• COBRA health insurance can cost significantly more than what you paid through your employer’s plan.

• Pre-tax benefits and phone, transit, or gym stipends may disappear on your last day.

• Your commuting costs, work lunches, and wardrobe maintenance may also go down.

• If you’re starting a business, you may need to account for equipment, software, taxes, or other new expenses.

Run the numbers with those adjustments before making any decisions.

You can also model a few different realities:

• No income during the transition

• Some freelance or part-time income

• A few months without income, followed by a conservative income estimate

Your oxygen mask is not a guaranteed prediction but a way to understand your range of possible outcomes.

Here’s one way to interpret the number:

• Under three months: Income and health insurance are urgent decisions. Unless your circumstances require you to leave immediately, build a plan first.

• Three to six months: You have some breathing room, but start income conversations now.

• Six to twelve months: You have the runway to be intentional, especially if you set financial checkpoints.

• More than twelve months: You have time to be selective about what comes next.

These aren’t universal rules. Someone with severance, access to a partner’s insurance, family support, or a job that is affecting their health will make a different decision from someone without those resources.

Your runway number isn’t just a financial fact but a psychological one too.

If you have eight months of runway but are acting as if you have two weeks, something is driving that urgency that isn’t the actual number.

You need to know your baseline because you won’t know how to get to your destination if you don’t know where you’re starting.

If you have trouble looking at this alone, Accredited Financial Counselors are a great resource, especially if you want specialized help with debt or cash-flow management. Taylor Nelsen, AFC® and Bethel Habte, AFC® are two I recommend. (This is not an ad, just my own endorsement!)

Don’t forget the opportunity cost of leaving

There’s another number worth adding to the runway calculation that most people skip: opportunity cost.

Every month you aren’t contributing to your 401(k), you may miss your own contribution, your employer match, and the future compounding growth on both.

Under the Google terms that applied to me, the match was either 100% of contributions up to $3,000 or 50% of contributions up to the IRS elective-deferral limit, whichever was greater.

Two months before I left, I maxed out my contributions so I could capture the 2025 match before my final day.

Make sure you check the terms that apply to you in your benefits portal.

The same logic applies to unvested equity. If you have RSUs or stock options on a vesting schedule, leaving before your next cliff or vesting date can mean leaving a meaningful amount of money on the table.

Before setting your final day, answer:

• When is my next vesting date?

• Have I hit my cliff?

• How much equity would I be giving up?

• What is my post-termination exercise window if I have stock options?

• Is a bonus or employer contribution tied to a specific date?

A two-week difference in timing can mean a meaningful amount of money.

Then calculate the opportunity cost of staying

Opportunity cost runs in the opposite direction too. It may be harder to calculate, but it’s equally important to consider.

Every month you stay in a job you’ve outgrown, you are also making a financial choice. You are accepting the salary and benefits in exchange for delaying whatever you might otherwise build, learn, or pursue.

I want to give a moment to acknowledge that golden handcuffs make this especially difficult to internalize because the cost of leaving appears clearly on your Excel spreadsheet, but the cost of staying rarely does.

Sometimes staying changes the way you spend, too. Consumption fills the gap: the Sunday-scaries dinner out, the skincare haul, or the Euro-summer vacation you booked because you needed something to look forward to.

You may also begin underinvesting in yourself. You don’t join the rec soccer league, go on dates, meet new people, or build cool shit because you don’t have the energy to believe a different outcome is possible.

Staying may still be the right choice. But it should be a choice, rather than something that just happens to you because your paycheck made every alternative feel irresponsible or unimaginable.

3. What do you want your financial oxygen mask to make possible?

Now that you know your numbers, how do you make sure life doesn’t just happen to you?

You figure out what you value.

I used Brené Brown’s Dare to Lead values list to identify the values reflected in my life at the time and the ones I wanted to reflect a year later.

One year ago, my values were:

• Financial stability

• Compassion

• Self-discipline

• Gratitude

• Harmony

What I wanted one year later:

• Compassion

• Connection

• Learning

• Perseverance

• Integrity

Beyond compassion, I had a pretty big gap between the way I was living and what I wanted to be doing.

That was misalignment every damn day.

What was holding me back was the constant prioritization of financial stability. As someone who is vigilant about her money and took a LOT of pride in being financially responsible, I had to revisit my own money story.

The irony is that years of prioritizing financial stability were exactly what gave me the runway to ask these questions in the first place.

Letting go of that identity was scary, so I kept checking the facts against what my brain was telling me.

Life is expensive in New York. I checked my bank account weekly to compare the numbers with the emotions that came from no longer receiving a biweekly paycheck.

I also acknowledged the safety nets I had: a degree, a home that would take me in if I ever needed it, and confidence that I could find another job if I really needed one. Those resources shaped the risk I could take, and it would be dishonest not to include them.

I wasn’t trying to convince myself that nothing could go wrong. I wanted to train my brain to think beyond order and certainty, and to trust that I could make it through hard things.

Hence perseverance as the new value :)

If you’re a perfectionist who believes you need to do everything and be everywhere all at once, this will be a tough activity, but that’s exactly the point.

Narrow the list down to five words that reflect your life today vs. five you want to reflect your life a year from now.

Then ask:

• Where is the biggest gap?

• What is holding me inside that gap?

• What would living in closer alignment actually look like?

• What do I want my financial oxygen mask to give me the time to try?

The values are only useful if you translate them into action. If you choose connection, maybe that means two meaningful conversations each week. If you choose learning, maybe it means finishing a course or shipping a small project. If you choose autonomy, maybe it means controlling a specific part of your schedule.

Your runway gives you time and your values give that time a direction.

Reminder: your entire life is not this one life change

Once I completed the values exercise, the reframe that helped me let go of my financial-stability identity was realizing that this next decision didn’t have to determine my entire life.

I had been thinking about my career as one continuous spectrum, which made every decision feel permanent.

Instead, I started chunking my life into phases.

One phase can prioritize building, another can prioritize earning, and another might focus on connection, learning, caregiving, or stability.

Some call it a nonlinear career whereas I call it just life.

Leaving Google wasn’t about proving that I would never want or need a conventional job again but understanding what my body and mind needed before jumping ship for my next thing.

Sometimes, we look at our decisions with permanence, but I kept reminding myself that I wasn’t choosing the shape of my entire life. I was just choosing its next phase.

This decision is as much about money as it is about self-efficacy

I recently spoke with someone who told me:

“I’ve wanted to leave my job for a while, but I kept staying because there was always something on the horizon that made me think it would get better. Somehow, I’ve now been stuck in the same cycle for three years. I’m scared about the job market, especially because I want to try something new and don’t know how my skills transfer. I don’t have a strong gauge of my runway. I’m just so burnt out.”

I told her:

“When you continuously say you’re going to do something and then don’t do it, you stop trusting yourself. The inaction begins to take over like an insidious little monster.”

Her eyes bulged with relief.

“You are speaking my language,” she said. “That is exactly what I’m feeling.”

There’s something visceral and inescapable about losing trust in yourself.

The financial fear of leaving your job is huge. The psychological shift of no longer receiving a biweekly paycheck also takes time to get used to.

But what may be even more impactful than the lost paycheck is a hit to your self-efficacy: your belief in your ability to accomplish a particular task.

We think staying in a job we’ve outgrown is only emotionally expensive. But it can also become financially expensive in ways that will never appear on a spreadsheet.

You start believing this is your ceiling.

Right before I left Google, a mentor told me:

“It’s not about making the right decision. It’s about making a decision and making it the right one.”

We think trusting ourselves means predicting the future and knowing the outcome in advance. But we forget that humans have an uncanny ability to handle hard things.

We always have.

If you’re considering leaving, start here:

1. Give yourself enough space to distinguish exhaustion from clarity.

2. Calculate your financial oxygen mask.

3. Check the benefits, vesting dates, and other costs that could affect your exit.

4. Decide what you want your runway to make possible.

5. Set a date to make the decision (or revisit it if you decided you need more time).

Your financial oxygen mask tells you how long you can breathe, and your values give you a reason to use it.

Neither can eliminate uncertainty entirely, but together, they can help you make the decision from clarity instead of panic.

If any of this resonated, I write about the financial and emotional side of money through the lens of culture, career, and identity every week at Money Whispers.

Come find me there :)

With much love,
Sneha

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For the launch of Adobe Express’ AI Snapshot for Small Business study, I got to interview Daymond John, original Shark Tank investor and founder of FUBU. I’m excited to share our conversation with you today about how small businesses can use AI to grow without losing the “brand personality” that makes them unique.

Adobe Express surveyed 850 US small business owners and solopreneurs in June and found:

• Nearly two-thirds of respondents (64%) say AI helps their business compete but is also making it easier for brands to blend together.

• 56% agree that when everyone has access to the same tools, the competitive edge goes to whoever has the best taste.

• Most SMB owners (63%) second-guess their design and content decisions.

Small business owners are trying to use AI to move faster and compete without letting it flatten the taste and personality that make their brands recognizable.

Daymond founded FUBU “For Us By Us”, an apparel company deeply rooted in his community in Queens, turned it into a billion-dollar global fashion brand, then spent 17 seasons on Shark Tank evaluating founders.

Few people have spent more time thinking about what makes a resource-constrained but taste-forward business successful. I asked him how the Power of Broke changes when AI removes some of the constraints small businesses face, why community is still a moat, and where owners should start using AI in their workflow.

If you’re building a small business or brand, you’ll find something to take away from our conversation. I’ll also be diving into the Adobe Express study more this weekend, which I recommend checking out to see how businesses are using AI in marketing!

(Also…this interview is definitely going on the list of coolest things I’ve gotten to do because of my personal brand!)

AI gives a one-person business the resources of a team

Hannah: Adobe’s new study looks at how small businesses are using AI to build their brands. For an owner without a large creative or marketing team, where do you see AI providing the greatest advantage, and what becomes possible that wasn’t realistic before?

Daymond: AI is leveling the playing field for small businesses and isn’t going anywhere soon. Entrepreneurs have always had to figure out how to do more with less, and the biggest advantage of AI for small business owners is that it can help you show up as a much bigger operation.

Now you have technology that can give a one- or two-person business the resources that used to take an entire team. AI-powered tools like Adobe Express can help you bring an idea to life quickly while keeping your content on-brand and your vision authentic. What used to require more time and specialty skills can now be done in-house, so you can spend less time worrying about how to execute an idea and more time focused on growing your business. Sixty-six percent of small business owners already use AI for marketing.

How AI changes the “Power of Broke”

Hannah: Your Power of Broke philosophy is built on the idea that constraints can force entrepreneurs to become more focused and inventive. When AI gives a resource-constrained founder access to design, research, and marketing capabilities, how does the “power of broke” change? Does removing those constraints create more room for creativity, or can it remove some of the resourcefulness that gives an emerging business its edge?

Daymond: The Power of Broke has always been about being resourceful with what you have. I talk about OPM: other people’s money, mindset, mistakes, and manpower. Sometimes your biggest advantage is knowing how to tap into resources you don’t have yourself.

AI gives small business owners another tool to use to their advantage. The difference now is that a founder can turn an idea into a professional brand or marketing campaign without having a big team behind them. The technology is only as good as the person using it. The vision, hustle, and ability to understand your customer still have to feel true.

Fifty-six percent of small business owners agree the edge goes to whoever has the best taste. AI can help you move faster and remove some restraints, but it doesn’t change the Power of Broke. It can’t replace the clear point of view and hard work needed to make a business stand out.

Community is the small business advantage AI can’t copy

Hannah: In a recent interview, you said AI is “never going to have community.” Small businesses are often closer to their customers than large companies are. How can a small business turn that proximity into a brand advantage customers can see and feel?

Daymond: Small businesses still have to earn community by knowing their customers and making them feel like they matter. The voice behind a brand has to be real. That’s what we had with FUBU.

We weren’t trying to market to a community from the outside. We were already part of that community, and people connected with that because it felt authentic. When a customer sees their community reflected in your brand, that’s something a big company, or even AI, can’t easily replicate.

Why only 6% of small businesses publish AI content as-is

Hannah: AI is exceptionally good at recombining what already exists, which can produce content that looks polished but feels interchangeable. How can a founder use AI to find a distinctive angle instead of generating more versions of what everyone else is saying?

Daymond: Nearly half of small businesses heavily edited their most recent AI-assisted content before publishing, and only 6% published it as-is. AI can give you a great starting point, but your brand and how well you know your customer is what makes it yours.

That’s where a tool like Adobe Express can help. You can use AI to quickly generate a design based on what you need, then apply your Brand Kit, including your fonts, colors, logos, and other visual elements, to make it feel consistent with your brand. You get a starting point and still have room to make the design recognizable. It gives you the speed of AI without losing what makes people recognize your brand.

The $50 billion pitch that raises an immediate red flag

Hannah: As Shark Tank enters its eighteenth season, founders can use AI to create a polished pitch deck, write persuasive copy, and anticipate many of the questions they will be asked before entering the Tank. What tells you that a founder has genuine customer insight and original judgment?

Daymond: We invest in people. One of the biggest red flags is when somebody tells me, “This is a $50 billion industry, so if I just get 1%, look how big the business can be.” That doesn’t tell me you know the business.

I want to know your numbers, who your customer is, what they’re willing to pay, what it costs you to acquire them, and whether you’ve proven that people want what you’re selling. Founders need to know the ins and outs of their business and be able to manage tough questions from the Sharks. AI can help you build a better deck and prepare, but once we start digging in, you still have to know the answers.

Content at scale can’t manufacture authority

Hannah: You’ve said attention is the new currency. AI now makes it possible to manufacture an enormous amount of visibility. What separates real authority from a founder who is producing content at scale using AI?

Daymond: If you’re invisible, you’re vulnerable, and if you’re vulnerable, you’re replaceable. You can mass-produce content all you want, but that won’t be enough to manufacture credibility that drives people to keep coming back for more.

The founders with real authority are confident in showing people how they think, what they’ve built, and what they stand for. Only 37% of small business owners trust their instincts completely to move forward without hesitation, which shows us there may be a confidence crisis. You need to stay true to yourself while putting yourself out there with valuable things to say, and the right consumers will find you.

How Daymond would build FUBU with local ambassadors and AI

Hannah: If you were launching FUBU for the first time today, which parts of building and marketing the brand would you use AI for, and which parts would you still insist on doing personally or directly with the community?

Daymond: If I were relaunching FUBU for the first time today, I’d use AI to help me move faster. I probably wouldn’t build it around traditional retail. I’d have ambassadors in communities across the country. AI could help those people create content for their local audience and tell the FUBU story at a scale we never could have when we started.

The things that made FUBU what it is, the product, the point of view, and the voice of the brand, came from me and my partners and our connection to the culture we were building for. That’s something I wouldn’t hand over to AI. FUBU was born from our own experiences and from understanding what our community wanted because we were part of that community ourselves. AI can help you execute on a vision faster, but the vision still has to come from somewhere real.

The first step in a small business AI audit

Hannah: If a small business owner worries they’re falling behind on AI and wants to audit their workflow, what should they look at first?

Daymond: Make a list of the repetitive tasks in your week. Where are you spending the most time? Finance tasks? Creative and design materials? Admin?

Identify where AI can save you time without compromising the quality or personality of your brand. Start with one or two initial use cases, measure how much time you’re saving, and build from there. The goal is to spend less time working in the business and free yourself up to spend more time on the parts of the business that only you can do.

Read the full Adobe Express AI Snapshot for Small Business study, and learn more about Daymond at daymondjohn.com.

✋ NexusPoint — Not a tool, but this is the best resource I’ve used so far for hiring assistants and editors overseas (and I’ve tried a LOT) - they take care of everything up to the point of hiring and don’t charge until you onboard someone → Book a free discovery call

💬 ManyChat — The tool behind every “comment X and I’ll DM you the link.” It auto-sends resources to everyone who comments, so I’m not manually replying to hundreds of DMs → Try ManyChat

💬 Stanley — If you’ve been wanting to post more consistently on LinkedIn, this is the writing partner I use. You’ll get a 3-day free trial with my link → Try Stanley

🎙️ Wispr Flow — Voice-to-text that actually works. I dictate messages, prompts, and emails instead of typing, and it saves me hours every week talking to AI → Try Wispr Flow

👩🏻‍💻 Fiverr — My go-to for hiring freelancers for things like design, editing, one-off projects (I use Fiverr Pro to save time on vetting talent) → Try Fiverr

🧊 Othership — The sauna/cold plunge I go to! → Try Othership with my discount

🧾 Xero — The accounting software running the back end of my business. Bookkeeping and invoices without me having to think about it → Try Xero

Subscribe now

Last week, an old friend told me she thinks I care more about money than people.

We were on a trip with two other friends, all of whom I met over a decade ago.

A few days before that, I had been in San Francisco filming a paid video with OpenAI.

When I mentioned the trip, the conversation quickly became about everything wrong with AI.

In New York, I spend most of my time around people in tech, startups, and the creator economy, where the default question is usually how to use AI, not whether using it at all says something troubling about your values.

That conversation made me realize how long it had been since I’d had a conversation about AI with people who weren’t already using it every day.

AI is deeply embedded in how I work and manage my personal life. When that’s your everyday reality, it can be difficult to pause long enough to understand why someone else’s first reaction is fear rather than possibility.

But my friend’s criticism wasn’t only about OpenAI.

She told me that over the past year, as my work became more public and my content focused increasingly on building businesses, making money, AI, and creating content, she had started to believe that I cared more about those things than about people and social issues—the topics we used to discuss all the time in college. She also questioned whether companies she considered morally corrupt were paying me to promote their views.

I don’t think most of my underlying beliefs have changed in the past few years. But what I talk about, work on, and reward with my attention clearly has.

She didn’t see a full picture of me. But her comment, in the context of the Open AI brand trip controversy, did make me ask whether my ambition has changed what I pay attention to, whose concerns I value, and how I justify the work I choose.

If you work in finance, consulting, tech, or startups, or you’re building a business of your own, you may have asked yourself some version of the same question. These worlds reward ambition, growth, and financial success. They also often require us to make compromises and become very good at explaining why our choices are worthwhile or simply not caring.

But how do you know when you’re making a reasonable compromise vs. when the pursuit of success is changing what you value?

Does caring about building a business and making money make you more likely to compromise your values along the way?

If you’ve read past issues of my newsletter, you’ll know that this is very different from my regular content (which looks like this or this!), but this topic was on my mind the entire week, and in the news, so I wanted to both share my thoughts and ask for yours.

How my career became “more moral”

My friend’s comment surprised me because I had been telling myself the opposite story this whole time: that my career had become more “moral” over time.

My first job after college was in banking at Morgan Stanley, one of those industries most people have no problem calling evil.

I worked on real estate financing deals with large Asian developers. Some of the companies we worked with faced allegations ranging from accounting irregularities to serious personal misconduct. Even though my individual role was just building models and presentation decks, it didn’t feel entirely separate from the institutions and people the work supported.

Then I left banking to join a ride hailing and food delivery company.

That felt like progress.

I could see the people using what we built. Drivers who needed flexible work could earn money. Small restaurants could reach customers they never would have reached on their own. Unlike moving numbers around in a financial model, I could watch an order happen in real time and feel good about sending a payment to Driver #15828.

Since then, I’ve moved into startups, marketing, and the creator economy. I can tell myself that I have become increasingly “ethical” with every career move: further from banking, closer to entrepreneurship, education, and helping people build things for themselves.

Over time, it felt like my work had become more useful, more personal, and easier to connect to people’s lives.

Is it “moral,” or is it storytelling?

But at every stage of my career, there were always two stories: one about the value we created and another about who might be paying the price.

In banking, the good story was that we helped companies raise capital, build housing, and grow. The less flattering story was that we helped already powerful companies and executives become richer at the expense of communities and environments.

At the food-delivery company, the good story was that drivers could access flexible work and small restaurants could reach new customers. The bad one was that gig platforms could shift risk onto drivers, provide little stability or protection, and charge restaurants fees they could barely afford.

Both stories were true, and all ambitious industries have their own versions.

Consultants help leaders solve difficult problems, but their work can also legitimize decisions that harm employees and communities. Creators educate their audiences, but they can also spread false information and make disingenuous sales. AI can help more people learn, build, and earn money while disrupting livelihoods, consuming natural resources, and concentrating power.

Most of us are trying to reconcile the opportunities available to us, the skills we have, the money we want, the people we need to support, and the beliefs we hold. Those things rarely form one perfectly consistent package, and we naturally emphasize the version that makes our work feel better.

Maybe my career did become more moral. Or maybe I just got better at telling the version of the story that made my choices feel moral.

Why AI is the latest catalyst for moral judgment

Lately, AI has made these questions much less abstract for me.

Last week, while I was in San Francisco filming a sponsored video for OpenAI, an OpenAI brand trip taking place the same week “ChatGPT Summer Camp”, was drawing intense backlash across social media.

Even though I wasn’t on that trip, I still appeared in someone’s TikTok criticizing creators who take money from OpenAI. I know creators who actually attended the trip that have received death threats.

The TikTok wasn’t really about me, the other creators, or even about one brand trip, but about what taking money from an AI company has come to represent.

AI has become a proxy for several moral debates happening at once: what happens to people’s jobs, who owns creative work, how much energy and water data centers consume, what happens to the communities where they are built, and how much power we want a small number of companies to hold.

For people who use AI every day, its benefits feel like superpowers. It helps them learn, build businesses, work more efficiently, and do things that previously required more time, money, or people.

For people who experience AI primarily as a threat to their work, environment, or community, the risks are tangible. The promised benefits can sound like sleazy marketing from the same companies creating the disruption. And it’s easy to blame the creators who act as the messengers.

