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.
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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 .
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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
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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
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288: Building a Capital Gains Tax Exit Plan with Brett Swarts
10/23/2025
288: Building a Capital Gains Tax Exit Plan with Brett Swarts
In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Brett Swarts, founder of Capital Gains Tax Solutions, to explore strategies for minimizing capital gains taxes when selling real estate or business assets. Brett Swarts is the founder of Capital Gains Tax Solutions, specializing in advanced strategies to help investors defer or eliminate capital gains taxes. With extensive experience in structuring Deferred Sales Trusts and other exit strategies, Brett has guided numerous real estate and business owners in building tax-efficient, long-term wealth plans. Brett explains how the Deferred Sales Trust (DST) offers a flexible alternative to traditional 1031 exchanges, providing investors with greater control over timing, liquidity, and investment choices while deferring taxes in a manner that is legally compliant under IRS guidelines. Brett outlines the mechanics of a DST, detailing how proceeds from a sale can be structured to defer capital gains taxes and reinvest in a variety of assets. You’ll get insight into the advantages of a DST over standard tax-deferral methods, including reduced pressure to time the market, expanded diversification opportunities, and the ability to preserve wealth across multiple investment vehicles. Jonathan and Brett also discuss common misconceptions about tax-deferred strategies, emphasizing the importance of understanding legal structures and working with experienced professionals. The conversation highlights how these tools can fit into a broader estate and legacy planning framework, ensuring that wealth is transferred efficiently to future generations while maintaining flexibility for investors today. Several real-world examples demonstrate how investors have effectively utilized DSTs to manage risk, maintain cash flow, and safeguard portfolio value in dynamic markets. Brett emphasizes that while a DST can benefit many investors, it is particularly effective for those with significant gains, complex portfolios, or long-term wealth preservation goals. The discussion concludes with actionable guidance on evaluating whether a DST aligns with an investor’s exit strategy and long-term financial objectives. By the end of this episode, you’ll understand how to approach capital gains tax planning strategically, integrating DSTs into their broader real estate and business investment strategies. Jonathan and Brett provide a clear framework for deferring taxes, diversifying holdings, and protecting wealth, enabling investors to make informed decisions that align with both their financial and personal objectives. In this episode, you will hear: How the Deferred Sales Trust works as an alternative to 1031 exchanges Ways to defer capital gains taxes while maintaining investment flexibility Strategies for diversifying proceeds and protecting portfolio value Common misconceptions about tax-deferred exit strategies How estate and legacy planning can integrate with a DST 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 . 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: Capital Gains Tax Solutions website - Build It To Billions on YouTube - Brett Swarts on Facebook - Brett’s Instagram - Connect with Brett on LinkedIn - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte
10/20/2025
287: Getting Rich Slowly By Investing In Real Estate Over a Lifetime with Luis Belmonte
In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Luis Belmonte, a lifelong real estate investor, to explore the lessons he’s learned over decades of investing in multifamily, industrial, and commercial real estate across the U.S. and internationally. Luis shares his early experiences, including navigating the complexities of San Francisco’s real estate market in the pre-MLS era, identifying overlooked investment opportunities, and managing properties during challenging economic cycles. His stories reveal how creativity, persistence, and relationship-building have been central to his long-term success. Luis takes us back to his first multifamily acquisitions, explaining the strategies he used to uncover deals when information was scarce. From attending broker meetings with nothing but a notebook and a case of beer to identifying opportunities through obituaries, Luis emphasizes the importance of proactive deal sourcing and building relationships with those who have local knowledge. He also discusses the transformative effect of San Francisco rent control, illustrating how strategic management and patience can yield extraordinary returns over time. The conversation then shifts to international real estate development, highlighting the stark contrasts between regulations and construction practices in countries like Mexico and Japan compared to the United States. Luis recounts overcoming challenges such as unclear land ownership, lack of infrastructure, and differing bidding practices, underscoring the value of understanding local systems and collaborating with trusted partners. Whether navigating city politics in San Francisco or creating operational solutions abroad, Luis demonstrates that preparation and local expertise dramatically reduce risk and unnecessary costs. Jonathan and Luis also examine the current economic landscape, including interest rates and cyclical market patterns. Luis offers perspective on borrowing, refinancing, and interest rate history, reinforcing that measured and disciplined investing remains key, regardless of market fluctuations. Finally, Luis shares his preferred asset classes for long-term wealth creation: multifamily and warehouse properties. He emphasizes the importance of choosing an investment style aligned with one’s personality, seeking downside protection, and understanding operational