Wild. I vaguely remember this founder spending an obscene amount of money on some boutique firm to give homepage a small update. Seems he exited the Google grind about 6 years ago. I guess salaries were between $180-250K during that time frame. Google grinder for 6 years: $1,080,000-$1,500,000 Entrepreneur: “$920k over four years (with sale)”, but doesn’t include the 2 bombs he had prior to successful exit. (None of…
However, he kept trying again before job hunting or returning to big tech. This tells me the monetary factor was smaller than something else.
You mention the underrated educational experience in your last sentence, but there's so much more than that. He was probably never worried about his autonomy, being laid off, working with (or for) people he didn't want to work with, corporate politics, or anything else corporate bureaucracy introduces. This likely freed up his brain to be more creative and actually be used to 100% of its capacity.
I believe the obsession with TC in tech is highly problematic and there are a lot of talented folks optimizing for promotions via internal politics, rather than solving real problems for real people.
I also wish healthcare wasn't tied to employment, but that's a post for another time.