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. 332: How To Make Sure You Are Ready To Invest in Real Estate

    12H AGO

    332: How To Make Sure You Are Ready To Invest in Real Estate

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene breaks down what it actually means to be ready to invest in real estate and why so many investors sabotage themselves right after getting an offer accepted. He shares his frustration with a growing pattern of buyers who do the work to win deals, only to panic, second-guess, and ultimately walk away from strong opportunities. Jonathan explains that readiness goes far beyond getting pre-approved. While having finances in order, reserves set aside, and a clear understanding of costs is critical, the real differentiator is confidence. He emphasizes the importance of trusting your team, including your agent and lender, and warns that constantly seeking validation from friends, family, or AI tools signals a lack of readiness that can derail deals. The conversation also explores the emotional side of investing. Jonathan highlights how fear, outside opinions, and overanalysis can lead to meltdowns that waste time for everyone involved and damage relationships. He encourages investors to be honest with themselves about whether they are truly prepared to move forward or just testing the waters without commitment. Ultimately, this episode is about personal accountability. Jonathan challenges listeners to evaluate their mindset, build a trusted team, and develop the confidence needed to follow through. For those who are ready, real estate can be a powerful wealth-building tool—but only if they are willing to act decisively and trust the process. In this episode, you will hear: Why getting pre-approved is only one piece of being truly ready to invest The role confidence plays in successfully closing real estate deals How relying on the wrong voices can derail otherwise strong opportunities Why trust in your agent and lender is essential to moving forward The importance of having reserves and understanding total costs How to recognize whether you are actually ready or just "getting ready to get ready" 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.   Connect with Jonathan: Website: www.streamlined.properties  Website: https://www.trustgreene.com/  YouTube:  https://www.youtube.com/jonathangreenere  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.

    36 min
  2. 331: Short-Term Rental Safety, Risk Management, and Fire Prevention with Justin Ford

    3D AGO

    331: Short-Term Rental Safety, Risk Management, and Fire Prevention with Justin Ford

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Justin Ford, director of safety and certification programs at Breezeway and a leading expert in short-term rental safety. Justin shares how a life-altering incident in one of his own properties led him to focus full-time on improving safety standards across the industry. Justin explains that the biggest risks in short-term rentals are often overlooked, with slips, trips, and falls making up the majority of incidents—not fires or other dramatic events. He highlights how common amenities like hot tubs, bunk beds, decks, and fire pits can create serious liability if not properly managed, and emphasizes that most properties fall short of even basic safety standards. Through real-world examples, Justin shows how small oversights can lead to major consequences for both guests and operators. The conversation also explores how prioritizing safety can become a competitive advantage. Properties that clearly communicate safety measures tend to attract higher-quality guests, reduce liability, and perform better over the long term. Justin introduces the concept of proactive safety systems, including checklists, documentation, and inspections, as essential tools for professional operators. For investors, this episode reinforces that safety is not just a compliance issue but a strategic one. By implementing proper systems and thinking like a first-time guest, operators can protect their investment, improve the guest experience, and future-proof their business against increasing regulation. In this episode, you will hear: Why slips, trips, and falls are the most common short-term rental injuries How one safety incident reshaped Justin's entire career The hidden risks behind popular amenities like hot tubs and bunk beds How safety-focused properties attract better guests and fewer issues Why documentation and checklists can protect you in lawsuits How to evaluate your property through the lens of a first-time guest 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. This episode was produced by Outlier Audio.   Supporting Resources Connect with Justin Website: http://breezeway.io/  Youtube: https://www.youtube.com/@breezewayio  Facebook: https://www.facebook.com/shorttermrentalsafety/  Instagram: https://www.instagram.com/shorttermrentalsafety  LinkedIn: https://www.linkedin.com/in/rentalsafety/  Promo code of 50ZEN for the safety course - https://breezeway.learnworlds.com/ Guide for buying an STR - https://www.breezeway.io/blog/before-you-buy-an-airbnb-property Connect with Jonathan: Website: www.streamlined.properties  Website: https://www.trustgreene.com/  YouTube:  https://www.youtube.com/jonathangreenere  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.

