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.