What Happened to Lee

The question that occurs to me is: if you knew that was in your future, would you spend your last 10 good years toiling at a startup?

10 good years is a long time. As a founder I would guess he truly believed in the mission, at least before FTD took hold, and I think that kind of pursuit would be more fulfilling than a 10 year vacation.

Yes. His family are financially secure, thanks to his Cloudflare millions. I could die much more easily knowing my family were safe after I'd gone.

Yes. It would probably make me do so harder because it’s my life’s work and I have only that much time to do it.

That's the answer to "Would you spend your last 10 years securing a guaranteed multi-million dollar payout?" not "Would you work your tail off for a gamble?"

Startup != assured success.

I should have been more specific with my hypothetical. I only meant having knowledge of the disease, not of any kind of startup mega-success.

He seemed to love his work. I would.

In Lee's case, at least when he started his career; the answer to that is definitely "yes". He didn't "toil", and he was working on something he believed in and was passionate about.

While Lee's personality changed a lot over time, he was always the guy who got more out of hanging out in a garage building something than someone touring France/Italy/etc.

I don’t think Lee ever toiled. He was a “maker” in the best sense of the word. And, to this day, when he expresses himself in the limited ways he still does, he searches Google or YouTube for “Cloudflare.”