Zen and the Art of Real Estate Investing

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with 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 rent...

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 capita...

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 w...

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 invest...

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 sh...

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 HU...

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...

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 neighborh...

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. T...

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 ac...

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 f...

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 retent...

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...

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 electrific...

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, structuri...

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 rea...

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...

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 t...

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, phi...

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 le...

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-...

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 communitie...

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...

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 wh...

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...