Libsyn Directory

Episode 349: From Submarines to Self-Storage: Mastering 1031 Exchanges & DST Strategies, with Jim Whitesides

Release Date: 08/13/2025

How Real Estate Agents Win More Deals with New Construction, With Justin Bosak

Massive Passive Cash Flow Podcast

In this episode of the Massive Cash Flow Podcast, host Gary Wilson sits down with Justin Bozak, a top-producing real estate broker, team leader, and new construction specialist based in New Jersey’s Jersey Shore market. Justin is the founder of a rapidly growing brokerage with three offices, over 160 agents, and a fully built in-house support team, making him a true operator—not just a salesperson. Justin shares his unconventional journey from managing fast-food restaurants in the late 1990s to becoming a respected leader in residential sales, team building, and new construction real...

How to Scale Your Real Estate Business Across Multiple States for Agents Using Plug-and-Play Systems and AI, with Allan Burns

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How to Build Predictable Cash Flow for Real Estate Investors with Mike “Big Mike” Zlotnik

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Episode 364:How to Build Long-Term Cash Flow for Real Estate Investors,with Michael Pouliot

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How to Build Cash Flow Fast for Real Estate Investors Using Subject-To Deals, with Chris Prefontaine

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In this episode of the Massive Passive Cashflow Podcast, I sit down with Chris Prefontaine - creative financing expert, bestselling author, and founder of Smart Real Estate Coach. With 34+ years of hands-on investing experience, Chris shares how he rebuilt his real estate business after the 2008 crash by shifting to buying on terms—a strategy that allows investors to acquire properties without using their own cash, credit, or personally signing on bank loans. Chris breaks down why subject-to deals, 0% owner financing, and free-and-clear properties remain some of the most powerful tools for...

How to Find Profitable Real Estate Markets Using Data for Multifamily Investors, with Neal Bawa

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Mastering Airbnb: The Data-Driven Formula Behind Real Estate Success, With Kenny Bedwell

Massive Passive Cash Flow Podcast

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Distressed Deals, Passive Cash Flow, & Brokerage Success, with Justin Hoffman

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om Single-Family to “Forever Cashflow”: Mobile Home Park Strategy, Stability & Tax-Advantaged Returns with Jack Martin

Massive Passive Cash Flow Podcast

In this episode of the Massive Passive Cashflow Podcast, I sit down with investor and operator Jack Martin, Co-Founder & Chief Investment Officer of 52TEN, to break down why mobile home parks (MHPs) can be the most stable cash-flowing real estate when structured as tenant-owned homes (TOH) on leased land. From renovating SFRs and scaling multifamily to building an institutional-grade MHP platform, Jack explains the playbook: buy quality assets, stabilize, return capital, then keep the long-term coupon—with powerful bonus depreciation along the way. An Army veteran turned entrepreneur,...

From Corporate to Cash Flow: Real Estate Investing, Passive Income & Fund Strategies with Tom Dunkel

Massive Passive Cash Flow Podcast

In this episode of the Massive Passive Cashflow Podcast, I sit down with real estate investor and serial entrepreneur Tom Dunkel to unpack nearly 30 years of hard-won lessons in building wealth through strategic investing. From his early days in aerospace mergers and acquisitions to building a $63M distressed mortgage debt business, Tom shares how he transitioned from corporate finance to financial freedom—using real estate as the vehicle. As the Managing Director of Eagle Capital Investments, Tom has raised over $50 million across four asset classes and helped investors gain access to...

More Episodes

Jim Whitesides is a Naval Academy graduate, former nuclear submarine officer, and seasoned energy trader who transitioned into the self-storage business and real estate investment world. Drawing from decades of hands-on experience, Jim has helped countless investors navigate the complex waters of 1031 Exchanges and Delaware Statutory Trusts (DSTs). His unique blend of analytical precision, operational discipline, and strategic foresight allows him to break down complicated tax strategies into clear, actionable steps for investors at any stage. Whether you’re seeking to defer capital gains taxes, diversify your portfolio, or shift toward a more passive investment approach, Jim delivers insights grounded in real-world success.

What You Will Learn:

Who is Jim Whitesides?
How did Jim’s Naval Academy and submarine career shape his approach to business and investing?
What led Jim to transition from energy trading into self-storage and real estate?
How does a 1031 Exchange work, and what are the IRS rules you must follow?
Why are the timelines in a 1031 Exchange so critical — and so easy to miss?
What role does a Qualified Intermediary play in the process?
What is a Delaware Statutory Trust (DST), and how does it differ from traditional property ownership?
What are the key advantages and potential drawbacks of DSTs?
How can DSTs provide diversification and passive income while deferring taxes?
What strategies can investors use for debt replacement and portfolio restructuring?
How can sector specialization (like self-storage) be leveraged for consistent returns?
Real-world examples of successful transitions from active management to DST investing
How does Jim help investors avoid common tax-deferred exchange mistakes?
Where can listeners connect with Jim for further insights and guidance?

Additional Resources from Jim Whitesides:

Website: www.sound-tract.com

Instagram: https://www.facebook.com/people/Jim-Whitesides/61566366254034/

LinkedIn: https://www.linkedin.com/in/jimwhitesides

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