Founder Stories

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Ryan Petersen: Flexport, Founder Mode, and the Return of the Founder-CEO

Ryan Petersen founded Flexport in 2013. He stepped back in 2022. He returned in 2023 to steer the company through the freight downturn. Along the way, Paul Graham's Founder Mode essay used his story as the anchor.

Ryan Petersen

Flexport

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Bootstrapped to $1.8M ARR selling software to small law firms

Fast Trackvertical SaaS

6 min read·legal tech

Bootstrapped to $1.8M ARR selling software to small law firms

Small law firms were supposedly an impossible market. Three years and one painful pricing reset later, Casefile is profitable, growing, and unburdened by venture timelines.

Bree CallowayCasefile

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The real storiesbehind the build.

Ryan Petersen: Flexport, Founder Mode, and the Return of the Founder-CEO

Every story, unfiltered.

Bootstrapped to $1.8M ARR selling software to small law firms

Built something worth telling?

The real stories
behind the build.