How a non-traditional career path built my GTM models

I.

When I was at BYU, Former Secretary of State Condoleezza Rice came and spoke at one of my school's weekly forums. She told us that she had a childhood dream of being a concert pianist, but began to be shaken from this path when at 17 she went to the Aspen Music Festival and saw 12-year olds sight-reading pieces that had taken her a whole year to learn. Eventually in college, she took a course from Madeleine Albright's father, Josef Korbel, on international politics, which began her passion for Soviet and Russian studies. I recall her saying that at one point she was weighing whether to purse graduate studies in piano or political science, and she ultimately chose a PhD in political science.

For years she would feel the pangs of her slipping piano skills, and she took up chamber music to fill some of that gap. She said it wasn't until she was getting into a helicopter with Mikhail Gorbachev years later that she knew she had made the right choice. And she said that her diplomatic and political career eventually led to opportunities to play with Yo-Yo Ma at Carnegie Hall and Queen Elizabeth somewhere fancy – opportunities she didn't believe her musical merits alone would have provided her. So in the end she went further in her musical career because of her decision to pursue her political career. I recall there being some take home lesson about choosing to pursue a career where you can excel can afford you opportunities to do more of the things you love.

I played the violin growing up and had similar aspirations as Ms. Rice, and also eventually decided to pursue something else. I didn't know exactly what it was I was pursuing until in 2024 I realized I had become a GTM generalist. Let me tell you about that journey.

II.

Once upon a time I was a very precocious child. Or, at least, once upon a time my mother recognized that I was the sort of kid who became restless during summer vacation and needed some mental exercise. She decided to make me do math and science and reading packets before I could go and play in between grades. This became a sort of painful wax-on, wax-off experience that, much like the Karate Kid, unknowingly increased my grade-level despite my tweenaged protests. As a result, I moved very quickly through elementary school, eventually jumping from 4th grade to 7th grade in one year.

Everyone, my mother paramount among them (I love you), told me I was smart, and that created inordinate pressure internally to excel. Skipping grades brings social integration challenges, especially because I was late to growth spurt and had (have?) a baby face and was all around a late bloomer. When Freshman year of high school started, I was the shortest kid in high school, and everyone decided to call me Big Mike. I was aware enough to recognize that I had a lot of work to do to catch up to everyone else's extra years of prefrontal cortex and physical development.

The pressure led to me feeling a need to keep moving quickly, and by the time I graduated from BYU, I had just turned 19. The thing is, I had moved so quickly, with laser focus on my degree (international relations), and with no internships etc., that I truly had no idea how the world worked, at all. Though I was gregarious and generally extroverted I remained awkward and in need of socialization, though time at BYU had compensated for my deficiencies to some extent.

III.

Just as I was beginning to ponder my place in the world and also realize how little I knew, I shipped out to Taiwan for a two-year proselytizing mission for my church (if you know you know). Every day, I woke up at 6:30am. Like, literally every day. I think I missed two days my whole mission, on the very first day and once when I was sick. Every evening, I retired at 10:30pm. I did not watch TV or movies, casually hang out with friends, go on dates (or even think about that). I would wake up, put on a white shirt and black name tag, get on my bike, and go talk to people.

It's obvious in retrospect, but the mission (that's what we call it, "the mission") is also a wax-on, wax-off experience, but for socialization. I once estimated that over those two years, I probably spoke with upwards of 20,000 people. In Mandarin Chinese. About religion, and life. It was boot camp for going over and talking to people. I sometimes joke (to myself, quietly in my mind, an inside joke with myself) that before I ever did go-to-market, I first did go-to-mission.

The mission plays very deeply into my understanding of how GTM works. Every Thursday, my assigned compatriot and I would sit down and plan the coming week for a few hours. We would review goals, and our plans to achieve those goals. We would discuss ways to improve the quantity and quality of our efforts. We would discuss ways to improve the quality of our collaboration, the culture of our small workspace. We would discuss people, and what they needed, and how we could help them. Then daily in the evening, we would plan for the day ahead, always in reference to the weekly plan. Each morning, we would engage in person, team, and then language study, and would roleplay encounters and lessons to teach. And then each day, we would go out into the world and let it rip.

