Had a great call yesterday with someone with a $15M portfolio.

His 3 main pain points:

1. Concentrated stock from a previous employer
2. Large W‑2 income from RSUs with his current employer
3. Looking at buying a house in CA and it’s insanely expensive

Solution #1

We walked through using a tax‑aware long/short strategy to wind down the concentrated position in a largely tax‑neutral way.

There’s nuance here: do you just let it ride while you harvest losses, or hedge with a collar so you don’t get crushed if it sells off?

Given his risk tolerance, we landed on collaring the position while we harvest losses over 1–2 years. That way the value of the stock is protected.

Solution #2

His portfolio has no exposure to diversifying hedge fund strategies.

By taking a tax‑aware approach to that sleeve, we can expect to realize ordinary deductions along the way. For high earners in CA, a $500K deduction could be worth ~$250K of tax savings annually.

That directly attacks the W‑2 / RSU problem.

Solution #3

Instead of just swallowing a big, expensive mortgage, we’re looking at a hybrid structure:

Take a traditional mortgage in the $750K–$1M range

• Federal mortgage interest deduction cap is $750K
• California cap is $1M

Borrow the rest against his portfolio via a box spread loan at ~4%

Result:

• Lower blended financing rate
• Maintain tax benefits across the entire debt stack

Along the way, we’ll be:

• Diversifying his retirement accounts into private equity, credit, and infrastructure

Planning for him to stop working in ~5 years, at which point:

• Tax‑aware real estate can create tax‑favored income to replace salary
• Ordinary deductions from hedge funds + RE can fuel Roth conversions, shrinking the future RMD problem

If you’re in a similar spot - big portfolio, big RSUs, big tax bills, and big life decisions coming up, this is exactly what we specialize in.

†The interest rate and tax deduction savings interactive tool is for illustrative purposes only. Calculations assume interest rate savings equal to 2% of the loan amount and potential tax savings equal to 1% of the loan amount. Actual savings may vary based on market conditions, loan structure, tax circumstances, and individual client eligibility. Savings estimates are based on generalized assumptions and do not constitute tax, legal, or investment advice. Users should consult with their own financial or tax advisors to assess the applicability of any savings in their personal circumstances. This tool does not recommend or favor any specific investment and does not evaluate or compare a universe of alternative lending or investment options. Other financial solutions not analyzed here may offer similar or greater benefits.