AI is not the first technology to create this conflict.

Social media has enabled millions of people to find communities, build audiences, and run businesses. It has also contributed to cyberbullying, unhealthy comparison, and an attention economy that can be particularly harmful to young people.

Amazon has made products more accessible, created new income for sellers, and made it easier for small businesses to reach customers. It has also faced criticism over its labor practices, environmental impact, and effect on local retailers.

The same technology can create opportunity for one group while imposing costs on another. The people who benefit most directly are often far away from the people experiencing the greatest harm.

AI feels somewhat distinct because of how quickly it is moving and how many parts of our lives it touches at once. But in the end it’s just the latest version of a question we’ve faced before:

How do you engage with a technology that creates real value without ignoring the harm it may also create?

If every choice is morally compromised, how do you decide?

There are companies and industries I won’t work with as a creator. Gambling and prediction markets are among them.

But Substack, the platform I use to send this newsletter, supports native Polymarket embeds.

Does indirect participation make us hypocrites? Where does using a platform end and endorsing it begin? How much responsibility do we have for every institution that touches the work we do?

I don’t have a clean answer, but there are a few easy positions available.

One is the purity test: any association with a company that causes harm makes you morally compromised.

Another is deciding that because every company is problematic, we can justify working with anyone as long as the check is big enough.

A third is exaggerating the moral distance between competitors that share many of the same incentives and practices, then designating one as “evil” so choosing another feels ethically clean. (e.g. OpenAI becoming AI’s default villain, while its competitors are treated as categorically more virtuous)

All of these feel insufficient.

Moral ambition does not require a perfect institution

Of course, I can’t write about ambition and morality without mentioning Rutger Bregman. In his book Moral Ambition, he argues that ambition itself is not the problem, that impact depends on what we direct it toward. He believes ambitious people should direct more of their energy toward work that benefits society, such as using policy, entrepreneurship and institution-building to solve large problems like climate change or global health.

In college, I was probably one of the strongest believers in this argument.

I studied political science, participated in activism, and imagined a career in government or diplomacy. I took a nonprofit and city council internship because I wanted my career to contribute directly to causes I cared about.

Then I experienced the practical limitations of that path.

These jobs weren’t going to pay me a livable wage. They also didn’t provide the mentorship, training, or pace of learning I wanted at the beginning of my career. I wanted to be surrounded by ambitious people who would challenge me and help me grow quickly.

Advice to pursue more morally ambitious work can overlook what prestigious but morally questionable jobs provide for immigrants, first-generation professionals, and people without an established safety net. Banking gave me training, financial security, credibility, and opportunities I might not have accessed otherwise. (I don’t regret choosing it, and I still advise students in a similar position to seriously consider the opportunity.)

My nonprofit experience also complicated the idea that moral ambition can be judged by the institution on your résumé.

Part of my internship involved applying for grants from major banks, the same institutions often criticized for attracting talented people away from more socially beneficial careers. The nonprofit was doing work I considered morally ambitious, but it depended on funding from institutions whose broader impact was morally contested.

So what happens when morally ambitious work is funded by, housed inside, or otherwise dependent on an imperfect institution?

Sometimes this work happens within the company itself. Anthropic recently committed $150 million to Claude Corps, a program that will train 1,000 early-career fellows and pay them to help nonprofits use AI. OpenAI has funded the American Journalism Project’s Product & AI Studio, which helps local newsrooms use AI for work like translating coverage, analyzing civic information, communicating with donors, and reaching new audiences.

I think those examples count as morally ambitious work, directing money, talent, and technology toward organizations that serve the public.

That said, they don’t prove that Anthropic or OpenAI are “good” companies. Funding valuable work doesn’t resolve concerns about jobs, copyright, data centers, or safety. But those concerns don’t make the work happening inside nonprofits and local newsrooms meaningless either.

The danger on one side is treating one beneficial program a get out of jail free card for the entire company. The danger on the other is deciding that no valuable work can come from money, people, or institutions connected to something we believe is harmful.

Maybe moral ambition is not only about choosing the perfect employer or donor. It can also be about what we do with the money, skills, and influence available inside imperfect systems.

What rules do you use when there’s no perfect moral compass?

Every week, I send my management team messages like these in response to inbound partnerships from brands:

My current rules are something like:

• I don’t promote tobacco, gambling, prediction markets, or predatory consumer products that directly profit from addiction, deception, or financial vulnerability.

• I don’t make claims about a product that I don’t believe are true.

• I try to understand how a product makes money, who benefits from it, and who bears risks I may not experience.

• I don’t cheat or copy other people’s work, and I cite the people and research my ideas come from.

• I correct factual errors and omissions, and reconsider endorsements when new information changes my view.

• I try to disagree without publicly humiliating or attacking people.

These are not proof that I have solved morality or am more moral than another creator or entrepreneur. In fact, many might look at this and think my list is far too short.

And there will always be two stories for every decision:

Recently, I passed on an opportunity to advise and invest in a marketplace where people could trade on the future value of human talent because I wasn’t comfortable with the idea of turning people’s future careers into a speculative asset. But someone else might make a strong argument for why that product creates opportunity for those underserved by traditional capital raising.

I’ve certainly made mistakes in the past and taken money that I later regretted because I didn’t do sufficient due diligence.

Some rules are easy to follow because the answer is obvious to me. The more difficult decisions are the ones involving products that create real value and real harm at the same time, which describes most large companies and technologies today.

The questions I ask before I take the money now

I’m still figuring this out, but these are the questions I want to keep asking:

1. Is it strongly aligned with my mission of empowering smart people with nonlinear paths to build careers and businesses that make them rich and happy? Or do I have to make too many jumps to justify the connection?

2. Would I still make this claim if nobody were paying me, and what might I be incentivized not to notice?

3. Who benefits from this decision, and who bears costs I may not personally experience?

4. Could I explain my decision plainly to an informed person who disagrees with me and fully believe my own justification?

5. What evidence would make me change my mind?

Ambition makes your values more consequential

I don’t think my friend was right that I care more about money than people. (She’s a former friend now, in case you’re nosy and wondering 🍵)

She was responding to the version of me she sees through my work online, where I talk much more about building businesses, making money, and using AI than I do about politics or social issues. That version is not all of me, but it is still a version I chose to put into the world.

I’m glad we had the conversation. Someone can misunderstand you and still point to something worth examining.

That examination has not led me to stop working with AI companies.

I believe AI will be one of the defining technologies of our generation. I have concerns about its impact, but I’m also in a unique position to work with and advise some of the companies shaping it, where I’ve met some of the smartest, most curious, and most creative people I know.

These partnerships also create opportunities for me to grow my business and brand, and I won’t disguise self-interest as pure altruism.

And the last thing I want this essay to do is scare anyone away from building a business or talking honestly about money.

I believe more people with strong values should make money, build businesses, accumulate influence, and put their ideas into the world. Money creates security, freedom, jobs, and the ability to support the people and causes you care about.

Leaving all of that to people with fewer scruples would not make the world more moral.

Ambition does not inherently make someone a good or bad person. It makes their values more consequential.

The more money, influence, and visibility we accumulate, the more important it becomes to know what we believe, understand why we believe it, and be honest about what we are—and are not—willing to trade for success.

I still don’t have a neat answer, so part of writing this is to ask for yours:

How do you decide which compromises you can live with, and where do you draw the line?

A high-growth health-tech startup is looking for an exceptional senior content and brand operator to work closely with the founder to shape their long-term positioning and point of view, develop original ideas and narratives, and build a world-class content and media engine around them. This is a confidential search - fill out this form if you’re interested for more details

📣 Get your 5-9 Creator Starter Kit

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✋ NexusPoint — Not a tool, but this is the best resource I’ve used so far for hiring assistants and editors overseas (and I’ve tried a LOT) - they take care of everything up to the point of hiring and don’t charge until you onboard someone → Book a free discovery call

💬 ManyChat — The tool behind every “comment X and I’ll DM you the link.” It auto-sends resources to everyone who comments, so I’m not manually replying to hundreds of DMs → Try ManyChat

💬 Stanley — If you’ve been wanting to post more consistently on LinkedIn, this is the writing partner I use. You’ll get a 3-day free trial with my link → Try Stanley

🎙️ Wispr Flow — Voice-to-text that actually works. I dictate messages, prompts, and emails instead of typing, and it saves me hours every week talking to AI → Try Wispr Flow

👩🏻‍💻 Fiverr — My go-to for hiring freelancers for things like design, editing, one-off projects (I use Fiverr Pro to save time on vetting talent) → Try Fiverr

🧊 Othership — The sauna/cold plunge I go to! → Try Othership with my discount

🧾 Xero — The accounting software running the back end of my business. Bookkeeping and invoices without me having to think about it → Try Xero

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I’ve always wondered how some people always seem to find the newest thing first. They’re buying Bitcoin in 2015, building with AI in 2022, joining a unicorn when it’s a 12-person startup no one’s eve heard of.

Sarina Virk Torrendell is one of the early ones, several times over. She was employee #12 at Postmates, launching its first markets before Uber Eats and DoorDash were household names and you still had to explain what on-demand delivery was. Then she worked in payments at Apple before everyone paid by tapping, then live shopping at Amazon. Now she’s building YouPop for “multi-hyphenate knowledge creators,” who she believes are the next big wave of the creator economy.

Sarina’s career, as she describes it, is “both linear and nonlinear”: human rights advocacy in DC, a master’s at Columbia, that 12-person startup, her own e-commerce company, then Apple, Meta, and Amazon. The whole time she was also career coaching, podcasting, teaching marketing at Reforge, and advising startups. She was a multi-hyphenate for a decade before she started building for them.

I’ve been learning a lot from Sarina’s career and entrepreneurship journey since I first met her a few months ago, so I wanted to share our conversation with you on:

• How she spots a new category early, and what she saw that made her quit Amazon to build in the creator economy

• Why your professional experience is an advantage in the creator economy

• Which skills matter more, not less, as AI changes how we work

• How to start sharing what you know before you feel like a “creator”

• How ambition and risk change as you grow your career and family

Whether you’re trying to break into tech, building something on the side, or sitting on expertise you haven’t shared yet, I think you’ll find something valuable from our conversation.

From international affairs to employee #12 at Postmates

Hannah: You’ve said your career is both linear and nonlinear. For someone who doesn’t know you, give us the short version of your path.

Sarina: I love this question, because whenever people hear my background they assume I’ve done a variety of different things, which I have: everything from marketing to operations to business development to product. But everything layered on top of what came before. There was always growth and compounding in the traditional linear sense.

Early in my career I was in international development, working on human rights advocacy campaigns globally. After college I went to DC and worked for a nonprofit and a think tank, and I really believed that was how I wanted my career to evolve, and I wanted to maybe start my own organization one day. So I went to graduate school for international affairs at Columbia.

Hannah: How did your career goals change while you were at Columbia?

Sarina: I started to notice some interesting things happening in Silicon Valley. For context, I’m a Bay Area native turned New Yorker. I’ve been in New York about 16 years now, but technology and what was happening in the Bay was always natural for me to keep an eye on.

This was 2010. The App Store had launched. Companies like Uber and Airbnb were starting to pop up. And I thought to myself, this is a really interesting moment in technology, and I’m curious what this is all about. Even though I was getting a master of international affairs at the time, I took a business school class one semester, and it was there that I thought, I think this might be more my jam.

How she broke into tech without a network

Hannah: You didn’t have a traditional tech background or an existing network. How did you approach breaking in?

Sarina: I was applying to 50 or 60 roles a week, meeting five to ten people for coffee, offering to do free projects, and spending hours learning about the industry. I grew up in the Bay Area, but that didn’t mean I knew people in tech or had a way in. I had to build those relationships from scratch.

I was paying close attention to what was happening with marketplaces and the App Store, and I knew I wanted to be part of it. Eventually I had a few offers, and Postmates was one of them.

Hannah: Of all the companies you were applying to, what made Postmates stand out?

Sarina: They were the first on-demand delivery company, and their whole thing was: how can we build a remote control for consumers to get anything they want, while creating more income for local merchants and people looking for flexible work?

Coming from advocacy and international development, I saw it as an interesting new model for growing a market. So I joined as employee number 12. My job was to launch Postmates from the ground up in its first markets and build the playbook that later helped it scale nationally.

Hannah: How did you evaluate an opportunity that early when you had no startup experience?

Sarina: I was 25, and some of my confidence came from not knowing enough to overthink it. I wasn’t evaluating Postmates based on its funding stage. I was looking at what was happening with marketplaces and on-demand services, and I saw an opportunity to help build a new category.

I remember Bastian Lehmann, the founder, telling me in the interview that they had just raised a seed round. I didn’t even know what that meant. I didn’t understand how risky the company was, but I also didn’t understand how big the opportunity could become. At that age, the naivete was an advantage.

From Postmates to a decade in tech

Postmates was only the beginning of Sarina’s career in tech. After her first stint there, she started an e-commerce handbag company and ran growth operations at Glamsquad. She later returned to Postmates to lead retail partnerships with companies including Glossier and Warby Parker, then launched its alcohol and grocery categories.

From there she moved into global partnership marketing at Apple, product marketing at Meta, and creator partnerships for live shopping at Amazon. Alongside those roles, she was career coaching through withSarina, hosting the Career Memos podcast, teaching product marketing at Reforge, and advising startups. By the time she started YouPop, she had already spent years combining a corporate career with several other kinds of work.

What she’s building at YouPop

Hannah: How did you get the initial idea for YouPop?

Sarina: I started to chat with content creators I knew in this space and asked about their pain points. The biggest one was that they were using too many tools that didn’t really serve them, and the analytics were terrible.

That gave me the idea to create true AI-native infrastructure for the modern-day, multi-hyphenate, knowledge-first creator. I wanted to create a new agentic operating system for that person.

Hannah: When you say “multi-hyphenate knowledge creator,” who do you mean?

Sarina: It’s a creator like you. You have a 9-5, but you also have content, from short-form videos to a Substack. Maybe you’re going to write a book, maybe you have a podcast, maybe you’re going to sell a digital course or start a community. You’re not just doing brand deals.

Hannah: What will creators be able to do with YouPop that they can’t do now?

Sarina: We’re not public yet, so I’ll keep this high level. Fundamentally we’re equipping creators with the data and insights they need to make real business decisions. The goal is more discoverability and more monetization opportunities, all within an intuitive, agentic operating system.

Coming from consumer technology, I know what good looks like and I know what bad looks like, so we really wanted to focus on UX. Whether you’re a very data-driven creator or not, you have a way to get intelligent insights to inform how you want to grow your business, because you are a business owner at the end of the day.

Why expert creators have an unfair advantage

Hannah: What do you think the current creator economy gets wrong about the “multi-hyphenate” or knowledge creator?

Sarina: There’s so much focus on brand deals in the industry, and certainly that’s a great way to monetize. But there’s so much opportunity beyond that.

To give you an example, one of the content creators who sits on the advisory board for YouPop has a huge following on TikTok and Instagram. But she monetizes primarily through keynote speaking events and corporate workshops, not brand deals.

A lot of these multi-hyphenate creators have an unfair advantage because they have deep expertise. As they share that knowledge, it can lead to corporate workshops, keynote speaking, podcast opportunities. The creator economy for a long time was affiliate and brand deals. Now there are so many other ways to monetize, both offline and online.

Hannah: So the expertise itself is the asset, and the content is how people find out about it.

Sarina: Even for you, Hannah. I remember you telling me you got your current role because you’ve been sharing your perspective online. The monetization is coming from somewhere other than the content itself. You’re sharing your expertise and people are watching, even if they’re not engaging with your content. They see it, and then they think of you. If a company says, I want someone to come lead a workshop on marketing or building a Substack, they’re going to think of you, because you’re visible.

Founder-led marketing over building in public

Hannah: You’re posting a lot right now. How does that fit into your marketing strategy overall?

Sarina: It’s definitely founder-led marketing. I wouldn’t say it’s building in public, because I’m pretty tight-lipped about what we’re building as the product is still in beta. I focus more on sharing my own knowledge, because I’m building for knowledge creators and I want to model what that means, from sharing my fundraising tips to what I’ve learned about go-to-market throughout my career.

And it’s been amazing, because it goes back to opportunities that come your way. I’ve connected with so many creators just because I’m being visible.

Hannah: Why do you think that kind of relationship-driven marketing works right now?

Sarina: Paid marketing was efficient for a long time, but I don’t think it’s as efficient now. Consumers are inundated with products and tools. Even creators have so many platforms competing for their attention.

That makes community-driven marketing and one-on-one relationship-building more important. Showing up online and building direct relationships might sound old school, but I think it’s becoming effective again.

The AI tools she uses as a solo founder

Hannah: You’re a solo founder building an AI product. Where do you use AI the most as a teammate?

Sarina: I use Claude, for my more analytical thinking, and then ChatGPT for a lot of marketing, decks, and storytelling because it knows so much about me and how I think because I’ve used it so much.

In terms of other tools, my current accounting software is Finta and I’m obsessed with it. It’s AI-native and it’s so great for any startup founder. My tech stack isn’t super extensive, but I rely quite heavily on Claude and ChatGPT.

How her approach to risk changed over time

Hannah: You described joining Postmates as taking a “naive risk” at the time. How did taking the risk of leaving Amazon to start YouPop feel in comparison?

Sarina: Now I’m 40, I’m a mom of three, I own a home, and I live in an expensive city. My risk appetite has naturally shifted as I’ve taken on more responsibility. I went from naive risk-taking to calculated risk-taking.

I left Amazon just after finding out I was pregnant. At that point I had an extensive career, so I was walking away from a lot of stock and a very comfortable position.

Hannah: What made it feel like a calculated risk?

Sarina: I looked at the market, the categories, and the network I had built. The market was signaling a lot of opportunity for AI-native companies, especially vertical AI. The creator economy was growing, and this segment in particular was growing. And after more than a decade in tech, I had strong relationships I could draw on. There was still a lot of risk, but my career had also created opportunities and connections I didn’t have at 25.

The skills that mattered before AI, and the ones that matter now

Hannah: What are the most valuable skills from your career that you use now as a founder?

Sarina: If you had asked me this two years ago I would have said financial modeling, data and analytics, being able to show things through data. Now I just go into Claude, prompt it, and it builds all my financial models for me.

So now I think it’s really storytelling and relationship building. The ability to tell a good story is something I learned at Apple, because at Apple you were only allowed to use keynotes in meetings. There were no memos. Everything is in a keynote, and it doesn’t matter if it’s a small meeting. That ability to tell a story and present it is something AI can’t replicate. It can help you frame things, but the human storytelling skill has helped me tremendously as a founder.

Hannah: You just raised a pre-seed. How did your storytelling skills help?

Sarina: It was critical in every step, even in just putting the pitch deck together. A lot of people have asked me what and who I used to help me put together the story and the narrative, but it was just me. I came up with the story and the narrative, and I chatted with a very good friend of mine to brainstorm, but my approach to putting together that deck felt “old school”.

Relationship building over a decade in tech also helped a ton. It was a very tight process. I didn’t take a million meetings. I probably had 20, and every single one was a warm intro.

Hannah: The data fluency still matters though. You learned how to read financials and turn them into a story, which are skills that are valuable even if you’re not building the models yourself.

Sarina: A hundred percent. You need the data to tell the story, because you can’t just tell a story and not have any evidence. Even though YouPop is pre-launch and pre-revenue, you can still forecast things. You can still use benchmarks and other things from the market to help you use data to tell a story. But that only comes from a decade-long career of knowing how to do that and then tell the story to investors and the broader market.

How to start when you have the expertise but no public visibility

Hannah: What’s your advice for someone with years of experience in, say, marketing or product who is curious about sharing their expertise. What makes a successful expert creator?

Sarina: Show up and be yourself. I know everyone says this but it’s absolutely true. I started sharing more of my own knowledge because I’m building for this audience, and wanted to show how to do it myself. My posts that have performed the best were me sitting on my couch talking about go-to-market as if I were talking to you. Not super polished, just me sharing my insights.

There are so many people who have valuable experience, and it doesn’t have to be a heavy lift. You can literally open up your Instagram app, record a Reel, and share your knowledge. The main thing is to be true to yourself and true to your expertise, and not try to be something you’re not.

And get over the cringe. That’s the biggest thing.

Building a company with three kids under five

Hannah: A lot of women I hear from, myself included, wonder how having kids changes your risk profile and your appetite for ambition. What has that looked like for you?

Sarina: Having kids definitely changed my perspective. I reflect back and think, what was I doing with all my time before? This whole 996 culture doesn’t work for parents. It will never work for parents. And that’s not what YouPop is about either.

But I have experience, which gets me farther than hustle at this stage in my career. I know what good looks like and I know what bad looks like. What might take someone six hours might take me one hour, because I’ve put in more reps, from doing the hustle culture, seven days a week, 24/7 thing earlier in my career, especially when I was launching Postmates.

Hannah: So the experience compounds into efficiency?

Sarina: One of the advantages of being an older founder is efficiency. And then being a mom, you’re even more efficient. I’m very good at saying no. If it doesn’t serve a goal, it’s a no. If it doesn’t fill my cup with joy, it’s a no. I just don’t do things if they don’t fit one of those buckets, and I don’t apologize for it. If you’re getting a no, don’t be offended. It’s just not serving one of those things right now, but maybe it will later.

The other big thing is that I have help, and I don’t think this is talked about enough. I have three kids under five, I’m building a company, and I live in New York City. I have a nanny. I have babysitters on rotation. Someone comes and cleans our house.

