In this episode of Zen and the Art of Real Estate Investing, Jonathan is joined by Gary Lipsky, founder of Break of Day Capital, to explore what it takes to succeed in multifamily real estate syndication. Gary shares how he went from buying his first fixer-upper in Los Angeles to managing over 3,200 apartment units across Arizona. With an emphasis on transparency, due diligence, and investor education, Gary discusses how his firm evaluates markets, selects value-add properties, and builds long-term relationships with investors.

They dive deep into the differences between Class A and B assets, what makes a market like Tucson attractive for syndicators, and how Gary’s entrepreneurial background helped him scale while staying focused. The conversation also covers how passive investors should evaluate operators, what strong communication looks like, and why a conservative, consistent approach beats chasing the highest returns.

In this episode, you will hear:

• What drew Gary to the Tucson market, and how he evaluates its long-term potential

• Key indicators he looks for when assessing Class B value-add properties

• Traits of trustworthy syndicators and how passive investors can vet them effectively

• The role of conservative underwriting in building a sustainable investment strategy

• How consistent execution and strong communication help operators earn investor confidence

• Ways to educate potential investors without overselling or overpromising

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Supporting Resources:

Break of Day Capital website - breakofdaycapital.com

Break of Day Capital on YouTube - www.youtube.com/c/BreakofDayCapital

Break of Day Capital’s Facebook - www.facebook.com/breakofdaycapitalinvesting

Gary Lipsky on Instagram - www.instagram.com/breakofdaycapital

Connect with Gary Lipsky on LinkedIn - www.linkedin.com/in/gary-lipsky

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.

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Patrick Grimes, founder of Passive Investing Mastery and Invest on Main Street. Patrick shares how a painful first deal during the 2008 crash reshaped his investing mindset, leading him to focus on long-term wealth accumulation, cash flow, and true portfolio diversification. What began with single-family rentals eventually expanded into large multifamily syndications, recession-resilient markets, and alternative assets, including litigation finance and debt funds.

Patrick walks listeners through how he helps investors build a balanced portfolio by spreading risk across multiple, non-correlated asset classes. He also highlights why active professionals don’t need to become landlords to grow wealth, and how the right mix of passive investments can lead to financial security and freedom.

If you want to diversify beyond traditional real estate while keeping property in your portfolio, this episode is packed with practical strategies and new perspectives.

In this episode, you will hear:

• The early investment mistake that shaped Patrick’s long-term approach to wealth building

• What makes multifamily syndications a powerful tool for scalable, passive income

• Where litigation finance fits into a diversified real estate investment portfolio

• Ways debt funds provide stable returns outside of traditional equity deals

• Differences between passive and active investing for busy professionals

• The role of education and networking in avoiding common investor pitfalls

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

Passive Investing Mastery website - passiveinvestingmastery.com

Passive Investing Mastery on Facebook - www.facebook.com/PassiveInvestingMastery

Connect with Patrick Grimes on LinkedIn - www.linkedin.com/in/patricksgrimes

Invest on Main Street website - investonmainstreet.com

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.

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Jessie Lang, founder of Unlocked Rentals and author of “Rentals Made Easy,” to explore her journey from a $92,000 condo to a self-managed 70+ unit portfolio. Jessie shares how she unknowingly began house hacking out of necessity, transitioned into full-time investing, and eventually found her stride using the BRRRR method and private money.

From Craigslist roommates and DIY renovations to managing properties remotely and building a team, Jessie reveals how she scaled her business without skipping the hard work. She discusses the power of meetups, mentorship, and trusting your instincts, especially when the traditional path doesn’t fit. Jessie also talks about her mastermind community, the launch of her new book, and why she still prefers single-family rentals over multifamily deals.

This episode is a must-listen for investors looking to grow with intention, learn how to self-manage successfully, and avoid common pitfalls on the way to financial freedom.

In this episode, you will hear:

• How Jessie Lang went from living with roommates to profiting from rentals before she saw herself as an investor

• Why house hacking and the BRRRR method became her foundation for growth

• The turning point that led her to leave her W-2 and go all in on real estate

• The benefits of single-family rentals, tenant retention, and pet-friendly properties

• How she self-manages remotely, builds systems, and trains her team

• What inspired her to launch a mastermind and write “Rentals Made Easy”

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

https://unlockedrentals.com/

https://www.youtube.com/@unlockedrentals

https://www.instagram.com/jessielangofficial

https://www.linkedin.com/in/jessie-lang-36880637/

https://a.co/d/hAegcXI

https://urlgeni.us/facebook/unlockedguide

https://www.unlockedrentals.com/minicourseoptin

https://www.tiktok.com/@jessielangofficial

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.

