opportunity and replied.
The two took to one another almost immediately. Graves liked Kalanick’s worldliness and “funding shepherd” machismo. Kalanick appreciated Graves’s audacity, hustle, and energy. Graves was game for anything. Shortly thereafter, the twenty-six-year-old Ryan Graves became UberCab’s first full-time hire.
“I’ll be at the ground floor of a startup that has the opportunity to change the world,” Graves posted to his Facebook as he prepared to leave the Midwest. “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.”
Graves and his new bride, Molly, packed their truck, pulled away from their Chicago apartment and headed west to San Francisco.
Since neither of them wanted to do the job, Camp and Kalanick decided that Graves, young and full of hustle, should be the company’s first chief executive. Graves was ecstatic; he finally had his chance to prove he could make it at a startup.
It didn’t last long. Graves’s friends have always considered him an “A-plus guy,” but he turned out to be a B-minus chief executive. During the company’s early fundraising days, he’d walk into important meetings with venture capitalists and fumble stats or other talking points. Despite his confidence, he could never deliver a convincing enough pitch to seal the deal. Graves didn’t have company-building experience, like Camp, or the ability to rapidly crunch numbers, like Kalanick. Graves was a charmer and a hard worker, but those qualities only went so far. Investors were interested in the idea, but didn’t think Graves had what it took to make it big.
There’s a familiar line of thinking among the technorati: Good ideas are important, but venture capital is all about making the right bet on the right person at the right time. When sizing up a founder, a venture capitalist asks: Will this guy—and in the sexist tech industry, it was almost always a guy—be the one to take a startup from a handful of hard-working kids to a Fortune 500 company someday? Will this guy stick around when the shit hits the fan? Is this a guy I’m willing to bet millions of dollars on? People liked Graves. But for most of the VCs who met him, the answer to those questions was no.
During the early days under Graves’s CEO tenure, co-founder Camp began tweeting cryptically about UberCab. They hadn’t announced anything about their new venture yet, but the three men teased their “stealth startup,” a commonly used phrase to build allure (whether a project deserved it or not).
Rob Hayes, a partner at First Round Capital, saw Camp’s Twitter schtick and was intrigued. He sent an email, met the company, and quickly cut a check for nearly half a million dollars in the company’s first “seed” round of funding. Chris Sacca, a friend from Kalanick’s “JamPad” days, also threw in a chunk of capital, along with a handful of other close acquaintances who became “advisors”—a glorified title for early supporters. Of the early group of seed investors, though, Hayes and Sacca were the most hands-on, offering advice and strategy. Hayes and Sacca’s seed investments would one day be worth hundreds of millions of dollars.
That first seed round gave UberCab enough runway to build the essentials of a real startup. After working out of Hayes’s office at First Round Capital for months, the UberCab team rented desks in a shared workspace and started bringing on early team members.
Hayes, Sacca and others agreed: Graves was a great guy, but he was no CEO. He had to go. In an early meeting with Kalanick, Camp, and Hayes, they tried to break the news to Graves as gently as possible. Graves’s pride was hurt, but he took it well enough and accepted a position as general manager and vice president of business operations.
Kalanick took the opportunity to seize control. Upon agreeing to the CEO role, he insisted on being given a larger ownership stake in the company. It was important, Kalanick believed, that the leader of UberCab have complete say over his company’s path forward, which meant he should hold majority control. Kalanick didn’t care about his salary; he already had a taste of wealth after selling Red Swoosh. What he wanted was power.
He got it. Camp and Graves signed a chunk of their shares over to Kalanick as compensation for his new position, a move that would tie Kalanick permanently to the company’s outcome whether it emerged as a success or, more likely, an embarrassing failure.
During the