Zen and the Art of Real Estate Investing

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

376: The Difference Between an Asset Hunter and a Discount Hound Oct 14, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene explores two very different approaches to real estate investing: being an asset hunter versus being a discount hound. He explains why prioritizing the quality and long-term potential of a property can matter far more than simply getting it below market value.

Jonathan breaks down what asset hunters look for, including appreciation potential, cash flow, location, and the overall condition of a property. He contrasts that mindset with discount hunters who focus primarily on the purchase price, often overlooking the hidden costs, deferred maintenance, difficult tenants, and other problems that can come with a seemingly attractive deal.

The conversation examines why the best properties don't always look like bargains on paper. Jonathan explains how paying a fair market price for a high-quality asset can support long-term appreciation, reduce future capital expenses, and make ownership more manageable. He also discusses why investors need to understand the trade-offs between cash flow, property condition, location, and risk rather than chasing impressive-looking returns without understanding what supports them.

Jonathan shares practical ways to evaluate an investment beyond its asking price, emphasizing thorough due diligence, inspections, comparable sales, local demographics, migration trends, and growth potential. He also explains why investors should be comfortable walking away when a property doesn't meet their standards, even if someone else is willing to pay more.

Finally, Jonathan reflects on the difference between a calculated deal hunter and someone who simply wants a discount. Drawing on lessons from his father and his own investing experience, he makes the case for understanding your risk tolerance, knowing what you're buying, and focusing on assets that can compound in value over time.

In this episode, you will hear:

The key differences between an asset hunter and a discount hound
Why a discounted property isn't necessarily a good investment
How property quality, location, and condition can affect long-term returns and ownership costs
What investors should examine during due diligence before getting caught up in a seller's story about a deal
Why the ability to walk away and stay disciplined about your valuation is essential to successful investing

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Supporting Resources

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

375: What Holistic Wealth Means and Why Most Investors Never Get There with Wesley Rowlands Oct 07, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Wesley Rowlands, partner and wealth advisor at Atican Wealth Partners, to explore what wealth really means, how people can build it, and why financial success should be measured by more than the number in your bank account.

Wesley explains the difference between financial wealth and holistic wealth, emphasizing the importance of understanding what money is supposed to accomplish in your life. He shares his framework of philosophy, strategy, and tactics, and explains why investors need to establish their vision, values, and desired lifestyle before deciding how to invest. He also breaks down the wealth-building formula of making money, saving money, and growing money, noting that increasing income is often the first major obstacle.

The conversation explores Wesley's journey from growing up with financial hardship to developing an early interest in investing and building a career in wealth management. He discusses why he believes building wealth requires financial leadership rather than passivity, the value of having experienced coaches and advisors, and how psychology can influence financial decisions. He also explains the difference between volatility and risk, and why investors need to look beyond headlines and emotional reactions.

Wesley shares his approach to building a portfolio around short-term, medium-term, and long-term assets. He discusses why he favors productive assets that generate value and cash flow, including public companies, private businesses, and real estate. He and Jonathan also examine business ownership, the opportunities in acquiring established businesses, the role of AI, and why building a valuable business requires sustained effort and a commitment to excellence.

Finally, Wesley explains how business ownership can become a powerful form of personal development, why disciplined execution of the fundamentals matters more than shortcuts, and how the right coaches can help investors make better decisions over time. Throughout the conversation, he returns to the idea that wealth should support a meaningful life, not become the end goal itself.

In this episode, you will hear:

Why wealth should be defined by the life you want to build, not simply the amount of money you accumulate
How Wesley's early experiences with financial hardship shaped his path into investing and wealth management
Why making money, saving money, and growing money are all essential parts of building wealth
How Wesley evaluates productive assets, including public companies, private businesses, and real estate
Why financial leadership, experienced coaches, and disciplined execution can help investors make better long-term decisions

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Supporting Resources

Connect with Wesley:

Website - https://www.atikanwealth.com/

YouTube - youtube.com/@WesRowlands

Facebook - facebook.com/wesrowlandsofficial

Instagram - https://www.instagram.com/wes.rowlands/

LinkedIn - https://www.linkedin.com/in/wesrowlands/

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

374: How to Know When to Keep, Refinance, or Sell a Rental Property with Chris Lopez Sep 30, 2026

Show notes

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

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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

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

373: How to Build Financial Freedom on Your Days Off with Mike Neubauer Sep 23, 2026

Show notes

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

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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

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

372: The Passive Income Lie Nobody in Real Estate Wants to Admit Sep 16, 2026

Show notes

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

Supporting Resources

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

371: What Passive Income Actually Buys You When the Business Stops with Rachel Richards Sep 09, 2026

Show notes

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

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Supporting Resources

Connect with Rachel:

Website - www.moneyhoneyrachel.com

Instagram - @moneyhoneyrachel

TikTok - @moneyhoneyrachel

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

370: Why Wealth and Financial Freedom Are Different For Each Person Sep 02, 2026

Show notes

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

Supporting Resources

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

This episode was produced by Outlier Audio.

369: Why the Best Real Estate Investors Know When to Stop and Start Again with Ian Slater Aug 26, 2026

Show notes

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

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

Instagram - www.instagram.com/zenrealestateinvesting

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com