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.

What if a college campus could become a place to live for your whole life?

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce talks with Skylar Skikos, founder of Story in Place, about a fresh approach to real estate development. Skylar is working to turn places into communities where people can connect, learn, and build a meaningful life.

Skylar spent his first decade in real estate private equity and his second decade working on entrepreneurial hospitality ventures. He later served as a partner and head of development with Chip Conley’s Modern Elder Academy. In 2025, he started Story in Place, a boutique development studio focused on creating places with “stories worth living.”

A major focus of the conversation is Skylar’s idea of turning college campuses into intergenerational collegiate villages. Instead of separating students from everyone else, these communities could bring students, families, empty nesters, and other residents together.

Skylar shares details about a former college campus that Story in Place is reimagining. The plan includes clustered homes, a former chapel transformed into a library and community hub, a creative arts center, and a partnership with a micro-college that would bring an active student body and classes to the community.

Bruce and Skylar also discuss two residential projects in Northern California. In Sonoma, Skylar plans to build homes around a historic property that would become a neighborhood restaurant and gathering place. Another project in Sebastopol will use its location near parks, schools, trails, and downtown amenities to encourage a more connected and walkable way of life.

Throughout the conversation, Skylar explains why his hospitality background has shaped his approach to development. Instead of creating a great experience that lasts for only a weekend, he wants to bring some of the best parts of hospitality into everyday residential life.

They also talk about community involvement, density, traffic, parking, placemaking, human-scale development, and why listening to local residents early in the development process can lead to better projects.

What if AI could handle much of the busy work behind running a real estate business while giving people more time to focus on relationships, decisions, and growth?

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce talks with George Knowlton, founder of Tide360, about how artificial intelligence is changing real estate, asset management, property operations, and small business.

George shares how his background in general construction and asset management led him to AI. He explains how Tide360 uses AI “employees” to help with tasks such as answering emails, managing CRM activity, supporting marketing, researching information, reviewing projects, and helping underwrite real estate and construction opportunities.

George also introduces his SMILE philosophy: Safe, Moral, Inclusive, Linguistic, and Experiential. His goal is to encourage real estate professionals and asset managers to consider every stakeholder when making decisions, from investors and owners to workers and residents.

Bruce and George also explore where real estate may be headed next. George discusses his vision for blockchain-based real estate ownership, including ways residents and smaller investors could potentially own shares in properties. They also discuss how AI could change property management by helping handle maintenance requests, scheduling, follow-up, and other administrative work.

A major part of the conversation focuses on the relationship between AI and people. George does not see AI simply as a replacement for human employees. Instead, he believes AI can take over time-consuming administrative work so people can spend more time using the judgment, relationships, and human skills that matter most.

George also explains Tide360’s “Boardroom Vault,” which includes specialized AI roles designed to support areas such as executive administration, financial operations, leadership, performance, and legal research.

About George Knowlton

George Knowlton is the founder of Tide360 and an advocate for using AI to improve real estate, asset management, construction, and business operations. His work combines technology with his SMILE philosophy and a focus on helping businesses work more efficiently.

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