Private Equity Partner with an $8M Portfolio in the 37% Tax Bracket

Currently allocated across public stocks and bonds:

$1.2M in retirement accounts

$6.8M in taxable accounts

Opportunities We’re Executing

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

Diversify into tax-aware hedge funds: Lower correlation to traditional markets while passing through ordinary lossesto offset earned income.

Super Duper Mega Tax-Free Roth Conversion™: With income dipping during his new firm’s launch, we can convert the entire $1.2M retirement balance to Roth over 2–3 years at ultra-low tax cost.

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

Estate planning on the radar: No immediate need, but planning early ensures future growth and business value don’t trigger avoidable estate-tax issues.

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

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