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.

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