But ever since Gurley and his wife, Amy, quietly sold their home in San Francisco and moved into a skyscraper in downtown Austin, Tex., he’s enjoyed more anonymity than usual. And his move back to Texas, where he and his wife are originally from, has largely gone unnoticed until I heard his name thrown around a couple times last week during a trip to Austin and some journalistic sleuthing revealed he had purchased a place. That subtlety, he says, was by design.

“My wife and I have been talking about this for 25 years. It wasn’t a statement. I wasn’t making a huge California-Texas thing. Others were, and I didn’t want to get caught up in that. I literally did not want to be a part of that narrative, because it wasn’t the reason why,” Gurley told me as we met for coffee, sitting across from one another in a red booth next to a picture on the wall with the words “we are all bums on strike.”

Gurley rarely gives interviews these days, but he sat with me for over an hour and opened up about both leaving San Francisco a year and a half ago and stepping back at Benchmark, one of Silicon Valley’s most prominent venture capital firms, where he spent more than two decades backing the likes of Uber, Grubhub, Zillow, Stitch Fix, Vudu, and a host of other companies. (Gurley excluded himself from Benchmark’s tenth fund in 2020 though he still serves as a partner of previous funds, attends Benchmark meetings, and holds 10 board seats)

Gurley says his portfolio companies, which include HackerOne, Nextdoor, GoodEggs, and Solv, require a lot more of his attention these days in the current environment, and meetings are taking up a lot of his time. But he’s dabbling in a few things in the background: Public stock investing. A book based on a speech he gave in 2019 about pursuing your dream job. He started learning guitar—his “COVID hobby.” And he’s doing some work with the University of Texas at Austin, where he went to business school, helping them with commercializing their efforts with entrepreneurs, he says. You might also see him at ACL Live, the Continental Club, or C-Boys Heart & Soul—where he frequents live shows.

It wasn’t Austin’s burgeoning tech scene that drew Gurley to Texas. In fact, he says he misses the intellectual spirit of San Francisco—and the conversations that emerged when he ran into people at lunch or at dinner parties.  “Everyone talks about Austin like an entrepreneurial place, but it hasn’t really delivered, I think, relative to the potential,” he says. Rather, Gurley says that returning to Texas had always been an “unofficial agreement” between he and his wife, and he likes Austin for its restaurants, live music, and walkability. He says he now spends time with a much more diverse group of people—musicians, people that own spirit brands, run hotels, or sell real estate. “I find it interesting: It’s just different, you know?” 

An empty top row

For someone as prominent as Gurley, he carries himself in a more understated manner than dozens of lesser-known investors I’ve grabbed a cup of coffee with. He downplays his own success, and he pays in good, old-fashioned cash. He’s curious about me, asking his own questions about where I live and about something I’ve written. He never shied away from any question I asked, but he didn’t volunteer anything about himself, either. I realized after our conversation that I had reached out to him on his birthday. He didn’t mention it.

When word got out that Gurley wouldn’t be part of Benchmark’s tenth fund three years ago, it was notable, even though other Benchmark partners like Matt Cohler or Mitch Lasky have also stepped back in recent years. At 57 years old, with a slew of successful exits behind him, Gurley had the kind of track record that would have welcomed him riding out the next 20 years and taking a paycheck from new funds. But Gurley tells me he wasn’t interested.

“Without naming names, I think there are VCs that have hung around too long, you know? I didn’t want to be that person. Does that make sense?” he says.

And particularly because of Benchmark’s unusual structure relative to other firms—an equal partnership where all partners have an identical cut of each fund’s management fees and profits—it didn’t feel right for Gurley to keep earning his share if he wasn’t going to be doing his share.  

“The venture business, if you want to be at the top, requires insane, remarkable hustle… You have to live in fear that the next Google is going to get funded by a firm that’s not yours,” he says. “Either you’re in there rowing as hard as you can, because we’re all a team, or you’re not.”

That said, he still has strong instincts about the future of tech. “If I were still active as a venture capitalist, I’d be looking at a lot of the vertical applications of A.I. I look at the coding stuff, and it’s insane… If you’re not using it, I think you’re probably writing your own death certificate as a programmer, because people are going to be so much more efficient. And the question is: What are other applications that have that kind of productivity boost or lift, and I think people are trying to figure that out.”

But in the end, it was a book by Steve Martin, Born Standing Up, that helped convince Gurley it was time to step back. “One day, [Martin] is in Vegas and he comes out, and the top row is empty, the first time he’s ever seen the top row empty. He quits the next day—never does standup again. And then he goes off and he does his banjo and his theater and his acting.… Like I said, I don’t think I ever played the stage, so I’d rather not say I’m the same. It influenced me. That notion influenced me.”