I have $650k in equities and crypto. I want to diversify and buy a rental property (not ready to buy a home to live in yet), but I’m scared of the huge capital gains hit (I’ve made 1000%+ in some of my largest positions) if I sell some of my equities for the down payment. Are there any tax loopholes I’m unaware of to avoid paying capital gains before making the down payment?

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You could use securities based lending if your brokerage offers it, if the interest rate is low enough probably could make sense


This may not totally align with your goals but here’s my two cents. Start a charity and then donate the equities to the charity (not liquidated), the charity can then do whatever it pleases with the assets including sell with a tax shelter… the charity could then buy a property. If you wanted to create generational wealth this would work well, if you’re looking for an income property that you can rent for profit maybe not? At least this is what I understand from my tax lawyer. Please correct if others know more about it.


But then you’re paying tax on the salary instead of just paying cap gains one time and you’d lose the potential for a personal home cap gain exemption later (assuming you move in for 2 years prior to selling)

Hold for over a year so that the capital gains (federal) are 15%

Have held for over a year! And yeah, I live in CA :/

I read that you can do a wash sale on crypto and get the tax benefits from it

Good idea! But that only works if you’ve actually lost money from your crypto investments

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