Feels like there should be the equivalent of Matt Levine's "Certificate of Dumb Investment" for this scenario. ~90% of startups fail. Your equity is statistically likely to be worth $0. You will likely grind for years with nothing to show for it except the experience, your network, and whatever cash comp you collected. Proceed accordingly.
(edit: totally fine to still jump into a startup role if you're not optimizing for quality of life and economics; I did because I enjoyed the work and the team)
Yeah, the only real regret is I could have got this experience more quickly with less pain and time not spent with my wife
Edit: just realised that made it sound like she died. She’s fine! We just had baby #2! But we could have spent lockdown making bread and playing RuneScape instead of me grinding
https://news.ycombinator.com/item?id=24285305
(edit: totally fine to still jump into a startup role if you're not optimizing for quality of life and economics; I did because I enjoyed the work and the team)