Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

Ryan Petersen is the founder and CEO of Flexport, a technology-driven global logistics company. He’s a leading voice in supply chain innovation and has been at the forefront of solving major trade and shipping challenges worldwide.

Notes:

“Arrogance is its own form of stupidity.”
The Tweetstorm That Saved Christmas:
Ryan shares the now-legendary story of how he rented a boat, brought tacos, and took another high-powered CEO with him to tour the Port of Long Beach during the supply chain crisis. His viral Twitter thread sparked immediate action, California Governor Gavin Newsom called within hours, and the policy changed shortly after. A masterclass in “doing the thing.”
Frontline Obsession & Gemba Walks:
Why Ryan frequently travels the world (visiting 19 countries last year) to meet employees and customers. He explains the power of Gemba walks, being physically present on the frontlines, and how it shapes his leadership.
How He Runs Flexport:
Ryan’s leadership playbook includes:
- Managing through writing. Every one of his 26 teams writes a six-page memo monthly, followed by deep conversations.
- Daily conversations with 30-40 employees to stay connected.
- Living Flexport’s values:
  Empower Clients, Play the Long Game, Act Like an Entrepreneur, Commit to the Vision, Ask Why 5 Times.
Leadership & Decision-Making:
He shares his “must-haves” for hiring leaders:
- Relentless Work Ethic
- Intellectual Curiosity
- Humility (“Even wise people are wrong 30% of the time.”)
- Reliability
- Charisma
Lessons from Mentors:
Ryan talks about advice from Paul Graham (Y Combinator) and Brian Chesky (Airbnb), including how gathering your top leaders in person sparks innovation and alignment.
Hard Decisions & Mistakes:
He candidly discusses Flexport’s CEO transition gone wrong, hiring Dave Clark from Amazon, and what he learned from that difficult chapter.
Personal Growth & Life Philosophy:
Ryan shares his approach to lifelong learning, inspired by Charlie Munger and René Girard. He emphasizes reading widely, asking questions, and choosing role models wisely.
- "We’re all imitative people. Choose your role models wisely."
“We’re making global trade as simple and reliable as flipping a light switch.”
“Even wise people are wrong 30% of the time. You must stay humble.”

645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity

The Learning Leader Show With Ryan Hawk