Zen and the Art of Real Estate Investing

Jonathan Greene
  • 4.9 (108)
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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. 349: How To Find, Hire, and Fire Property Managers with Jennifer Ruelens

    1D AGO

    349: How To Find, Hire, and Fire Property Managers with Jennifer Ruelens

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews returning guest Jennifer Ruelens, founder of One Focus Property Management in Central Pennsylvania. Jennifer shares a practical guide for buy-and-hold investors on how to find, hire, manage, and ultimately fire a property manager when necessary. Drawing from her experience overseeing more than 600 units, she explains why property management is often misunderstood and how investors can better protect their assets by asking smarter questions and setting clearer expectations. Jennifer breaks down the most important factors investors should evaluate before hiring a management company, including licensing, trust accounting, operational structure, and oversight. She explains why many property management companies operate with weak systems or poor supervision and why investors should understand exactly who is handling their money, security deposits, tenant communication, and day-to-day operations. The conversation also explores how inexperienced investors often mistake accessibility for professionalism and why strong systems and boundaries are critical for long-term property performance. Jonathan and Jennifer also discuss the operational realities of property management, including tenant screening, lease enforcement, maintenance coordination, and capital improvement planning. Jennifer explains why property management should function like a systems-driven business rather than a reactive side hustle and why many traditional real estate agents struggle with the operational demands of managing rental properties effectively. They also examine the warning signs investors should look for when a property manager is underperforming or allowing deferred maintenance and tenant issues to spiral out of control. The conversation also focuses heavily on transitions and accountability. Jennifer shares how investors should approach difficult conversations with property managers, what to inspect and monitor on an ongoing basis, and how to professionally terminate a management relationship when things are no longer working. Throughout the episode, both Jonathan and Jennifer emphasize that great property management is one of the most important factors in protecting long-term wealth for buy-and-hold investors. In this episode, you will hear: • What investors should ask before hiring a property manager • Why licensing, trust accounts, and financial oversight matter in property management • How to evaluate property managers by experiencing the tenant process firsthand • Why property management requires systems, operations, and strong boundaries • The warning signs that a property manager may be underperforming • How to professionally transition away from a bad property management relationship • Why proactive maintenance and capital planning protect long-term investment value 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 the show and supports its continued growth. Supporting Resources Connect with Jennifer Website: http://www.holditwithpmjen.com/  Youtube: https://www.youtube.com/@HoldItwithPMJen  Facebook: https://www.facebook.com/HoldItwithPMJen/  Instagram: https://www.instagram.com/holditwithpmjen/  LinkedIn: https://www.linkedin.com/in/jenniferruelens/  TikTok: https://www.tiktok.com/@holditwithpmjen  Article: https://www.linkedin.com/pulse/buy-hold-investors-guide-finding-hiring-firing-property-ruelens-evm1e/  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.

