Two Drinks With Redpoint Venture Capitalist Ryan Sarver at Alta, His New Bar

I sat down for two drinks with Ryan Sarver — venture capitalist, hockey player and restaurateur — for a Re/code series called “Two Drinks With” (you can order kombucha, but I will judge you). Sarver, 34, talked about his dad-listserv OMGkids, feeling like a mob boss with his new restaurant, being excited for the new Valleywag, and being an investor in the kind of companies Valleywag skewers the hardest.

Settling into his bar stool for a bit of day drinking at Alta (his stool, because it’s actually his — he owns the place), Ryan Sarver rattled off everything that has happened this year (quitting Twitter, joining Redpoint, having a kid and starting the bar), and asked if we could make it five drinks.

He ordered the “Fashions of 1796”: Rum, rye, mole and blood orange. I got the “Seasonal Great Pumpkin”: Bourbon, orange, cardamon and pumpkin.

How’s he liking the new job?

“Startups — you go through this roller coaster every week,” he said. “Venture has smaller highs and lows. Not the same endorphins. But I like it.”

He continued: “I don’t think it’s for everybody. You need to be adventurous. You have to be ready for a lot of interesting flavors.”

Wait, what?

“The drink. The drink. A lot of flavors in the pumpkin,” he said.

Sarver is discovering what mob bosses have long known: Owning part of a restaurant is a lot of fun. An early employee at Twitter who helped develop its API, Sarver is now a partner at Redpoint, leading investments in Silicon Valley classics: Photo-sharing and on-demand convenience (specifically, Memoir and LuxeValet). He and Alta have become something of a social center for San Francisco’s mid-Market Street tech community, which is booming with new companies, thanks to a very generous tax break from the mayor’s office.

“Uber, Yammer, Square and Twitter are all here, and we’ve been the only restaurant in the neighborhood for a year,” he said.

Alta’s neighborhood, the Tenderloin, is going through a well-documented shift with scores of new tech companies coming in, but most of the changes (the artisanal espresso and sushi and yoga classes) are hidden within the tech startups, behind security guards.

The next era will usher in a fleet of new ground-floor amenities. The luxury apartment building Nema is opening a restaurant. Twitter is opening a ground-floor market. Half a dozen hip hotels and new bars are trying to squeeze in.

Our drinks came; mine in a silver goblet, his in a tumbler. Sarver continued talking about the difference between entrepreneurship and venture capital.

“In entrepreneurship, you have to be a no-holds-barred optimist — dedicate 10 years to something everyone thinks is going to die,” he said. “I mean, look at Twitter! People were always saying it was about to die.”

People are still saying that about Twitter, I added. He nodded, and we both took a drink.

“In VC, you have to balance pessimism and optimism — you have to say, ‘This will change the world,’” he said. “But also know that nine out of 10 companies fail.”

Which led to him talking about startups being so hot right now. He said he was excited for notorious satirist Dan Lyons to take over Valleywag, and asked if I had read Lyons in his previous gig as Fake Steve Jobs. (I’m of course not old enough to have done so, but onward.)

“Well, it was funny. Snark needs to exist!” Sarver said. “We all need to be critical of ourselves.”

It was funny that he brought up that particular blog. Sarver’s investments are, actually, exactly the sort that Valleywag specializes in mocking and many others hand-wring over (“Why can’t tech solve real problems?” writers often ask). Serious minds bemoan the photo-sharing apps and convenience services like on-demand valet, in which a uniformed but non-union and certainly not insured contractor comes running out from the ether to park your car.

“They take scooters, actually,” he said, referring to his portfolio company LuxeValet. “No running.”

Scooters. Of course they do. Ryan, you do realize that LuxeValet is why we can’t have nice things?

“Maybe. But listen, Uber started with Garrett [Camp] coming out of a club and seeing all the black cars and wanting to take one home. It started silly, and now it will change the world,” he said. “People hate parking. It’s a big market.”

God, maybe he’s right. We order another round of the same drinks.

He said he has all his business meetings at his bar now. I said, of course he does, because he’s a mob boss. He joked that he’ll build a secret room in back, and that the best part of his new role is being able to off people. (Am I at risk?!)

“There’s also interesting — oh, I hate the word, I hate it, but … there’s synergy between restaurant culture and startup culture. Chef Daniel [Patterson] creates 12 courses, and you’d never expect those flavors together, and he also has to scale for the whole restaurant,” Sarver said. “Founders are very much the same — can we innovate, and can we execute, and can we scale?”

The best part of the restaurant is that it gives him an excuse to meet people in other industries.

“The downside to San Francisco is it’s a very homogenous world — we’ve all read the same seven books,” said Sarver, who lives in a modern condo in the upscale residential Noe Valley neighborhood.

Sarver didn’t come from a particularly technical world. He grew up in Birmingham, Mich., playing hockey and working as a restaurant server and bartender, learning about the business from his uncle’s bar, The Landshark. His dad, a project manager at a heating, ventilation and air conditioning company, sold his motocross bike so he could buy the family’s first computer.

Sarver started taking coding contracts in high school, dropped out of Babson after one year, and joined the Boston tech community where he met his wife, Devon Biondi, who now works as a VP at Mashery. He started going to Burning Man (he’s gone five times), and officially moved to San Francisco five years ago, at age 29.

His left hand was all stitched up along the palm.

What happened?

“Oh, don’t put it in — it’s embarrassing,” he said. “I caught a puck in my hand.”

Were there no gloves? Sarver, who has been playing hockey since he was three years old, plays twice a week in the city’s Yerba Buena ice rink (without gloves?).

Three of Sarver’s friends walked into the bar, and Sarver introduced them all to me (all technologists, two CTOs).

“Oh, I see! It’s the beard committee!” he said to them in lieu of hello.

They all had enormous beards, the kind that’s grown over years. They started talking about the latest emails on their tech-dads email list, called OMGkids.

“We use [the listserv] to talk monitor specs,” said Sarver. “Baby monitors.”

This article originally appeared on Recode.net.