Zen and the Art of Real Estate Investing

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. 6d ago

    374: How to Know When to Keep, Refinance, or Sell a Rental Property with Chris Lopez

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Chris Lopez, co-founder of Property Llama, real estate investor, entrepreneur, and host of the Passive Pockets and Denver Investment Real Estate podcasts, to talk about building, managing, and rebalancing a real estate portfolio. Chris shares how reading Rich Dad Poor Dad in college introduced him to entrepreneurship and investing, eventually leading him from internet businesses and unsuccessful attempts at day trading into real estate. He explains how he bought his first rental property in 2011 with zero money down, lived in it for a period of time, and initially assumed he would hold it forever. The conversation then explores the important lesson Chris learned about using equity. After watching his first property grow from roughly $67,000 to nearly $200,000 while producing only modest cash flow, Chris realized he needed to think differently about the capital trapped inside his portfolio. He ultimately used a 1031 exchange to move that equity into a fourplex and dramatically increase his cash flow. Chris explains why he began treating his real estate portfolio like an investment portfolio that needs to be regularly rebalanced. He walks through his keep, refinance, or sell framework and explains how changing markets, family circumstances, risk tolerance, and available returns can all change whether a property still makes sense to own. He also discusses how this thinking led to the creation of Property Llama, a platform designed to help investors analyze their properties and make better portfolio decisions. Finally, Chris and Jonathan discuss return on equity, passive investing, syndications, debt funds, diversification, and the importance of taking responsibility for your investment decisions. Chris explains why he has increasingly shifted toward passive investments and real estate debt, and why investors should focus on building a portfolio that fits their current life rather than simply accumulating as many properties as possible. In this episode, you will hear: How Chris went from reading Rich Dad Poor Dad in college to becoming an entrepreneur and real estate investor Why Chris sold his first rental property and used a 1031 exchange to redeploy its equity into a fourplex How the keep, refinance, or sell framework can help investors regularly rebalance their real estate portfolios Why return on equity, opportunity cost, and changing life circumstances should influence your investment decisions How Chris's experience led to Property Llama and his growing focus on passive investing, syndications, and real estate debt 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 Chris: Website - http://propertyllama.com/  YouTube - https://www.youtube.com/@BuildingWealthWithRealEstate  LinkedIn - https://www.linkedin.com/in/christaylorlopez/  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    374: How to Know When to Keep, Refinance, or Sell a Rental Property with Chris Lopez
  2. Sep 23

    373: How to Build Financial Freedom on Your Days Off with Mike Neubauer

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Mike Neubauer, a retired Maui firefighter, photographer, real estate investor, and co-founder of Our Family Invests, to talk about building financial freedom through real estate, intentional investing, and creating a lifestyle that puts family and purpose first. Mike shares how his creative background and experience as a firefighter shaped his approach to entrepreneurship and investing. He explains how the time and flexibility of working in the fire department gave him the opportunity to read, research, and develop himself, eventually leading him to real estate through a fellow firefighter who was already investing in Maui. The conversation explores Mike's evolution from short-term rentals to a more passive investment strategy. He explains how he created an extremely specific buy box for Maui properties, why he focused on condo complexes with lockout units, and how he went from remodeling his first short-term rental himself to building a portfolio that generated significant income. Mike also discusses how the Maui market changed dramatically after 2023, including rising insurance and HOA costs, declining tourism, and regulatory changes surrounding short-term rentals. He shares why he ultimately sold many of his Maui properties and shifted his investments toward other markets, including development projects in Utah and Idaho. Finally, Mike and Jonathan dig into lifestyle investing, family wealth, syndications, and the importance of taking ownership of your investment decisions. Mike explains why he prefers betting on the operator rather than simply the asset class, how syndications have given him exposure to markets and investments without the operational headaches, and why understanding your current financial position and your family's goals should come before deciding what to invest in. In this episode, you will hear: How Mike used his firefighter schedule to pursue personal development and discover real estate investing Why Mike created a highly specific buy box for short-term rental properties in Maui How changing tourism, insurance costs, HOA fees, and regulations transformed the Maui short-term rental market Why Mike shifted from active real estate investing toward syndications, development, and lifestyle-focused investments How family goals, financial awareness, and extreme ownership can lead to better long-term investment decisions 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 Mike: Website - OurFamilyInvests.com YouTube - Youtube.com/@OurFamilyInvests  Facebook - Facebook.com/OurFamilyInvests  Instagram - Instragram.com/OurFamilyInvests  LinkedIn - https://www.linkedin.com/in/mikeyneu/  TikTok - TikTok.com/OurFamilyInvests  Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    373: How to Build Financial Freedom on Your Days Off with Mike Neubauer
  3. Sep 16

