Ryan Petersen: Building the Hidden Engine of Global Trade
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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Ryan Peterson @typefast
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1:40:59
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1:40:59
Katharine Graham: The Woman Who Took Down a President [Outliers]
When Katharine Graham took over the Washington Post in 1963, she was a shy socialite who'd never run anything. By retirement, she'd taken down a president, ended the most violent strike in a generation, and built one of the best-performing companies in American history.
Graham had no training, no experience, not even confidence. Just a newspaper bleeding money and a government that expected her to fall in line.
When her editors brought her stolen classified documents, her lawyers begged her not to publish. They said it would destroy the company. She published them anyway. Nixon came after her, attacking her with the full force of the executive. Then Watergate. For nearly a year she was ridiculed and isolated while pursuing the story that would eventually bring down the president.
Graham proved that you can grow into a job that initially seems impossible and no amount of training can substitute for having the right values and the courage to act on them.
Approximate timestamps: Subject to variation due to dynamically inserted ads:
(02:19) The Making of an Unlikely Heiress
(10:15) The Education of a Publisher’s Wife
(22:16) Learning to Lead
(30:46) Becoming a Media Titan
(44:12) Legacy
(47:59) Reflections + Lessons
This episode is for informational purposes only and is full of practical lessons I learned reading her memoir, Personal History and watching Becoming Katharine Graham. Check out highlights from this book in our repository, and find key lessons from Graham here: https://fs.blog/knowledge-project-podcast/outliers-katharine-graham/
Thanks to ReMarkable for sponsoring this episode. Get your paper tablet at reMarkable.com today
Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: fs.blog/membership and get your own private feed.
Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
Follow me on X at: x.com/ShaneAParrish
Check out our website for all stock video and photo credits. Episode photo sourced from: iwmf.org/community/katharine-graham/
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57:36
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57:36
Daniel Kahneman: Algorithms Make Better Decisions Than You
Daniel Kahneman won the Nobel Prize for proving we're not as rational as we think. In this timeless conversation we discuss how to think clearly in a world full of noise, the invisible forces that cloud our judgement, and why more information doesn't equal better thinking. Kahneman also reveals the mental model he discovered at 22 that still guides elite teams today.
Approximate timestamps:
(00:36) – Episode Introduction
(05:37) – Daniel Kahneman on Childhood and Early Psychology
(12:44) – Influences and Career Path
(15:32) – Working with Amos Tversky
(17:20) – Happiness vs. Life Satisfaction
(21:04) – Changing Behavior: Myths and Realities
(24:38) – Psychological Forces Behind Behavior
(28:02) – Understanding Motivation and Situational Forces
(30:45) – Situational Awareness and Clear Thinking
(34:11) – Intuition, Judgment, and Algorithms
(39:33) – Improving Decision-Making with Structured Processes
(43:26) – Organizational Thinking and Dissent
(46:00) – Judgment Quality and Biases
(50:12) – Teaching Negotiation Through Understanding
(52:14) – Procedures That Elevate Group Thinking
(55:30) – Recording and Reviewing Decisions
(57:58) – The Concept of Noise in Decision-Making
(01:01:14) – Reducing Noise and Improving Accuracy
(01:04:09) – Replication Crisis and Changing Beliefs
(01:08:21) – Why Psychologists Overestimate Their Hypotheses
(01:12:20) – Closing Thoughts and Gratitude
Thanks to MINT MOBILE for sponsoring this episode: Get this new customer offer and your 3-month Unlimited wireless plan for just 15 bucks a month at MINTMOBILE.com/KNOWLEDGEPROJECT.
Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: fs.blog/membership and get your own private feed.
Watch on YouTube: @tkppodcast
Photograph: Richard Saker/The Guardian
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1:12:52
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1:12:52
Les Schwab: Why Real Ownership Outperforms Experience, Capital, and Credentials [Outliers]
They weren’t employees. They were partners. Les Schwab didn’t build a company. He built a culture.
This episode reveals how one small-town tire dealer scaled to $3 billion by turning customers into evangelists and employees into owners. Somewhere between changing his first flat tire and opening his 410th Les Schwab Tire Center, Les discovered something profound: his people weren't just working for him, they were working with him. They weren't building his dream, they were building their own. This episode is a case study on how strategy, incentives, and trust create massive advantages that resources can’t buy. When investment bankers offered Schwab billions to sell his empire, he refused after asking himself just one question: “What would I do with the money?”
Les Schwab understood something most never learn: the real wealth isn't in what you keep.
Approximate timestamps: Subject to variation due to dynamically inserted ads: (01:49) Roots (11:21) In Business (27:50) Building an Empire (40:18) Maturation and Legacy (48:21) Reflections from Les Schwab (51:22) Lessons from Les Schwab
This episode is for informational purposes only and is based on Pride in Performance: Keep It Going by Les Schwab
Thanks to Basecamp for sponsoring this episode: basecamp.com/knowledgeproject
Check out highlights from this book in our repository, and find key lessons from Schwab here: https://www.fs.blog/knowledge-project-podcast/outliers-les-schwab
Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: fs.blog/membership and get your own private feed.
Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
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58:42
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58:42
Harley Finkelstein: You Must Requalify for Your Role, Every Year
Shopify President Harley Finkelstein talks with Shane Parrish about treating every role in your life like a job you have to earn again each year.
Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI's real advantage, the calendar system that keeps him accountable, and how he maintains high standards.
Approximate timestamps:
(00:02:10) Living With Unreasonably High Standards
(00:03:40) Generational Trauma and Family Relationships
(00:07:52) Growing Up With Adverse Circumstances
(00:14:42) Prioritizing In Life And Becoming World Class
(00:24:45) Requalifying For Your Job
(00:30:05) Mindset for Professional Growth and Success
(00:31:33) How To Find A Great Business Partner
(00:32:57) Switching From COO Of Shopify To President/Chief Storyteller
(00:40:34) How Storytelling Impacts Shopify
(00:42:00) How To Get Better At Storytelling
(00:46:13) Shopify And How Commerce Has Evolved
(00:49:27) Forced Entrepreneurship Vs Passion-Based Entrepreneurship
(00:51:34) Mentorship
(00:59:41) Overcoming Failure And Rejection
(01:02:46) Out Caring Is More Important Than IQ, EQ, Raw Talent
(01:06:07) Parenting And Teaching A Hardwork Ethic
(01:11:23) Teaching Resilience
Thanks to our sponsor for supporting this episode:
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Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
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Watch on YouTube: @tkppodcast
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Acerca de The Knowledge Project with Shane Parrish
Master the best of what other people have already figured out. Each week, I learn from the best so you can apply their insights to your life. No fluff, no filler, just timeless conversations that make you smarter.
Inspired by Charlie Munger's timeless advice: "I believe in the discipline of mastering the best that other people have ever figured out. I don't believe in just sitting down and trying to come up with everything on your own. Nobody's that smart."
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