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

Follow and Review:

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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.