Summary

Shervin Pishevar’s central claim: Benchmark-led removal of Travis Kalanick was “the greatest value destruction since firing Steve Jobs at Apple.” His investigation, he says, found Bill Gurley “hired some private investigators, had weekly meetings about how do we get rid of Travis” starting January 2017 — before the Susan Fowler post — then Benchmark timed the resignation push to the week Kalanick’s mother died in a boating accident. “They pounced, which is just unbecoming.” These are Pishevar’s allegations, litigated but one-sided; take the venue into account.
The counterfactual he wants priced: had Travis and Emil Michael stayed, “Uber would be a trillion-dollar company by now” — Kalanick was on top of the 2017 AI paper and self-driving — versus Dara’s $175bn “great stabilizer” outcome. Pishevar says Benchmark invested $10m at a $50m pre-money valuation; using a hypothetical 10% stake, it could have had “$100bn to give to their LPs.” Instead, it moved against Travis six years in, when Pishevar says “if you had just waited four more years” the outcome would have been dramatically larger.
The deal itself is a masterclass in access: after losing the Series B to Andreessen, Pishevar told Kalanick “if anything happens in diligence, just know I’m 100,000% behind you” — two weeks later came the Algeria phone call and “can you meet me in Dublin tomorrow.” On Dublin cobblestones Kalanick revealed the real vision — replace car ownership, not compete with taxis — “you’re turning every car into an iPhone.” The TAM was trillions. Pishevar says Menlo’s term sheet was $20m at $290m, later mentions another $65m through a secondary, and separately says $26.5m became around $6.7bn.
The live litigation catalyst: Pishevar has spent “millions” on six 1782 discovery actions and says a judge ruled last year to force Fusion GPS to reveal who hired them to fabricate the London police report used against him in 2017 (London Police emailed the reporter “this is not our report”; Fast Company ran it anyway). Judgment pending on appeal: “once we find out who hired Fusion GPS, I think careers are going to fall.”
“Venture capital is dead” — the 2005–2015 meritocratic era gave way to carpetbaggers, political operatives, and PE coming downstream (he blames himself for bringing TPG into Uber’s Series C), culminating in the 2017–21/22 “drunken period” of $18bn into WeWork, which he passed on. His fix: tokenize and democratize VC so non-accredited “mom and pops” can buy the future Facebooks and SpaceXes — and he expects the Trump administration to open that door.
The frontier bet: quantum and AI “are going to merge, even at the chipset level.” He claims to have seen technologies “that are going to get us to a million qubits” versus Google Willow’s ~100 — “that’s the mind of God” — solving billion-year problems in hours. Consequence: “we’ll find cures to every known disease known to mankind within the next 10 years”; his advice — “don’t die in the next 20 years” and live 150+.
Tradeable scraps from the quickfire: SpaceX (bought at ~$6bn in 2014 via 137 Ventures) “will be a $1 trillion company”; his one fund pick today is Omid Malik’s 1789; most overhyped fund: Benchmark; Chris Sacca’s Lowercase turned his $25k into $4m ("$10m fund returned like $1.5bn"). On Chinese EVs: state-subsidized $115k cars survive even a 100% tariff at $30k — “they’re still going to be able to compete.”

Deep dive

1. The Uber deal: lose gracefully, then get on the plane

Pishevar chased Kalanick for a year before Menlo — “the answer is always no until you ask” — bombarding him with references from Sheryl Sandberg, Drew (likely Houston), and others until Travis “met with me because he had no choice.” When Kalanick chose Andreessen Horowitz for the Series B, Pishevar reacted “as a founder first, not as an investor”: congratulations, but “if anything happens in diligence, just know I’m 100,000% behind you — so negotiate with strength.”
Two weeks later, in Algeria for an Obama entrepreneurship summit, an unknown number: “hey homie, you remember what you said?… can you meet me in Dublin tomorrow?” Hence the second mantra — “always get on the plane.” Walking Dublin’s cobblestones over a pint, Kalanick shared the vision he kept close to his chest: replace car ownership. “All my competitors were doing their models based on taxi companies… no, no, no — you’re turning every car into an iPhone.” The TAM was trillions.
Pishevar ran to his hotel and texted a term sheet at $290m; after an hour of silence he panicked and texted $300m — the only time he ever saw Kalanick not negotiate: “no, 290 is fine.” He says Menlo’s term sheet was $20m, later mentions another $65m through a secondary, and separately says $26.5m turned into around $6.7bn.

