Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245

I believe if Travis and Emil had stayed at Uber, Uber would be a trillion-dollar company by now. His true vision for Uber was to replace car ownership, and it was at that moment I realized, “Oh, the TAM is trillions.” We were actually full steam ahead, but things started to go wrong. We had the wrong venture capitalists on the board, unfortunately, in my opinion. That was Bill Gurley at Benchmark.

We found out in our investigation that he hired private investigators and had weekly meetings about how to get rid of Travis. That week, Travis tragically lost his mother in a boating accident. Benchmark and Gurley decided to go after Travis.

Shervin, I’m so excited for this. I’ve wanted to make this one happen for a while, so thank you so much for joining me.

1. Mother’s Impact Getting Into Tech

I’d love to start with a little bit of context. I’m actually going to start, if it’s okay, with your mother. I’m so sorry for her passing, but I know she was also incredibly impactful in your getting into technology. Talk to me a little bit about how she influenced you getting into technology as a starting point.

Absolutely. Thank you. My mom passed away last Wednesday, and we’re going to have her funeral in a few days. She was just the most incredible human I’ve ever met. She was a teacher for 14 years in Iran, and when we escaped the revolution and came to America, she started all over again.

We came with $35. We had to escape, and we started with nothing. My dad drove a taxi while getting his PhD. My mom was a maid and worked two jobs as a cafeteria worker and a maid. I used to go clean rooms with her, so it was the classic American Dream story.

She took computer programming classes at a college in Maryland while I was a kid, and she would take me to her classes. This was when they had the paper with the holes in it—you punched the holes, and that was how they coded in the 1980s. I got to see that, and then I saw the Apple.

I begged my mom and dad for an Apple. They worked overtime for 3 months to afford it. Back then, it was around $3,000, which was a lot in 1985 or 1986. They bought me my first Apple IIc, and I wrote my first code on it. That changed my life.

Later, she secretly put a laptop on her credit card when I was at Berkeley and didn’t have enough money to get one. I always said that she was my angel, my first angel investor, and my first believer. She really taught me how to dream in color.

2. The Uber Story and Joining Menlo: How It All Started

I’m finding this process of grieving profound. I see her now in ways that I couldn’t see her when she was alive. Mothers are the most important people. I wouldn’t be anywhere without my mother.

I walk 2 miles a day with her, and it’s the sane space in my week. She’s also expensive—she loves Chanel—so there are downsides to everything.

Listen, dude, I want to go to the Uber story, and I want to go to your time at Menlo. How did that come to be? I’m going to leave it deliberately vague and open because I want you to lead the way there.

It was a great journey. I started my first company, WebOS, in my senior year of college, and that’s when my mom bought me the laptop. I was working a night job as a security guard just to make enough money to start my company.

I had this little LG laptop with a dial-up connection. While I was on the security job all night, I was working on the startup as well. At WebOS, I started recruiting really young talent because I was young, and at the time, the greatest developers on the internet were really young.

There were 15-year-olds like Anthony Casalena, who’s the founder of Squarespace. I realized that I had an eye for talent, and that later led to meeting Travis many years later and getting the sense that he was different.

3. Meeting Travis Kalanick

How did you meet Travis? Take me to that meeting.

I met him because Sheryl Sandberg was a mentor of mine. I was building Facebook apps and iPhone games for one of my first companies. Sheryl read an essay that I wrote about entrepreneurship and reached out to me on her own. She asked if I could do lunch.

She had just joined Facebook and wanted advice about the App Store and what percentage they should charge. I shared that Apple charged 30%, so they could probably charge 30%, which is what they ended up doing. We would meet once a quarter, and she was a great mentor.

Then I was selling SGN, and she told me, “Shervin, you should go into venture. You’ll be disruptive.” I didn’t think I had a seat at the table, but she sent an email to 5 top VCs the next day without telling me.

I haven’t seen the email, but I heard it was really great because I started getting recruited. I had an offer from Kleiner Perkins and an offer from Menlo, and I ended up going with Menlo. That really was the beginning of my venture career.

I’d been an angel investor before that and had invested in Facebook and other companies. When I started at Menlo, I hit the ground running. In my first 90 days, I closed Uber, Warby Parker, Tumblr, and Machine Zone.

It was a really fast start. On the whiteboard, I had a list of companies. This was June 2011, when I started at Menlo. Uber was at the top of the list. Airbnb was on the list, and Square was on the list.

This was an amazing time in Silicon Valley because these companies were just starting out. No one had heard of them. I was at Lowercase as a seed investor, and Naval Ravikant introduced me to Travis over email.

I went and used Uber for the first time. This was when there were hundreds of cars in San Francisco, and Travis and Garrett Camp had started the company. As the son of a taxi driver in Washington, DC, I knew a little bit about the taxi market, so that helped me win the deal.

I chased Travis even before Menlo, for a year. I was trying to meet him, and he was difficult to get to. I asked Matt Cohler, who was a longtime friend, and Matt promised to say something to him.

I waited for that, but meanwhile, I decided, “You know what? The answer is always no until you ask.” That’s one of my mantras. I basically bombarded Travis with references.

Drew [likely Houston], who’s a dear friend, Sheryl Sandberg, and Julius Genachowski were all telling him, “You need to meet with Shervin.” Travis has publicly said that he met with me because he had no choice—he had so many people telling him that he needed to meet me.

Matt called me in August 2011, 6 months after Benchmark did its Series A with Uber, and said, “We just had our board meeting. We’re going to raise the Series B. Can you meet with Travis tomorrow?”

I went to Uber’s first official office and met with him at a table that he later gifted to me as our deal table and signed, which was very kind of him. We hit it off. We met for 2½ or 3 hours and realized there was a lot of connection.

I was in the chase for the deal. Then I got a call from Travis. He called me “homie” at the time. He said, “Hey, homie, I really wanted to do this deal with you, but I have to go with this other firm.”

