Robert Caplin

Background

About Robert Caplin

I am a founding member of Metropolis Technologies, Inc. Metropolis is a proprietary AI and computer vision-based operating system built to modernize the parking industry and facilitate the future of mobility. During the company’s early years, I secured contracts for over 35 locations to facilitate the expansion and deployment of the Metropolis Technology Platform. I established long-term relationships with institutional asset owners and investors to insure continued future growth. I was instrumental in securing the initial seed funding, the $42 million Series A fundraise in 2020, and assisted in the $167 million Series B fundraise in 2022. As an Advisor, I mentor employees across multiple disciplines related to commercial real estate best practices, research, negotiations, and operations. In 2001, I joined Next Realty LLC, a Chicago based boutique commercial real estate investment firm as a Principal and Executive Vice President. Under my leadership, Next expanded its platform to include the acquisition of parking assets and I founded Next Parking. Over seventeen years, I oversaw all phases of property acquisitions and dispositions including sourcing, underwriting, negotiating Purchase Agreements, and the drafting and implementation of business plans to exceed investor expectations. I facilitated the acquisition of numerous parking assets, building a portfolio of prime parking properties in major U.S. markets. Together with the investment team, I underwrote commercial real estate and parking assets valued at over $2.5 billion. In addition, I was instrumental in establishing Next Parking Solutions, a parking consultancy business and asset management platform responsible for analyzing and directing operations in parking facilities for institutional and international infrastructure investors. While at Next, I was directly responsible for consistently delivering above market returns to investors. Prior to joining Next, I was Director of Acquisitions at Chicago-based Centrum Properties. During my tenure, Centrum acquired and developed a variety of commercial real estate properties. Acquisition targets included retail, multi-family, parking structures, and mixed-use projects, often requiring creative deal structuring and negotiating complex zoning, annexation, and contractual issues with both owners and municipalities.