CA business owner with $17M portfolio

Currently just public stocks/bonds across:

• $6M in retirement accounts
• $11M 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 persistent capital loss harvesting.

• 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 the cyclicality of the business and ordinary deductions, we can convert meaningful amounts of the retirement balance to Roth during low income years at ultra-low tax cost.

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

• Manufactured home community deals resulting in 1.7x depreciation back on invested capital. For example, $1m invested can realize $1.7m of passive losses in year 1. Can be used to offset the passive income from some partnerships that he’s an investor in.

• 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.