First-generation family offices face a fundamental challenge of how to preserve wealth built in one asset class while capturing growth opportunities across others without sacrificing stability for speculation.
Garrett Caplin, founder of Caplin Capital, has spent over a decade building a first-generation family office with more than $20 million in assets under management. According to Caplin, most family offices either remain too concentrated in their wealth-creation asset or diversify too quickly without maintaining the foundational strength that enabled growth.
“Real estate makes up about 80% of our portfolio, and for good reason,” says Caplin. “It provides predictable cash flow, tax advantages, and a hedge against inflation. That foundational strength allows us to take a steady, disciplined approach while funding longer-term investments in other asset classes.”
Maintaining a Strong Anchor in Real Estate
Real estate makes up about 80% of Caplin Capital’s portfolio, providing predictable cash flow, tax advantages, and an inflation hedge.
“At Caplin Capital, we focus on value-add opportunities across luxury short-term rentals and commercial assets,” Caplin explains. “We’re not just acquiring properties. We’re building equity through operational improvement and strategic repositioning.”
Most family offices face tension between preserving wealth in familiar asset classes and capturing growth in new opportunities. Concentrating too heavily on one asset limits upside. Diversifying too aggressively before establishing a stable cash flow forces selling winners to fund losers.
Maintaining a strong anchor addresses this by ensuring that 80% of the portfolio generates predictable cash flow to fund operations and provide capital for opportunistic investments. This allows taking longer-term views in private equity, private credit, and crypto without needing to liquidate positions during volatility.
“That foundational strength in real estate allows us to take a steady, disciplined approach while funding longer-term investments in other asset classes,” Caplin notes.
Expanding Through Intentional Diversification
Beyond real estate, Caplin Capital takes an intentional approach to diversification.
“In private equity, we acquire small and mid-sized service-based businesses with consistent profitability,” Caplin explains. “We help founders grow by integrating AI and modern systems to streamline operations.”
Most diversification occurs reactively, creating collections of disconnected investments rather than ecosystems where positions reinforce one another.
Intentional diversification means each asset class serves a specific purpose. Private equity focuses on acquiring service-based businesses with consistent profitability. Private credit provides flexible financing to real estate investors.
“In private credit, we provide flexible financing to real estate investors, offering creative solutions with little to no upfront capital,” Caplin notes. “This approach not only builds yield but creates value across our broader ecosystem.”
Partnering by Offering Strategic Support Beyond Capital
Caplin Capital invests in capital and offers flexible strategic support to founders, operators, and partners.
“Whether it’s through advisory, operational insight, or co-investment opportunities, our aim is to drive long-term value that extends far beyond the initial deal,” Caplin explains.
Most capital providers evaluate opportunities based on financial metrics, deploy capital, and monitor performance. This transactional approach misses opportunities to create value through operational support, strategic guidance, or ecosystem connections.
Caplin Capital partners differently by offering advisory support, helping founders navigate strategic decisions, operational insight from integrating AI and modern systems across portfolio companies, and co-investment opportunities where aligned incentives strengthen relationships.
“Our decisions are guided by long-term thinking, not short-term gains,” Caplin emphasizes. “We believe value creation is a shared process between us, our partners, and the communities we serve.”
Building Enduring Value Across Asset Classes
“At Caplin Capital, our mission is clear: to build enduring value across asset classes by combining strong fundamentals with forward-thinking strategy,” Caplin concludes.
Family offices that abandon their wealth-creation asset class too quickly lose stable cash flow, enabling patient capital deployment. Family offices that never diversify beyond their anchor remain overly concentrated with limited upside optionality.
Connect with Garrett Caplin on LinkedIn for insights on positioning family offices for long-term value creation.
