• Startup Archive
  • Posts
  • Ryan Petersen on what Paul Graham told him when he stepped down as Flexport CEO

Ryan Petersen on what Paul Graham told him when he stepped down as Flexport CEO

May 02, 2025

Y Combinator founder Paul Graham was Flexport’s first investor. Ryan Petersen recalls telling Paul that he was hiring Amazon’s Dave Clark to replace him as CEO in 2022:

“No one has ever been more disappointed in me than when I told PG that I was hiring a CEO,” Ryan remembers.

Paul first asked Ryan if Flexport was his life’s work, to which he answered “Yes.”

“Then why would you ever leave?” Paul asked.

Ryan said he thought the new CEO would be better for the company.

“That’s like saying some other guy is going to be a better husband for your wife!” PG exclaimed. “It might be true, but you don’t act on it!”

Then PG offered Ryan the following advice:

“If this is your life’s work, and you think he’s better than you. You need to go learn all of the things that he’s better than you at so that you can come back and do the job.”

And that’s exactly what Ryan did. After a year, he returned as CEO of Flexport.