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Zen and the Art of Real Estate Investing

Zen and the Art of Real Estate Investing

De: Jonathan Greene
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What if you could learn from experienced real estate investors, find out what got them to where they are now, get insight into their daily habits, and take these insights to inspire your own growth? That’s what each episode of Zen and the Art of Real Estate Investing brings. Hosted by Jonathan Greene, a real estate investor for more than 30 years, as well as advisor and coach, the founder of Streamlined Properties and the Team Leader of Streamlined Properties, brokered by Real, every episode is an in-depth look at the mindful approach to real estate investing. If you are looking to start from scratch, get to the next level, or just for a straightforward and honest approach to real estate investing, Zen and the Art of Real Estate Investing is the free mentorship program you can take with you anywhere.2024 Economía Finanzas Personales Gestión y Liderazgo Liderazgo
Episodios
  • 289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells

    289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells
    Oct 27 2025

    On this week's episode, Jonathan welcomes Jon Wells, a real estate matchmaker, syndicator, and longtime realtor with A Better Way Realty and managing partner at Alpha Network—for a candid look at what actually builds durable wealth. Jon traces his journey from early “fix-and-flips” to higher-conviction “fix-and-holds,” and ultimately to group homes leased on commercial-style terms. He explains why patience, operator quality, and underwriting discipline matter more than shiny objects, and how aligning with the right partners turns headaches into hands-off income.

    As the conversation unfolds, they unpack contractor pitfalls, slim-margin flips that turn into flops and the relief of triple-net-style leases where the business, not the landlord, handles the day-to-day. Jon shares why he prefers renting large, lightly modified homes to sober-living/mental-health operators (versus carving up houses), why meeting new operators is the hardest part of this niche, and how option agreements can create shared upside. They also dive into passive vs. active choices, due-diligence checklists for syndications, and the value of investing in what you truly understand.

    Listeners will come away with a calmer, longer-term lens: start with who you trust, de-risk with questions that reveal how an operator thinks, and don’t mistake speed for progress—especially when cash flow and sleep-at-night returns are the goal.

    In this episode, you will hear:

    • Why slim margins turn flips into long, stressful holds—and how to avoid it.

    • The group-home model Jon uses: bigger homes, egress and safety upgrades, and commercial-style leases to vetted operators.

    • Triple-net thinking for residential assets: fewer calls, clearer responsibility, steadier income.

    • Trust and due diligence: the questions that de-risk syndications and funds—and when “no answer” means “no deal.”

    • Why investing in what you actually know (and who you truly trust) beats chasing neon “opportunities.”

    • How to choose between passive and active plays based on temperament, skills, and season of life.

    Follow and Review

    If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show’s growth.

    Supporting Resources

    Connect with Jon Wells

    Website - www.abetterwayrealty.comFacebook - https://www.facebook.com/jonwells69Instagram - https://www.instagram.com/jonwells5280/Linkedin - https://www.linkedin.com/in/jonwellsrealtor/

    Connect with Jonathan

    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

    This episode was produced by Outlier Audio
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    49 m
  • 288: Building a Capital Gains Tax Exit Plan with Brett Swarts

    288: Building a Capital Gains Tax Exit Plan with Brett Swarts
    Oct 23 2025
    In 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: How the Deferred Sales Trust works as an alternative to 1031 exchanges Ways to defer capital gains taxes while maintaining investment flexibility Strategies for diversifying proceeds and protecting portfolio value Common misconceptions about tax-deferred exit strategies How estate and legacy planning can integrate with a DST Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. 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.
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    47 m
  • 287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte

    287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte
    Oct 20 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Luis Belmonte, a lifelong real estate investor, to explore the lessons he’s learned over decades of investing in multifamily, industrial, and commercial real estate across the U.S. and internationally. Luis shares his early experiences, including navigating the complexities of San Francisco’s real estate market in the pre-MLS era, identifying overlooked investment opportunities, and managing properties during challenging economic cycles. His stories reveal how creativity, persistence, and relationship-building have been central to his long-term success. Luis takes us back to his first multifamily acquisitions, explaining the strategies he used to uncover deals when information was scarce. From attending broker meetings with nothing but a notebook and a case of beer to identifying opportunities through obituaries, Luis emphasizes the importance of proactive deal sourcing and building relationships with those who have local knowledge. He also discusses the transformative effect of San Francisco rent control, illustrating how strategic management and patience can yield extraordinary returns over time. The conversation then shifts to international real estate development, highlighting the stark contrasts between regulations and construction practices in countries like Mexico and Japan compared to the United States. Luis recounts overcoming challenges such as unclear land ownership, lack of infrastructure, and differing bidding practices, underscoring the value of understanding local systems and collaborating with trusted partners. Whether navigating city politics in San Francisco or creating operational solutions abroad, Luis demonstrates that preparation and local expertise dramatically reduce risk and unnecessary costs. Jonathan and Luis also examine the current economic landscape, including interest rates and cyclical market patterns. Luis offers perspective on borrowing, refinancing, and interest rate history, reinforcing that measured and disciplined investing remains key, regardless of market fluctuations. Finally, Luis shares his preferred asset classes for long-term wealth creation: multifamily and warehouse properties. He emphasizes the importance of choosing an investment style aligned with one’s personality, seeking downside protection, and understanding operational realities to maximize returns. You’ll come away with practical advice on building sustainable real estate wealth, managing risk, partnering effectively, and identifying investment opportunities that others might overlook. Luis’s guidance is grounded in decades of real-world experience, making this episode essential for both new and seasoned investors looking to grow their portfolios with confidence. In this episode, you will hear: How Luis sourced early San Francisco deals before online MLS existed Creative approaches to finding undervalued properties and motivated sellers The impact of rent control on long-term investment returns Lessons from international real estate development in Mexico and Japan Strategies for partnering, reducing risk, and avoiding “stupid taxes” Luis’ preferred asset classes for consistent long-term wealth How interest rate cycles affect real estate investing and financing Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: Seven Hills Properties website - 7hp.com 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.
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    52 m
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