    50 min
  2. 348: Everything You Need To Know About House Hacking

    5D AGO

    348: Everything You Need To Know About House Hacking

    *]:pointer-events-auto R6Vx5W_threadScrollVars scroll-mb-[calc(var(--scroll-root-safe-area-inset-bottom,0px)+var(--thread-response-height))] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" data-turn-id="9763cd24-b383-4e01-bd5b-dea4b511b128" data-turn-id-container="9763cd24-b383-4e01-bd5b-dea4b511b128" data-testid="conversation-turn-6" data-scroll-anchor="false" data-turn="assistant"> On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene delivers a solo episode breaking down everything investors need to know about house hacking. Drawing from years of experience helping clients purchase multifamily properties, Jonathan explains why house hacking remains one of the most effective ways for new investors to reduce housing costs, build equity, and learn the fundamentals of landlording — even in today's high-interest-rate environment. Jonathan walks through the practical side of evaluating house hack opportunities, including what types of properties to target, how to identify strong layouts, and why uneven multifamily setups can create major financial advantages. He also explains the importance of understanding lease structures, separated utilities, parking, laundry, and accessory dwelling units, while highlighting common mistakes that inexperienced investors and agents often make during the process. The episode also explores how house hacking can evolve into larger investing strategies over time. Jonathan discusses using mid-term and short-term rentals to increase income potential, leveraging mixed-use properties with owner-occupied financing, and turning a first house hack into a long-term portfolio-building tool. Rather than chasing unrealistic cash flow projections, he encourages listeners to focus on lowering living expenses, gaining experience, and building flexibility into their investing plans. Throughout the conversation, Jonathan emphasizes the importance of working with knowledgeable professionals and approaching house hacking with realistic expectations. He shares insights on tenant communication, property management, and why the right realtor can make or break a successful deal. Ultimately, the episode serves as a practical roadmap for anyone considering their first real estate investment through house hacking. In this episode, you will hear: • Why reducing housing costs should be the primary goal of house hacking • What investors should look for in multifamily properties and uneven unit layouts • How ADUs, "two plus one" properties, and mixed-use buildings can create additional opportunities • Why most real estate agents do not fully understand house hacking strategies • How midterm and short-term rentals can increase income potential over time • The importance of tenant relationships, lease verification, and proper due diligence before closing 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 the show and supports its continued growth. Supporting Resources Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com   This episode was produced by Outlier Audio.

    37 min
  3. 347: Real Estate Investing Lessons From My Dad

    MAY 18

    347: Real Estate Investing Lessons From My Dad

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a personal solo episode reflecting on the 10 most important real estate investing lessons he learned from his father. Drawing from childhood memories, years of investing experience, and lessons shaped through both success and failure, Jonathan explains how his dad's practical wisdom helped form the mindful investing philosophy that defines the podcast today. Throughout the episode, Jonathan breaks down principles that apply far beyond real estate transactions. From "don't rush life" to "learn to walk away," he explains how patience, preparation, and emotional discipline can protect investors from costly mistakes. He also explores how ego often sabotages deals and why understanding leverage, timing, and human behavior can make investors more successful over the long term. Jonathan also reflects on the deeply relationship-driven nature of real estate investing. Whether negotiating with sellers, managing tenants, or working with partners, he emphasizes the importance of honesty, empathy, and communication. He shares stories about how his father approached tenants with compassion, built trust through straightforward conversations, and viewed long-term relationships as more valuable than winning short-term arguments. The episode also highlights the value of staying curious and opportunity-focused as an investor. Jonathan discusses why investors should always be looking for overlooked opportunities, remain open-minded about unconventional asset classes, and understand that some of the best deals come from thinking differently than everyone else. Ultimately, the conversation is a reminder that successful investing is not only about numbers and strategy, but also about mindset, patience, and the way you treat people.   My Top 10 Lessons: 1. Don't rush life 2. Don't be stingy, but be firm 3. Learn to walk away 4. Sell anything if someone will pay you enough 5. Buy weird shit at the right price 6. ABL (Always be looking) 7. Everything is about relationships 8. Always see the good in people 9. Expect partners to walk away 10. Let people have their story   In this episode, you will hear: • Why "don't rush life" is one of the most important lessons for real estate investors • How learning to walk away can become a powerful negotiation advantage • Why strong relationships and trust matter more than aggressive tactics • How Jonathan's father approached tenants, partnerships, and difficult negotiations with empathy • Why investors should stay open to unconventional opportunities and "weird" properties • The importance of emotional discipline, patience, and long-term thinking in real estate investing 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 the show and supports its continued growth. Supporting Resources Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com

