Zen and the Art of Real Estate Investing

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.

318: The Rise of Mid-Term Rentals As Housing's Fastest-Growing Segment with Jeff Hurst 02/05/2026

318: The Rise of Mid-Term Rentals As Housing's Fastest-Growing Segment with Jeff Hurst 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 intensity than short-term rentals. Jeff also shares insights from Furnish Finder’s first-of-its-kind housing market report, created in partnership with AirDNA, revealing just how durable and widespread demand for monthly rentals has become across the U.S. Listeners will walk away with a clearer understanding of where midterm rentals fit between long-term and short-term housing, how investors are discovering this niche, and why this category may continue to grow as housing affordability, mobility, and lifestyle preferences evolve. In this episode, you will hear: Why midterm rentals serve a fundamentally different tenant base than short-term rentals How furnished monthly rentals can outperform long-term rentals with less management Key insights from the Furnish Finder and AirDNA housing market report Why hospitals, universities, and commuter corridors are strong midterm rental locations How investors can reduce risk by underwriting midterm rentals as long-term deals 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 Jeff: Website: Youtube: Facebook: Instagram: LinkedIn: The Report: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39928050

317: How Commercial Real Estate Can Enrich The Lives of People at Work with Jonathan Iger 02/02/2026

317: How Commercial Real Estate Can Enrich The Lives of People at Work with Jonathan Iger 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” has become a core driver of NOI and asset performance. Jonathan also shares how Sage applies hospitality principles like consistency, service recovery, and “surprise and delight” to create differentiated office environments that tenants don’t want to leave. Listeners will gain insight into where the office market is heading, how branded office platforms can create alpha for investors, and why the future of office belongs to owners who treat buildings as long-term relationships rather than short-term transactions. In this episode, you will hear: How Sage Realty evolved from traditional office ownership into a branded office platform Why tenant renewal rates are far lower than most underwriting assumptions The role of hospitality, SOPs, and service recovery in commercial real estate How experience-driven offices can increase rents, NOI, and long-term asset value Why office real estate isn’t dead, but fundamentally changing 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 Jonathan: Website: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39928000

316: How To Break Through Your Income Ceiling With Real Estate with Stuart Gethner 01/29/2026

316: How To Break Through Your Income Ceiling With Real Estate with Stuart Gethner 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 or relying too heavily on online education. He and Jonathan discuss the limits of “YouTube University” and why real confidence comes from real conversations with experienced investors. Jonathan and Stuart also dive into partnerships, property management, and investor self-awareness. From understanding your personal strengths to building complementary partnerships and avoiding shiny object syndrome, the episode emphasizes patience, humility, and long-term thinking as foundations for sustainable investing success. In this episode, you will hear: Why networking groups accelerate investor confidence and clarity The risks of relying solely on online education without local insight How partnerships work best when both sides have equal skin in the game Why investing close to home often reduces operational risk How patience and long-term thinking outperform “get rich quick” strategies 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 Stuart: Website: Youtube: Facebook: Instagram: LinkedIn: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39853810

315: Thinking Outside the Short-Term Rental Box with Nick Korwin 01/26/2026

315: Thinking Outside the Short-Term Rental Box with Nick Korwin 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 be a losing strategy, how combining units and serving overlooked guest segments created an edge, and why operating short-term rentals requires far more systems and empathy than most investors expect. Jonathan and Nick also unpack the realities of entitlement risk, zoning battles, and development timelines. Nick offers a candid look at what it takes to push a project through local approvals, manage rising costs, and stay grounded when timelines and budgets inevitably expand. In this episode, you will hear: Why testing whether you even like being a landlord matters before scaling How Nick identified underserved short-term rental niches instead of competing in crowded markets The operational differences between long-term rentals and hospitality businesses Lessons learned from zoning, entitlement hurdles, and community resistance Why doubling both your budget and timeline can save you from painful surprises 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 Nick: Website: Youtube: Instagram: LinkedIn: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39853775

314: Why Higher Short-Term Rental Rates Start With Better Design with Bri West 01/22/2026

314: Why Higher Short-Term Rental Rates Start With Better Design with Bri West 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 occupancy is lower. Bri also shares insights from managing and designing hundreds of short-term rentals nationwide, including common mistakes investors make, how to think about amenities and bed configurations, and why lifestyle photography and branding are no longer optional. Listeners will come away with a clearer framework for evaluating short-term rental opportunities, aligning design with long-term investment goals, and standing out in increasingly saturated markets. In this episode, you will hear: Why short-term rental design should start with data and investment strategy, not personal taste How niching down on a specific guest experience can outperform “general” properties The role of amenities, durability, and bed layout in guest satisfaction and reviews Why branding and lifestyle photography directly impact bookings and pricing power How to think about long-term competitiveness as markets become more saturated 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 Bri: Website: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39789810

313: Learning To Invest Beyond Multifamily In Growth Markets with Ash Patel 01/19/2026

313: Learning To Invest Beyond Multifamily In Growth Markets with Ash Patel 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 opportunities to acquire high-quality commercial buildings at deep discounts, often well below replacement cost. Jonathan and Ash also dig into the mindset required to succeed in real estate, the dangers of chasing trends promoted on social media, and why newer investors may benefit from escaping overcrowded asset classes. This episode offers a grounded look at how flexibility, curiosity, and long-term thinking can open doors to less competitive—and often more resilient—investment opportunities. In this episode, you will hear: How Ash transitioned from residential and mixed-use into commercial real estate Why office, retail, and medical assets are misunderstood by many investors How market cycles create opportunities across different commercial asset classes The risks of following social-media-driven investment trends Why parking, location, and tenant mix matter more than asset labels How mindset plays a larger role than mechanics in long-term success 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 Ash: Website: Youtube: Facebook: Instagram: LinkedIn: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39702015