    57 min
  3. 330: The Case For Starting as a Passive Investor

    MAR 19

    330: The Case For Starting as a Passive Investor

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene makes the case for why many investors may want to start their real estate journey as passive investors rather than jumping directly into active ownership. Drawing from decades of experience as an active investor and landlord, Jonathan explains how his perspective has evolved and why he now prefers the simplicity and learning opportunities that come with being a limited partner in real estate syndications. Jonathan breaks down the differences between active and passive investing, explaining how passive investments allow investors to participate in large real estate deals without taking on the operational responsibilities of ownership. He shares examples from his own portfolio, including several multifamily syndications and a wellness hotel development, and describes how evaluating operators, assets, and markets has shaped his investment decisions. The conversation also highlights the hidden realities of active real estate investing. Jonathan discusses the operational headaches of flipping houses, managing tenants, and running short-term rentals, emphasizing that many investors underestimate the time, stress, and experience required to succeed in those strategies. For investors with deployable capital but limited time, Jonathan argues that passive investing can offer a powerful alternative. By partnering with experienced operators and investing in carefully selected assets, investors can still benefit from real estate's long-term growth and income potential while focusing their time and energy on their careers, families, and other priorities. In this episode, you will hear: Why Jonathan shifted from active real estate investing to passive syndications The key differences between passive and active real estate investments How to evaluate operators, assets, and markets before investing in a syndication Why spreadsheets and projections can be misleading for new investors The risks and benefits of investing as a limited partner in real estate deals Why passive investing may be a better starting point for busy professionals 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. This episode was produced by Outlier Audio.   Supporting Resources Connect with Jonathan: Website: www.streamlined.properties  Website: https://www.trustgreene.com/  YouTube:  https://www.youtube.com/jonathangreenere  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.

    39 min
  4. 329: The Benefits of Owning Multiple Real Estate Businesses with James Faillettaz

    MAR 16

    329: The Benefits of Owning Multiple Real Estate Businesses with James Faillettaz

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews James Faillettaz, founder and CEO of Verus Praedium Holding. James oversees multiple real estate businesses, including brokerage, property management, acquisitions, and leasing, and shares how building an interconnected platform has helped him grow his portfolio and create opportunities across different parts of the industry. Jonathan and James explore the operational realities of running several real estate businesses at once and why property management is often the most challenging part of the business. James explains how managing subsidized housing and diverse tenant situations requires empathy, adaptability, and strong systems. They also discuss how organizational structure and long-term planning help companies scale without constantly rebuilding their internal processes. The conversation also dives into the culture of multifamily properties and how small operational issues can quickly compound if they are not addressed. James shares how the "broken window theory" applies to property management and why maintaining standards across buildings is essential as a portfolio grows. The discussion highlights how leadership, consistency, and attention to detail can dramatically change the environment and performance of a property. In this episode, you will hear: Why property management is often the hardest part of running a real estate business How owning multiple real estate businesses can create operational advantages The importance of planning a company structure with long-term growth in mind How building culture can improve the performance of multifamily properties Lessons from scaling a portfolio while maintaining operational standards Why small operational problems can compound if they are ignored 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 James Website: https://revolutionrealtymn.com/  Facebook: https://www.facebook.com/p/Revolution-Realty-Group-61574230950443/  Instagram: https://www.instagram.com/revolutionrealtygroupmn/  Connect with Jonathan: Website: www.streamlined.properties  Website: https://www.trustgreene.com/  YouTube:  https://www.youtube.com/jonathangreenere  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
  5. 328: What You Need To Know About Commercial Mortgage-Backed Securities with Michael Cohen

    MAR 12

    328: What You Need To Know About Commercial Mortgage-Backed Securities with Michael Cohen

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Michael Cohen, founder and managing partner of Brighton Capital Advisors. With more than 25 years of experience in commercial real estate lending, debt sourcing, restructuring, and advisory work, Michael shares what he is seeing from the front lines of the current commercial real estate cycle. Jonathan and Michael discuss the shift from the value-correction phase to what Michael calls the "asset transfer phase," in which lenders are increasingly moving toward foreclosures, note sales, and restructurings as distressed loans work their way through the system. Michael explains why lenders were slower to act in prior years, how rising interest rates and operating costs have created pressure on multifamily and other assets, and why many borrowers are now facing critical decisions about whether to reinvest capital or exit their properties. The conversation also dives into the complexity of CMBS and CLO loan structures and why borrowers often underestimate lenders' leverage once loans are securitized. Michael shares how proactive communication, strong advisory teams, and a realistic understanding of loan documents can dramatically improve outcomes when navigating distressed situations. For investors, this episode highlights the importance of understanding leverage, capital reserves, and sponsor strength when evaluating real estate deals. Market cycles are inevitable, but preparation, knowledge, and disciplined decision-making can make the difference between surviving a downturn and losing an asset. In this episode, you will hear: Why commercial real estate is entering an asset transfer phase in the current cycle How rising rates and operating costs created pressure across multifamily assets Why lenders are becoming more aggressive with foreclosures and note sales The risks and complexities of CMBS and CLO loan structures Why capital reserves and sponsor strength matter during downturns How proactive communication can improve outcomes in distressed loan situations 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. This episode was produced by Outlier Audio.   Supporting Resources Connect with Michael: Website: https://brightoncapitaladvisors.com/  Facebook: https://www.facebook.com/brightoncapitaladvisors  LinkedIn: http://linkedin.com/company/brightoncapitaladvisors/  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.