    42 min
  4. 346: The 10 Best Books For Real Estate Investors

    MAY 14

    346: The 10 Best Books For Real Estate Investors

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a solo episode breaking down his 10 favorite books for real estate investors. Drawing from decades of experience as an investor and broker, along with insights gained through hosting the podcast, Jonathan explains how each book helped shape the way he thinks about money, investing, leverage, business building, and long-term wealth creation. Jonathan walks through a wide range of books covering topics like mindset, passive investing, syndications, wholesaling, long-distance investing, and financial psychology. Rather than focusing only on tactics, he highlights the importance of patience, discipline, and developing a long-term perspective when building a real estate business.  The episode also explores how different books can impact investors at different stages of their journey. Jonathan reflects on how books like Rich Dad Poor Dad, The Wealthy Gardener, and The Hands-Off Investor influenced his own investing philosophy and helped him better understand topics like leverage, operator quality, and asset ownership.  Throughout the episode, Jonathan encourages listeners to continually invest in education and build communities around learning. From creating book clubs to discussing strategies with other investors, he emphasizes that reading and ongoing learning are essential tools for long-term success in real estate investing.  In this episode, you will hear: • Jonathan's top book recommendations for real estate investors at every stage  • Why mindset and long-term thinking are critical for building wealth  • How books like Rich Dad Poor Dad and The Hands-Off Investor shaped his investing approach  • What investors should understand about leverage, syndications, and passive investing  • Why reading and ongoing education can create a long-term advantage in real estate  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 the show and supports its continued growth. Supporting Resources Connect with Jonathan: Amazon Affiliate Book List - https://a.co/d/0cEtkDWN  Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.

    44 min
  5. 345: Owning, Improving, and Building Manufactured Homes with Amanda Cruise

    MAY 11

    345: Owning, Improving, and Building Manufactured Homes with Amanda Cruise

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Amanda Cruise, founder of Voyage Investing, who shares how she built a business focused on manufactured housing and mobile home parks. Amanda walks through her journey from the corporate world into real estate, starting with a duplex before discovering the scalability and opportunity within mobile home investing. Amanda explains how she transitioned from small "Lonnie deals" into owning mobile home parks, highlighting why the asset class offers strong cash flow and demand due to its role in affordable housing. She also breaks down the realities of the space, including the operational complexity, management challenges, and why it's not as passive as many investors assume. The conversation explores how mobile home park investing has evolved, with increased competition from private equity and investors shifting from multifamily into the space. Amanda shares how to evaluate deals today, including the importance of understanding infrastructure, market growth, and realistic business plans rather than relying on outdated strategies or overly optimistic projections. Jonathan and Amanda also discuss the differences between active and passive investing, emphasizing that while mobile home parks can be powerful investments, they require the right operator and thorough due diligence. They highlight the risks of chasing high returns without understanding the underlying deal and why investor education is critical in today's market. In this episode, you will hear: • How Amanda Cruise got started in real estate and transitioned into mobile home parks • Why mobile home parks can generate strong cash flow but require active management • How the asset class has become more competitive with private equity entering the space • What investors need to understand about infrastructure, market selection, and deal evaluation • The difference between active and passive investing and how to choose the right approach 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 the show and supports its continued growth.   Supporting Resources Connect with Amanda Website: https://voyageinvesting.com/  LinkedIn: https://www.linkedin.com/in/amandacruisemhpinvestor/  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.

    54 min
  6. 344: How To Talk To Your Kids About Real Estate Investing

    MAY 7

    344: How To Talk To Your Kids About Real Estate Investing

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a solo episode focused on how to talk to your kids about real estate investing and financial literacy. Drawing from his own upbringing, he explains how early exposure to conversations about money, investing, and ownership shaped his understanding of wealth and opportunity.  Jonathan reflects on how simple, everyday moments—like car rides, errands, and vacations—became opportunities to learn about real estate. He emphasizes that today's parents face more distractions competing for their kids' attention, but the same lessons can still be taught by making real estate and money an open, ongoing conversation.  The episode explores why real estate is such a powerful teaching tool, given its visibility and relevance in everyday life. From understanding who owns buildings to learning about rent, mortgages, and leverage, Jonathan explains how these concepts can naturally lead into broader financial education.  He also highlights the importance of teaching kids about saving, investing, and making smart financial decisions through practical experiences like allowances, bank accounts, and even collectibles. By combining real-world exposure with simple explanations, parents can help their kids build a strong foundation for financial independence.  In this episode, you will hear: • Why real estate is one of the best ways to teach kids about money  • How everyday activities can become opportunities for financial education  • The importance of teaching saving, investing, and budgeting early  • How to explain concepts like rent, mortgages, and ownership in simple terms  • Why open conversations about money can give kids a long-term advantage  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 the show and supports its continued growth.   Supporting Resources Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.

