Zen and the Art of Real Estate Investing

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.

342: How To Run a Cost-Conscious Short-Term Rental with Julie Thomas Apr 30, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Julie Thomas, founder of The STR Edit and The STR Visionary, who shares how she built a successful short-term rental business starting with a $20,000 budget. Julie walks through her journey from being a teacher to becoming an experienced investor and designer, helping others create high-performing STR properties without overspending.

Julie explains how her first investment in West Yellowstone came from poor guest experiences and a desire to do better. She and her husband took a hands-on approach, sourcing furniture creatively, prioritizing key amenities, and focusing on guest experience to dramatically increase revenue and reviews.

The conversation also highlights the biggest misconceptions about short-term rentals, including the idea that they require massive design budgets or operate as passive income. Julie emphasizes the importance of understanding your market, knowing your guest avatar, and balancing both design and operations to create a successful property.

Jonathan and Julie also discuss practical strategies like setting a strict budget, avoiding unnecessary upgrades, and learning from real guest feedback. They stress that strong operations, responsiveness, and attention to detail are just as important as aesthetics when it comes to earning five-star reviews and repeat bookings.

In this episode, you will hear:

How Julie Thomas got started in short-term rentals with a $20K budget
Why most STRs don't require massive design budgets to succeed
The biggest mistakes new investors make when getting started
How to balance design and operations to improve guest experience
Why knowing your market and guest avatar is critical to success

Follow and Review

Supporting Resources

Connect with Julie:

Website: https://www.stredit.com/

LinkedIn: https://www.linkedin.com/in/strvisionary/

Connect with Jonathan:

Podcast - www.zenandtheartofrealestateinvesting.com

Brokerage - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/zenrealestateinvesting

Instagram - www.instagram.com/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.

341: Everything You Really Need To Know About Real Estate is Local Apr 27, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene shares a solo deep dive into one of the most overlooked principles in real estate: everything is local. He explains why understanding a specific market will almost always give you a greater advantage than focusing only on an asset class.

Jonathan breaks down how investors can gain an edge by studying a single market in depth, from neighborhood trends and zoning to migration patterns and local economic drivers. He emphasizes that while geographic diversification is important, each investment decision is still rooted in local knowledge that impacts pricing, demand, and opportunity.

Throughout the episode, he explains how this concept applies across different asset classes, including single-family homes, multifamily, self-storage, industrial, and syndications. By understanding local data and property-level details, investors can uncover opportunities that others miss and avoid relying on generic advice.

He also shares practical ways to build local expertise, including driving neighborhoods, analyzing listings daily, attending planning board meetings, and studying comparable properties. The episode reinforces that success in real estate comes from consistent focus in a specific market rather than chasing trends.

In this episode, you will hear:

Why understanding a local market is more valuable than focusing on an asset class
How to analyze neighborhoods using real-world observations and local data
Ways to identify investment opportunities through zoning, trends, and planning activity
How local knowledge applies across multiple asset classes
Why focusing deeply on one market leads to better investment decisions

Follow and Review

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.

340: Turning Land Investing Into a Real Business with Sumner Healey Apr 23, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Sumner Healey, founder of Land Insights and the Land Investor Accelerator. Sumner shares how he built a land flipping business from scratch and breaks down the strategies, systems, and mindset needed to succeed in today's market.

Sumner walks through his early struggles getting started, from sending handwritten letters with no results to landing his first deal for just over $1,000 and flipping it for a quick profit. He explains how that initial success created a proof of concept that led him to scale into larger deals and eventually build a full business around land investing.

The conversation dives into what makes land unique compared to other real estate asset classes, including its flexibility, scalability, and the wide range of deal sizes available. Jonathan and Sumner also discuss the importance of marketing, pricing, and consistency, along with why many new investors fail due to unrealistic expectations and lack of execution.

Sumner also shares how to identify strong markets, improve listings to sell faster, and think like a business owner instead of just chasing deals. He emphasizes that long-term success comes from building systems, staying consistent, and being willing to learn through repetition.

In this episode, you will hear:

How Sumner Healey got started and closed his first land deal
Why land investing offers flexibility across deal sizes and strategies
The biggest mistakes new investors make when starting out
How to identify strong markets and improve listing performance
Why consistency and treating it like a business are key to success

Follow and Review

Supporting Resources

Connect with Sumner:

Website: http://landinvestor.co/

Youtube: https://www.youtube.com/@landinvestorco

Facebook: https://www.instagram.com/sumnerhealey/

Instagram: https://www.instagram.com/sumnerhealey/

Free Zero To Hero Course: https://landinvestor.co/zerotohero/

Free Trial To LIA: https://www.skool.com/lia/about

Free Land Insights Account: https://www.landinsights.co/lite

Land Insights Free Demo Call (where we will build out your first marketing list with you): https://www.landinsights.co/lite

Connect with Jonathan:

Bigger Pockets: www.biggerpockets.com/users/jonathangreene

Email: info@streamlined.properties

This episode was produced by Outlier Audio.