I didn’t know which firm it was. It turned out to be Andreessen Horowitz. My reaction, as a founder first and not as an investor, was, “Congratulations. I totally understand. If anything happens in diligence, just know I’m 100,000% behind you. You have a strong backup, so negotiate with strength.”

I’m really glad I said that because a few weeks later, I was in Africa giving a keynote for President Obama’s Global Entrepreneurship Summit. I was in Algeria and got an unknown call, which I never answer, but something told me I needed to answer it.

It was Travis. He said, “Hey, homie, you remember what you said 2 weeks ago? Is that still true?” I said, “Absolutely, it’s true.” He said, “Can you meet me in Dublin, Ireland, tomorrow?” I said, “Absolutely.”

I got on the plane, which led to another one of my mantras: always get on the plane. That’s made all the difference. Make the effort, show up, meet with the founder in person, and break bread.

I flew to Dublin, and we walked the cobblestone streets and had a pint. It was there that he told me his true vision for Uber, which he kept close to his chest at the time: to replace car ownership.

That was when I realized, “Oh, the TAM is trillions.” All my competitors were basing their models on taxi companies and black-car companies and weren’t realizing, “No, no, no. You’re turning every car into an iPhone. You’re creating a network machine on wheels.”

That leads to a platform and a two-sided marketplace. I ran to my hotel and wrote a term sheet at a $290 million valuation. I texted him the term sheet, and he didn’t answer.

I waited for an hour, thinking, “Oh, no. This is the worst. Is he shopping it?” I texted him again and said, “$300 million.” For the first—and I think the last and only—time I’ve ever seen Travis not negotiate strongly, he said, “No, $290 is fine.”

I ran straight to his hotel room. I have a picture I’ll send you of us at the door, signing the term sheet for $20 million at the time. Later, I got another $65 million through a secondary for Menlo.

That investment is worth almost $7 billion at today’s prices. It was one of those once-in-a-lifetime investments. $26½ million turned into around $6.7 billion at today’s prices.

You did this deal as part of Menlo, correct?

Yes.

How long were you at Menlo?

I was there for 18 months, and then I became an adviser for a year.

You get where I’m going with this?

Yes. It was a good ending, though. It was a good ending.

I worked out an advisory agreement. Because of what I had done, they agreed to give me increased carry deal by deal. Instead of getting carry in the fund, I asked for carry in every deal that I did because I had a lot of faith in those deals.

That turned out to be great. I got more carry than I would have gotten in the fund by agreeing to do deal-by-deal carry. That was a huge thing.

Then, because I was very involved with Uber, I was on the board as a board observer. Travis was making me a strategic adviser after I left Menlo to start Sherpa Capital.

4. The Future of Venture Capital

Before I started Sherpa, he allowed me to buy secondary shares from another early person. I sold all my Facebook shares, which had gone public at around $53 or $58 a share, and put it all into Uber.

I bet everything I had on it. If Uber didn’t work out, I would have been bankrupt.

At what price was this Uber investment?

It was effectively 33 cents a share. Based on today’s prices, it would be $33 a share.

Wow.

5. Being Strategic Advisor at Uber

I had my direct exposure, and I had my deal-by-deal carry. That worked out, thank God. I was suddenly shit-scared. $1.4 billion of carry was just like, “No, bad luck.”

We’re now at the point where you’re his right-hand man and strategic adviser. Take me to that time.

It was one of the greatest experiences of my life. Watching an entrepreneur of Travis’s quality and being able to work with him very closely was extraordinary.

What do you think makes him so good?

I’ve been lucky to work with what I call foundational founders—really exceptional, highly intelligent founders. I got the experience of sensing that kind of intelligence because I was in a magnet school with some brilliant minds.

It was a math, science, and communications magnet school. They tested a bunch of kids, and 100 of us were picked. We were the guinea pigs. I got bused for 1½ hours each way every day, waking up at 5:00 in the morning to go to the school in Silver Spring, Maryland.

I met all these brilliant kids—kids who would remind you of a young Elon or a young Travis. A lot of them ended up helping build Google or founding Danger. These were my fellow students at the magnet school.

With Travis, I immediately thought, “He’s extremely brilliant.” One story I like to tell involves Yuri Milner, who has been a great mentor. I met him when he first did the Facebook deal, and that’s how I met Daniel and Shaq [?] through Yuri.

We went on a meeting and trip together, and we all hit it off. I brought Yuri into Uber. I brought a bunch of people into Uber, and I can tell you that story.

At the same 33 cents—what sort of price? A $30 million valuation?

Yes, exactly. Yuri and Travis became close, and we were at an Oscars party that CAA was hosting. Yuri, Travis, and I were there.

Yuri, who’s a mathematician and physicist, had this hobby of giving Travis really hard math problems. He gave him a math problem verbally as we were sitting at this Oscars party.

Travis famously paced around all the time. There was a track at the Uber office, with a path he would walk back and forth on. He would think by walking.

He walked back and forth, figuring out the problem. A lot of my friends in the magnet school were the types who could see numbers in their heads—brilliant minds who could calculate things. I could see him looking up and calculating.

He came back in 2 or 3 minutes and gave the equation. Yuri said, “Almost.” Travis ran off, walked around, and came back 2 minutes later with the right answer, all in his head.

That’s the kind of brilliance he had. I’ve been lucky to invest in SpaceX, become friends with Elon, and later do Hyperloop. I got to witness what an exceptional and brilliant mind can do.

These people aren’t just 10x engineers. We talk about 10x engineers, but these are 1,000x humans. I’ve learned over time that it’s worth waiting for the 1,000x founders and investing in the future Travises, the future Elons, or, in the case of Airbnb, the future Brians.

There are a lot of suggestions that Uber’s culture was, bluntly, incredibly hard-driving, incredibly ruthless, and pretty tough to be in, to be quite frank.

I don’t agree with that. I think Uber’s culture was excellent. They were achieving greatness. They were making history. It was the fastest-growing company in history.

