Failing isn’t a career killer in Silicon Valley

October 26, 2020, 1:15 PM UTC

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The ever-quotable investment manager Eric Jackson may have had the best quip about Quibi, as post-mortems about the failed startup led by Jeffrey Katzenberg and Meg Whitman poured in this weekend. “Maybe there is nothing to be learned from Quibi,” he tweeted on Saturday morning. “I can’t remember a time when the conventional wisdom has been so dead on.”

It’s a fair point. So instead of rehashing the $1.8 billion Quibpocalypse one more time, let’s revisit some other failed startup leaders and see how they’re doing.

Travis Kalanick got dumped by Uber amid myriad legal probes. Now he’s on a real estate acquisition spree for his delivery food startup CloudKitchens with $400 million from Saudi Arabia. Parker Conrad was booted from HR startup Zenefits amid a scandal over insurance sales. Now he’s back at the helm of Rippling, a similarly focused startup with at least $100 million of backing from top VCs. They say Jawbone founder Hosain Rahman ran through $1 billion before shutting down the smart speaker maker. He’s raised $65 million for his health-oriented next act, now called all.Health. And Kevin Gibbon, whose failed startup Shyp helped people deliver stuff they sold on eBay, is back with Airhouse helping e-commerce companies deliver stuff they sell online. Gibbon is warier of VC backing this time around and said he’s raised under $5 million.

Some former founders are making it back without quite being CEOs again. Juicero founder Doug Evans squeezed through $120 million; his new venture is a book on healthy eating. Former Anki CEO Boris Sofman shut down his toy robotics company that burned through $200 million; he was snapped up by Waymo to head its self-driving truck effort.

And then there are the failed leaders who have yet to turn up, like Essential’s Andy Rubin, Chariot’s Dan Grossman, or UBiome’s Jessica Richman.

What fate awaits KBerg and the Whit? Time will tell.

Aaron Pressman



Transformed in his bed into an enormous insect. The CEO of spooky data analytics startup Palantir, Alex Karp, has no background in data analysis, computer science, or much of anything that seems relevant to the job. The Stanford law grad and philosophy PhD tells the New York Times he's not much help in sales pitches: “You think it is helpful having a fluorescent praying mantis coming into their office, telling them about German philosophy? Do you think that’s helpful? I can tell you, it’s not helpful."

Too old to be chillin' at the playground. The cloud gaming market is getting a bit overcast. Facebook on Monday debuted its new service within its desktop and Android apps with titles including Asphalt 9: Legends, PGA TOUR Golf Shootout, Solitaire: Arthur’s Tale, and WWE SuperCard. But, sorry, no iPhone versions due to Apple's current policy against allowing such services.

Bill comes due. South Korea's richest man, Samsung Electronics chairman Lee Kun-hee, died on Sunday. The country's significant estate taxes could force Lee's heirs to sell their controlling stake in the company. But the family could also opt to spread out the tax payments over multiple years and avoid a fire sale.

Not enough bills. On Wall Street, shares of European software giant SAP are tumbling. The company said revenue declined 4% to $7.7 billion and that it no longer expects a recovery in its travel expense unit this year. SAP's shares, which had previously gained 12% this year, dropped 21% in pre-market trading on Monday. Also, Jack Ma's Chinese payments startup Ant Group will raise a staggering $34.5 billion in its initial public offering this week on stock exchanges in Shanghai and Hong Kong. That will make it the biggest global IPO in history.

Folding bills. As you know, I am a fan of the two-screen Microsoft phone, the Surface Duo, but with some software bugs and a crummy camera, it's tough to recommend at $1,400. Now, after less than two months on the market, it's down to $1,100. Does that mean it's selling well?


Friday's "Food for thought" about Steve Jobs' imprint on Apple brought an email of a rebuttal from iPod designer and Nest co-founder Tony Fadell. Fadell disagrees with Apple University dean Joel Podolny and professor Morten Hansen:

Quite ironic that this article is published on the 19th anniversary of the original iPod launch.

Joel maybe you should talk to my wife, who hired you for your position, to remind you of the Apple organizational facts that you conveniently left out?

The ol’ trick: Represent various facts to build the narrative instead of actually telling the truth of the situation - the current org was built based on personalities…


This startup wants to help you prepare for America’s next disaster By Katherine Dunn

With offices closed, WeWork and other coworking spaces jump on market opportunity By Alyssa Newcomb

Former Facebook employee’s new book exposes Big Tech’s dirty secrets By Danielle Abril

The electric car frenzy is helping even troubled companies raise big money By David Z. Morris

Is it time for a new agency to oversee Big Tech? Many say yes By Jeff John Roberts

Stop doomscrolling on social media and read a book By Padmasree Warrior

(Some of these stories require a subscription to access. Thank you for supporting our journalism.)


Remember the murder hornets? The flying demons made it across the Pacific to the U.S. Northwest somehow, endangering the lives of millions of honey bees. Well, the honey bees and all hornet-fearing people can rest easy. Scientists tracked one of the beasts and wiped out their nest. So that's one less dystopian nightmare to worry about.

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