Earning Trust, One Deal at a Time – Drew Dolan, DXD Capital

In this episode of the Rainmaker Podcast, host Gui Costin welcomes Drew Dolan, co-founder and principal of DXD Capital, for a compelling conversation on data-driven development, investor relations, and building a specialized real estate platform. With over 20 years in real estate and a deep passion for ground-up development, Drew shares how he transitioned from technical sales into leading one of the most forward-thinking firms in self-storage.

Founded in 2020, DXD Capital was built on the belief that self-storage is a real estate-driven asset class where location and timing are everything. By leveraging a proprietary analytics platform, Radius+, co-created by Drew’s partner, DXD is able to assess rates, density, competition, and demographic trends with precision. This data-first strategy has helped DXD identify and develop prime self-storage projects across the U.S.—from Nantucket to Maui.

Drew walks through the firm's capital strategy, explaining their evolution from a $63M LP fund to a flexible model incorporating both funds and one-off joint ventures with family offices. This structure allows DXD to cater to both high-net-worth individuals and large institutions, with a focus on customization, transparency, and performance. Drew emphasizes that communication is key—monthly updates, timely financials, and responsiveness help build trust with their 300+ investors.

Internally, DXD runs a lean, focused operation with 30 employees spread across three main offices and remote locations near active projects. Slack and weekly check-ins are central to internal communication, while in-person retreats help maintain cultural connection. Drew also shares his leadership philosophy, centered around empowering others, encouraging ongoing learning, and hiring people who are better than him in key roles.

From an IR standpoint, DXD recently expanded its team, bringing in professionals with strong relationship instincts and private equity backgrounds. Drew underscores that while industry knowledge can be taught, trust and human connection are what open doors. Their tech stack, including Juniper Square and HubSpot, helps them manage investor communication and track data, but Drew admits the most effective outreach still comes down to “hand-to-hand combat.”

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