312: A Playbook For Buying and Holding Rental Properties with Jennifer Ruelens 01/15/2026

312: A Playbook For Buying and Holding Rental Properties with Jennifer Ruelens 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 landlords struggle when they underestimate the human side of housing. Jennifer explains how professional property management reduces risk, stabilizes assets, and helps investors focus on long-term wealth rather than short-term cash flow. Listeners will also hear a candid discussion about ego, DIY investing, family dynamics, and why many investors fail not because of bad deals, but because they avoid hard conversations and responsibility. This episode offers a grounded, experience-driven perspective on what it really takes to succeed with buy-and-hold real estate. In this episode, you will hear: Why buy-and-hold real estate is a business, not a passive investment How poor property management decisions erode long-term returns The true cost of deferred maintenance and conflict avoidance Why professional management often increases NOI despite added fees How stabilizing properties protects both tenants and investors The role of expectations, transparency, and service in tenant retention 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 Jen: Website: Youtube: Facebook: Instagram: LinkedIn: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39701990

311: Building a Wealth Creation Value-Add System with August Biniaz 01/12/2026

311: Building a Wealth Creation Value-Add System with August Biniaz 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 time. August explains why CPI focuses on U.S. markets like Tampa and San Antonio, how oversupply cycles create both risk and opportunity, and why patience and underwriting discipline matter more than deal volume. Jonathan and August also discuss the value of passive investing, especially for professionals who want real estate exposure without taking on a second job. August outlines how investors can think clearly about asset classes, sponsors, and alignment before committing capital, emphasizing that trust and communication are just as important as returns. In this episode, you will hear: How early family exposure to real estate can shape long-term investing instincts Why August transitioned from development into real estate private equity The differences between Canadian and U.S. multifamily investing environments How CPI evaluates Tampa and San Antonio amid oversupply and shifting demand Why being a limited partner can be the best education for future operators What passive investors should consider when choosing asset classes and sponsors 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 August: Website: Youtube: Facebook: Instagram: LinkedIn: Twitter: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39677515

310: Learning How To Invest Like a Billionaire with Bob Fraser 01/08/2026

310: Learning How To Invest Like a Billionaire with Bob Fraser 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 exposure without taking on a second full-time job. He and Jonathan explore the differences between active and passive investing, the importance of aligned partnerships, and why many investors underestimate the operational demands of being a landlord. The discussion then dives deep into macro-driven investing, with Bob outlining why industrial real estate stands out today due to reshoring trends, logistics demand, and lower construction and operational complexity compared to multifamily. Bob also explains why fund structures can be more efficient than single-asset syndications, offering better capital deployment, diversification, and investor control—especially around taxes and liquidity. In this episode, you will hear: Why billionaires shifted away from traditional portfolios toward alternatives How everyday investors can think like billionaires without massive capital The difference between active real estate and truly passive investing Why industrial real estate is outperforming multifamily in the current cycle How fund structures can improve diversification, tax efficiency, and liquidity What macro trends Bob looks for when evaluating alternative investments 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 Bob: Website: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39617985

309: Redefining the Standards of Commercial Real Estate Services with Greg Trotter 01/05/2026

309: Redefining the Standards of Commercial Real Estate Services with Greg Trotter 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, why cosmetic upgrades are often a distraction, and how overlooked systems like roofs, drainage, lift stations, and life-safety infrastructure can quietly derail deals. He also shares stories from projects across the U.S. and beyond, highlighting how climate, weather events, deferred maintenance, and operational blind spots create long-term financial consequences. Listeners will gain a deeper understanding of why transparency, conservative planning, and honest reporting matter more than optimism in underwriting—and how knowing the full story of a building can protect both operators and investors from costly surprises down the line. In this episode, you will hear: How Greg’s construction background led him into commercial inspection and consulting Why due diligence must account for hold period, capex timing, and exit strategy Commonly overlooked risks like drainage, roofing, lift stations, and life-safety systems How deferred maintenance compounds into multimillion-dollar problems Why weather events, storm surge, and climate risks are changing how buildings must be evaluated The difference between cosmetic improvements and protecting long-term asset value 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 Greg Website: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39425115

308: Empowering Intelligent Investors Through BRRRR Loans with Joel Kraut 01/01/2026

308: Empowering Intelligent Investors Through BRRRR Loans with Joel Kraut On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Joel Kraut, co-founder and managing director of BRRRR Loans, to explore the realities of long-term real estate investing, private lending, and sustainable financial decision-making. Drawing on decades of experience as an investor, lender, and former Wall Street trader, Joel challenges popular investing shortcuts and explains why slowing down and mastering fundamentals is often the fastest path to real wealth. The conversation dives deep into the limitations of the FIRE movement, the dangers of over-leverage, and how emotional decision-making derails otherwise solid deals. Joel shares lessons from market cycles, early BRRRR strategies, and hard-earned mistakes, emphasizing that success in real estate is far more about people, preparation, and honesty than chasing the newest strategy or acronym. Listeners will gain practical insight into what lenders actually look for in borrowers, how to present deals professionally, why organization and credit discipline matter, and how long-term relationships—not hype—drive consistent success in real estate. In this episode, you will hear: Why the FIRE movement often overlooks patience and foundational investing How Joel’s early real estate and refinancing experience shaped his lending philosophy The real dangers of over-leverage and market-specific concentration risk What private lenders look for beyond credit scores and projections Why honesty, preparation, and organization matter more than clever deal structures How long-term relationships create repeat business and lasting wealth 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 Joel: Website: Youtube: Facebook: Instagram: Instagram: LinkedIn: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39415440

