Zen and the Art of Real Estate Investing

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.

352: How To Get More Deals to the Closing Table with Henry Washington Jun 04, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene welcomes back Henry Washington for a conversation about what it really takes to succeed in changing market conditions. Henry shares why he's never focused on headlines, interest rates, or market predictions—instead relying on disciplined underwriting, risk management, and buying properties with enough margin to withstand changing conditions.

Henry explains how his investing philosophy has evolved while remaining rooted in fundamentals. From flips to long-term rentals, short-term rentals, and even mobile home parks, he discusses why investors should stay flexible and evaluate each opportunity on its own merits rather than forcing every deal into a predetermined strategy. He also shares how having multiple exit strategies creates resilience and protects investors from unexpected market shifts.

The conversation explores how short-term rentals have matured into a more operationally demanding business and why understanding your local market matters more than ever. Henry walks through how his team evaluates markets, why hospitality standards have changed, and how investors can avoid becoming dependent on one strategy that may not work long-term.

Jonathan and Henry also discuss the importance of relationships, local expertise, and returning to old-school investing principles. Henry shares why many experienced investors have become too comfortable in recent years and how getting back to fundamentals—like driving for dollars, making offers, and building real community connections—can create opportunities in any market.

In this episode, you will hear:

• Why managing risk matters more than predicting interest rates or market cycles • How multiple exit strategies create flexibility and protect your investments • The evolution of short-term rentals and why operators must understand their local market • Why experienced investors may need to return to old-school deal-finding methods • How to evaluate opportunities without limiting yourself to one investing strategy • The importance of relationships, trust, and local knowledge in sourcing better deals

Follow and Review

Supporting Resources

Connect with Henry:

Website - www.henrywashington.com

Instagram - @thehenrywashington

Website - www.seeyouattheclosingtable.com

Event - www.roadtotheclosingtable.com

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

YouTube - www.youtube.com/JonathanGreenere

Instagram - www.instagram.com/zenrealestateinvesting

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.

351: The Ethical Way To Wholesale Real Estate Jun 01, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a solo episode focused on the ethical way to wholesale real estate. Drawing from years of observing wholesalers in his New Jersey market and working with clients who have bought from them, Jonathan explains why wholesaling has such a poor reputation — and what wholesalers can do to change that. Rather than dismissing the business model outright, he offers ten guiding principles for building a wholesaling practice rooted in integrity, accuracy, and long-term thinking.

Jonathan breaks down the mindset shifts wholesalers need to make to earn respect in the industry. He introduces his core philosophy: become a bridge, not a toll booth. Instead of positioning yourself in the middle simply to extract the largest spread possible, Jonathan argues that ethical wholesalers act as genuine conduits between sellers and end buyers. He also stresses the critical importance of knowing construction costs, understanding rehab estimates, and using accurate comparable sales rather than inflated ARV figures. Without those fundamentals, wholesalers cannot earn trust — or repeat business.

The episode also explores the dangers of greed and impatience in wholesaling. Jonathan advises against swinging for the fences on every deal, encouraging a singles-and-doubles approach that builds credibility over time. He explains how rushing to lock up deals with unrealistic numbers ultimately destroys a wholesaler's reputation and limits long-term success. By focusing on smaller, more accurate spreads and building a reputation for reliability, wholesalers can attract serious investors who will buy everything they bring to the table.

Throughout the episode, Jonathan challenges wholesalers to rethink their role in the real estate ecosystem. Rather than treating each transaction as a one-time payday, he encourages a relationship-driven model where transparency, competence, and fair dealing create sustainable success. The episode serves as a practical guide for anyone looking to wholesale real estate the right way — with integrity, skill, and a focus on serving both sides of the deal.

In this episode, you will hear:

• Why wholesalers should become a bridge, not a toll booth • How learning construction costs and rehab estimates builds credibility • The importance of using accurate, comparable sales for ARV • Why swinging for the fences on every deal undermines long-term success • How transparency and fair spreads attract repeat buyers • The dangers of inflated numbers and unrealistic expectations

Follow and Review

Supporting Resources

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

YouTube - www.youtube.com/JonathanGreenere

Instagram - www.instagram.com/zenrealestateinvesting

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.

350: The Mindful Approach To Landlording May 28, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a solo episode focused on the mindful approach to landlording. Drawing from his own experiences managing rental properties alongside his father at a young age, Jonathan explains why successful landlording goes far beyond simply collecting rent. Instead, he emphasizes that long-term success comes from building respectful relationships, properly maintaining properties, and viewing tenants as caretakers of the investment rather than as adversaries.

Jonathan breaks down the mindset shifts landlords need to make to create better tenant experiences and stronger long-term property performance. He discusses why choosing the right tenant is one of the most important decisions an investor can make and explains how understanding local demographics, tenant "avatars," and neighborhood dynamics can help landlords attract higher-quality renters. He also shares practical advice on screening tenants, verifying employment, and avoiding costly mistakes driven by desperation or impatience.

The episode also explores the importance of communication, curb appeal, and operational systems in creating stable rental properties. Jonathan explains how exterior upkeep, common area maintenance, parking rules, and laundry schedules all contribute to tenant satisfaction and lower turnover. He highlights why landlords should remain approachable and present rather than hiding behind LLCs or management companies, stressing that accountability and accessibility often lead to better tenant relationships and better care for the property itself.

Throughout the conversation, Jonathan encourages investors to adopt a more thoughtful and human-centered approach to landlording. From allowing tenants to "have their story" during difficult moments to maintaining firm but fair boundaries, he explains how empathy and professionalism can coexist with the protection of the investment. Ultimately, the episode serves as a practical guide for creating healthier landlord-tenant relationships while maximizing long-term property performance.

In this episode, you will hear:

• Why tenants should be viewed as caretakers of an investment property • How choosing the right tenant can determine long-term property success • Why landlords should understand local demographics and tenant "avatars" • The importance of curb appeal, common area upkeep, and clear house rules • How communication, responsiveness, and accountability improve tenant relationships • Why landlords should avoid making desperate or rushed tenant decisions • How empathy, boundaries, and professionalism create better long-term outcomes

Follow and Review

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/streamlinedproperties

Article: https://www.linkedin.com/pulse/buy-hold-investors-guide-finding-hiring-firing-property-ruelens-evm1e/

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.

349: How To Find, Hire, and Fire Property Managers with Jennifer Ruelens May 25, 2026

Show notes

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

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

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/streamlinedproperties

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.

348: Everything You Need To Know About House Hacking May 21, 2026

Show notes

*]: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

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/streamlinedproperties

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.

347: Real Estate Investing Lessons From My Dad May 18, 2026

Show notes

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

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/streamlinedproperties

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

Facebook - www.facebook.com/zenandtheartofrealestateinvesting

Jonathan's Hub Site - www.trustgreene.com

Email - Jonathan@trustgreene.com

346: The 10 Best Books For Real Estate Investors May 14, 2026

Show notes

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

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/streamlinedproperties

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.

345: Owning, Improving, and Building Manufactured Homes with Amanda Cruise May 11, 2026

Show notes

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

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/streamlinedproperties

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.

344: How To Talk To Your Kids About Real Estate Investing May 07, 2026

Show notes

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

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/streamlinedproperties