You have to be a bit of a super delegator, because for me it’s much more valuable to spend that hour in the morning with my kids while someone helps make their lunches, instead of scrambling to make lunches myself. I’m a very engaged parent in everything I do, and that’s also because I know how to build teams and delegate accordingly, both in my professional and personal life.

Follow Sarina on Instagram where she shares advice for founders and multi-hyphenate creators, and join the YouPop waitlist at YouPop.ai.

David has kindly offered warm intros to the following roles (some in stealth 👀) to our community. Reach out to him on Substack or Linkedin if you’re interested:

Head of TikTok Shop (NYC) - Mammoth Brands (Harry’s, among others)
Director of FP&A (DC, maybe remote) - CapitalOne Shopping
Chief of Staff / Operating Partner (NYC) - Stealth B2B AI
Chief of Staff / PMO Head (NYC) - Fintech

📣 Get your 5-9 Creator Starter Kit

Find me on: Instagram, Linkedin, Tiktok, Youtube

✋ NexusPoint — Not a tool, but this is the best resource I’ve used so far for hiring assistants and editors overseas (and I’ve tried a LOT) - they take care of everything up to the point of hiring and don’t charge until you onboard someone → Book a free discovery call

💬 ManyChat — The tool behind every “comment X and I’ll DM you the link.” It auto-sends resources to everyone who comments, so I’m not manually replying to hundreds of DMs → Try ManyChat

💬 Stanley — If you’ve been wanting to post more consistently on LinkedIn, this is the writing partner I use. You’ll get a 3-day free trial with my link → Try Stanley

🎙️ Wispr Flow — Voice-to-text that actually works. I dictate messages, prompts, and emails instead of typing, and it saves me hours every week talking to AI → Try Wispr Flow

👩🏻‍💻 Fiverr — My go-to for hiring freelancers for things like design, editing, one-off projects (I use Fiverr Pro to save time on vetting talent) → Try Fiverr

🧊 Othership — The sauna/cold plunge I go to! → Try Othership with my discount

🧾 Xero — The accounting software running the back end of my business. Bookkeeping and invoices without me having to think about it → Try Xero

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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One of the weird contradictions of social media is that you can have an audience of 300K+ and still be scared that no one will show up to an in-person event.

I hosted my third in-person event this week as part of my 5-9 Builders Club, a personal branding workshop with my friend and fellow creator, Claire Barthelemy.

A few months ago I met Claire in person for the first time after being Instagram friends. She’s a multi-hyphenate creator who’s done content for herself and for businesses across six different accounts in 8 years while working and studying. We talked about hosting a workshop for people who want to build a personal brand online, but struggle because they’re doing it on the side of a demanding job, or so multi-passionate and nonlinear that they don’t know what to talk about.

We called it “Niche Famous”, based on our shared belief that it’s better to be known by 1,000 of the right people than 100,000 of the wrong ones, especially if you want to grow your visibility for your career or business. We spent over a month planning, wrangling invites, venues and sponsors. We were still asking ourselves minutes before pressing publish on the invite: “What if no one shows up?!”

520 people signed up.

We were *only* able to fit about 100 into the room.

And I couldn’t have asked for a better room. We had professionals in every field from tech and startups to finance and consulting. People with a decade of corporate experience and new grads. Founders. Creators who already built followings of 100K+ looking to expand to other platforms or refine their brand.

Smart people with real substance who want to build something of their own in their own name, grow their career, and expand their network.

Everyone had realized - visibility is the new currency, whether it’s a tool to promote a new business, to market your own skillset independent of a company, or just to explore a new creative outlet.

I’m sharing everything we talked about that night (I recorded the entire thing) in today’s newsletter:

• The exact slides we presented (everything from tactical content creation to the mindset you need to build a public brand)

• 10 tips for building your personal brand and Q&A

• The worksheet we gave to every attendee to take home and use to build their personal brand positioning and messaging, not just hear about it

But even though we’d prepared detailed slides and a worksheet for our workshop, it was clear by the end of the night that the true value of our event wasn’t the advice, the tips, or the frameworks.

It was meeting other people doing the same thing as you, hearing their motivations, and realizing that you’re not alone in “climbing cringe mountain”…instead of sitting at home watching “how to create content” videos but never starting.

520 of you signed up for 100 spots, which means an in-person event every few months only goes so far, so…

I have a favor to ask you…help me help you!

I want to help more of you, in a deeper way. I know there's no shortage of personal branding courses, communities, and advice out there already. I have no interest in adding to the noise. If I build something, I want it to be something you'll use, and the only way to find that out is to ask you.

Tell me where you are with your personal brand, what you’re stuck on, and what would help most in a quick 3min survey. A few people who fill it out will get a free 1:1 session with me, and you’ll be the first to hear about anything I build.

✨ Fill out the survey (and enter to win a free 1:1 session with me) ✨

Stay tuned here and on my IG stories for future events and more personal brand resources (in-person and virtual soon, I promise!). You can also subscribe to my page on Luma to make sure you see new events as soon as they’re posted.

Read more

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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🗽🗽Attn all (aspiring) personal brand builders in NYC!

I’m hosting an IN PERSON event on Wed Jul 22 to help you become Niche Famous - build a brand that’s seen by the right people to grow your career, network and business!

This post is sponsored by Relay, a business banking platform. Relay is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.

When I posted my first Instagram video in October 2024, I never thought it could become a business that makes multiple six figures a year. It felt like a fun creative outlet, and “content creator” didn’t sound serious enough to be a real career.

My first brand deal came in January 2025 and it shifted my mental calculus. I made $5,000 from posting a single video.

For most of 2025, I made anywhere from $5,000 to $10,000 a month. It still felt like fun money. A nice bonus on top of my 9-5, not a business.

The end of 2025 felt like a turning point. My brand had grown, and a few things hit at once: tech layoffs, AI slop taking over every feed, and brands that suddenly wanted real storytelling from real people. The creator economy was growing fast, and creator-led businesses were becoming a serious path. Going into 2026, I decided to treat this like a real professional asset instead of a side project.

A big part of “taking it seriously” was the financial side. Even though I started my career in finance and knew the importance of finances, it took me a long time to get around to organizing mine because it felt like boring admin that took me away from growing my business.

But “boring admin” is what turns a side hustle into a business. “Boring admin” saved me money and helped me make more.

I’m not a small business finance expert by any means, but here are the five financial moves I wish I’d made sooner, and what I wish someone had laid out cleanly for me when I started.

1. Form your business entity (usually an LLC)

Before you can do almost anything else on this list, you need an actual business entity. For most creators that means an LLC. It gives you liability protection and lets your business income pass through to you without a separate corporate tax.

I did it after realizing I should separate my business income for taxes (which I needed an LLC for), but wish I knew a few things earlier:

• You don’t need to set up an LLC on day one of posting content or starting a business. You can run a side hustle as a sole proprietor for a while before it’s worth the cost and paperwork. Form it once your income is consistent, not the first week you post, consult or advise.

• In New York, there’s a publication requirement. Within 120 days of forming, you have to publish a notice in two newspapers the county picks for you, for six consecutive weeks, and it runs from a few hundred dollars upstate to well over $1,000 in the city, plus a $50 filing fee (NY Department of State).

• After you form an LLC, you can turn it into an S corp to save on taxes (in most cases). S corp is not a separate entity, it’s a tax election you make on your LLC that starts to make sense once your net income is consistently above roughly $80,000, because you can pay yourself a reasonable salary and take the rest as distributions that skip self-employment tax (it’s location dependent; in some cities like NYC, S corp doesn’t save you as much).

Further reading:

• SBA — Choose a business structure and IRS — Business structures

• U.S. Chamber of Commerce — S Corp vs. LLC

2. Separate your business and personal bank accounts

I ran everything through my personal bank account for way too long. Brand deal payments, my expenses, my rent, my groceries, all in the same place. I couldn’t tell you which part of the business was profitable or how much I’d actually made versus spent.

I put this off because setting up a business banking account meant paperwork and sitting in a branch. I switched to Relay recently and wish I’d known about it earlier, because I set up my account in about five minutes from my couch.

Once the money was separated, everything got easier. I could see what was coming in, make decisions, and pay people cleanly.

Relay also makes it easy to set up separate accounts for different parts of the business, which used to be a hassle. You can also give logins to your accountant, a contractor, or an assistant without sharing your own password, which is huge once you start delegating.

3. Set aside money for taxes every quarter

When you’re running a side hustle next to a 9-5, you have a hundred things going on, and this is the one that’s easiest to ignore. I’d seen other people say to set money aside for taxes. I knew I “should” do this. But I figured I wouldn’t make enough in my first year for it to matter.

Then Q4 2025 happened and I made a lot more than I expected, all at once. Come tax time I had to pull out a huge chunk I hadn’t planned for. It would have been so much less painful if I’d been setting money aside quarterly the whole time.

Now I do this with my accountant every quarter. It’s a hassle, and it saves you from a five or even six-figure tax bill you didn’t see coming. The moment a payment comes in, a set percentage goes into a separate account I don’t touch, so it’s already there when taxes are due.

Further reading: IRS — Estimated taxes.

4. Open a self-employed retirement account

A perk of having self-employment income, if you’re not fully self employed, is that you can open a retirement account built for business owners, on top of any 401(k) you already have at a day job. The two main options are a Solo 401(k) and a SEP IRA, and once my income was consistent, my accountant walked me through both.

The difference (do your own research or talk to your own accountant before acting on this!):

• A SEP IRA makes sense if you want simple. It’s employer contributions only, up to 25% of your net self-employment income, no employee piece, minimal admin.

• A Solo 401(k) lets you save more, especially if your business income is still modest. You contribute as both the “employee” (a flat amount up to $24,500 in 2026) and the “employer” (up to 25%). Because the employee piece is a fixed dollar amount and not a percentage, you can shelter a bigger share of a smaller income than a SEP IRA’s 25%-only cap allows. It also has a Roth option.

The part I missed at first: you can fund one of these on top of a 401(k) at your day job. A SEP IRA is fully separate from that plan, so there’s no overlap to worry about. A Solo 401(k) is trickier, because the “employee” contribution limit ($24,500 in 2026) is a per-person cap shared across all your 401(k)s. Whatever you defer into your day-job plan reduces what you can add as the employee of your own, but your “employer” contribution to your own business 401(k) is separate.

One rule of thumb my accountant shared: your day-job match is free money, so contribute enough there to get the full match, then figure out how to load up on your own plan.

If this is confusing, which one you pick matters less than starting. Starting early beats optimizing later.

Further reading: IRS — Retirement plans for self-employed people.

5. Get a business credit card

3 reasons to get a business credit card:

1. It builds credit for your business. A business card reports to the business credit bureaus under your EIN, separate from your personal credit. Build that history for six months to a year and you can qualify for financing to invest in the business without leaning on your personal score. This matters more as your business grows. I’ve been talking to creators who started YouTube channels, launched podcasts, or moved into in-person events, and all of it needs money upfront: videographers, studio space, gear.

2. It protects you from fraud. If a charge is fraudulent, it’s easier to dispute it and get the money back on a credit card.

3. Points. Not the main reason, but you’re spending on the business anyway, so you may as well earn rewards while you do it.

Relay offers a business credit card too, so you can set it up alongside your accounts: The Relay Visa® Credit Card is issued by Thread Bank, Member FDIC, pursuant to a license from Visa U.S.A. Inc.

Further reading:

• Experian — how to establish and build business credit

• NerdWallet — best business credit cards

• Forbes Advisor - Top business credit cards

When I started my LLC, I kept wishing someone would lay all of this out for me in one place as a creator entrepreneur and 5-9 business owner. Nobody did, so I figured it out one piece at a time, and each thing I set up made the business feel more real and me (a little) less anxious about running it.

So don’t try to do everything this week. Start with getting an LLC and separating your business finances.

Thank you to Relay for sponsoring this newsletter!

I got to have dinner with their team in person last month and sat down with their CEO Yoseph West (made him take a pic!) to hear about everything they’re building for solopreneurs and small business owners. It feels like a platform that’s going to keep evolving with me as my business grows, so I’m excited to introduce you to it!

💵 Sign up for Relay 💵

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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The first time I came across Mishti Sharma was from her LinkedIn post earlier this year, where she told the story of how she landed the storytelling job that tech companies were “desperately seeking”:

I instantly stalked her LinkedIn, and realized her career was anything but linear. She studied philosophy at Princeton, worked in finance, joined startups, went self-employed, and somehow ended up leading storytelling at Clay. At the same time, she was writing maildrop by mishti about diaspora stories and getting published in the New York Times.

My conversation with Mishti was a treat because of the range we were able to cover, given how much she’s done in her career, and I’m so excited to share this one with you. We covered:

• making two “low status” career moves in a row, and why you can’t plan your career

• what storytelling actually is and how to do it

• how to become a better writer, and how (not) to use AI

• the value of a personal brand and how to build one

• what a GTM engineer is and who makes a great one

Princeton philosophy to endowment fund

Hannah: Take us back to the start. What were you like in college, what did you want to do, and how did you end up at the Princeton Endowment Fund?

Mishti: I loved college so much. I loved all of school. I majored in philosophy, partly because I was interested in it as a subject, but also because it was the most flexible major and had the least requirements. I’ve always had a strong independent streak. I wanted to take whatever classes I wanted and not be constrained by some department requirement. So I constructed my own experience. I took everything from ancient Greek and Sanskrit to classes that took me to Brazil to study contemporary art and Mexico to study Mayan hieroglyphics. My thesis even combined STEM, psychology, philosophy, and politics.

I loved college so I extended the ride. I did a Fulbright in India the year after I graduated, which was also very self-directed and an amazing life experience. I was trying to postpone coming into the real world for as long as possible, because I had this view that, “Alright, I’ve got to earn some money,” and pretty much the only routes are law or finance for what I’d studied. I had a job offer from the endowment fund, but I applied to the Rhodes and the Gates. I was basically asking, “what can I possibly do to not take this job?” I almost got some of the fellowships, but none quite worked out.

Hannah: But you ended up taking the endowment fund job eventually?

Mishti: I ended up moving back to Princeton. I remember having a huge argument with my parents, because I said, “What if I just moved to Spain and learned Spanish for a year?” And they said, “Are you out of your mind? You have to get a job.” So that’s how I ended up at the endowment fund.

I had a great mentor I’m still in touch with, but as a whole, it was the absolute worst personality fit I could have had with a job. We did a personality test called the Predictive Index.,The whole office had to take it. I remember them, graphing people’s extraversion, formality, and other factors and showing our aggregate results on a screen. I was all the way over on one end of the graph and everyone else was on the other end. It was a very corporate and hierarchical place. “Don’t leave your desk until your manager has left or it’ll look bad” energy. We had these huge sprints every quarter before board meetings where we did insane amounts of what often felt like busy work, but we took it so seriously. It is a great opportunity for some people, but it was just a complete mismatch for me and I wasn’t happy.

Why you can’t plan a career ten steps ahead (and what to do instead)

Hannah: Was there any upside to your finance role?

Mishti: The one upside was that the endowment fund invested in a lot of venture capital funds, which gave me exposure to the startup world from the investor side. I got to travel to India, China, and Silicon Valley to meet VCs, and they’d often bring founders from their portfolio companies into meetings. Watching them, I realized, that’s what I want to be closer to. I’d actually tried starting a company in college, so that pull had always been there. Working at the endowment fund just made it impossible to ignore. That’s what led me to create my own first startup role in 2020, right as COVID was starting.

It was a product growth role—basically me and the founder and a bunch of engineers. I was in Figma designing screens and thinking about UX a lot, and it was a consumer social startup, very different from Clay, which is B2B. We were constantly building and tearing down, seeing if we could build apps or web experiences people would enjoy. During COVID, we started by hosting virtual conversations with authors before eventually exploring a bunch of different product ideas. It ended up being product, growth, community, or whatever needed doing. I was showrunning and hosting shows.

Hannah: Something you’ve said about pivots stuck with me, that you can’t really plan that many steps in advance.

Mishti: Someone in college asked me how to think about career trajectory, what to do when. And I said you can’t really think that many steps in advance. I did one thing, I really liked it. I did the next thing, it was absolutely awful. And when I’m there I think to myself, “okay, not that, but I’m closer.” You’re making little adjustments, and it ends up putting you in the right place eventually.

Hannah: That’s hard to take in the moment, though. How were you okay with it in real time?

Mishti: Definitely hard. I had a really hard time leaving the endowment fund, because my parents said, don’t quit until you’ve found another job. So it was a grind. Every waking moment I wasn’t working, I was talking to founders. I’d spend my lunch breaks on calls and write one-pagers every evening. That felt like a bigger shift because I was exiting the industry entirely.

After that, it’s been adjustments within the startup world, because that has its own status hierarchies. You work at a startup, then you’re supposed to be a founder, the whole tech Twitter status ladder. Or at a startup as a generalist, you should do product, that’s the sexiest thing unless you’re technical. But those felt like much smaller adjustments once I’d found the kind of work that actually fit me.

Building the connections that got her into rooms like Clay

Hannah: You knew Varun for a while before Clay, through a friend. So much of early-stage startups is about the people, not the product, since the product is going to pivot. How do you build those connections, and read that energy from the outside?

Mishti: It started with me wanting to make my first pivot out of finance. I made a list of everyone who was a relevant college alum, all the VC funds I thought were cool, and asked, do I know anyone there. From Princeton, because we’d invested in some funds, I had a few routes in. I looked at portfolio companies at those VCs, saw which ones seemed interesting, and asked, “could I find a connection?” It was a giant mapping exercise. That’s actually how I met Varun. A friend introduced us after I asked who she thought I should know. That was probably the most proactive I’ve ever been, because making that career change felt existentially important.

I still do this. On LinkedIn or Twitter, if I see someone really interesting or like-minded, I’ll reach out. I’ve made a lot of internet friends, more on Twitter before the Elon acquisition, who I’m still in touch with. Sometimes years later, someone you reached out to online might end up working with you. It happens a lot. It’s about being open to finding kindred spirits and reaching out to them.

Making peace with two “low-status” moves simultaneously

Hannah: In your First Round piece you wrote that you made two low-status moves at the same time: joining a cold-email startup and taking a content role there. Coming from the same world, I know how unsexy content reads to finance people. How did you become okay with that?

Mishti: I think people are most worried about that kind of thing when you don’t really trust or know your company that well. If Clay had been the median company, the kind that doesn’t value this role, doesn’t pay it well, doesn’t have career progression for it, then I’d think: why wouldn’t I do my own writing projects on the side, and at work, just play the game really well? I know I can play any game well, I’ve studied all sorts of things. Why wouldn’t I optimize for that and save my soul for myself? But that comes from a lack of trust and knowledge about what the company would value. And it would probably have been a correct assumption at a lot of companies.

What made me comfortable was the proof from the founders, and as Clay grew, the validation that this was one of the most important things you could be doing at the company. People respected it. I wasn’t setting myself back. Money talks, the fact that I was paid well and got a good equity grant made me feel a lot better, because the role felt respected and valued.

Why the same work can be “low status” in one room and “high status” in another

Hannah: So you essentially have to find a place where what the outside world sees as low status is treated as high status.

Mishti: A friend of mine tweeted that some people spend their lives chasing what’s high status, and some people have the conviction that they’re just going to do whatever they’re amazing at, and that it will become high status.

It’s both. It’s being in the right environment where I’ll be valued for this. And then you see it play out. Now everyone in the industry is reaching out asking, how do you do your narrative and storytelling, how can I build teams like this, how can I hire people like this. No one knows what amazing work in a so-far-ignored discipline looks like until someone actually does it for the first time. That applies to any function: community, partnerships, whatever. When you push the boundaries, the industry notices eventually. But being able to push the boundaries of a function assumes you’re in the right container to do it.

Hannah: It’s wild how relative status is depending on the room you’re in.

Mishti: It’s very weird. The endowment thought highly of themselves; they had $36 billion, they were funding these VCs. The VCs would be catering to the us, trying to get our investments—but if you talk to VCs, many of them don’t really respect their LPs that much, or at least consider most LPs to be that smart. The same thing happens between VCs and founders. And if you talk to founders, they often don’t consider most VCs to be that smart. Everyone thinks they’re the one doing the right thing, and it comes with this derisive approach to things outside your bubble. I don’t know why we feel the need to do that as humans, but there’s a lot of it.

What storytelling jobs actually are (and how to get one)

Hannah: Storytelling is having a moment, but how do you actually define the job? Every founder, every PMM, every operator wants to do it, and these narrative and brand lead jobs keep popping up that people say Netflix is paying $775K for, but no one quite knows if it’s comms, content, or something else.

Mishti: I can define what I do now, and it’s different as an IC versus leading a team. After PMM I went back to being an IC and did a lot of foundational narrative work, though we weren’t really calling it that, I was just an IC in marketing. Then we said, okay, this is worth building a team around. So we started the narrative team, which blended social, influencer, all editorial (video and text), and creators. Everything that’s a creative storytelling function, all in one. Notion has done this too.

Our job was mostly responsible for how the world understands Clay and the industry we’re in. PMM, for us, is Clay the product. Narrative is responsible for how people see Clay the company, and whether we’re creating something like GTM engineering as a whole new industry and career, powering the growth of how the function evolves.

Hannah: And now that you’re back to being an IC?

