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.”

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.

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.

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.

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.

He seemed to love his work. I would.

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.