Tom Gilbane, Co-President of Rockpoint, shares lessons from three decades of private equity—handshakes, home court advantage, and hard work. Tom Gilbane, Co-President of Rockpoint, reflects on a career that traces the evolution of modern real estate private equity—from Merrill Lynch and Westbrook Partners to building Rockpoint into one of today’s leading mid-market firms. Born into a family with deep construction roots, Tom learned early on the difference between a contractor’s 3% fee and a developer’s long-term stake. His career began on Wall Street during the REIT IPO boom of the 1990s before he joined Westbrook and later co-founded Rockpoint in 2003. Along the way, he helped shape a firm known for its focus on “address-level investing” and creating real estate entrepreneurs. [11:00] “You can’t market time, but you can definitely get things wrong.” Tom shares candid insights into cycles past and present—from the boom-and-bust of early opportunity funds to Rockpoint’s strategy of combining macro perspective with deeply local, micro-level execution. He reflects on home court advantage, why supply-demand-pricing power is the key to returns, and how operators have become just as important as capital in driving performance. [27:00] “There might be more equity for office than there is investible office, which sounds counterintuitive, but that’s the reality today.” From memorable deal stories like 299 Park Avenue to climbing Kilimanjaro with his 80-year-old father-in-law, Tom brings perspective, humor, and hard-earned wisdom about building teams, upholding a handshake culture, and playing the long game in real estate. Links Tom Gilbane | LinkedIn Rockpoint Website Rockhill Management Website