Split across ~ $12m in pre-tax retirement accounts and ~ $9m in taxable brokerage

Classic example of concentrated bets creating wealth and now looking to diversify to keep it.

Biggest needle movers we talked about involved using the assets in the brokerage account to compound tax efficiently and pass some deductions along the way.

• Multi million dollar capital gain event coming up in the next 1-2 years. Tax-loss harvesting can reduce the tax bill on this.

• Multi million RSU package. Tax-aware hedge funds can help diversify the portfolio and potentially provide some relief on income taxes, which is huge when you’re in CA and taxed at the 50% marginal all-in rate.

• Current income being generated from the portfolio is being taxed at both Fed + CA levels, a simple switch to private real estate allows us to earn income that defers both Fed and CA income taxes.

• Talked high-level about the goal of getting this large IRA balance over to Roth IRA over the next 15 years after he retires and before RMDs start.

• Talked about crafting a gifting plan for kids as their net worth already exceeds the estate exemption, also talked about how a private placement life insurance policy could create a place to invest tax-free and compound growth outside of the estate.

This guy loves investing and has been an avid viewer of my YouTube channel.

He’s implemented some of the things I talk about on his own, but came to the realization that his spouse is not going to be able to take over the complicated portfolio he’s running and would rather have the peace of mind knowing that if anything ever happened to him, they would be taken care of.