Infamous — "Backseat Confessions: The Story of Uber"

Hosts: Vanessa Grigoriadis, Natalie Robehmed
Guest: Mike Isaac (New York Times tech journalist, author of Super Pumped)
Date: September 4, 2025

Episode Overview

This episode of Infamous takes listeners on a deep dive into the explosive, controversial history of Uber, one of Silicon Valley’s most notorious disruptors. Through the lens of journalist Mike Isaac (author of the acclaimed book Super Pumped), hosts Vanessa Grigoriadis and Natalie Robehmed examine Uber’s origin tale, its ferocious culture under Travis Kalanick, the company’s impact on taxi medallion owners and labor, allegations of toxic behavior and sexual harassment, and the persistent issue of rider safety. The episode also explores the broader context of gig economy evolution and what the future of ride-sharing might look like.

Key Discussion Points & Insights

1. Personal Reflections on Uber’s Ubiquity (00:42–02:59)

• Vanessa shares initial hesitance and eventual reliance on Uber for convenience, highlighting how quickly public perception shifted from caution to normalization.
• Raises early questions about safety, driver verification, and the underbelly of gig labor.

2. Travis Kalanick: Uber’s Infamous Founder (03:44–08:41)

• Mike Isaac describes Kalanick’s background: smart, highly competitive, with a "chip on his shoulder" from childhood bullying.
• Notable traits: intense, persistent, hustler ethos—epitomized by stories like selling Cutco knives door-to-door.

  "He was a great door to door salesman... this spoke to the intensity of the guy from a real young age." — Mike Isaac (06:01)

• The myth-making around Uber’s origin story in Paris—Travis wasn’t the original founder; Garrett Camp sparked the idea, but brought Kalanick in to scale it.

3. Disrupting the Taxi Industry (10:49–16:36)

• Uber’s entry into NYC was a direct challenge to the entrenched taxi medallion system—hostility from taxi unions and political operators.
• Taxi medallion values plummeted; financial ruin for many cab drivers, some even facing bankruptcy or suicide due to lost investments.
• Uber portrayed as prime mover in the gig economy, often at workers’ expense.

  "At best, [former cabbies became] Uber drivers. At worst, some literally committed suicide because of financial (ruin)." — Mike Isaac (16:00)

4. The Gig Economy’s Double-Edged Sword (16:36–18:33)

• Unlike traditional employment, gig workers lack healthcare, retirement plans—Isaac: Uber didn’t invent the gig economy, but they "pioneered it at scale."
• Vanessa: Uber’s "move fast, break things" ethos left a trail of destabilized lives.

5. Uber’s Culture of Excess and Tactics of Aggression (18:33–21:35)

• Peak excess: Mega-funding rounds, parties with Beyoncé (paid in equity).
• "Operation Greyball": Uber secretly blocked government regulators from booking rides, evading law enforcement in cities where ride-hailing was banned.

  "They would basically pinpoint who these transportation officials were, give them a sort of fake, quote, unquote, gray ball version of the app, and make them unable to call cars..." — Mike Isaac (20:44)

6. Toxicity, Scandal, and Reckoning (21:35–24:56)

• Susan Fowler’s whistleblowing letter exposed sexual harassment, discrimination, and a broken HR department, sparking a domino of revelations and Travis Kalanick’s ouster.

  "Women on the teams were treated differently than their male peers... as Fowler spoke out, it became very clear that it was not just one person." — Mike Isaac (22:27)

• Travis’s off-color nickname “Boober” and tales of working/cozying up at notorious strip clubs like Gold Club cemented a caricature of the tech bro.

  "Travis would, I guess, take his laptop there and do coding and be like, less interested in what was going on there than working." — Mike Isaac (24:21)

7. Ongoing Safety Problems: Sexual Assaults in Ubers (26:07–32:51)

• The NYT exposé revealed a report of sexual assault or misconduct in Ubers in the US nearly every 8 minutes (2017–2022), far more than previously known (29:00).

  "Uber received a report of sexual assault or sexual misconduct... almost every eight minutes on average between 2017 and 2022..." — Natalie Robehmed citing Emily Steele, NYT (29:00)

• Natalie shares her own uncomfortable Uber Pool experience (28:03).
• Isaac asserts that while Uber enables post-fact tracking/reporting, "it doesn’t account for how this is something they’ve not been able to eliminate" (31:32).

8. Solutions: Gender Pairings, Technology, and the Future (31:42–34:10)

• Discussion about the potential for women riders to request female drivers—a feature Uber has considered, with mixed success among competitor startups.

  "This would be a popular enough function... this is something that women have to think about on any ride, much less in the middle of the night." — Mike Isaac (32:06)

• Self-driving cars as a potential solution to human safety risks—but then comes the next dilemma: job loss for drivers.

  "It’s this game of whack a mole that tech in general can create sometimes that can change the world for better and sometimes... in profound ways we didn’t expect." — Mike Isaac (33:10)

• Prediction: Self-driving taxis will arrive in more major cities within three to five years (34:18).

Notable Quotes & Memorable Moments

• The Value of Myth

  "They love to do myth making and think about how can we look backwards and make a founding story more romantic?" — Mike Isaac (07:07)

• On ‘Boober’ and Tech Bro Chauvinism

  "He talks about how Uber had kind of boosted his desirability with women, calling the company 'Boober.'" — Natalie Robehmed (24:01)

• On Labor Displacement and Personal Tragedy

  "Some [former taxi drivers] literally committed suicide because of financial [ruin]." — Mike Isaac (16:00)

• On Uber’s Tactics Against Regulators

  "They would basically... give [transportation officials] a fake app and make them unable to call cars so they can’t impound them or ticket them." — Mike Isaac (20:44)

• On the Challenge of Fixing Uber’s Safety Crisis

  "They can track these people... report them... But in the moment, this can be very scary." — Mike Isaac (30:24)

• On Automation Replacing Human Drivers

  "If we go into a self-driving future... oh, now you want to take away every job of someone who you are telling that they need to create their livelihood as a gig worker on Uber." — Mike Isaac (33:10)

Important Segment Timestamps

• Uber’s Early Days & Kalanick’s Rise: 03:44–08:41
• NYC Taxi Medallion Crisis: 10:49–16:36
• Uber, Lyft, and Gig Work: 16:36–18:33
• Uber's Opulent Culture: 18:33–21:35
• Operation Greyball Exposed: 20:44–21:35
• The Fall of Travis Kalanick: 21:35–24:56
• Strip Club Culture Anecdote: 24:21–24:56
• Sexual Assaults & Safety Concerns: 26:07–32:51
• Gender Pairing & Solutions: 31:42–32:51
• The Autonomous Future: 33:10–34:43

Closing Thoughts

The episode paints a richly detailed, unflinching portrait of Uber—from the idealistic veneer on its founding myth to the moral crises and systemic challenges it now faces. Uber is shown as both a pioneer and a cautionary tale of Silicon Valley’s breakneck disruption: a company that reshaped cities and labor, but also one whose “move fast and break things” attitude has left unresolved questions of exploitation, safety, and the human cost of progress. The conversation offers no neat answers, but gives listeners plenty to ponder about the future of work, technology, and urban life.

Recommended Reading:

• Super Pumped by Mike Isaac
• New York Times investigations into Uber’s corporate culture and rider safety issues