Jan 13, 2025 · 1h 23m · news
Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
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In this comprehensive interview, tech investor Shervin Pishevar shares a dramatic, behind-the-scenes account of Travis Kalanick's rise and highly controversial ouster from Uber, his own high-stakes legal battles against corporate smear campaigns, and his visionary outlook on the future of venture capital, AI, and global technology.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 8.8% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 1.7 Guest disagreement 1.6 Harry pushing back 2.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 50:55 Shervin forcefully rejects Benchmark justification
When Harry attempts to frame Benchmark's actions as a reasonable demand for LP liquidity, Shervin forcefully shuts down the premise with an emphatic 'No. Absolutely not.'
Hardest push from Harry ▶ 50:55 Harry pushes back on the anti-Benchmark narrativeHarry explicitly plays devil's advocate for Benchmark, asking if returning capital to LPs after six years provided a legitimate justification for their pressure on Travis.
Biggest teaching moment ▶ 27:29 Shervin explains Waverly Loans and venture structuresShervin details advanced VC deal mechanics, educating Harry on how Waverly Loans allow tax-free capital transfers to founders while retiring preferred shares.
Harry holds his own ▶ 1:04:53 Harry offers economic analysis on Chinese EV tariffsHarry moves beyond basic interviewing by articulating a clear economic thesis on how Chinese government subsidies distort free-market dynamics for EVs.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Shervin's Mother and the American Dream | 1 | 0 | 0 | 0 | Harry asks a supportive, personal opening question about Shervin's late mother. Shervin shares an emotional story about escaping Iran and his mother working multiple jobs to afford his first computer. | |
| Shervin's Path to Menlo Ventures | 1 | 1 | 0 | 0 | Harry lets Shervin guide the narrative on his path into venture capital. Shervin describes his early startups, mentorship from Sheryl Sandberg, and joining Menlo Ventures. | |
| The Legendary Dublin Deal: Securing Uber Series B | 1 | 2 | 0 | 0 | Shervin recounts winning the Uber Series B deal in Dublin by recognizing that replacing car ownership expanded the TAM into trillions. Harry acts primarily as a supportive listener. | |
| Structuring the Bet: Deal-by-Deal Carry and Personal Risk | 2 | 1 | 0 | 1 | Harry asks focused clarifying questions regarding deal structures and valuation prices. Shervin explains negotiating deal-by-deal carry at Menlo and putting his personal savings into Uber secondary shares. | |
| Cultivating Fierceness and the Lyft Competitive Oversight | 3 | 2 | 3 | 5 | Harry directly challenges the narrative by noting Uber's culture was seen as ruthless and hard-driving. Shervin explicitly rejects the premise, defending the culture while admitting they should have been fiercer competing against Lyft. | |
| Recruiting Emil Michael and Launching Uber China | 2 | 1 | 0 | 1 | Harry prompts Shervin step-by-step on key hires and expansion. Shervin details recruiting Emil Michael and the origin of Uber China through David Bonderman's network. | |
| Innovating Venture Structure: SPVs and Waverly Loans | 2 | 3 | 0 | 1 | Shervin educates Harry on financial innovations in VC, explaining SPV usage and structuring Waverly Loans to purchase founder secondary shares without dilution. | |
| The Corporate Coup: Bill Gurley, Eric Holder's Investigation, and Travis's Ouster | 3 | 2 | 3 | 3 | Harry asks for context on Susan Fowler's post and the board dynamics. Shervin delivers a scathing critique of Bill Gurley and Benchmark, alleging private investigators were hired before forcing Travis out during a personal tragedy. | |
| The Ousting of Travis Kalanick and the Uber War | 3 | 2 | 2 | 4 | Harry presses Shervin on whether Travis could have called Benchmark's bluff rather than resigning. Shervin explains Travis's vulnerability and details countersuing Benchmark in Delaware court. | |
| Fighting Back with UK Discovery Law & Life Tailspin | 3 | 2 | 3 | 3 | Harry asks probing questions about why a secondary buyout wasn't arranged. Shervin describes using Section 1782 discovery laws to trace smear campaigns to Fusion GPS. | |
