Ryan Petersen is the founder and CEO of Flexport, a global logistics technology platform that’s transforming how goods move around the world. He launched Flexport in 2013 with a mission to fix the broken freight forwarding industry: bringing transparency, efficiency, and speed to global trade. Under his leadership, Flexport has grown into one of the world’s most innovative supply chain companies, serving thousands of clients across industries with digital tools, logistics services, and expert insights. Ryan is widely recognized as a visionary in global trade and logistics. His bold thinking during supply chain crises, including chartering ships and planes to solve bottlenecks, has made headlines worldwide. In 2022, after stepping down as CEO and serving as Executive Chairman, Ryan returned to the CEO role to lead Flexport through its next phase of growth and innovation. He earned an MBA from Columbia Business School and a BA from UC Berkeley, where he studied Chinese and Business. Before starting Flexport, Ryan co-founded ImportGenius.com, a data platform for global trade. He’s known for his candid, practical leadership style and his deep passion for solving tough, systemic problems.

Watch our conversation on YouTube. And SUBSCRIBE!

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.

Order Our USA TODAY Best-Selling BOOK, The Score That Matters. “People spend far too much time obsessing about external scoreboards and not nearly enough time thinking about their internal one. Hawk and Cupps offer an important corrective, arguing the most important measure is whether or not you are living in alignment with your core values.” — Brad Stulberg, Best-Selling Author of Master of Change

Be part of “Mindful Monday” — Text Hawk to 66866

The Learning Leader Show

  • “Arrogance is its own form of stupidity.”
  • “Rule number one in a crisis is everybody will rally around the calmest person in the room.”
  • “The best networking tool is being insanely good at whatever the thing is that you do.”
  • “You don’t become that type of a guy who does those things without being obsessed, without being a maniac, without working really hard.”
  • 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.”
  • Values must have intentional tension: Create values that can conflict with each other to force better decision-making. “Empower your client” vs “play the long game” creates healthy friction. “There’s an intentional tension… empowering your client and playing the long game may be at odds.”
  • Written documentation scales leadership: Use structured monthly reviews with six-page documents to manage teams globally. Written culture enables better decision-making across time zones. “We’re a very document-driven culture… It’s really hard to get everybody in a meeting at once. So we do a lot of written documents.”
  • Simplify complex problems: If you can’t explain something simply to a layman, you probably don’t understand it well enough. Avoid “chauffeur knowledge” – surface-level expertise without deep understanding. “If you can’t simplify a problem to a point where a smart layman can understand it, then you’re probably operating with too much chauffeur knowledge.”
  • Hire for work ethic above all: The hardest-working person often outperforms the most talented. You can’t assess this in interviews – you need reference checks from people who’ve worked with them. “Work ethic, very underrated… You won’t find that in an interview. You gotta talk to people who worked with them.”
  • 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.”
  • Choose role models consciously: Humans naturally imitate others. Be intentional about who you model yourself after, since you’ll inevitably copy someone’s behavior patterns. “You’re gonna imitate somebody. So you should be very conscious about who you imitate. 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.”
  • Apply to be part of my Learning Leader Circle
Resources:

More Learning:

Episode 078: Kat Cole – From Hooters Waitress To President of Cinnabon

Episode 216: Jim Collins — How To Go From Good To Great

Episode #300: AJ & Keith Hawk – How To Instill Work Ethic & Curiosity In Your Children

Episode #303: General Stanley McChrystal – The New Definition Of Leadership

Time Stamps:

00:51 – The Tweetstorm That Saved Christmas

01:32 – Investigating the Port Crisis

03:24 – Uncovering the Root Causes

05:34 – The Immediate Impact of the Viral Tweetstorm

06:32 – Leadership Philosophy & a Bias for Action

08:52 – The Daily Life of Ryan Petersen

17:12 – The Importance of Writing and Communication

20:42 – Core Values & Company Culture

33:31 – Leadership Transitions at Flexport

36:44 – Operational Rigor and Lean Principles

38:44 – The Value of Poise in Leadership

41:54 – Building Accountability Through a CEO Group

43:48 – Simplifying Global Commerce

50:28 – Balancing Work and Family Life

53:47 – Advice for Aspiring Leaders

57:35 – The Power of Networking and Learning