The Upstarts Podcast Flexport’s Ryan Petersen: tech’s trade expert on solving tariff chaos with AI agents & winning again
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Mar 5, 2026 
Ryan Petersen, founder and CEO of Flexport, a logistics leader now pivoting to AI. He recounts engineering a company comeback and explains how AI agents tackle tariff chaos, automate auditing, and speed product development. Conversations cover restoring operational quality, inventive port reporting, and a bold plan to recover billions for U.S. importers.
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AI Plus Physical Execution Is The Advantage
- Flexport combines AI-driven decision making with real-world execution to optimize routing, loading, customs, and inventory moves.
- Ryan Petersen emphasizes feeding models the best data and then immediately translating algorithmic decisions into physical logistics actions.
Scooter Imports Sparked The Company
- Petersen began as an importer of motor scooters and hated the paperwork, which inspired founding tools to simplify imports.
- He and partners sold Gili scooters and later built Import Genius before launching Flexport as a "TurboTax for importing."
Build For Problems People Are Blind To
- Look for problems people are blind to — "schlepp blindness" — and build a product that removes the tedious work they ignore.
- Petersen cites Stripe and customs paperwork as opportunities born from ubiquitous, overlooked pain.