Jason Milton

CEO | Custom Capital

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.
His success caught the attention of a Middle Eastern billionaire, who recruited Jason to Dubai to lead sales for his $2B per year mixed-use commercial real estate firm that was named Forbes’ Growth Champion for the fastest-growing company on Earth. Before Jason came on board, the company’s sales were slumping and Jason’s job was simple — Return the firm to their hypergrowth status in selling brands like Versace Casa, Fendi Casa, Roberto Cavalli Home and Trump International Golf Course & Resort. During his tenure oversaw 300%+ revenue growth, helping scale the organization into a global real estate powerhouse and was promoted to oversee 2 continents (Europe & Asia). Eager to return home to the States, Jason geared up for his next chapter — and this time, it was personal. When his childhood best friend Patrick Truhlar sold his insurance brokerage for eight figures, the two reunited to build something different: a real estate investment firm with a conscience. Disenchanted by what they saw in the market in their own wealth building journeys, they launched the commercial real estate division of Patrick’s private family office — now known as Custom Capital.
Our mission was clear. Create a one-of-a-kind commercial real estate firm that removes all the barriers to entry for investors. A CRE one stop shop. One that empowers investors to control their financial destiny with best in class deals, 100% ownership and zero landlord responsibilities. Today, as CEO of Custom Capital, Jason has helped clients acquire and sell over $500 million of stabilized, cash-flowing commercial properties in just three years. He leads with the same intensity and integrity that defined his early career: relentless pursuit of excellence and a no-BS approach to value creation. Jason says: “There is no one in our parking space in the entire industry; we have disrupted the way CRE is done. Investors keep coming back over and over to purchase CRE. Essentially, we make commercial real estate easy, just the way we wanted it done for us; our team of 40 full time professionals are all proud of what we offer.”
Jason lives in Miami with his wife Valeria and his mother Carol. He is a long-time supporter of St. Jude’s Children’s Hospital and the ASPCA, and believes great businesses should be built not just for profit — but for people