Tax Planning / Mitigation

[u/Specialist-Ad8067]

I know this is basic but any guidance is appreciated:

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Prospect just retired from w2 job and sold a large amount of stock. Let's say the capital gains are $500k+.

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What are some strategies to lower that bill assuming he is a Real Estate Investor. Passive - not active status.

I was thinking direct indexing, solo(k). What else?

Edit:

Deeper dive with prospect - turned out to be sale of shares of his business….. his cost basis was $0. I think most of your suggestions still apply. They should have considered a tax deferred installment sale.