Gary Lipsky: What Investors Get Wrong About Multifamily Syndications

Gary Lipsky: What Investors Get Wrong About Multifamily Syndications

A projected return can look great on paper. But Gary Lipsky says one of the biggest mistakes investors make is focusing on the numbers instead of the person running the deal.

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce talks with Gary Lipsky of Break of Day Capital about multifamily investing, syndications, asset management, and what investors should look for before putting money into a deal.

Gary shares how he moved from owning other businesses and investing in smaller real estate projects to buying a 44-unit property in Tucson for $1.65 million. Today, his group manages investments representing more than 1,600 units and has built a strong presence in the Arizona multifamily market.

Gary explains why his team stays focused on a small number of markets instead of chasing deals across the country. By constantly studying Phoenix, Tucson, and other Southwest markets, his team builds thousands of data points that help them recognize opportunities and move quickly when the right property appears.

Bruce and Gary also discuss one of the most important lessons Gary has learned as an investor: do your own due diligence.

Gary explains why investors can get into trouble when they chase projected IRRs or invest simply because a friend recommends a deal. He shares his own experience of investing without doing enough independent research and losing his investment. His advice is to look closely at the sponsor and operator, their systems, market experience, track record, and knowledge of the asset class.

The conversation also covers today’s multifamily market. Gary discusses higher cap rates, refinancing challenges, lender relationships, and why he believes current pricing is creating opportunities for buyers who have the capital and patience to invest.

Gary also shares how his team improves multifamily properties. Rather than relying only on expensive unit renovations, they may improve landscaping, pools, barbecue areas, dog parks, package lockers, staffing, and the overall resident experience.

Finally, Bruce and Gary explore how AI is beginning to change real estate operations. Gary’s team is using AI for communication, property analysis, identifying budget anomalies, leasing, maintenance requests, and tenant collections.

About Gary Lipsky

Gary Lipsky is a multifamily real estate investor and operator with Break of Day Capital. His team focuses heavily on Arizona and the Southwest and manages investments representing more than 1,600 multifamily units.

Gary is also the author of Best in Class, about multifamily asset management, and Invest Smart: Spotting Red Flags in Real Estate Syndications, which helps investors understand how to evaluate sponsors, operators, and syndication opportunities.