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

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?