339: Buying Distressed Real Estate at Auction with Mike Russo Apr 20, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Mike Russo, head of product innovation at Auction.com. With more than 20 years of experience spanning franchising, proptech, and distressed assets, Mike shares how his career evolved from early roles in real estate franchising to building platforms and eventually leading product innovation at the largest distressed real estate marketplace in the United States.

The conversation explores how investors can navigate today's real estate landscape, particularly when it comes to distressed properties, auctions, and identifying real opportunities versus perceived deals. Mike explains how platforms like Auction.com actually work behind the scenes, including reserve pricing, auction dynamics, and why many properties cycle without selling. He also shares practical advice for new investors, emphasizing the importance of starting with lower-risk opportunities like vacant REO properties and building experience through repetition.

Jonathan and Mike also discuss the realities of active investing, from flipping houses to managing rentals, and why many investors underestimate the complexity and operational demands involved. They highlight how technology can be a powerful tool for sourcing deals, but cannot replace on-the-ground knowledge, experience, and due diligence. The episode also touches on market dynamics, investor behavior, and the risks created by inexperience, FOMO, and misinformation.

For investors, this episode offers a grounded perspective on how to approach distressed real estate, avoid common mistakes, and build a sustainable investing strategy over time.

In this episode, you will hear:

How Mike Russo transitioned from real estate franchising to leading product at Auction.com
How online real estate auctions actually work, including reserves and bidding dynamics
Why new investors should start with vacant REO properties instead of jumping into foreclosures
The risks of inexperience, FOMO, and relying too heavily on online deal analysis
Why seeing properties in person and getting real reps is critical for long-term success
How to think about active vs. passive investing and the realities of managing real estate assets

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 Mike

Youtube: http://youtube.com/@mikesrusso

Instagram: @mike.s.russo

LinkedIn: https://www.linkedin.com/in/mikerusso1/

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.

338: Why Most of My Personal Real Estate Deals Fail Apr 16, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene breaks down why most of his recent personal real estate deals have failed, despite decades of experience and a long track record of successful transactions. In this solo episode, he walks through several real deals that fell apart and explains the mindset behind why he chose to walk away from each one.

Jonathan shares how his perspective on investing has shifted as he has become more selective, emphasizing the difference between wanting a deal and actually needing one. He explains how inspections, unexpected costs, and changing assumptions often reveal risks that weren't visible at the outset, and why he is always willing to cancel a deal when the numbers or circumstances no longer make sense.

The episode also explores how negotiation style, ego, and pricing influence outcomes. Jonathan reflects on moments where he may have pushed too hard, as well as deals where walking away was clearly the right decision. Through examples ranging from mixed-use commercial properties to a short-term rental impacted by a natural disaster, he highlights how external factors and new information can quickly change an investment thesis.

For investors, this episode reinforces that failed deals are not mistakes but part of the process. By staying disciplined, unemotional, and willing to walk away, investors can avoid bad outcomes and focus on better opportunities.

In this episode, you will hear:

Why most of Jonathan's recent personal real estate deals have failed
The difference between wanting a deal and actually needing one
How inspections and unexpected costs can derail a transaction
Why being willing to walk away is a critical investing skill
How negotiation style and pricing influence deal outcomes
The impact of external events on an investment thesis

Follow and Review

Connect with Jonathan:

Bigger Pockets: www.biggerpockets.com/users/jonathangreene

Email: info@streamlined.properties

This episode was produced by Outlier Audio.

337: How Income-Producing Properties Create Empowered Investors with Jason Hartman Apr 13, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jason Hartman, CEO of Empowered Investor and a longtime real estate investor with experience across multiple markets and thousands of transactions. Jason shares his perspective on today's housing environment, from higher interest rates to constrained inventory, and explains why these conditions require patience, discipline, and a long-term mindset.

The conversation centers on how investors should think about real estate in a slower, more uncertain market cycle. Jason emphasizes that much of real estate's return is not immediately visible—what he describes as the "iceberg effect"—where appreciation and cash flow are only part of the picture, while loan paydown, tax advantages, and inflation-driven debt reduction happen quietly over time. He also highlights how market conditions, including limited supply and a growing pool of sidelined buyers, could create future pressure on prices when rates eventually decline.

Jonathan and Jason also explore the importance of execution over information. While many investors spend time consuming content and analyzing deals, Jason reinforces that real learning comes from action. They discuss how real estate remains an "imperfect market," where investors can create value, adjust strategies, and improve outcomes over time—unlike more passive asset classes. The discussion also touches on the importance of surrounding yourself with the right people, understanding local markets, and focusing on consistent, repeatable decisions rather than chasing quick wins.

For investors, this episode is a reminder that success in real estate is built through consistency, not timing. Staying active in the market, even during slower periods, allows you to benefit from long-term trends, build experience, and position yourself ahead of future cycles when competition increases.

In this episode, you will hear:

Why much of real estate's return comes from factors investors don't immediately see
How inflation and long-term debt can work in favor of property owners
Why waiting for perfect timing often leads to more competition and higher prices
The difference between learning about real estate and actually doing it
How supply constraints and sidelined buyers could impact future pricing
Why consistency and execution matter more than chasing short-term wins

Follow and Review

Supporting Resources

Connect with Jason Hartman:

Website: https://www.jasonhartman.com/

Youtube: https://www.youtube.com/@JasonHartmanEmpoweredInvestor

Facebook: https://www.facebook.com/jason.hartman

Instagram: https://www.instagram.com/jasonhartman1/

Linkedin: https://www.linkedin.com/in/jasonhartmaninvestor/

Twitter: https://x.com/JasonHartmanROI

Connect with Jonathan:

You Tube: https://www.youtube.com/jonathangreenere

Instagram: www.instag.ram.com/streamlinedproperties

Bigger Pockets: www.biggerpockets.com/users/jonathangreene

Email: into@streamlined.properties

This episode was produced by Outlier Audio.

336: A Real Estate Journey That Started With a Weekend House with Jennifer Grimes Apr 09, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jennifer Grimes, founder of Country House Realty and Red Cottage Inc., to discuss how she built a short-term rental business before it was widely recognized as an industry. Starting with a single weekend home in upstate New York, Jennifer shares how an impulsive purchase turned into a growing portfolio and eventually a company managing dozens of properties.

The conversation explores the early days of short-term rentals, when platforms like Airbnb were just emerging and most bookings came from Craigslist and direct marketing. Jennifer explains how timing, the 2008 financial crisis, and shifting travel behavior helped fuel demand, allowing her to scale Red Cottage into a 75-property operation while also launching her brokerage.

Listeners will also hear a candid discussion about the realities of short-term rental investing, including operational challenges, pricing complexity, and increasing regulation. Jennifer shares lessons from growing and selling her company, along with insights into today's market and what investors often misunderstand about owning and managing rental properties.

In this episode, you will hear:

How Jennifer built a rental business from a single weekend property
What it was like operating before Airbnb became mainstream
How early marketing strategies helped grow Red Cottage
Lessons from navigating the 2008 financial crisis
How COVID reshaped demand for short-term rentals
Why many investors underestimate the work involved in rentals

Follow and Review

Supporting Resources

Connect with Jennifer

Website: http://countryhouserealty.com/

Youtube: https://www.youtube.com/@countryhouserealty/featured

Facebook: https://www.facebook.com/countryhouserealty

Instagram: https://www.instagram.com/countryhouserealty/

LinkedIn: http://www.linkedin.com/in/jennifergrimes1

Connect with Jonathan:

Bigger Pockets: www.biggerpockets.com/users/jonathangreene

Email: info@streamlined.properties

This episode was produced by Outlier Audio.

335: Turning Land Into New Housing Communities with Brandon Cobb Apr 06, 2026

Show notes

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Brandon Cobb, CEO of HBG Capital and founder of Land Development Accelerator. Brandon shares how he went from an unexpected job loss to building a real estate business focused on land development, entitlement, and scaling into larger, more strategic deals.

Brandon explains why land investing remains less saturated than other real estate niches and how many investors overlook it in favor of more visible strategies like house flipping. He breaks down the progression from flipping houses to building homes and eventually shifting into land development, highlighting how each stage builds the skills needed to operate at a higher level.

The conversation also explores the mechanics behind land entitlement and development, including how to identify opportunities by reverse engineering what large homebuilders are already doing. Brandon shares how a more targeted, relationship-driven approach replaces traditional high-volume marketing, and why understanding the approval process and working with the right professionals can significantly reduce risk.

For investors, this episode reinforces that real estate is a long game built on progression, not shortcuts. Larger opportunities often come from layering new strategies onto an existing foundation, and those who focus on building skills, relationships, and consistent deal flow are better positioned to create long-term wealth through fewer, more impactful deals.

In this episode, you will hear:

Why land investing is often less competitive than other real estate strategies
How Brandon transitioned from house flipping to large-scale land development
The key differences between high-volume marketing and targeted land acquisition
How to identify development opportunities by following major homebuilders
Why entitlement and approval processes create barriers to entry
How land development can serve as a long-term wealth-building strategy

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 Brandon Cobb

Website: https://www.hbgcapital.net/

Youtube: https://www.youtube.com/@hbgcapital662

Facebook: https://www.facebook.com/hbgcapital

Instagram: https://www.instagram.com/hbgcapital/

LinkedIn: https://www.linkedin.com/in/hbgcapital/

Land Development Accelerator: https://learnlanddevelopment.com/

Connect with Jonathan:

Bigger Pockets: www.biggerpockets.com/users/jonathangreene