The low-status, high-income AI opportunity
Why an ex Big 4 and Booth MBA grad left tech to help SMBs adopt AI
Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.
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).
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Had such a fun timing chatting all things non linear with you! Finding my WHY is the biggest unlock to navigating this path. Nothing more motivating than thinking about what I don’t want to regret when I’m older :)