    57 min
  6. 327: Unlocking Global Living Options and Plan B Potential with Ladislas Maurice

    MAR 9

    327: Unlocking Global Living Options and Plan B Potential with Ladislas Maurice

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Ladislas Maurice, international investor, consultant, and founder of The Wandering Investor. Ladislas has lived in more than a dozen countries and brings a global perspective to the conversation as he returns to the show to discuss how international investing and second citizenship strategies are evolving in a rapidly changing world. Jonathan and Ladislas explore the growing demand for Plan B strategies as investors and families look for residency, citizenship, or diversification outside their home countries. Ladislas explains the differences between residency and citizenship, how various immigration programs work, and why many investors are now thinking about global mobility not just for themselves but for future generations. The conversation also highlights emerging trends in international investing. Ladislas discusses countries currently attracting attention from global investors, including parts of Latin America and Africa, while explaining why some immigration programs become harder over time as demand increases. The episode offers listeners a framework for evaluating where they might want to live, invest, or create optionality in the future. For investors thinking long term, this episode reinforces the importance of understanding global opportunities and risks. Whether it is residency, citizenship, or international real estate investing, thoughtful planning can expand the number of choices available for you and your family in an uncertain world. In this episode, you will hear: Why more investors are pursuing a Plan B through residency or second citizenship The difference between residency, citizenship, and holding a second passport How global political and economic shifts are influencing international real estate investing Countries currently attracting attention for residency and investment opportunities Why immigration programs tend to become more restrictive over time How international diversification can create long-term options for future generations 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. This episode was produced by Outlier Audio.   Supporting Resources Connect with Ladislas: Website: https://thewanderinginvestor.com/  Youtube: https://www.youtube.com/channel/UC1EOqi1UVw2Byy8jc-glFMQ/  Facebook: https://facebook.com/thewanderinginvestor  Instagram: https://instagram.com/thewanderinginvestor  LinkedIn: https://www.linkedin.com/company/the-wandering-investor/  Twitter: https://twitter.com/wander_investor  Telegram: https://t.me/thewanderinginvestor  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.

    48 min
  7. 326: Turning Properties Into High-Performing Assets with Dan Rivers

    MAR 5

    326: Turning Properties Into High-Performing Assets with Dan Rivers

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Dan Rivers, co-founder of SynergyStays and founder of Rivers Capital Group. Dan shares how he built a diverse real estate background spanning property management, sales, flipping, private lending, and short-term rentals before narrowing his focus to revenue management for STR operators. He explains why trying to do everything at once held him back and how focusing on his strengths allowed him to grow more intentionally. Dan discusses the evolution of the short-term rental market, from the post-pandemic gold rush to today's more competitive, professionalized environment. He breaks down why many operators struggle when they treat STRs passively, and why success now requires attention to revenue management, guest experience, and consistent optimization. The conversation also explores house hacking, mindset shifts, and the power of showing up consistently in investor meetups to accelerate growth. If you're feeling scattered in your investing journey or unsure where to start, this episode offers clarity: focus on your superpower, surround yourself with the right people, and treat real estate like the business it is. In this episode, you will hear: Why focusing on one strength can unlock faster growth How the short-term rental landscape has shifted since 2020 The importance of revenue management in maximizing STR performance Why guest experience and reviews directly impact profitability How house hacking can accelerate wealth building The power of consistent networking and investor meetups 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 Dan: Website: http://www.synergystayslocal.com/  Youtube: SynergyStays  Facebook: Dan Rivers Instagram: @danrivers_RCG  Special Link for Zen guests: https://bit.ly/synergyzen 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.

    48 min
  8. 325: How To Reduce Vacancy Stress and Increase Profit as a Landlord with Oliver Lerner

    MAR 2

    325: How To Reduce Vacancy Stress and Increase Profit as a Landlord with Oliver Lerner

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Oliver Lerner, president and co-founder of Shuk Rentals, a property management software platform built specifically for mom-and-pop landlords. Oliver shares how he bought his first rental property while still in college by house hacking a five-bedroom home with friends, and how that early experience shaped the way he approaches both landlording and business today. Oliver walks through the steep learning curve of managing properties on your own. From plumbing mistakes to expensive HVAC lessons, he explains how those early challenges helped him develop confidence and practical skills. He talks about the importance of buying right, understanding your numbers, and being willing to walk away from deals when they do not make sense. The conversation also explores the realities of being a small landlord in today's environment. Oliver discusses local regulations, rising fees, and the responsibility that comes with providing housing. He explains why he created Shuk Rentals to bring more transparency and accountability into the rental process, while giving independent landlords better tools to manage leases, communication, and retention. At its core, this episode is about building experience through action and creating systems that support long-term ownership. In this episode, you will hear: • How Oliver house hacked his first rental property in college • Why seeing dozens of homes before buying builds confidence and discipline • The importance of buying right to protect yourself from costly mistakes • Lessons learned from self-managing rentals and solving problems firsthand • Why mom-and-pop landlords play a vital role in the housing market • How better systems and transparency can improve tenant retention 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. This episode was produced by Outlier Audio. Supporting Resources Connect with Oliver Website: http://www.shukrentals.com/  Facebook: https://www.facebook.com/shukrentals  Instagram: https://www.instagram.com/shukrentals  LinkedIn: https://www.linkedin.com/in/oliverlerner/  Twitter: https://x.com/ShukRentals  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.

    57 min
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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.

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