307: Helping Real Estate Investors Win One Deal at a Time with Steve Afra 12/29/2025

307: Helping Real Estate Investors Win One Deal at a Time with Steve Afra On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Steve Afra, a nationally recognized real estate finance expert, private lender, and co-founder of Nvestor Funding. Steve shares how growing up in New York’s old-school real estate world shaped his approach to lending, underwriting, and relationships, starting with working alongside his father rehabbing HUD homes and later moving into mortgage lending at a young age. The conversation dives deep into the realities of private lending, including why defaults are rarely about fraud, how life events impact borrowers, and why the goal is always to work deals out—not take properties back. Steve explains what experienced lenders actually look for in borrowers, why presentation and honesty matter more than perfect credit, and how emotional decision-making and best-case-scenario underwriting derail otherwise viable projects. Listeners will walk away with practical insights on evaluating deals conservatively, sourcing opportunities the old-school way, building trust through relationships, and why patience, persistence, and empathy remain the most underrated advantages in real estate investing today. In this episode, you will hear: How Steve got started in real estate and lending at a young age in New York Why private lenders are not “loan-to-own” and actively avoid foreclosures What lenders really look for beyond credit scores and financials Why presentation, track record, and worst-case underwriting matter The dangers of emotional investing and best-case-scenario comps How old-school relationship building still beats technology-only strategies 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 Steve Website: Youtube: Facebook: Instagram: LinkedIn: Website: TikTok: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39415415

306: How To Invest Privately and Grow Strategically with Spencer Hilligoss 12/25/2025

306: How To Invest Privately and Grow Strategically with Spencer Hilligoss On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene speaks with Spencer Hilligoss, CEO and co-founder of Madison Investing, about his journey from growing up in a real estate brokerage household to becoming a thoughtful passive investor and investing club leader. Spencer shares how a long career in Silicon Valley tech shaped his approach to risk, cash flow, and long-term financial planning, and why real estate became a critical tool for building stability beyond W-2 income. The conversation explores Spencer’s transition from owning rental properties to focusing on limited partner investing, including how capacity, family priorities, and operational realities influenced that shift. Spencer breaks down how he evaluates sponsors, why track record and communication matter more than flashy projections, and what recent market cycles have reinforced about conservative underwriting and disciplined deal selection. Listeners will gain clarity on when passive investing makes sense, how to think about risk and accountability as an LP, and why education and mindset—not deal hype—are the foundation of long-term success. In this episode, you will hear: How growing up in a brokerage family influenced Spencer’s investing mindset Why W-2 income alone isn’t enough for long-term financial resilience The transition from owning rentals to passive LP investing How to evaluate sponsors, track record, and deal structure Why “passive” investing still requires active due diligence Lessons learned from recent market shifts and recalibrated return expectations 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 Spencer Website: Website: Twitter: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39415325

305: How To Flip Your Story and Build Real Wealth with Brian Tran 12/22/2025

305: How To Flip Your Story and Build Real Wealth with Brian Tran On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Brian Tran, founding partner of 50 Hills, host of the Winners Club podcast, and a real estate investor with over 100 flips and a multimillion-dollar portfolio. Brian shares how his family’s immigration story shaped his commitment to real estate, the early mistakes he learned from buying in tough neighborhoods, and how those lessons guided his long-term investing strategy. Brian breaks down how he balances appreciation markets like California with cash-flow markets out of state, treating his portfolio the way a financial advisor would diversify assets. He also dives into the role of wholesaling and flipping as active income engines, the importance of delaying gratification, and why mindset—not capital—is the biggest barrier for new investors. Listeners will hear practical guidance on getting started in real estate without shortcuts, why buying your first property matters more than perfect timing, and how treating real estate like a real business creates long-term freedom and stability. In this episode, you will hear: How Brian’s parents’ immigration journey influenced his approach to real estate Why buying in rough neighborhoods taught hard but valuable lessons How to balance appreciation and cash flow across different markets The role of wholesaling and flipping in building investable capital Why mindset and focus matter more than chasing quick wins How buying your first property creates long-term momentum 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 Brian Website: Youtube: TikTok: Instagram: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39376475