realities to maximize returns. You’ll come away with practical advice on building sustainable real estate wealth, managing risk, partnering effectively, and identifying investment opportunities that others might overlook. Luis’s guidance is grounded in decades of real-world experience, making this episode essential for both new and seasoned investors looking to grow their portfolios with confidence. In this episode, you will hear: How Luis sourced early San Francisco deals before online MLS existed Creative approaches to finding undervalued properties and motivated sellers The impact of rent control on long-term investment returns Lessons from international real estate development in Mexico and Japan Strategies for partnering, reducing risk, and avoiding “stupid taxes” Luis’ preferred asset classes for consistent long-term wealth How interest rate cycles affect real estate investing and financing 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 . 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: Seven Hills Properties website - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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286: Calculated Risk and Upsized Returns in Self Storage with Neil Henderson
10/16/2025
286: Calculated Risk and Upsized Returns in Self Storage with Neil Henderson
On today’s Zen and the Art of Real Estate Investing, Neil Henderson, investor relations specialist and general partner at Nomad Capital, joins Jonathan to share how he transitioned from Airbnb host to self-storage syndicator. His story begins with a guesthouse, an article from his mother about a new company called Airbnb, and a growing curiosity that led him down the BiggerPockets rabbit hole. Over time, that curiosity evolved into a career in self-storage, a niche known for stability, scalability, and smart value-add strategies. Neil and his partners at Nomad Capital have built a business that thrives on calculated risk. By focusing on conversions rather than new construction, they’ve lowered costs, created built-in equity, and shielded investors from some of the volatility affecting other commercial asset classes. In this episode, Neil explains how he built relationships that led to partnership opportunities, why networking changed the course of his career, and how Nomad’s integrated construction team creates a unique competitive advantage. From the early lessons of running short-term rentals to raising capital for syndications, Neil reveals what it takes to build a resilient investing mindset. He and Jonathan also discuss the fundamentals of self-storage investing, including the business’s recession resilience, demand drivers, and how technology has shifted operations and tenant expectations. Whether you’re exploring your first passive investment or considering a pivot into self-storage, this episode offers a clear view into one of real estate’s most durable and adaptive asset classes. In this episode, you will hear: The unexpected start that turned a Las Vegas guesthouse into Neil’s first investment property Lessons from scaling an Airbnb listing into a profitable business The power of genuine networking and building lasting partnerships in real estate How Nomad Capital uses conversions to create value and reduce risk Strategies that make self-storage recession-resilient and operationally efficient The mindset shifts that help investors manage risk and grow with confidence 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 . 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: Nomad Capital website - Truly Passive Income on YouTube - Truly Passive Income’s Facebook - Truly Passive Income on Instagram - Connect with Neil Henderson on LinkedIn - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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285: Creating and Understanding Your Short-Term Rental Buy Box with John Bianchi
10/13/2025
285: Creating and Understanding Your Short-Term Rental Buy Box with John Bianchi
In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes back John Bianchi, founder of STR Search and widely known as “The Airbnb Data Guy.” John specializes in data-driven short-term rental analysis, helping investors identify profitable properties that align with their personal and financial goals. Returning for his second appearance on the podcast, John and Jonathan dive into the evolving world of short-term rentals, discussing how to define your “buy box,” evaluate returns, and balance yield, appreciation, and tax advantages. Their conversation explores how every investor’s short-term rental strategy depends on their personal goals, whether it is generating cash flow, appreciation, or tax savings. John explains how STR Search tailors property searches to each client, analyzing data to match them with the right market and home. They discuss how operational excellence and guest experience can make or break a property’s performance, and why even the best data can’t replace curb appeal, hospitality, and local expertise. Jonathan and John also share stories from their own experiences, examining properties together, assessing markets like upstate New York and the Poconos, and learning how aesthetics, first impressions, and good operations drive long-term success. They delve into the creative aspects of short-term rentals, encompassing design and storytelling, as well as crafting unique guest experiences that encourage repeat bookings. By the end, John and Jonathan uncover the art of turning data into hospitality and the mindset needed to build lasting value in short-term rental investing. In this episode, you will hear: Defining your short-term rental “buy box” based on yield, appreciation, and tax priorities Understanding how personal goals shape your investment strategy The crucial role of curb appeal, neighborhood quality, and first impressions Why photography, design, and hospitality directly influence revenue Balancing data-driven property selection with local market expertise Avoiding costly tax-savings-only purchases and focusing on sustainable returns How operational discipline and creative design elevate guest experience The growing importance of storytelling and experiential stays in the STR space 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 . 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: STR Search website - John Bianchi’s YouTube channel - Find John on Instagram - Connect with John on LinkedIn - John’s TikTok - The Bianchi Method - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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284: Diverse Opportunities With Funds and Syndications For Long-Term Growth with Mike Zlotnik
10/09/2025
284: Diverse Opportunities With Funds and Syndications For Long-Term Growth with Mike Zlotnik
In today’s episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Mike Zlotnik, a real estate fund manager and the CEO of TF Management Group, who is widely known in the real estate investing community as “Big Mike.” With over two decades of experience in finance, technology, and real estate, Mike offers a clear and structured approach to helping investors understand how to diversify their portfolios, manage risk, and build long-term wealth through funds and syndications. Jonathan and Mike begin by discussing the fundamentals of how funds differ from single syndications and why investors might choose one vehicle over the other. Mike explains how funds offer built-in diversification across asset classes and geographies, while syndications allow investors to be more selective with specific deals. He emphasizes the importance of understanding an operator’s track record, the alignment of incentives, and the mechanics of preferred returns when evaluating any investment. The conversation moves into the role of debt, interest rate cycles, and how professional managers mitigate risks in uncertain economic environments. Mike provides real-world examples of how funds structure distributions, manage cash flow, and use conservative underwriting to protect investors’ capital. He also emphasizes the importance of tax efficiency, particularly in relation to depreciation and its impact on an investor’s overall returns. For listeners looking to grow their real estate portfolios, Mike highlights the strategic advantage of investing through funds that allow participation in multiple projects at once. He also explains how smaller investors can still access institutional-quality deals by leveraging fund structures managed by experienced operators. Throughout the episode, Jonathan pushes Mike to translate technical details into actionable takeaways that any investor can apply, making this conversation both approachable and highly informative. By the end of this discussion, listeners will come away with a stronger understanding of how to evaluate funds and syndications, the critical role of trust and alignment with operators, and the importance of long-term strategy in real estate investing. In this episode, you will hear: Diversification through funds versus deal-by-deal syndication The importance of operator track record and investor alignment How preferred returns and profit splits are structured Managing debt and interest rate cycles in uncertain markets Tax efficiency and the role of depreciation in returns Why funds give smaller investors access to larger opportunities The value of conservative underwriting and capital protection 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 . 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: Tempo Funding website - Tempo Funding on YouTube - Temp Funding’s Facebook - Connect with Tempo Funding on LinkedIn - Tempo Funding on X - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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283: Aligned Incentives In Vetted Multifamily Real Estate with Axel Ragnarsson
10/06/2025
283: Aligned Incentives In Vetted Multifamily Real Estate with Axel Ragnarsson
In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Axel Ragnarsson, Founder and Managing Partner of Aligned Real Estate Partners. Axel began his entrepreneurial journey by flipping cars in college, which eventually led him to real estate. Over the years, he built a personal portfolio of multifamily properties before expanding into syndication and capital raising. His focus is on acquiring Class B and C value-add multifamily properties, primarily in New Hampshire, with an emphasis on building lasting relationships and structuring deals that align incentives between operators and investors. Jonathan and Axel discuss the differences between transactional and relationship-driven investing, the challenges of scaling from small multifamily projects to larger ones, and why patience and consistency matter more than chasing exponential growth. Axel also explains how direct-to-seller strategies in multifamily differ from single-family approaches, how sellers often value ease and trust as much as price, and why creative deal structures can open doors that brokered deals never could. Their conversation underscores the importance of transparency, credibility, and long-term thinking in both acquisitions and raising capital from investors. If you’re interested in understanding how to grow a multifamily portfolio the right way —through relationships, alignment, and steady growth —this episode provides a roadmap for approaching real estate with integrity and strategy. In this episode, you will hear: Axel Ragnarsson’s progression from flipping cars to building an 80–90 unit multifamily portfolio Why he shifted from small self-owned deals to capital raising and syndications The mindset shift required for effective direct-to-seller outreach How relationship-building trumps transactional deal-making in multifamily investing The role of patience in scaling sustainably instead of chasing door counts Ways creative deal structures help unlock financing and opportunity Why aligned incentives between investors and operators are critical for long-term 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 . 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: Aligned Real Estate Partners website - Axel Ragnarsson’s Instagram - Connect with Axel on LinkedIn - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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282: Building Strategic Partnerships in Commercial Real Estate Investments with John Azar
10/02/2025
282: Building Strategic Partnerships in Commercial Real Estate Investments with John Azar
