U.S. Markets closed

Venture investor on Trump: 'We are in absolute unmitigated crisis'

Rob Pegoraro
Contributing Editor

AUSTIN—Chris Sacca showed up at South By Southwest (SXSW) in one of his cowboy shirts and with plenty of cowboy attitude.

The Lowercase Capital investor and “Shark Tank” regular spent an hour in a Saturday-afternoon onstage interview holding forth—bluntly and often profanely—on issues ranging from his problems with President Donald Trump to Uber’s self-inflicted PR nightmare to what’s wrong with startup culture.

Talking Trump

Interviewer Alex Konrad of “Forbes” asked Sacca what keeps him up at night. After mentioning that he has a 1-year-old, a 3-year-old and a 5-year-old, he said, “I love my kids, but, yeah, they just keep different hours than I do.” And, he added, “The Trump thing is really bad.”

“We are in an absolute unmitigated crisis right now,” Sacca said. He was among the tech figures who signed last July’s open letter to Trump denouncing him as “a disaster for innovation,” but the concerns he voiced at SXSW went well beyond tech-policy specifics.

“The idea that we have a serial sexual abuser and a pathological liar in that office, I can’t get away from it,” he said while denouncing mainstream Republicans for enabling Trump’s “kleptocracy.”

Sacca did, however, find reason for hope in the groundswell of resistance against Trump, and in particular the Women’s March the day after his inauguration. “Some women just got together and [expletive] did it, they shipped it.”

And, he added, at least the election was not bought with campaign donations: “It was one of the very first times that total ad spend was decoupled from the result.” His hope for what can come from that: “It would be a lot cheaper for me not to have to raise tens of millions of dollars to elect progressive candidates who will raise my taxes.”

Why Uber’s in a world of hurt

Uber founder Travis Kalanick

Sacca, who was an early Uber investor, also teed off on a man almost as unpopular as Trump among some conference attendees. That would be Uber founder Travis Kalanick, who’s been under fire since a former Uber engineer alleged in a blog post that the company condoned sexual harassment.

“Nothing about that story shocked me at all,” Sacca said of the former engineer’s allegations that she was propositioned by her manager, a supposed “high performer” whom higher-ups failed to discipline. “I couldn’t believe the HR team responded like that,” he vented. “Automatons could respond better.”

Sacca noted that he hasn’t had “a speaking relationship” with Kalanick since 2011, but pointed to issues he’d seen back then, such as Kalanick’s dismissive response to early complaints about “surge pricing” increases during times of high demand.

“We had a guy who paid $187 to go one mile in New York City,” he recounted. “Travis’s response was ‘suck it up, surge pricing is here to stay.’ ”

(And yet, he added, “The people who complained loudest on Twitter, their usage of Uber accelerated.”)

Kalanick paid the price when people rejected his defenses for his now-ended participation on Trump’s business-advisory council. “Travis hasn’t earned the goodwill of the country, so everybody went apeshit on him,” he said.

Sacca allowed that Kalanick’s pledge to get leadership help by hiring a chief operating officer—hopefully “a kick-ass woman”—shows some maturity.

Startup culture and mistakes made

Sacca did not just have strong words about Uber. Much of the startup culture is filled with “a lot of posers, a lot of entitled people, a lot of people who should be working in some other … industry,” according to Sacca.

Sacca denounced the trend of venture capitalists investing only in products they use: “There’s like eight Ubers for jets and nine Ubers for yachts, and they’re all going to fail.”

He also criticized the lack of gender diversity in Silicon Valley, noting that even when women have spots at the table their advice may go ignored. Case in point: his own failure to follow up on one Lowercase employee’s suggestion to invest in Pinterest.

Sacca did, however, pass on Snapchat (SNAP) early on—he called its supposed initial emphasis on sexting “the least healthy thing in the world”—and has no money in it. “Aways be proud of the things you invest in,” he counseled. During the Q&A part of Sacca’s talk, he voiced his skepticism of virtual reality—“It just deprecates every other sense we have”—but complimented augmented reality, in which a phone or tablet overlays information on its camera’s view of the world.

A Georgetown University graduate, Sacca confessed that when he sees people wearing shirts with the school’s logos, “I have found myself hovering my hand over them to see which year they graduated.”

His own customary attire is a silver-embroidered cowboy shirt. An audience member asked about that, and he explained that each one is a little different from the other and, unlike his speech, can contain some subtleties. He pointed to his attire and said mysteriously, “This one may or may not have secret messages.”

More from Rob:

Email Rob at rob@robpegoraro.com; follow him on Twitter at @robpegoraro.