304: The Case For Buying a Second Home First with Katie Cline 12/18/2025

304: The Case For Buying a Second Home First with Katie Cline Jonathan Greene welcomes back Katie Cline, a senior global PR and communications leader turned hospitality and short-term rental expert, to explore her evolving philosophy behind Second Home First. Katie shares the personal story that led her to buy a vacation home before a primary residence—and how that unconventional decision unlocked both financial flexibility and deeper family experiences. They discuss why renting in high-cost cities can coexist with smart real estate investing, how short-term rentals can function like a hybrid between lifestyle asset and retirement strategy, and why mindset—not money—is often the biggest barrier holding people back. Katie also explains how designing properties around personal preferences creates stronger guest experiences, better reviews, and more resilient performance across markets. The key takeaway: real estate doesn’t have to follow a single, traditional path. By aligning investments with lifestyle goals, hospitality values, and intentional design, investors can build assets that generate income today while still creating meaningful memories along the way. In this episode, you will hear: What “Second Home First” really means—and why it challenges the traditional homeownership timeline How short-term rentals can provide both lifestyle benefits and long-term financial security Why renting a primary home can offer flexibility while still building wealth through real estate The importance of designing properties around your own preferences and ideal guest avatar How hospitality mindset and intentional design drive better bookings and guest experiences Why breaking from conventional investing narratives can open up more creative opportunities 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 Katie: Website: Youtube: Instagram: LinkedIn: Episode 216: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39260935

303: Building Bold Brands For Your Short-Term Rental or Boutique Hotel with Steph Weber 12/15/2025

303: Building Bold Brands For Your Short-Term Rental or Boutique Hotel with Steph Weber Jonathan Greene sits down with Steph Weber, CEO of The Weber Co., to break down why short-term rental owners can’t rely solely on Airbnb if they want long-term control and growth. Steph explains how direct branding protects your business from platform changes, helps guests connect emotionally to what you offer, and creates a clearer path to repeat stays and referrals. They also dig into what it actually takes to build a brand guests remember, beyond pretty photos and a few amenities. Steph shares how to define a real target audience (often starting with yourself or a past/future version of yourself), how to turn amenities into guided experiences, and why collecting guest emails is one of the simplest, most overlooked moves STR operators can make. The biggest takeaway: today’s STR world isn’t a side hobby—it’s a hospitality business. And the operators who win are the ones who design intentionally, market consistently, and build a brand they own. In this episode, you will hear: Why direct branding matters when you don’t control the platform that drives bookings How Airbnb changes can impact hosts—and why brand autonomy is the hedge What it means to create a “branded guest experience” (not just a place to sleep) How to define your avatar and design for a specific audience (not the masses) Why email lists are “low-hanging fruit” and how they power direct bookings Turning amenities into intentional rituals and guided experiences guests remember 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 Steph: Website: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39260290

302: From Ranching To Real Estate Investing with Joe Rinderknecht 12/11/2025

302: From Ranching To Real Estate Investing with Joe Rinderknecht Jonathan Greene sits down with Joe Rinderknecht, multifamily investor and co-founder of Cowboy Capital, to explore how he built a real estate portfolio by staying curious, solving problems, and building long-term relationships with owners. Joe shares how he broke into multifamily with seller financing, how he used subject-to strategies to help owners avoid foreclosure, and why empathy has become foundational to his investing style. Jonathan and Joe also explore the lessons learned from managing smaller properties, scaling into larger ones, and developing the operational discipline needed to create durable performance. Throughout the conversation, Joe explains how he approached deal structure early in his career, the importance of understanding seller pain points, and how his “word is bond” philosophy continues to shape the way he raises capital and works with investors now. He also reflects on partnership dynamics, risk tolerance, and the evolution from doing everything yourself to delegating, documenting, and building systems that allow a team to grow. Listeners will walk away with a grounded reminder that momentum in real estate often comes from doing the right thing—helping people, thinking long-term, and being willing to learn from every deal, no matter the size. In this episode, you will hear: How Joe got into multifamily through seller financing and why creative structures helped him get started without traditional barriers. The subject-to foreclosure story that shaped Joe’s understanding of empathy, negotiation, and long-term relationship building. Why smaller properties became Joe’s training ground for learning asset management, communication, and systems. How Joe’s risk tolerance shifted over time and how partnership dynamics supported that growth. The importance of documentation, checklists, and processes as a business scales. Why Joe believes relationships—not deals—are the real foundation of a sustainable real estate career. 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 Joe: Website: Youtube: Facebook: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39260265

301: Award-Winning Design for Commercial Real Estate with Marcy Sagel 12/08/2025

301: Award-Winning Design for Commercial Real Estate with Marcy Sagel On this week’s episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with interior designer Marcy Sagel, founder and principal of MSA Interiors, a nationally recognized commercial design firm specializing in multifamily, senior housing, healthcare, and large-scale developments. They explore how smart design decisions can dramatically impact renter experience, tenant retention, and net operating income—often without blowing up the budget. Marcy shares the story of how a single project with a supportive architect-mentor evolved into a portfolio of large-scale multifamily and healthcare work across the country. From there, Jonathan and Marcy dive into the details that operators often overlook: how lobby art and amenities shape first impressions, why designers insist on holding the spec once materials are chosen, and how transparency around product pricing can protect both developers and residents. Marcy explains why functionality is just as important as aesthetics—things like where the sofa and TV actually fit, whether you can get a couch down the hallway, and how closet space, bathrooms, lighting, and unit layouts influence who wants to live in a building and how much they’re willing to pay. They also talk about how COVID changed amenity expectations, from coworking and Zoom rooms to package rooms, cold storage for grocery delivery, pet wash stations, and creative vending concepts for residents. Marcy highlights the unique demands of healthcare and senior living design, including memory care safety, assisted living functionality, and the importance of natural light and outdoor access in driving wellness. Throughout the conversation, she comes back to one central idea: if owners think about residents first and involve a design team early, they can future-proof their properties, reduce turnover, and outcompete newer projects for years to come. In this episode, you will hear: How Marcy transitioned from residential design into large-scale multifamily, healthcare, and senior living projects with the help of an architect-mentor. Why involving an interior designer early in a project can save money, prevent costly change orders, and create a cohesive, long-lasting design. Practical ways to upgrade B-class and affordable communities—on a HUD-constrained or tight construction budget—without sacrificing aesthetics. The design details that residents care about most: closet size, bathroom finishes, in-unit laundry, lighting, circulation, and furniture-friendly layouts. How COVID reshaped amenity programming with coworking areas, Zoom rooms, package rooms, cold storage, pet amenities, and flexible vendor spaces. The role of design in building community, reducing turnover, and making residents—and their families in senior living—feel safe, connected, and at home. 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 Marcy: Website: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39259965

