288: Building a Capital Gains Tax Exit Plan with Brett Swarts
Zen and the Art of Real Estate Investing
Release Date: 10/23/2025
318: The Rise of Mid-Term Rentals As Housing's Fastest-Growing Segment with Jeff Hurst
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jeff Hurst, CEO of Furnish Finder, to explore the fast-growing world of midterm rentals and why they’re becoming an increasingly attractive option for both renters and real estate investors. Jeff explains how monthly furnished rentals serve professionals, relocating families, and healthcare workers—distinctly different from traditional short-term vacation rentals. The conversation breaks down why midterm rentals often deliver better cash flow than long-term rentals with far less operational...
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317: How Commercial Real Estate Can Enrich The Lives of People at Work with Jonathan Iger
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by Jonathan Iger, CEO of Sage Realty Corporation, to explore how a 100-year-old, family-owned real estate company is redefining the modern office experience. Drawing on Sage’s deep roots in New York City office development, Jonathan explains how brand, hospitality, and operational excellence can drive higher tenant retention and long-term value creation. The conversation dives into why office real estate was already changing before COVID, how renewal rates are often misunderstood, and why “experience”...
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316: How To Break Through Your Income Ceiling With Real Estate with Stuart Gethner
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by Stuart Gethner, a longtime real estate investor, educator, and connector who has spent decades helping investors move from analysis into action. Stuart shares insights from his experience coaching investors and building his own portfolio across multiple market cycles. The conversation centers on why real estate is ultimately a people business. Stuart explains how networking, local market knowledge, and face-to-face relationships help investors avoid costly mistakes—especially when investing out of state...
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315: Thinking Outside the Short-Term Rental Box with Nick Korwin
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Nick Corwin, founder of Oak and Ember, to explore what it really looks like to move from long-term rentals into short-term hospitality and eventually into ground-up development. Nick shares how an engineering mindset, strong mentorship, and disciplined downside analysis shaped his early investing decisions. The conversation traces Nick’s evolution from owning Midwest long-term rentals to building unique short-term experiences in the Wisconsin Dells. He explains why chasing the middle of the market can...
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314: Why Higher Short-Term Rental Rates Start With Better Design with Bri West
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Bri West, co-founder of Somerled Designs, to explore how strategic design has become a competitive advantage in today’s short-term rental market. Drawing on her background in marketing and real estate investing, Bri explains why design should be treated as a revenue-driving investment rather than a cosmetic expense. The conversation dives into how niching down on a clear guest avatar, using data to guide design decisions, and prioritizing high-impact spaces can dramatically increase ADR—even if...
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313: Learning To Invest Beyond Multifamily In Growth Markets with Ash Patel
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Ash Patel, a commercial real estate investor with more than 15 years of experience investing beyond multifamily. Ash shares how an early mixed-use deal opened his eyes to the advantages of commercial assets and ultimately reshaped his entire investing approach. The conversation explores why many commercial assets are misunderstood or overlooked, including office, retail, medical, and mixed-use properties. Ash explains how changing work patterns, suburban growth, and market cycles are creating rare...
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312: A Playbook For Buying and Holding Rental Properties with Jennifer Ruelens
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jennifer Ruelens, a longtime property manager and unapologetic truth-teller in the real estate industry. With more than two decades of hands-on experience, Jennifer shares what buy-and-hold investors often misunderstand about property management, tenant relationships, and the real work required to make rentals perform over time. The conversation explores why real estate investing is rarely passive, how deferred maintenance and avoidance cost investors far more than management fees, and why many...
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311: Building a Wealth Creation Value-Add System with August Biniaz
Zen and the Art of Real Estate Investing
Jonathan Greene is joined by August Biniaz, co-founder and CIO of CPI Capital, to explore how early exposure to real estate shaped August’s investing philosophy and led him from single-family investing into large-scale multifamily and build-to-rent strategies. August shares how his family’s experience with real estate as a hedge against inflation influenced his long-term view on housing and capital preservation. The conversation dives into the realities of syndication, from learning the GP/LP structure through trial and error to building investor trust, infrastructure, and discipline over...
