The Anti-Portfolio of Investments Not Made

The other day I listed some of the things I got wrong. I’m not the only one to have made some bad calls. A friend who works for  the VC investment firm Bessemer Venture Partners (BVP) pointed me to their very honest and amusing disclosure of opportunities they missed. The site says directly:

Bessemer Venture Partners is perhaps the nation’s oldest venture capital firm, carrying on an unbroken practice of venture capital investing that stretches back to 1911. This long and storied history has afforded our firm an unparalleled number of opportunities to completely screw up.

A few examples:

Cowan’s [one of the partners] college friend rented her garage to Sergey and Larry for their first year. In 1999 and 2000 she tried to introduce Cowan to “these two really smart Stanford students writing a search engine”. Students? A new search engine? In the most important moment ever for Bessemer’s anti-portfolio, Cowan asked her, “How can I get out of this house without going anywhere near your garage?”

“Stamps? Coins? Comic books? You’ve GOT to be kidding,” thought Cowan. “No-brainer pass.”

BVP had the opportunity to invest in pre-IPO secondary stock in Apple at a $60M valuation. BVP’s Neill Brownstein called it “outrageously expensive.”

Incredibly, BVP passed on Federal Express seven times.

David Cowan passed on the Series A round. Rookie team, regulatory nightmare. 4 years later, a $1.5 billion acquisition by eBay.

If you think about it, most VC firms must have equally long and entertaining lists, even if they don’t publish them. Turning down startups is what VCs do — most of the time.