    372: The Passive Income Lie Nobody in Real Estate Wants to Admit

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene breaks down the truth behind passive income in real estate and why the word "passive" is often used far too loosely. He explains why passive income is better understood as a spectrum, with different investments requiring different levels of involvement, oversight, and management. Jonathan walks through where different real estate strategies fall on that spectrum, from syndications and REITs to long-term rentals, short-term rentals, multifamily properties, and house flipping. He explains why property management can make an investment less active without necessarily making it truly passive, and why owning a rental property still requires you to make decisions when things inevitably go wrong. The episode also explores the hidden labor behind supposedly passive investments, including tenant issues, vacancies, capital expenditures, management oversight, and unexpected repairs. Jonathan explains why investors need to understand the true operational demands of an asset before deciding whether the returns justify the amount of work involved. Jonathan also discusses the tradeoffs between control, trust, and return, including why giving up control was initially difficult when he began investing in syndications. He shares how becoming more comfortable with passive investing has allowed him to diversify his wealth while spending less time managing individual properties. Finally, Jonathan explains that the real benefit of passive income isn't simply making more money. It's optionality. The ability to create time freedom and choose what you want to do with your life instead of being tied to the day-to-day operations of an investment. In this episode, you will hear: Why passive income is a spectrum rather than a simple yes-or-no category Where syndications, REITs, rentals, short-term rentals, multifamily, and house flipping fall on the active-to-passive spectrum Why property management makes an investment less active but does not necessarily make it passive The hidden labor, costs, and decision-making that come with owning rental properties Why the real value of passive income is optionality and time freedom, not simply more money 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 YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    372: The Passive Income Lie Nobody in Real Estate Wants to Admit
  4. Sep 9

    371: What Passive Income Actually Buys You When the Business Stops with Rachel Richards

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Rachel Richards, bestselling author of Money Honey and Passive Income Aggressive Retirement, to talk about building financial independence, investing in real estate, and redefining what retirement really means. Rachel shares how growing up in a household that struggled financially shaped her relationship with money and motivated her to become financially independent at a young age. She explains how she went from earning a modest salary to buying her first duplex at 24, building a portfolio of boarding houses, and eventually reaching financial independence at 27. The conversation also explores Rachel's experience with the FIRE movement, including why she believes extreme frugality can be useful at certain stages but can eventually become counterproductive. She and Jonathan discuss the difference between financial independence and time freedom, and why having something meaningful to retire to can be just as important as having enough money to retire. Rachel also opens up about walking away from the successful social media business she built after realizing it had become a source of burnout rather than fulfillment. She shares what she learned about identity, external validation, and finding purpose after stepping away from a business that had become a major part of her life. Finally, Rachel and Jonathan discuss financial education, relationships, prenups, investing with a partner, and why building a stable income before pursuing entrepreneurship can give you the freedom to take smarter risks. In this episode, you will hear: How growing up with financial stress shaped Rachel's approach to money and motivated her to become financially independent How Rachel bought her first duplex at 24 and eventually built a portfolio of boarding houses and rental properties Why Rachel believes extreme frugality can help you build wealth but can become harmful when you no longer need it What Rachel learned about retirement, identity, and fulfillment after stepping away from her social media business Why financial education, stable income, prenups, and open conversations about money are critical to building a stronger financial future 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 Rachel: Website - www.moneyhoneyrachel.com  Instagram - @moneyhoneyrachel TikTok - @moneyhoneyrachel Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    371: What Passive Income Actually Buys You When the Business Stops with Rachel Richards
  5. Sep 2

