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Ryan Graves may be asked to step down from Uber—here's how he became its first CEO

  • Ryan Graves went from an intern to a top start-up executive.
  • He was CEO of Uber in 2010.
  • Reports say that Graves knew about Uber's "greyballing" and that Graves headed up HR amid allegations of sexism.
  • Those who know him say he is "nice, genuine and hardworking."

Travis Kalanick has become the face of Uber, the brash and super-successful entrepreneur that "holds no prisoners" and bleeds "Uber blood."

But central to Uber's recent unraveling is a less familiar face — Ryan Graves, the start-up's first CEO. Though Graves has faded from Uber's limelight over the past seven years, an explosive internal investigation may lead to his termination, sources indicated to Recode this week.

Yet Graves' role at Uber remains somewhat mysterious.

Back in 2010, Kalanick didn't want to run Uber full time — and put Graves in the role. Then a 20-something newlywed fresh out of the Midwest, Graves was an unlikely executive who served only a short stint at the helm of Uber in 2010. But he has remained at the company through its success, and more recently, its turmoil.

Uber head of global operations Ryan Graves (R) eats with fourth grader Frederick Dozier during Cooking Matters, a nutrition class taught by 18 Reasons, a local partner of Share our Strength at Glen Park Elementary School in San Francisco, California, December 10, 2014.
Beck Diefenbach | Reuters
Uber head of global operations Ryan Graves (R) eats with fourth grader Frederick Dozier during Cooking Matters, a nutrition class taught by 18 Reasons, a local partner of Share our Strength at Glen Park Elementary School in San Francisco, California, December 10, 2014.

In particular, Graves was aware of "greyballing," a tool Uber used to evade authorities around the world, according to The New York Times. That program is now subject to a criminal probe, Reuters reported.

Graves' stake in Uber is also enough to make him one of the world's youngest billionaires, according to Forbes. That stake, and the board seat that comes with it, could become crucial as Uber considers who, if anyone, should be ousted over a series of scandals that include accusations of gender bias and alleged intellectual property theft.

An Uber insider told Business Insider that Graves, known as Uber's "Mr. Nice Guy," had "vanished from the office," and that employees feel Graves hasn't displayed the leadership they would have expected. Recode reports that Uber's HR — accused by a former employee of dismissing sexism allegations — reported to Graves.

From intern to CEO

Graves' professional trajectory was exponential: He went from an intern to a top start-up executive.

On a now-defunct Tumblr, Graves listed his positions prior to Uber as an intern for 3 months at FourSquare, while he was also a program manager at GE Healthcare as part of the Information Management Leadership Program.

Graves, a San Diego native and Padres fan who grew up near the beach and wanted to see the world, had little technology background. A member of the water polo club team and the Beta Theta Pi fraternity, Graves graduated from Miami University in Ohio with an economics degree in 2006, a period he described as "some of the best years of my life." He married his college sweetheart, a kindergarten teacher named Molly who loved fashion.

After interning at UBS, Graves said he did a stint as a consultant at a Chicago firm called PartnerSolve, following Molly to the Windy City, before founding and subsequently shuttering at least one start-up, a Tweetdeck-like social media project called SocialDreamium.

"When I joined GE at the very end of 2007 I had expectations of what opportunities the job would provide," Graves wrote in a Facebook post. "Since I had interest in technology, I joined the Information Management training program to follow the path of [former GE chief] Jack Welch. There was an 'unofficial' promise that if I was the top of my class at the 1-year point I would be able to work abroad, there was the off program salary that was very appealing, there was the job titles, and the opportunity to work directly for a CIO."

HAPPY THANKSGIVING! be thankful for smiles.

A post shared by ryangraves (@ryangraves) on

Then the financial crisis hit, hard — his sister was laid off, the competition took a bit out of his start-up, and Graves started thinking about what the workforce would require of him and whether he trusted "the system."

"I realized I couldn't break into the start-up world by being the GE guy," Graves told a Fortune reporter in 2015, appearing in one of the checkered button-up shirts that are somewhat of a trademark. In a speech in Iowa in 2012, he called Uber his "first successful entrepreneurial venture."

What Graves lacked in technical know-how, he made up for with uncapped enthusiasm for the start-up space. Beginning in 2008, his Tumblr page was filled with think pieces about the financial crisis, venture capital, social media and even trading Google shares below $400 a share (they are over $950 today). He tweeted prolifically at big start-up figures like Fred Wilson and Brad Feld. He was "glued to TechCrunch."

Graves said it was Wilson who helped him get his internship at Foursquare. And in a now-famous Twitter exchange, Graves' ambition paid off big time and catapulted him to CEO of what has since become one of the most valuable privately held companies in the world.

The early days of UberCab

By mid-2009, Kalanick was "temporarily" running Uber, which had yet to launch, with co-founder Garrett Camp.

"I wasn't yet ready for a full-time gig – still recharging from a 10 year non-stop startup life in P2P technology – and we both thought the business was going to be pretty low-tech, mostly operational – Little did we know," Kalanick wrote of early days at Uber.

By January 2010, Kalanick said, he was interviewing Graves to take over.

"Funny story how we brought him in. I was hitting Craigslist, Twitter, and other channels looking for the right candidate. What resulted was the Awesomest job post and response I've ever seen (I'm @konatbone):"

Source: Uber Newsroom

He got the job and moved to Hayes Valley in San Francisco, leaving a half-packed apartment in Chicago after 4 years.

"The world of no health insurance, jamming late nights, endless responsibility, and some of the most fun I've ever had are ahead of me and I'm so stoked," he wrote.

Graves started working at Uber in March 2010, demoing the product, with Kalanick dropping by for about 15 to 20 hours a week. Graves steered the company through its launch and first round of financing — for the next two years he didn't take any vacations.

