About Orlando Opportunity Fund

The Orlando Opportunity Fund is a Qualified Opportunity Fund based in Central Florida. We are committed to leveraging our collective experience and new tax incentives to produce solid investor returns while stimulating communities through investments in commercial real estate and early stage companies. By investing in a Qualified Opportunity Fund for 5-7 years, investors can reduce their capital gains through a 10-15% increase in step-up basis. Investors can also defer this capital gain expense until 2026.

If the investment is held in the Opportunity Fund for ten or more years than investors permanently eliminate their taxable income on the gains generated from their Qualified Opportunity Fund investment. By investing in the right Qualified Opportunity Fund investors have the potential to leverage great tax incentives, earn solid returns and improve our communities that need it the most.

Startup Investments

Our startup investing strategy is focused on funding scalable early stage technology (or technology enabled) companies in Central Florida.  Our typical investments include:

  • Angel investments: $250,000 – $500,000 per company
  • Smart Money: We tend to invest in companies that we can add more value than only capital.

We have a strong commitment to our portfolio companies and invest our collective experience, capital, resources and network into their success.

If you have a venture that you would like our team to consider evaluating for investment, fill out our entrepreneur inquiry form today.  Your business will need to be located in an Opportunity Zone, or willing to relocate

Real Estate Investments

Our real estate investing strategy is focused on acquiring under valued or mismanaged real estate and properties ripe for repositioning located in Central Florida Opportunity Zones. Investments can be made into retail, offices, warehouse, storage, or multi-family properties. Ground-up development is also considered based on the deal and circumstance.


Real Estate investments will range generally from $1M to $5M, which are typically above the reach of most individual investors, but often below the size desired for institutional investors.

Investments in Orange, Seminole, Lake, Osceola, and Volusia counties will be given first priority; though other investments across Florida can also be considered. If you have a real estate opportunity that you would like us to consider, please contact us today.

Leadership Team

John Cooper, President Startup Investments

John A. Cooper serves as President of Startup Investments for the Orlando Opportunity Fund.  He has led or participated in financing and merger/acquisition activities for more than 200 technology sector companies, with specific focus in SaaS enterprise applications, Internet technologies, and Healthcare IT. Since 2014 he has been the managing director of Houlihan Lokey – ranked as the No. 1 M&A advisor for all U.S. transactions, the No. 1 global restructuring advisor, and the No. 1 global M&A fairness opinion advisor over the past 20 years.

Mr. Cooper served as Managing Director of Microsoft Corporation in corporate development and strategy group, where he performed a leadership role in investments & acquisitions, defining key corporate relationships and involved in more than thirty transactions. Mr. Cooper led the acquisition of Great Plains, Inc., Mr. Cooper advised ThinkTank LLC on the privatization of Buy.com, as well as the management and refinement of its technology investment portfolio. Mr. Cooper held senior corporate development and strategy positions with American Express Corporation, First Data Corporation, and HBO & Company, where he participated in more than two hundred strategic investment and acquisition processes. He played a central role in the founding of two venture capital-sponsored technology and services companies. He serves as an Executive Director of Archpoint Corp. Mr. Cooper has been an active Board Member for both public and private companies in the technology sector. He graduated from the University of Minnesota and completed Post Graduate Studies in Computer Science, Management and Marketing, including an executive management program at MIT in Advanced Technologies in Business.

Specialties: Venture Capital, Private Equity, Mergers & Acquisitions, Business Strategy, Strategic Partnerships, Due Diligence, Valuation, Financial Analysis.

Vince Wolle, President Real Estate Investments

Vince Wolle is an experienced commercial real estate executive, broker and investor with over 23 years of experience. Mr. Wolle is a Certified Commercial Investment Member and a member of the Society of Industrial and Office Realtors, which is known to include the best of the best in industrial and office real estate. As the founding broker of Results Real Estate Partners, Mr. Wolle has, since 2004, consistently been a top producer in Central Florida retail and industrial real estate, which has led to over 42+ awards. Overall Top Producer for Seminole County for 10 years by CFCAR. Personally average north of $40MM+ per year for the last 7 years. Designations of CCIM (Certified Commercial Investment Member) and SIOR (Society of Industrial and Office Realtors).Mr. Wolle’s career transaction volume exceeds $1 billion and six million square feet of commercial space. He has owned and redeveloped over 500K SF of commercial space and currently owns 39 real estate assets (currently owns over 400K SF of commercial assets now valued over $40MM+). Has extensive experience in redevelopment and managing construction and value add services to increase the ROI of existing assets.