In this episode of Zen and the Art of Real Estate Investing, Jonathan Greene speaks with John Azar of Peak 15 Capital about the power of strategic partnerships in commercial real estate. John shares his experience in structuring co-GP deals, managing multifamily funds, and creating opportunities that enable investors to scale their portfolios while minimizing operational involvement. He emphasizes the importance of selecting the right partner, practicing conservative underwriting, and leveraging expertise to optimize long-term returns. John and Jonathan explore the benefits of fund investments versus individual syndications. John explains how a diversified “bin” of assets, such as multifamily properties, industrial properties, and car washes, provides stability, access to multiple cash flow streams, and peace of mind for investors seeking smart, passive income. They also discuss how fund structures offer investors tangible exposure to real estate assets while minimizing the need for active property management. The conversation highlights the tangible nature of real estate compared to stocks or bonds. Investors can visit properties, evaluate assets in person, and see the land and buildings they’re backing. This hands-on approach enables investors to make informed decisions, understand the true value of the assets, and trust their operators to execute effectively. Both Jonathan and John stress how real estate provides optionality and flexibility, making it a unique asset class for long-term wealth building. When evaluating deals, John emphasizes the importance of both people and numbers. Peak 15 Capital adopts a conservative underwriting approach, carefully analyzing rent growth, cap rates, and funding plans to avoid overly optimistic assumptions. John also notes the role of intuition and in-person meetings when selecting partners, advising investors to pass on deals that don’t feel right, even if the projected returns appear attractive. Finally, John introduces Peak 15 Capital’s multifamily accelerator course, which guides investors through every stage of multifamily investing, from identification and acquisition to management and disposition. The course blends Mom-and-Pop fundraising strategies with institutional-level insights, preparing investors to grow in the multifamily sector and scale their portfolios strategically. In this episode, you will hear: Starting in large scale development before moving into multifamily Advantages of diversified fund investments versus one-off syndications Lessons from the 2008 recession and relaunching in the southeast How real estate’s tangible nature provides confidence and flexibility for investors Key criteria for deal evaluation: assumptions, underwriting, and partner selection The benefits of co-GP structures for leveraging capital and control Importance of reserves and time in weathering market downturns How the Peak 15 Capital multifamily accelerator course prepares investors for full-cycle investing 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 . 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: Peak 15 Capital website - John Azar’s Instagram - Connect with John on LinkedIn - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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281: Securing Your New Life Abroad Using Expat Money with Mikkel Thorup
09/29/2025
281: Securing Your New Life Abroad Using Expat Money with Mikkel Thorup
In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Mikkel Thorup, founder and CEO of Expat Money, a consultancy helping clients navigate second residencies, international investments, and asset diversification. Known as one of the world’s most sought-after expat consultants, Mikkel has lived in nine countries over 25 years and built a portfolio of properties across ten nations. His work focuses on mitigating tax liabilities, creating Plan B options through residency and citizenship, and guiding investors toward secure and profitable opportunities abroad. Jonathan and Mikkel explore how global real estate investing intersects with lifestyle choices, risk mitigation, and long-term legacy planning. Mikkel shares how his early exposure to real estate through his family shaped his investment philosophy, why he avoids debt-heavy strategies, and how he structures group deals to reduce developer risk. He also breaks down the benefits of international diversification, not just in geography, but also in currencies, timelines, and property types. The conversation extends beyond investment mechanics to the lifestyle and generational advantages of expat living, including multi-citizenship for children, cultural exposure, and community building. Mikkel emphasizes the importance of boots-on-the-ground research, building trust with developers and governments, and striking a balance between adventure and security. This episode provides a roadmap for investors who want to align real estate with global mobility, family resilience, and financial independence. In this episode, you will hear: Mikkel’s journey from leaving school at 12 to becoming a leading global expat consultant The role of early family exposure to real estate in shaping his investment path Why he focuses on pre-construction and cash buying instead of debt-driven strategies How group purchasing reduces risk in international development projects The benefits of second residencies and citizenship as a long-term family legacy Currency diversification and geopolitical monitoring as part of global investing Structuring investments for both cash flow and capital appreciation abroad The importance of investor tours, trust, and seeing projects firsthand Top markets currently friendly to foreign investors: Costa Rica, Panama, and Paraguay 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 . 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: Expat Money website - Expat Money on YouTube - Expat Money’s Facebook - Find Expat Money on Instagram - Connect with Expat Money on LinkedIn - Expat Money on X - Expat Money Summit - Website - YouTube - Instagram - Instagram - TikTok - Zillow - Bigger Pockets - Facebook - Email - 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 Let them know we sent you.
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