You can’t get there without being fierce. You can’t get there without working extremely hard. You can’t get there without having really intelligent people coming together as one team.

Where were you not fierce enough? Where do you look back now and think, “We should have been fiercer”?

Lyft. We could have been much fiercer on Lyft earlier. It was the one time I saw Travis hesitate.

Zimride had launched, and I had passed on Zimride. Then they saw Uber launch with black cars, and they launched what became UberX later. We were already working on launching UberX, but Lyft beat us to it.

They launched Lyft with the pink mustaches and people’s cars. They weren’t black cars, and they were illegal because they didn’t have approval from the San Francisco Taxi Commission.

For 6 months, Travis was telling the taxi commission and the city government, “These guys are illegal. Why are you allowing this?” Instead of launching it ourselves, we waited.

That was the first and last time he ever made that mistake. In those 6 months, Lyft took off. They ultimately ended up with around 30% of the US market share. They never expanded globally.

It’s funny: after losing the Uber deal, Lowercase ended up doing the Lyft deal. Travis and Emil were close to acquiring Lyft, but Lyft wanted too much ownership, so luckily that didn’t work out.

I remember taking the first 100 Lyfts to Google for Travis and talking to the drivers. You sat in the front, did the fist bump, and all of that. They were cute and onto something. They beat us to the punch by 6 months, and that cost us 30% of the US market at the time.

Why were you too slow?

I was involved in the beginnings of Uber China. There’s a good story about getting TPG and David [likely Bonderman] in there. I can tell that story.

Before we unpack that, you mentioned Emil. I wanted to take this stage by stage. Emil obviously had a big role to play, and I hear you were part of recruiting him.

Yes. Travis came to me and said, “I need to recruit a number two. This guy Emil Michael—everyone speaks really highly of him. Can you help me recruit him?”

Travis and I divided and conquered. We both worked on getting Emil, and we were really close to getting him. On one of the calls, Emil said, “Listen, I have these other offers, and they have titles like president of Klout or president of Jawbone.”

He wanted a president title or chief operating officer title. Travis didn’t like titles, so he said, “Tell him he can be president of himself on the business card.”

How kind of you to relay that information directly.

I did not. Emil took the president of Klout position. I called Travis and said, “He took this other position, but I’ve experienced losing someone and getting them later. If they’re special enough, you want to get them later anyway.”

I said, “I think I know what to say to him to plant the seed for later.” Travis asked, “What are you going to say?” I said, “This was an IQ test, and you failed it.”

I would never say that to Emil now because he’s one of the smartest people on the planet, but I said it, and it worked. Emil told me that for 6 months Uber was going like this, while Klout was doing okay but not like Uber. He said, “Damn it, I failed the IQ test.”

Later that year, I organized a trip. I had introduced David [likely Bonderman] and Coulter to Travis, and we were working on the Series C. Google was leading the round.

I said to Travis, “We should get Bonderman on the board and get TPG as a counterweight to Google. If they’re on the board, you need a counterweight.”

David [likely Bonderman] could also call any leader in the world. He passed away last week, on the same day as my mother. He was a great mentor and a great investor.

6. Uber China: The Challenges and Triumphs

We had breakfast, hit it off, and then they invited us to go to the Oscars with them. We got on the plane, flew to the Oscars, and then they said, “We’re going to Asia—5 countries and 6 cities. Do you want to come with us?”

Travis said, “Sure.” So we got on the plane again. That was the mantra: get on the plane. We did 5 countries in 6 days.

I think it was the first time Travis had been in China. We introduced him to the CEO of Baidu, and that led to the joint venture that led to Uber China.

Then, on that trip, we went to Hong Kong. We were at a restaurant with David [likely Bonderman], Travis, Coulter, and me. I went to the bathroom, and Emil was in the stall next to me.

I said, “Emil, what are you doing here?” He said, “I’m here for a wedding.” I said, “We’re all here, Travis included.” He came over, and that was it. We closed him that night.

He became chief business officer, and the rest is history. He architected the $5 billion raise, had a massive impact on Uber’s trajectory, and became Travis’s right hand and sparring partner in building Uber.

You mentioned Baidu and China. Was that a good joint venture? Was China good for Uber?

I would say it cost a lot of money to compete with Didi and the other companies. Essentially, these companies in China were favored.

It was remarkable that we got permission to launch in the first place as a US company. Google and Facebook were never able to launch in China, so we were one of the first American-invented consumer internet products to launch inside China.

That was remarkable. Given the size of the market, I thought it was worth being present as part of our global expansion. We also mitigated the risk by having a joint-venture partner as strong as Baidu.

Our fund put $50 million into the beginning of Uber China and later put another $50 million into Didi when they merged.

This was when you were doing Sherpa?

Yes.

How big was Sherpa?

Our first fund was small—$153 million. The second one was around $175 million.

So, to put $50 million in, you were pretty big.

One thing I did, as a little bit of venture-capital history, was push special-purpose vehicles hard. VCs didn’t like SPVs back then, so I was really the first person to push them aggressively.

We ended up doing $200 million of SPVs for Uber on top of those other investments. We also brought our LPs in to co-invest. TPG was one of our LPs at Sherpa, so we brought them into Uber, and they put in around $83 million.

Google didn’t want to share. They wanted the whole $250 million allocation, and Travis didn’t want more dilution. My solution was what are called Waverly loans, which no one had used in 30 years.

I used Waverly loans to structure my secondary purchase of shares from an early founder when Travis allowed me to become an adviser and direct investor after I left Menlo.

The way Waverly loans work is that they’re like a tax-free loan to a founder, exchanged for shares later. You retire the preferred shares you’re replacing with common shares, so it’s basically a swap.

I popularized that. The TPG solution was that I introduced them to Waverly loans, and we did the largest Waverly loan in history—$83 million—to buy G Camp’s shares for TPG.

He sold out fully?

No, he held on to a lot. He’s a multibillionaire.

