💼 How to turn what you know into a business outside your 9-5: The steps I’d take if I were starting over, from finding an idea to testing your first paid offer—with the prompts, customer questions, and templates to follow along.
In 2022, I got rejected from Y Combinator.
Soon after, I tried starting an MBA admissions consulting business. I built a website, registered a domain, and wrote out an entire list of ideas for TikTok videos that I never posted.
In business school at Wharton, I joined the entrepreneurship club and worked alongside startups, but when it came to starting something myself, I told myself I didn’t have the time, the idea, the resources, or the motivation.
Looking back, the bottleneck was never time or resources.
It was an ingrained, rigid idea of what entrepreneurship had to look like. You came up with a $1Bn tech idea, built software, found a co-founder, pitched venture capitalists, raised institutional money, and quit your job to go all in. I was surrounded by that version of it, and I couldn’t see where I fit.
A lot of you reading this might be sitting in that exact same loop:
You want to build a business, but raising venture money and running a venture-backed startup sounds like an exhausting, high-risk life you didn’t sign up for.
You’ve built 5 to 10 years of skills at work in product, finance, marketing, or ops, but you can’t picture what someone would buy from you independently.
You have several half-formed ideas, maybe some shiny object syndrome, and no clue which one deserves your scarce time on evenings and weekends.
You keep hearing that you need a personal brand, but you don’t want a second unpaid job dancing on video or chasing aesthetic trends every day with no clear plan for monetizing it all.
In 2024, I started on a very different path: building an asset outside my 9-5 around what I already knew, using content to build distribution first and discover what people would actually pay for, monetizing across an ecosystem rather just one single income stream.
Here’s what that model has actually generated for me over the past two years:
Content that converted into multi-five-figure brand partnerships with major tech companies.
A marketing funnel for digital products and toolkits
High-ticket 1-on-1 advisory clients and group coaching
In-person events (like my 5-to-9 Builders Club in NYC, which had over 700 signups for our most recent meetup) that double as community feedback and new sponsorship surfaces.
Paid speaking engagements.
Prototyping and launching lightweight software apps (that I’ve mostly used as lead magnets, but can be expanded out and monetized as well)
A newsletter that’s landed me sponsorships and paid subscribers
And the one I least expected…I still get incoming job offers from companies that want to hire me full time! Not in spite of my business but because of it.
There’s no single fixed template you have to follow. You don’t need to build all of these at once, and you shouldn’t try to. But building an asset around your existing expertise gives you options that a single W-2 salary never will.
People often refer to this as a “side hustle.” It’s fine if calling it a side hustle helps you take the first small step without feeling intimidated. It’s what I did at first. But long term, treating it as a side hustle keeps your thinking small. A side hustle is something you tinker with on weekends. A 5-to-9 business is an asset designed from day one to compound your reputation, ownership, and income.
Building this kind of business has transformed my career and life. So I’ve brain dumped everything I’ve learned over the last two years into the steps I’d follow if I had to start over again from scratch, with exact templates for things like customer discovery surveys, landing page and lead magnet creation.
In the full guide below:
Quick shortcut: Take this whole post, paste it into ChatGPT or Claude, and ask it to walk you through step by step!
Phase 1: The experience-to-value inventory: How to uncover the expertise you overlook because it feels ordinary to you, plus the 6 places to look beyond your work resume.
Phase 2: Customer discovery before content: The 8-question interview script and the exact survey template I use to find what people will pay for.
Phase 3: The content discovery engine: How to turn interview answers into your first posts without designing a 30-day content calendar.
Phase 4: Your first lead magnet sprint: How to build a high-value free guide, set up the signup page, and write the follow-up emails that capture demand.
Phase 5: The complete offer framework: How to design, structure, and price your first paid offer (with 5 ideas)
Phase 6: The 4-bucket monetization architecture: How brand deals fit in, the media business model, and how income streams compound into an ecosystem.
Phase 7: Running the system in your 5-9: A weekly calendar sprint, employer boundary checks, and growing the asset.
👥💬 Subscribe for real interviews with five 5-9 builders
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📅 Join my in-person event with Microsoft on November 18!
A LOT of you are building while growing your careers in corporate, which I’m such an advocate for! Ahead of performance review season we’re locking in and using Copilot to build a case for building your ~internal~ brand. Apply