Mishti: About six months in, I realized I was more interested in being a creator myself, learning to do that really well, telling these stories, doing my own one-shot projects. It’s a critical team, and as the company grows, leading it gets super operational. So now my job splits in two. I still lead our messaging on every major announcement, the most fundamental moments for the company: fundraise announcements, a big product moment, a manifesto, GTM engineering expanding into a new region. And the other half is being an in-house creator for Clay, focused a lot on YouTube right now. We just launched a channel for business explainers and journalism about interesting companies and really niche jobs. I source and create those stories. The bet is that if they do well, it’s worth Clay’s investment in me, because once a video blows up it’s an evergreen lead magnet. Clay is such a horizontal platform that we can tie almost any story back to something we do, and if not, it’s brand awareness.

Hannah: This is such an emerging role. For someone who wants it now, how do they even get the job?

Mishti: A couple of things help. One is having a public body of work, ideally writing, or at least including writing. There’s maybe a separate, more video-focused track, so you could combine both, but have at least one strong body of work that shows quality. It doesn’t have to be about startups. If it’s really good, people trust you can write. If it’s about startups, even better.

Beyond that, my general advice on creating jobs: most companies don’t have storytelling strength and want it, especially now. Really learn about a company and reach out. Say, I saw this is what you do, I imagine you’re trying to reach this kind of person, here’s what’s falling short on your website, or, I tried your product and here was my experience, your case studies read like this. Do an audit, give them free advice, and make it good. If you have both of those, there’s no way you don’t get a job.

If someone reached out to me right now and said, Clay has a huge newsletter opportunity, you started a Substack but you’re not active on it, here’s the kind of stuff I’d write, and here’s my writing, what if I just did a newsletter for you? We’d hire them in one second. It’s simple but hard. You almost need years of work to get to the point where you can do it, but it’s possible

How to become a better writer (and how to use AI)

Hannah: To do storytelling you have to be good at writing. Have you always been? Is it a natural thing or a buildable skill?

Mishti: I think I’ve always been good at writing, it’s been my thing as early as I can remember. It ties back to reading a huge amount as a kid. Always maxing out the library, reading at my desk, reading with a flashlight in bed. I’ve kept a meticulous Goodreads since middle school, and it basically averages out to a book a week for my entire life. I was always interested in writing, I just never thought it would be lucrative. I wanted to be an author. I admire people like Jhumpa Lahiri and Joan Didion, diaspora writers and essayists, and I was modeling my path against theirs. So the convergence has been really cool.

I think studying philosophy helped a lot too. You don’t have to study philosophy, but people still don’t register in their souls how critical it is to be able to form a logical argument well and tell it cleanly. Even if you can’t write to make me feel emotion, can you at least construct an argument coherently?

Hannah: You mentioned you use AI a lot. How, exactly?

Mishti: I do, a lot. That First Round piece, I used AI so much, but in a very different way than people assume. I’d say, give me seven different transition sentences from this paragraph to the next, because it doesn’t flow. Or, this logically doesn’t flow, how do we rearrange the ideas? It’s very much how I imagine engineers use AI to code. You have the logic and the vision, and you test different ways and pick what gets you in the right direction. I’ll also write something messy and say, give me ten ways of saying this sentiment, because if you don’t start with anything, it won’t give you anything good.

Hannah: So can writing be learned?

Mishti: I think and hope so. The number one thing is read good stuff. If you don’t think you’re a good writer, read ten times more high-quality things than you do now. When I’m trying to write a short story, I’ll read a short story first to get in the zone. It sounds simple, but that’s where I’d start. People could also learn a lot about argument construction. Argument mapping is an exercise we did in college, and it’s amazing how many people think they have an argument when it’s just an opinion with no logical coherence.

Hannah: Banking helped me here, oddly. Building a PowerPoint slide, thinking about what the header is and what supports it, is a different side of the same skill.

Mishti: Exactly. And it’s important to have people with high standards pushing back on you, who won’t let you put random stuff on a slide. Writing is iterative too. Only about 1% of editors give me good feedback on the bones of an argument. Most say, oh, this is great, great vibes, you’re a great writer. You need someone who goes seven layers below and says, you said this earlier but you’re not backing it up in the middle of the piece.

What a GTM engineer actually does and who’s good at it

Hannah: So many new roles are being invented right now at startups where you don’t need the perfect background. Storytelling is one. The GTM engineer is another, and Clay really created that role. How do you define it, and who’s good at it?

Mishti: Go-to-market engineering is the practice of removing every obstacle to a company’s growth. Any process that’s too manual, too slow, too broken, a GTM engineer should be able to go in and use technology, AI, and systems thinking to automate it away or make it much more efficient.

On who’s good at it: on our own team we have a variety of backgrounds. You don’t need a coding background at all, you can teach yourself anything right now with how good AI is. But you need the curiosity and the ability to break down business problems, plus you’ll either have or learn low-code automation or vibe coding really well. That’s the magic combination. On our team we have a former designer, former software engineers, people from RevOps who did traditional RevOps without AI and shifted into this, people from sales. Now they all heavily use Clay, Claude Code, lots of tools. GTM engineers can be T-shaped. One person’s job is, make our reps 100 times more productive, go sit with them, figure out what’s broken, and solve it. Someone else sits with marketing and figures out how to make event invites, follow-ups, and lifecycle emails more efficient. It’s like data science, you can embed them into different functions. The general skill set is automation and vibe coding plus business fundamentals.

How to build a personal brand that builds you optionality

Hannah: You’ve done a lot to shape Clay’s narrative, which supports your personal brand, and you also have your newsletter and post on LinkedIn. How do you think about your own brand versus Clay’s?

Mishti: I’ve been having the most fun at work now that I’ve realized they can actually converge. Clay and I both get a lot out of what I’m doing. After Clay, which I have no timeline on, but if and when I leave, I’d love the freedom to have a couple of high-value consulting contracts in my sweet spot that fund other things I want to do. Or maybe I’m a creator full-time and that pays my bills and more. It comes from knowing myself. I don’t think I’m that interested in working for another company again, and I don’t want to build a giant company. I want to earn a lot of money powered by just myself.

I posted about this on LinkedIn, but I’ve met people who just give LinkedIn posting advice, not even ghostwriters, charging clients 50K a month. There are so many ways to make money that come from being yourself visibly and authentically online, attracting the right people, and using that. People have already reached out wanting to hire me or asking if I’d do consulting, and I haven’t really done anything yet.

It builds optionality. Even if you never leave your company, it gives you power and a sense of agency, knowing you could do anything. So whatever you’re doing in the moment is really what you’re choosing to do.

The best metric for brand-building: “Did the right people see this?”

Hannah: What’s your best advice for someone building a brand or doing storytelling, whether for their business or for themselves?

Mishti: For both, but especially personal brand, it comes down to authenticity. People know when you’re being real. You can be real about being a hustler salesperson and it’ll work, or real about finding a nonlinear career, or finding your place with storytelling. Whatever it is, lean into what you’re uniquely excellent at and share it publicly.

The other thing, for personal and company both: early on, your success metric isn’t whether you get a thousand followers, or X many likes. It’s, “did the right people see this and reach back out to me?”, even if it’s one or two people. That will always lead you in the right direction.

There’s a Henrik Karlsson blog post about how blog posts are beacons, they say “here’s who I am, let the world see this and the right people will come find me”. Treating it like that is more rewarding and more mentally healthy, because you’re not trying to max out your metrics. You’re there for the right people to meet you. It’s a very human practice at the end of the day.

Connect with Mishti on LinkedIn, read maildrop by mishti on Substack, and check out her First Round essay on betting on Clay.

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Substack in 2026 is like TikTok in 2019.

20K on Substack feels like 200K on Instagram.

The platform crossed 5 million paid subscriptions last year, up 67% year over year. When TikTok was stuck in its US legal limbo, Substack put up a $20M fund just to poach creators off it. Even Charli XCX started a Substack last November and pulled in around 12,000 subscribers in a single day.

The money from just “writing words” adds up. More than 50 writers now make over $1M a year from paid subscriptions alone. A New York Magazine salary survey this March found an anonymous fashion Substacker making $275,000 a year, most of it from brand partnerships, vs. a NY Times bestselling author in the same survey made only $49,000. Emily Sundberg’s Feed Me has 150,000+ readers and the New York Times estimated she pulls in over $400,000 a year from subscriptions (when she only had 60,000 readers), before any brand money.

In an AI world, Substack feels like the analog of digital.

We’re a couple years into the AI slop flood, so the internet is full of generated content that all sound the same. People are tired of short-form content on top of that, to the point that “brain rot” went from a meme to a term in the Oxford dictionary. The reaction has been a swing back toward analog and in-person. CNN ran a piece this January on people “committing to the analog lifestyle” out of AI fatigue, film photography is in a full revival, and run clubs and dinner clubs are more popular than ever.

Substack feels digital but analog: a real person’s voice, long-form, an audience you own (for the most part, and for now) instead of rent from an algorithm. In a feed full of AI slop, a human writing like a human is what stands out. It feels like blogging in the 2010s, except with built-in distribution and less cringey photos.

Substack offers something for everyone. On one end you have Lenny’s Newsletter, a product management and tech focused audience, over a million subscribers and more than $1M a year. On the other you have Maybe Baby and Morning Person, much more personal and culture focused. There’s room for almost anything in between.

The startup cost is one of the lowest of any platform (you don’t have to film or edit), and it’s not LinkedIn, where every professional contact you’ve ever had is watching you post.

So…is it still a good time to start as a new creator? Back in mid-2025, Chenell Basilio, who writes a newsletter about newsletters, predicted that Substack had “12 to 18 months of good opportunity before it gets as crowded as everywhere else.” A year on, that window is still open but closing. The readers are coming in, but the money side only just turned on: Substack just launched early access to Creator Kits a few weeks ago, where creators can build a profile for brand partners to shop from. I got early access as a Substack Bestseller.

Yes, it’s still early. But also…don’t obsess about being early. Just start. I got on Instagram and Tiktok in 2024 feeling like I’d already missed the huge growth cycle, and now I’m at 250K+ followers across both platforms. Timing helps, but showing up and not quitting helps more.

My story with Substack

I had a newsletter before this one that was a weekly list of jobs that my assistant helped curate because I wanted an email list but didn’t want to do any work. It drove some growth but no trust, because a jobs list is a utility. Nobody learned anything about me from it.

I started seriously writing around the end of last year. Since then it’s become my favorite creative practice and the most relationship-building thing I do with my audience. Someone has to consciously decide to sit down and read a long thing I wrote. That’s a completely different relationship than someone double-tapping a reel. I’ve also gained over 2,000 subscribers from Substack alone, reached a 5 figure and growing ARR from paid subscriptions, and even had a post get over 1,000 likes that got reposted…by Substack!!

It’s also the channel that gives me the most clarity behind the scenes on the business and brand I’m building, so I’m probably underestimating all the other ripple effects it has on helping me grow.

Today I’m breaking down:

• Who should start a Substack

• What to write about without forcing yourself into a niche

• How to write something people resonate with and recommend

• Substack’s cold start problem and how to build a growth engine that fits you

• The 4 ways to turn good writing into an income stream

Plus my real growth breakdown from the last 90 days, the actual percentages and where every subscriber came from, what I’d copy from it (and what I wouldn’t).

Who should start a Substack

The simple answer first: you should start one if you like to write, or want to become a better writer. If you’d rather make videos, go make videos. A newsletter you don’t enjoy writing becomes drudgery fast.

But let me get more specific, because “do you like to write?” is too broad to be useful. Start a Substack if:

• You were on the school newspaper, or wanted to be.

• You kept a blog that no one read but you still loved writing it.

• You’re an introvert with a lot of thoughts and opinions, and you want a way to put yourself out there that doesn’t involve a camera (at least not at first).

• You actually like to journal.

• You wanted to be Carrie Bradshaw (in the writing-a-column-way, not in the bad relationship decisions way)

• You get a little thrill from writing an exceptionally well-worded email.

• You’re building something and want to share the behind the scenes story of it.

• You want to get better at writing and thinking clearly, which sharpen each other.

• You have tactical, long-form, how-to knowledge that doesn’t fit into shorter formats.

How to start

Read more

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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A few months ago, Danielle Matarasso sent me a cold LinkedIn message. She has the exact kind of nonlinear, portfolio career I love learning about (and we had a mutual friend), so I replied, and here I am interviewing her for my Substack!

Danielle started in Big 4 accounting, went to Booth for her MBA, and spent five years at a mid-sized tech company. Then she spent a stretch exploring ETA and search funds, and now she’s running her own advisory business, building her LinkedIn presence, and writing AI After Carpool, a weekly newsletter that breaks down AI for parents.

As I learned more about Danielle’s career, I realized she’s building a business in one of the “low status, high income” opportunities I’d been talking about on social media, and one my audience keeps asking me about: helping small and medium-sized businesses adopt AI.

Her firm, Numeriq Advisors, does exactly that, with Danielle handling the implementation herself, drawing on everything she ran across functions at that software company. I knew she’d have a lot to share, whether you’re curious about AI advisory, ETA, or building a portfolio career. We talked about:

• Why she walked away from buying a business after looking at 150 deals

• Her honest take on ETA in 2026, and why it now looks more like VC than the old playbook

• How she’d evaluate a deal now, and where AI creates an edge

• What her AI advisory does day to day, and how someone breaks into this work

• The one skill she says matters more than any pedigree

• How she’s building a portfolio career around her family, and what her ambition looks like as a mom

Danielle's wealth of experience across finance, small businesses and tech is apparent in everything we talked about, so I hope you get as much out of today’s newsletter as I did putting it together!

Why she went to business school, and the post-MBA plan that fell apart

Hannah: Why did you go to business school, and what did you set out to do?

Danielle: I came out of undergrad right after 2008. There was all this PTSD over finance, no jobs, so all of us were running to accounting. Accounting in Canada is rigorous. It’s a three-year internship, the exams are all case-based. Accountants there are kind of the business advisors who go on to become the CEOs of companies. It’s a very different profile than in the US.

I did my internship in Montreal and Toronto, and a third of it in Tel Aviv. I quickly pivoted into M&A, doing buy-side and sell-side diligence, because I wanted to get close to deals. I did a lot of software, because that was the scene then, 2014-2016, when SaaS was becoming a thing. I loved it, but I got stuck on the advisor side and thought, maybe I should pivot completely into tech.

My husband and I started our careers together in Canada, and he wanted to apply for MBAs in the US. I’m Canadian, so my rule was: I’m not moving to the US to watch you do an MBA; I’ll only do it if we do it together. We applied to two schools and ended up at Booth. He went down the traditional finance path. I wanted to try everything that wasn’t finance and accounting where I had come from. My goal was to figure out how to break into tech, maybe do product, because that’s what everyone was doing at the time.

Hannah: How did you first get exposed to ETA?

Danielle: It started halfway through my second year at Booth. I came from a family with a third-generation textile business - very boring, typical immigrant family from Europe. They started by selling small pieces of fabric and built it into a real business. The warehouse was dingy and dark, in a part of town that only later got gentrified. That’s what I grew up with, so when people started talking about ETA, I thought, maybe that’s my version of entrepreneurship.

Before that, I was exploring VC-backed startups, I led the startup trek at Booth, and I thought I was going to go into product in Big Tech. But then I realized I don’t want to be a small piece in a huge pie at Amazon, Facebook, or Google. I figured I’d give ETA a try instead.

I was still risk averse, so instead of buying something myself, I took an offer to work as a CXO. That type of program, run by PE firms and search funds, was just starting then. I was set to go to Pacific Lake, one of the top ETA firms in Boston. I’d signed and everything.

And then life got in the way.

I got married right before business school, to my husband who was in school with me. We figured we’d have our first kid right after, before I started the job. Once you start having kids, you realize that’s not how the world works. You can’t plan everything. I ended up six months pregnant when we graduated.

I had to give up the Boston offer because my husband got a job in Chicago at a family office, which is where we wanted to move. So there I was, post-MBA, all my friends going off to amazing jobs, and I’d just given up my dream offer. Six months pregnant, none of my friends pregnant, wondering what the heck I was doing with my life. It felt really hard. I did consulting for a year postpartum, working up until 41 weeks with my own little business and keeping it going after the baby. But I was still itching to be in tech.

Why you should choose a job for the function over the company or industry

Hannah: How did you get back into tech, and how did you choose where to work?

Danielle: I used my Booth network, which is where the MBA truly did help me. I reached out to the VC I interned for during business school, and they put me in touch with their portfolio companies. I almost took a job I really loved in the women’s health space.

But here’s the thing. The women’s health job was in an industry I thought I was passionate about, but the actual function and skills were ones I hated. The other option was a local job in Chicago, in an industry I couldn’t care less about, but the work itself was fascinating. I’d be leading a new sales vertical: figuring out which vertical to go into, owning the strategy, hiring the salespeople, managing BDRs and reps and a quota.

That’s the thing when you’re figuring out where to go. You can love the company and be passionate about it, but if the day-to-day won’t give you the skills you need, or you won’t enjoy it, it’s probably not worth your time. Because the day-to-day is what you’re actually doing. That’s why I chose the role over the industry.

Running five functions in five years, and why you need to own a number

Hannah: You ended up running a lot more than that one vertical.

Danielle: I spent about five years there. I ran the new vertical. Then I took over customer marketing and product marketing. Then product growth, because we were a software business. At some point account management came under my wing. And eventually I became VP of corporate development, which meant I ran all the partnerships across every vertical. That drove 30% of the business or more in a given year.

So I came for tech, got exposed to ETA, thought I was going to do ETA, life happened, and I still ended up back in tech. Just not in a typical product management role at a big company.

Hannah: How did that distinction manifest in your tech careers vs. others?

Danielle: I see a bunch of my friends who’ve gotten laid off in tech over the last couple of years. When you’re at a really big company at a certain level, our level, and you don’t own anything, it’s hard to trust that you could do something different afterward. Owning something is what proves you can.

Rethinking risk aversion when your “why” changes

Hannah: You took the tech job partly because you said you were risk averse. Now you’ve left to build your own thing. Has your risk aversion gone down, or how did you get over it?

Danielle: My perspective has changed. I was risk averse while I was having kids. I know it’s funny to call a VP role at a good company risk averse, but I knew what my body could handle. You can’t work 50, 60, 70 hours when you’re pregnant or trying to have kids. So back then, my risk aversion was really about protecting my body at that stage of life.

Now my why has changed, which changes my risk aversion. My why isn’t to make tons of money. It’s to feel like, when I get to the last decade of my life, I don’t have regrets. Part of that is wanting less. I have this conversation with peers a couple years ahead of me. They’ve already committed to the second home, the really fancy vacations every year, and they don’t want to strip that away. I’ve been intentional since business school that my wins are my kids having a good education, a safe place to live, a good support system. I have that padding built in, so I’m okay forgoing the very high salary right now for a longer-term build, because I believe it’ll pay off.

It’s almost like that ETA book, “How to Buy a Small Business”, where they show you how much you actually make if you get the exit at the end. Your peers might earn a higher salary at the beginning, but by the time you annualize it, once you get your sale, you end up in the same place. The biggest piece, though, is just not wanting too much in the moment. That’s what’s helped me manage my risk aversion.

Her honest take on ETA in 2026: crowded, expensive, and more like VC than it used to be

Hannah: You’ve spent a lot of time looking at ETA, and you’ve written that it’s gotten crowded, the thesis has changed, debt isn’t cheap, multiples are high. What’s your advice for someone in 2026 about to spend a year looking at 150 deals like you did?

Danielle: It’s a different market now than when I looked in 2018, 2019. There are a lot more people in it. Back then, everyone took the ETA class but nobody took action, so when the actual funds came to talk to you, it’d be me and six other guys in the room. Now it’s you and a hundred other people. I went to the ETA conference in November 2025 and it was insanely packed. I went to the same one in Chicago in 2018 and it was nowhere near as full. There was also a lot less diversity in 2018 than now, which is a nice thing to see. There’s a whole community for women searchers that I’m part of, and it’s really flourishing.

There’s also been a lot of false narratives about how easy it is. You’ve got the bootcamps, the Cody Sanchezes of the world, so much content. Which is great, but it downplays how hard it actually is.

Hannah: What’s pushing the multiples up on small businesses?

Danielle: A couple of things. There was a window, roughly 2000 to 2015, where deals really did get done at two to three, three and a half times. If you go back to the Harvard Business Review book, the whole thesis is buying something for two to four and not above. That’s where the math works.

Now it’s a lot easier to find deals. What you can build with Claude, to go find the companies and mass-email them, just wasn’t possible before. So the barrier to entry dropped, and more people came in. And because it’s been so popularized, Wall Street Journal, my dad sending me articles about young people buying up Boomer businesses, you’ve also got the seller mentality, plus more brokers in the space. So it’s harder to get a quality business at those multiples. You can probably still buy turnarounds for less.

Debt was really cheap for a bunch of years, 2014, 2015, 2016, post-recession, so deals were less likely to fail from a debt-servicing perspective. But if you’re paying a much higher multiple and your interest rate is higher, it’s not the same. The profile starts to look more like VC than the traditional ETA search model from the early 2000s. That’s starting to become clearer. But if you go in with eyes wide open, that’s totally fine.

How to evaluate an ETA deal now: compress operating costs, not the deliverable

Hannah: So how should someone evaluate a deal now?

Danielle: I left thinking I could buy any business as long as it was in Chicagoland. Then you start looking at a lot of businesses and your why comes out. Do I really want to own that? You realize it’s not only about the money. Maybe that’s easier for me to say. I’m a few years post-MBA, I’ve had more of a career, I have kids. I don’t have the same energy to hustle the way I did in my late 20s. If you’re younger, no kids, 25, you can hustle. Once you’re 30, the energy starts dropping.