I don’t know Garrett, but my heart just sang for him.

TPG made close to $2 billion on that $83 million.

They must be very grateful to you. I cold-emailed Bonderman 11 years ago, and he jumped on a 30-minute call with me when I was 17. I always remember thinking, “What a dude.”

He was amazing.

7. 15 Billion Raise

We now have Emil on board. You mentioned the $15 billion raise. Take me to that.

We were looking at global expansion. We wanted to expand to 800 markets and dominate the world. At the time, the world was up for grabs, and no one was better at what we were doing than Uber.

The idea was, “We raised this round with Google—that was the Series C—but we want to do a much bigger round at a much higher valuation.” Emil kicked off that fundraising, and this was where the partnership really took hold.

They would line up the investors outside so they all saw each other in the hallway. Then they would have a tight deadline: “We’re raising this much, and we expect term sheets by Friday.”

It was a very efficient process. The Series D, about a year after the Series C that Google and TPG did, was at a $17 billion valuation. We started off at $10 billion or $11 billion, and Emil negotiated up to $17 billion because there was so much competition for the deal.

Kleiner Perkins came in, with Mood Rowghani leading that deal. I think they put in $100 million in that round. Then came the SoftBank raise and the much bigger raises.

Ultimately, we had billions of dollars to expand around the world. That led to the market share Uber has today, with Uber Eats and Uber itself.

Can I ask whether that was a necessary evil? Was that much money that early required to achieve what Uber achieved, or, in retrospect, was it too much too soon?

It was what was required. This is atoms and bits. You need cars, people, labor, and millions of them all around the world. You need to subsidize it to get the market share going.

I went to most of the city launches around the world, and we came up with a whole playbook, including getting celebrities involved. In my round, I brought most of Hollywood into Uber.

Guy Oseary likes to joke that I’ve made more people in the music industry money through Uber than they have made in the music industry. I brought in Scooter Braun, Troy Carter, Ari Emanuel and WME, Sophia Bush, Olivia Munn, and many others.

They all invested in that Series B at 33 cents. They helped us because, when we went around the world to launch, it helped to have a celebrity be rider zero or rider one.

I brought Edward Norton into Uber. For the Los Angeles launch, we decided that rider zero would be Travis’s parents, his mom and dad. I was having dinner with Edward, and I said, “Why don’t we have you take an Uber SUV with your surfboard to the beach and be rider one?”

He said, “Absolutely.” He was our rider one. We did a blog post about it and replicated that playbook all over the world.

8. The Beginning of the End: Betrayal by Benchmark

In India, we would launch with a Bollywood actor or a cricket player. I absolutely loved that.

We have this continuous meteoric growth. We have the $15 billion, and it’s going through the roof. Where do things start to fray? This is the dream story to date.

The business didn’t fray. The business was executing at the highest levels of excellence. The business was not fraying; we were actually full steam ahead.

What went wrong was that we had the wrong venture capitalists on the board. Unfortunately, in my opinion, that was Bill Gurley at Benchmark.

I haven’t told many of these stories. I waited until we found out exactly what happened. Gurley was pressuring Travis and Uber to go public as soon as possible. He was pushing that incessantly.

He wrote a blog post that didn’t name Uber but talked about how companies needed to go public. At one point, Travis stopped responding to Gurley because he was being annoying.

Gurley is a 6-foot-1 Texan who’s used to getting his way and being listened to. When Travis stopped responding to him, we found out in our investigation that Gurley hired private investigators and held weekly meetings about how to get rid of Travis, starting in January 2017.

When the Susan Fowler blog post happened about a month later—

Remind everyone what the Susan Fowler situation was.

She was an engineer who had a bad experience with a middle manager, her engineering manager, who harassed her. She wrote a blog post about it.

I remember that day vividly. Travis and I were in Malibu. Every summer, we rented a house in Malibu with some good friends. We had this last innocent weekend in Silicon Valley: laughing, relaxing, and recovering after working really hard.

I had just flown in from China. The blog post happened, and someone walked in and said, “Hey, guys, you should take a look at this. It has 3,000 likes.”

We read it, and then Rachel Whetstone called. She was a political operative whom Gurley had advised Travis to hire. It turned out that 2 political operatives from Google had been hired, and Rachel was one of them.

Rachel immediately said, “We need to hire Attorney General Holder”—Obama’s attorney general, who had recently stepped down and was at a big law firm—“to do an independent investigation of workplace culture.”

I looked at Travis and said, “It’s a trap.” He was in a conversation, so he didn’t hear me. It went over his head, but he agreed to it.

That was the beginning of the end because you’re giving up a lot and making yourself very vulnerable in that situation.

Why are you becoming vulnerable? Because you’re opening up?

If someone has a nefarious strategy to get rid of you and you agree to an independent investigation by the attorney general of the United States, they’re going through everything. It can be turned into something that it’s not. Things can be manipulated.

Six months later, the report was supposed to come out. That week, Travis tragically lost his mother in a boating accident. His mother and father were in a boating accident, and she passed away. His father was also close to death.

In the middle of that tragedy, Benchmark and Gurley decided to go after Travis. They delayed the release of the report. The report, by the way, didn’t find anything wrong that Travis or I had done. There was nothing in it about him directly.

The recommendation was to hire Sheryl Sandberg as chief operating officer. Travis was in Chicago the week he lost his mother, recruiting a chief operating officer, dealing with the tragedy, and trying to take care of his company.

Matt Cohler and Peter Fenton showed up at his hotel room and surprised him with a letter signed by 5 early investors, essentially saying, “You need to step down as CEO.”

Who were the other investors?

I think it was Lowercase, First Round Capital, Menlo, and obviously Benchmark. I think that was it.

They said, “If you don’t resign, we’re going to release this letter publicly to the press.” Travis was in the room for hours and hours trying to decide what to do. He ultimately agreed to step down, which I highly regret.

Did he have a choice?

