The Man in Silicon Valley Who's Completely Obsessed With Failure
A tech investor is turning his home office into a shrine to failure. His collection has more than 1,000 relics from business fiascoes — and it keeps expanding.
As a venture capitalist based in the heart of Silicon Valley, Sean Jacobsohn is in the business of hunting for success. And he recently did something that would have sounded completely nuts almost anywhere else on the planet.
He decided to build his own personal monument to failure.
When he works from the desk in his home office (top), he is now sitting in the middle of the Failure Museum, which might be the world's largest collection dedicated to business fiascoes, corporate malfeasance and spectacular flops.
There are Bear Stearns mugs, several models of BlackBerry and pieces of Bernie Madoff's stationery. There's a WeWork thermos, unopened Champagne from Webvan's initial public offering during the dot-com bubble and, of course, cans of New Coke. There is somehow cologne from both Harley-Davidson and Burger King. There are not one but two Pets.com sock puppets. And there is a Mattel doll, but it's not Barbie or Ken — it's Allan.
He estimates that he's spent tens of thousands of dollars acquiring items that most people would rather forget. These days, there are more than 1,000 artifacts of terrible, puzzling, and downright criminal business decisions in glass display cases, and he would be surrounded by even more remnants of failure if not for one problem.
"I've actually run out of space," Jacobsohn says. "I have 30 boxes in the attic. My wife wants to build an extra room on the house."
[The Allan doll, a discontinued product from Mattel.]Those boxes are full of mementos from incandescent blowups and products that deserve to be shot into another galaxy. But he doesn't just look for toys, novelty items and the ruins of memorable calamities. Even the most successful companies in history have commemorative objects in the Failure Museum.
Apple quickly pulled the plug on a personal computer called the Power Mac G4 Cube. Microsoft's clunky attempt to clone the iPod resulted in the Zune. Google Glass existed.
Jacobsohn believes there is a lesson to be drawn from every regrettable object in his collection. As he built the Failure Museum, he began to think more about the causes of business failures, and he developed his own framework to understand why most startups go belly-up. He calls his theory the Six Forces of Failure.
The list: bad product-market fit, shaky finances, ignoring customer feedback, tough competition, poor timing, and people — pushover boards, ineffective management, founders who are frauds.
His main takeaway is that failure is an integral, too easily ignored element of success. Anyone who wants to get something right should be aware of the many ways that it could go really, really wrong.
In the tech capital of the world, someone who hasn't failed probably hasn't been very successful. As it happens, there is no place more appropriate for a shrine to failure than Silicon Valley, which not only accepts but almost encourages it. When he looks at startup founders who have never tasted failure, Jacobsohn sees entrepreneurs who have never taken meaningful risks.
"VCs are not afraid to invest in entrepreneurs who have failed before," Jacobsohn said.
So how does a guy who spends his day looking for winners decide to remake his office into a Louvre for the losers?
[Myspace playing cards, a can of New Coke, and a pair of Google Glass, items from Sean Jacobsohn's Failure Museum.]
Jacobsohn, 52, grew up collecting sports cards and paid his way through the University of Wisconsin buying other people's memorabilia collections and selling individual pieces. After graduating from Harvard Business School, he channeled his entrepreneurial mind into more traditional pursuits. He worked as an executive at three startups that later went public, joined the investment firm Norwest Venture Partners, and now sits on more than a dozen company boards.
His peculiar obsession was born in an unlikely place: a Golden State Warriors game. Over the past decade, the Warriors have been the National Basketball Association's most successful team. But that night in November 2022, Jacobsohn couldn't stop thinking about failure.
As he walked into the arena, he was given a bobblehead of Warriors guard Jordan Poole that came in a box with three curious letters: FTX. Sam Bankman-Fried's cryptocurrency exchange had imploded only days earlier, but it was too late to remove the disgraced company's branding. The timing of the giveaway was awful — and inspiring.
