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.

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.

Home inspections have come a long way from paper, pencils, and a few photos. Today, inspectors can use AI, thermal imaging, sewer cameras, air quality testing, and even robotic crawlers to learn more about a property before a buyer makes one of the biggest purchases of their life.

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce talks with Chris Ontiveros, owner of West Coast Property Inspections. Chris has worked in the home inspection business since 2007 and serves clients throughout Monterey, Santa Cruz, San Benito, and Santa Clara counties.

Chris explains how technology is changing his industry. His inspection software can use AI to help identify unfamiliar components from a photo and provide information that can be added to an inspection report. But Chris makes an important point: technology is a tool, not a replacement for an experienced inspector. He still reviews every report carefully before sending it to a client.

Chris also shares how inspections have expanded beyond the traditional property inspection. His company offers sewer scopes, thermal imaging, mold and air quality testing, and works with other professionals for services such as termite and roofing inspections. When inspectors cannot physically access a crawl space, specialized crawlers can even help them see underneath a home.

Documentation is another important part of Chris's approach. His inspections can include more than 200 photos so clients who cannot attend the inspection can still see what the inspector saw.

Chris also tells a memorable story that shows why inspections matter. During an inspection of a newer foreclosure property, he noticed plumbing fixtures backing up. Further investigation revealed that concrete had been poured into the home's plumbing. The potential repair involved portions of the foundation and plumbing system and was estimated at more than $100,000.

The lesson is simple: even a home that looks new can hide serious problems.

Chris and Bruce also discuss commercial inspections, mold testing, common electrical, plumbing, HVAC and roofing concerns, and how the inspection industry continues to evolve.

What can you learn from analyzing more than $1 billion worth of real estate deals?

In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce talks with multifamily investor Hayden Duer about how hands-on property management, disciplined underwriting, and hundreds of deal reviews have shaped the way Hayden invests.

Hayden grew up around real estate, but he did not start at the top. After college, he took his father’s advice to learn the business from the ground up. He started in apartment maintenance, then moved into leasing, assistant management, and eventually property management. At one point, he was managing apartment communities with 150 to more than 250 units.

That experience became the foundation for his investment strategy.

Today, Hayden and his partner focus on multifamily properties, primarily in markets such as Kansas City, Missouri, and Tucson, Arizona. They look for value-add opportunities where better management and operations can improve a property without requiring major changes to expensive building systems.

Hayden explains why his team typically targets properties built in the 1980s or later and why the 40-to-120-unit range fits their current strategy.

He also shares an impressive milestone: Hayden and his partner have analyzed more than $1 billion in real estate deals. Tracking and underwriting so many opportunities has helped them see how markets change and become more selective about the properties they pursue.

Bruce and Hayden also discuss how Hayden approaches renovations, financing, occupancy, property management, and investor capital. Hayden explains why relationships with sellers, brokers, property managers, and lenders can be just as important as the numbers behind a deal.

They also discuss Hayden’s growing use of AI. He is using AI to help streamline underwriting and due diligence, reducing time spent on repetitive data work.

Hayden’s long-term plans are ambitious. After closing the property that was under contract at the time of the interview, his portfolio would be just under 150 units. His goal is to reach 500 units within the next two years and eventually grow to between 3,000 and 5,000 units over the next decade.

Throughout the conversation, one theme stands out: Hayden believes in learning by doing. From apartment maintenance to analyzing $1 billion in potential deals, each step has helped shape the investor he is today.

Hayden is active on LinkedIn and welcomes people interested in connecting with him.

Email: haydenduer@gmail.com

Hayden also provided a business email and company website during the interview; because their spelling is unclear in the raw transcript, they should be confirmed before publication.

What does today’s commercial real estate market look like from the desk of a mortgage broker who is still getting deals done?

Bruce Bean welcomes Daria Walker back to SF Commercial Property Conversations for a wide-ranging conversation about commercial real estate, mortgage brokerage, and what she is seeing across California.

Daria shares how she has continued closing deals in a challenging market, including industrial properties, multifamily transactions, portfolio repositionings, and even a mobile home park. She discusses roughly $30 million in Bay Area multifamily business from the past year and explains why investors are looking beyond traditional opportunities to find returns that make sense.

Bruce and Daria take a close look at Oakland and the changes taking place in the East Bay. Daria discusses property values, rents, new ownership, adaptive reuse, small businesses, and why she believes Oakland has an opportunity to regain momentum.

The conversation then moves south to Los Angeles, where Daria describes a very different commercial real estate environment. She explains why smaller transactions are still happening while many middle-market deals remain on hold. She also discusses Measure ULA, rent restrictions, office values, institutional capital, and why today's market may create opportunities for smaller investors and business owners who want to own their buildings.

Daria also shares an interesting observation about the current market: some very small deals and very large deals are getting completed, while much of the middle of the market is sitting on the sidelines.

Outside of real estate, Daria has taken on another challenge: amateur boxing. She tells Bruce about training every day for an upcoming fundraising fight and why she is taking the competition just as seriously as she takes her career.

Daria brings experience, energy, and a dealmaker's perspective to a conversation about where California commercial real estate has been—and where opportunities may be emerging next.

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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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What does it take to build a successful real estate brokerage in one of the country's most competitive markets? In this episode of SF Commercial Property Conversations with Bruce Bean, Sean Chen shares how a commitment to service, leadership, consistency, and technology has helped him grow one of Silicon Valley's fastest-growing real estate teams.

Originally from China, Sean discusses his journey from studying medicine at NYU to entrepreneurship, the tech industry, and ultimately building a thriving real estate career in Silicon Valley. He explains why real estate is fundamentally a service business—not a sales business—and why discipline and daily prospecting are essential for long-term success.

Bruce and Sean also discuss how new agents can build meaningful client relationships, why providing value is more effective than traditional sales tactics, and how personalized coaching helps agents reach their individual goals.

The conversation also explores the rapid growth of Gaia Realty, the meaning behind the company's name, and how Sean and his leadership team are integrating artificial intelligence into nearly every aspect of their brokerage—from client presentations and comparative market analyses to listing preparation and agent productivity.

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What if property owners could eliminate late-night maintenance calls without paying for full-service property management? In this episode of SF Commercial Property Conversations with Bruce Bean, Bruce sits down with entrepreneur Hunter Drost, founder of OneTenant, to discuss how technology, AI, and a concierge-style maintenance service are changing the way rental properties are managed.

Hunter shares how his own frustrations as a real estate investor inspired him to build OneTenant—a platform designed to help independent property owners protect their investments while improving the tenant experience. Rather than replacing people with artificial intelligence, Hunter explains how AI can organize information, identify maintenance trends, and help property owners make smarter decisions while keeping experienced professionals involved every step of the way.

Bruce and Hunter also discuss how OneTenant vets contractors, streamlines maintenance requests, and provides property owners with a simple subscription model that handles tenant maintenance issues around the clock. The conversation explores the company's careful expansion from Reno into Las Vegas and Hunter's long-term vision of bringing the platform to markets across the country.

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