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Osceola’s advisors are a collection of highly accomplished current and former chief executives who offer a wealth of knowledge across various industries. They possess tremendous experience navigating the challenges of managing complex businesses and building effective teams. We value their wisdom and solicit their insights and advice when weighing difficult decisions and considering investment opportunities.
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 South Tampa with his wife, Heidi, and enjoys biking, grilling after a day at the beach, 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 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 Tampa with his wife, Cari, and enjoys playing mediocre rounds of golf and exercising with his dog, Luna.
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 Tampa, Florida with his wife Peggy and four adopted children. He enjoys the beach-life, golfing, and biking with his family.
Dr. Harold Babb has a distinguished career, both as an educator and entrepreneur. He successfully co-founded and sold businesses in the health care (emergency centers), investment banking (Matrix Capital), student financial services, and renewable energy sectors. Matrix Capital specialized in working with middle market private equity controlled and privately-held company clients in sell/buy side advisory, capital raises of debt and equity, and corporate valuations. Dr. Babb ultimately helped orchestrate the acquisition of Matrix by the publicly held Money Group Inc.
Dr. Babb has served as Professor and Chairman of Marketing with the Robins School of Business at the University of Richmond. He is a 1972 graduate of the University of Richmond with a BS in Accounting. He continued his education, receiving a MS in Marketing and Finance from Virginia Commonwealth University, and a PhD in Marketing from Virginia Polytechnic Institute and State University (Virginia Tech). He was a Fulbright-Hayes Scholar to South Korea and the Republic of China, the recipient of the F. Carlyle Tiller Distinguished Professor of Business Chair, received the University Distinguished Teaching Award and was recently inducted into the University of Richmond Athletic Hall of Fame.
Dr. Babb currently serves on the National Executive Board for Lead Like Jesus, is Chairman of the Board for the Central Virginia Salvation Army and is an Elder in his local church in addition to other civic and professional work.
Robert Thomas is the CEO of Two Rivers Ranch, Inc., Hickory Hills Land Company, Crystal Springs Preserve, Inc. and Balsam Gap, Inc. He is a third generation Tampa, Florida native and a 1977 graduate of the University of Richmond.
Mr. Thomas previously oversaw the sale of Port Sutton, the largest privately held deep water port in North America. Port Sutton was a privately held company for over 40 years prior to being sold to the Port of Tampa. Since that time, Mr. Thomas has received numerous accolades for his companies’ accomplishments. He was the co-founder of Florida Energy Capital, LLC.
Mr. Thomas is actively involved with numerous organizations. He is currently the Chairman of the Florida Land Council, Chairman of the Florida State Fair Foundation, Vice Chairman of the Florida State Fair Authority, Chairman emeritus of Lowry Park Zoological Society and serves on the Federal Reserve Bank of Atlanta’s Agriculture Advisory Council. He is also on the boards of Ave Maria University’s Board of Regents, Crystal Springs Foundation, Lykes Bros., Inc., Richmond Council of the University of Richmond, Tampa Bay Chapter of the American Red Cross, University of Tampa Board of Trustees, Guy Harvey Ocean Foundation and is presently Chairman of the Tampa Museum of Science and Industry.
Tony Umholtz has extensive experience in the financial services industry in both management and production roles. He has been ranked nationally as one of the top producers in the mortgage banking industry by the Scotsman Guide and Mortgage Originator Magazine. He has personally orchestrated over $1 billion in lending.
Mr. Umholtz started his finance career at Merrill Lynch in New York in 2001, assisting in equity analysis. He is also one of the original limited partners in Florida Energy Capital, LLC and Osceola Capital Holdings I, LLC. Mr. Umholtz earned a BS in Finance and an MBA from University of South Florida where he graduated Cum Laude. During his time at USF, Mr. Umholtz was an Academic All American and received AP All American honors. After completing college, he played professional football in the NFL with multiple professional teams as a punter and kickoff specialist.
He currently serves on the boards of Tampa Bay Fellowship of Christian Athletes and University of South Florida National Alumni Association.
Robert Collins has enjoyed a successful 30-year career in finance. Most recently, Mr. Collins was Managing Director and Co-Chief Investment Officer of Equity Investment Management in Goldman Sachs’ London office. There, he led a team of over 50 individuals responsible for investing nearly $40 billion in European and global equities portfolios. Prior to that, Mr. Collins was Managing Director and Co-Chair of the Investment Committee for Goldman Sachs’ US growth equity investment management business in Tampa, Florida. In that role, he was one of the leaders of a team managing $20 billion in US equities. Both businesses were highly successful with solid asset growth and excellent investment performance.
Currently, Mr. Collins is the Tampa Bay President of the National Christian Foundation, a group that seeks to maximize its client’s charitable giving potential. Mr. Collins founded the Tampa Bay Chapter and has since grown it to $100 million.
Mr. Collins earned a BA with honors from the University of South Florida and an MBA from the University of Tampa.