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.