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.

Connect with Steve

Website: https://thesteveafra.com/

Youtube: https://www.youtube.com/@afrasteve

Facebook: https://www.facebook.com/steve.afra.18

Instagram: https://www.instagram.com/thesteveafra

LinkedIn: https://www.linkedin.com/in/steveafra/

Website: https://nvestorfunding.com/

TikTok: https://www.tiktok.com/@afrasteve

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

Connect with Spencer

Website: http://www.madisoninvesting.com/

Website: http://www.spencerhilligoss.com/

Twitter: https://x.com/SpenceHilligoss

LinkedIn: http://www.linkedin.com/in/shilligoss/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

Connect with Brian

Website: http://mrbriantran.com/

Youtube: https://www.youtube.com/@Mr.BrianTran

TikTok: https://www.tiktok.com/@mrbriantran?lang=en

Instagram: https://www.instagram.com/mr.briantran/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

• 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

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.

Connect with Katie:

Website: http://buyyoursecondhomefirst.com/

Youtube: https://www.youtube.com/@SecondHomeFirst

Instagram: https://www.instagram.com/buyyoursecondhomefirst/

LinkedIn: https://www.linkedin.com/company/second-home-first/

Episode 216: https://zenandtheartofrealestateinvesting.com/podcast/216/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

• 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

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.

Connect with Steph:

Website: http://theweberco.com/

Instagram: http://instagram.com/theweberco

LinkedIn: https://www.linkedin.com/in/stephweberbrandcoach/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

• 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.

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.

Connect with Joe:

Website: https://cowboycapital.us/

Youtube: https://www.youtube.com/@cowboycapital.us2025

Facebook: http://facebook.com/joe.rinderknecht

Instagram: https://www.instagram.com/joe_rinder

LinkedIn: https://www.linkedin.com/in/joerinderknecht/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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.

• 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.

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.

Connect with Marcy:

Website: https://msainteriors.com/

Instagram: https://www.instagram.com/MSAInteriors

LinkedIn: https://www.linkedin.com/in/MarcySagel/

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.

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 - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio.