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Matt Bucklin on The Crux: How 351 Tax-Deferred Exchanges Turn Concentrated Stock Into ETFs Without Capital Gains

Investing

From Concentrated Stocks to Diversified ETFs: The Tax-Smart Way

How 351 tax-deferred exchanges help investors diversify without the capital gains hit

The Challenge Every Concentrated Stock Investor Faces

Picture this: You’ve held onto company stock for years, watching it appreciate significantly. Now you want to diversify your portfolio, but there’s a problem—selling would trigger a massive capital gains tax bill. What if there was a way to convert that concentrated position into a diversified ETF portfolio without paying taxes upfront?

That’s exactly what ExchangiFi founder Matt Bucklin explains in his recent appearance on The Crux podcast with Eben Burr, President of Toews Asset Management.

What Are 351 Tax-Deferred Exchanges?

Think of a 351 exchange as a sophisticated swap: you exchange your appreciated stock for shares in a diversified ETF, and the IRS treats it as a tax-neutral transaction. Instead of paying capital gains immediately, the tax obligation transfers to your new ETF position.

The beauty? You get instant diversification while deferring taxes until you eventually sell the ETF shares.

Why Matt Bucklin Built ExchangiFi

Bucklin recognized that while 351 exchanges were powerful, they were also complex and inaccessible to most investors and advisors. ExchangiFi streamlines the entire process, making these tax-efficient strategies available to a broader audience.

During the interview, Bucklin shares:

  • His journey into asset management
  • How ExchangiFi simplifies the 351 exchange process
  • Why he believes tax efficiency will define the future of investing

Who Benefits Most?

For Individual Investors:

  • Those with concentrated stock positions from company equity, inheritance, or long-term holdings
  • Anyone looking to diversify without triggering immediate tax consequences

For Financial Advisors:

  • A new tool to help clients reduce single-stock risk
  • A way to demonstrate value through tax-smart portfolio transitions

The Bigger Picture: ETFs and Tax Efficiency

The conversation goes beyond just 351 exchanges. Bucklin and Burr discuss how ETFs are reshaping the investment landscape and why tax-smart strategies are becoming essential for modern portfolio management.

Key Takeaways from the Interview

Watch the full conversation to discover:

The step-by-step mechanics of how 351 exchanges actually work

Real tax benefits of converting stock positions to ETFs

Why tax efficiency is becoming the competitive advantage in asset management


Ready to learn more? Watch the complete interview below to see how 351 tax-deferred exchanges could transform your approach to portfolio diversification.

The information provided is for educational purposes only and should not be considered tax or investment advice. Consult with qualified professionals before making any financial decisions.

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