Build Community-Driven Real Estate Ventures with Ryan Andrew

In this episode of the DealQuest Podcast, I'm thrilled to welcome Ryan Andrew, owner and CFO of Hiatus Homes, a real estate developer based in Bend, Oregon that specializes in small scale development and cottage cluster neighborhoods. Ryan has created an innovative approach to real estate development that delivers attainable by design housing for small households, with homes ranging from 500 to 1,000 square feet aimed at one to two person households.

Ryan also created the Hiatus Capital Fund to skip institutional investors and private equity funds, instead raising capital directly from local grassroots investors for local real estate developments. In 2024, he attempted to take this model to the next level as part of a community-based bid to buy the local ski resort, Mount Bachelor, from its corporate owner.

Currently, Ryan and Hiatus Homes work in partnership with small developers all over the country to bring attainable by design cottage projects to these communities and fund the projects through local investors. With 18 years of finance experience and a background as an entrepreneur in tech, real estate and investment management, Ryan brings a unique perspective to community-driven development.

EARLY EXPOSURE TO REAL ESTATE SHAPED LONG-TERM VISION


Unlike many real estate developers who find their way to the industry through various career paths, Ryan knew what he wanted to do from childhood. Growing up in Southern California during the late eighties and nineties, he watched extensive development happen around him and became fascinated by the building process.

"My parents were doing fix and flips when I was a kid. And so I spent a lot of time at fix and flips that they were working on, on the weekends," Ryan explains. "I'd either be like playing Legos in the bedroom and everything, but I got to work with my dad and my mom, and they let me paint stuff. Sometimes I got to use the hammer and smash drywall, and I thought it was really fun and really tangible."

This early hands-on experience created a lasting appreciation for the tangible nature of real estate development. Even as a child, Ryan understood that buildings were more than just structures - they were the foundation of communities and economic activity.

FINANCIAL CRISIS DETOUR BUILT ESSENTIAL SKILLS

Despite knowing his career direction early, Ryan graduated college in 2007 right at the beginning of the global financial crisis. With real estate development jobs virtually nonexistent, he took a position at PIMCO doing bond management, which felt disconnected from his passion for creating tangible assets.

"The whole time I was like, what is a bond? I mean, this is like, it's so esoteric. It's just a number on a, you know, in a Bloomberg terminal or in a spreadsheet," Ryan recalls. "And, calculating duration and cash flows did not make the same senses to me as construction and actually like creating something that was real."

However, this detour proved invaluable when he later returned to real estate. The financial experience taught him how to manage other people's money and understand complex investment structures - skills that became central to his innovative approach to real estate development.

CLOUDSTREET EXPERIENCE UNLOCKED REGULATORY KNOWLEDGE

Ryan's path back to real estate came through joining CrowdStreet, an early-stage company leveraging the Jobs Act to raise capital online for real estate deals. This experience gave him front-row access to new rules under Regulation D offerings that few people in the United States understood at the time.

"I mean, we were on the phone with the attorneys that had helped write the legislation. To have them help interpret how this goes for us," Ryan explains. "And like, I had access to these guys and so I got a front row seat to the revolution of the jobs act where all of a sudden instead of deals going, being done in back rooms with cigars, with people, you know, as they had been from, you know, the 1930s post great Depression."

This regulatory knowledge became the foundation for Ryan's later success in raising local capital directly from community investors, bypassing traditional institutional funding sources. Understanding how to structure offerings under the new regulations gave him a competitive advantage that few developers possessed.

LOCAL CAPITAL CREATES STRONGER COMMUNITY CONNECTIONS

The Hiatus Capital Fund represents a systematic approach to community-driven real estate development. Rather than seeking capital from institutional investors or private equity funds, Ryan raises money from local investors who have a vested interest in their community's development.

"We've had investors showing up at city council meetings, advocating for the projects, and giving public testimony," Ryan shares. "And like, it gives you a really different kind of investor. They come out and they look at our projects all the time. We get coffee a couple times a year. They all know us. They all trust us."

This approach creates multiple benefits: it removes the stigma of outside developers extracting profits from the community, provides patient capital from people who understand local market dynamics, and generates community support for projects. The fund has raised $8 million in equity, with 80% coming from local investors, to develop approximately $80 million in real estate projects.

SMALL HOMES ADDRESS GROWING MARKET DEMAND

Hiatus Homes focuses on building small homes (500-1,000 square feet) designed for one to two person households, a market segment that represents the fastest growing household formation component in the United States. Single person households now represent 29% of all households, up from the low twenties percentage just 10-15 years ago.

