Uber CEO Dara Khosrowshahi

The interview opens with the scale of Uber's transformation since its 2019 IPO episode. Revenue had grown from about $10 billion two years earlier to more than $30 billion over the past 12 months, while the company narrowed its focus to mobility and Eats and exited hardware and speculative businesses. Profitability was still modest, but reaching break-even would have seemed unlikely when Uber burned roughly $3 billion in the year before going public. The hosts frame the conversation around both this operating reset and Dara Khosrowshahi's personal career history.

Before Uber, Khosrowshahi led Expedia for 13 years. One formative test came in 2001: IAC had signed a deal to acquire Expedia, but it had not closed when the September 11 attacks devastated travel. The agreement included a material-adverse-change clause, giving IAC an option to walk away. Expedia founder Rich Barton acknowledged that the business had fallen off a cliff and offered IAC a clear choice, while also saying he believed travel would recover.

Barry Diller decided to proceed without changing the deal. His line, 'If there isn't travel, there is in life,' expressed a long-term view of demand beyond the immediate shock. Khosrowshahi says the choice gave Expedia stability and looks brilliant in hindsight, while acknowledging that in the moment the uncertainty was difficult for employees and executives. He later saw a similar pattern during the pandemic: severe disruption can make the future feel unknowable, even when some behavior eventually returns to normal.

Khosrowshahi first met Diller as a junior analyst at Allen & Company during a hostile bid for Paramount. When his manager became ill, he had to present the deal's financial models directly to Diller. Diller wanted to speak with the person who had built the numbers rather than rely on an edited summary. Khosrowshahi describes this as a way to get unvarnished information before making a consequential decision, and says the experience made him want to work for Diller.