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.

Tom Gilbane | LinkedIn

Rockpoint Website

Rockhill Management Website

Diane Hoskins, Gensler’s Global Co-Chair, discusses the value of collaboration and why design can be the most powerful tool for shaping a better future.

Diane Hoskins, Global Co-Chair of global design firm Gensler, shares insights from leading a team of over 6,000 professionals across 53 offices worldwide—and why she believes intentional, collaborative design can be the most powerful tool for shaping a better future.

Diane shares Gensler’s research on how vibrant, adaptable cities can strengthen economic performance, attract investment, and improve quality of life. In her current leadership role at Gensler and her former role leading Urban Land Institute (ULI), Diane emphasizes that excellent urban solutions are never the work of one individual. 

[23:10] “We value collaboration and we call it this “one firm-firm” mindset, which is really the team has to win, not just you. . .   For us, it’s about the team winning, not just the individual. It shows up loudly.”

Diane reflects on how the pandemic accelerated changes already underway in the workplace and urban environments. She explains how forward-thinking companies are reimagining offices not as places of obligation, but as destinations that foster culture, creativity, and human connection.

[01:03:43] “The value [of design] is in creating places where people can connect with each other. . . this idea of single purpose zoning, single purpose buildings, feels less and less like what people are looking for—and value follows people and their experience.”

Whether you’re an investor, developer, or city leader, Diane’s perspective offers a roadmap for building spaces and communities that matter to people and the lives they want to live.

Links

Diane Hoskins | ⁠LinkedIn⁠

Gensler ⁠Website⁠

⁠Art’s Principles⁠ by Art Gensler

⁠Design for a Radically Changing World⁠ by Diane Hoskins and Andy Cohen

Urban Land Institute’s ⁠Website⁠

Nancy Lashine recaps standout moments so far this year from Season 3 and previews powerhouse guests shaping the future of Real Estate Capital.

Gunnar Branson, AFIRE’s CEO, explores the evolution of real estate, capital flows, and the power of emotional intelligence.

Devon Olson, former Director of Real Estate at Utah Retirement Systems, shares his successes and lessons learned over his 40-year tenure at Utah Retirement Systems.

Sara Queen, Managing Director and Head of Real Estate Equity at MetLife Investment Management, dives into leadership and value creation.

Keith Breslauer, founder and managing partner at Patron Capital, shares how he built one of Europe’s leading real estate firms from the ground up.

Greg Lauze, Managing Partner at NorthBridge Partners, discusses the evolving opportunity set in industrial real estate and the growth of NorthBridge as an institutional manager.

Dennis Lopez, CEO of QuadReal Property Group, discusses platform investing and Quadreal's broader investment strategy