alt Hacker NewsI’d take the money, spend time with family (he mentioned toddler) and then figure out what to do next. Retiring isn’t everyone’s dream but at least having generational wealth is a big relief.
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you can take the money... and then continue to work. Nothing says you have to retire- I would have taken the money and figured out what's next! Not to mention that hopefully you've given shared ownership with your other early employees, who can also then at least have the opportunity for their own liquidity event.
Honestly, I respect the commitment. It's almost certainly a bad decision, but a founder that can turn down a 9 figure exit at the tail end of a tech bubble he's right in the middle of, has a good chance at having the right mindset to build a great company and survive the collapse. There's a good chance he regrets this for the rest of his life, but you can't argue that he wasn't a true believer or is a sellout.
The secondary provided that relief. Continuing to work on the company makes perfect sense if you enjoy it, which he clearly does (with the inescapable ups and downs of every start up of course).