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Chaos in the global supply chain and big regulatory shifts set the stage as Ryan Petersen, founder and CEO of Flexport, explains how his team steered through COVID disruptions, rapid growth, and major pivots. Learn how Flexport tackled crises, restructured after setbacks, and built fintech products—plus candid founder lessons, B2B marketing hacks, and the realities of working with changing government policies.

00:00:00 - Supply chain chaos: What’s really happening?

00:01:35 - Flexport’s origin and YC journey with Paul Graham

00:04:05 - The 2007 legal change that made Flexport possible

00:06:16 - COVID hits: Hospitals, chaos, and pivoting to crisis aid

00:09:37 - Airlifting masks & Flexport.org’s massive response

00:11:07 - Post-pandemic: Scaling pains and CEO turnaround story

00:13:27 - Surviving and fixing operational meltdown

00:15:39 - Should startups focus or diversify? Lessons from Convoy

00:17:46 - Acquisitions, exits, and core customer clarity

00:21:06 - Why every company is a fintech: Flexport Capital’s story

00:24:32 - Lending innovations: Maritime law, risk, and collections

00:26:52 - Asset-backed lending, funding growth, and private credit

00:32:05 - Stablecoins, international payments, and FX tradeoffs

00:37:04 - Direct mail, toy planes, and B2B marketing ROI

00:41:06 - Brand, ROI, and investing in event-based relationships

00:42:19 - Policy shocks: De minimis, tariffs, and rapid pivots

00:46:20 - Lobbying government: How Flexport approaches DC

00:48:58 - Tariff consequences and “unintended” business impacts

00:51:39 - Tech memos, AI, and founder productivity hacks

00:53:03 - Ultimate founder advice: Burn rate, debt, and fundraising

00:54:56 - Halloween, Suez Canal, and life outside of logistics