De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion

Tax-loss harvesting, giving, wrapping up the year in style

Andre and Brent talk about Hawaiian shirts and tax-loss harvesting in December, literally cleaning out the closet, keeping in shape, state and local taxation, what went well in 2025, what didn't go as well, and what's looking good in 2026.

End-of-Year Tax and Investment Planning ...for Nerds

Andre and Brent talk all things year-end planning. This includes backdoor Roths, preventing tax surprises and penalties, and giving stuff away is easy, but tax planning is hard. Sunglasses and Hawaiian shirts make an appearance. Thanks to Paul Roberts for the original music! Educational content. Not investment, tax, or legal advice. Hire an adviser for personalized guidance.

De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion

Andre and Brent walk through the thorny problem of concentrated stock. They cover the plain option (just sell and pay the tax) then unpack alternatives: tax-loss harvesting over time, tax-aware long/short strategies using leverage, exchange funds, and CRUTs. They even touch on seeding new ETFs in-kind using Section 351 conversions. Along the way, Costco avocados and breakfast choices make a cameo.

Climbing The Wealth Ladder With Nick Maggiulli

The Not Advice Podcast welcomes Nick Maggiulli (Dollars and Data, COO at Ritholtz Wealth) to talk through his new book The Wealth Ladder. We cover the six stages of wealth, why income drives everything, how leverage and concentration shape outcomes, and why skipping rungs can backfire. Plus: avocado tariffs, the 0.01% rule, and why happiness isn’t just about money. Disclosure: This conversation is for informational and entertainment purposes only. It is not financial, legal, or tax advice. Always consult a qualified professional about your specific situation.

Holding Too Much Company Stock?

The Not Advice Podcast is back. Andre Nader and Brent Sullivan dig into concentrated stock positions, like how they happen, when they become dangerous, and what to do about them. We cover selling vs. hedging vs. exchange funds, why paying the tax bill isn’t always a bad idea, and how FIRE math changes when half your net worth is riding on a single ticker. Plus: avocado metaphors and sequence-of-return risk. Disclosure: This conversation is for informational and entertainment purposes only. It is not financial, legal, or tax advice. Always consult a qualified professional about your specific situation.