I now look at how Sam Altman handled his coup over a weekend and how he galvanized the employee base. I think he learned lessons from what happened in the past to Steve Jobs and Travis.

He was able to find his way back when he thought he was gone. Travis could have pushed back and said, “Release the letter.”

Do you think he could have pushed back and said, “Release the letter”?

I think he was in a very tragic week of his life. He had lost his mother, and I’ve just lost my mother, so I understand the grief you’re going through, especially in a tragedy like a boating accident.

He was very vulnerable, and they pounced. That is unbecoming. It’s not the type of behavior any VC or investor should engage in. They took advantage of the situation, and it worked. They got him to step down.

What happened next got me directly engaged in the battle, in what I call the Uber War. In early August, they sued in Delaware court after they had already gotten rid of Travis. They sued to get rid of him and his 2 board seats that he had received but hadn’t appointed yet.

They wanted effective board control. I hired Quinn Emanuel and John Quinn, who is one of the fiercest corporate litigators in the world. I countersued Benchmark.

I flew to Delaware, landed, and went to this little courthouse. It made me fall in love with the American justice system because the entire corporate legal system is held up by this tiny little town and little courthouse.

We went into the courthouse and made our arguments. The judge found in our favor and rejected Benchmark’s attempt to get rid of the 3 board seats.

I remember calling Travis and saying, “We won. Your 3 board seats are protected. Appoint them now.” He appointed Ursula from Xerox and the former CEO of Merrill Lynch.

Then, 2 weeks after I won the case, I found out through our investigation that there was a firm called Fusion GPS. It was the firm that famously did the Russian dossier against Trump—the fake Russian dossier.

It was essentially a political-operator firm made up of former journalists. It was the weaponized arm of the Democratic National Committee. They did the Russian dossier against Trump to make him lose to Hillary and cause trouble during the first term.

These were really immoral people. We found out in our investigation that 2 weeks after I won the case, a founding partner of Fusion GPS was sitting at a café in Washington, DC, with a reporter from Fast Company, carrying a memory stick and a fake police report from London about me.

They gave it to the reporter. We filed lawsuits to conduct discovery under Section 1782, which allows you, if you have a British case, to sue in federal courts in the United States. It’s a provision that allows discovery in US federal courts for a case in the UK.

I hired the top expert on Section 1782 and won against Fast Company. We got discovery of the emails. There were multiple emails from the London police telling the reporter, “This is not our report,” and he still reported it.

It threw my life into a tailspin.

How so?

They accused me of something awful that I never did and was innocent of. They fabricated a police report to get reporters to do it. Once the first publication did it, every other publication did it.

When we countered with a letter from the London police saying, “This is not our report,” I quelled it at the time. Then they continued with 5 anonymous accusations.

This was in the middle of the Me Too movement, in October or November 2017. I realized that if I didn’t take a leave of absence or step down, they would keep attacking until I did.

They were trying to stop me because I had organized a shareholder group with people like Ron Burkle, who had invested in Uber along with Ashton Kutcher and Guy Oseary through their fund, A-Grade. There was also Adam Leber, a top music agent, and other investors.

We were trying to counter-sue and fight what was happening. I was meeting with Rajeev Misra about buying Benchmark’s stake because I was publicly going on CNBC and saying, “We’ll buy Benchmark’s stake. If you don’t want out of the company, let’s get you out. We’ll buy you out at a great price.”

9. The SoftBank Investment & Leadership Changes

Why was that not an option? People want liquidity. We see this more and more with secondaries and late-stage secondaries today. Why didn’t you just say to Benchmark, “Bill, you want liquidity. I get it. I’m an investor, so I understand that you want liquidity. We’ll buy you out at a great price”? Why wasn’t that an option?

Ironically, Travis and Emil started the SoftBank conversation. The ultimate $12 billion investment from the SoftBank Vision Fund came from conversations they started.

Then Travis was removed from Uber, and Emil was removed at the same time. Two of the greatest minds in Silicon Valley were taken out of the company. This was the greatest value destruction since the firing of Steve Jobs at Apple.

It was a massive mistake. If you look at Tesla, it’s a trillion-dollar company now. I believe that if Travis and Emil had stayed at Uber, Uber would be a trillion-dollar company by now.

They brought in Dara Khosrowshahi, who’s a dear friend. I call Dara the great stabilizer. He has taken Uber to a $175 billion market cap, which is great, and made it profitable. He’s done all of those things.

Travis was working on ideas like self-driving and automation. He was in pole position at the time. I saw him speak in Saudi Arabia at the FIA a couple of months ago, and they asked him what he would have done if he had stayed at Uber.

He specifically talked about AI. If you look at all the great things happening in AI and the paper that came out in 2017, we were on top of that. We were working on those things.

He would have been one of the great AI and automation entrepreneurs in the world. He would have applied his intelligence to Uber in a way that nobody else can. Nobody can do what Elon is doing, and nobody can do what Travis is doing, no matter how great you are.

These are rare, Nobel Prize-winning founders. Uber would have been a trillion-dollar company.

In their greed to go after their current winnings of billions of dollars—single-digit billions—Benchmark and the other investors made a critical mistake. Look at what others who are in Tesla or SpaceX are experiencing right now: they stuck by an exceptional founder with a strong personality like Elon.

If Benchmark had kept its ownership—let’s say 10%—it would have had $100 billion to give to its LPs at this point. If they had simply not done this, Uber could have been a trillion-dollar company.

I always like to see both sides. Gurley still scares the shit out of me at 6-foot-10.

He does. I respect him as an investor, candidly. Is there a justification for it? I try to put on my investor hat and think, “If we haven’t returned cash to investors in a long time and investors are pressuring me to put liquidity back in the pot, do I need liquidity?”

Is there any justification?

No. Absolutely not. The answer is no.

Benchmark invested in March 2011 at, I believe, a $50 million pre-money valuation. They put in $10 million, so they were sitting on a massive win. But they had only been in the company for around 6 years when Gurley went after Travis.