| Uber's Potential as a Trillion-Dollar Company & Dara's Role | 2 | 2 | 2 | 1 | Shervin argues that removing Travis stripped Uber of its AI and automation leadership, asserting it would be a trillion-dollar company today under his leadership. | |
| Debating the Justification for Benchmark's Actions | 4 | 3 | 5 | 7 | Harry strongly challenges Shervin by playing devil's advocate for Benchmark's need to deliver liquidity to LPs after six years. Shervin flatly rejects the justification as absurd. | |
| Shervin's Multi-Million Dollar Investigation and Fusion GPS Lawsuit | 3 | 2 | 3 | 3 | Harry asks about the ongoing legal costs and broader implications. Shervin details spending millions on lawsuits against Fusion GPS and claims Benchmark used similar tactics against Naval Ravikant. | |
| The Drunken Era of Venture Capital and the Death of the Classic Model | 5 | 2 | 2 | 3 | Harry cites Doug Leone's take on VC shifting from a high-margin boutique model to a commoditized industry. Shervin agrees, describing the 'drunken era' of overcapitalization. | |
| The Death of Liquidity, Political Endorsements, and Government Privatization | 3 | 1 | 1 | 2 | Harry asks about LP liquidity shortages. Shervin attributes political shifts in Silicon Valley to policy failures and outlines ideas for privatizing government infrastructure. | |
| Tariffs, Chinese Subsidies, and Masa Son's Trillion-Dollar AI Thesis | 6 | 1 | 1 | 3 | Harry demonstrates strong macro awareness, re-evaluating his free-market beliefs regarding heavily subsidized Chinese EVs and lightly poking at Masa Son's $9T capex calculation. | |
| Super Intelligence, Longevity, and the Confluence of AI and Quantum | 4 | 2 | 2 | 4 | Harry questions Shervin on LLM plateauing concerns and compute bottlenecks. Shervin pushes back with extreme optimism about quantum computing and 150+ year human lifespans. | |
| Special Round: Uber Returns & the Worst CEO with Best Outcomes | 3 | 1 | 1 | 2 | Harry runs a rapid-fire question round. Shervin answers directly about his Uber payout ($200M+) and identifies Steve Ballmer as a CEO with weak execution but great financial outcomes. | |
| Getting into SpaceX and the Story of One Three Seven | 2 | 2 | 1 | 1 | Harry asks about early SpaceX access. Shervin shares how he named One Three Seven firm and outlines his vision for the network state movement. | |
| Shervin's Biggest Investment Misses: Snapchat and Pinterest | 4 | 2 | 4 | 3 | Harry probes Shervin's biggest investment misses and overhyped firms. Shervin reveals passing on Pinterest because he didn't fly in person, singles out Benchmark as overhyped, and laments lost friendships. |
Statements from this episode (49)
Pishevar: Uber would be worth $1T if Travis Kalanick stayed
“I believe if Travis and Emil had stayed at Uber, Uber would be a trillion-dollar company by now.”
Pishevar: Bill Gurley was the wrong VC on Uber's board
“We had the wrong venture capitalists on the board. Unfortunately, in my opinion, it was Bill Gurley at Benchmark.”
Pishevar: Bill Gurley hired PIs and met weekly to oust Travis Kalanick
“We found out in our investigation that he hired Some private investigators had weekly meetings about how do we get rid of Travis.”
Pishevar: Closed Uber, Warby Parker, Tumblr, and Machine Zone in 90 days
“In my first 90 days, I closed Uber, Warby Parker Tumblr, and Machine Zone.”
Pishevar: Menlo's $26.5M Uber investment grew to nearly $6.7B
“For twenty million at the time, later I got another six and a half million through secondary for Menlo. So that investment at today's prices is worth almost seven billion dollars.”
Pishevar: Deal-by-deal carry yielded higher returns than Menlo's fund carry
“I got more carry than I would have gotten in the fund by agreeing to do deal by deal carry.”
Pishevar sold all Facebook shares to bet everything on Uber secondary stock
“He allowed me to buy secondary shares from another early person, so I sold all my Facebook shares that had gone public at like, 53 bucks, 58 bucks a share, and I put it all I bet it all, everything I had, I put it all into Uber.”
Pishevar purchased secondary Uber stock at effective 33 cents per share
“It was 33 cents a share, effectively based on today's prices, so it would be 33 cents a share.”
