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 Trailer
00:31 Introduction
02:07 Meeting smart people, seeing the world
03:40 Eroded margins
09:52 Charismatic and overconfident
15:32 Not an overnight decision
20:08 The founder has returned
23:10 Redoing the hiring
26:38 No substitute for passion
31:00 Working for and with my brother
37:28 Working with forwarders
42:14 Being a founder can be lonely
47:49 Life’s work
54:06 The right person for the job
1:00:55 19 countries
1:04:57 Blowing people up
1:07:24 Work and being a good dad
1:08:34 Not doing it for money and loving money
1:17:52 Import and export tariffs
1:22:57 De minimis
1:25:54 Panama and the Suez Canal
1:36:50 Going public
1:42:24 Who Flexport is Hiring
1:42:42 What "grit" means to Ryan
1:43:06 Outro

Mentioned 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, Airbnb

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Episode 292 Week of May 27th - June 2nd