Zen and the Art of Real Estate Investing

Jonathan Greene
  • 4.9 (106)
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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.

  1. 320: Merging Realty, Development, and Management with Ryan Cadwell

    14H AGO

    320: Merging Realty, Development, and Management with Ryan Cadwell

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Ryan Cadwell, partner at Resolute RDM, to unpack how "dumb money" and undisciplined underwriting have distorted real estate markets over the last cycle. Ryan shares how cheap capital, short-term thinking, and inexperienced investors created inflated valuations that are now forcing hard lessons as loans reset and assumptions break. The conversation dives deep into why advisory services matter more than ever, especially for out-of-state investors and newer buyers navigating markets they don't fully understand. Ryan explains why spreadsheets alone don't make good investments, how lenders' incentives can misalign with investors', and why slowing down often leads to better long-term outcomes. Jonathan and Ryan also explore the human side of real estate, from landlord-tenant dynamics to the emotional toll of DIY management. They discuss why many investors unknowingly trade time freedom for stress, how ego and vanity metrics like "door count" lead to poor decisions, and why knowing what you actually want from real estate is more important than chasing trends. In this episode, you will hear: Why "dumb money" helps on the sale but hurts on the next buy How cheap debt masked bad underwriting during the last cycle Why lenders are not always the safety net investors assume The difference between buying property and actually investing How property management fees often save money long-term Why asset management matters more than owning more doors 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 Ryan: Website: http://www.resoluterdm.com/  Youtube: https://www.youtube.com/@resoluterdm  Facebook: https://www.facebook.com/ryancadwell  Instagram: https://www.instagram.com/resoluterdm/  LinkedIn: https://www.linkedin.com/in/ryancadwell/  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    54 min
  2. 319: Getting Dirt Rich Through Land Investing and Development with Jose Berlanga

    3D AGO

    319: Getting Dirt Rich Through Land Investing and Development with Jose Berlanga

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene welcomes back Jose Berlanga, real estate developer, builder, and author, for a deep dive into land investing, development strategy, and the lessons learned from more than 30 years in the business. Returning to the show with his new book, Dirt Rich: Explore the World of Land Investing and Development, Jose shares how land deals played a critical role in capitalizing his construction company and shaping his long-term investment approach. The conversation explores the realities of land development, including zoning challenges, neighborhood resistance, entitlement risk, and why so many investors underestimate the complexity of building from the ground up. Jose explains the importance of repetition, local expertise, and understanding your niche, emphasizing that successful developers stick to what they know rather than constantly reinventing the wheel. Jonathan and Jose also discuss timing market cycles, the role of capital reserves during downturns, and why reputation, relationships, and integrity matter more than squeezing every dollar out of a single deal. The episode offers a grounded look at land as the foundation of all real estate value and why patience, vision, and long-term thinking are essential for lasting success. In this episode, you will hear: How land flipping helped fund and grow a construction business Why zoning, permitting, and community dynamics make land development complex The risks of jumping into development without experience or local knowledge Why repetition and staying in one niche lead to better outcomes How reputation and long-term relationships create deal flow over time 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 Jose: Jose's first appearance on the show: https://zenandtheartofrealestateinvesting.com/podcast/211/  Website: https://joseberlanga.com/  Facebook: https://www.facebook.com/authorjoseberlanga  Instagram: https://www.instagram.com/authorjoseberlanga/  LinkedIn: https://www.linkedin.com/in/jose-berlanga-900a9518/  Jose's Books: https://joseberlanga.com/books/  Jose's New Book: https://www.amazon.com/Dirt-Rich-Jose-M-Berlanga-ebook/dp/B0FRNHY6PC  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    1h 3m
  3. 318: The Rise of Mid-Term Rentals As Housing's Fastest-Growing Segment with Jeff Hurst

    FEB 5

    318: The Rise of Mid-Term Rentals As Housing's Fastest-Growing Segment with Jeff Hurst

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jeff Hurst, CEO of Furnished 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 intensity than short-term rentals. Jeff also shares insights from Furnished Finder's first-of-its-kind housing market report, created in partnership with AirDNA, revealing just how durable and widespread demand for monthly rentals has become across the U.S. Listeners will walk away with a clearer understanding of where midterm rentals fit between long-term and short-term housing, how investors are discovering this niche, and why this category may continue to grow as housing affordability, mobility, and lifestyle preferences evolve. In this episode, you will hear: Why midterm rentals serve a fundamentally different tenant base than short-term rentals How furnished monthly rentals can outperform long-term rentals with less management Key insights from the Furnished Finder and AirDNA housing market report Why hospitals, universities, and commuter corridors are strong midterm rental locations How investors can reduce risk by underwriting midterm rentals as long-term deals 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 Jeff:  Website: http://www.furnishedfinder.com/  Youtube: https://www.youtube.com/@FurnishedFinder  Facebook: https://www.facebook.com/FURNISHEDFINDER  Instagram: https://www.instagram.com/furnishedfinder/  LinkedIn: https://www.linkedin.com/company/furnished-finder/  The Report: https://www.furnishedfinder.com/resources/monthly-rental-market-trends-report  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    51 min
  4. 317: How Commercial Real Estate Can Enrich The Lives of People at Work with Jonathan Iger

    FEB 2

    317: How Commercial Real Estate Can Enrich The Lives of People at Work with Jonathan Iger

