300: What You Need To Succeed as a Real Estate Investor in 2026
Zen and the Art of Real Estate Investing
Release Date: 12/04/2025
Zen and the Art of Real Estate Investing
On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jeff Hurst, CEO of Furnish Finder, to explore the fast-growing world of midterm rentals and why they’re becoming an increasingly attractive option for both renters and real estate investors. Jeff explains how monthly furnished rentals serve professionals, relocating families, and healthcare workers—distinctly different from traditional short-term vacation rentals. The conversation breaks down why midterm rentals often deliver better cash flow than long-term rentals with far less operational...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by Jonathan Iger, CEO of Sage Realty Corporation, to explore how a 100-year-old, family-owned real estate company is redefining the modern office experience. Drawing on Sage’s deep roots in New York City office development, Jonathan explains how brand, hospitality, and operational excellence can drive higher tenant retention and long-term value creation. The conversation dives into why office real estate was already changing before COVID, how renewal rates are often misunderstood, and why “experience”...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by Stuart Gethner, a longtime real estate investor, educator, and connector who has spent decades helping investors move from analysis into action. Stuart shares insights from his experience coaching investors and building his own portfolio across multiple market cycles. The conversation centers on why real estate is ultimately a people business. Stuart explains how networking, local market knowledge, and face-to-face relationships help investors avoid costly mistakes—especially when investing out of state...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Nick Corwin, founder of Oak and Ember, to explore what it really looks like to move from long-term rentals into short-term hospitality and eventually into ground-up development. Nick shares how an engineering mindset, strong mentorship, and disciplined downside analysis shaped his early investing decisions. The conversation traces Nick’s evolution from owning Midwest long-term rentals to building unique short-term experiences in the Wisconsin Dells. He explains why chasing the middle of the market can...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Bri West, co-founder of Somerled Designs, to explore how strategic design has become a competitive advantage in today’s short-term rental market. Drawing on her background in marketing and real estate investing, Bri explains why design should be treated as a revenue-driving investment rather than a cosmetic expense. The conversation dives into how niching down on a clear guest avatar, using data to guide design decisions, and prioritizing high-impact spaces can dramatically increase ADR—even if...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Ash Patel, a commercial real estate investor with more than 15 years of experience investing beyond multifamily. Ash shares how an early mixed-use deal opened his eyes to the advantages of commercial assets and ultimately reshaped his entire investing approach. The conversation explores why many commercial assets are misunderstood or overlooked, including office, retail, medical, and mixed-use properties. Ash explains how changing work patterns, suburban growth, and market cycles are creating rare...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Jennifer Ruelens, a longtime property manager and unapologetic truth-teller in the real estate industry. With more than two decades of hands-on experience, Jennifer shares what buy-and-hold investors often misunderstand about property management, tenant relationships, and the real work required to make rentals perform over time. The conversation explores why real estate investing is rarely passive, how deferred maintenance and avoidance cost investors far more than management fees, and why many...
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Jonathan Greene is joined by August Biniaz, co-founder and CIO of CPI Capital, to explore how early exposure to real estate shaped August’s investing philosophy and led him from single-family investing into large-scale multifamily and build-to-rent strategies. August shares how his family’s experience with real estate as a hedge against inflation influenced his long-term view on housing and capital preservation. The conversation dives into the realities of syndication, from learning the GP/LP structure through trial and error to building investor trust, infrastructure, and discipline over...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Bob Fraser, bestselling author of Invest Like a Billionaire and CFO and Chief Macro Strategist at Aspen Funds. Bob shares how billionaire investors moved away from traditional 60/40 portfolios toward alternative investments—and why everyday investors can adopt the same mindset without billionaire-level wealth. Throughout the conversation, Bob explains why professionally managed real estate is often the most approachable entry point into alternatives, especially for investors who want...
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On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Greg Trotter, CEO and founder of Commercial Building Consultants, to unpack what real estate investors often miss during commercial due diligence. With over 40 years of experience in construction, inspections, and forensic building analysis, Greg explains how his role is to act as a “bodyguard” for investors—protecting their equity by identifying real risks before they close. Greg walks through how property condition assessments should align with an investor’s hold period and exit strategy,...
info_outlineJonathan Greene delivers a solo milestone Episode 300, reflecting on what real estate investors really need to succeed in 2026. Drawing on 300 episodes’ worth of conversations and ten key questions generated by ChatGPT, he walks through interest rates, debt and recapitalization risk, local supply and demand, asset selection, and how to think about the next phase of the market rather than trying to predict it.
He shares how he’s approaching the year ahead himself—doubling down on being an “asset hunter,” investing as an LP in multifamily syndications, eyeing self-storage and Main Street mixed-use, and planning to add a short-term rental in upstate New York. Along the way, Jonathan talks about meetups, possible future retreats, and long-term plans to bring real estate education to younger generations, all while emphasizing the importance of daily research in your buy box over obsessing about national headlines.
Listeners will hear why mindset and mental health come before any big investment move, how to vet operators in syndications, and why diversification by geography, asset type, and vehicle can help you weather whatever 2026 brings. Jonathan closes with reflections on legacy, his parents’ influence, and what it means to build a real estate portfolio that actually supports a meaningful life.
In this episode, you will hear:
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Why Jonathan treats interest rates as just one part of the deal calculation—and why waiting for “3% again” is a losing strategy.
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How to focus on your local buy box, study hot sheets, and spot the path of progress instead of obsessing over national housing headlines.
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The asset classes and strategies he’s most interested in for 2026, from multifamily syndications and short-term rentals to self-storage and Main Street mixed-use.
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Why your mental health, personal life stability, and partner alignment are non-negotiables before making major investment decisions.
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How he uses tools like ChatGPT and data to research regulations, stress-test opportunities, and build more resilient, diversified portfolios without outsourcing his judgment.
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Supporting Resources
Connect with Jonathan:
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
Zillow - www.zillow.com/profile/streamlinenj
Bigger Pockets - www.biggerpockets.com/users/jonathangreene
Facebook - www.facebook.com/streamlinedproperties
Email - info@streamlined.properties
This episode was produced by Outlier Audio.