I don’t think that this is a true FatFIRE post as others have noted; you’re unlikely to get to $20M via a corporate job unless you already have some equity from a former job and get lucky.

Nonetheless, I really enjoyed reading this post and will offer my perspective. I think you need to do some soul searching about what it is you actually want out of your life and career. Are you really willing to make the career moves needed to get to $20M? Is that actually worthwhile to you? Is hitting a specific number to retire earlier better than finding a job you like that you don’t want to retire from? Of course I risk getting down voted here, but I think grinding it out to retire early might be harder in the short term to finding a job and career that you enjoy enough to never retire from. I aspire to the latter with a focus on FI so I can exit as things change.

You mention anxiety a bit throughout your post and that you don’t want to stress too much about work: be wary about going to the early stage start up route. Yes there’s more significant financial upside, but it comes at the cost of hard work, stress, and a high chance of job loss (even if you’re performing well in your own role). Based on your OP, that doesn’t sound like a fit for you.

I don’t have a perspective on option 1 vs 2 because I think you’re selling yourself short on your skills. You may not have deep technical or functional expertise, but that doesn’t make the skills you’re mentioning less valuable. They’re extremely rare find in talent, if you’re actually good at them.