Private equity partner with $12M portfolio in the 37% tax bracket

Currently just public stocks/bonds across:

• $2.2M in retirement accounts
• $9.8M in taxable accounts

Opportunities we’re executing:

• Upgrade tax-loss harvesting: Moving from direct indexing to a long/short equity SMA for outperformance potential and permanent capital loss harvesting — critical for PE partners with ongoing capital gains/carry.

• Diversify into tax-aware hedge funds: Lower correlation to stocks/bonds while passing through ordinary losses to offset earned income.

• Super Duper Mega Tax-Free Roth Conversion™: With earned income dipping during his new firm’s launch, we can convert the $2.2M retirement balance to Roth over 3–5 years at ultra-low tax cost.

• Higher-octane illiquids in Roth: Private equity, infrastructure, and credit — all in the tax-free growth bucket.

• Estate planning on the radar: No pressing need yet, but planning early so growth and business value don’t create avoidable estate tax issues later.

• Cheap, tax-deductible leverage: Borrowing at sub-4% via box spreads instead of a bank line at 7%+, with the interest deductible against investment gains.