Ryan Petersen is the founder and CEO of Flexport, the platform that coordinates global logistics from factory floor to customer door.

In this conversation, he’s refreshingly transparent about the mistakes and painful lessons he’s learned building several companies.  He opens up about stepping down as CEO, his struggles with self-confidence, and what happened when he was forced to step in and save his own company.Along the way, we explore why micromanagement might be the secret to better leadership, how Trump-era tariffs reveal the hidden complexity of global trade, and what it takes to scale a company without losing control.

There are stories and lessons here you won’t find anywhere else, from a data leak that triggered a call from Steve Jobs to flying 500 million masks into the U.S. during a global shutdown. 
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Approximate Timestamps:
(2:49) Early Life  
(4:58) First “Start Up”  
(5:38) Living Abroad in China  
(10:19) Y Combinator  
(11:13) Steve Jobs & the iPhone 3G Launch  
(13:41) Lessons from Import Genius  
(22:33) Lessons from Paul Graham, Billionaire Investor  
(25:31) Flexport Early Days  
(36:08) COVID-Era Flexport  
(40:06) COVID-Era Flexport – Continued  
(44:09) Hiring Flexport’s First COO  
(47:02) Stepping Down as CEO of Flexport  
(51:07) Cutting Cost & Improving Quality  
(53:57) Lessons from Other CEOs  
(57:05) How to Hire the Best Employees  
(59:31) Paul Graham’s Closed-Door Talk  
(1:03:21) The Value of a 6-Page Monthly Business Review  
(1:06:57) Why Do Tariffs Matter? 
 (1:09:52) Tricks for Dealing with Tariffs  
(1:15:43) Other Creative Strategies for Tariffs  
(1:21:30) Dealing with Operational Bottlenecks  
(1:27:41) Lessons from Charlie Munger 
(1:30:12) Lessons from Peter Kaufman  
(1:37:50) What Is Success for You?
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