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#199: Turning Properties into Portfolios: 1031 Exchanges and Portfolio Management

In this episode of the Calibrate Real Estate Podcast, host Kyle Malnati interviews Jeff Bemis, co-founder of 1031 Specialists. Jeff shares his background, moving from a finance career at Ernst & Young and Rimrock Capital Management to real estate, and introduces the firm’s focus on helping clients navigate 1031 and 721 exchanges. Kyle and Jeff explore how longtime landlords, often tired of the day-to-day management of properties, are increasingly looking toward Delaware Statutory Trusts (DSTs) and other vehicles to achieve diversification, professional management, and passive income.

The discussion dives into the mechanics and advantages of 721 exchanges, which allow investors to transition from owning individual properties into shares of large real estate investment trusts (REITs). Jeff explains how this strategy provides access to portfolios of hundreds of properties across multiple markets, offering diversification, reduced management burdens, and potential tax deferral benefits. He contrasts the traditional 1031 exchange, which keeps investors tied to singular property ownership, with the 721 structure that opens doors to fractional ownership in institutional-grade assets.

Risk management, diversification, and life-stage strategy. Jeff draws on personal and professional experiences, including insights from managing large hedge funds and advising family members, to highlight the importance of aligning investments with lifestyle and risk tolerance. He also stresses the value of relationships and consistency in business, sharing how steady communication builds trust over time. The episode closes with a reflection on discipline, patience, and the long-term benefits of forging strong connections while making thoughtful, well-structured investment decisions.

Here are 5 key takeaways:

Relationships Drive Success: Consistent communication and genuine relationship-building—whether through newsletters, regular calls, or networking—often create long-term trust and business opportunities.

1031 vs. 721 Exchanges: A 1031 keeps investors in direct property ownership, while a 721 allows them to roll into REITs for diversification and passive income without triggering immediate taxes.

Diversification Benefits: Moving from a single property to fractional ownership in large portfolios spreads risk across property types, markets, and geographies.

Best Fit for Aging Investors: 721 exchanges and DSTs often appeal to older landlords seeking professional management, liquidity, and stable income instead of active property management.

Risk Management & Discipline: Investment success relies less on hitting every winner and more on structuring deals to win more than you lose, and sizing positions wisely.

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Written & Produced by Andrew Foresman
Hosted by Kyle Malnati


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