The Uber - Didi Chuxing Merger with Brad Stone, author of The Upstarts & The Everything Store

The episode frames the Uber–Didi deal through a market that was expanding faster than Uber’s early identity suggested. Uber had begun with black cars and limousines, while Lyft and Sidecar helped establish a broader model in which ordinary drivers could offer rides. Uber initially resisted that model: Travis Kalanick tried to shut the rivals down in California before adopting UberX after regulators did not intervene. The hosts use this reversal to distinguish Uber’s later scale from being the originator of ridesharing.

Brad Stone argues that Hailo’s public expansion plans had an unintended effect. They prompted Uber to accelerate its US expansion, but also alerted entrepreneurs in China to the opportunity. In the hosts’ account, roughly 30 companies entered the Chinese market between 2012 and 2013. One was Didi Dache, founded by Cheng Wei, then a 29-year-old Alibaba salesperson, with his former Alibaba colleague and mentor Wang Gang. Their initial Momo app was redirected toward taxi-hailing after they recognized the opportunity in GPS-enabled services. The pivot did not give them a clear field: Stone says dozens of companies had the same idea, with perhaps hundreds of teams forming in Beijing around the opportunity.

The account presents Cheng’s path as a series of setbacks rather than a preordained founder story: he left an exam page blank, failed at insurance sales, and discovered that a supposed healthcare job was at a foot-massage chain. Stone describes a combination of idealism and relentlessness: Cheng believed technology could make Chinese transportation more efficient, while Didi launched in cities even when ride-hailing was legally uncertain and continued after some launches were shut down. The transcript also cautions against treating him as a Chinese version of Bezos. Stone says Bezos’s early conviction about the internet and Amazon’s long period of being dismissed as a retailer were distinct; Didi’s early advantage depended in part on capable colleagues and a timely connection to Tencent.