Angel Investing Since College:

The Longest-Running Scientific Study in My Career

In 2018, I started writing angel checks while I was still in college. The capital came from a small handful of sources that I think most early angels would recognize: savings from part-time work during the semesters, returns I was lucky enough to compound in the public markets, and the kind of frugality that college life happens to enforce. And the deals came from founders with whom I built genuine relationships over time, rather than from screened deal flow shared across a network I did not yet have.

The checks were thesis-driven, of course, but if I am honest with myself, it was driven more than anything by the desire to be part of a mission I believed in. I would meet someone whose work I was inspired by, spend long enough time to form a real understanding about how their mind worked and where their vision was headed, and then write a check that was meaningful in a way I was honest about. At the time, it really meant a lot to me for a founder to trust a student whose only assets were passion, the willingness to be a sounding board on anything, and personal conviction. It still means a lot, every time.

What that period gave me, beyond the dealflow exposure, was an unusually long runway to learn the craft of investing. Over the years, I got to be wrong about things in ways that made the lessons stick, and I got to be right about things in ways that taught me, slowly, the difference between real personal conviction and enthusiasm — a distinction that I would argue is essential for an early-stage investor to learn, and one that is genuinely understood only by doing it.

Angel investing, in retrospect, felt to me much like a long-running scientific study: variables are considered, a hypothesis is constructed, the necessary experiments are run in the market, and we wait (often for many years) to discover where the thesis had been correct, where it had been off, and which variables we had failed to account for initially. And it is often between trial and error during the Company’s journey that the most unexpected discoveries are made. Coming from a background in fundamental research, perhaps my inclination toward complex problems is innate, but I have come to believe that this is exactly where the most interesting work in venture capital happens.

The companies below are some of the ones I am able to write publicly about today. A common thread across all of them still resonates with me today: these are companies bringing fundamental technological improvements to complex industries, where I believe the upside of getting the technology right will lead to a tangible improvement in how some foundational system in our world functions.

That early-formed thesis has, for me, only grown more relevant in the AI era. On vertical AI specifically, my view is that thin wrappers will not last; the durable value will accrue to companies that take on genuinely complex industry workflows, either by building a real, useful data moat and back-end knowledge graphs that compound over time, or because the workflow itself is intricate enough that abstracting it from real usage loops is valuable in its own right.

Each of the companies below speaks, in one way or another, to three core theses that have organized my work for years: AI and data infrastructure, the built world and physical infrastructure, and vertical AI for genuinely complex industries.

If there is a single lesson I have learned across these companies and many others, it is that venture capital is ultimately a study of people.

The work often presents itself as a discipline of analysis, which is definitely true. We build theses, evaluate markets, compare outcomes, and construct frameworks to improve our odds of being right. In many ways, it resembles a long-running scientific study: variables are identified, hypotheses are formed, experiments are run, and years later the results reveal which assumptions held and which did not.

But unlike a controlled scientific study, the variables themselves are not static. Founders grow. Markets shift. Entire industries could emerge that did not exist when the investment was first made. I came to learn that the most important discoveries are rarely the ones that appear in the original hypothesis. 

Looking back, I remember very little of the spreadsheets or growth metrics. I remember the conversations. I remember meeting founders and watching them spend years trying to turn conviction into reality. I remember the difficult periods, the pivots, the near misses, and the moments when persistence quietly compounded into something special.

When I began angel investing in college, I thought I was investing in ideas. What I have come to realize is that I was investing in people: the ideas and the companies, at their core, are human: small groups of like-minded people working hard together toward a shared mission, tested against the world as it actually is.

That is what has made angel investing one of the most meaningful parts of my career. The outcomes matter, of course. But years later, what remains are the relationships, the lessons, and the shared belief that something difficult and worthwhile was being built.

I came to many of these founders as a student with little more than personal conviction and a willingness to help however I could. They trusted me anyway. For that trust, and for everything they taught me along the way, I will always be grateful.

Eight years on, my study is still running. Some hypotheses proved to be right, others incorrect. Many are still incomplete. The variables changed, the markets evolved, and the outcomes often surprised me. But the most important conclusion has remained remarkably consistent: extraordinary companies are still built by extraordinary people. 

— HJ