Bessemer Venture Partners, one of the oldest venture-capital firms in the United States, had a big score when it led the private financing of Shopify from 2010 through to the IPO in 2015.
But it has missed other big scores over the years, and to remind itself to “try harder,” the firm has created an Anti-Portfolio containing the big ones that it missed. Here is most of the Bessemer Anti-Portfolio, with commentary in their own words.
Apple
Bessemer had the opportunity to invest in pre-IPO secondary stock in Apple at a $60M valuation. Neill Brownstein called it "outrageously expensive."
eBay
"Stamps? Coins? Comic books? You've GOT to be kidding," thought David Cowan. "No-brainer pass
Jeremy Levine spent a weekend at a corporate retreat in the summer of 2004 dodging persistent Harvard undergrad Eduardo Saverin's rabid pitch. Finally, cornered in a lunch line, Jeremy delivered some sage advice, "Kid, haven't you heard of Friendster? Move on. It's over!"
FedEx
Incredibly, Bessemer passed on Federal Express 7 times.
David Cowan’s 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?”
Intel
Pete Bancroft never quite settled on terms with Bob Noyce, who instead took venture financing from a guy named Arthur Rock.
Intuit
Along with every venture capitalist on Sand Hill Road, Neill Brownstein turned down Intuit founder Scott Cook. Scott managed to scrape together only $225K from friends, including HBS classmate and Sierra Ventures founder Peter Wendell, who personally invested $25K to get Scott off his back.
PayPal
David Cowan passed on the Series A round. Rookie team, regulatory nightmare, and, 4 years later, a $1.5 billion acquisition by eBay.
Snapchat
In 2011 Jeremy Levine arrived at LAX three hours late, thanks to flight delays, with enough time for only one of the two meetings on his calendar. He literally tossed a quarter and phoned Evan Spiegel with his regrets. SNAP was the largest IPO in 2017
Tesla
In 2006 Byron Deeter met the team and test-drove a roadster. He put a deposit on the car, but passed on the negative margin company telling his partners, "It's a win-win. I get a great car and some other VC pays for it!" The company passed $30B in market cap in 2014. Byron paid full price for his Model X.
Zoom
After trying several next-gen video conferencing products, it was clear to Alex Ferrara that Zoom was a winner. Most importantly, he was impressed by its engineer-turned-founder, Eric Yuan. But video conferencing was crowded with entrenched incumbents and multiple startups in the market, so Alex passed on Zoom’s series B in 2014. Better late than never, we invested in Zoom’s IPO at a $9 billion valuation.
Bessemer’s past winners and current picks
For some of Bessemer’s past winners and current investments see Our Companies.
What would your Anti-Portfolio look like?
Of course, most investors reading the financial press and blogs are investing in stocks on public exchanges, not private equities like Bessemer. Still, the anti-portfolio concept should still be easily transferable to publicly traded stock.