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

Shervin Pishevar is a serial entrepreneur and investor. Shervin is famed for leading Uber’s Series B at Menlo alongside leading Warby Parker’s Series A and investing in Tumblr, all in just 18 months at Menlo. Following Menlo, Shervin co-founded Sherpa Capital and today Shervin is averaging over 73x on his investments. As an angel investor, Shervin made over 100 investments in the likes of Dollar Shave Club, Postmates, Facebook and more. ---------------------------------------------- In Today’s Episode with Shervin Pishevar: (00:00) Intro (01:00) Mother’s Impact Getting Into Tech (03:29) The Uber Story and Joining Menlo: How It All Started (05:01) Meeting Travis Kalanick (14:14) Being Strategic Advisor at Uber (21:36) Recruiting Emil Michael (26:05) Uber China: The Challenges and Triumphs (30:01) $15 Billion Raise (34:06) The Beginning of the End: Betrayal by Benchmark (47:30) The SoftBank Investment & Leadership Changes (55:17) Expenses on the Investigation (58:19) The Future of Venture Capital (01:04:25) Quantum Computing & AI: The Next Frontier (01:10:27) Spicy Questions (01:11:48) Quick-Fire Round ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Shervin Pishevar on Twitter: https://twitter.com/shervin Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #shervinpishevar #uber #menlo #investor #venturecapital #startups #traviskalanick #benchmark

Shervin PishevarguestHarry Stebbingshost
Jan 12, 20251h 23mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Shervin Pishevar Reveals Inside Story Behind Travis Kalanick’s Ouster

  1. Shervin Pishevar recounts his immigrant upbringing, early tech career, and path into venture capital that led to backing Uber at its earliest hyper-growth stage.
  2. He details how he won the Uber deal, his deep partnership with Travis Kalanick and Emil Michael, Uber’s aggressive global expansion strategy, and the massive financial upside it created.
  3. The conversation then turns to Pishevar’s version of the internal power struggle at Uber: he alleges Benchmark’s Bill Gurley orchestrated a campaign, aided by political operatives and an independent investigation, that culminated in Kalanick’s removal during a period of personal tragedy.
  4. Broader themes include the ‘drunken’ era of venture capital, the role of political and PE money in distorting Silicon Valley, his belief Uber forfeited a trillion‑dollar future, and his bullish views on AI, quantum computing, new network states, and the future of venture.

IDEAS WORTH REMEMBERING

5 ideas

Winning iconic deals often depends on relentless relationship-building and being physically present.

Pishevar only secured the Uber investment after a year of persistent outreach, leveraging multiple high-powered referrals, and literally flying to Dublin on a day’s notice—leading to a term sheet that turned roughly $26.5 million into about $6.7 billion on today’s prices.

The biggest outcomes come from backing ‘1000x founders,’ not just good companies.

He frames Travis Kalanick, Elon Musk, and Brian Chesky as rare, near–Nobel caliber founders whose intelligence and intensity can create trillion‑dollar outcomes, arguing it’s worth waiting and concentrating capital on such people.

Board composition and investor alignment can determine a company’s destiny.

Pishevar argues Uber had “the wrong VC on the board,” claiming Bill Gurley’s push for an earlier IPO, hiring of investigators, and alleged campaign to remove Kalanick destroyed hundreds of billions in potential value and changed Uber’s trajectory.

Founders should be extremely cautious about ‘independent investigations’ in politicized environments.

He views Uber’s decision to hire former Attorney General Eric Holder to investigate culture issues after the Susan Fowler memo as a strategic error that made Kalanick vulnerable to opponents during a broader MeToo and media storm.

Loyalty to founders can both protect reputation and invite retaliation.

Pishevar describes fighting publicly and legally on Kalanick’s behalf, which he says triggered a fabricated smear campaign against him; he spent millions on investigations and 1782 actions to uncover Fusion GPS’s role and clear his name.

WORDS WORTH SAVING

5 quotes

“If Travis and Emil had stayed at Uber, Uber would be a trillion‑dollar company by now.”

Shervin Pishevar

“You’re turning every car into an iPhone. You’re creating a network machine on wheels.”

Shervin Pishevar, on Uber’s true vision

“We had the wrong venture capitalist on the board. Unfortunately, in my opinion, it was Bill Gurley at Benchmark.”

Shervin Pishevar

“The Uber wars is something that should be studied in order to learn lessons about what to do right and what to avoid.”

Shervin Pishevar

“I actually think the whole point of life is to become a grandparent.”

Shervin Pishevar

Shervin Pishevar’s immigrant background, early startups, and entry into venture capitalHow the Uber investment happened: winning the deal, valuation, and upsideTravis Kalanick and Emil Michael’s leadership, Uber’s culture, and global expansionThe internal conflict at Uber: Benchmark, Bill Gurley, Susan Fowler, and Kalanick’s ousterPishevar’s own legal battles, Fusion GPS, and alleged smear campaignCritique of modern venture capital, ‘drunken’ capital era, and private equity encroachmentFuture outlook: AI, quantum computing, network states, and the evolution of nations and venture

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