I started thinking about professional services. It could be done remotely, and I understood the clients and the customers. I looked at tons of deals and realized, holy shit, AI is going to change this industry significantly. And the multiples were insane. I looked at deals at six, seven, eight, nine times. That’s not two to four, that’s twice as expensive, and on top of a complete change in how the work gets done.

Hannah: So what’s the lens you’d use now?

Danielle: You should think hard about how AI will compress your operating costs, not your deliverable. What you don’t want is AI making the actual product easier to deliver. If I run an accounting or bookkeeping business and AI can automate the deliverable itself, then at some point that business isn’t relevant anymore.

What I’m looking at now is purely youth enrichment. Dance studios, martial arts. AI isn’t going to replace the teacher in the room. But AI can take a real bite out of the operating costs behind it. I can probably have three or four people do the work that used to take eight, nine, ten, especially if you’re rolling up a lot of locations. So AI reduces your operating costs without touching your product delivery. That’s how I think about an ETA business in 2026.

What Numeriq does, and why she’d rather “teach businesses to fish” than hand them a deck

Hannah: That’s a great segue to Numeriq. You’re doing a lot of the work you would have done in ETA, just in a different way, still focused on small and mid-sized businesses. What does the advisory do, day to day?

Danielle: A few things. Every career skills assessment I’ve ever done, at Booth and through work, always came back the same: I like to learn and I like to teach. Things are changing so quickly that I’m not doing repetitive work. I’m always learning a new way to use a tool. And because I was an operator for so long, I don’t do it like the M&A consulting days, where you hand someone a deck, here’s the value of the company, and walk away. I’m teaching them to fish. They get the tools, they learn how to use them, and they keep running with it.

So it might be setting up Claude for a whole team. I pick a couple of lanes. A big one is the sales process. Another is content and demand gen, taking all the content you have and repurposing it effectively, pre and post events, your podcast, your customer journey. Another is building AI CFOs if you understand the accounting world.

A big part of my job is helping them figure out which workflows cause the most pain, in terms of time, not even money, and where AI truly fits to help them do better.

The most valuable career skill to build: driving revenue

Hannah: What’s the experience you think is most valuable for what you do now, and how do you get it if you haven’t been thrown into a bunch of functions? Your experience running everything at a smaller company, knowing exactly what your customers go through, is what lets you do this now. It goes against the Silicon Valley line that when you get on a rocket ship you don’t ask what seat. The seat matters, because it gives you the skills to leave and build on your own.

Danielle: Anything close to the customer, with a number tied to that customer. Whether that’s a sales number, a marketing number where you’re on the hook for a certain amount of closed-won revenue, or an account management role where you’re responsible for upselling a customer by a certain amount. As long as you’re tied to a revenue number.

I know that sounds obvious. But at the end of the day, a business is a business because you make money, because you have paying customers. You can build whatever you want and think you’re building for the right person, but if you’re not actually selling it to them and seeing the attribution back to customers who spent their money, you’re missing how you learn the most. You can dream up all these wonderful ideas with the engineers, but the person selling it is the one who really understands why it isn’t working, why it isn’t what the customer wants.

Hannah: Why do you think so many smart professionals, especially MBAs, avoid that?

Danielle: A lot of MBAs avoid sales with a ten-foot pole because it’s so freaking hard. The biggest shock in my first role was hiring salespeople and reps and BDRs, and coaching them. Listening to their Gong calls, giving feedback on how they talk, on discovery. You can’t appreciate a sales pipeline review until you’ve owned one. Or you look at marketing and ask, did this event drive leads? If not, was it because I didn’t have a pre and post event process? Did I not figure out the right ICP? Are we marketing to someone adjacent to our ICP instead of the actual buyer? Am I getting to the decision makers? All of that is so important and so hard, which is why MBAs don’t touch it. It feels not intellectual. But it’s the most intellectually challenging thing you can do. So anything that teaches you how to sell, period.

Hannah: At the highest levels of the most coveted post-MBA jobs, finance, consulting, it’s really just sales. Glad you called that out.

Living in two worlds, and refusing to go all in on either

Hannah: You made decisions that optimized for family over career at certain points, while staying a very ambitious person. A lot of ambitious women struggle to reconcile those. How do you think about it?

Danielle: Part of why I launched my Substack is that I was living in two worlds. The parenting world, and my MBA and work-friends world. I was trying to bring them closer together, because there are a lot of women right now who, if they’re not up to speed on how the world is changing, are going to get pulled further and further out. Seeing how much my friends didn’t know is what pushed me to start it. It’s purely for fun right now.

It’s going to forever be an identity crisis, and it’s probably not going away. The only way it goes away is if you live in a world where all your kids’ friends, and their moms, happen to be the same ambitious career women as you, and they probably won’t be. What you have to focus on is being really intentional about spending time in both places. If you don’t spend time in the community where your kids are, that’s not good for them or your family. If you don’t fill your cup with ambitious women, that’s not good for you either.

You’ll forever have two different worlds. You just have to find a way to be okay with that, and make time for both. Don’t neglect one over the other. Don’t go all in on mommy and forget about your brain.

Building a portfolio career on AI advisory, content, and ETA

Hannah: Your Substack, AI After Carpool, shows the different sides of who you are. How are you thinking about your career as a portfolio going forward, and where do content and personal brand fit in?

Danielle: AI After Carpool started as a passion project when a friend asked me, “What’s Claude?” And I thought, oh my God, what is going on. My friends are still using it like it’s a search engine. I have friends in really good corporate jobs, and corporate is actually part of the problem, because they limit what you can use for security reasons, so a lot of people aren’t even dabbling in their personal lives.

So the newsletter fills my creative junkie mind and my teaching itch, and it forces me to think about new ways to use AI in my own life and systems. It feeds from what I’m learning in the consulting work, and what I build there tells me what to share with my audience at a more accessible level, so people can actually start using it.

Hannah: And it brought you back to ETA in a way.

Danielle: Going deep on AI After Carpool, I kept realizing the skills our kids will need in the next 10 or 15 years are very different from the playbook we were given. Be smart, go to school, get good grades, get a good job, save, retire. That’s not a thing anymore. That’s what brought me full circle. If I’m going to do ETA in the future, I want to invest in something I care about that will actually bring value, which is in-person experiences for kids that AI can’t replace. That becomes even more important as we see what social media and screens do.

So it all comes together. The consulting brings in money right now and I’m learning. AI After Carpool lets me share that with my network. And the biggest thing for me is helping my friends understand what’s even possible, for their careers, their creativity, and raising kids in a world that’s shifting. The personal brand piece, I’m just trying it. I’m out of my comfort zone. I’m more of a shy person, I’ve been off social media for a while, I’m improving as a writer. But I’m curious, and curiosity wins.

Follow Danielle on LinkedIn to watch her build in public, and subscribe to her Substack, AI After Carpool, for practical AI tips (especially if you’re a parent).

• Startups Program Lead – Vercel (Dev Tools, Late Stage, SF)

• Business Operations – Town (AI, Early Stage, SF)

• Senior Associate, Strategy & Operations – Maven Clinic (HealthTech, Late Stage, NY)

• Finance Lead – Partiful (Consumer Social, Early Stage, NY)

• Business Operations Associate – Partiful (Consumer Social, Early Stage, NY)

• Founding Product Lead – Nooks (AI, Growth Stage, SF)

• 📢 Build a Nonlinear Personal Brand in 14 Days

• ✨Play career tarot cards

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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Today’s post is on a topic I've been thinking about a lot because I'm working on a new series on Instagram on building a personal brand in your 5-9 as a knowledge creator (stay tuned!!).

I know a lot of us are probably sick to our stomachs hearing about personal brands…but this is slightly different view I hope you’ll consider xx

And stay tuned - I also have a VERY exciting interview dropping in next week’s issue with someone who will talk more about her nonlinear career and building a personal brand in a very unique way!

My resume is all over the place.

When I was 21, I started my career in equities sales, then moved into real estate banking…both in Hong Kong. Then I left finance for tech (more specifically - at a global ride-hailing company that was launching in Latin America). Then I got an MBA to pivot into product, but ended up doing product marketing at a B2B SaaS company. Now I’m also the founder of a creator business.

If you just looked at that on paper, you’d probably ask the same thing many interviewers did:

“So what do you actually want to do?”

I’ve sat across from people who were visibly confused, trying to work out how any of that added up to the role I was interviewing for.

If that’s you, you know the feeling. You spend the first ten minutes of every conversation justifying your path instead of talking about what value you bring. You sound defensive. And the longer you spend explaining, the more you start to sound like the exact thing you’re afraid of being called: an unreliable job hopper.

There’s a way out of that, and it’s the same solution whether you want a better job or something bigger, like your own business:

You build a personal brand.

My definition of a personal brand (there are many others!) is simply what you’re best known for, which you can eventually build, amplify and monetize into a brand or business based on your expertise and point of view. The latter is often what you see referred to as a “personal brand” more broadly.

There are about as many reasons to build a personal brand as there are definitions. You might want to:

• Land jobs

• Get promoted

• Build an income from sponsorships

• Grow an advisory business

• Network in your industry

• Hire talent

• …

If I were to sum it all up:

A personal brand brings you more opportunities so you can attract, not chase.

And people with nonlinear careers have the most to gain from building one.

When your career path follows a straight line, your title and your resume explain you. You show up in LinkedIns searches for “Product Manager” or whatever job you want because it’s already the title you have. Or you look like a star founder when fundraising because you have years in an industry.

When your career zig zags, you're left to do the explaining yourself, over and over. You don’t show up on recruiters radars because they can’t search for you by title. When you’re starting a new venture you look completely inexperienced in your field or function.A personal brand fixes that.

You craft a clear story that you can get in front of the right people so you skip the explaining and attract opportunities instead.

It’s what got me numerous inbound offers like this one despite having less than 2 years of formal “marketing” experience in my title and a very nonlinear career:

It’s what gets me 90% of my brand deals, with brands like LinkedIn, Notion, and Adobe.

It’s what gets people I admire in my industry (marketing, startups, creator economy) to reach out to me instead of the other way around for networking.

Without a story, you look like a flight risk, and you spend interviews explaining it instead of selling yourself. That’s the visible cost, and it’s the one people focus on. The cost we rarely talk about is what all that explaining does to you on the inside.

Without a brand, you feel like an imposter

A reader put it better than I could:

“I find that most people self-select themselves out of opportunities, especially boxing themselves into what skills they have and don’t. My background is years of consulting, I struggled with burnout and a toxic culture, and I was impacted by a layoff last fall. I’m trying to overcome the rejection from interviewing at multiple high-growth startups, and I’m scared to build and learn in public to build a brand. But I’m also seeing the pattern of others like me afraid of not just the rejection, but the fear of believing you’re worth the opportunity and the skill needed to thrive in a high-growth environment.”

I know this feeling well. When I left banking I was burnt out, and the startup I joined next was intense in a completely different way. While I was job searching, and even after I joined, I feared for a long time that I couldn’t “hack it” in a high-growth environment.

I had invented a story that everyone around me seemed smarter, sharper, better at execution, and I assumed I was the weak link. Because I was the one with the nonlinear path and they had done the job or held the title for longer than I did.

What I eventually figured out is that imposter syndrome starts before day one. It’s not really about whether you can do the job (in most cases, you absolutely can). A lot of it is set in motion before you ever walk in the door.

When you apply for a role you don’t obviously fit, you spend the whole process shaping yourself to it.

You trim your experience to match the job description, downplay the parts that don’t line up, and try to make the square peg fit the round hole. By the time you start, you’ve spent weeks making the case to yourself and others that you sort of belong, so you walk in primed to look for proof that you don’t. That’s where the imposter feeling grows.

A personal brand flips that entirely. When you’ve put out a clear case for what you’re good at, people come to you, and they’re the ones fitting a role to you instead of you contorting to fit theirs. You don’t have to explain yourself, which is the thing that sets off the imposter feeling in the first place, so you start on solid footing.

My friend Yuqi, who I interviewed for this newsletter, is a great example of this. She leads Developer Community with no formal community experience. Instead, she’d built a brand that articulated why her product background and her habit of building community in public made her the right fit. She showed she could do the job before she her first interview and never had to justify her experience against the job description line by line.

And sometimes the role doesn’t even exist until your brand creates it. My friend and mentor Upasna recently joined the American Journalism Project in a Head of Product & AI Studio role at the intersection of journalism, AI, product, and venture. It was created for her, because her brand made it obvious she was the person for a job nobody had even written down the job description for yet.

With a personal brand, opportunities come to you

And it’s the new normal of how hiring will work in the post-AI era, because AI has made it too easy to fake competence.

You can generate a resume, a cover letter, and a portfolio with ChatGPT in 20 minutes. You can use bots to submit hundreds of applications.

Earlier this year, we were hiring for a role at my startup and got flooded with applications. Many were clearly AI-generated. Sifting through resumes where we had no idea if the person actually did the work they claimed was exhausting. Most of the people we interviewed came from referrals, or had worked at a similar company in the same role with experience that was legible and a track record we could verify.

But the person we ended up hiring came in through their personal brand. They’d posted a portfolio publicly, including a teardown of one of our competitors showing how they’d redo the strategy. We reached out, interviewed them, and hired them. They didn’t have the exact title we were hiring for, but they’d already shown they could do the work.

This happened to me too. I got two job offers last year. Both came from startup founders who reached out after seeing my LinkedIn content. Posting publicly helped me rank higher in search, and it gave them a whole body of content that showed what I was capable of before we ever spoke. They could see how I think, how I write, and what I care about. I went into the interviews from a position of strength because they had reached out to me, not the other way around.

And it’s the same content that does double duty. The brand that gets you hired is the same one that attracts clients, an audience, and eventually sponsors if you want to go that way. You build the asset once and it compounds in multiple directions.

How to start building your personal brand (30min version)

No, a personal brand is not built in 30 minutes. Or a day, even.

I’ve been building my personal brand for almost two years, with lots of false starts, and trial and error.

But what you can do in 30 minutes is start nailing down the positioning that serves as the foundation for your personal brand, and map out a few first steps to kickstarting the personal brand engine.

Your positioning is, in a nutshell: Who you are, what you’re great at, and why your path makes sense. Distilled down to 1-2 sentences you can reuse everywhere. (If you happen to be a PM or PMM, this is just product positioning adapted to yourself.)

The template version:

FOR [target audience/employer/investors], I AM A [how you describe yourself] WHO PROVIDES [unique value], UNLIKE [default comparison, competitors] BECAUSE I BRING [unique combination].

My positioning, which I adapt from the template version, after spending time figuring out each [bracket]:

I’m an investment banker turned marketer blending business and creative to help B2B brands and high-achieving professionals turn storytelling into revenue.

It’s the first thing you see on my LinkedIn description and how I connect my experience across marketing, my personal brand, and my past experience in finance, business school and B2B SaaS.

Here are three ideas to write yours for a nonlinear career path, if you’re stuck or the template feels too robotic:

1. Anchor around an industry.

Say you’ve spent years in finance and you want to move into operating. You lead with the industry as the throughline:

“I’ve spent years around top consumer companies and saw how the best ones scale, and now I want to bring that inside one as an operator.”

2. Emphasize your skill stack.

If your value is the combination of things you’ve done, lead with that. Say you’ve worked in finance and then operated at a startup, and you’re going for a VC role:

“I’ve worked in finance and as an operator, and a VC role needs both, understanding the numbers and helping founders actually run the company.”

3. Frame around a core question.

If a single thread of curiosity connects your jobs, name it. Say the same question pulled you from sales to customer success:

“I’ve always been curious how companies solve customer problems. That took me through sales and then customer success, and now I want to keep chasing it as a PM building for the customers I used to sell to.”

Your goal isn’t to pretend your path was linear. It’s to show you’ve thought about it and can say why it makes sense for the role you want. Most people with nonlinear careers waffle there. They either downplay their past experience or try to explain every single job. Neither works. And positioning isn’t fixed - it changes with you.

Pick one framing that connects your dots, iterate until it feels right, and evolve it when it shifts.

Your positioning statement is the foundation, but it does nothing sitting in a Google Doc. Once you have it, there are three ideas to put it to work:

1. Put it where people check you out.

Rewrite your LinkedIn headline and About section so the first thing anyone sees is your positioning, not your current job title. This is the part that made founders find me in search and reach out before I’d applied to anything. Do the same with your bio, your email signature, and how you introduce yourself in a room.

2. Turn it into content.

Your positioning is the source material for everything you post, so you’re never stuck on “what do I even talk about.” You’re just showing the work behind the claim. That can be a competitive teardown (like the one the person I hired did), a breakdown of how you’d solve a problem in your space, or thinking out loud about where your field is going. You don’t need to go viral. A handful of LinkedIn posts (or another platform, depending on your industry or goal) is enough to give someone a reason to reach out.

3. Use it to reach out.

Once you can explain yourself in one line, cold and warm outreach get a lot easier. Message the people doing the work you want to be doing, with a clear ask, and let your positioning and your supporting posts do the vouching for you.

The first time you do all of this it’s slow and it feels cringe. That’s normal. But once your positioning is out in the world and you’re posting against it consistently, it stops being just a line you use in interviews and starts bringing the opportunities to you.

If you want a structured way to do this…

I built a Nonlinear Personal Brand 14-Day Sprint in Notion. Basically…how I’d coach you to do all of this in 2 weeks.

It breaks positioning down element by element so you can actually build yours, then turns it into 14 concrete daily steps, 30 minutes or less each, to refresh your LinkedIn, publish your first posts, and send your first outreach. You come out the other side with the real beginnings of a brand instead of a plan in your head to start one.

• Chief of Staff – Stealth startup w/ Tanmay Tankha (Early Stage, San Francisco)

• General Manager (Stanley) & Chief of Staff – Stan (AI Content, Growth Stage)

• General Purpose Smart Person – Tofu (AI GTM, Early Stage, Toronto/NYC)

• Venture Fellow – ResilienceVC (FinTech VC, Washington DC)

• Founding Marketing Lead & Expansion GM – Marble Health (HealthTech, Growth Stage)

• Chief of Staff (2 roles) – Global media co & AI startup, via Omna Search (NYC)

• Chief of Staff – Navan (Travel & Expense, Late Stage)

• Strategy & Operations Manager – Rula (HealthTech, Growth Stage, Remote)

• Director, Office of the CEO (Founder in Residence) – BillionToOne (Molecular Diagnostics, Public, Menlo Park / Hybrid)

• 📢 Build a Nonlinear Personal Brand in 14 Days

• 🧭 The Exit Plan for ambitious people figuring what’s next

• ✨ career tarot cards

• Find me on: Instagram, Linkedin, Tiktok, Youtube

These are my top posts over the last 6+ months since I started writing every week, sorted by category.

Guides cover frameworks and how-tos across career strategy, personal branding, AI, and startups. Stories are conversations with people who built nonlinear careers, like a former product manager turned developer community lead and creator, to an ex-pro tennis player who built a personal brand on LinkedIn.

If you’re new, start anywhere that catches your eye. If you’ve been here a while, have a look at anything you missed.

See you in two weeks! In a very Chinese time of my life until then 😆

Career Strategy

• The Career Changer's Guide to Job Offer Negotiations

• Why I Went to Business School (and My #1 Takeaway)

• How to Onboard Yourself: Your First 90 Days at a New Job When There's No Playbook

• 11 Career Paths Where High Performers Have an Unfair Advantage

Personal Brand & Content

• How I Grew 70K Followers in 4 Months as a 5-9 Creatorpreneur

• So You Want to Start a Newsletter?

• I Thought Personal Brands Were Dumb Until It Got Me a New Job and a Six-Figure Business

• The 5-9 Creator Guide: How I Grew a 6-Figure Side Hustle in a Year

AI & Future of Work

• Why You Need an AI Second Brain (and How I Built Mine in 45 Minutes)

• Everyone Is Going to Have a Nonlinear Career

• How to Build a Fulfilling Career and Not Get Replaced by AI

Startups & Business

• The Multi-Passionate 5-9 Builder's Guide to Focus

• How to Get a Startup Job in 2025

• 7 Ways to Succeed in Startups (from People Who Actually Did It)

Ambition & Achievement

• What to Do When You're Ambitious but Nothing Excites You

• Why I'm Choosing the Low Status, High Income Path to Wealth

• Escaping the Bermuda Triangle of Talent

• The Maximizer's Dilemma (Why You Should Stop Keeping Your Options Open)

Career Pivot, Founder & Creator Stories

• What They Don't Teach You at Business School (Wharton MBA to creator chat)

• How to Turn Your Passion Into a Profitable Lifestyle Business Without Burning Out

• How a Music Grad Turned a Viral Substack Into an AI Career Platform

• How a Wall Street VP Built a Wellness Business Without Leaving Finance

• How a Microsoft Sr Director Reinvented His Career and Built a Personal Brand Without Ever Leaving His Company

• How to Build a Portfolio Career by Investing in Relationship Currency

• How to Use a Gap Year to Pivot and Rebuild Your Career

• How an Ex Goldman Banker and PE Associate Broke Into Startup Ops

• How an Ex-Pro Tennis Player Pivoted From Banking to Startups with Her Personal Brand

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

🌴🌴 This will be my last post for a few weeks. I’m headed on vacation for two weeks and taking a full break (or at least, trying). I’ll be sharing some of my old posts and guides in the meantime!

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Is it just me, or are a lot of ambitious, accomplished people feeling really stuck right now?

In the past few weeks, not one, or two, but four friends have told me they’re feeling stuck, unsure, or stagnant in their careers and lives, and asked me how to get out of it.

One is a founder who can’t decide whether to pivot her startup or go get a job. One quit an intense finance job for tech and now feels unstimulated outside the high-pressure environment she used to complain about. One is burnt out from years of long hours building other people’s startups and wants to start a lifestyle business of her own. And one knows she needs to leave her job but has no idea what she’d do instead.

