Filevine co-founder Jim Blake tried to quit 20 to 30 times
Ryan Anderson · He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine · PMF Show · Mar 9, 2026 · at 10:29
Ryan Anderson, founder and CEO of Filevine, reflects on early startup turbulence and having to repeatedly persuade his late co-founder Jim Blake to stay with the company over its first three years.
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“I got to be honest though, Pablo, Jim, who became like one of my lifelong friends. I mean, there may be no more important relationships to me outside of family than that of Jim Blake. But the man probably quit, or I used to say tried to quit, I don't know, 20, 30 times over the course of the next three years. Every, every few weeks he'd be like, look, we got this feature out, but you need to know that's the last, I'm not doing this anymore. And I would reel him back in so many times.”
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