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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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About this listen

 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
  • 275: Leveraging Multifamily Real Estate For Long-Term Growth with Kent Ritter

    275: Leveraging Multifamily Real Estate For Long-Term Growth with Kent Ritter
    Sep 8 2025
    In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Kent Ritter, CEO and founder of Hudson Investing. Kent’s path into real estate began after selling his healthcare consulting business, which left him looking for ways to diversify his capital. Starting as a passive investor in multifamily syndications, he eventually transitioned into active investing, experimenting with house flipping and single-family rentals before fully committing to multifamily. In 2019, he launched Hudson Investing, a firm focused on building wealth through multifamily syndications with a strong presence in the Midwest. Jonathan and Kent explore the turning points in Kent’s career, including his decision to bring property management in-house. Kent explains how frustration with third-party managers pushed him to create his own team, which improved operational control, reduced turnover costs, and allowed him to align company culture with resident experience. They also discuss renovation strategies, with Kent emphasizing the importance of investing in upgrades residents use every day, such as faucets, thermostats, and cabinet pulls, while balancing affordability and return on investment. The conversation also touches on the advantages of focusing on Midwest markets, where Hudson Investing has found consistent demand and steady fundamentals. Kent highlights the value of building a strong investor community, noting that transparency, education, and shared opportunities foster long-term success. For both passive and active investors, this episode shows how thoughtful leadership, strategic decisions, and multifamily real estate can create reliable, long-term growth. In this episode, you will hear: Kent’s transition from healthcare consulting to real estate investing Lessons he gained as a passive investor before becoming an operator The benefits of bringing property management in-house Renovation strategies that balance affordability with meaningful upgrades How reducing turnover drives stronger property performance The value of curb appeal and amenities alongside interior finishes Opportunities found in Midwest multifamily markets The role of community and investor alignment in scaling a portfolio Tax strategies that can improve investment outcomes 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: Hudson Investing website - www.hudsoninvesting.com Find Kent Ritter on Instagram - www.instagram.com/ritteronrealestate Connect with Kent on LinkedIn - www.linkedin.com/in/kentritter 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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    49 mins
  • 274: Repositioning Shopping Centers in Hometown Markets with Andy Weiner

    274: Repositioning Shopping Centers in Hometown Markets with Andy Weiner
    Sep 4 2025
    Shopping centers may not dominate headlines like multifamily or industrial, but they remain one of the most overlooked opportunities in commercial real estate. In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Andy Weiner, founder and president of RockStep Capital, to discuss how shopping centers, especially in hometown markets, continue to thrive. Andy shares his unique approach to repositioning retail properties, building coalitions with local leaders, and investing where others often overlook. With decades of experience in retail and real estate, Andy has witnessed firsthand how Amazon, shifting consumer habits, and COVID have transformed the shopping center landscape. Instead of retreating, he’s leaned into markets with essential drivers—universities, military bases, strong hospital systems, and tourism—that support community retail. His RockStep coalition model brings together local investors, banks, and municipalities to revitalize shopping centers, creating not just strong investments but also community anchors. Jonathan and Andy explore the nuances of evaluating tenants, identifying markets with sustainable growth, and managing assets in a way that prioritizes both profitability and long-term community impact. This conversation challenges the narrative that retail is dead, highlighting why shopping centers in secondary and tertiary markets may be some of the most compelling opportunities available today. In this episode, you will hear: The philosophy behind RockStep Capital and the meaning of rock step in business Andy’s journey from family retail operations to shopping center investment The distinctions between grocery-anchored centers, power centers, and enclosed malls Investment advantages in hometown markets with strong community ties The role of local business leaders, banks, and municipalities in successful retail repositioning How positive leverage creates strong yields in shopping center investments Considerations for smaller retail properties as a starting point for new investors Ways demographics and employment drivers shape retail viability 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: RockStep Capital website - rockstep.com The Shopping Center on YouTube - www.youtube.com/@TheShoppingCenterChannel Andy Weiner on Instagram - www.instagram.com/theshoppingcenterguy Connect with Andy on LinkedIn - www.linkedin.com/in/andy-weiner 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.
    Show More Show Less
    45 mins
  • 273: Why An ESPN SportsCenter Anchor Is Knee-Deep in Real Estate with Gary Striewski

    273: Why An ESPN SportsCenter Anchor Is Knee-Deep in Real Estate with Gary Striewski
    Sep 1 2025

    What happens when a SportsCenter anchor trades in highlight reels for house hacking?

    In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes ESPN’s Gary Striewski to share his story of becoming a DIY real estate investor while holding down a demanding broadcasting career. Gary takes listeners inside his approach to building wealth, one property at a time, without falling into the “guru culture” that dominates so much of real estate social media.

    Gary’s journey began with his first home purchase in 2018, following his move to ESPN, which later paved the way for house hacking, renovations, and rental strategies. Today, he balances a full-time media career with managing a growing portfolio of long-term, short-term, and mid-term rentals across Connecticut and New Hampshire. His story is one of perseverance, adaptability, and treating tenants like partners rather than numbers.

    From his early days of renovating while living without plumbing, to buying properties straight off the MLS, to learning the power of patience in real estate, Gary demonstrates how an intentional, human-centered approach can turn steady progress into a lasting portfolio. He and Jonathan also dive into the myths of instant wealth, why real estate should be viewed as a long game, and how personal discipline and flexibility create the foundation for success.

    Tune in to hear how Gary Striewski proves that balancing a full-time career with intentional real estate investing is not only possible but deeply rewarding.

    In this episode, you will hear:

    • Gary’s path from SportsCenter anchor to hands-on real estate investor

    • The advantages of using a primary residence as a future rental property

    • Why he calls tenants “guests” and how that mindset strengthens relationships

    • Lessons learned from house hacking, renovations, and managing properties himself

    • How short-term and mid-term rentals fit into his portfolio strategy

    • The role patience, adaptability, and strong communication play in real estate success

    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:

    Gary Striewski’s Instagram - www.instagram.com/thekimchipapi

    Gary’s on TikTok - www.tiktok.com/@thekimchipapi

    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.
    Show More Show Less
    57 mins
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