    34 min
  7. 343: Learning How To Launch Short-Term Rentals with Nico Molino

    MAY 4

    343: Learning How To Launch Short-Term Rentals with Nico Molino

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Nico Molino, co-founder of Live in Luxury, who shares how he transitioned from tech sales into building a high-end short-term rental business. Nico explains how a unique opportunity, a renovated 110-year-old Piggly Wiggly grocery store, became the foundation for a scalable STR portfolio.  Nico walks through how he identified the property's potential, redesigned it into a standout Airbnb experience, and ultimately increased revenue by converting it from two smaller units into one large, high-demand rental. He highlights how differentiation, storytelling, and amenities play a critical role in standing out in today's competitive STR market.  The conversation also explores Nico's shift into mid-term rentals, where he and his team leveraged corporate housing strategies to build predictable income streams. From there, he expanded into helping investors launch short-term rentals using a data-driven approach that balances tax benefits with long-term profitability.  Jonathan and Nico emphasize that short-term rentals should be treated like a true business, not passive income. They discuss the importance of strong operations, professional design, and understanding your market to maximize returns and avoid costly mistakes.  In this episode, you will hear: • How Nico turned a historic Piggly Wiggly into a high-performing short-term rental  • Why larger, unique properties can outperform standard rentals  • The role of amenities and design in driving higher nightly rates  • How mid-term rentals can provide stable, lower-maintenance income  • Why short-term rentals should be treated like a business, not passive income  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 the show and supports its continued growth.   Supporting Resources Connect with Nico Website: https://liveinluxury.co/  Instagram: https://www.instagram.com/nico.molino4/  LinkedIn: https://www.linkedin.com/in/nico-molino-b5271960/  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com This episode was produced by Outlier Audio.

    54 min
  8. 342: How To Run a Cost-Conscious Short-Term Rental with Julie Thomas

    APR 30

    342: How To Run a Cost-Conscious Short-Term Rental with Julie Thomas

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Julie Thomas, founder of The STR Edit and The STR Visionary, who shares how she built a successful short-term rental business starting with a $20,000 budget. Julie walks through her journey from being a teacher to becoming an experienced investor and designer, helping others create high-performing STR properties without overspending. Julie explains how her first investment in West Yellowstone came from poor guest experiences and a desire to do better. She and her husband took a hands-on approach, sourcing furniture creatively, prioritizing key amenities, and focusing on guest experience to dramatically increase revenue and reviews. The conversation also highlights the biggest misconceptions about short-term rentals, including the idea that they require massive design budgets or operate as passive income. Julie emphasizes the importance of understanding your market, knowing your guest avatar, and balancing both design and operations to create a successful property. Jonathan and Julie also discuss practical strategies like setting a strict budget, avoiding unnecessary upgrades, and learning from real guest feedback. They stress that strong operations, responsiveness, and attention to detail are just as important as aesthetics when it comes to earning five-star reviews and repeat bookings. In this episode, you will hear: How Julie Thomas got started in short-term rentals with a $20K budget Why most STRs don't require massive design budgets to succeed The biggest mistakes new investors make when getting started How to balance design and operations to improve guest experience Why knowing your market and guest avatar is critical to 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 the show and supports its continued growth.   Supporting Resources Connect with Julie: Website: https://www.stredit.com/  LinkedIn: https://www.linkedin.com/in/strvisionary/  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com Brokerage - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/zenrealestateinvesting Instagram-  www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties Instagram - www.instagream.com/zenupstate Zillow - www.zillow.com/profile/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Email - Jonathan@trustgreene.com 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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