Flexport’s Third Act: Winning in a Broken Global Trade System

Flexport was a breakout success—reimagining global trade with tech at its core. But when the freight market cooled and efficiency overtook service, things started to unravel. Founder Ryan Petersen stepped aside, handing the CEO role to former Amazon exec Dave Clark. Months later, he was back at the helm.In this episode, Ryan explains what went wrong, how he’s rebuilding Flexport—cutting $300M in costs, restoring customer focus—and why promoting from within beats chasing outside stars. He also weighs in on Trump’s proposed tariffs and what they could mean for the future of global trade.Chapters: 00:00 Trailer00:31 Introduction02:07 Meeting smart people, seeing the world03:40 Eroded margins09:52 Charismatic and overconfident15:32 Not an overnight decision20:08 The founder has returned23:10 Redoing the hiring26:38 No substitute for passion31:00 Working for and with my brother37:28 Working with forwarders42:14 Being a founder can be lonely47:49 Life’s work54:06 The right person for the job1:00:55 19 countries1:04:57 Blowing people up1:07:24 Work and being a good dad1:08:34 Not doing it for money and loving money1:17:52 Import and export tariffs1:22:57 De minimis1:25:54 Panama and the Suez Canal1:36:50 Going public1:42:24 Who Flexport is Hiring 1:42:42 What "grit" means to Ryan1:43:06 OutroMentioned in this episode: Founders Fund, Amazon, Toyota Motor Corporation, Slack, Brex, Pedro Franceschi, Henrique Dubugras, United States Customs and Border Protection, ImportGenius, Michael Kanko, Y Combinator, Paul Graham, Intel Corporation, Shopify, Geely Holding (Zhejiang Geely Holding Group Co., Ltd.), The Volvo Group, Intuit TurboTax, David Petersen, BuildZoom, TechCrunch, Google, Figma, Barack Obama, Donald Trump, Jimmy Carter, Panama Canal Authority, United States Navy, Coinbase, Uber, AirbnbLinks:Connect with RyanXLinkedInConnect with JoubinTwitterLinkedInEmail: [email protected] more about Kleiner Perkins