Call it a rut, a funk, the messy middle…More and more of my circle in their late 20s and early 30s seem to be going through it, especially the ones who are a year or two post-MBA or a few years into finance, consulting, or tech. They’re often silently wondering what’s next, afraid to admit that their perfect-on-paper careers aren’t perfect in practice, or even a little guilty over their “champagne problems”.

And it goes way beyond my group chat. Social media is full of it. I see TikToks every day of people “starting over at 30” or “I quit [insert name brand company here] and have no idea what’s next.”

It makes complete sense. A lot of us feel unaligned with corporate jobs that turned out to be bullshit work and stakeholder management theater instead of the impactful, exciting roles we were promised as high achievers. Meanwhile, a lot of those paths are falling apart in front of us anyway, between layoffs and salaries don’t move much each year.

How do I figure out what’s next?

My answer to this question was why I started creating content 2 years ago, so it’s one I still get a lot. I’ve written and spoken about my own life after banking, when I felt apathetic about basically everything, and how I slowly clawed my way to figuring out what came next.

And I’ve been back in that place more times than I can count: During my MBA, after I crossed product management off my list and didn’t have a backup plan. In the middle of a job at a mid-sized company that I didn’t love. Late last year, when my content felt stagnant and nothing about it excited me anymore.

It’s a question I’ll probably never get tired of answering, because I’ve been through it in so many forms. I know how hard and how impossible it feels when you’re inside it, and helping someone climb out is one of the most fulfilling things I get to do.

So I wanted to write down what I told my friends over the past few weeks, because I’m sure a lot more of you are feeling the same way.

This is a little different from my usual stuff. I’m a tactical, matter-of-fact, non-woo-woo person, but this one gets a bit woo-woo, because it’s kind of a woo-woo problem to solve.

A couple of notes before we start:

This isn’t a long how-to guide. It’s a loosely sequential mix of principles, mindsets, and a few specific things I’ve actually done that helped. If you want something more structured, I’ll point you to another resource at the end. But in my experience, when you’re in the messy middle, throwing a framework or a worksheet at you right away just adds to your anxiety without helping.

Feeling excited about nothing is a different problem from having too many directions and not knowing which to prioritize. That second one is related, but an easier one to solve, and I wrote a separate guide for it: a pragmatic multi-hyphenate’s guide to focus. My advice below is for when your well of inspiration feels dry.

1. Relax and realize: This is the oldest problem in the world.

Figuring out what’s next is a problem that’s existed for as long as humans have. When you’re in the thick of it, the not-knowing feels like a personal failing, like everyone else got handed a map and you’re the only one wandering around without one. Seeing it as the oldest human problem there is takes a real amount of pressure off.

My founder friend rambling at ChatGPT about which AI app to build is wrestling with the same thing as the hunter-gatherer deciding where the tribe should roam next, or the medieval craftsman paying to have their fortune read. (In a way…)

I was reminded of this recently on a visit to Mass MoCA, the contemporary art museum, where I saw an interactive exhibit on tasseology, the ancient art of divining the future from coffee grounds. Armenian artists and experts in the craft trained an AI model to read the grounds and generate your “fortune.” Here’s mine.

Humans have never stopped inventing ways to see around the corner: reading tea leaves, casting the I Ching, studying the stars, consulting the Oracle of Delphi, reading animal entrails in ancient Rome, cracking oracle bones in ancient China, turning over tarot cards. Different centuries and problems, but same craving to know what happens next.

But the not-knowing is the human condition. The struggle of figuring it out isn’t a glitch in your life or something you did wrong, but the eternal experience of being a person, where the only way past it is through.

Zooming out like this to begin always helps me. Knowing that people have wrestled with this exact not-knowing for as long as we’ve existed, often on far more life-or-death terms than a career pivot or a crossroads in my business, somehow makes my own version of it feel smaller and more solvable.

2. You’re numb. Clear the mental and physical fog first.

Rest and regulate your nervous system.

If you’re anything like me, when you’re in a career or life rut your instinct is to live entirely in your head, thinking harder, trying to brain-power your way out. I still do this and constantly need to take my own advice. But the first and biggest fix usually isn’t up there in your head at all.

I recently reread the book The Body Keeps the Score by Bessel van der Kolk, and the core idea is right there in the title: your body keeps a running tally of your stress, and when you’re exhausted, wired, tense, and anxious, you physically can’t access what you actually think or feel. You can’t trust your instincts or locate your interests if you can’t even hear them over the noise.

When I quit banking, where I’d been working 80 to 100-hour weeks with my body stuck in fight-or-flight, it took months of sleep, rest, and real relaxation before I could hear my own thoughts again. At one point I even went on a seven-day backpacking trip with no cell service before things finally got quiet enough.

I know what you’re thinking: I don’t have months. You don’t need them. Here are the things that have given me that same effect in bigger and smaller doses over the years:

• Sleep and eat. Actually get your eight hours and eat real food.

• Move. Something physical and intense to burn off the stress: a long run, dancing, martial arts, tennis.

• Get offline and into nature. Phone-free walks and hikes, ideally somewhere out of your city.

• Bodywork and woo-woo resets. Massage, acupuncture, sauna and cold plunge, breathwork, sound baths, sage smudging, reiki, or recreational drugs (be careful, and none of this is medical advice).

• Get it out of your head. Journal, or if free-writing isn’t your thing (it’s not mine), turn on your phone camera and just talk, stream of consciousness.

• Bring in help. Therapy or coaching.

3. Take a side quest.

Stimulate and explore.

Stop trying to solve the problem for a while, and go do something fun or creative that has nothing to do with it.

When you run straight at this kind of problem, you usually get nowhere. It’s the same reason the answer to a hard work problem or a relationship issue tends to show up in the shower, or on a walk, or the second you stop forcing it.

Researchers call it the “incubation effect”: your brain keeps working on the problem in the background once you step away and let your mind wander, and that’s often when the insight actually shows up.

In other words, you need a side quest.

A very random, very incomplete list of side quests:

• Take in art and culture. An art museum, a movie by yourself, a concert or a festival.

• Explore somewhere new. Travel somewhere you’ve never been, walk around a neighborhood you don’t know, or go vintage and thrift treasure hunting.

• Make something with your hands. Creative writing, pottery, painting.

• Learn something random. Show up to a talk or event in an industry you know nothing about but are curious about.

• Go woo-woo. A tarot or astrology reading, a meditation retreat, or plant medicine like ayahuasca (use caution, and none of this is medical advice).

4. Get external input, selectively.

Once you’ve cleared some fog and taken a few side quests, so you’ve got a little distance from the problem, outside input starts to actually help.

A few forms this can take:

• Talk to a friend, or someone who’s walked the path you’re eyeing. A single conversation probably won’t hand you the answer. But your friends see a version of you that you can’t see from the inside, and someone who’s navigated the same thing can tell you what worked for them.

• Talk to someone whose life you find interesting. You might not know what you want, but you probably know a few people who seem energized by what they do. Ask them about it. You’ll learn a lot about what you’re drawn to and what you’re not. If you don’t see someone like this right away, ask a friend to introduce you to someone they think could help. If you don’t know anyone, I interview people in this newsletter with interesting paths - a few places you can start:

  • How to turn your passion into a profitable lifestyle business without burning out

  • How to build a portfolio career by investing in relationship currency

  • How to use a gap year to pivot and rebuild your career

  • How an ex Goldman banker and PE associate broke into startup ops

• Talk to old friends and family about what you were like as a kid. This is getting external input from your younger self. As we get older we lose track of what actually makes us tick, and our talents that showed up early (you always made art, you built insanely intricate Lego sets) usually keeps resurfacing in different forms.

One caution, and it’s why I say to do this selectively: if you lean too hard on other people, whether friends, family, coaches, or experts, you can end up chasing something just because someone told you to, or because it felt assigned to you. That lands you right back at square one the moment you realize you’re stuck again.

And speaking of woo-woo, I created a free career tarot card game to help you start figuring out what’s next! Swipe through paths and tradeoffs, and get a career archetype with practical ideas for your next move.

5. Just try something.

This is going to sound useless to you right now, because your immediate reaction will be “but I don’t know what to even try.” Fair.

So while you’re working through steps 1 through 4, keep a running list of anything that sparks even the faintest interest. Then pick the first thing on it and go.

And if you’re still coming up empty, stop trying to manufacture an interest that isn’t there.

Start with something you’re good at and don’t hate. Do more of it, or try it in a new form. Maybe you’re good at building slide decks at work. That might not feel like a calling, but think…what’s another way to use that skill? Could you make Canva graphics for local events, or build yourself a personal website? Pulling a thread you already have will get you moving faster than waiting around for a brand-new one to materialize out of nowhere.

Silver lining…

When I quit banking, and again during my MBA, the “stuckness” felt enormous, and those pivots felt huge and scary. What I’ve noticed since is that the closer I’ve gotten to things I actually like doing and feel aligned with, the smaller the pivots have become and the less scary each one feels. Really, they don’t feel like pivots and more like small adjustments.

So if the leap in front of you looks massive right now, it won’t always be that way (I think!). The more honest you get about what you actually want, the shorter the jumps get in the future.

If this helped, let me know, and please send it to a friend who’s in it right now (or bookmark it for the next time you are).

The Exit Plan

If you’re actively figuring out your next career move and want a much less woo-woo resource, The Exit Plan is an interactive Notion guide that gives you the structured guide for mapping your exit with frameworks, calculators and trackers that you can work through at your own pace over 5 weeks.

The goal is to get from “I can’t name what I want” to a next move you actually test. I almost ran it as a $400 live cohort, but turned it into a self-guided product so more of you could use it.

The Exit Plan →

• Build a Nonlinear Personal Brand in 14 Days to finally explain your career path and attract inbound opportunities

• The Exit Plan for ambitious people figuring what’s next

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

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Congrats to everyone who’s graduating in May! I’m at my brother’s graduation this weekend, so I figured I’d take this week’s newsletter as an opportunity to share the recording and takeaways from a Substack Live I did last weekend with Alexis Barber and Simi Shah, two fellow creatorpreneurs who also got their MBAs from Wharton.

If you want the full tea though, you’ll have to watch the live 🍵

For a long time, I was embarrassed to call myself a “creator” after getting my MBA.

Wharton grads are supposed to go into consulting, banking, PE, big tech, or a startup with a real title. Posting on LinkedIn and building a personal brand is not on that list.

It felt weird until I started getting to know Simi and Alexis, who graduated from Wharton the year after me. Simi runs South Asian Trailblazers, an award-winning podcast and media company, and advises C-suite execs on marketing strategy. Alexis hosts Too Smart For This, a podcast with 150+ episodes, wrote a book published by Penguin Random House, and built a creator business after working at YouTube.

Why we went to business school

For me, there’s an official answer I tell people and a real one.

The official answer is that I wanted to pivot into product management. I’d come up through investment banking and tech strategy and ops, and Wharton was one of the only ways to make that move without taking a huge pay cut at a tiny startup.

The real answer is that I was living in Latin America right after the pandemic, it was a lonely time, and I thought business school would be a silver bullet that fixed my career, network, social life, and a lot of other things that were not going so well. (It wasn’t.)

Talking to Simi and Alexis, what came through is that the three of us walked into Wharton from genuinely different starting points. Simi had already built South Asian Trailblazers into a real platform before she applied — a podcast with traction, a growing community, an advisory practice. Alexis came in straight from launching YouTube Shorts at Google, with her own creator work already in motion. Neither of them was using the MBA to find a career. They were using it to build on top of one.

What business school actually gave us

It taught me the thing I thought I wanted was not the thing I wanted.

I got the product internship I’d been gunning for, realized I didn’t want to build products from the back end, and pivoted toward launching and storytelling instead. The silver bullet came as a result of realizing business school was not the silver bullet.

The network also took longer to mean something than I expected. In school you meet everyone, but you don’t really know who’ll stick around until after graduation. Some of the connections that I relate to the most — including with Simi and Alexis — only became real after we were out of the bubble.

One of my favorite moments in the conversation was Simi describing comparing herself to a past version of herself, walking over the same bridge in Philly beause she came out of the MBA more confident in her business and vision.

For Alexis, the MBA was more additive than reinventive. She kept scaling Too Smart For This through school, landed her Penguin Random House book, and treated the two years as a platform on top of what was already working. She talks about her time at Wharton as a chapter where she blended “cultural fluency with strategic rigor” — and that’s a pretty accurate way to describe how she navigted it. She came in with the audience and the cultural read, used Wharton for the operational and strategic muscle, and walked out with both.

Our 3 different post-grad paths

My path was the most typical of the three, at least at first.

After the product internship didn’t pan out, I took a chief of staff role on the go-to-market side at a mid-sized B2B SaaS company. On paper, the dream business school outcome — fully remote, well paid, normal hours, reporting to the CEO.

A couple months in, my very clear thought was: this cannot be it for me. The job was fine but felt stagnant.

Content was the thing I’d been thinking about but avoiding for years. Once I started doing it on LinkedIn — badly and publicly, in front of the same classmates who would actually see me — it became how I got my current marketing job at a startup.

Simi didn’t take a corporate job after graduation. She went full-time on South Asian Trailblazers and her advisory work with C-suite leaders on digital branding and strategic communications. Her business now is a media company, a community, and an advisory practice running in parallel — the podcast keeps building reach, the community deepens the platform, the advisory side monetizes the strategic expertise the platform proves.

Alexis didn’t take a corporate job either. She went full-time on her creator business and has spent the year out of school building it like an actual business, not a brand exercise. The Penguin Random House book is one piece of it. The 11K+ subscriber Substack is another. So is the personal branding coaching she now offers — cohorts, 1:1 work, office hours, a course launching at $500+ — that turns the audience into revenue without burning her out.

So when people talk about post-MBA paths as “consulting vs. tech vs. PE,” the three of us are a useful reminder that it’s also “salaried job vs. founder vs. founder-with-different-business-model.” All three were available to all three of us. We all picked differently.

Why building publicly is so “cringe” in school

Business school loves entrepreneurship in theory, but it has a very specific idea of what serious entrepreneurship looks like.

The classic business school startup is an AI company with a pitch deck, no revenue, and a few classmates nodding about TAM. Meanwhile, Simi and Alexis already had real businesses with customers and revenue — Simi’s podcast and advisory work, Alexis’s media and audience — but the perception in school could be completely different.

If you’re building a creator business, hosting events, or making money from something that looks too internet-native, the questions you get are “Why don’t you just be an influencer?” and “Is this a serious thing?” In the cringe stage, that’s hard to brush off. So I waited until after graduation to even think of building a platform.

At Wharton, I’d hear classmates talk about people who posted daily snippets from their lives. They weren’t even trying to build creator businesses. They were just posting for fun. And people would still talk behind their backs and say it was ridiculous. The thought “who does she think she is?” is everywhere.

How to start creating content from scratch

The first version of my content calendar came from posting my career story on LinkedIn and letting people book free calls with me. I did around 20 of those calls, treated them like customer research, dumped the notes into ChatGPT, and asked what I should post about.

If you don’t want to do calls, the better question is: where does your alpha come from? (Yes, I used to work in finance in case you couldn’t tell!) What can only you say in a way AI can’t copy and a stranger can’t paste into a chatbot?

If you’re summarizing the news or reporting on trends in a way anyone could say, you’re competing with everyone. The better question is what only you can say that the people you want to speak to actually want to hear.

Going to business school can be a source of alpha. So can working at a top company.

Simi has been doing this for years through South Asian Trailblazers, and her advantage is specificity. She didn’t try to be a generalist career platform. She built for a specific community, with a clear point of view about who she was elevating and why, and grew the audience and the advisory book on the back of that focus. Her alpha is the depth of her niche.

Alexis’s advantage is different. She came from inside the platforms — she launched YouTube Shorts at Google — and she now teaches the operational and strategic side of personal branding to ambitious women. Her alpha comes from having been inside the systems she’s now creating on.

The 3 questions to ask before getting an MBA

These are the 3 questions I suggest that everyone ask before they get an MBA:

1. Do you actually need the MBA to pivot into your desired industry or next role?

2. Will it tangibly increase your salary or earning potential?

3. Do you care about the network it will bring you?

Sponsored consultant who doesn’t hate the job and is fine with two years of party adult summer camp? Go.

Trying to break into banking or consulting? Still one of the clearest paths.

Trying to do social media at a B2C brand? Building content on Instagram is probably the better proof point.

Trying to break into tech or startups? Writing thoughtfully on LinkedIn can do more for you than the degree.

I’d be careful about the MBA as a vague “I need to figure my life out” move. The environment will pull you toward whatever everyone else is recruiting for that week.

Simi and Alexis answer this differently than I do, because I came in trying to pivot. They came in to compound.

The three questions above are most useful if you’re using the MBA as a career change, which is how I was using it. If you’re using it to invest in something already running — like Simi was with South Asian Trailblazers, or Alexis was with Too Smart For This — the math changes. The ROI is less about salary or pivot, and more about how the two years compound what’s already in motion: the network, the credibility, the time, the proximity to people you’d otherwise have to chase. Simi has written about her version of this calculation from the founder side; both of them are evidence that the founder version of the MBA decision is a different question than the career-pivot version.

More on this:

• Simi’s article: Was my Wharton MBA worth it?

• Watch This Before You Get an MBA (YouTube)

• Why I went to business school (and my #1 takeaway)

Who goes to business school (and who doesn’t)

People at the very top of their careers, who already have it figured out, usually don’t go to business school.

Business school has a high floor. Most people there have already achieved a lot — Ivy League, banking, consulting, tech. But people running million-dollar businesses or raising tens of millions of dollars are not going to business school.

In some startup circles, especially on the West Coast, you get more street cred for being a business school dropout than a graduate. On tech Twitter, the MBA can actively count against you because it signals you’ve always operated inside the traditional path.

That said, Simi and Alexis are both walking arguments against it — Simi running a media company, community, and advisory practice; Alexis running a creator-author-speaker business with brand partnerships, a Penguin Random House book, and a paying community. Building something during or after business school is evidence that you can do more than collect credentials during it.

The most important thing we each got out of the degree

For all of us, it was the people - genuine friendships, interesting connections that helped us grow our careers and as people, and of course, meeting my boyfriend in my case too!

Follow Alexis and Simi

Alexis Barber

• LinkedIn

• Substack: Too Collective

Simi Shah

• LinkedIn

• Substack: Sense

• Manager, Business Strategy & Analytics – Chicago Bulls (Sports, Chicago)

• Chief of Staff to the CEO – Factorial (HR Tech, Growth Stage, Barcelona)

• Chief of Staff, Marketing – Clay (AI, Late Stage)

• Strategic Partnership Manager, AI Ecosystem – GridCARE (AI/Energy, Startup)

• Applied AI Claude Evangelist, Startups – Anthropic (AI, Late Stage, SF)

• Product Specialist – Sequence (FinTech, Early Stage)

• Strategy/Product Hire – Casper Studios (AI, Startup, NYC)

• The 14-Day Nonlinear Personal Brand Sprint

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

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A few weeks ago, I started building a system I’m calling my AI Second Brain. It’s slowly but definitively transformed how I work and given me hours back across both my 9-5 and my 5-9.

I’ve shared pieces of this on Instagram and LinkedIn but I know not everyone catches everything. I wish I’d done this intentionally three months ago, so if this is the nudge you need to do the same, I’ll be happy to have shared it in detail here!

The problem: your AI sounds like AI when it doesn’t know you

AI generates slop when it doesn’t have context. Over the past year, I’d gotten increasingly frustrated with AI because I felt like I kept having to prompt it the same things, upload the same files, and keep re-explaining that I hate the “not x, not y, but z” AI slop cadence that you see in the worst LinkedIn thought leadership posts ever.

The solution: a second brain that gives your AI context that it can keep building on

What I mean by “second brain” is a folder of markdown files (a fancy kind of text file) on my desktop that any AI agent on my computer can read, that tells it:

• who I am

• how I sound and write

• what I’m working on at my 9-5 and at my 5-9

• what rules to follow

• what skills it knows

That way, when I open a new chat with any AI agent that’s connected to it (ChatGPT Codex, Claude, Perplexity, for example), it doesn’t ask me who I am, what I sound like, or what I’m working on. It already knows.

I built this for my 5-9 after watching my team in my 9-5 do this for the past few weeks, and seeing the dramatic impact it had on making everyone’s AI outputs better.

You can start this in just 45 minutes. The point isn’t building the most sophisticated AI-pilled system out the gate in that time, but rather, having an MVP you can keep improving. The longer you wait, the more daunting it feels and the more you think you have to build before you start. (same goes for building anything new!)

The benefits of having a second brain:

1. It works with any AI you use. A second brain is a folder of markdown files. It doesn’t care which agent you point at it. If you’re mostly seeing Claude content on Instagram, it’s because there are so many Claude tutorials being made there.
   
   **Don’t get locked in, because LLMs are surpassing each other all the time. Lately, I’ve found GPT-5.5 on Codex better and cheaper in token consumption than Claude, which I’d been using up to now.

2. Drafts come back 90% ready, not 30%. When I ask for a LinkedIn post or a newsletter based on my voice notes, my AI already knows my positioning, who my audience is, that I never use empty phrases I hate like “That matters” or “quietly”. I’m editing the last 10% instead of prompt-engineering and context dumping my way to the first 90%.

3. No crossover between your lanes. Your AI stops putting personal context into work emails or work jargon into brand pitches. You can route context to specific tasks.

