20VC: Flexport’s Ryan Petersen: Reflections on Leadership from 13 Years Leading Flexport, Why Velocity not Speed is Most Important in Company Building, How Money Creates Inefficiencies in Scaling, The Future of Trade with China & Why Remote Work is so Challenging

Posted on 13th November 2023 by Harry

Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry.

In Today’s Episode with Ryan Petersen We Discuss:

1. The Origins of a Generational Defining Leader:

  • What did Ryan want to be when he was growing up?
  • How did scooters and motorbikes in China lead to the idea for Flexport?
  • What does Ryan know now that he wishes he had known when he started Flexport?

2. Speed and Money: The Secrets To Execution:

  • Does Ryan believe speed is key to execution? What is the difference between speed and velocity?
  • What advice does Ryan have to founders who raise a lot of money? How should it impact hiring?
  • What are the most common ways founders become inefficient post-fundraising?
  • Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder?

3. The Art of Resource Allocation:

  • Are the best CEOs the best resource allocators?
  • What is the single best resource allocation Ryan has made? What did he learn?
  • What is the worst? What did he learn?
  • What have been Ryan’s biggest hiring mistakes? How did that change his approach?

4. The Wider World:

  • Is Ryan long or short on China? Why?
  • Will we see global trade become nationalized? Why?
  • Will we see interest rates raised further? What impact does that have on trade?
  • What has been the impact of war on trade and the shipping industry?

5. Ryan Petersen: The Father and Husband:

  • How has having kids changed how Ryan approaches leadership and management?
  • How does Ryan juggle 2 young kids and leading a 2,500 person company?
  • How does Ryan retain romance with his wife while also being a full-on CEO of a large co?
  • Does money make you happy? What does it help with? What does it not help with?

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