I am an angel investor in around 90+ Companies, including Checkr, Wag, Womply, Notion, Caviar (acquired by Square), Origin, Wit.Ai (acquired by Facebook), etc.... My goal has been to be one of their most helpful investor, and while I have not accomplished this 100% of times, most of my portfolio Company founders could agree that I have accomplished this goal. This has allowed me to get pro-rata or super pro-rata in many of my portfolio Companies as they grew - and learn a lot along the way.
My 45 first investments came out of my personal "fund", while the following 45 were made via a few angel funds raised on angel list.
I already returned 100% of my invested capital on my personal investments, with quite a few very promising Companies still in play (Checkr, Wag, Womply, Origin, Siren, 7Cups, Headout, Notion) with valuations in the 9 digits range. Follow ups have come from investors such as: Accel, A16z, August, Data collective, DCM, Floodgate, Foundation Capital, Founders Fund, Google Ventures, Greylock, GGV, Khosla, Social+Capital, USV, etc...
I invest in Companies that can build network effects - whether we are talking about marketplaces, OSes, aggregators, data Companies, or platforms. Over time, I have over-indexed in several categories, like local commerce and on-demand, advanced manufacturing and 3D printing, new media, vertical AI software, crypto finance, real estate tech, but I am always open to new themes or ideas and bold ideas.
Anyone considering an investment in one of my syndicates should understand that these investments represent absolute risk, and there is a meaningful risk that they can lose all their money. There is no guarantee of a "soft landing" or acquisition if things do not go as planned, especially at the stage we are investing. In addition, there is no guarantee that, even in a successful company, there will be opportunity for liquidity for the shares represented and an investor should be prepared to have their capital committed for ten or more years without liquidity.
Investments in this syndicate come from three main sources:
- Pro-rata or super pro-rata of past investments in my angel and fund portfolio (typically Series A, B, or C)
- Larger allocation I am taking in pre-seed and seed investments I am making out of my angel fund.