Pishevar: Exceptional tech founders are 1,000x humans worth waiting to invest in
“These are people that are like, it's not even 10 X, you talk about 10 X engineers, these are like thousand X humans and so I've learned over time that it's worth waiting for the thousand X founders and investing in the future Travis's, or the future Elon's”
Pishevar passed on investing in Zimride before it became Lyft
“What happened was Lyft was, you know, Zimride, and I had passed on Zimride”
Pishevar: Kalanick's six-month regulatory delay cost Uber 30% market share to Lyft
“Travis Basically for six months was like, you know, telling the taxi commission, the city, government, like, you know, hey, these guys are illegal, like, well, you know, why are you allowing it, et cetera, instead of launching it, you know, as well which was l…”
Pishevar: Uber nearly acquired Lyft, but Lyft demanded too much ownership
“Andreessen, having lost the Uber deal, ended up doing the Lyft deal, and we had, you know, Travis and Emil, you know, they were close to acquiring it acquiring Lyft which, you know but they wanted too much ownership so that luckily didn't work out”
Pishevar: Emil Michael architected Uber's $15B fundraising efforts
“He architected the fifteen billion dollar raise he had a massive impact on the trajectory of Uber, and he became really Travis's right hand and sparring partner in building, building Uber.”
Pishevar's fund invested $50M in Uber China and $50M in Didi
“So I, ah, our fund, we put fifty million into the beginning of Uber China, and then later put another fifty million into Didi when they merged.”
Pishevar: Sherpa Capital raised $200M in SPVs for Uber
“So I ended up doing, we ended up doing two hundred million dollars of SPVs for Uber, on top of these other investments, and”
Pishevar: TPG bought $83M of Garrett Camp's Uber shares via Waverly Loan
“Solution was I introduced them to Waverly Loans, and we did the largest Waverly Loan in history, which was eighty-three million and bought Garrett Camp's shares for TPG for that amount.”
Pishevar: TPG generated nearly $2B return on $83M Uber investment
“I think TPG on that eighty-three million made close to two billion.”
Pishevar: Uber's Series D valuation was negotiated up to $17B from $10B
“So that Series D, like a year after the Series C, which Google and TPG did, that was at three billion. This was at seventeen billion, and we started off at 10. So, Emil was able to negotiate from, like, 10, eleven billion valuation to 17, because there was so …”
Pishevar: Holder's investigation report found no personal wrongdoing by Kalanick
“And the report, by the way, didn't find anything wrong that, you know, Travis did, or I did, or there was nothing, nothing in there about, you know, him, you know, directly and the recommendation was like to go hire a Sheryl Sandberg, like a chief operating of…”
Benchmark sued Travis Kalanick in Delaware court over Uber board seats
“About in early August They then sued in Delaware courts after they had already gotten rid of Travis. They then sued to get rid of him and his two board seats that he had gotten that he hadn't appointed yet. So three board seats. So they wanted, you know, effec…”
Delaware judge rejected Benchmark's effort to remove Uber board seats
“We make our arguments and the judge finds with us and rejects Benchmark's attempt to get rid of the three board seats.”
Pishevar: Fusion GPS gave a fake police report to Fast Company
“We found out an investigation that two weeks after I won the case founding Partner of Fusion GPS was sitting at a cafe in DC with a reporter from Fast Company with a memory stick and a fake police report from London about me. And they gave it to the reporter.”
Pishevar: London police emails explicitly disavowed fabricated report to journalists
“And there were multiple emails from the London police telling the reporter, like, this is not our report.”
Pishevar: Kalanick and Michael initiated SoftBank's $12B Uber deal
“So the SoftBank conversations, ironically, Travis and Emil started those conversations, the ultimate twelve billion dollar investment from SoftBank Vision Fund.”
Pishevar: Firing Kalanick from Uber was tech's worst mistake since Jobs
“And so they got two, two of the greatest minds in Silicon Valley were taken out of the company. This is the greatest value destruction that's happened since firing Steve Jobs at Apple. And it was a massive mistake.”
Pishevar: Kalanick and Musk are rare Nobel Prize-level founders
“Nobody can do what Elon's doing. Nobody can do what Travis is doing. No matter how great you are. These are, like, rare, rare Nobel Prize winning, essentially, founders.”
Benchmark invested $10M in Uber at $50M valuation in 2011
“Benchmark invested in March, 2011 at a, I believe it was a fifty million dollar pre-money valuation. They put ten million in.”
Pishevar: Benchmark ousting Travis Kalanick was one of worst VC decisions ever
“I believe that it was, you know, one of the worst venture, ah, decisions ever.”
