Representative Angel Investments

Update August 2017

Here’s a 90% complete list of investments, good and bad, done to date, organized below in 3 sections: funds, direct investments, and investments from AngelList syndicates.

Current status: have slowed down my direct angel investing. Currently looking at investments in funds where I believe there is a built-in “unfair advantage”. Like the Bio-Innovation Fund, which backs select companies they work besides daily in their co-working space where they rent wet labs for basic science, and The Engine, which builds on their insider role backing promising technology out of MIT. I hope to add value via my network and experience, but frankly don’t have a lot of time to dig in deeply after my initial help making intros and connections to customers, advisors and other investors. Right now, I prefer to invest in either Ether or Bitcoin, betting on the overall success of their protocols rather than on any one specific team. And it’s liquid. I’ve got a program on Coinbase to buy some ETH and BTC every 2 weeks. ETH is my biggest single investment other than the public Vanguard funds which are the foundation of my investmest strategy. I think at this point my “alternative” investments are about 1/3rd of my portfolio. The intention was smaller, but I just rolled old ones into new ones. I’ve always intended it to be 20%, but then crypto assets exploded.

Some stats: 12 commingled funds; 80 direct deals; 65 syndicated deals via AngelList.  I broke down the stats earlier this year for an AMA on Growthhacker.com.
Just over ½ of the companies I’ve invested in directly (not including managed funds, limited partnerships, etc.) are in MA, which isn’t surprising since that is where my network is deepest. 15% are from CA, 13% from NY, 8% international, and the rest random across the United States.

Only 8% had female CEOs, and only 17% even had a female co-founder on the team. (Fortunately, the quantity and quality of female-led teams is improving, as 6 of the 13 teams in the new Techstars Boston class have female CEOs.)

14% of the founders I never met in person before making the investments—half of those I talked to via videoconference beforehand, and the other half was me simply going along blind with trusted friends who were investing and had done the diligence.

About 2/3rds of the teams were led by first time CEOs, but almost every team had either deep domain expertise or significant relevant prior business experience. I’m guessing—no stats here—about 10% of the CEOs were 25 or under, and 80% between 25 and 40 years old. This in spite of me not starting my first company until I was 45. About 1/3rd of my investments come out of places where I mentor (Techstars, Harvard, MIT, MassChallenge), and the majority come to me recommended from either trusted co-investors or previous portfolio companies.

A LOT of investments (including my best 3 investments) came with a founder with a compelling immigrant story and incredible work ethic. It’s certainly higher than the population at large.