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310: Learning How To Invest Like a Billionaire with Bob Fraser
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Bob Fraser, bestselling author of Invest Like a Billionaire and CFO and Chief Macro Strategist at Aspen Funds. Bob shares how billionaire investors moved away from traditional 60/40 portfolios toward alternative investments—and why everyday investors can adopt the same mindset without billionaire-level wealth. Throughout the conversation, Bob explains why professionally managed real estate is often the most approachable entry point into alternatives, especially for investors who want...
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309: Redefining the Standards of Commercial Real Estate Services with Greg Trotter
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Greg Trotter, CEO and founder of Commercial Building Consultants, to unpack what real estate investors often miss during commercial due diligence. With over 40 years of experience in construction, inspections, and forensic building analysis, Greg explains how his role is to act as a “bodyguard” for investors—protecting their equity by identifying real risks before they close. Greg walks through how property condition assessments should align with an investor’s hold period and exit strategy,...
info_outlineIn this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Brett Swarts, founder of Capital Gains Tax Solutions, to explore strategies for minimizing capital gains taxes when selling real estate or business assets.
Brett Swarts is the founder of Capital Gains Tax Solutions, specializing in advanced strategies to help investors defer or eliminate capital gains taxes. With extensive experience in structuring Deferred Sales Trusts and other exit strategies, Brett has guided numerous real estate and business owners in building tax-efficient, long-term wealth plans.
Brett explains how the Deferred Sales Trust (DST) offers a flexible alternative to traditional 1031 exchanges, providing investors with greater control over timing, liquidity, and investment choices while deferring taxes in a manner that is legally compliant under IRS guidelines. Brett outlines the mechanics of a DST, detailing how proceeds from a sale can be structured to defer capital gains taxes and reinvest in a variety of assets. You’ll get insight into the advantages of a DST over standard tax-deferral methods, including reduced pressure to time the market, expanded diversification opportunities, and the ability to preserve wealth across multiple investment vehicles.
Jonathan and Brett also discuss common misconceptions about tax-deferred strategies, emphasizing the importance of understanding legal structures and working with experienced professionals. The conversation highlights how these tools can fit into a broader estate and legacy planning framework, ensuring that wealth is transferred efficiently to future generations while maintaining flexibility for investors today.
Several real-world examples demonstrate how investors have effectively utilized DSTs to manage risk, maintain cash flow, and safeguard portfolio value in dynamic markets. Brett emphasizes that while a DST can benefit many investors, it is particularly effective for those with significant gains, complex portfolios, or long-term wealth preservation goals. The discussion concludes with actionable guidance on evaluating whether a DST aligns with an investor’s exit strategy and long-term financial objectives.
By the end of this episode, you’ll understand how to approach capital gains tax planning strategically, integrating DSTs into their broader real estate and business investment strategies. Jonathan and Brett provide a clear framework for deferring taxes, diversifying holdings, and protecting wealth, enabling investors to make informed decisions that align with both their financial and personal objectives.
In this episode, you will hear:
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How the Deferred Sales Trust works as an alternative to 1031 exchanges
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Ways to defer capital gains taxes while maintaining investment flexibility
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Strategies for diversifying proceeds and protecting portfolio value
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Common misconceptions about tax-deferred exit strategies
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How estate and legacy planning can integrate with a DST
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Supporting Resources:
Capital Gains Tax Solutions website - www.capitalgainstaxsolutions.com
Build It To Billions on YouTube - www.youtube.com/@BuildItToBillions
Brett Swarts on Facebook - www.facebook.com/brett.swarts
Brett’s Instagram - instagram.com/brett_swarts
Connect with Brett on LinkedIn - www.linkedin.com/in/brett-swarts
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
TikTok - www.tiktok.com/@trustgreene
Zillow - www.zillow.com/profile/StreamlinedReal
Bigger Pockets - www.biggerpockets.com/users/TrustGreene
Facebook - www.facebook.com/streamlinedproperties
Email - info@streamlined.properties
Episode Credits
If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.