$30m portfolio with $2m of income

Fully liquid.
Public markets only.
Simple.

That’s not wrong.

But it leaves two massive issues:

1. Enormous tax inefficiency
2. Very little true diversification (stocks drive most of the risk)

If you have $30M, you don’t need 15% returns.

You need steady compounding in the lowest-risk, most tax-efficient way possible.

Here’s what I’d do:

1. Implement a long/short overlay on low-basis index funds

Instead of selling and triggering capital gains:

• Add a differentiated return stream
• Systematically harvest capital losses
• Offset gains from future liquidity events
• Reduce pure equity concentration

This is the starting point because it allows us to rebalance the portfolio in a tax-neutral fashion.

2. Allocate across multiple tax-aware hedge funds

Not one.
Three.

Uncorrelated strategies improve the overall risk-to-return profile versus owning any single one in isolation.

Bonus:

• Realize ordinary loss deductions
• Offset earned income
• Create flexibility for Roth conversions before RMDs

Portfolio construction and tax planning should work together.

3. Add private real estate

Many people got burned in real estate the last few years.

It’s a different environment now with:

• Loans maturing
• Sellers under pressure
• Valuations reset
• New underwriting at today’s rates

Depreciation, cash out refis, and 1031 exchanges enhance after-tax returns.

4. Add infrastructure

• Low correlation to equities
• Yield
• Inflation hedge
• Essential asset exposure

The demand for power, particularly from AI and data centers, is massive.

That capital needs to come from somewhere.

5. Securitized affordable housing loans

Double-digit tax-exempt yields.
High quality assets that have been resilient through cycles historically.

6. Put private equity inside Roth accounts

Highest expected return assets belong in the most tax-efficient bucket.
Let it compound tax-free for generational wealth transfer.

At $30M, reducing risk through diversification is the #1 objective.

This playbook would:

• Broaden return drivers
• Reduce correlation
• Improve after-tax returns
• Sequence Roth conversions intelligently
• Avoid unnecessary equity concentration

This isn’t complexity for complexity’s sake.

It’s about cutting taxes and reducing risk in a way vanilla portfolios don’t.