2. Betting everything at 33 cents — and inventing the plumbing to do it

Leaving Menlo after 18 months, Pishevar negotiated deal-by-deal carry instead of fund carry — “I had a lot of faith in the deals that I did” — and sold all his Facebook shares at $53–58 to buy Uber secondary at an effective 33 cents a share: “I bet it all… if Uber didn’t work out I would have been bankrupt.”
The structuring was novel: Waverly loans, unused for 30 years — a tax-free loan to a founder exchanged for shares later — which he used for his own secondary and then popularized. The largest in history: $83m for TPG to buy G Camp’s shares, on which “TPG made close to two billion.” He was also “the first one to push SPVs hard” — $200m of Uber SPVs on top of Sherpa’s funds ($153m fund one, ~$175m fund two).
Asked point-blank how much he made from Uber: “couple hundred million.”

3. Thousand-X founders: what Travis-grade intelligence looks like

His filter comes from a Maryland math-science magnet school seeded with kids who “would remind you of a young Elon or a young Travis.” The lesson: “it’s not even 10x… these are like thousand-X humans — it’s worth waiting for the thousand-X founders.”
The specimen story: at an Oscars party, Yuri Milner — who set Kalanick hard math problems as a hobby — posed one verbally. Kalanick paced (“he would think by walking”), came back in two or three minutes with an equation, got “almost,” walked off again, and returned two minutes later with the right answer, all in his head. Pishevar puts him with Elon: “rare, Nobel prize-winning founders — nobody can do what Travis is doing, no matter how great you are.”

4. The Lyft mistake: six months of lobbying cost 30% of the US market

Pushed on where Uber wasn’t fierce enough, Pishevar names one: “the one time I saw Travis hesitate.” Lyft launched peer-to-peer cars (the pink mustaches) while Uber was still working on UberX, and for six months Kalanick lobbied the San Francisco taxi commission that “these guys are illegal” instead of just launching — “the first and last time he ever made that mistake.”
Those six months gave Lyft “about 30% market share” in the US. Uber came close to acquiring Lyft — “they wanted too much ownership, so that luckily didn’t work out” — and Andreessen, having lost Uber, ended up in Lyft.

5. Emil Michael and the fundraising machine

Recruiting the number two: Emil wanted a president or COO title; Kalanick’s answer, relayed by Pishevar — “tell him he can be president of himself on the business card.” Emil took the Klout job instead, and Pishevar planted a seed: “this was an IQ test and you failed it.” Six months later, a chance meeting at adjacent bathroom stalls in a Hong Kong restaurant — mid-Asia-tour with David (likely Bonderman) and Coulter — “we closed him that night.”
As Chief Business Officer, Michael “architected the $5 billion raise” with a process Pishevar calls genius: line the investors up in the hallway so they see each other, set a Friday term-sheet deadline. The Series D went from an opening $10–11bn to $17bn a year after Google’s $3bn Series C (Kleiner put in ~$100m, a deal likely led by Mood Rowghani). Then SoftBank’s ultimate $12bn — conversations Travis and Emil themselves started before being removed.
The city-launch playbook was celebrity riders: Pishevar brought Scooter Braun, Troy Carter, Ari Emanuel, Sophia Bush and Olivia Munn in at 33 cents, and Edward Norton rode Rider One to the beach with his surfboard for the LA launch — “then we replicated that playbook all over the world,” Bollywood actors and cricketers in India.
On whether the billions were too much too soon: “no, it was what was required. This is atoms and bits — you need cars and people and labor, millions of them, and you need to subsidize it.” On China: the Baidu JV made Uber “really one of the first” American consumer internet products allowed to launch there — Sherpa put $50m into Uber China and another $50m into Didi at the merger.

