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.

Connect with Bob:

Website: http://aspenfunds.us/

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

LinkedIn: https://www.linkedin.com/in/bobfraser10/

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 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.

• 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.

Connect with Greg

Website: http://thecbcteam.com/

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

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 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.

• 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.

Connect with Joel:

Website: http://www.brrrr.com/

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

Facebook: https://www.facebook.com/brrrrloans/

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

Instagram: https://www.instagram.com/joelbrrrr/?hl=en

LinkedIn: https://www.linkedin.com/in/joel-kraut/

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

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 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.