Why you should care

Because the lives of the moneybags are always worth hearing about.

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When you walk into the loft-chic offices of First Round Capital in San Francisco’s South of Market district, you are greeted by a small, gray metal dresser. It is an altar to disruption. In its center sits a typewriter worthy of a hipster bookstore. To its right, a dull old Macintosh, gray framing the monitor and that stripy little apple at the top. And on the left, a blue iMac laptop. It’s cute. It doesn’t seem that ancient.

Of course, that’s the point: In a variation of Ferris Bueller’s point, the future comes pretty fast — and if you blink, you might miss it. One unblinking oracle sits upstairs in First Round’s office: Rob Hayes, a relatively mild-mannered fellow who seems pretty average but is actually one of Silicon Valley’s major power brokers, at the helm of one of the most respected venture capital firms in the country. In his corner of the office, Hayes’ back is turned to a quietly humming open-space work area — obviously, no cubicles here. His is a cushy gig — particularly nice in a region where the VC industry raised a shocking $7 billion in just the first quarter of this year, according to the National Venture Capital Association. Hayes’ expertise is in picking top-notch seed-stage investments — the stuff that’s about to gather speed — before anyone else does. Any VC will tell you that’s their thing, but few have the record Hayes does, with mouthwatering companies in his portfolio like Uber, Square and Mint.com.

Rob Hayes First Round

Venture capitalist Rob Hayes.

Source First Round

Today? The firm, which invests in about 40 companies a year, also boasts FlightCar, Refinery29, Warby Parker, Yummly — you get the picture — in its pockets. Ask Hayes, and he’ll do the humility shtick: “The founders are doing God’s work.” He’s not the builder of stuff; a former product manager at the now-defunct Palm OS, he much prefers being the fixer, the ideator, the inceptor. But here, it’s the VCs who wield the real power, and, as Hayes admits, the days of venture funders being “the advisers, the assist man,” as he puts it, are gone. He’s been one of those power wielders for a long time now; he started a corporate VC fund at Palm after its 2000 initial public offering, where he made six “terrible” investments and lost about $25 million. He got a second shot, following his old boss to Omidyar Network, where they had more success running the company’s venture arm. That early experience made Hayes an old hand in an industry full of “insecurities” by the time Web 2.0 came around, says Josh Kopelman, Hayes’ First Round colleague and the firm’s co-founder.

Nick Weaver, CEO of Eero, a Hayes-backed company, says Hayes’ product history makes a big difference in his advisement. He thinks about stuff “as a consumer would.” To get that perspective, Hayes says, means occasionally doing research in a slightly unorthodox way. Take Uber, for instance — back when Hayes threw his hat in, the company was a black car service on an app, pre-Uber X, UberPool, etc. Hayes wasn’t sure whether folks who didn’t usually use black cars would use this newfangled app. He called an Uber … but the thing about smart entrepreneurs, he says, is that if they’re any good, they’ll have a hit list: emails of press, investors, etc. And if they see a Hayes or a TechCrunch reporter try to use the product, well, a dog and pony show might ensue. Time to go undercover, register a fake email address and call the car that way. Obviously, the incognito research worked out for what is now a $50 billion-valued company.

Hayes has messed up along the way, of course. Like when he failed to invest in Dropbox, he says with a slight grimace. But his bigger mistakes have taken place outside of work. In his sunny upstairs office, framed photos of his daughters, ages 13 and 15, are prominently featured on bookshelves. “They’re awesome,” he gushes of his children. Family is a frequent point of discussion for Hayes. That legendary Uber investment? It certainly cost more than the VC money. He tells me, not quite sadly but with the demeanor of a guy confident he has learned from a mistake, that on the days leading up to it, he was on a family vacation with the wife and kids in Oregon, where cell service was spotty. Hayes spent the whole time running around between various hilltops trying to make calls to seal the deal. He and his daughters’ mom are now divorced. He spent the summer commuting between San Francisco and Philadelphia, his new wife’s hometown.

Clearly, life’s pretty different from Hayes’ childhood, which he spent in agricultural Stockton, California, growing up next to an asparagus farm (“It’s the asparagus capital of the world!”) and near an inland deep-water port where he watched ships come and go. He spent his middle school years messing around on an Osborne 2 computer but wasn’t a coding prodigy. What he really wanted? To play football. He was the smallest guy on the team (he’s 5-foot-8), but he barely made it. The benchwarming didn’t kill him, and his description of it sounds kind of familiar: “I thought, ‘Oh, I’m here to support.’”

An earlier version of this story mischaracterized the Hayes family’s travel to Philadelphia.

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