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Zen and the Art of Real Estate Investing

Zen and the Art of Real Estate Investing

By: Jonathan Greene
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What if you could learn from experienced real estate investors, find out what got them to where they are now, get insight into their daily habits, and take these insights to inspire your own growth? That’s what each episode of Zen and the Art of Real Estate Investing brings. Hosted by Jonathan Greene, a real estate investor for more than 30 years, as well as advisor and coach, the founder of Streamlined Properties and the Team Leader of Streamlined Properties, brokered by Real, every episode is an in-depth look at the mindful approach to real estate investing. If you are looking to start from scratch, get to the next level, or just for a straightforward and honest approach to real estate investing, Zen and the Art of Real Estate Investing is the free mentorship program you can take with you anywhere.2024 Economics Leadership Management & Leadership Personal Finance
Episodes
  • 269: How To Start Living Off Rentals with Kirby Atwell

    269: How To Start Living Off Rentals with Kirby Atwell
    Aug 18 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Kirby Atwell, an Army veteran, real estate investor, and host of the Living Off Rentals podcast. Kirby’s journey from military service to financial freedom offers a practical roadmap for investors seeking a sustainable, high-cash-flow strategy. Kirby’s interest in real estate began in 2006 while stationed in El Paso, Texas, after reading “Rich Dad Poor Dad.” His first purchase, a turnkey property across the street, sparked a career that would include multiple rental acquisitions before leaving the Army in 2011. Initially, Kirby built a high-volume house-flipping business, completing around 75 projects in five years. While the operation looked successful from the outside, the overhead, contractor management, and constant pressure to “feed the machine” made it an unsustainable treadmill. Recognizing that his initial goal was freedom, not endless hustle, Kirby pivoted. After a short return to corporate work, he began acquiring long-term rentals in Northwest Indiana. A chance experiment, turning a basement apartment into an Airbnb, netted $22,000 in one summer, far exceeding the annual income from some of his long-term units. This discovery led him to transition entirely to short-term rentals, focusing on modestly priced multi-unit properties that could also work as long-term rentals if needed. Kirby now manages 39 short-term rental listings, primarily clustered near Michigan City and Valparaiso, Indiana, with additional properties in southwest Florida. By concentrating on one region before expanding, he built economies of scale in operations, supply management, and cleaning services. His strategy centers on risk-averse investing—buying affordable properties in areas with steady demand drivers, from national parks to local universities—while maintaining the flexibility to pivot between rental strategies. Jonathan and Kirby discuss the power of “reps” in real estate, why clustering investments boosts efficiency, and how to vet short-term rental opportunities by analyzing local competition. Kirby also shares his process for furnishing units cost-effectively, his rule of thumb for net returns (1% of purchase price monthly), and the importance of avoiding over-leverage. Today, through his Living Off Rentals platform, Kirby coaches other investors to build similar portfolios. His philosophy combines conservative acquisition criteria with creative income strategies, allowing investors to create both cash flow and long-term equity without the burnout of high-volume flipping. In this episode, you will hear: The importance of taking action before having everything figured out Why scaling a flipping business often leads to burnout and thin margins How an experimental basement Airbnb reshaped Kirby’s investing approach The advantages of clustering short-term rentals in one market Identifying risk-averse properties with strong cash flow potential Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: Living Off Rentals website - www.livingoffrentals.com Living Off Rentals on YouTube - www.youtube.com/@LivingOffRentals Find Living Off Rentals on Facebook - www.facebook.com/LivingOffRentals Living Off Rentals on Instagram - www.instagram.com/livingoffrentals Connect with Kirby Atwell on LinkedIn - www.linkedin.com/in/kirbyatwell Living Off Rentals on TikTok - www.tiktok.com/@livingoffrentals 4 Steps to Living Off Rentals - www.livingoffrentals.com/start Website - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties TikTok - www.tiktok.com/@trustgreene Zillow - www.zillow.com/profile/StreamlinedReal Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/streamlinedproperties Email - info@streamlined.properties Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
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    52 mins
  • 268: Designing and Operating a Boutique Wellness Resort with Diana Ossa and Josh Dobken

    268: Designing and Operating a Boutique Wellness Resort with Diana Ossa and Josh Dobken
    Aug 14 2025

    In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Diana Ossa and Josh Dobken to discuss the creation of their boutique wellness resort in Palm Springs. As a couple with a shared vision for conscious living, they transformed their dream into a real estate venture focused on wellness, sustainability, and community.

    Diana and Josh walk through the real estate challenges and rewards of developing in a foreign country. They talk about their approach to design and development, why they chose Palm Springs, and how they’re creating a guest experience that’s intimate, personalized, and grounded in nature. Their project isn’t just about hospitality. It’s about building something that reflects their values and lifestyle.