Typically, it takes 7 to 10 years to get to liquidity. It wasn’t in the zone where you would say, “It’s been 10 or 12 years and we don’t have liquidity.” Give him 4 more years.

If they had waited 4 more years, this would be a trillion-dollar company. When you look at the impact it would have had on the world, there’s no justification.

Do you think Google, TPG, and the other investors should have been more active as a counterbalance to the letter handed to Travis?

The perfect storm was that Google saw Travis, Uber, and the self-driving initiative as a threat. Look at what Google ultimately did to Anthony Levandowski.

Travis recruited Anthony and acquired his company, Otto, which was focused on self-driving semitrucks. Google went after him and tried to put him in jail. He was going to go to jail until Trump pardoned him during the first administration.

Google wasn’t in the mood to do anything favorable for Uber or Travis at the time. It was going to stay out of it.

I was disappointed and shocked that so many other investors were easily manipulated by Gurley and Benchmark and went along with the scheme. I don’t think anyone knew the extent to which Gurley had executed the strategy of hiring private investigators.

Was it an unfortunate coincidence that the tragedy of his mother’s death happened at the same time as the situation with Benchmark, or was it a deliberate coincidence?

I think they took advantage of an accident, for sure. But it was an architected strategy, starting in January 2017, to get rid of him.

I believe it was one of the worst venture decisions ever. Value destruction happened for everyone involved.

Venture is too secretive as an industry. That’s one of the things I believe. As more of this story comes out about exactly what happened at Uber—and more will come out as our investigation is completed—we’ll understand what happened.

10. Expenses on the Investigation

How much have you spent on this investigation?

I hired the top investigators in the world to figure this out. The fact that we found out that Fusion GPS was hired to fabricate a police report and go after me, and the fact that they went to that extent, is extraordinary.

You usually never find out about these firms because they hide behind multiple layers of law firms, so you can’t pierce the veil. The story of how we figured this out is incredible.

I feel very lucky. My dad, who is 86, made me promise to figure out what happened. People who know me know I was innocent and that it was fabricated. We had all the proof.

I’ve put it out there because it hurt my reputation at the time. I had to go through a pretty difficult experience. It was worth it to me to spend millions of dollars on legal fees and on the Section 1782 process.

We filed 6 Section 1782 cases. The latest one is against Fusion GPS. The judge found in our favor last year and is going to force Fusion GPS to say who hired them. They appealed it, and now we’re waiting for the judge to make the final judgment.

What do you expect it to say?

I can’t say publicly who I think hired Fusion GPS. That’s perhaps for a second episode, when we get that judgment.

Bad actors and bad behavior by VCs against founders are unjust. The industry is too secretive, and people are too afraid to talk about it.

I hope more comes out. In my case, there’s definitely more to come out. Once we find out who hired Fusion GPS, I think careers are going to fall.

Do you think there’s a lot more outside of this case?

Yes. There’s a history of VCs who have done this type of thing. In Benchmark’s case, they did it against Naval Ravikant. They hired private investigators against Naval and his company, eGroups, and he was thrown out of it. It was a very similar playbook.

That has happened multiple times at Benchmark, and it has happened at other funds. It needs to stop.

The political operatives who came into Silicon Valley after Uber and Facebook were attracted to it like flies. They started applying the same playbook.

You said something brilliant before this: that 2017 was almost a drunken period for venture capital.

The period from 2005 to 2015 was incredible. That’s when most of these great companies—SpaceX, Tesla, Facebook, Uber, and others—were founded.

There was a culture of meritocracy. Everyone was helping each other, and people were open-minded. You would meet at cafés. It was a beautiful era in Silicon Valley.

Then people realized, “My God, these people are going to become billionaires, and there are billions of dollars to be made.” You had the carpetbaggers, political operatives, consultants, and all these people coming in.

The other thing that happened—and I blame myself a little bit—is that bringing TPG into Uber in the Series C kicked off the whole wave of private equity coming downstream into venture, from Series C onward.

You saw what happened from 2017 to 2021 and 2022, during the drunken period. Mega-funds came in and spread billions of dollars at massive valuations that didn’t make rational sense.

WeWork is an example. $18 billion went into that company. I passed on it. Ironically, it was another Benchmark company.

I passed because I remembered the dot-com crash and all the office buildings being cleared out. I didn’t understand the business model. You don’t own the buildings, and you can be removed pretty quickly from your customers.

I didn’t see the strength in that business model, but companies with bad business models were getting billions in cash. That’s crazy. That’s not classic venture capital.

Doug Leone said on the show that we’ve gone from a high-margin boutique business and community to a low-margin, commoditized industry. He said there’s no way of putting that genie back in the bottle.

Venture capital as it is today, especially with private equity coming downstream and what we saw during the drunken era, is venture capital dead?

Venture capital is dead. The venture-capital model we grew up with and looked up to is gone.

The rate at which companies can be accelerated has grown to the point where you can execute on a business plan. In many cases, we’re seeing founders self-fund or generate enough success to build the company. More and more are opting out of venture capital.

Another trend, especially with crypto, is that decentralized-finance and alternative-financing mechanisms are evolving to the point where I think you can tokenize venture capital.

I think you can democratize venture capital and allow non-accredited investors to invest in the future. We have a moral obligation to open up venture and allow people to invest early in the Facebooks and SpaceXs of the future.

Mom-and-pop investors should be able to invest small checks. I think we’ll see changes in that direction during the Trump administration.

That model is going to change.

You’re an LP in many funds. We were chatting before this, and you said there’s just no cash coming back from the last vintage. How do you think about that? Have we seen the death of liquidity?

Liquidity has been a major problem, especially during the 4 years of Biden. It coincided with bad policies, a dearth of M&A, and a lack of IPOs.

I think that’s going to change in the next 4 years. I was an early person to come out and support Trump. I co-hosted David Sax’s fundraiser on June 6, publicly endorsed Trump, and most of my generation and cohort did the same.

