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Michael began his career in the healthcare industry and then worked as a consultant to niche financial service sectors. In 2003, he founded Academic Financial Solutions (“AFS”), a student lending company that specialized in student loan consolidation. Over the next five years, AFS grew to become one of the largest student loan lenders in the United States.
In 2007, Michael led AFS through an acquisition with Frontenac Company, a prominent private equity firm based in Chicago. He remained as President and CEO of AFS until being named President of Two Rivers Ranch in 2010, a Holding Company with extensive corporate and real estate holdings throughout the United States.
Michael co-founded Osceola in 2014 and is focused on portfolio management and value creation efforts within Osceola’s portfolio companies. He is one of the main architects behind the General Partner’s philosophy and has successfully implemented this strategy as an investor and operator over the last decade.
Michael has the pleasure of serving on multiple non-profit and Osceola portfolio companies. He was also appointed by Governor Rick Scott to serve on the Governing Board of the Southwest Florida Water Management District for which he was elected Chairman and served until 2018.
Michael earned a BSBA with honors from the University of Richmond and holds an MBA from the University of South Florida. He is active in his community and church with his wife and three children and enjoys following sports, spending time outdoors and traveling abroad.
Ben started his career as an officer and hospital administrator in the United States Air Force. In 2005, he joined the Global Industry investing banking group at Bear Stearns in New York, before moving to Florida to join the Middle Market M&A investment banking group at Raymond James in 2007. During his five years in investment banking, Ben worked on advisory services and capital market financings for clients in over 20 different industries.
Prior to joining Osceola as a Managing Partner, Ben was the CEO of Avesta Asset Management, a real estate private equity firm focused on value-add multifamily investments throughout Florida and Texas. He also served as the CFO of Advantage Waypoint, a business services company within the food service industry.
Ben played a vital strategic role in the success of Advantage Waypoint, from its founding in 2011 to its eventual sale to Apax Partners in 2014—a span that included 24 buy-side acquisitions across the United States. He was named CFO of the year in 2014 by the Tampa Bay Business Journal.
Ben earned a BS with Distinguished Graduate designation from the United States Air Force Academy, and an MBA from Duke University. Ben lives in Tampa with his wife and two sons, and enjoys fishing, hunting and snowboarding.
Will began his career in New York at S Squared, a hedge fund specializing in micro-cap investments for institutional clients. At S Squared, he oversaw trading, finance and operations and managed all relationships with auditors, administrators, legal/compliance and banking service providers. Additionally, Will worked closely with investors to ensure their reporting, tax and analysis needs were met.
Prior to joining Osceola, Will worked in Los Angeles at Silver Rock, the family office for Michael Milken. There, he built out the fund’s infrastructure to allow for trading and management of additional asset classes. Additionally, Will shepherded the process of registering Silver Rock with the SEC allowing the firm to raise outside capital.
At Osceola, Will is responsible for the CFO and COO roles overseeing all finance and operations functions and managing vendor relationships. He also manages Osceola’s marketing and investor relations efforts and works with portfolio company management teams on identifying and implementing new efficiencies.
Will holds a CPA designation and earned a BS from Grove City College. He later went on to earn an MBA from Pepperdine University and an MS from Columbia University. He serves on the board of Le Pelican, a non-profit seeking to provide education and vocational training to Afghan women and children. Will lives in the Old Northeast neighborhood of St. Petersburg with his wife, Heidi, and enjoys hiking through national parks and following Major League Baseball.
Erik began his career as a Field Artillery officer in the US Army. Over 5 years, he led teams in roles including firing battery Platoon Leader and Fire Direction Officer, Battalion Fire Support Officer and Brigade Fire Control Officer. Erik led a 20-man firebase in Baghdad for twelve months in 2009 and 2010.
Prior to joining Osceola, Erik worked for Raymond James as Assistant to the Chairman, leading several internal consulting and corporate strategy projects. After this role, he continued one of these projects in a full-time capacity, leading the development of a cross-border program aimed at providing wealth management services for the firm’s international clients.
At Osceola, Erik focuses on all aspects of deal making including thesis generation, pipeline development, due diligence, portfolio company strategy, operational management and portfolio company M&A activity.
Erik earned a BS from the United States Military Academy where he also played basketball and baseball. He also earned an MBA from the University of Chicago's Booth School of Business. Erik lives in South Tampa with his wife, Jamie, and two dogs, Samson and Me-Lo. He serves on the board of the West Point Society Florida West Coast and enjoys traveling, reading and all types of fitness activities—especially weight lifting and yoga.
Patrick began his career in the investment banking group at William Blair in Chicago. While at Blair, Patrick worked on M&A advisory services and capital market financings for clients in the business and healthcare services industries.
Prior to joining Osceola, Patrick spent three years at Silver Oak Services Partners, a lower middle market private equity fund based in Chicago, IL that focuses on buyout investments in the business, healthcare and consumer services sectors. In his time at Silver Oak, Patrick completed platform investments, add-on acquisitions, recapitalizations, and portfolio company divestitures, and worked with portfolio company management teams on an ongoing basis.
At Osceola, Patrick is responsible for originating, evaluating and executing new investment opportunities, as well as partnering with portfolio company management teams to develop and execute strategic and operational initiatives. Patrick currently serves on the board of directors of Avision Sales Group, Central Medical Group and Top Gun Facility Services. Patrick's previous board participation includes Direct Travel, GKIC, Hero Practice Services, iSystems and Tranzonic.
Patrick earned a BS from Miami University and later went on to earn his MBA from Northwestern University's Kellogg School of Management. Patrick lives in Tierra Verde with his wife, Cari, and enjoys playing mediocre rounds of golf and exercising with his dog, Luna.
Luke began his career with Bright Equities, a family office located outside of Dallas, TX. While at Bright Equities, Luke was responsible for financial analysis and due diligence for private investments across a variety of industries in the lower middle market. Before Bright Equities, Luke interned with Vision Research, a short-only equity research firm in Dallas.
At Osceola, Luke is responsible for due diligence, financial modeling, deal execution, and assists with portfolio company oversight.
Luke earned a BBA in Finance and a minor in Economics from Southern Methodist University and was a member of the Portfolio Practicum honors investment management program. Luke lives in Tampa and enjoys traveling and playing golf with his friends.
Jordyn began her career in the Investment Banking division at Goldman Sachs in New York. While at Goldman, Jordyn worked on M&A advisory services and capital market financings for clients in the industrial sector. Prior to her time at Goldman, Jordyn interned with BMO’s Commercial Banking group.
At Osceola, Jordyn is responsible for due diligence, financial modeling, deal execution, and assists with portfolio company oversight.
Jordyn earned a BBA in Finance and a certificate in Entrepreneurship from the University of Iowa. Jordyn lives in Tampa and enjoys traveling, cooking, and running in her free time.
Jacob began his career working as an operations administrator at a law firm in Tampa. He then headed overseas, embarking on a humanitarian mission to Africa with an NGO to help create sustainable economic development solutions. Upon returning to the US, Jacob worked for Clearwell Group, a family investment advisory office, where he assisted with back-office administration and philanthropic advisory.
Jacob joined Osceola in 2016. He supports all operations functions of the firm and assisting with accounting, investor relations, financial reporting and general office management.
Jacob earned a BS from the University of South Florida. Jacob is passionately involved in the foster care and child advocacy community. He resides in Bradenton, Florida with his wife Peggy and four adopted children. He enjoys the beach-life, golfing, and biking with his family.