Before You Sell: The Capital Gains Move to Know

Before You Sell: The Capital Gains Move to Know

August 28, 2026 · 26 min

About this episode

Brett Rentmeester discusses how Opportunity Zones can help investors defer capital gains taxes and potentially earn tax-free appreciation.

Investors sitting on large gains may have a new way to defer taxes and potentially earn tax-free appreciation through Opportunity Zones. Brett Rentmeester of WindRock Wealth Management joins Maggie Lake to explain how the updated 2027 rules work, who they may benefit, and why gains realized in late 2026 could already qualify. They break down the 180-day rollover window, five-year tax deferral, 10% basis step-up, real estate depreciation benefits, and how certain Opportunity Zone investments can potentially grow tax-free if held for at least 10 years. Brett also explains the biggest risks, including illiquidity, bad real estate deals, and why the underlying investment still has to make sense before the tax benefits matter. If you have large capital gains from stocks, real estate, crypto, or the sale of a business, this is a strategy worth understanding before year-end. 💡 Brett Rentmeester explains how Opportunity Zones could help investors defer capital gains taxes, potentially unlock tax-free appreciation, and create new real estate opportunities — while also warning that the underlying investment still has to make sense. Sign up for a free portfolio review with one of…

People in this episode

Host: Maggie Lake

Guest: Brett Rentmeester

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Organizations: WindRock Wealth Management, Wealthion

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