4. It grows and improves every week. Every new project, decision, or skill file you add makes the next output sharper. After a month, your second brain is denser than anything a fresh chat could replicate, no matter how many files you upload.

What’s in my second brain

The basic setup is simple and similar across other guides on this you’ll see. At the top level, I have 3 core files:

1. IDENTITY.md: Who I am, what I do, what I’m building, what I care about.

2. VOICE.md: How I sound, words I use, words I avoid, sentence patterns, tone, examples of my best writing.

3. RULES.md: The routing layer that tells the AI which files to read for which task.

Then I split my life into lanes, with each one being housed in one folder:

• /work for my 9-5 context

• /content for my creator business

• /personal for values, habits, lifestyle context, and anything else that shouldn’t get mixed into work outputs

• /skills for repeatable tasks

A skill is a markdown file that teaches AI how I do one task. I have skills for things like writing a LinkedIn post, drafting a newsletter, reviewing a brand deal contract, writing a carousel, and humanizing AI drafts so they stop sounding like generic slop.

Instead of prompting from scratch, I can say roughly what I want, and the agent knows which process to follow.

Real example: how I use this system

For this newsletter, for example, I gave Codex posts I wanted to repurpose as a longer guide and sent a long voice note on what I wanted to say in the post. Then it read my newsletter skill, which tells it exactly how to write like me, dozens of my past newsletter samples, which include edit logs that show what I’ve historically cut from AI drafts.

That’s a very different starting point from opening a blank chat and saying, “write this in my voice” and pasting a long prompt.

Of course, I still go through every draft, but it cuts the time I spend writing my weekly newsletter from hours to ~30 minutes.

5 steps to build your second brain

»Here’s the full guide. «

The basic steps look like this, but you don’t have to pay too much attention because the guide includes prompts you can paste into your agent to ask it to guide you on all of these steps.

1. Create the folder and the empty files. Three top-level files (IDENTITY.md, VOICE.md, RULES.md) plus the lane subfolders. Empty .md files are fine. The next step fills them.

2. Run the starter prompt. The prompt in the guide interviews you with a few questions per file and writes your first version in about 30 minutes. You’ll edit and add to it as you go.

3. Add skills as you notice them. Any task you do more than two or three times is a skill candidate. Capture how you do it once, and you’ve taught your AI to do it for you forever.

4. Wire up RULES.md so it routes correctly. Be specific. Something like: “for newsletter writing, read /content + /skills/newsletter, not /work.” This is what keeps the system feeling intentional instead of a pile of context.

5. Run a 15-minute weekly ritual. Block time every Sunday to update what changed: a new project at work, a new positioning idea for content, a task you did three times this week that should become its own skill. Without this, the brain goes stale fast. With it, it gets denser every week.

What I’ve added since the first version

Three things that have made mine better since creating my v1:

Moved the folders from my desktop to GitHub. Once your brain is doing real work, you don’t want it living on one laptop. A private repo gives you version history, a backup, and sync across machines. It also makes you less scared to make big edits, because you can always roll back. If you don’t know what this means or how to do it, ask Chat after you have your second brain and it will show you how!

Let my AI write its own skills. When I find myself prompting the same task three times in a row, I ask my AI to write the skill file for that task itself. The brain grows itself.

Weekly audits. Old context gets in the way of new context. My guide includes a prompt you can give your agent to update the brain itself on a weekly basis.

Further reading and more perspectives on building a second brain

Needless to say, especially if you spend time on X, there are hundreds of people who have started building context for their AI months (probably even years) before me, and mine feels like the tip of the iceberg in comparison!

Here are a few resources I’ve learned from along the way.

• Ruben Hassid on AI workflows for creators and operators - his Substack has a lot of great guides and it’s where I started

• Tiago Forte who first coined “second brain”

• Andrej Karpathy on context engineering and “Software 2.0”

X has the deepest and latest versions of this conversation. Instagram and LinkedIn are downstream of it. If you’re serious about building a second brain, start following people who talk about building in AI there. These 3 are great people to start with, and you’ll be down the rabbit hole yourself in no time.

one last thing…think of AI as your team

The best way I like to think about building my AI second brain is like creating a big Notion space for a team, with all the context that new employees coming in need to know in order to succeed in their roles.

You wouldn’t expect a new editor or EA to do good work on day one without context. You’d give them a doc. You’d tell them how you sound, what you care about, what’s off limits. AI works the same way. It just doesn’t ask for the doc, so most people never write one!

If you’re frustrated with how some people on the internet are talking about AI transforming their work and businesses while you’re still prompting for hours to get the right output, take time this week to start building this. 45 minutes of setup will give you back hundreds of hours over the next year.

If you build one, reply and tell me if it’s helped and how you’re structuring yours. I love seeing how people adapt this and learning together!

» If you scrolled to the bottom, here’s the full guide again! You can copy paste this directly into your agent!«

• Pick my brain here

• Free resources

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Interesting jobs from my network that caught my eye

• Strategic Consultant – Applied Intuition (AI/Auto, Late Stage, Sunnyvale)

• Portfolio Services Partner – a16z New Media (Media/VC, Late Stage, NY)

• Director, Global Markets Operations – Chief of Staff – Visa (Fintech, Public, SF)

• Strategy & Operations – TLDR (Media/Newsletter, Growth Stage)

• Founding GTM, US – Rexi (AI/Fintech, Pre-Seed, NY)

• Entrepreneur, CEO Office – Handshake (Career Tech/AI, Late Stage, SF)

• Open role – Stepful (HealthTech/EdTech, Growth Stage, NY)

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

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A few months ago, I wanted to clean out my wardrobe and level up my style as a chronically busy person who hates shopping. I searched “stylists in NYC” on Instagram and found Chelsea Hollenbeck, the founder of Good Lines.

I was initially nervous about working with a stylist (what if we didn’t vibe, what if it was too expensive). But working with Chelsea opened my eyes to two things at once: the value of personal style, and (because I’m always thinking about nonlinear careers and businesses) how intentionally she’d built her lifestyle business after pivoting from nursing!!

What struck me almost immediately is that this isn’t just a job for Chelsea. It feels like an extension of who she is and a true passion. Every part of it feels like only she could be running it.

Even as she was the one asking me questions in our session, I had a running list of my own: how she’d built Good Lines from scratch while still working as an oncology nurse, how she grew it into the fully booked practice, how she hired and marketed. I asked her if I could interview her for my newsletter because she navigated what many of you are thinking about or doing: turning a passion into a real business. I also wanted her style advice for ambitious people, especially after you leave the corporate path.

We talked about how Chelsea went from googling “how do you make a website” after a night shift to where she is today, what taste and curation mean as core business skills (and why they matter more than ever in the AI era), how to build personal style when you’re no longer dressing for a corporate uniform, and the question every aspiring lifestyle entrepreneur should be asking themselves before they start.

Why she quit nursing and how she decided on a styling business

Hannah: What were you doing before Good Lines?

Chelsea: I’m a registered nurse, and I still have my license. I’ll always keep it. That was the very first job I had out of college, and the only job I had until I started this. I worked at a hospital in Minneapolis for seven years.

I felt very burnt out. I wasn’t finding any joy going into work. There was one day I just looked around and thought, I don’t want one person’s life here. I don’t mean that in a bad way at all. Just: this is not what I want for my life.

I’ve always been very creative. I’ve always loved fashion. My mom’s an interior designer. I grew up in Miami, around fashion. It was something I’d always done on the side for friends. As many people can relate to, my parents were very “job stability, education first.” I was actually a pretty good nurse — I did well with patients, I understood the work.

Hannah: When did you know you were going to leave?

Chelsea: One day I just looked at my husband and said: I can’t do this anymore. I had a lot of anger and resentment inside myself. Why did I choose this? Now I’m stuck forever. All I have is a nursing degree. I can’t do anything but be a nurse. I had a full-on midlife crisis at 28. I’m 32 now.

Hannah: What got you from that realization to doing something about it?

Chelsea: In October 2022, two months after we got married, I worked a night shift, came home, and just Googled, “how do you make a website?” I made this janky little website. I was like, I’m going to start doing what I do on the side for my friends and family. I’m going to make it full time. I don’t know what the hell I’m doing. And I just started.

Eventually I quit. My husband and I moved to New York City. He’s a pilot for Delta, so he can live anywhere. I said, I want to move to New York. I don’t want to live in the Midwest anymore. I’m originally from the East Coast. That was it. One of the craziest decisions we ever made. It almost broke us. There was a lot of risk.

Hannah: Were there other things you toyed with, or was it pretty clear from the start that styling was what you’d go after?

Chelsea: It was kind of fashion-related for a while. I thought about doing secondhand shopping, being a curator for vintage pieces. I have a great eye when I thrift. Maybe I’d have a vintage shop and style people through it.

I also toyed with getting my Botox license and offering styling on the side. My business name, Good Lines, was actually because that’s what I wanted to name my Botox business. We have lines on our face, and I’ve always been very body positive. I’m more of a natural person and I didn’t go down the Botox path. But I kept the name. Style is linear too, in the sense of figuring out where the lines on your body are, where your hips fall in relation to your ankles, where everything sits. That’s the formula. And our bodies are beautiful, they do great things for us. So, the name Good Lines stuck.

Side hustling for two years before going full-time

Hannah: How long did you side hustle, and what was the tipping point to go full-time?

Chelsea: I did hybrid for the first two years of the business. The tipping point was when revenue was enough for me to justify not picking up the nursing shifts. My husband and I talked about it financially, what made sense for us. I had a goal number. When I finally hit it consistently for a few months, I said: I think I can make more. The only reason I’m not is that my time is only 50% on this.

Hannah: What did the side hustle look like day to day during those two years?

Chelsea: I was fortunately in a nursing job where I could work as much or as little as I wanted, kind of per diem. After we moved to New York, I worked as an IV nurse for a private company, going to homes and apartments to give IVs to people who were hungover or sick. I’d run around the city with my little suitcase part-time while I was building my website and making content. I was living two lives.

Hannah: And how did you make the actual call to go full-time?

Chelsea: Eventually I decided to stay employed by them but didn’t pick up any shifts for a month. I just wanted to see how it went. I gained a lot of new clients in that month, and I just took the risk.

You have to see enough clarity to know it’s pointing in the right direction, but there’s always going to be an element of risk. It’s never just, “now’s the time and it’s going to work.” It’s making an educated guess, like you would for anything.

Transferable skills from nursing to running a styling business

Hannah: Did you ever feel guilt or shame about making this pivot?

Chelsea: Absolutely. There’s already a lot of unspoken hierarchy in nursing culture. ICU nurse versus med-surg nurse. Nurses who’ve worked 25 years versus five years. “I’m a tougher nurse than you because I stuck it out.” To me that’s complete BS, because every nurse plays a pivotal role in the patient experience.

I felt like I was wasting the gift my parents gave me of college. Now I have this degree I’m not using at all. And I felt: who in the world would ever want to hire me? I didn’t go to fashion school.

In the beginning I felt like a poser. I felt shame, embarrassment. I was like, who do I think I am? I belong in scrubs and back in the hospital. That’s what I chose, now I’m stuck. People judged me. They said, “you’re leaving nursing? That’s weird.” Nurses are very tight-knit — they hang out together, do everything together. I didn’t feel supported. I had to get through all of that.

Hannah: What surprised you, looking back, about how nursing prepared you for running this business?

Chelsea: My nursing career parallels what I do now in a lot of ways. Nursing taught me time management, leadership, communication, and how to match what a person needs.

I have clients who are quiet, low-key. I have to match that energy. In the hospital it was the same. Some patients you could drop F-bombs with, super casual. Others were very type A, family observing every little thing. You have to be a chameleon. I’m able to mold to my clients’ needs the same way.

People talk about their bodies. They talk about their insecurities. These are things I talked about with patients too. The communication, the time management, the ability to wear multiple hats. That’s what made me a stronger business owner.

The styling is the easiest part of the job — and the fun part. It’s running the business that’s more difficult, and that’s where my nursing skills come in.

Getting her first clients and networking her way into NYC

Hannah: How did you get your first clients?

Chelsea: My very first client was a friend of mine. Another nurse, but at a different hospital. She followed me on Instagram and was like, “I love that you’re doing this. I always admired your style. I’ll pay the 50 bucks. Let’s do it.” That was my first review.

Then someone found me on Instagram completely randomly. At the time I was living in Minneapolis. We did in-person shopping, and I got photos of her, and I started building a portfolio.

A friend referred me to someone she knew, a woman in private equity, very high profile. She referred me to a couple of other women. It started to grow.

Then we left Minneapolis, so I had to do a whole new networking push.

Hannah: How did you build a network from scratch when you moved to New York?

Chelsea: When I first moved to New York, I went to a networking event the second day we lived here. I had boxes to the ceiling. I went to that event and thought: I should just make my own networking group. So I made one. I ran a networking event every month for a full year.

It was a way to literally make friends, because I’d just moved here and didn’t know anyone. It was also a way to show my presence. I had this blank slate of New York. No one knew me, I didn’t have that nurse tie anymore. I met a lot of incredible women at those events, and I made some very lovely friends I’m still close to.

Hannah: Looking back, was there a habit from those early years that mattered more than you realized at the time?

Chelsea: Once you get the ball rolling, you have to pay attention to when things are coming at you and grab them. The window is small. Whether or not you do anything with it, you at least have to see what’s behind it.

I’ve responded to every single email I’ve ever gotten. Always. Especially in the first few years, because I did that and didn’t ignore some of them, there were a couple I was doubtful about that ended up being some of the largest catalysts of my business.

How she figured out content and built a recognizable brand on Instagram

Hannah: Your content is how I found you in the first place. How did you figure out what to post?

Chelsea: Content has always been hard for me because it takes a lot of planning. (I’m not a content queen like you.) But I started doing get-ready-with-me videos and client transformation videos. I had a part-time assistant, a student, who came and followed me around taking videos.

Now I have someone designated to help with content. I’ve thought about taking it a step further and having a full-time team do it. I think it would help the business grow. I just mentally have to prepare to schedule time for content, which I’m not super interested in. But social media is a huge way to grow your business.

I looked up the popular hashtags for my field. I tested out different types of videos. Whichever ones got more positive feedback (comments, shares), I’d follow that trend for a while.

Hannah: When did you start thinking about your page as a brand and not just an account?

Chelsea: I decided my page should look like a brand. I keep it cohesive: same color palette, similar font, all of that. It makes your business look more professional. It legitimizes what you’re doing. You want people to remember you by something. A color, a font, your face. It’s like Coca-Cola or the McDonald’s arches.

How she protects what she loves from becoming what burns her out

Hannah: It’s clear you love what you do. How do you protect the thing you love from burning you out?

Chelsea: You have to set boundaries and allot time for yourself. Whether it’s “I’m closing the computer at 6 o’clock” or “I’m not taking on this client again because they were unkind to me.” Those boundaries matter.

Hannah: What about when the thing you love is also part of the work, like shopping for you?

Chelsea: If it’s something you’re passionate about, you have to make time to do it just for you. I love to shop — I could easily find something for myself when I’m out browsing for a client. But I try not to. I’ll go Saturday morning by myself, just to see what I like. No clients, no agenda. That’s how I keep the joy in it.

And the power of saying no. Sometimes that’s the whole answer.

How to build personal style after the corporate dress code disappears

Hannah: A lot of my audience is leaving traditional corporate jobs and the dress code that comes with them. If I’m thinking about style as my own (as opposed to tied to a job), how would you suggest someone start designing that from first principles?

Chelsea: The cold hard fact is that we walk out of our homes every single day and we have to put clothes on. How you show up and how you want to represent yourself, unfortunately, is very important. I wish we could all wear a brown paper bag, but that’s not the reality.

I think it’s important to stop seeing it as “oh, that’s a fashion thingy” or “I’m not someone who cares about that.” You don’t have to. It doesn’t have to be an interest or something you keep up with. But dressing a certain way commands a presence. It helps show your personality. It builds confidence.

The clients I have who care less, when they put on outfits I help them with, they tell me, “oh my god, I felt so good in that presentation today, because my outfit was so good.” Not because they were thinking about their outfit. There was just something that made them feel like, I have this.

Especially as a woman in a position of power, or in a male-dominated field, the way you show up is really important. The first thing people do when they see you is see you. Visually. Before they hear your voice or anything else. It’s what you look like when you walk into a room.

I try to help people think about it less as “being a fashion girly” and more as: what is your presence? What message do you want to convey when you walk into a room?

Hannah: What’s a practical first step for someone who wants to start being more intentional about it?

Chelsea: Take a look at your closet. Separate what you actually wear from what you don’t. Look at the pieces you reach for and find the correlations. Is it color, pattern, fabric? When you understand what you actually wear, you become a more educated shopper for yourself.

There’s a way to bring color into a professional setting, by the way. A lot of clients say to me, “Chelsea, I love color, but I work in a corporate job and I feel like I have to wear black.” That’s not necessarily true. There are ways to keep things professional while letting your personality show.

I also tell people: try things you might not normally try. You don’t know how you’ll feel in something until you do.

Why taste and curation matter more in the AI era (and how to develop them)

Hannah: Your entire job is taste and curation. In my world, people are talking about taste and curation as one of the most important skills in the AI era because AI can generate anything but it can’t tell you what’s good. What does taste mean to you, and is it something people can develop?

Chelsea: It’s not really something I think about consciously. Like anything, people have their niche, their talents. A good singer is just a good singer. They can improve with a coach, but they’re always going to be a good singer. Someone who can’t sing just can’t sing.

I think taste is more innate. Curation is more learnable.

Taste, when I shop for clients and style them, is truly a feeling. I visualize the person in the item — their personality, everything we discussed. That’s how I know. I’m like, you know what, I really think she should try this. He should try this.

Hannah: How would you describe curation, then, since that’s what people can develop?

Chelsea: Curation is more like having an outline of what it is you need. Like if you’re cooking a meal and you need a recipe, you have to find the ingredients. If you’re looking for a vintage item, you do your research on top vintage sellers. You look at different neighborhoods. If you want a higher-end thrift item, you go to a thrift shop in a wealthier neighborhood. Curation can be learned.

Chelsea’s #1 advice for turning a passion into a business

Hannah: What’s your number one piece of advice for someone with a passion (styling, fitness, cooking, design, whatever) thinking about turning it into a business on the side?

Chelsea: Just rip the band-aid off and do it. That is my absolute best advice. Never take no for an answer. Just do it. Don’t care what anybody says or thinks about you.

It’s going to be shit in the beginning. It’s going to be hard and weird. You won’t know what you’re doing. But the difference between the people who succeed and the people who fail is that the ones who fail give up. Don’t give up.

Connect with Chelsea on Instagram and at Good Lines!

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

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In April 2025, I hit 100,000 Instagram followers after creating content for 6 months.

By December 31, 2025, I’d barely grown, ending the year with just under 110,000 followers.

This year, I’ve grown to 180,000 in 4 months.

That’s 70,000 followers in 4 months, after about 9 months of near-flatlining.

Engagement followed the same shape: dead for most of 2025, then back.

Brand deals followed too, including the biggest single deal of my creator career so far (multiple five figures for 1 video), alongside others with OpenAI, Anthropic, Amazon, Microsoft, and LinkedIn.

I didn’t write this to brag but to offer a candid reflection and tactical guide for anyone creating content in 2026, especially if you’ve hit a plateau, are shifting niches, or are trying to reposition yourself. Because 6 months ago, I didn’t think this was possible.

This is specifically about my experience on Instagram, but 90% of the advice applies whether you’re building a personal brand for your career, for a creative pursuit, or as founder-led content for a business you’re growing.

If you’re completely new to content creation, you might want to start with the piece I wrote last year on building my content business from zero as a 5-9 creator. I cover how to get started when you have no idea what your content should be about, who your audience is, or where to reach them. Think of this as Part 2, but it’s still legible if you haven’t read Part 1.

Why I wasn’t growing

Before I could reposition my content and grow this year, I had to examine what was going wrong, both qualitatively and quantitatively.

I had started my content journey in 2024 by sharing “career advice”: leaving investment banking, breaking into tech, tactical job-search tips, and reflections on business school.

I had momentum from going viral in late 2024, an audience I’d grown into, and a sense that I’d “found” my niche.

The problem was that the niche I’d found, and the story I told (”career pivots and leaving banking for tech and getting an MBA”), had gotten stale. I was talking about breaking into tech and finding a new job when tech was laying off thousands of people every week.

At the same time, I left a big tech company for a startup and focused more on the creator economy and my 5-9 personal brand than on building a “corporate career,” even though that was still much of the content I created.

But I’d been told (and told myself) that you have to stick to your niche, post consistently, follow the formats that work, and not confuse the algorithm.

So I posted what I thought my niche demanded. It felt mechanical, and it became a vicious hamster wheel: I wasn’t excited, so the content wasn’t great, so it didn’t do well numbers-wise, so I felt more pressure to post things that “worked,” which made me less excited.

By the end of 2025, I’d convinced myself I’d plateaued, that people weren’t interested in what I was saying anymore, and that I’d probably exhausted my creator lifespan. I thought I should happily accept that this was a side project I’d make a bit of money from and leave it at that.

To reinvent yourself, you first need to reset and reposition

The result of the vicious hamster wheel was that I was unmotivated to create. I couldn’t open the camera, never wanted to hit post, and didn’t even want to scroll because I felt so stagnant compared to other creators. But I also couldn’t get off the hamster wheel, so I kept making mediocre things.

What forced me off it was taking a 2-week vacation at the end of the year, saying “f*ck it,” and scheduling my top 10 past-performing videos as reposts.