I think across all GTM work I've ever done, I've basically been doing some version of the above. I learned to think in bets and push on execution before I ever heard those phrases or knew what they meant.

IV.

Let me speedrun you through the next few years: I returned home, was a summer sales bro knocking on doors selling pest control in Dallas (207 closed won accounts!), went to grad school studying economics, started and stalled a bio-charcoal business in Kenya, spent time at the World Bank, finally got my first "real" job doing infrastructure finance at Deloitte, and after two years there moved to SF to join a random startup working on business development and strategy (a GTM role before we called it GTM).

That first startup I joined struggled to find its footing, and I started to feel like I had thrown my career away naively joining a company and working in an industry I didn't understand. Interviews at large companies like Uber and LinkedIn weren't going past the first round, and I fell into a funk, wondering how my precocious self had ended up here. Further, I was saddled by thinking that my younger self was disappointed that by my mid-twenties I hadn't already cured cancer.

V.

Then I got my first lesson in "wide context prepares you for unique experiences". I received a recruiting outreach from a founder wanting to build a private credit marketplace (Hum Capital). He was particularly interested in my combination of consulting, infrastructure and project finance, and sales experience. And I later found out that they were looking specifically for Latter-day Saints who had served missions, though they themselves self-identified as heathens aha.

It turned out, my weird combination of experiences made me spike in the perfect way for the originations role they were looking for. So I joined, and spent the next three years talking to over 2,000 founders about their respective businesses and balance sheet needs. I had literally thousands of reps talking to the C-suite about their businesses, learning how to ask the right questions to reveal what was really going on, while simultaneously trying to court them to seek capital from our network. I also ran my first early days GTM email cold outbound. Nothing like an email subject line of "Offering [company name] $5M-$50M in flexible financing" in the pre spam clamp down era of email to get reply rates up into the stratosphere. It was a street smarts crash course and master class in finance, capital allocation, GTM, and quickly learning the surface area and probing for ground truths in a business.

As an aside, nothing like talking to so many CEOs seeking capital to invite disillusionment about ever starting a business. And yet… I did… almost to that part.

VI.

My time at Hum was coming to a close and I was in pursuit of something intense. Serendipitously, I received an outreach from a recruiter at Clipboard Health for a role on the revenue strategy team. As I diligenced the company, I learned they were built to run like Amazon, with weekly business review run in silence and a culture of writing. I was in. After a few months, I was promoted into Clipboard's GTM new verticals team. This was the team that built new multimillion dollar businesses on top of, or if it survived scrutiny, adjacent to Clipboard's per-diem marketplace platform. Joining this group felt like an invitation to the Green Berets. (I have no idea what the Green Berets is like, but neither do you so I'm keeping the metaphor.) Weekly business reviews were high-dopamine, high-cortisol skewerings of my thinking, planning, speed of execution, rate of learning, and results. I was fortunate to be on a team of people each building a business, in a vat of high standards and the expectation of extreme ownership and creativity.

Crazy to say because this was only 2-3 years ago, but this was GTM on manual mode. For the 18 months I was in that seat, we grew the vertical (hospitals and health systems) about 5x from baseline into Clipboard's second largest vertical, and we didn't really have any AI to support. It was just me, Metabase, the team, the market, and our prospects. We (a team effort!) pulled this off by running, I don't know, probably ~25 bets or experiments, making sometimes one-way door judgment calls on what to prioritize and deprioritize. It was a whirlwind.

A restlessness drove me to leave Clipboard and venture out on my own to eventually start Apero. In hindsight, I think I felt bounded by only being able to work on a relatively small range of problems in a single market. And I realized that, if I was working at such an excellent company as Clipboard and still wanted out, that probably meant it was time to take a risk. And so here you find me, typing away at Ben's insistence to build domain authority and tell Apero's story.

It was a long and winding road of building context talking to tens of thousands of people, and working with literally thousands of businesses, that I believe has given me the probing skills and the pattern-recognition to paratroop into a b2b business and quickly build a mental map of how to help it scale, or at least the sequence of bets to run to run towards that answer. That's the sort of work we do everyday, and it's really fun.

In the end, I'm glad I didn't stick with the violin. But I still hope this orthogonal career lands me someday in Carnegie Hall playing the violin alongside my favorite mandolinist, Chris Thile