The Uber-Complex Battle Behind Showtime’s ‘Super Pumped’

Uber has made a remarkably speedy rise from a simple transportation company to a worldwide courier that delivers your food and freight, and rents out cycles and scooters. But it’s the corporate speed bumps and potholes the company dealt with that are the fuel for Showtime’s Super Pumped: The Battle for Uber. Season 1 of the anthology series, premiering February 27, stars Joseph Gordon-Levitt as Travis Kalanick, former CEO of the ride-hailing giant, alongside Kyle Chandler as Kalanick’s onetime ally Bill Gurley.

As Showtime explains in a synopsis, this season of the series “pivots on Kalanick, Uber’s hard-charging CEO who was ultimately ousted in a boardroom coup, and his sometimes-tumultuous relationship with his mentor Bill Gurley, the plainspoken, brilliant Texan venture capitalist who bets his sterling reputation on Uber’s success — and then has to live with the consequences.”

So what happened between Kalanick and Gurley?

For starters, Gurley pumped $12 million into Uber in 2011 through his company, Benchmark, and joined the company’s board of directors, as The New York Times reported, in March 2017. At the time of that Times article, Gurley had a “tight relationship” with Kalanick and was “the closest thing Mr. Kalanick [had] to a consigliere,” the newspaper observed.

But the Times also reported on the challenges Uber was facing in early 2017: Former employees had made charges of sexual harassment and discrimination in the workplace. The company had allegedly used a tool to identify and deceive authorities trying to regulate the platform. Kalanick was caught on video swearing at an Uber driver who complained about falling wages. Waymo had accused Uber of stealing technology. And Uber faced mounting competition from rival ride-sharing platform Lyft.

Travis Kalanick (Elijah Nouvelage/Getty Images)

In June 2017, just three months after that Times article, five of Uber’s major investors — including Gurley’s Benchmark — demanded Kalanick’s resignation, noting that the company needed new leadership. Kalanick acquiesced, saying in a statement that he “accepted the investors’ request to step aside so that Uber can go back to building rather than be distracted with another fight.” A statement from the Uber board explained that Kalanick’s resignation would give the company “room to fully embrace this new chapter in Uber’s history.”

(HuffPost co-founder Arianna Huffington, played in Super Pumped by Uma Thurman, was another Uber board member at the time, and she served on a three-person committee that got updates on an independent investigation into claims of sexual harassment at Uber, according to CNN Business.)

On the day Kalanick stepped down, Gurley previewed the outgoing CEO’s legacy on Twitter, writing, “There will be many pages in the history books devoted to @travisk — very few entrepreneurs have had such a lasting impact on the world.”

Bill Gurley (Brian Ach/Getty Images for TechCrunch)

The following day, news broke that Gurley was departing the Uber board. And that August, Benchmark filed suit against Kalanick for fraud, breach of contract, and breach of fiduciary duty, in an effort to get the former Uber CEO off the board of directors and revoke his power to fill three board seats, per Reuters. (That lawsuit was dropped in January 2018 as a condition of a SoftBank investment that allowed both Benchmark and Kalanick to sell stakes in Uber, according to TechCrunch. Kalanick ended up leaving the board in December 2019.)

In November 2019, Gurley explained on CNBC’s Squawk Alley why Benchmark sought to replace Kalanick as Uber’s CEO. “We reached a point where we felt like the entire company and all its constituencies — drivers, riders, employees, shareholders — were at risk if the company continued to move in the direction it was,” he said on the show. “We took action that was not easy to take. We’ve suffered some brand hits as a result, but we felt like we were on the right side of history.”

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Gurley also hailed the progress of Dara Khosrowshahi, Kalanick’s successor as CEO. “I think today, if you ask anyone involved, ‘Are we better off because of Dara’s leadership and where we’re going?’ I think they’d all say yes,” Gurley said.

Now Showtime is retelling this story in the first season of Super Pumped, drawing from the 2019 book of the same name by New York Times journalist Mike Isaac. (The series has already been renewed for Season 2, when it will reportedly focus on Facebook.) “The Showtime series will depict the roller coaster ride of the upstart transportation company, embodying the highs and lows of Silicon Valley,” the premium cabler explains. “Even amid the radical upheaval generated within the global tech capital, Uber stands out as both a marvel and a cautionary tale, featuring internal and external battles that ripple with unpredictable consequences.”

Super Pumped, Series Premiere, Sunday, February 27, 10/9c