In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Gary Lipsky, founder of Break of Day Capital, to talk about syndication strategy, investor trust, and scaling a real estate portfolio without cutting corners. With over 3,200 apartment units under management, Gary shares the core principles that guide his team—and why transparency, focus, and smart market selection are key to long-term success.
Why Tucson and Class B Assets Make Sense
Gary has developed a focused approach to market selection, and Tucson stands out for its population growth, affordability, and strong rental demand. Unlike investors who jump from hot market to hot market, Gary’s strategy is built on consistency and a deep understanding of specific submarkets. His team targets Class B, value-add properties—assets that offer room for improvement without the competition and pricing of Class A buildings.
These properties appeal to renters seeking affordability without sacrificing quality and allow syndicators to force appreciation through renovations and improved management.
What Passive Investors Should Look For
For those investing in syndications passively, Gary emphasizes knowing who you’re investing with, not just what you’re investing in. Investors should pay attention to:
- An operator’s communication style and responsiveness
- Whether the underwriting is conservative and realistic
- The track record of actual performance, not just projections
- A clear, repeatable process for sourcing, renovating, and managing properties
Gary believes that flashy returns and overly aggressive assumptions are red flags. Instead, he advises investors to prioritize relationships and long-term results.
Scaling With Focus, Not Frenzy
Rather than chasing rapid expansion, Gary built Break of Day Capital by staying focused on what works. He shares how staying within a tight investment box allowed him to create repeatable systems and grow with intention. This steady approach has led to a portfolio that performs well and maintains investor trust, even in shifting market conditions.
Educating Investors Without the Hype
One of Gary’s goals is to make real estate syndication more accessible. Through his podcast, The Real Estate Investor Podcast, and his book “Invest Smart,” he breaks down complex investing topics in an approachable way for professionals looking to diversify outside the stock market. He encourages education, not sales pressure—especially for those just starting.
Key Takeaways
- Focused markets and asset classes lead to scalable, consistent results.
- Trust in syndication starts with honest underwriting and clear communication.
- Class B multifamily properties offer strong value-add opportunities.
- Passive investors should vet people, not just deals.
- Growth comes from discipline, not chasing trends.
Gary’s story is a great reminder that real estate success doesn’t have to be loud—it just has to be consistent.
If you want to learn more about Zen and the Art of Real Estate Investing Podcast, check out https://zenandtheartofrealestateinvesting.com/podcast/246/.