Investment Strategy

Aspiring to be the Leeroy Jenkins of angels, I like to lean in early with conviction as a catalyzing backer of bold visions put forth by outlier founders in disruptible legacy or pre-inflection emerging markets. I invest in people first and partner as a relentless advocate with startup founders on epic journeys to change the world.

I made my first angel investment in 1998 as a young tech investment banker –, a full stack online pharmacy well ahead of its time. It quickly went bankrupt after the Internet bubble burst; however, my passion for the intersection of technology and investment was indelibly etched in my psyche. Much like a machine learning algorithm, I have sharpened my approach over the years by crunching hundreds, if not thousands, of startup data sets with constant investment experimentation, many failures, and a handful of glowing successes.

My Investment Criteria:

1.  Play the Power Law – Earlier investments will have higher risk/reward, and portfolio variance shrinks as the fund diversifies into more investments. I am highly selective, but I have intentionally built a broad portfolio. Startups are highly unpredictable, and time and again, my early high-flyers have crashed and my stragglers have iterated their way to a breakout. I believe in backing outlier founders at reasonable entry points across a wide spectrum of business models at the edge of innovation. “Venture capital is not even a home run business. It’s a grand slam business.”

2.  Founder/Market Fit – These founders are typically not seeking returns or are serial entrepreneurs; rather, they are truly passionate about solving the most challenging problems in large markets by applying unique insights. I judge founders on the content of their character and on their passion for the mission.  Why are you uniquely suited to solve this problem at this time? And, why should I care about this problem?

3.  Contrarian – I seek outlier founders with unique insights that few can see.  They are contrarian not because they oppose the mainstream view, but because they are myopically focused on their independent vision. They anticipate a new world and proactively build to that future to solve large problems. Typically, I can’t “see” their vision initially, but I am drawn to their conviction and narrative in a profound way as I dive in.

4.  Monopoly – I look for “zero to one” opportunities and only invest in companies that I believe have the potential to return my whole fund generating 1000x returns – the very elusive Thunder Lizards. Disrupting a legacy market, establishing a beachhead pre-inflection in an emerging market, or adding a unique feature to an existing business model that ignites a stagnant market. These businesses don’t try to be “better than”; rather, they focus on “different” with proprietary power leveraging technology, network effects, or design implementation. The best paths are new and untried.

Late Stage Strategy

In addition to seed investing, I sometimes invest in mid-to-late stage rounds either as an LP in SPVs run by VC or angel friends or by purchasing direct shares on the secondary market. These investments are highly opportunistic and serve to lower the liquidity duration of my portfolio.

The strategy here is closely aligned with my seed strategy. Seek a diverse subset of truly foundational companies that show strong signals of being the market leaders of tomorrow. Many of these companies will still fail, even after being significantly derisked at the time I enter my position. However, I believe that these investments still offer 100x return potential upon investment, and are often securing beachheads at pre-inflection points in massive emerging markets.