People like Elon, David Marcus, Shan from Sequoia, and Emil Michael are all in Palm Beach doing 17-hour days. The best and brightest have converged there.

It’s very similar to Silicon Valley going to Washington. I’m excited because David Sacks is now the AI and crypto czar for the president. Elon is running DOGE.

You have some of the brightest minds in the world about to revolutionize how government works and make it much more efficient. I wrote a proposal about privatizing many aspects of government, including the US Postal Service, which is a big money loser and isn’t using modern technology to compete with FedEx, UPS, and DHL.

11. Quantum Computing & AI: The Next Frontier

We could do a lot better with Amtrak. Amtrak should be privatized and turned into Hyperloop and high-speed rail. We can do great things.

There should also be moonshots for AI. I do a lot in quantum computing and have done it for a long time. I believe AI and quantum are going to merge, and that’s going to accelerate the future.

I think the market is waking up, especially after Willow and what Google announced. This has been my thesis for more than 10 years.

There’s another company called [likely PsiQuantum] that came out of Cambridge here in the UK.

What do you think we should do with tariffs? I’m getting more and more intrigued by Chinese cars and Chinese car subsidies. I’m a massive believer in Adam Smith’s invisible hand, so I was always saying, “We should let them sell. This is ridiculous. They’re better cars.”

Then I saw how much they’re subsidized, and I thought, “This is an egregiously unfair playing field.”

They’re essentially state-owned enterprises. The Chinese government subsidizes them, and that’s a major threat to our ability to be competitive.

Even with tariffs, Chinese electric-car companies have gotten to the point where their cars cost around $115,000 and are good cars. Even if you add a 100% tariff, you’re still talking about $30,000, which is affordable to many people.

They’ll still be able to compete because their prices are so low. That’s something we need to think through because America has to build its own manufacturing capabilities, especially in semiconductors.

You saw Masayoshi Son announce a $100 billion investment in AI in the American economy and in American companies. What did you make of that announcement with Masayoshi and Saudi Arabia?

One of the things he talked about was that he had done the calculations, and the numbers make a lot of sense to me. Essentially, you need to spend single-digit trillions, and then you’re going to get $9 trillion of annual value from it.

I saw this. He said you spend $1 trillion in capex, and that will result in $9 trillion in annual gains.

I thought, “My word, he’s very precise with his $9 trillion—not $8 trillion or $10 trillion.”

The scale of what’s happening has grown. Everything has become bigger and more consequential. I think the next 25 years will eclipse everything we’ve seen in our lifetimes.

We’re about to go through civilizational change in the next 20 years. A fund like yours and a fund like mine have very lucky timing.

Are we lucky, or are we too small?

People like you, Harry, me, and others who have great instincts about people, companies, and trends are always going to succeed. You’re going to get into that deal even if you lose it to a bigger VC, as I did in the Uber case.

Your resilience and grit matter. If you can build authentic relationships with the great founders of the next 20 years, you’ll be their partners in building these amazing trillion-dollar companies.

I do think we’re lucky. We went through a drunken period because the business models weren’t actually correct. Now you’re dealing with AI and quantum computing. You’re going to have essentially the mind of God in terms of computing power, as you saw with Willow.

I’ve said for a long time that the reason I’m doing quantum computing is that what I see coming down the pike will allow us to solve problems that would take billions of years to solve in hours or days.

What does that mean? I’m so naïve. Does that mean solving cancer? Does that mean solving climate change?

Yes. I think quantum and AI are going to merge, even at the chipset level, and that will revolutionize every aspect of our lives.

We’ll find cures for every known disease in the next 10 years. One thing I started saying before Brian Johnson was a dear friend was, “Don’t die. Don’t jump out of planes, don’t ski, and just don’t die in the next 20 years.”

We’re going to reach a point of longevity where you’ll be able to live a healthy life for 150-plus years.

Do you really think so?

Absolutely. The level of advancement we’re about to experience is like a Cambrian explosion of superintelligence.

You don’t buy the negativity around the plateauing of large language models, the limits of data availability, compute, and energy?

I know too much. I’ve seen some of these technologies that other people haven’t seen that are coming down the pike. I’ve seen technologies that are going to get us to 1 million qubits.

Google is at around 100 qubits, even with Willow. When you’re talking about 1 million qubits, that’s the mind of God. You’ll be able to solve problems that would take billions of years in hours or days.

We’ll be able to find cures for all diseases known to mankind. People will die from accidents and not disease.

12. Spicy Questions

I didn’t have to lose my mother. So many of our loved ones whom we lose to old age can live healthier, longer lives and stay with us.

I love Bryan. He’s amazing. What a dude.

I want to do a very special round where we ask questions submitted by friends. You can choose not to answer, of course, but it’s a game show. If you don’t want to answer, you have to donate to a charity of your choice. Does that sound good?

Yes.

How much money did you make from Uber?

A couple hundred million.

Savage. Who do you think in Silicon Valley is one of the worst CEOs but has had the best outcome?

Steve [likely Ballmer]. During the decade he was CEO of Microsoft, Microsoft was completely flat. He’s now richer than Bill Gates, so he ultimately won.

They did a great job hiring Satya Nadella because Satya has been one of the greatest CEOs, one of the greatest CEOs of our lifetimes.

I love that.

Let’s do a quick-fire round. I’ll give you a short statement, and you’ll give me your immediate thoughts. What have you changed your mind on in the last year?

Before my granddaughter, Aurora, was born, I didn’t fully understand what being a grandparent was. I have to tell you, it’s 10 times more powerful than having a child.

I’ve changed my mind in the sense that I actually think the whole point of life is to become a grandparent. It unlocks a level of love that you’ve never experienced in your life.

I’m totally obsessed with my granddaughter. I see her every day and moved across the street from her. She’s the light of my life, and I live for her.

She’s given me a massive boost in energy and drive to make the world a better place for her and her generation. I became a grandparent at 48, so I was a young grandpa. It’s the most important thing that’s ever happened to me.