    370: Why Wealth and Financial Freedom Are Different For Each Person

    On this solo episode of Zen and the Art of Real Estate Investing, Jonathan Greene explores why wealth, financial freedom, and time freedom mean something different for every person. He explains why there is no universal number that defines financial freedom and how factors like where you live, how you were raised, your lifestyle, your family, and your personal goals all shape what enough looks like. Jonathan breaks down the difference between being rich, being wealthy, and being financially free, emphasizing that someone can achieve financial freedom without being wealthy and that accumulating income does not necessarily create lasting wealth. He also examines how family history and early experiences with money can influence the way people think about saving, spending, risk, and building wealth. The episode also looks at the true cost of financial independence. Jonathan discusses how housing costs, lifestyle choices, family responsibilities, taxes, healthcare, and spending habits can dramatically change the amount of money someone needs to feel financially secure. He explains why increasing your income and acquiring assets that generate income over time can be more powerful than simply cutting expenses. Jonathan also challenges the popular FIRE movement and the idea that everyone should aim to retire as early as possible. He argues that financial freedom and time freedom are not necessarily the same thing, especially because many people actually enjoy working, building businesses, having structure, and staying productive. Instead of copying someone else's definition of freedom, he encourages listeners to determine what enough means for them. Finally, Jonathan discusses comparison, FOMO, compound interest, and the importance of creating financial habits that work for your own life. He explains why comparing your financial journey to someone else's can lead you away from your own goals and why building wealth requires saving, putting money to work, and thinking long-term. In this episode, you will hear: Why wealth, financial freedom, and time freedom are different concepts How your location, lifestyle, family, and upbringing shape your financial goals Why Jonathan challenges the FIRE movement and the idea of retiring extremely early How defining what "enough" means can change the way you approach wealth building Why saving, compound interest, reducing comparison, and creating financial mindfulness are essential to building lasting wealth 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 YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    370: Why Wealth and Financial Freedom Are Different For Each Person
  6. Aug 26

    369: Why the Best Real Estate Investors Know When to Stop and Start Again with Ian Slater

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Ian Slater, founder and partner at Trove Partners, a discreet real estate advisory team specializing in high-net-worth clients in New York, the Hamptons, and worldwide. Ian shares how growing up around his father's construction business shaped his understanding of real estate, even though he never expected to make it his career, and how he eventually built a successful career serving luxury real estate clients in New York. Jonathan and Ian discuss what separates the most successful real estate brokers from everyone else, including the importance of trust, organization, follow-through, relationships, and understanding the lifestyle of high-net-worth clients. Ian explains how he intentionally built his personal brand and network in his 20s by putting himself in the right rooms and developing the ability to connect with sophisticated clients. The conversation also explores Ian's personal real estate investing journey. He and his husband started with a $255,000 multifamily property in Providence, Rhode Island, eventually building a portfolio of roughly 40 apartments across eight buildings. Ian explains how they used renovation, refinancing, appreciation, and time to build equity, and how their strategy evolved from managing multifamily properties to renovating and selling homes and pursuing development opportunities. Jonathan and Ian also examine how the current real estate market differs from the environment that allowed them to get started, including higher interest rates, compressed cap rates, rising property values, and the opportunity cost of investing in real estate versus other assets. They discuss why sophisticated investors need to understand the market they're operating in, why some New York properties still command a premium, and how Ian's investing experience helps him give clients honest advice about whether real estate actually makes sense for their goals. Finally, Jonathan and Ian discuss the future of real estate, AI, wealth building, and the importance of playing the long game. Ian explains why he believes high-level real estate brokerage remains a relationship-driven business that is difficult to replace with technology, why avoiding "commission breath" builds trust, and how he hopes to eventually build a portfolio that produces meaningful cash flow and financial flexibility without necessarily focusing on passing a real estate empire to future generations. In this episode, you will hear: How Ian went from growing up around construction to becoming a luxury real estate advisor Why trust, follow-through, and relationship building are essential to succeeding in high-end real estate How Ian and his husband built a 40-unit Providence real estate portfolio Why market conditions today require investors to think differently than they did a decade ago How to build long-term wealth through real estate while staying flexible enough to adapt as your goals and the market change 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 Ian: Website - https://www.trove-partners.com/  Instagram - https://www.instagram.com/ianslater/  LinkedIn - https://www.linkedin.com/in/ian-slater-53688124 Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    369: Why the Best Real Estate Investors Know When to Stop and Start Again with Ian Slater
  7. Aug 19

    368: Why Owning a Franchise Is the Other Path to Financial Freedom with Cliff Nonnenmacher

