247: Going From Investor To Investor-Friendly Agent with Niyi Adewole
Zen and the Art of Real Estate Investing
Release Date: 06/02/2025
308: Empowering Intelligent Investors Through BRRRR Loans with Joel Kraut
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 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...
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307: Helping Real Estate Investors Win One Deal at a Time with Steve Afra
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 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...
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306: How To Invest Privately and Grow Strategically with Spencer Hilligoss
Zen and the Art of Real Estate Investing
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...
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305: How To Flip Your Story and Build Real Wealth with Brian Tran
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 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...
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304: The Case For Buying a Second Home First with Katie Cline
Zen and the Art of Real Estate Investing
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...
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303: Building Bold Brands For Your Short-Term Rental or Boutique Hotel with Steph Weber
Zen and the Art of Real Estate Investing
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...
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302: From Ranching To Real Estate Investing with Joe Rinderknecht
Zen and the Art of Real Estate Investing
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...
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301: Award-Winning Design for Commercial Real Estate with Marcy Sagel
Zen and the Art of Real Estate Investing
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...
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300: What You Need To Succeed as a Real Estate Investor in 2026
Zen and the Art of Real Estate Investing
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...
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299: Accelerating Access to EV Charging for Real Estate Portfolio Owners with Benjamin Kanner
Zen and the Art of Real Estate Investing
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...
info_outlineIn this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Niyi Adewole—real estate investor, short-term rental operator, and investor-friendly agent—to discuss the journey from first house hack to a thriving real estate business. Niyi shares how he transitioned from medical device sales to building a 30-unit portfolio in Louisville, Kentucky, before shifting into short-term rental management, new development, and becoming a trusted guide for other investors through his real estate team and podcast.
Jonathan and Niyi explore the realities of house hacking, the importance of building systems, and why consistency and a long-term outlook matter more than chasing quick wins. Niyi offers advice for new investors, from how to get started in a high-interest-rate environment to what to look for in a truly investor-friendly agent.
In this episode, you will hear:
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What led Niyi to house hacking, and how it helped him build early momentum
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Lessons learned from managing rentals, handling evictions, and scaling with systems
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How a move to Atlanta sparked a shift into full-time real estate entrepreneurship
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Tips for investors navigating short-term and mid-term rental strategies
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How to vet property managers and protect your cash flow
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The difference between a real estate agent who says they work with investors and one who actually does
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Supporting Resources:
Ekabo Home website - linktr.ee/ekabohome
Ekabo Home on YouTube - www.youtube.com/channel/UCo-iogGt9tlPsMDFKB7B-1Q
Ekabo Home’s Facebook page - www.facebook.com/groups/530839468550185
Ekabo Home on Instagram - www.instagram.com/ekabohome
Connect with Niyi Adewole on LinkedIn - www.linkedin.com/in/niyiadewole
Ekabo Home on TikTok - www.tiktok.com/@ekabohome
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
TikTok - www.tiktok.com/@trustgreene
Zillow - www.zillow.com/profile/StreamlinedReal
Bigger Pockets - www.biggerpockets.com/users/TrustGreene
Facebook - www.facebook.com/streamlinedproperties
Email - info@streamlined.properties
Episode Credits
If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.