What started as a way to avoid creating turned into a way to examine what excited me and what didn’t about the content I’d made in the past. An audit and a recalibration.

And what moved the needle was realizing I’d been focusing on a “niche” when I should have been focusing on my audience and my positioning.

A lot of people use “niche” and “positioning” interchangeably but they’re not the same. Your niche is the topic you cover. Your positioning is what makes your content different from everyone else’s when you speak to a specific audience, because of what you uniquely offer that’s distinct from what’s already out there.

I needed to reposition. And to do that, I had to go back to my audience and ignore everything else: my old content, other creators, the algorithm.

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

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“Every nonlinear career path eventually leads to entrepreneurship.”

Last month I was on CAPS LOCK, Sam Feher’s podcast for ambitious people who want to live bigger, better, louder, and longer…and this is what we concluded, as two creatorpreneurs with very nonlinear careers.

Sam’s career is more nonlinear than mine. She started her career at Cosmopolitan, worked in social media for Cynthia Rowley, built her own wellness-focused personal brand, founded a creative agency and a clothing brand, and hosts her podcast.

What I loved most about this conversation is that true to nonlinear form, we covered a LOT of ground:

• Quitting too early and what I’d do differently

• Why my chill fully-remote tech job drained me just as much as banking

• How to figure out what’s next

• How a Saturday night video I made while painting my nails that got me 50k followers and kickstarted my content business

• How to build a personal brand in 2026 when everyone’s already doing it.

If you’re on a nonlinear path, figuring out what’s next, or thinking about how to stay relevant as AI changes everything at work, I hope you’ll find this useful!

I quit my dream job without a plan…twice

Sam: How did you know you were ready to leave your dream job? Did you have a rubric, a pro-con list? Or did you just reach a breaking point?

Hannah: Definitely more of a breaking point. And I’ll be honest with you: I think I quit too early. For a long time after, I thought I made the wrong decision. I wished I had stayed a little bit longer — not because I wasn’t going to leave, but so I could have made a plan.

I’ve done this twice. The two instances where I really felt like I am not in the right place were very different from each other. Coming out of banking, that was just the hours, the toxicity, the burnout. But then last year, after I graduated business school, I was working in a high-paying, very chill, fully remote tech job. And somehow that job drained me. It drained me because I felt stuck in place. I was not growing, not learning. It felt like such dissonance because it wasn’t a burnout situation. It was the opposite.

Sam: So burnout the first time, stagnation the second. The second time, it sounds like you had something in mind for what was next, and that’s what gave you the confidence to leave.

Hannah: Yeah. And I think the readiness thing is — a lot of us, especially high achievers, we don’t listen to our instincts. But at the end of the day, you know. You really do know. You can do all the pro-con lists on paper, make all the plans, but what you really need to do is take that first step of action. And sometimes the drastic decision to quit isn’t the right action. The right action might be: what’s one small experiment I can run? Who can I talk to that will give me some clues? It’s not always just, I’m going to up and go. Because that’s going to make you feel like you failed. Financially insecure. Incompetent. There’s a lot of imposter syndrome that comes with that too.

The $250k concept I filmed while painting my nails

Sam: A lot of people take away very different things from their MBA. I’m curious if there are things you learned that you use constantly now, across multiple roles.

Hannah: Something I learned in business school is literally the entire reason I have the personal brand and content business I built today. I know that sounds crazy, but one of my earliest videos — maybe a month into creating content — completely blew up my account and got me 50,000 followers. Not even kidding.

It was about this concept in negotiation called BATNA. Best Alternative to a Negotiated Agreement. And this was one of my lowest-production videos ever. It was a Saturday night and I was painting my nails.

Sam: It’s only those that blow the whole thing open.

Hannah: Always. And I was like — I paid $250k to learn this in my MBA. BATNA is basically the idea of having a plan B and not selling yourself short in any situation. If you and I are negotiating a job offer, I have a good BATNA if I have another offer on the table. I think it resonated with people because so many of us are used to chasing rather than attracting opportunities. The whole concept of having a backup is: you always need to shore up your other options. Your full-time job — you cling to it because it’s the thing that pays your bills. But as soon as you start building something on the side and you have something else, it just completely changes your mindset. It’s the same with relationships, even with having social plans on the weekend. The principle is everywhere. I paid $250k to learn it at Wharton and made a video about it on a Saturday night.

Banking → tech → MBA: a path without a plan

Sam: So you leave banking, you travel, and when you came back, did you start in another job or go straight to Wharton?

Hannah: I had a job between traveling and Wharton. After I quit investment banking, I thought — you see stuff in the movies, right? You see Eat, Pray, Love, and you’re like, I’m going to go to Argentina. I’m going to find myself. I’m going to climb the mountains and that’s going to be great. It’s just going to all be suddenly clear. I’m going to reach some sort of epiphany and figure it out. No, of course that didn’t happen.

Being in nature did help me think more clearly. When you’re always hunched over a computer and your brain cells are getting fried, putting yourself in nature gives you some clarity. But that doesn’t mean it’s going to just inception you into the right next thing.

Honestly, I went through months of just: what am I doing with my life? I quit what might have been the best-paying job I’ll ever get. I can never go back to finance — I completely burned that bridge. What am I going to do?

So on one hand, I started figuring out the business school process, because that’s just what a lot of people do. And on the other hand, I started panic mass-applying to jobs. Hundreds of jobs that had nothing to do with one another. I’ve never shared this on the internet, but I was deciding between a startup in Latin America and a social enterprise in Southeast Asia — two completely polar opposite things, completely polar opposite lifestyles. I think there was also a video game company in the US doing strategic finance, which I knew I didn’t want.

Sam: No way.

Hannah: Three completely different timelines. It truly felt like throwing darts at the wall. And I was very lucky because the dart I threw landed me in a really interesting startup position in Mexico City where I ended up working in two or three different roles just because of how fast the company grew — not because I asked to move, just because the business needed it. I got to try a lot of different things without switching jobs and having it look bad on paper.

Sam: And then when you went to business school — was it more figuring out what you want, or more achieving something you already knew you wanted?

Hannah: More the second thing. And this is something I talk about in my content a lot: when you go into investment banking, when you go to business school, it’s for prestige, at the end of the day. I think some people have their head in the right place — they know they’re doing it for a few years because it’s going to get them somewhere they actually want to go. But for me going into banking, I just thought: I’m going to do banking, figure out whatever’s next, make a bunch of money, and get out. No real plan behind it.

For business school, I did have a sense — I wanted to pivot into product management, which I’d done a little bit in my prior role but wanted to do at a bigger company. And business school is a great way to do that. I did achieve that goal. My summer internship was in product management. And through that, I realized I didn’t want to do it.

Sam: And that’s the only way you’ll ever know.

Hannah: It’s a little embarrassing to admit after all that. But yes.

I started posting about nonlinear careers because I was embarrassed by mine

Sam: I feel this guilt and shame about my nonlinear career all the time. So it was funny watching your videos — you’re out here celebrating this thing I’ve always felt so insecure about.

Hannah: I got to be honest: the reason I first started posting about having a nonlinear career is because I felt that same embarrassment, that same imposter syndrome. It was almost a way of gaslighting myself into believing — oh, you know, this is fine. And then more strategically, rebranding myself a little bit. When you have an experience that people don’t immediately get, you have to be your own PR person.

The funny thing is, in the process of gaslighting myself, I did end up truly believing it. Because I saw the results. And because the world started changing around us.

One of my favorite books on this is Range by David Epstein. He goes through history and shows all these examples of people who, because they had experience in different fields, went on to make great inventions or discoveries because they brought something in from a different domain. His idea of the spiky generalist — someone who can do a lot of things but is quite good in one or two specific areas — that’s the sweet spot. Because it is so hard to be number one at one single thing. But if you can be great across a bunch of different things and particularly good at one or two, that’s a real edge.

And here’s what I figured out about my own path: my day job is product marketing for a technical fintech startup, which means I’m learning how to tell a story, reach an audience, and sell something. My content does the same thing. The newsletter does the same thing. The speaking does the same thing. It’s all building the marketing muscle — I want to become so good at this craft across different parts of it. On paper, it looks like my eggs are in different baskets. But it’s the same basket. These things compound.

Sam: The “jack of all trades, master of none” quote — people only ever say the first half.

Hannah: Right. The rest of the quote is that the jack of all trades is often better than the master of one. And the broader context is that the world is changing around this anyway. Fewer people are in siloed specialist roles because AI makes it easy for everyone to be both a generalist and a specialist at the same time. The more narrow and defined your role, the easier it is to automate, because it’s repeatable patterns. There are going to be more spiky generalists because the shape of work is changing.

Sam: I’m also curious about something in your content — you had this post about the risks of maximizing and optionality. You believe in nonlinear careers, but not necessarily in keeping all your options open. Why?

Hannah: I think maximizing is this idea that you’re always looking for the next best thing — the objectively best option, not what’s actually best for you. From a career perspective, it’s like: I don’t know if I should take the marketing job or the product job or apply to business school, because I can’t figure out which one is truly the best. It’s not listening to what you actually want. Whereas the nonlinear or multi-hyphenate path is more — how am I leaning into my curiosity for what’s next and building toward the next thing?

A lot of high achievers have this maximizing tendency, and at the end of the day you just have to maximize for what is good for you. Once you’ve made the decision, be happy with it and understand that you made the best decision for you, rather than trying to find the objectively best outcome.

Why every nonlinear path leads to entrepreneurship

Sam: I have a two-year threshold in every role. At two years I get restless, start looking around. And for the longest time I just beat myself up over it. I internalized it as not having discipline.

Hannah: I think what it’s really telling you is that you’re destined to be an entrepreneur. And over time, your pivots and your experiments and your iterations become smaller and smaller. Earlier on in your career it might be this massive leap — investment banking to a no-name startup in Mexico City. And now it’s like, okay, maybe I change something within my content. It can feel like a pivot in the moment, but the moves become more precise. You’re circling closer and closer to the thing you actually want to build.

I think about that with my own content journey too. I honestly doubted I would stick with it at the beginning because so many people drop off. But over time, the shifts within my content have gotten smaller and smaller. You’re not less disciplined for having the two-year itch. You’re just getting more precise about what you’re building toward.

How to be high agency

Sam: I want to know how we become that high agency person. Because for me, agency is very low on my values ranking. My authenticity gap is negative — I’m expressing too much agency. I’m sick of making all the calls. I just want someone to tell me what to do for once.

Hannah: Being high agency can be exhausting, and that might sound contradictory. But I think in order to be truly high agency, it requires knowing which parts of your life you want to dedicate that agency to. Some of that is removing decision fatigue around things that don’t truly matter. The high agency is also knowing what to prioritize. In my personal life, I honestly don’t plan a lot. I’ve got a planner at home — that’s my boyfriend.

I think the most important thing is a bias for action. You don’t sit and mull on something to the nth degree. After you have enough of a plan and enough of a strategy, you take action. But there’s a flip side — if you only ever take action without any strategy and execute poorly, that’s not high agency either. It’s more: how do you go about finding the tools and resources to get something done? The best description I’ve heard of this is the person you’d call if you were stuck in a jail cell in a random country. Who would get you out?

And I find it increasingly hard to be around low agency — you see it in the workplace where people come to you with problems instead of solutions. High agency people get things done before they’re even asked.

Sam: I think the smartest people in the room do enough research to make a decision, and then they make it the right decision — instead of secondguessing it endlessly.

Hannah: 100%. If you’re truly agonizing over a decision and both paths seem good, the one you pick will be the right path because you’re going to do everything in your power to make it the right decision.

In the context of AI, being high agency comes down to this: some people are never going to open Claude or ChatGPT until someone forces them to. Then they’ll use it like a chatbot and never take the extra step to figure out what it can actually do. That’s where the gap is going to widen — between people who learn these tools and people who just sit and wait.

Building a personal brand in 2026

Sam: How do you approach building a personal brand in 2026, with all this noise and everyone doing it?

Hannah: The first misconception is that everyone has a personal brand already. How are you perceived? What do people think about you at work, with your friends, with your family? That already exists. What we see online — the LinkedIn presence, the Instagram, the newsletter — that’s the amplification of your personal brand, not the brand itself.

And what your goal is behind building one matters a lot. If you’re pivoting into a new field and want to show how your past experience is relevant, that’s probably LinkedIn. If you just started a small jewelry business on the side and you want to drive leads to your business, Instagram — maybe TikTok — is the way to go. The tool follows the goal. Most people who say “build a personal brand” have collapsed the whole thing down to one channel without really understanding what they’re building toward.

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

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Alex McCann has never had a corporate job. He studied music. He ran a boutique marketing agency that didn’t work out. He digital nomaded across Latin America with friends who quit their jobs to come with him. And then he wrote a Substack post called “The Death of the Corporate Job” that got 17,000 likes, got picked up by The Times, and somehow led him to a call with the CEO of Bayer. Then he build an AI career platform.

None of that was his plan. His plan (if you can call it that) was to document what he was learning in real time and see what happened. After his Substackpost blew up, he did something I think is underrated (and exactly what I did before I first started creating content): he opened his calendar to strangers, took hundreds of calls over two months, and used every conversation to understand exactly what people were stuck on. That research became Rumbo, an AI career tool built around the idea that most people aren’t asking the wrong question, but answering it in the wrong vocabulary.

Alex and I connected through our career-related content, and I’ve been wanting to have this conversation for a while. So many of you are in corporate jobs that feel like they’re running out of road, and so many of you want to build something but have no idea where to start. Alex has thought about both of these things more carefully than most people I’ve spoken to.

Whether you’re thinking about your next career move, figuring out your next creative direction, or building your own product, I think you’ll get a lot from our conversation.

From engineering to music to founder: the long way around

Hannah: You’ve made so many pivots: engineering to music to creative director to now founder and content creator. A lot of my audience has been in the same job for years while you’ve done all of that. How did you get clarity on what the next step was every time? And how did you get the confidence to actually go do it?

Alex: It was a combination of things. I really believe in this idea from the book Tiny Experiments, just trying things out. That was something I didn’t realize was a skill, but I had always just been somebody who would give stuff a go. And that coupled with a really intense curiosity, just asking a lot of questions of myself and other people. I think that was what allowed me to pivot quickly.

I also have to acknowledge that I was young and didn’t have any responsibility, so I could take on a lot of risk. But the culmination of voracious curiosity, willingness to try things, a kind of attitude of I’m just going to try stuff and then see what happens, and circumstances that allowed that to happen. It was a combination of luck and people around me encouraging that curiosity.

Hannah: Did you ever fear that by switching from engineering to music, or music to creative, you were throwing away all the work you’d done previously?

Alex: Yes, a little. I never got so into it that there were too many sunk costs. The biggest shift was definitely the move from engineering to music, because up until that point my whole life I had really identified as an academic person who loves this type of thing. I had crafted my identity around what I thought I was going to be. And then when it all came crashing down, there was a real identity shift. That was hard.

I was pretty early on clued into the idea that qualifications were less valuable than they used to be, and the corporate ladder wasn’t what it used to be. So the sunk cost piece was less of it. But I definitely felt the weight of the identity changes that came with the pivots.

Building the content muscle before anything went viral

Hannah: You said several times that you were really lucky. And I’m sure you feel that way, and you’re a humble person. But luck only shows up when you’ve done the work to maximize your surface area of luck. Every piece of content you post is a lottery ticket. How did you first start creating content? What was your initial goal with it?

Alex: I want to give myself credit for two things. One is the beginner’s mindset. When I started my first business, I went to a lot of networking events and I was often the youngest person in the room by a lot. The mistake a lot of young people make is going into those rooms trying to show what they know. I didn’t have that. I went in with an attitude of: you’re the expert, I’m the beginner, can I just ask you questions? That gave me access to people who ended up being mentors because they were interested in helping someone who was genuinely curious rather than performing confidence.

And the second thing: opportunity is a function of density. When you’re young, one of the best things you can do is just put yourself out there in whatever form that is. Networking events, content, reaching out to hundreds of people every week.

How I got into content: that graduate job I mentioned introduced me to personal branding because I was doing some LinkedIn posts for the founder. An early mentor said to me, you’re in a really steep learning curve right now, why don’t you just share what you’re learning and see what happens? So that’s what I did. And I started to get some traction. Nothing like now, but it helped me build the muscle.

Then I stopped for a while while I was traveling and working a previous role. And when I started this new venture, it felt like second nature. I thought, okay, there are interesting things I’m learning, interesting things I’m seeing, let me just put it out there. My coach was also on Substack and said it’s a good place for a slightly different style than LinkedIn. So I did. And yeah, rest is history.

Hannah: I love that you were documenting your learnings in real time. That’s the thing people don’t say out loud: most people who build a personal brand, it’s not their full-time job. The best approach is to document what you’re already doing, so it doesn’t feel like every post is a fresh thing you have to invent from scratch.

Alex: It’s like what they say about musicians. In the early stages, their work is the best because their proximity to real life makes it relatable. And then as they get successful, that proximity disappears and people stop connecting with it as much. When people are really in the thick of something, building a product, learning from a day job, it’s stuff people can relate to. It feels more authentic. And I can imagine that when your whole job becomes content creation, it gets harder to maintain that.

The viral Substack post and the CEO of Bayer in his DMs

Hannah: Your Substack post “The Death of the Corporate Job” had 17,000 likes. I usually get 50 likes on my posts. What was the core idea, and why do you think it resonated the way it did?

Alex: It came from reading Moral Ambition, which I highly recommend. The author talks about this idea that so many highly ambitious, highly intelligent people end up in what he calls bullshit jobs, this Bermuda Triangle of meaninglessness: corporate finance, banking, corporate law. And I remember reading that and seeing the people around me in my life who were so intelligent, so ambitious, great university degrees, genuinely kind and generous people, and yet the system had incentivized this particular kind of work, and the corporate ladder was still being sold as this glamorous journey.

I just thought there was something so different between the narrative around corporate work in media, from our parents’ generation, and the people actually living it. I wanted to uncover that and be honest about it. Why is the system set up to reward something that is so clearly not what it’s perceived to be? And what does the future look like? Because part of what I was writing about is that this understanding of the corporate ladder is changing anyway. It may not even be on offer to people who are interested in that path.

Hannah: And you’ve never had a corporate job. How do you think about those two things being true at the same time?

Alex: Totally get it from the people who’ve criticized me for that. Two things are worth saying. First, I was hearing this from so many people, so many conversations all coming to the same conclusion. I was prepared to be wrong. But the response felt like proof of concept, because so many people put their hands up and said yes, this is true to my experience.

The second thing is the fish in water observation. People who are inside the corporate machine get so heads-down, engrossed in the culture and the language, there’s this whole corporate vernacular, that sometimes it takes someone from outside to point out something that’s actually pretty obvious to the people in it. I was hearing a lot of the same thing from a lot of different people, and I thought: let me just put my observations out and see what they think.

Hannah: What was the craziest thing that happened as a result?

Alex: The press coverage was wild. The Times did a roundup of articles to read in 2025 and it was one of the top ones. The Free Press feature the same weekend they were acquired blew up too. But the craziest one was the CEO of Bayer reaching out.

This person messaged me on Substack with no profile picture, no context, said their CEO wanted to chat if I was interested in interviewing him. I was pretty doe-eyed about the whole thing at that point, said sure, put it in the calendar a few weeks ahead, and forgot about it. Then the weekend before, I’m looking at my calendar and I see this interview pop up. I looked it up. Bill Anderson. CEO of a company with nearly 100,000 employees, one of the biggest pharmaceutical companies in the world. And I had just casually booked it like it was nothing.

But honestly? The craziest thing is being at events now and having people I’ve never met turn to me and say, oh yeah, I’ve read your article. That still blows my mind.

How he turned 17,000 likes into hundreds of 1:1 calls and (eventually) a product

Hannah: You didn’t just double down on Substack after the post blew up. You had a really intentional approach to figuring out what to actually do next. Walk me through that.

Alex: When the article went viral, I knew we were going to build the platform, but it was really early stages. I didn’t know exactly who it was for or what it might look like. I asked myself: since I’m not the one building it, what’s the most impactful thing I can do? And I thought: understand the problem from every possible angle.

So I put out a link to my calendar and said, if anyone wants to chat, just book some time. I’m not a career coach, I’m happy to just be a sounding board. And it went crazy. Hundreds and hundreds of people booked calls over the next couple of months.

One of the things that kept coming up was that people had started using ChatGPT to help them think through their careers, but they were still lost. ChatGPT as a conversational partner can only respond to the quality of input you give it. And if you don’t have a clear understanding of what is likely to bring you career fulfillment and meaning, the results you get back are going to be pretty limited. So that was really interesting to me: people are open to exploring this with AI, but it’s not quite there, it’s missing something. And that’s where we landed on the idea for Rumbo.

Alex’s advice: Stop seeing your career as your CV

Hannah: Last question. For someone in a corporate job who feels like it’s slowly dying, but the paycheck is real and they feel stuck, what’s your number one piece of advice?

Alex: The number one problem I see is that people think about themselves through the lens of their CV. When I ask people who come to me in that situation what they’re good at, they answer in CV language. I’m really good with Excel. I can present PowerPoints in a meeting. And my advice is to try and get yourself out of that way of thinking and look below the surface.

What is the skill behind your ability to use Excel? Maybe it’s analytical skills or being a really organized person.

What is the skill behind being good at presentations? That’s communication, making sense of complex ideas, storytelling.

When you start thinking about the foundational skill beneath the things you’re doing day to day, it allows you to think much more broadly about where you could apply those things. Things end up being a lot more transferable than you might expect.

Subscribe to Alex’s Substack and follow his journey building Rumbo!

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