300: What You Need To Succeed as a Real Estate Investor in 2026 12/04/2025

300: What You Need To Succeed as a Real Estate Investor in 2026 Jonathan 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: Why Jonathan treats interest rates as just one part of the deal calculation—and why waiting for “3% again” is a losing strategy. How to focus on your local buy box, study hot sheets, and spot the path of progress instead of obsessing over national housing headlines. 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. Why your mental health, personal life stability, and partner alignment are non-negotiables before making major investment decisions. How he uses tools like ChatGPT and data to research regulations, stress-test opportunities, and build more resilient, diversified portfolios without outsourcing his judgment. 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 Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39199385

299: Accelerating Access to EV Charging for Real Estate Portfolio Owners with Benjamin Kanner 12/01/2025

299: Accelerating Access to EV Charging for Real Estate Portfolio Owners with Benjamin Kanner On this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Benjamin Kanner, CEO and co-founder of 3V Infrastructure, a company focused on delivering long-term, scalable EV charging solutions for multifamily portfolios. With a background spanning commercial real estate, renewable energy project finance, and multiple startups, Ben brings a uniquely holistic view of how electrification intersects with property ownership and investor demand. His company’s model—installing, owning, and operating EV chargers at no cost to property owners—creates a compelling new amenity for renters while helping owners stay ahead of rapidly shifting consumer expectations. Throughout the conversation, Ben and Jonathan discuss the accelerating adoption of electric vehicles, why multifamily properties sit at the center of this transition, and the economic forces shaping the need for reliable, long-dwell charging infrastructure. Ben explains the cost drivers behind EV ownership, how modular battery technology is evolving, and why Level 2 charging is the most practical option for home-based needs. He also breaks down how 3V underwrites utilization, diversifies risk across large portfolios, and helps property owners increase rents and tenant satisfaction—all without capital outlay. Listeners will gain a deeper understanding of how EV charging impacts NOI, what’s really happening with power demand, why used EV markets will expand rapidly, and how owners can prepare their buildings for the next decade of transportation needs. Whether you’re an LP, a multifamily operator, or simply curious about electrification, this episode highlights the strategic advantage of early adoption. In this episode, you will hear: Why EV adoption has crossed a national inflection point and what that means for multifamily owners. How 3V Infrastructure finances, installs, and maintains EV chargers with no upfront cost to operators. The economics of EV ownership—including maintenance, fueling costs, and battery modularity. Why Level 2 charging is ideal for long-dwell environments like apartment communities. The role of data, utilization modeling, and EV “rent rolls” in determining charger counts. How electrification, grid demand, and infrastructure investment will shape the next decade of CRE. 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 Benjamin: Website: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39081815

298: How To Raise More Capital and Do More Deals with Marcin Drozdz 11/27/2025

298: How To Raise More Capital and Do More Deals with Marcin Drozdz On this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with capital-raising expert and Managing Director of M1 Real Capital Marcin Drozdz. With a track record of raising nine figures across multiple funds and mentoring over a thousand operators through his M1 Inner Circle, Marcin brings a clear, principled perspective to building long-term investor relationships, structuring funds, and understanding how capital really moves in today’s marketplace. His journey from an immigrant childhood in communist Poland to raising hundreds of millions in U.S. real estate adds valuable context to how he approaches trust, process, and scale. Throughout the conversation, Jonathan and Marcin break down the realities of capital raising across economic cycles, the importance of people-first frameworks, and how new investors should think about syndications versus funds. Marcin shares his 3P method—people, process, portfolio—and explains why most syndicators get this backwards. He also dives into how credibility is built over years, not online clips, and why understanding investor pain points is critical to positioning the right opportunities for the right individuals. Listeners will gain insight into how large fund managers think, how to evaluate deals through the lens of return of capital before return on capital, and how authentic relationship-building still drives success—even in a social media–driven world. Whether you’re raising capital, investing passively, or trying to understand the current commercial cycle, this episode offers a grounded, experienced perspective. In this episode, you will hear: Marcin’s 3P capital-raising framework and why people—not deals—must come first. The value of mentorship and apprenticing before raising capital on your own. How funds differ from single-asset syndications and when each structure makes sense. The importance of protecting downside risk and prioritizing return of capital. Why authentic long-term content—not hype—drives investor trust. How today’s debt wall may create a unique acquisition window in multifamily. 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 Marcin Website: Youtube: Facebook: Instagram: LinkedIn: Special Link: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39081810

297: How to Use Money as a Tool to Create Happiness in Your Family’s Life with Gino Barbaro 11/24/2025