When he got home, Jacobsohn knew what he had to do: write about it on LinkedIn.
[An FTX-sponsored Jordan Poole bobblehead. The bobblehead inspired Jacobsohn to start his collection.]
The response was so overwhelming that he began looking around his house for similar relics and scouring eBay to buy more. He's been curating vestiges of corporate failure ever since. Before long, his collection was big enough that he called it a museum. Now, whenever he needs a reminder of the surprising value of failure, he can simply look behind his desk.
Jacobsohn doesn't exactly sell tickets to his house, but he does host entrepreneurs at the Failure Museum every week. When they visit, he advises them not to avoid the kind of risks that might one day result in their enshrinement. After all, failure is fetishized more than it's feared in Silicon Valley, where it takes a risk tolerance bordering on delusion for a few people in a garage to believe they can make something that will change the world.
The first time he toured the Failure Museum, Jeff Crowe felt like he was walking through business history. Norwest's senior managing partner says he looks for "a track record of exceptional accomplishment" when he's investing — and that includes how entrepreneurs deal with failure. He asks them what they learned along the way and how those experiences bred resilience, since founders who don't understand why they failed are likely to fail again.
"If you only talk about success and never talk about failure, you're missing half the equation," Crowe said.
There are several ways that Jacobsohn finds stuff for the Failure Museum.
His friends contribute defunct gadgets, ironic swag, and discontinued products they have acquired over the years. This is how he copped a pack of Myspace playing cards and a bottle of Mazagran, a bubbly coffee from Starbucks and PepsiCo that never made it past a trial run. He also takes donations from complete strangers, like a Blockbuster membership card and a Juicero, tech's infamous attempt to disrupt juice.
For everything else, there is eBay. The best $220 he ever spent there was on a Theranos lab coat. He crossed another elusive item off his list when he paid $150 for an ESPN mobile phone, which Steve Jobs once called "the dumbest f—ing idea I have ever heard."
"It's something I'd been trying to get for a long time," Jacobsohn said.
[Microsoft's Zune, an Apple Power Mac G4 cube, and an ESPN mobile phone.
But in retrospect, even some of the dumbest ideas look like they were ahead of their time. ESPN's phone helped lay the foundation for the company's mobile dominance today. And the Mazagran debacle led to another bottled drink that worked out slightly better for Starbucks: the frappuccino.
Before those items were consecrated in the Failure Museum, there was the Museum of Failure, an unaffiliated pop-up gallery that began traveling the world in 2017, presenting exhibits like "bad taste" (Heinz purple ketchup) and "failure in motion" (grass skis and Segways). It has stopped in New York, Washington, Hollywood and the Mall of America in Minnesota — but not Silicon Valley.
"This is a major meta-failure," said Samuel West, the Museum of Failure's founder and curator. "We have still not managed to open in the most failure-friendly place on earth."
But you don't need to visit either museum to learn from failure. And there might not even be that much to learn from it.
In fact, one newly published scholarly paper found that the benefits of failure are greatly exaggerated.
"We're all overestimating the likelihood that success will follow on the heels of failure," said Lauren Eskreis-Winkler, a Northwestern University psychologist and one of the paper's authors.
And it's true that many of the companies, ideas, and doomed products in the Failure Museum were made possible by the foolish bets of VCs who think failure is more instructive than it might be. In the future, maybe they should be more chastened by failure.
But in the meantime, Jacobsohn says he's in the market for a copy of Enron's code of ethics, a Levi Strauss three-piece suit, and a bottle of Jolly Rancher soda to pair with the can of Life Savers soda that he proudly displays in the Failure Museum.
It might be time for that new wing.
[A Theranos lab coat and mug, a Pets.com sock puppet, and a Blockbuster membership card and store sign.]
More?
Your wish is my demand.
How about some YouTube videos featuring the original Museum of Failure cited above so you can waste even more time not doing whatever it is you're supposed to be doing?
