Previous company is going public but nowhere near my current company's valuation... If they go public and nothing literally happens to stock (just stays flat) then I get ~$1.5m pre-tax. I can sell all of my stock on first day but I won't because I have long term capital gains effective for 45% of my shares within the first couple weeks. About 10% becomes LTCG 4 months later. Another 45% becomes LTCG 2 months after that. I've thought of just selling as the shares become LTCG eligible - but what other strategies are there that would be effective? Should I just sell and immediately invest all in VFIAX? I don't plan on touching the money for a while because - well - literally nothing to do with it. I can't buy a house with it where I live (especially once I have to sell enough to cover taxes). I'm single and no kids but am trying to fix both of those things. What do people do that is most effective for this amount? It's not a lot in the scheme of things but enough that I'm thinking I should think a little bit more than just sell and diversify...? Is there a better strategy or some other advice? #ipo #taxes #advice #stocks
Would you actually be able to sell day one? Would there be a six month lockup?
Yes
How? Is it a direct listing?
I don't get this. How do you have ltcp on pre IPO rsus? I thought they were only issued during IPO and then you would get withholding and pay tax as income at that moment? Or are these stock options that you exercised a while back?
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Peter Thiel style Roth IRA
Wouldn't pass the IRS' eyes for a small man like me. Need to be a billionaire for the IRS to overlook that.
No need to be a billionaire to take advantage of ROTH IRA like Thiel. What you needed to do was exercise those options with the money in your ROTH IRA then at retirement you could have enjoyed the gains tax free. However if you got RSUs directly then there is no way to save on taxes, unless you transfer them to a trust and make the trust swindle it into shell corps (at just 1.5M it’s not worth the risk).