297: How to Use Money as a Tool to Create Happiness in Your Family’s Life with Gino Barbaro On this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes back multifamily investor, financial educator, and newly certified money coach Gino Barbaro. Known for his work with Jake & Gino and his educational focus on long-term wealth, Gino joins Jonathan to unpack the deeper connection between money, mindset, family values, and building a legacy. The discussion moves beyond real estate strategy into the emotional and psychological frameworks that shape financial behavior across generations. As the conversation unfolds, Jonathan and Gino explore how childhood experiences influence adult money patterns, why transparency within families matters, and how parents can introduce financial literacy without pressure or fear. Gino also breaks down his philosophy on treating households like businesses, teaching kids financial stewardship, and why thinking like your own “family office” can radically change long-term outcomes. Listeners will come away with a clearer understanding of how to build a mindful, value-driven approach to wealth that supports both personal growth and multigenerational stability. Whether you're raising kids, investing for the first time, or rethinking your relationship with money, this episode offers practical wisdom and grounded inspiration. In this episode, you will hear: How early memories form unconscious money patterns that affect adult decision-making. Why teaching kids autonomy, financial literacy, and values matters more than pushing real estate. The importance of transparency around wealth, planning, and tax strategy within families. Gino’s framework for thinking like a “family office” at any net worth level. How real estate fits into long-term legacy building beyond just assets and cash flow. Why aligning values, mindset, and financial systems creates more stable generational wealth. 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 Gino: Website: Youtube: Facebook: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39081765

296: Designing Investment Properties To Generate Passive Income with Mackenzie Grate 11/20/2025

296: Designing Investment Properties To Generate Passive Income with Mackenzie Grate Jonathan Greene welcomes interior designer, real estate investor, and New York State licensed agent Mackenzie Grate to the show for a conversation about design-forward investing, building a rental portfolio from scratch, and choosing the right strategy for your lifestyle. Mackenzie, known as “Mac of All Trades,” shares how she shifted from working as an assistant principal to becoming a full-time investor and designer, starting with her first long-term rental in Kingston and eventually expanding into short-term rentals, multifamily properties, and design consulting. Jonathan and Mackenzie explore mindset, risk tolerance, and how every investor evolves over time. Mackenzie explains why being clear about your investor identity matters, how to avoid overspending on design choices, and why community and local knowledge are essential for success. Her experience highlights the balance between creativity, practicality, and long-term planning. Listeners will learn what it truly takes to build a sustainable portfolio, from selecting the right first property to managing guest expectations and making design decisions that enhance both functionality and profitability. Mackenzie’s combination of design expertise and hands-on investing experience offers thoughtful guidance for anyone looking to build a portfolio that performs. In this episode, you will hear: How Mackenzie bought her first long-term rental while working full-time in education The most common design mistakes investors make and how to avoid unnecessary spending Why knowing your investor identity should guide every strategic decision How local market knowledge and relationships support short-term rental success What realistic scaling looks like for new investors Why your first property does not need to be your dream property 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 Mackenzie: Website: Instagram: @Mackofalltrades Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39010745

295: Trust Building Through Transparent Property Management Solutions with Chris Grenzig 11/17/2025

295: Trust Building Through Transparent Property Management Solutions with Chris Grenzig Jonathan Greene sits down with Chris Grenzig, founder of JAG Property Management and JAG Capital Partners, a vertically integrated multifamily firm focused on Jacksonville and Orlando. Chris walks through his evolution from working at Toro to moving markets, taking on a 16-unit value-add deal, and learning property and construction management by doing. He and Jonathan explore what it’s been like to operate through COVID, explosive rent growth, and then a sharp pullback in Florida. As the conversation unfolds, Chris breaks down how he approached that first 16-unit acquisition, the role his prior asset management experience played, and why local market knowledge became his unfair advantage. He speaks candidly about Florida’s recent “perfect storm” of falling rents, rising insurance, and higher interest rates, and how those forces have impacted his portfolio and his investors. Chris and Jonathan also get tactical on out-of-state investing, the limits of BRRRR and flipping in today’s environment, and the differences between property management and true asset management. Listeners will come away with a grounded understanding of what it really looks like to buy, renovate, refinance, and hold in a shifting market—and how to keep investor trust when the numbers don’t go as planned. Chris’s experience navigating tough cycles in Florida offers real-world lessons on conservative underwriting, staying honest with investors, and building a property management business that serves both accidental landlords and more sophisticated owners. In this episode, you will hear: How Chris transitioned from working at Toro to moving to Jacksonville and taking on his own 16-unit value-add property Why he chose to self-manage and oversee construction on a deal he’d never managed at that level before How COVID, rent drops, rising insurance, and interest rate hikes combined into a “perfect storm” for Florida multifamily Why local market knowledge and conservative underwriting matter more than ever in today’s environment The realities and limitations of flipping and BRRRR strategies in higher-rate, higher-cost markets What investors should look for in a property manager—and why asset management and property management are not the same thing 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 Chris Grenzig: Website: Facebook: Instagram: LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/39010730

294: Capital Preservation and Resilient Returns Through Real Estate with Ari Rastegar 11/13/2025