6. The Uber War, part one: the trap and the letter

Pishevar’s account of the unraveling: the business “did not fray — we were actually full steam ahead.” The problem was “the wrong venture capitalists on the board — in my opinion, that was Bill Gurley at Benchmark,” pressuring incessantly for an IPO. When Travis stopped responding, “we found out in our investigation that he hired some private investigators, had weekly meetings about how do we get rid of Travis, starting in January of 2017” — a month before the Susan Fowler post.
When Fowler’s post hit (Pishevar and Kalanick were sharing a Malibu house — “the last innocent weekend in Silicon Valley”), Rachel Whetstone, one of two Google political operatives hired at Uber whom Gurley had advised Travis to hire her, immediately pushed hiring Attorney General Holder for an independent investigation. Pishevar’s reaction in the room: “it’s a trap… if someone has a nefarious strategy to get rid of you, you’re vulnerable — things can be manipulated.” It went over Travis’s head; he agreed.
Six months later, the week the report was due, Kalanick’s mother died in a boating accident. The report “didn’t find anything wrong that Travis or Pishevar did” — its recommendation was to hire a COO, which Travis was in Chicago recruiting for — when Matt Cohler and Peter Fenton surprised him at his hotel with a letter from five early investors (Benchmark, Lowercase, First Round, Menlo): resign or we release this to the press. “He was very vulnerable, and they pounced — it’s not the type of behavior any VC should do.”
The regret: Travis should have said release it. “I now look at how Sam Altman handled his coup… how he galvanized the employee base… Travis was beloved. If we had done that at Uber” — but Benchmark “turned a few key people like Ryan Graves against Travis,” the man Travis “hired from a tweet when he was 28 at IBM and made a billionaire.”

7. The Uber War, part two: Delaware, Fusion GPS, and a pending judgment

When Benchmark sued in Delaware to strip Kalanick’s three board seats, Pishevar hired John Quinn (“the fiercest litigator in the corporate world”), counter-sued, and won — the seats were protected and Travis appointed Ursula from Xerox and the former Merrill Lynch CEO. Pishevar was also publicly organizing a shareholder group (Ron Burkle, Adam Leber) and telling CNBC he’d buy Benchmark out of Uber entirely.
Two weeks after the Delaware win, his investigation found a founding partner of Fusion GPS — “the firm famously that did the fake Russian dossier” — at a DC cafe handing a Fast Company reporter a memory stick with a fabricated London police report about him. Via 1782 discovery actions he obtained “multiple emails from the London Police telling the reporter this is not our report — and he still reported it.” Amid MeToo, October–November 2017, five anonymous accusations followed; he stepped back rather than let the attacks continue.
The live thread: his sixth 1782, against Fusion GPS itself — a judge found for him last year and will force Fusion GPS to say who hired them; it’s on appeal awaiting final judgment. “I can’t say publicly who I think hired Fusion GPS… that’s maybe for a second episode. Once we find out, I think careers are going to fall.” And this isn’t isolated: Benchmark “hired private investigators against Naval” at eGroups, he claims — “very similar playbook… it just needs to stop. Venture is too secretive of an industry.”

8. The trillion-dollar counterfactual — and why there’s no liquidity defense

The core value-destruction math: removing Travis and Emil — “two of the greatest minds in Silicon Valley” — was “the greatest value destruction since firing Steve Jobs at Apple.” Kalanick “was on top of” the 2017 AI paper and self-driving; “Uber would be a trillion-dollar company by now” against Dara Khosrowshahi’s stabilized, profitable $175bn. “Imagine if Benchmark had kept their 10% — they would have had a hundred billion dollars to give to their LPs.”
Harry’s steelman — LPs pressuring for cash, no distributions in years — gets flatly rejected: “absolutely not.” Benchmark put $10m in at a $50m pre-money in March 2011 and moved against Travis six years later, well inside the normal 7–10-year liquidity window. “Give him four more years… in their greed to go after single-digit billions, they made a critical mistake.”
Google’s passivity gets a motive: by then Uber’s self-driving push was a threat — “look at what they ultimately did to Anthony Levandowski… he was going to go to jail until he got pardoned by Trump.” Other investors were simply “easily manipulated by Gurley,” though he grants they likely didn’t know about the private investigators. Asked if he speaks to Gurley: “no” — and his most overhyped fund is Benchmark, though “candidly, I have respect for him as an investor.”

