Dear SaaStr: What Is The Worst Investment You Ever Made as a Venture Capitalist?
For years, I hadn’t lost any money on VC investments. But lemons ripened after the Great Boom of 2021, and now I have 4 investments of > $1m where I’ve lost almost all the money. There may be a few others.
The common threads: ethical lapses, lack of 200% commitment in the founders, and/or similar issues in the CEO.
If the CEO is 1000% committed and treats everyone fairly and well, and is truly great — those ones I haven’t lost money on yet. Sometimes, the gain has been modest. But I’ve never lost money there.