294: Capital Preservation and Resilient Returns Through Real Estate with Ari Rastegar On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene welcomes Ari Rastegar, founder and CEO of Rastegar Capital and author of The Gift of Failure. Ari shares his journey from delivering pizzas and attending law school to building a vertically integrated real estate platform with institutional-scale developments across the country. The conversation centers on discipline, philosophy, and how setbacks became the foundation for both his personal growth and business success. Jonathan and Ari explore the mindset behind enduring market “winters,” the cyclical nature of real estate, and why failure is an essential teacher. Ari discusses his approach to entitlements and master-planned communities, his prediction for one of the largest real estate booms in decades, and how technology—from robotics to 3D printing—could reshape the cost and speed of new construction. He also opens up about health, daily habits, and the quiet discipline that sustains high performance in volatile times. Listeners will take away a deeper understanding of how to balance ambition with patience, why zoning and long-term planning are undervalued edges, and what it means to invest in projects—and people—with lasting value. Ari’s story is a reminder that compounding growth begins not in markets, but in the consistency of who you are when no one’s watching. In this episode, you will hear: How a $3,500 land purchase in law school launched Ari’s development career during the run-up to the Great Financial Crisis Why he views market “winter seasons” and failures as essential to building a resilient, multi-billion-dollar real estate platform The demographic, technological, and housing-supply forces that he believes will drive an unprecedented real estate boom over the next decade How personal development, tiny daily improvements, and emotional awareness compound into better business decisions Why zoning, entitlements, and construction innovation (including 3D-printed and robot-built housing) are critical to solving the housing shortage How Rastegar Capital structures large projects so accredited investors can co-invest alongside major institutions 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 Ari: Website: Youtube: Facebook: Instagram: LinkedIn: Twitter: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38929500

293: Real Estate Investments For the Alternative Investor with Scott Lurie 11/10/2025

293: Real Estate Investments For the Alternative Investor with Scott Lurie On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene is joined by longtime Milwaukee investor and lender Scott Lurie. Scott is the founder and owner of F Street Investments and The Hard Money Co., with deep experience in flipping, multifamily, industrial, private equity, and property management. Together, they explore what it really takes to build durable real estate and lending businesses across multiple cycles, from early “We Buy Ugly Houses” days to large multifamily conversions and a nine-figure lending platform. Scott and Jonathan dig into why “local always wins” in real estate, how national wholesalers have damaged the reputation of the industry, and the way relationship-driven business still compounds over decades. Scott explains the economics behind converting older Residence Inn hotels into multifamily, how he thinks about replacement cost and basis, and why tax-incremental financing has been key to new development in southeastern Wisconsin. They also unpack the coming pain in overlevered Class A multifamily, the role banks will play, and how disciplined operators can navigate the next 18 months. Listeners will come away with a clearer picture of what to look for in both operators and lenders, how to think about downside protection, and why character and work ethic are still the real edge in real estate. Scott’s stories from buying hundreds of units at the bottom of the Great Financial Crisis and bootstrapping his lending company offer a grounded blueprint for building something that lasts—without chasing Lamborghinis or social media fame. In this episode, you will hear: How Scott went from a zero-experience franchisee with “We Buy Ugly Houses” in 2003 to a seasoned operator with a nationwide portfolio Why he believes local investors still have a huge edge over virtual buyers and national wholesalers—and how those wholesaler models created reputational damage The business case for converting older Residence Inn hotels into apartments, and why understanding replacement cost and basis matters more than buzzwords Scott’s view on overlevered Class A multifamily, rising interest rates, and the equity erosion he expects to see over the next 18 months How The Hard Money Co. underwrites borrowers (closing only 7–9% of applications) and the behaviors that separate consistently successful flippers from those who end up in foreclosure Lessons from scaling to hundreds of units and a nine-figure lending platform while keeping investors first and building a track record of on-time payments 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 Scott Website: Youtube: Facebook: Instagram: Website: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38893265

292: Why Self Storage is a Recession-Resistant Industry with Joe Downs 11/06/2025

292: Why Self Storage is a Recession-Resistant Industry with Joe Downs Jonathan Greene sits down with self-storage investor and operator Joe Downs, CEO of Bellrose Storage Group, which sources, acquires, and manages self-storage facilities across the East and Southeast. With a background in commercial real estate, capital raising, and distressed second mortgages, Joe explains how he pivoted into self-storage after discovering just how mom-and-pop dominated and under-optimized the space really was. Their conversation explores why self-storage is still far from “too late,” how technology and remote management have transformed operations, and why small, overlooked facilities under 30,000 square feet can be a goldmine for investors willing to modernize them. Joe also breaks down creative plays like boat and RV storage, industrial outdoor storage, and converting large vacant retail boxes into multi-revenue storage campuses. Listeners will come away with a grounded understanding of why self-storage is such a powerful niche, what to look for in a mom-and-pop facility, and how to avoid overpaying by underwriting expenses correctly. Joe and Jonathan also discuss the importance of relationships and “caretaker” mentality with long-time owners, the role of SBA loans, and how to keep shiny object syndrome in check while still recognizing adjacent opportunities. In this episode, you will hear: How Joe went from distressed debt and 1031 capital raising to building a self-storage platform Why self-storage is still largely mom-and-pop owned and what that means for opportunity How technology, remote management, and autopay have transformed facility operations What to look for in a first small storage acquisition and how to approach owners as a “caretaker” The importance of underwriting real expenses (marketing, tech, management) so you don’t overpay Creative self-storage derivatives, including boat and RV storage, IOS, and big-box retail conversions 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 Joe Downs: Website: Facebook: Twitter: @downsjoe LinkedIn: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38893245

291: The Overlooked Asset Class That Outperforms In Uncertain Markets with Tim Woodbridge 11/03/2025

