Jason Milton, CEO and Co-Founder of Custom Capital, a Miami-based private family office that helps accredited investors acquire 100%-owned, cash-flowing commercial real estate joins Enterprise Radio.
Listen to interview with host Eric Dye & guest Jason Milton discuss the following:
- Your firm recently initiated a $100 million strategy focused exclusively on medical net-lease real estate. Could you explain the rationale behind targeting the medical sector at this specific time?
- Custom Capital identifies as a private family office rather than a traditional fund or syndication. How does this specific organizational structure provide a distinct advantage for an investor’s capital?
- By establishing direct ties with developers, you often secure opportunities before they reach the open market. Why is it beneficial for a developer to partner with you privately instead of pursuing a public listing?
- Operating out of Miami with a network of over 40 lenders, you manage a national portfolio. In today’s market, is physical location still a factor, or has the business become entirely dependent on the strength of one’s professional network?
- Finally, looking back at the deals you did in Custom Capital’s first year versus now, what’s something you believed about this business early on that turned out to be dead wrong?
Jason Milton’s career is the story of reinvention — from international fashion to record-breaking real estate growth, with one common thread: he’s the guy you call when something needs to be turned around. Jason got his start in the fast-paced fashion industry, working with global brands and living in cities like New York, Milan, Tokyo, and Barcelona. His early years were marked by relentless travel, high-pressure environments, and deep exposure to international business — an experience that taught him how to adapt quickly, communicate across cultures, and thrive in the world’s most competitive markets. Eventually, his appetite for challenge led him into a very different kind of business — the high-stakes world of vacation ownership. Jason joined Hilton Hotel’s first-ever urban timeshare division in Manhattan, where he became one of the firm’s top sellers. Within months, he was promoted, then promoted again. Over the next decade, Jason became Hilton and Starwood’s go-to turnaround leader, dropped into the lowest-performing resorts to rebuild, re-train, and revitalize sales operations. Under his leadership, teams consistently broke records — and Jason’s team drove over $750 million in new sales.
Website: customcapital.com…