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Jonah Bamberger, managing partner and executive chairman of Aulder Capital. Jonah shares the full arc of his real estate journey—from early value-add deals in Brooklyn to large-scale multifamily, hospitality, and international development in Portugal.

What began as a side project with a friend quickly became a full-time business as the duo capitalized on post-2008 opportunities. Jonah dives into how Aulder Capital adapts to shifting markets, navigates regulatory hurdles, and chooses when to pivot between markets, asset classes, and hold periods. He also talks about the realities of managing thousands of units, dealing with difficult tenants, and maintaining high performance while still aiming to make a positive community impact.

Whether you're an active investor, passive LP, or someone exploring international real estate, this episode offers a real-world perspective on how to scale with discipline and intention.

In this episode, you will hear:

• How Jonah got started in Brooklyn with rent-stabilized, value-add multifamily deals

• Why Aulder Capital expanded from New York to the Southeast, Midwest, and even Portugal

• The pros and cons of holding vs. flipping, and how market conditions drive those decisions

• What it really takes to manage thousands of units and stay mission-focused

• How syndications allow newer investors to get exposure without the management stress

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

Aulder Capital website - aulder.com

Aulder Capital on YouTube - www.youtube.com/@AulderCapital

Find Aulder Capital on Instagram - www.instagram.com/auldercapital

Connect with Aulder Capital on LinkedIn - www.linkedin.com/company/aulder-capital-llc

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.

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Ben Carmona, Managing Partner at Perch Wealth, to break down the mechanics and opportunities of the 1031 exchange. With over two decades of experience, Ben clarifies a complex process that can intimidate even seasoned investors. He shares how real estate owners, especially those nearing retirement, can defer taxes, move into passive income streams, and preserve wealth through tools like the Delaware Statutory Trust (DST).

Jonathan and Ben cover everything from early planning to misconceptions about like-kind exchanges. They also explore how investors can use 1031s to scale smarter, reduce active management headaches, and take advantage of private equity-style syndications.

Whether you're a baby boomer ready to slow down or a younger investor exploring long-term tax strategy, this episode will help you see 1031s and DSTs in a whole new light.

In this episode, you will hear:

• What a 1031 exchange is and how it helps defer taxes

• How Delaware Statutory Trusts (DSTs) enable passive investing with 1031 proceeds

• The importance of early planning and working with real estate-focused advisors

• How to avoid common mistakes like mishandling funds or missing deadlines

• Why syndications and diversification matter for today’s investors

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

Perch Wealth website - www.perchwealth.com

Perch Wealth on Youtube - www.youtube.com/@perchwealth

Find Perch Wealth on Facebook - www.facebook.com/perchwealth

Perch Wealth’s Instagram - www.instagram.com/perchwealth

Connect with Perch Wealth on Linkedin - www.linkedin.com/company/perch-wealth

Perch Wealth on X - x.com/perchwealth

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.

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Laura Navaquin—a mother, entrepreneur, and real estate investor who built her portfolio from the ground up alongside her husband. Starting with a credit card-funded mentorship and no prior experience, Laura began wholesaling in New Jersey and eventually scaled their portfolio to over 20 doors across six states.

Laura shares her evolution from side hustler to full-time investor, revealing how consistency, networking, and creative financing became the pillars of their growth. She breaks down the realities of managing a diverse real estate portfolio, the learning curve of self-management, and the challenges of rapid expansion. Laura also opens up about her shift in priorities—from corporate success to financial freedom and time with family—and how her mindset helped her embrace uncertainty.

Whether you're just starting or looking to scale your investments, this episode offers a real-world look at how strategic action and steady effort can build something meaningful over time.

In this episode, you will hear:

• Wholesaling can be a great entry point, but it takes hustle and realistic expectations

• Investing in mentorship is really an investment in yourself

• Scaling quickly is exciting, but evaluating portfolio performance is essential for long-term success

• Creative financing and networking for unlocking deals that traditional methods can't

• Defining your version of success and staying consistent

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

Supporting Resources:

Laura Navaquin’s website - lauranavaquin.com

Find Laura on Instagram - www.instagram.com/lauranavaquin

Connect with Laura on LinkedIn - www.linkedin.com/in/lauranavaquin

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.