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Cliff Nonnenmacher, CEO and founder of Franocity, author, and franchise consultant, to explore franchising, entrepreneurship, and building businesses that can create lasting wealth. Cliff shares his unconventional path from collecting golf balls as a kid to investment banking, trading, owning multiple businesses, and eventually becoming deeply involved in franchising. Jonathan and Cliff dive into what makes a franchise a strong investment, why following a proven playbook can be more valuable than trying to reinvent the wheel, and how prospective franchise owners should evaluate their own skills, goals, risk tolerance, and willingness to execute. They also discuss why time freedom is often a bigger motivator than money and how entrepreneurs can build businesses with generational wealth and legacy in mind. The conversation also looks at the impact of AI and automation on the future of business. Cliff explains why entrepreneurs should focus on industries that are further from technological disruption, including businesses requiring hand dexterity, services for an aging population, youth enrichment, the humanization of pets, and the pursuit of health and longevity. Jonathan and Cliff also explore the challenges of generational succession and why so many business owners discover too late that their children have no interest in taking over the family business. They discuss the importance of exit planning, how franchise owners can grow through acquisitions, and why aging mom and pop businesses may represent significant opportunities for entrepreneurs who already have a proven system in place. Ultimately, this episode is about building something that gives you more than an income. Jonathan and Cliff discuss creating time freedom, following proven systems, adapting to disruption, planning for succession, and making sure the life's work you build can actually become an asset that someone else wants to buy. In this episode, you will hear: How Cliff went from childhood entrepreneurship to franchising Why time freedom is often more important than financial freedom What makes someone a strong candidate for franchise ownership How AI and automation could reshape traditional businesses Why business owners need to plan their exit before they are ready to leave 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 Cliff: Website - https://franocity.com  YouTube - https://www.youtube.com/@Franocity  Facebook - http://www.facebook.com/franocity  LinkedIn - www.linkedin.com/in/cliffnonnenmacher  X - http://x.com/franocity Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    368: Why Owning a Franchise Is the Other Path to Financial Freedom with Cliff Nonnenmacher
  8. Aug 12

    367: Why Reverse Mortgages Are the Best Kept Secret in Retirement Planning with Cheryl Scheidell

    On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Cheryl Scheidell, a reverse mortgage specialist with Barrett Financial Group, for an in-depth conversation about one of the most misunderstood financial tools available to homeowners. Cheryl explains how reverse mortgages have evolved over the years, who they are designed to help, and why they can play an important role in retirement planning, wealth preservation, and helping seniors age in place with greater financial security. Jonathan and Cheryl break down exactly how reverse mortgages work, separating common misconceptions from reality. Cheryl explains why borrowers are no longer required to make monthly mortgage payments, how equity is accessed responsibly, and why modern safeguards, including HUD counseling, have made today's Home Equity Conversion Mortgage (HECM) program much different from the products that earned a negative reputation years ago. They also discuss how reverse mortgages can be used to purchase homes, refinance existing loans, or even preserve low-interest first mortgages through second-position products. The conversation also explores the importance of family communication around financial planning. Jonathan and Cheryl discuss why adult children should be included in these conversations, how reverse mortgages can reduce the financial burden on families caring for aging parents, and why proactive estate planning often prevents unnecessary conflict later. They also explain how reverse mortgages can help pay for home modifications, in-home care, assisted living expenses, or simply allow retirees to enjoy the wealth they have spent decades building. Ultimately, this episode highlights the value of education over assumptions. Rather than viewing reverse mortgages as a last resort, Jonathan and Cheryl encourage listeners to understand them as one potential financial planning tool that, when used appropriately, can improve cash flow, preserve retirement assets, and create greater peace of mind for both homeowners and their families. In this episode, you will hear: How reverse mortgages work and why today's programs differ from outdated perceptions Why reverse mortgages can improve cash flow while allowing seniors to remain in their homes How reverse mortgages can help fund home modifications, healthcare, and retirement expenses Why involving adult children in financial planning conversations benefits the entire family How Home Equity Conversion Mortgages (HECMs) include consumer protections and required counseling Why reverse mortgages can serve as a valuable wealth preservation and retirement planning tool when used appropriately 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 Cheryl: Website - reversemortgageandbeyond.com  YouTube - @reversemortgageandbeyond  Facebook - https://www.facebook.com/ReverseMortgageLoanOfficer/  Instagram - reversemortgageandbeyond  LinkedIn - linkedin.com/in/cherylscheidell  Email - cheryls@barrettfinancial.com  Cell - (480) 817-4324 Connect with Jonathan: Podcast - www.zenandtheartofrealestateinvesting.com YouTube - www.youtube.com/JonathanGreenere Instagram - www.instagram.com/zenrealestateinvesting Instagram - www.instagram.com/trustgreene Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/zenandtheartofrealestateinvesting Jonathan's Hub Site - www.trustgreene.com Brokerage - https://www.streamlined.properties This episode was produced by Outlier Audio.

    367: Why Reverse Mortgages Are the Best Kept Secret in Retirement Planning with Cheryl Scheidell
4.9
out of 5
110 Ratings

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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