Travis Kalanick and the four paths of ousted tech founders

Key Points
  • Travis Kalanick could stage a remarkable comeback like Steve Jobs, have a strong second act like Marc Andreessen, or become an eccentric billionaire like Paul Allen.
  • But like most entrepreneurs — and most people — he probably had one big break, and Uber was it.
Uber CEO Travis Kalanick.
Shu Zhang | Reuters

Uber co-founder and long-time CEO Travis Kalanick left the company's board on Tuesday after selling his last shares, severing his final formal ties with the ride-sharing business he drove to success.

Kalanick co-founded Uber in 2009, then took over as CEO the following year. Investors ousted him from the top spot in 2017 after a series of missteps, including revelations that he'd allowed a culture of bullying and harassment toward women to fester, and an intellectual property lawsuit over self-driving cars from Google's parent company, Alphabet. He stayed on the board long enough to help select his replacement, then began selling off his stock earlier this year.

So what's next? The tale of the ousted founder has played out many times before in Silicon Valley, and typically ends in one of four ways:

The comeback

Apple co-founder Steve Jobs
Bloomberg | Getty Images

Apple co-founder Steve Jobs set unrealistic expectations for all other ousted tech founders when he returned to Apple in 1997 as the company was weeks away from bankruptcy. He undid some bad decisions, culled underperforming product lines mercilessly, then oversaw a hit parade of products — the iMac, iPod, iPhone and iPad — that eventually turned Apple into the most valuable company in the world. A decade before his return, he took a majority stake in Pixar, which set the stage for his biggest financial windfall. 

Twitter co-founder Jack Dorsey performed a similar feat, reclaiming the helm of the social media company in 2015 (first as interim CEO, later permanent) after being pushed out of the top spot in 2008. Since he took over, Twitter's core business has improved slightly — annual revenue rose only 37% between 2015 and 2018, while non-GAAP net income more than tripled — even as its average number of users per month stalled at around 325 million (the company has since shifted metrics and now reports average daily monetizable users).

Jobs and Dorsey both spent significant time away, building new companies and acquiring new perspectives along the way. Like them, Kalanick plans to spend his time building a new start-up, CloudKitchens, which creates and oversees centralized kitchens to cook meals for food delivery apps. If Uber continues to stumble — the stock is down more than 30% since its IPO — and Kalanick learns how to build a profitable business without falling into the same traps that hurt Uber during his tenure, he could become the rare comeback CEO.

The second act

Marc Andreessen, cofounder of Andreessen Horowitz, speaks at Recode's 2017 Code Conference.

Few founders create two runaway successes, although Dorsey was arguably in this category with his second company, Square, before he rejoined Twitter. Some successful founders play the role of entrepreneurs within the same company, such as Amazon founder Jeff Bezos parlaying his e-commerce dominance into the creation of one of the world's biggest enterprise software companies, Amazon Web Services.

Marc Andreessen is one example of a true second act founder. As the creator of the first popular web browser, Netscape Navigator, Andreessen co-founded one of the most successful companies of the dot-com boom. But Microsoft crushed the company by building a web browser into Windows, and AOL later snapped up Netscape for a song.

Then, a decade ago, Andreessen co-founded Andreessen Horowitz, where he used his hard-gained knowledge as an entrepreneur to build one of the most successful venture capital firms in Silicon Valley. Other big-name entrepreneurs to make the leap to venture investing include LinkedIn's Reid Hoffman, who's now at Greylock Partners, and AOL's Steve Case, who co-founded Revolution Partners. 

CloudKitchens could succeed, or Kalanick could take his knowledge and billions and turn them toward another completely unrelated business.

The eccentric billionaire

In this July 17, 2001 file photo, Seattle Seahawks owner Paul Allen appears in a suite in the team's stadium in Seattle. Allen, billionaire owner of the Trail Blazers and the Seattle Seahawks and Microsoft co-founder, died Monday, Oct. 15, 2018 at age 65.

Microsoft co-founder Paul Allen left the company for health reasons in 1982, merely seven years after it was founded. But he held most of his Microsoft stock and it turned him into a billionaire many times over. Along the way, he devoted himself full-time to a diverse array of interests, including the purchase of the NBA's Portland Trailblazers and NFL's Seattle Seahawks, while snatching up huge swaths of real estate in Seattle, and founding an institute devoted to researching the human brain. He also bought one of the world's largest yachts with an attached mini-submarine, and became a passable rock guitarist before starting a museum devoted to his musical hero, Jimi Hendrix. He died of cancer in October 2018.

By most accounts, Kalanick was maniacally single-minded about Uber, and doesn't seem to have the diversity of interests that Paul Allen enjoyed. Moreover, Allen's net worth peaked around $30 billion in 1999, and he was worth around $20 billion when he died. Kalanick sold less than $3 billion worth of Uber stock, which barely buys an NBA team these days.

The fadeaway

Marc Tarpenning, Tesla co-founder, is now a venture partner at Spero Ventures.
Jeff Bartee

While comebacks and second acts are interesting, they're also exceptional. Most company founders — like most people — get one big break. They may go on to have productive and successful lives after they leave, but they seldom re-renter the public consciousness like the companies they founded.

For instance, only the most astute students of the tech industry history know the names Leonard Bosack and Sandy Lerner, who founded Cisco and were ousted after the company went public in 1990. Cisco didn't become a household name — and, briefly, the most valuable tech company in the world — until after 1995, when John Chambers took over as CEO.

The same goes for Martin Eberhard and Marc Tarpenning, who founded an electric car company in 2003 and were helped along by an early investment from former PayPal exec Elon Musk. Tesla struggled for years but finally became a significant automaker — and iconic brand — under Musk's eccentric leadership.

Kalanick has built a different profile than his predecessors, more famous than some, more infamous than all of them. And Uber is a much bigger and more valuable company than the others were when their founders departed. Even so, if Uber itself fades in importance — the company still generates massive losses, and investors are torn whether to believe in the company's plan for eventual profits — Kalanick could find himself as no more than a very wealthy footnote from a particularly mediocre period in Silicon Valley history.

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