Pishevar spent millions investigating Fusion GPS smear campaign
“It was worth it to me to, you know, spend millions of dollars on a, legal fees and doing the, we filed seven, four, the latest one is against Fusion GPS, and the judge found with us last year, and is gonna force Fusion GPS to say who hired them”
Pishevar: Uncovering who hired Fusion GPS will destroy careers
“Once we find out who've, who hired Fusion GPS, then, you know, I think careers are gonna fall.”
Pishevar: Benchmark Hired Private Investigators Against Naval Ravikant
“There's a history of VCs who have done this type of thing and in Benchmark's case, they did it against Naval. They hired private investigators and Naval Ravikant. He had a company called eGroups, and he got thrown out of it.”
Pishevar: Passed on WeWork over flawed business model
“I passed on that company, that was ironically another benchmark company. I passed on that company because it didn't, I remember the dot com crash and all the office buildings being cleared up. And I was like, I don't get this business model. You don't own, own…”
Pishevar: Traditional venture capital model is dead
“Venture capital as it is today, especially with private equity coming downstream and what we've seen with the drunken era venture capital is dead. The venture capital that we grew up with and that we looked up to is that model is gone.”
Pishevar: Trump administration will open VC to non-accredited investors
“So I think in the Trump administration, we'll see changes in that direction of like opening it up. And so that model I think is gonna change.”
Pishevar: Venture capital liquidity and IPOs will recover within four years
“Liquidity has been a major problem and especially during the four years of Biden and it just coincided with really bad policies and, you know, a derf of M&A lack of IPOs I think that's gonna change in the next four years.”
Pishevar: Chinese EV makers will stay competitive even with 100% tariffs
“Even with tariffs, these, the Chinese electric car companies have gotten to the point that, you know, their cars are like 15,000 dollars, and they're good cars. So even if you add a hundred percent tariff, You're still talking about 30,000 dollars, still affor…”
Pishevar: Masa Son's thesis of $9T annual value from AI capex makes sense
“Massa in Saudi, one of the things he talked about is he did his calculations, and the numbers for me make a lot of sense that basically you need to spend, you know, trillions, single digit trillions, and then you're gonna get nine trillion of annual value comi…”
Pishevar: Quantum and AI merger will cure all diseases within 10 years
“Quantum and AI, even at the chipset level, are going to merge. And then that's going to revolutionize all aspects of our lives. We'll find cures to every known disease known to mankind within, I would say, the next 10 years.”
Pishevar: Humans will achieve 150-plus year lifespan within 20 years
“Don't die in the next 20 years, because we're gonna reach a point of longevity where you'll be able to help, live a healthy life for 150 plus years.”
Pishevar: Steve Ballmer was a terrible CEO despite massive wealth
“Steve Ballmer. You know, the decade that he was CEO of Microsoft, Microsoft was completely just flat, right? And he's now richer than Bill Gates, right?”
Pishevar turned $25,000 into $4 million investing in Lowercase Capital
“I would say it would be lowercase Chris Saka's fund. I put, you know, a little check in there and got four million out like, 25,000 turned into four million, so it was a legendary fund. I think it was like ten million and returned like 1.5000000000 or somethin…”
Pishevar invested in SpaceX in 2014 at $6 billion valuation
“He had some available back in twenty-fourteen at like a, you know, six billion dollar valuation, so we put some money in at that valuation.”
Pishevar: SpaceX will become a $10 trillion company
“So I think SpaceX will be a 10 trillion dollar company. It's just getting started.”
Pishevar: Hundreds of startups are currently attempting to build new nations
“There's now hundreds of startups starting new nations.”
Pishevar: New nation states will be established and populated in our lifetimes
“We're gonna basically see new nation states, new countries be started in our lifetimes, and you're gonna see a lot of people opt in to those new, new nations.”
Pishevar: Menlo Ventures passed on Snapchat seed and Series A rounds
“I, so, I brought Snapchat to Menlo. Evan and I hit it off. I really believe that. I was on it in the first 30 days, because my kids were on it, and so they showed it to me, and I was chasing it, and Evan and I hit it off and unfortunately Menlo passed on the, …”
Pishevar: Uber allies should have staged OpenAI-style employee revolt for Kalanick
“What I wish I had done or had the wisdom to know to do was what, you know, Sam and his allies did in getting the employees at OpenAI to back Sam and say, if he doesn't come back, we're gonna leave. . It was very powerful, and if we had done that at Uber, becau…”