Back in 2011 I wrote a post titled “Startup Investment Portfolio Game” where I started a list of “companies I would invest in if I could” to look back on in the future. This post is intended show how the startup investment picks list would have done as a venture capital portfolio as well as provide a few observations and learnings looking back on everything.
The initial list contained 37 startups, and over the last 6 years I’ve been periodically adding companies to the list that I like, bringing the total to 144 startups today. The Wayback Machine has been taking snapshots of this list over time , which should help verify the dates that the companies were picked and that I haven’t changed anything (not perfect, but good enough). The results exclude companies added in the past 2 years as they haven’t had enough time to materially change in value, but I’ll highli
It is not a straight forward process to quantify the performance of a list of privately held companies. Even investors that do this for real have a hard time with valuing a private company portfolio , and they have full disclosure into all the terms and financials of the rounds and companies they invest in. Each approach and methodology has several flaws, and I’ll attempt to outline the tradeoffs with my own for this at the end – there are a LOT here. It’s clearly easier to settle on the “right investment a