What’s the single best fund investment you’ve made?

I would say Lowercase, Chris Sacca’s fund. I put a small check into it and got $4 million out. Around $25,000 turned into $4 million.

It was a legendary fund. I think it was around $10 million and returned something like $1.5 billion. It goes in the record books.

How did you get into SpaceX?

Elon and I were friends. Another friend of mine, Justin Fishner-Wolfson, was on the board of SGN. Sean Parker was the Founders Fund representative who led the deal, but Justin was the person who came to the board meetings.

We became close friends. When Yuri did the deal, I went to Justin’s house. I actually named 137 Ventures that night.

As we were talking about him starting a fund, I looked over and asked, “What is that number block on your table?” It said “137.” He said it was his grandfather’s number seat on the exchange. His grandfather bought it after coming to America from Russia.

He was a Russian Jew who came with nothing, created success, and bought that seat. I said, “That’s the name of your fund: 137.” He said, “You’re right.”

Justin had helped bring SpaceX to Founders Fund. He was a junior partner, associate, or principal, along with Alex Jacobson, who was a co-founder of 137 Ventures.

They advocated for the SpaceX investment. Then they did a series of secondaries when they started 137 Ventures, so they’ve done very well.

Justin had some shares available in 2014 at around a $6 billion valuation. We put money into it at that valuation.

I think SpaceX will be a $1 trillion company. It’s just getting started.

What do you think is your most outlandish belief?

SpaceX being a $1 trillion company is a bold statement. Saying there will be many more trillion-dollar companies is bold. Saying that, in 20 years, we won’t die is also bold.

I helped start the Network State movement in 2012, and I had lunch with Joe [likely Lonsdale]. I said, “What if we started new cities that had sovereignty, new city-states, and tokenized them? What if ownership became citizenship?”

We started hosting New City salons. Balaji [likely Srinivasan] came to one, and then he wrote Network States. That movement led to another one of my mantras: great founders should try to start new industries, not just companies.

They should start a completely new industry. Hyperloop was a new industry, and in this case, Network States and new cities are a new industry.

There are now hundreds of startups starting new nations. [Likely Praxis] is another one that I’m involved in. It’s one of the largest Network States, and they’re looking at 1 million acres of land in different places around the world. I’ve been helping them with that.

We’re going to see new nation-states and new countries started in our lifetimes. A lot of people will opt into those new nations.

That’s probably one of my more controversial beliefs, but the world map 200 years ago looked very different from today, and it’s going to look very different in another 200 years. Nations aren’t supposed to be permanent. They’re supposed to evolve.

What was your biggest missed opportunity?

I had the opportunity to invest in Snapchat in the seed round, and I had the opportunity to invest in Pinterest in the seed round.

Why didn’t you do either?

I brought Snapchat to Menlo. Evan and I hit it off, and I really believed in it. I was on it within the first 30 days because my kids were using it. They showed it to me, and I was chasing it.

Unfortunately, Menlo passed on the round and then passed on the next round as well. Pinterest was when I was angel investing, so that was entirely my fault.

I met Ben Silbermann through Jack Abraham. I had funded Jack when he was 22 in his company Milo. He introduced me to Ben and said, “You should take a look at this.”

At the time, I was talking about social commerce as the next big wave, so Pinterest fit perfectly. But I did the meeting as a call instead of meeting in person.

The one time I didn’t get on the plane, the presentation over the phone wasn’t the same as it would have been in person. I passed because the presentation just didn’t hit for me.

If I had met Ben, I would have sensed his brilliance. This was around 2010 or 2011.

If you could invest in only 1 fund, which fund would you invest in?

Honestly, the one I’m really excited about is 1789 Capital, which my friend Omid Malik started. Donald Trump Jr. just joined as a partner there.

I think they’re going to kill it. I think they’re going to do amazing things. Their thesis early on was to invest in companies that are pro-American and anti-woke, and that thesis has worked really well.

They’re in an amazing position to invest in incredible companies. I really believe in them.

What fund do you think is most overhyped?

Benchmark.

Do you ever speak to Gurley?

No. These were friends of mine. Matt Cohler was a dear friend. I was at his 30th birthday party and his 40th birthday party, right before all of this happened.

We’ve lost dear, meaningful friendships because of that battle. The Uber War is something that should be studied to learn what to do right and what to avoid.

If you had the Uber War again, is there anything you’d do differently?

The strategy of publicly and legally battling was the only effective strategy I saw at the time. What I wish I had done, or had the wisdom to know to do, was what Sam Altman and his allies did in getting the OpenAI employees to back Sam and say, “If he doesn’t come back, we’re going to leave.”

That was very powerful. If we had done that at Uber, it might have worked because Travis and Emil were beloved by the team.

They were smart enough to turn a few key people, like Ryan Graves, against Travis and begin collaborating.

Do you blame Ryan?

He was another dear friend. It’s tragic, almost Shakespearean, the friendships that were broken over this.

There was a lot of love there, but I don’t speak to him anymore, and I don’t think others do either. Travis hired him from a tweet when he was 28 years old and working at IBM, made him a billionaire, and was extremely loyal to him.

Unfortunately, Ryan went to the other side for whatever reason, and that was heartbreaking.

Final one: what trait are you slightly ashamed of but that has contributed a lot to your success?

I’m extremely loyal. That loyalty has served me well, but it has also caused me a lot of pain in my life.

In some ways, my successes have also come from being loyal. People know that I wouldn’t do anything like what happened to Travis to a founder.

The same thing that has caused a lot of pain because I fought for people and took the bullets and missiles is also the reason I’m here and the reason I have the reputation I have with great founders.

Shervin, I’ve so enjoyed doing this. Thank you so much for getting on the plane. As the motto always says, this has been fantastic. You’ve been a star.

Thank you. I hope you get on the plane and come to Miami and visit me and Emil sometime. This was fantastic. Thank you so much.