I have done everything myself so far, following the recommendations of this sub. It's been great just basically being a boglehead with my IRAs and 401k. I'm very thankful that my investments just tracking low expense ratio index funds have done exactly what they are supposed to do. And I file my taxes myself.
However, I am #blessed to have an 8 figure position in SpaceX that is by far the majority of my net worth.
I want to diversify. The standard way to do this is just to sell and then buy something else, but the tax hit of that would be astronomical. Apparently there are strategies to deal with this like a cashless collar, charitable remainder trust, exchange fund, and direct indexing with tax loss harvesting and probably some other stuff too. Additionally it feels like I need a tax planning person not just a CPA. And if you look at long angle I also need to do a bunch of other stuff that means hiring more people. https://www.longangle.com/research/sudden-wealth-checklist
I talked with a local RIA fee only fiduciary and he seemed quite simple and not really providing a ton of value over what I've already learned myself and wouldn't be able to facilitate any of the "fancy" stuff. I've talked to Goldman Sacs, JP Morgan, Fidelity, and Morgan Stanley and they all seem to be good at this but they charge a %AUM which is a lot. And it's not clear they cover the estate, tax, or insurance things either. They "assemble a team" which just sounds like more money out of my pocket.
Should I hire someone or just keep doing stuff the simple way myself and take a huge tax hit?