As others have said, it largely comes down to personal preference, as you have enough to live comfortably either way. Keep in mind, there are 2 ways to "take your foot off the pedal": 1) Increase spending; 2) Set more conservative asset allocation. You can do either or both if you'd like, or you can simply continue doing what you're doing if you want to maximize your potential to be very wealthy. I'm a bit confused by your 2nd-to-last bullet point, but I think what you mean is that you don't foresee yourself spending more as you're already living quite comfortably at your current spending level. Personally, I would shift to a relatively conservative asset allocation to account for the risk/reward skewness toward your company, like you said. However, it's not like you "need" to do that, and you may very well feel that the likelihood of such large returns are sufficiently low that you want to risk up your portfolio to achieve your goals independently of company results.
I think the thing you really want to hone in on is this sentence:
Makaveli wrote: ↑Thu May 06, 2021 8:40 pm
Yet, I also feel like I am at an age where I can weather most storms.
The thing is, do you
want to? If you love working and don't see yourself retiring early or anything like that, and you have sufficient faith in your ability to keep a job, then it's fine to plan on working through any downturn. But if you instead place more value on the ability to just hang up your hat if this company doesn't work out and there's a crash in the next few years, then maybe it's time to focus on de-risking the portfolio a bit. I definitely fall into the latter camp, as the bulk of my life goals and aspirations have nothing to do with my day job and I would be as happy as a pig in a sty never having to work for someone else again. But that's just me. I got the impression you're much happier and confident in your work than I am, so that may not describe you at all.