    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" has become a core driver of NOI and asset performance. Jonathan also shares how Sage applies hospitality principles like consistency, service recovery, and "surprise and delight" to create differentiated office environments that tenants don't want to leave. Listeners will gain insight into where the office market is heading, how branded office platforms can create alpha for investors, and why the future of office belongs to owners who treat buildings as long-term relationships rather than short-term transactions. In this episode, you will hear: How Sage Realty evolved from traditional office ownership into a branded office platform Why tenant renewal rates are far lower than most underwriting assumptions The role of hospitality, SOPs, and service recovery in commercial real estate How experience-driven offices can increase rents, NOI, and long-term asset value Why office real estate isn't dead, but fundamentally changing 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 Jonathan: Website: https://sagerealty.com/  Instagram: https://www.instagram.com/experience_sage/  LinkedIn: https://www.linkedin.com/company/sage-realty-corporation/  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    1 hr
  5. 316: How To Break Through Your Income Ceiling With Real Estate with Stuart Gethner

    JAN 29

    316: How To Break Through Your Income Ceiling With Real Estate with Stuart Gethner

    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 or relying too heavily on online education. He and Jonathan discuss the limits of "YouTube University" and why real confidence comes from real conversations with experienced investors. Jonathan and Stuart also dive into partnerships, property management, and investor self-awareness. From understanding your personal strengths to building complementary partnerships and avoiding shiny object syndrome, the episode emphasizes patience, humility, and long-term thinking as foundations for sustainable investing success. In this episode, you will hear: Why networking groups accelerate investor confidence and clarity The risks of relying solely on online education without local insight How partnerships work best when both sides have equal skin in the game Why investing close to home often reduces operational risk How patience and long-term thinking outperform "get rich quick" strategies 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 Stuart:  Website: http://www.stuartgethner.com/  Youtube: https://www.youtube.com/@StuartGethner  Facebook: https://www.facebook.com/people/Gethner-Education-Consulting/61578852277422/  Instagram: https://www.instagram.com/stuartgethner  LinkedIn: http://linkedin.com/in/stuartgethner/  TikTok: https://www.tiktok.com/@stuart_gethner  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    55 min
  6. 315: Thinking Outside the Short-Term Rental Box with Nick Korwin

    JAN 26

    315: Thinking Outside the Short-Term Rental Box with Nick Korwin

    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 be a losing strategy, how combining units and serving overlooked guest segments created an edge, and why operating short-term rentals requires far more systems and empathy than most investors expect. Jonathan and Nick also unpack the realities of entitlement risk, zoning battles, and development timelines. Nick offers a candid look at what it takes to push a project through local approvals, manage rising costs, and stay grounded when timelines and budgets inevitably expand. In this episode, you will hear: Why testing whether you even like being a landlord matters before scaling How Nick identified underserved short-term rental niches instead of competing in crowded markets The operational differences between long-term rentals and hospitality businesses Lessons learned from zoning, entitlement hurdles, and community resistance Why doubling both your budget and timeline can save you from painful surprises 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 Nick: Website: http://www.stayoakandember.com/  Youtube: https://www.youtube.com/@Korwinning  Instagram: https://www.instagram.com/korwinning/  LinkedIn: https://www.linkedin.com/in/korwinning/  TikTok: https://www.tiktok.com/@korwinning  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    52 min
  7. 314: Why Higher Short-Term Rental Rates Start With Better Design with Bri West

    JAN 22

    314: Why Higher Short-Term Rental Rates Start With Better Design with Bri West

    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 occupancy is lower. Bri also shares insights from managing and designing hundreds of short-term rentals nationwide, including common mistakes investors make, how to think about amenities and bed configurations, and why lifestyle photography and branding are no longer optional. Listeners will come away with a clearer framework for evaluating short-term rental opportunities, aligning design with long-term investment goals, and standing out in increasingly saturated markets. In this episode, you will hear: Why short-term rental design should start with data and investment strategy, not personal taste How niching down on a specific guest experience can outperform "general" properties The role of amenities, durability, and bed layout in guest satisfaction and reviews Why branding and lifestyle photography directly impact bookings and pricing power How to think about long-term competitiveness as markets become more saturated 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 Bri: Website: https://www.somerleddesigns.com/  Instagram: https://www.instagram.com/somerled.designs/  LinkedIn: https://www.linkedin.com/company/somerled-designs/  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    59 min
  8. 313: Learning To Invest Beyond Multifamily In Growth Markets with Ash Patel

    JAN 19

    313: Learning To Invest Beyond Multifamily In Growth Markets with Ash Patel

    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 opportunities to acquire high-quality commercial buildings at deep discounts, often well below replacement cost. Jonathan and Ash also dig into the mindset required to succeed in real estate, the dangers of chasing trends promoted on social media, and why newer investors may benefit from escaping overcrowded asset classes. This episode offers a grounded look at how flexibility, curiosity, and long-term thinking can open doors to less competitive—and often more resilient—investment opportunities. In this episode, you will hear: How Ash transitioned from residential and mixed-use into commercial real estate Why office, retail, and medical assets are misunderstood by many investors How market cycles create opportunities across different commercial asset classes The risks of following social-media-driven investment trends Why parking, location, and tenant mix matter more than asset labels How mindset plays a larger role than mechanics in long-term success 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 Ash: Website: http://www.investbeyondmultifamily.com/  Youtube: https://www.youtube.com/@ashpatel_official  Facebook: https://www.facebook.com/ash.patel.58118  Instagram: https://www.instagram.com/ashpatel_official/  LinkedIn: https://www.linkedin.com/in/ash-patel-95b1a25/  TikTok: https://www.tiktok.com/@ashpatel_official  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

    56 min
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About

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.

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