The Best Page on the Internet Is a List of Billion-Dollar Mistakes
Bessemer publishes every legendary company it passed on. It's funnier and smarter than it looks.
In 1999, a venture capitalist named David Cowan was at a friend’s house. She mentioned she’d rented out her garage to two really smart Stanford students who were building a search engine, and offered to introduce him. Cowan’s actual response: “How can I get out of this house without going anywhere near your garage?”
The students were Larry Page and Sergey Brin. And here’s the part that gets me: I didn’t dig that quote out of some deposition. Cowan’s own firm published it. It’s on their website right now, under a heading that honors the greatest companies they ever said no to.
I’ve been teaching entrepreneurship at Cornell, and there’s one slide I never have to work for.
It’s just a screenshot of a webpage. Bessemer Venture Partners — a storied, top-tier firm with roots dating back to the Carnegie Steel empire — maintains a page called the Anti-Portfolio. Not THE portfolio — The anti-portfolio. It is a list of the legendary companies they had a shot at and passed on, told in their own words, with the names of the partners who blew it.
Their framing, verbatim: being one of the nation’s oldest venture firms “has afforded our firm an unparalleled number of opportunities to completely screw up.”
Here’s the roll call, lightly abridged:
Google. The garage. That line.
Facebook. In 2004, at a corporate retreat, partner Jeremy Levine dodged a young Eduardo Saverin - and then got cornered by him in the lunch line. Levine’s counsel to the kid: “Kid, haven’t you heard of Friendster? Move on. It’s over!”
Tesla. Partner Byron Deeter met the team in 2006, test-drove the Roadster, loved it so much he put down a deposit - and passed on the company. His logic, which he also published: “It’s a win-win. I get a great car and some other VC pays for it!”
Apple. Offered pre-IPO stock at a roughly $60 million valuation. Deemed “outrageously expensive.”
PayPal. Passed on the Series A. Rookie team, regulatory nightmare. Four years later: sold to eBay for $1.5 billion.
eBay. David Cowan's reaction, preserved on the page: "Stamps? Coins? Comic books? You've GOT to be kidding." Followed by the verdict: "No-brainer pass."
Atlassian. Notes from 2006: totally self-financed, started on a credit card, founders don’t ever want to go public. When Bessemer finally got a real chance in 2010, the $400 million valuation was “a tad rich.” The shares they didn’t buy were later worth over a billion dollars. That’s not my math - that’s their page.
FedEx. They passed seven times. Seven.
And then, because apparently the self-immolation wasn’t complete, the page describes some of these as “a conscious act of generosity to another, younger venture firm” that “could really use a billion dollars in gains.” 🤣
Here’s why I keep coming back to this.
Every company on earth claims to embrace failure. It’s in the values deck, right between “integrity” and “bias for action.” Somebody’s on LinkedIn this morning posting about how their biggest setback was really their biggest teacher, and I promise you that person has not named a single specific thing they got wrong.
That’s the tell. Fake humility is abstract. Real humility is specific.
“We learn from our mistakes” costs nothing. “I said how do I get out of this house without going near your garage, and the guys in the garage were Larry and Sergey” costs something. It has a name attached. It has a room, a sentence, a person who has to walk into partner meetings for the next twenty-five years knowing it’s on the company website.
That specificity is the entire product. Bessemer didn’t write a humility statement. They showed receipts.
And I’ll say the thing the reverent posts about this page never say, because I think it’s more interesting than the reverence: this is also fantastic marketing. It’s a moat. Every founder who’s been rejected by a VC has felt small; this page is one of the only artifacts in the industry that says the smartest people in this business rejected Google, so your ‘no’ means less than you think. Bessemer has been telling that story for twenty-five years, and it’s very hard to copy - not because the idea is complicated, but because you can only laugh about missing Google if you’re winning everywhere else. Self-deprecation is a luxury good. It requires a balance sheet.
(To be fair: whether the page actually wins them deals is something Bessemer and its admirers assert, not something anyone has measured. Take the branding win as demonstrated and the deal-flow win as plausible.)
Now - go look for another one. I did.
Version One Ventures has an anti-portfolio. ISAI in Paris has one. GVA has one. A handful of angels keep personal lists. All of them small, all of them later, all of them following Bessemer.
Sequoia doesn’t have one! Andreessen doesn’t have one! Benchmark, Accel, Founders Fund, Kleiner - nothing! Not one brand-name firm has published a list of what it got catastrophically wrong. Twenty-five years, the format is free, everyone in the industry knows about it and quotes it at dinner, and nobody has copied it.
That silence is the real story. Bessemer’s page isn’t remarkable because it’s funny. It’s remarkable because everyone else read it, laughed, and went back to publishing only their winners.
I’ve been on both sides of this. I’ve pitched, and I’ve been the one saying no. When I was investing, I had a thesis, and I’d pass on anything outside it - cleanly, quickly, and sometimes, in retrospect, stupidly. Passing is the job. Most of the time you’re right, and the times you’re wrong are the times that get written about.
I’ve shown this to students in class and asked two things: first, if they were the General Partner at a VC firm, would they do this? Second, how can you apply this to your startup?
The lesson I want the students to take isn’t “VCs are dumb.” They’re not; Bessemer is a great firm, which is precisely why the page works. The lesson is that the confidence to publish your worst call is the same confidence that lets you make the next one. If you can’t say out loud what you got wrong, you’ll quietly organize your whole life around never being caught getting it wrong again - which is a spectacular way to never do anything. Even Michael Jordan - arguably the greatest basketball player ever - was famously quoted as saying, “I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times, I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.“
So here’s my ask — and I’ll go first. What’s on your anti-portfolio? Not the failure you’ve already sanded into a nice story with a lesson at the end. The one where you can still hear the exact dumb sentence you said.
Here’s mine. In the early days of Acquis, we were consulting for Concur — enterprise travel-and-expense software, long before anyone said “SaaS” out loud. We worked closely enough that co-founder and CEO Steve Singh made us an offer: instead of paying our roughly $100K invoice in cash, he’d pay it in pre-IPO equity. We took the cash. Young firm, real payroll — every responsible person might have made the same call. Concur went public in December 1998 at $12.50 a share. Sixteen years later, SAP bought the company for $129 a share in cash — about $8.3 billion, the largest pure-SaaS acquisition anyone had made to that point. That invoice would have been worth about $140K by the close of IPO day. By the time SAP wrote its check: over $1 million.
The exact sentence was some version of “we’ll take the cash.” I can still hear it.
And next Friday I'll prove I mean it — I found two tapes of myself from 2020 and 2022, and I'm grading every prediction on them. Publicly. Receipts attached.
Open Tab → I dove deeper: bvp.com/anti-portfolio.
Read the whole thing. It takes four minutes, and you’ll quote it for a year.
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