Orlando Opportunity Fund

The firm splits leadership by asset class. John A. Cooper, a former Houlihan Lokey managing director and Microsoft M&A executive, leads startup investments. Vince Wolle, a CCIM and SIOR designee with over $1 billion in career transaction volume, leads real estate investments. Chief Strategy Officer David Brim and CFO Donna Lewis Mackenzie round out the principal team, with Mackenzie bringing public-company CFO experience from IZEA and Channel Intelligence.

The firm’s primary sourcing engine is the Central Florida entrepreneurial network anchored by David Brim’s Orlando Entrepreneurs platform, a resource center and podcast he founded in 2017. Brim is also an active mentor at UCF’s Center for Entrepreneurial Leadership, StarterStudio, and Lift Orlando. The fund requires that any startup investment either be located in an Opportunity Zone or agree to relocate, which functions as a geographic filter on deal flow.

Because the fund is structured as a Qualified Opportunity Fund, investors can defer capital gains taxes until December 31, 2026, receive a 10 percent step-up in basis after five years and an additional 5 percent after seven years, and permanently exclude any taxable income on gains from the QOF investment itself if held for at least ten years. These rules are statutory under the 2017 Tax Cuts and Jobs Act and the fund has no discretion to alter them.

First priority is given to Orange, Seminole, Lake, Osceola, and Volusia counties in Central Florida. The firm states that other investments across Florida can be considered, but its Opportunity Zone mandate ties it to specific census tracts designated under the federal program, effectively limiting its geographic reach to designated areas within the state.

It operates as an asset manager and Qualified Opportunity Fund, not a single-family office. It raises third-party capital that qualifies for QOF tax treatment and deploys it across two distinct strategies—real estate repositioning and early-stage startup investing. There is no disclosed family-wealth origin or single-family anchor capital.

The fund’s mandate excludes real estate deals below $1 million and startup investments below $250,000, and it does not target institutional-scale transactions above $5 million in real estate. It also explicitly requires that any startup investment be in a technology or technology-enabled company, ruling out traditional brick-and-mortar small businesses that do not have a scalable tech component.

The firm requires that portfolio companies either be located in an Opportunity Zone at the time of investment or be willing to relocate. The QOF rules do not create a clawback if a company later moves, but the fund’s underwriting is built around the assumption that the investment will maintain its zone nexus for the duration of the hold period needed to maximize tax benefits.