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I’ve seen a few threads like this here on HN. I feel like the most important thing is talk to a professional advisor. Take money off the tank but it’s not a “keep it all in the company” vs “sell”. You might want to do a rebalancing and keep 50/50 or something.

How much of your ownership stake would you need to sell to never worry about working again?

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I could 15-20% and not worry about working. My intention is to understand the optimal strategy. Keep the winner or sell shares and schedule and invest in ~50-60 new companies with larger tickets. I love my work and want to keep working.

If I could lock up a guaranteed "this will see me out the rest of my life" amount safely by selling 20% of a holding, I would do that then do whatever I wanted/have fun with the rest. If that fun involved angel investing in a handful of other companies, so be it. Take care of yourself, then do what feels good, I say!

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