NEW ORLEANS — “Shark Tank” star and longtime tech investor Chris Sacca (who put early money into companies including Twitter and Uber) arrived at the Collision conference in New Orleans this week after surprising the industry with his announcement that he’s retiring from the venture capital business.
In a two-hour on-stage interview with CNN’s Laurie Segall, Sacca let loose on everything from his views on how to oppose President Donald Trump to his misgivings about Twitter’s strategy, his thoughts on the controversies at Uber and its treatment of women in the tech industry — and plans for a new TV show on ABC about a fictionalized version his life.
Continue reading for highlights from his talk.
On the power of the protest movements that have grown up in the wake of the election: “I deeply believe that this wave of taking our country back is going to be leaderless and decentralized. And that’s scary and yet that is the poetry of the whole thing. For somebody who is used to hierarchy and structure and power and influence, that’s unsettling in a traditional sense. And I can tell my discomfort with it is filled with all kinds of bias. This time, no-one’s in charge and I think that’s why it’s going to work.”
On the Trump tax plan: “The United States … is the greatest nation on Earth and I believe there are things that make us special — and one is this grand democratic experiment. But we’re starting to realize that it’s an experiment and we can’t take it for granted. We’re also starting to realize that so much of this is built on norms and customs and tradition and mutual respect and honor. When you have people in power who are willing to abandon all of that for a tax cut, I really worry about the plight of this country. And I say that as a person who, under the tax plan [President Trump] just proposed, will make hundreds of millions of dollars more as a result. And I think that is one of the most unjust things that’s going to happen in the history of this country.”
On the early promise and power of Twitter: “Twitter in the early days was fun. And then there were the days when it started to look kind of powerful. The State Department called Twitter and said, please don’t do that scheduled maintenance you were going to do. Back then, to maintain your website you had to turn it off for a while … They said, the middle of the night for the U.S. is the middle of the day in Egypt, where all these kids are organizing these protests and the only way they are able to organize is around Twitter. It was like, Oh my God, we are fomenting revolution.”
On his disappointment with Twitter’s current strategy: “Twitter just got over-run. Not just by Russian troll bots and stuff like that, but by spam and by haters. And they were empowered. Twitter was like the biggest comments section in the world. There wasn’t any cost to being a jerk. Twitter’s value is determined by how many active users they have. So there’s a financial disincentive to kick a bunch of people off the platform. I’m not saying that’s why they make so many of these decisions, but it’s hard to make good, ethical calls on who is hateful and who’s not… I think they have just been paralyzed by it, frankly. They have all the world’s best content – no matter who you are, there is sh*t you would like and be intrigued by, be excited by and be compelled by on Twitter and they do the worst job in the world of actually showing that to you.”
On the struggles currently facing Uber CEO and co-founder Travis Kalanick: “Uber is truly an adolescent company. It’s in that stage of development. I think Travis is materially changing right now, for the better … It’s fragile. Travis is one of my closest friends. We stopped talking for years and years for things not unrelated to this mess. But I think that Travis is in a very vulnerable and introspective state right now in a way that I’ve never seen him — for the good. For the first time, maybe ever, he’s really acknowledging the places he could use help. And that’s fantastic. He’s starting to take responsibility for his broader role and the consequences for this company and its culture and that’s great.”
On harassment and unfair treatment of women in tech companies and how it relates to the problems at Uber: “It’s pervasive and I think Uber is going to be front and center taking the slings and arrows for this, deservedly so. I also think they are going to be front and center for doing what they can to make up for decades of this bullsh*t.”
On how he felt to know that a fictionalized TV series based on his life was being developed by ABC and that Jordan Peele was being offered the chance to play him: “Jordan Peele! Yes! It was like I win either way. Either I get Jordan Peele to play me, which is legendary, or I get to try and do this myself…. Jordan passed, which I’m still a little hurt by, but I think acting and playing yourself is hard. Zach Braff is my costar, as well being the director, so it’s absolutely amazing.”
On why he’s retiring from being a venture capitalist: I wasn’t put on the Earth only to be an investor. That wasn’t my only thing in life. The problem is that as you get good at something and you keep getting better at something, more and more people just know you as that and they have you in that box. … When I was 20 years old, I was living in Ireland, going to school in Cork, there was this girl in my film class that I was kind of flirting with. We had this notebook that we passed back and forth. We would write 10 questions and then pass it back while we were supposedly paying attention. Then we’d answer 10 questions and write 10 new questions and pass it back. And couple of years ago, my wife and I found this in my garage. We opened it up and started reading it. One of the questions was ‘what do you want to be when you grow up?’.
“So, there I was – 20 years old, living in Ireland and I’d never heard the word venture capitalist. But I’d said that I wanted a job that involved a lot of negotiation, a lot of yelling at people on the phone and for it to be high-risk, high-reward. I will put it all on the line, I will probably do it from some scrappy place like an empty warehouse or something like that. I’ll do it halftime from the mountains and halftime from the beach. I’ll be the best there ever is at it and whatever it is that I do, I will quit when I’m 40 to do something else I really deeply love. So I was 39 when I found that. And my wife and I had some “holy sh*t” faces when we looked at each other (after finding the old notebook). We had already started planting the seeds for walking away from the business. So it was like a time capsule from my 20 year old self telling me to not forget that there’s more to me and my life than just this one thing.”