    Jonathan explores how they approached the design process, from layout to material selection, and how they balanced the creative aspects with logistical and financial realities. They also discuss the importance of timing, trusting their instincts, and building a brand that speaks to a like-minded audience. Their story offers a firsthand look at how intentional living and real estate investment can align.

    This episode is an honest and inspiring look at what it takes to create a boutique experience that blends business with purpose.

    In this episode, you will hear:

    • Designing a resort around wellness, simplicity, and intentionality
    • Bringing a personal lifestyle vision to life through real estate
    • Prioritizing community, sustainability, and guest experience in every decision
    • The power of trusting intuition and moving at a deliberate pace
    • Lessons from shifting careers into hospitality development

    Follow and Review:

    We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

    Supporting Resources:

    Design - Invest website - www.designinvestfi.com

    Design - Invest on Instagram - instagram.com/d.i.fi

    Terra Palm Springs website - www.terrapalmsprings.com

    Terra Palm Springs on Instagram - www.instagram.com/terrapalmsprings

    Website - www.streamlined.properties

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

    Instagram - www.instagram.com/trustgreene

    Instagram - www.instagram.com/streamlinedproperties

    TikTok - www.tiktok.com/@trustgreene

    Zillow - www.zillow.com/profile/StreamlinedReal

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

    Facebook - www.facebook.com/streamlinedproperties

    Email - info@streamlined.properties

    Episode Credits

    If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
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    59 mins
  • 267: Investing in Real Estate From a Position of Strength with Scott Trench

    267: Investing in Real Estate From a Position of Strength with Scott Trench
    Aug 11 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Scott Trench, former CEO of BiggerPockets, co-host of the BiggerPockets Money podcast, and author of “Set for Life.” Their conversation dives into how Scott achieved financial independence through real estate and frugality, and how new investors can build the confidence and skills to invest from a position of strength. Scott shares how his own path began with house hacking and strict expense management while working as a financial analyst. These early habits laid the foundation for his first duplex purchase and ultimately his real estate success. He explains that the core pursuit behind investing for most people isn’t financial wealth. It’s time freedom. Real estate offers one of the most accessible paths to achieve that, especially for everyday Americans with median incomes. The conversation highlights the importance of personal accountability and developing an in-person community. While online education has its place, Scott emphasizes the lasting value of learning from real people, joining masterminds, and taking action on knowledge, not just theory. He also explains how engaging directly with tenants, even when difficult, builds the playbook necessary for long-term success. Jonathan and Scott discuss why now might actually be an excellent time to buy, especially in smaller multifamily sectors. While high interest rates have sidelined many investors, price adjustments in certain markets have created new windows of opportunity. Scott reflects on his experience with both direct ownership and passive investing in syndications, candidly sharing why he prefers the control and reliability of local real estate over national trends. They also touch on the FIRE (Financial Independence, Retire Early) movement and what early retirement actually means. For Scott, financial freedom isn’t about never working again. It’s about creating more choices. He encourages listeners to ignore the noise, avoid overpriced guru programs, and focus instead on sustainable investing strategies that fit their lives. Throughout the episode, Scott keeps the advice actionable. He urges new investors to think critically, avoid fads, and build a strong foundation through frugality, education, and reps in the field. Whether you’re house hacking, looking at syndications, or considering commercial opportunities, the key is to approach each decision with discipline and awareness. The ultimate goal? Gaining control over your time, finances, and future. In this episode, you will hear: The mindset shift that turned Scott Trench from employee to investor Why house hacking creates a low-risk way to build skills and equity Where many new investors get stuck and how to get unstuck The importance of being a transparent and human landlord Strategies Scott uses to handle difficult tenants without evictions The hidden value of investor forums and local meetups Why it’s smart to stay skeptical of real estate fads The case for small multifamily in today’s market Scott’s view on FIRE and time freedom as the real end goal Ways to assess college vs. trade school from an ROI perspective Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: BiggerPockets website - www.biggerpockets.com BiggerPockets on YouTube - www.youtube.com/biggerpocketsmoney Find BiggerPockets on Facebook - www.facebook.com/groups/BPMoney Scott Trench’s Instagram - www.instagram.com/scott_trench Connect with Scott on LinkedIn - www.linkedin.com/in/scott-trench-53056a22 Scott’s TikTok - www.tiktok.com/@strenchbp Website - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties TikTok - www.tiktok.com/@trustgreene Zillow - www.zillow.com/profile/StreamlinedReal Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/streamlinedproperties Email - info@streamlined.properties Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
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    1 hr and 2 mins
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