Jon Lontai began his career in traditional brokerage at TD Ameritrade before transitioning into alternative investments with a fiduciary RIA. Through working with higher-net-worth clients, he discovered that traditional investment tools were no longer enough to provide meaningful value.
This led him into the world of alternative investments, particularly private real estate, private debt, and tax-efficient strategies designed to defer capital gains.
A major focus of the episode is the 1031 Delaware Statutory Trust (DST) — a structure that allows investors to defer capital gains from real estate while becoming passive owners in professionally managed properties. These investments typically generate steady income and eliminate the responsibilities of direct property ownership.
Jon also explains how DSTs can serve as a backup option in a traditional 1031 exchange, helping investors avoid the pressure of tight identification deadlines.
The conversation expands into Opportunity Zones, advanced tax planning strategies, and the importance of coordinating between financial advisors, CPAs, and attorneys to build an effective long-term wealth strategy.
Ultimately, the episode highlights how investors approaching retirement or seeking passive income can use these tools to simplify their portfolios while preserving wealth.
Watch the episode here
Listen to the podcast here
📘 Overview
In this episode of the Generations of Wealth Podcast, Derek sits down with alternative investment specialist Jon Lontai to explore advanced tax strategies that many real estate investors and advisors overlook.
Jon explains how tools like 1031 Delaware Statutory Trusts (DSTs), Opportunity Zones, and alternative investments can help investors defer capital gains, create passive income, and transition away from active property management.
The discussion dives into how these strategies work, who they are best suited for, and why many real estate professionals and CPAs are not fully utilizing them. For investors looking to preserve wealth and minimize taxes while maintaining exposure to real estate, this episode offers a powerful perspective.
⭐ Key Takeaways
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Alternative investments are becoming increasingly important for higher-net-worth investors
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1031 DSTs allow investors to defer capital gains while becoming passive real estate investors
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DSTs often generate 5–6% passive income distributions
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Opportunity Zones can provide long-term tax advantages on capital gains
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DSTs can serve as a backup option in traditional 1031 exchanges
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Liquidity and control are key considerations when choosing passive investments
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Tax planning should involve coordination between CPAs, attorneys, and financial advisors
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Many CPAs focus only on short-term tax strategies instead of long-term planning
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Real estate investors approaching retirement often shift toward passive ownership structures
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Alternative investments require careful due diligence but can be powerful wealth tools
💬 Relevant Topics Discussed
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1031 Delaware Statutory Trusts explained
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Opportunity Zone tax strategies
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Passive real estate investing
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Capital gains deferral strategies
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Alternative investments vs traditional portfolios
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Liquidity and control considerations
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Coordination between CPAs, attorneys, and advisors
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Trends in tax-efficient investing
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Retirement planning for real estate investors
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The growing demand for passive investment structures
🎧 Why Should You Listen?
Listen to this episode if you:
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Are selling real estate and facing large capital gains taxes
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Want to transition from active investing to passive income
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Are curious about advanced tax strategies beyond traditional 1031 exchanges
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Want to understand how alternative investments fit into a long-term wealth strategy
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Want to diversify beyond owning individual properties
This episode opens the door to strategies many investors don’t learn about until much later in their careers.
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About Jon Lontai
Jon Gabriel Lontai is the Vice President at Arcus Capital Partners, where he focuses on investment strategy, capital markets, and the development of high-quality real estate and private investment opportunities. With a strong background in finance and business, Jon works closely with investors and partners to identify strategic opportunities and drive long-term value creation.
A graduate of the Illinois Institute of Technology’s Stuart School of Business, Jon combines analytical insight with a disciplined approach to investment management.
At Arcus Capital Partners, he plays a key role in evaluating projects, structuring investments, and supporting the firm’s mission of delivering strong performance through thoughtful asset selection and strategic execution.