"Single person households is the fastest growing household formation component of, in the United States, it's now 29% of all households," Ryan explains. "They either have to like buy a three bedroom home in the suburbs where every trip's gonna be a car trip and it's gonna be harder to build community. And those homes are unattainable by design, so they might need another unrelated adult roommate."

The cottage cluster approach provides an alternative: private small homes within community-oriented developments that include shared amenities like community fire pits and gardens. This design philosophy creates opportunities for residents to have both privacy and community connection, addressing a real need in the housing market.

INVESTOR RELATIONS REQUIRES PROACTIVE COMMUNICATION

Managing dozens of local investors requires systematic communication and relationship management. Ryan has developed specific strategies for maintaining investor confidence and addressing concerns before they become problems.

"Communication, getting ahead of the communication is number one, bad news. Fast is number two," Ryan emphasizes. He writes detailed investor letters every 60-75 days that include project updates, photos, and macro-economic analysis related to the housing market.

The investor letters serve multiple purposes: they keep investors informed about project progress, demonstrate expertise through market analysis, and build trust through transparency. When projects face challenges, Ryan delivers bad news quickly and honestly, often including multiple scenarios for resolution. This approach has helped maintain investor confidence even during difficult periods like the interest rate environment of recent years.

SCALING THROUGH DEVELOPER PARTNERSHIPS

Rather than expanding geographically by hiring employees in new markets, Ryan has developed a partnership model that works with local developers across the country. This approach leverages local knowledge while providing design expertise and capital raising support.

"It's not us hiring a W2 employee in Fort Worth. It is. Somebody that's all, that's like a, you know, a developer or an aspiring developer that wants a more experienced group to come alongside them," Ryan explains.

The partnership structure varies based on each project's specifics, but typically involves Hiatus providing designs, permitting support, capital raising assistance, and ongoing project management. Local partners provide market knowledge, regulatory relationships, and boots-on-the-ground execution. This model allows for rapid scaling while maintaining the local community focus that makes the approach successful.

REGULATORY FLEXIBILITY CREATES OPPORTUNITIES

Many communities lack specific zoning for cottage cluster developments, but Ryan has found this creates opportunities rather than obstacles. Small communities often prove willing to adapt their building codes when presented with housing types that meet local needs.

"There is so much demand in so many communities that they're willing to pass, conditional use, permits, change, zoning, change, building code," Ryan notes. When communities see the benefits of attainable housing designed for small households, they often work with developers to create appropriate regulatory frameworks.

This flexibility extends to communities creating their own cottage codes and zoning adjustments. Ryan envisions eventually creating a standardized playbook that cities could adopt to implement attainable by design housing, making it easier for communities nationwide to embrace this development approach.

MOUNT BACHELOR BID DEMONSTRATED COMMUNITY POWER

Ryan's attempt to organize a community purchase of Mount Bachelor ski resort illustrates the potential scale of grassroots capital raising. Within 24 hours of announcing the initiative, the group received 2,000 emails from potential investors, including people willing to write eight-figure checks.

"I think we could have raised around a hundred million in equity to buy the mountain. And I think we could have gotten another, like, 50, 60 million in debt. And, would've paid, 150 million to buy the mountain," Ryan reflects.

While the bid ultimately didn't succeed because the seller chose not to engage, the experience proved that communities can mobilize significant capital when they care about local assets. The initiative also generated national media attention, including coverage from the New York Times, demonstrating the appeal of community ownership models.

This experience reinforced Ryan's belief that there's a broader trend toward community-driven ownership as people seek alternatives to large corporate conglomerates. The initiative showed how democratic capital raising can challenge traditional ownership structures, even for major recreational assets.

Tune in to this episode to hear Ryan Andrew share his systematic approach to community-driven real estate development. From navigating regulatory frameworks to managing dozens of local investors, this conversation offers actionable insights for any developer looking to build stronger community connections while creating profitable projects.

The strategies Ryan discusses align well with what Joel Miller shared in our episode about local real estate investing networks and Herman Dolce's insights on alternative capital sources for business growth.

• • • Listen to the full DealQuest Podcast episode here • • •

FOR MORE ON RYAN ANDREW
Ryan Andrew's LinkedIn
Hiatus Homes
Email: [email protected]

FOR MORE ON COREY KUPFER

Corey Kupfer's LinkedIn
Corey Kupfer's Website

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!