291: The Overlooked Asset Class That Outperforms In Uncertain Markets with Tim Woodbridge In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Tim Woodbridge, co-founder of WCG Investments, to discuss how he transitioned from a healthcare career to building a portfolio of 19 mobile home parks across the Southeast. Tim shares the lessons he’s learned about scaling through partnerships, managing risk with conservative underwriting, and improving communities through value-driven operations. The conversation explores his early challenges finding deals, developing trust with brokers and lenders, and learning how to take imperfect action without losing discipline. Tim explains why collaboration and follow-up matter as much as capital, what separates good due diligence from guesswork, and how his team builds sustainable systems to support investors and residents alike. This episode offers a grounded look at what it takes to grow in a niche asset class while maintaining long-term perspective, thoughtful leadership, and a genuine focus on people. In this episode, you will hear: How partnerships built on complementary strengths lead to better deals The importance of trust and transparency with brokers and lenders Common due diligence pitfalls that can derail returns Why realistic underwriting protects both operators and LPs How consistent follow-up leads to unexpected opportunities The role of community improvements in responsible investing 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 Tim Woodbridge Website: Youtube: Facebook: Instagram: LinkedIn: E-Book - Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - Bigger Pockets - Facebook - Email - This episode was produced by . /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38850050

290: Why Accurate Financials Lead To Better Decisions and More Profit with Max Emory 10/30/2025

290: Why Accurate Financials Lead To Better Decisions and More Profit with Max Emory Jonathan welcomes Max Emory, founder of Time Capital Bookkeeping & CFO Solutions, a bookkeeping educator and active investor. Together, they explore why clean books form the foundation of every real estate business and how accurate categorization impacts both taxes and lending. Max explains what decision-ready financials allow investors to do, including timing acquisitions, managing cash flow, and avoiding costly tax surprises. He also shares why onboarding with a professional bookkeeper is intensive but worthwhile, how your bookkeeper, CPA, and attorney should collaborate, and the most common financial pitfalls he corrects for flippers, wholesalers, and landlords. Max shares his path from serving in the Marine Corps to purchasing his first duplex in Columbia, South Carolina, and scaling through clustered small multifamily properties using the BRRRR strategy. He discusses early challenges such as hiring and firing property managers, building a technology-driven team, and using neighborhood comps and appraisals to improve accuracy. He explains how commingling funds can disrupt operations and increase bookkeeping costs, how simple categorization mistakes can inflate taxable income by thousands, and how to adjust profit and loss reporting to support specific goals, whether maximizing lendability or minimizing taxes. Listeners will leave with a clear checklist for preparing to hire a professional bookkeeper, an understanding of which financial metrics matter most, and the confidence to treat bookkeeping as a strategic advantage rather than a yearly obligation. In this episode, you will hear: Why bookkeeping is the financial foundation—and how it drives tax strategy, lending, and acquisitions The most expensive mistakes Max sees (miscategorization, commingling, missing capex visibility) How to align your bookkeeper, CPA, and attorney so your entity structure helps operations A simple starter system for receipts, statements, and deal docs (even before you hire help) When and why to keep taxable income high (and when to compress it) 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 Max Emory Website: Youtube: Facebook: Instagram: LinkedIn: Tik Tok: Instagram: Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - j Bigger Pockets - Facebook - Email - This episode was produced by /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38799340

289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells 10/27/2025

289: Finding a Better Way To Build Wealth and Cash Flow with Jon Wells On this week's episode, Jonathan welcomes Jon Wells, a real estate matchmaker, syndicator, and longtime realtor with A Better Way Realty and managing partner at Alpha Network—for a candid look at what actually builds durable wealth. Jon traces his journey from early “fix-and-flips” to higher-conviction “fix-and-holds,” and ultimately to group homes leased on commercial-style terms. He explains why patience, operator quality, and underwriting discipline matter more than shiny objects, and how aligning with the right partners turns headaches into hands-off income. As the conversation unfolds, they unpack contractor pitfalls, slim-margin flips that turn into flops and the relief of triple-net-style leases where the business, not the landlord, handles the day-to-day. Jon shares why he prefers renting large, lightly modified homes to sober-living/mental-health operators (versus carving up houses), why meeting new operators is the hardest part of this niche, and how option agreements can create shared upside. They also dive into passive vs. active choices, due-diligence checklists for syndications, and the value of investing in what you truly understand. Listeners will come away with a calmer, longer-term lens: start with who you trust, de-risk with questions that reveal how an operator thinks, and don’t mistake speed for progress—especially when cash flow and sleep-at-night returns are the goal. In this episode, you will hear: Why slim margins turn flips into long, stressful holds—and how to avoid it. The group-home model Jon uses: bigger homes, egress and safety upgrades, and commercial-style leases to vetted operators. Triple-net thinking for residential assets: fewer calls, clearer responsibility, steadier income. Trust and due diligence: the questions that de-risk syndications and funds—and when “no answer” means “no deal.” Why investing in what you actually know (and who you truly trust) beats chasing neon “opportunities.” How to choose between passive and active plays based on temperament, skills, and season of life. 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 Jon Wells Website - Facebook - Instagram - Linkedin - Connect with Jonathan: Website - YouTube - Instagram - Instagram - Zillow - j Bigger Pockets - Facebook - Email - This episode was produced by /episode/index/show/02c30127-f3cd-49a5-9336-8cd46bd05006/id/38764650

Zen and the Art of Real Estate Investing

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