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