(813) 435-5600 • info@clearwellgroup.com


Clearwell invests our partners' capital with the belief that business can generate positive impact in addition to investment return. We support high integrity entrepreneurs with a collaborative approach to creating value that leverages our experience and network. This aligns our interests with management to achieve the best possible outcome with the right amount of capital over the right period of time. Unlike the traditional fund structure, we bring patient capital to bear without artificial time constraints or temptation to overfund early-stage companies.

Clearwell makes control and meaningful minority investments in companies located in the southeastern United States with revenue ranging from $0 to $30 million across all stages of development. Industries of particular interest include healthcare, de-risked technology, food and beverage, consumer products, financial services, and software. However, we invest across a broad range of industries including manufacturing, select service sectors, and value-added distribution.

Investment Stages


Clearwell partners with entrepreneurs that have achieved proof of concept or have removed technology risk from an early stage product or service and can demonstrate exceptional growth opportunities. Our preference is to back revenue-positive businesses; however, we are comfortable with select investments in pre-commercialization stage opportunities.

Growth / Buyout

Clearwell partners with leaders of established businesses that require capital to accelerate growth through internal investment, acquisition of complementary product or service lines, or the acquisition of competitors. We will also make select investments to effect business recapitalization resulting in partial liquidity event.

Real Estate

Clearwell invests in commercial, industrial, and multi-family residential properties with a strong preference for opportunities located in Florida. We are not income investors, but rather focus on the total return potential of each property and the opportunity to add value beyond rehabilitation.


Douglas J. Free is the Managing Partner of Clearwell. Prior to starting Clearwell, Mr. Free was Senior Portfolio Manager and member of the Investment Committee for LCM Global, a hedge fund advisory business in Tampa, Florida. His investment background includes leading an investment due diligence team focused on Hedge Fund investing at Merrill Lynch as Director in the Hedge Fund Development and Management Group. While at Merrily Lynch, he was part of the investment team that established the first hedge fund platforms branded Hedge Access and Managed Futures Access. After managing the hedge fund research team at Merrill Lynch in New York, he took a leave of absence to join Geneva Global, a philanthropic advisor. As Director of Sector Research, he ran a team of analysts focused on six sectors of global development and focused on economic development, philanthropic performance measurement and microfinance lending. Mr. Free began his investment career at Raymond James where he worked as an analyst in the Equity Research group focused on exchange traded mutual funds. His background also includes investment banking with start-ups and bank workouts in Atlanta.

Mr. Free holds Bachelor degrees in Economics and History from Eckerd College and an MBA from Goizueta Business School at Emory University. He is married and has four children, is a drummer and enjoys water sports. Mr. Free serves on the advisory board of UF Investment Co. (UFICO) and the board of Tampa-based 4Kids, a non-profit serving foster parents.

Ryan D. Cortner is a Principal at Clearwell Group. Prior to joining Clearwell Group, Mr. Cortner was Vice President with Westshore Capital Partners where he was responsible for sourcing and analysis of investment opportunities, managing prospects through closing, and monitoring of existing portfolio companies for owner recapitalizations, family succession recapitalizations, management buyouts, management buy-ins, and industry consolidation. Prior to joining Westshore Capital Partners, Mr. Cortner was Manager in the New York office of PricewaterhouseCoopers' Transaction Services Group. During his tenure at PwC, Mr. Cortner's work focused on financial due diligence, strategic assessments/alternatives, and corporate carve-out transactions. While with PwC, he advised on over 75 public and private transactions ranging in size from $5 million to $5 billion. His industry experience includes manufacturing, business-to-business services, media and entertainment, technology, transportation, security, and consumer and industrial products among others.

Mr. Cortner holds both a Masters of Accounting with a concentration in Systems and a Bachelor of Accounting with Honors from the University of Florida. In addition to his formal education, he is a Certified Public Accountant and holds the Chartered Financial Analyst designation. Mr. Cortner serves on the board of the Tampa chapter of Association for Corporate Growth and is a member of Idlewild Baptist Church. He is married and has three children.