Vince serves as the President of Real Estate Investments of the Orlando Opportunity Fund. He utilizes his skills, network and experience to help identify, conduct due diligence, purchase and manage investment real estate for the Orlando Opportunity Fund.

Specialties: Industrial, Retail, and Investment Real Estate. Construction Management Services, Redevelopment Partnerships.

Donna Mackenzie, Chief Financial Officer

Donna Lewis Mackenzie is a principle of the Orlando Opportunity Fund and serves as the CFO and COO. For the past four years Ms. Mackenzie has served as Executive Director of StarterStudio, a business incubator and accelerator program for technology startups. Ms. Mackenzie has been involved in numerous startups guiding them through idea stage, to initial angel investment, to venture capital series investments. Ms. Mackenzie has been involved in more than $90M in startup and early growth investments.

Ms. Mackenzie held the positions of Chief Financial Officer, Secretary and Treasurer of IZEA, Inc. (OTCBB: IZEA).   She also held the position of Executive Vice President of Operations, leading the financial, operational and customer service areas.  In May 2011, she and the founder of IZEA jointly achieved a management buyout of 100% of the stock of IZEA, and subsequently took the company public through a reverse merger.  Ms. Mackenzie also served on the Board of Directors of IZEA from May 2011 through September 2012.  Ms. Mackenzie was previously the Senior Vice President and Chief Financial Officer from March 2003 to June 2007 of Channel Intelligence, Inc., a provider of technology to companies to enable customers to buy their products online, subsequently acquired by Google.  From 2001 to 2003 she served as Chief Financial Officer of Cytura Corporation, which was sold to Mobius Management System (NASDAQ: MOBI).  From 1999 to 2001, Ms. Mackenzie led early stage web-based and content management solution start-ups with their business strategy and planning.  From 1995 to 1999, she served as Director, Principal and Founder in management consulting firms focused on process improvement and re-engineering service for private and public companies, including Fortune 100 companies.   Ms. Mackenzie also brings transactional expertise in mergers and acquisitions, equity offerings and bank financings.

Ms. Mackenzie holds a B.B.A. degree in accounting from the University of Alaska, Anchorage and is a licensed Certified Public Accountant in the State of Florida.  Ms. Mackenzie has previously served as a member at large of Council for the American Institute of Certified Public Accountants (AICPA) and as President of the Central Florida Chapter of Financial Executives Institute (FEI). Ms. Mackenzie has been a board member or advisor to organizations including Friends of the Library Orange County, WMFE 90.7, University of Central Florida Venture Lab and The Howard Phillips Center for Women and Children.

David Brim, Chief Strategy Officer

David Brim is a marketing strategist & entrepreneur turned investor focused on funding early stage companies & commercial real estate. He is the founding partner and Chief Strategy Officer of the Orlando Opportunity Fund. A graduate of the University of Central Florida, where he majored in marketing, David is the only two-time winner of the school’s Joust Business Plan Competition. Brim has founded numerous businesses in Central Florida across industries such as software, marketing, real estate, private lending, and ecommerce. He has been featured in one of the most popular entrepreneurship textbooks “Successfully Launching New Ventures”, selected as a top business blogger in Florida, and authored a best selling  book on digital marketing in 2013 that was also utilized in UCF entrepreneurial marketing courses.

Brim has been an avid real estate investor since 2010, and a licensed real estate professional focused on investment real estate since 2014. He is also an entrepreneur mentor for numerous organizations across Central Florida including the UCF Center for Entrepreneurial Leadership, Lift Orlando, StarterStudio and Startup Weekend. Since 2010 has been a lead consultant on the GrowFL team and National Economic Gardening team where he has helped over 1,000 second stage companies grow their business to create wealth and jobs in their local communities. In 2017 he founded Orlando Entrepreneurs, a network, resource center and podcast with the mission to connect, cultivate, and celebrate Central Florida entrepreneurs.

Specialties: business consulting, business model development, financial modeling & projections, fundraising & investor relations, marketing strategy, digital marketing, investment real estate, due diligence, entrepreneurship, angel investing.