9. “Venture capital is dead” — the drunken era and what replaces it

The periodization: 2005–2015 was an incredible period — meritocracy, cafes, everyone helping each other — that produced SpaceX, Tesla, Facebook, Uber. Then “the carpetbaggers, the political operatives, the consultants” arrived, and PE came downstream into venture — “I blame myself a little bit because bringing TPG into Uber in the Series C kicked off the whole wave.” The 2017–2021/22 “drunken period” put mega-fund billions into irrational valuations: “$18 billion went into WeWork” — which he passed on, remembering the dot-com office clear-outs — “companies with bad business models were getting $18 billion in cash. That’s crazy.”
The verdict: “the venture capital that we grew up with, that model is gone” — founders self-fund or opt out, and DeFi rails mean “you can actually tokenize venture capital… we have a moral obligation to open up venture” so non-accredited mom-and-pops can write small checks into the future Facebooks. He expects the Trump administration to move regulation that way.
As an LP he confirms the liquidity drought — no cash back from the last vintage — blaming Biden-era policy, a dearth of M&A and IPOs, and expects the next four years to reverse it. He co-hosted David Sax’s fundraiser on June 6 and publicly endorsed Trump. People like Elon, David Marcus, Shan from Sequoia, and Emil Michael are all in Palm Beach doing 17-hour days. Elon is running DOGE. His consolation to small funds like Harry’s and his own: “if you can build authentic relationships with the great founders of the next 20 years, you’ll be their partners… the next 25 years is going to eclipse everything we’ve seen.”

10. Quantum, immortality, and the quickfire tape

The frontier thesis: “AI and quantum are going to merge, even at the chipset level.” He claims non-public knowledge: “I know too much — I’ve seen technologies that are going to get us to a million qubits; Google’s at like 100 even with Willow… that’s the mind of God.” Problems taking billions of years fall in hours — so “we’ll find cures to every known disease known to mankind within the next 10 years,” people die from accidents not disease, and lifespans hit 150+. The standing advice to friends, pre-dating Brian Johnson: “don’t die in the next 20 years.” He therefore rejects LLM-plateau pessimism outright, and flags a Cambridge-origin quantum company (likely PsiQuantum) alongside Willow as why “the market’s waking up.”
The misses carry a lesson: Menlo passed on Snapchat twice after he brought it in, and he passed on Pinterest himself because “I did it as a call instead of an in-person meeting — the one time I didn’t get on the plane… if I had met Ben I would have gotten the sense of his brilliance, but over the phone he just didn’t present well.”
Quickfire specifics: best fund investment — Chris Sacca’s Lowercase, “$25,000 turned into $4 million… a $10 million fund returned like $1.5 billion.” SpaceX — bought secondary in 2014 at ~$6bn via 137 Ventures (which he named, after Justin Fishner-Wolfson’s grandfather’s exchange seat number) — “will be a $1 trillion company; it’s just getting started.” One fund today: Omid Malik’s 1789, where Donald Trump Jr. just joined. Worst CEO, best outcome: Steve (likely Ballmer) — Microsoft flat for a decade, yet “he’s now richer than Bill Gates, so he ultimately won.”
The changes of mind are personal: grandparenthood (at 48) is “10 times more powerful than having a kid — the whole point of life is to become a grandparent.” His most controversial belief: network states — he hosted the first New City salons with Joe (likely Lonsdale) in 2012 before Balaji (likely Srinivasan) wrote Network States, backs likely Praxis (“looking at a million acres”), and argues “nations are not supposed to be permanent.” And the trait he’s half-ashamed of: extreme loyalty — “I’ve taken the bullets and the missiles… it’s also the reason I’m here and I have the reputation I have with great founders.”

Vol.152 Macro Talk 73 | Year-End Special: “How the World Got Here” Determines “Where We’re Going”A Conversation with 姜Dora: “Super Individuals,” AI, and Liangzhu