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

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Not Advice

Andre Nader (FAANG Fire), Brent Sullivan (Tax Alpha Insider)

4 episodes

5 days ago

A podcast about investing, taxes, RSUs, corporate life, retiring early, and avocados.

Investing

Business

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All content for Not Advice is the property of Andre Nader (FAANG Fire), Brent Sullivan (Tax Alpha Insider) and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

A podcast about investing, taxes, RSUs, corporate life, retiring early, and avocados.

Investing

Business

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

Not Advice

1 hour 38 minutes 1 second

1 month ago

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.