In the first two months after the app launched, the company went from coordinating 5 rides per night to about 50, Graves said in a Facebook post, crediting the rise to customers' forgiveness for early-stage companies. The team started hiring for their first full-time engineer in April, and by June, Graves had moved the rest of his stuff to San Francisco.

"I work with a ton of young startup executives, but rarely have I had the opportunity to work with someone as high quality as Ryan," Kalanick wrote at the time. "He's got the trifecta: Hustle, emotional intelligence, and smarts. .... He learned the startup game fast and worked his ass off to build the Uber team and make the San Francisco launch and subsequent growth a huge success."

Graves, center right, poses with NASA astronaut José Hernández, center left, with Los Ubers, a group of Uber employees "committed to spreading the vibrancy of Latino culture" Source: Uber Newsroom

But by December, Kalanick took over as CEO. Graves cited their "mentor/mentee" relationship, and both said they were "pumped" by the changes in the company, calling it a "partnership, not a replacement."

Graves, then general manager and vice president of operations, wrote later that the handover was "a little bit of an ego/gut check."

"I wasn't being forced out, and the position Travis was asking me to accept was one that I thought really aligned with my strengths," Graves said in an interview with a venture capital firm.

Since then, Graves has been involved in a myriad of projects, including the company's international expansion and UberEats meal delivery service.

His Twitter feed, mostly silent on Uber's issues, is largely focused on politics (he's a passionate environmentalist). Now a family man, Graves aims to be home for dinner at least once a week for dinner with his young children.

The anti-Travis?

Kalanick has undoubtedly been a driving force in Uber's skyrocketing valuation, which now approaches $68 billion, according to CB Insights.

"Travis is who he is. He doesn't try to play the political brand or water things down," SB Projects, an early Uber backer, told CNBC last year. Jason Calacanis, another investor in Uber, said Kalanick has the makings of a "legendary CEO" in the vein of Microsoft's Bill Gates and Oracle's Larry Ellison.

Uber CEO Travis Kalanick
Danish Siddiqui | Reuters
Uber CEO Travis Kalanick

But that hard-driving approach has also lent itself to a "fighter mentality," Calacanis said. Susan Fowler, a former Uber engineer, wrote that Uber's culture was, indeed, political, noting that upper management did little to address her concerns about sexism.

"We all lived under fear that our teams would be dissolved, there would be another re-org, and we'd have to start on yet another new project with an impossible deadline. It was an organization in complete, unrelenting chaos," Fowler wrote in a viral blog post.

Fowler doesn't name which executives were involved in the most inflammatory incidents she witnessed, like the decisions to exclude women from getting corporate leather jacket.

But that kind of behavior does not seem to fit Graves' personality, at least not from what we know as his early days as an executive, more than 7 years ago. He was "nice, genuine and hardworking," according to one college friend who spoke to CNBC.

"Culture isn't something that you force feed your team." -Ryan Graves, Uber

In his book, "The Upstarts," author Brad Stone describes Graves' hiring of Austin Geidt, the first woman to work at Uber. Geidt had been addicted to drugs in college, recovering to find her career adrift before she was hired by Graves as a marketing intern.

She told Stone that she struggled to fit, had "terrible impostor syndrome," and found Kalanick stressful. But Graves "counseled her in the stairwell to the office, with Geidt in tears."

"Instead of firing her, though, Graves gave her time to find her footing," Stone wrote. "Later he dismissed his first driver-operations manager and installed Geidt in the role."

She, like Graves, would go from intern to key Uber exec and advocate of Uber's culture.

But in a 2012 interview with a venture capital firm, Graves also emphasized that he thought rewarding individuals was an important part of building culture in a company — but that forcing the culture issue was "kind of lame."

"Culture isn't something that you force feed your team," Graves said. "It's more of a byproduct of who you are collectively, what you stand for, and what you value most. If you focus on people individually — the work that they do and the way in which they're rewarded — I think that will have a far greater impact on your business, and culture will take care of itself."

An uncertain future for top Uber executives

Graves' lack of prior experience reportedly came back to haunt Uber during a contentious time internally.

According to Recode, Uber's first official head of HR, Renee Atwood, was hired in 2014 and reported to Graves. Sources told Recode that Atwood asked to report directly to Kalanick, as she and other managers felt Graves was too green to handle complex HR matters appropriately. But after Atwood left the company, it was Graves who acted as the interim head of human resources, Recode's sources said.

Then there's the evasion of authorities in the "greyball" program — which Graves reportedly knew about — and may become one of two federal investigations that now faces Uber.

It's unclear how deep Graves' involvement in these scandals goes, and how many of his actions were under the wing of Kalanick.

But the world may find out soon. In February, after Fowler's bombshell blog post and subsequent media reports of widespread harassment at the company, Uber commissioned former U.S. attorney general Eric Holder to conduct a wide-ranging investigation. That report will be presented to top Uber execs near the end of May, and to employees the week of June 5, according to Recode.

Graves, a surfer and serious photographer, wrote on his website in 2008 that the fallout from the economic crisis had inspired him to turn to surfing, and entrepreneurialism, as a way to take advantage of "turbulence."

"Instead of paddling around in circles as though we were in some calm lake, we need to learn to act like surfers to place ourselves in the rising and falling swells, paddling forward while glancing occasionally backwards, so that we will be ready when the big wave comes. If we do that, we will stand up at the right moment, establish our balance, take a deep breath, and ride the exhilarating force of history all the way to shore," Graves wrote, quoting a Harvard Business Publishing article.

For Graves, a big wave may be on the horizon.

Correction: This story has been updated to more accurately reflect the nature of Austin Geidt's addiction.