Ben oversees all aspects of the firm’s investment activities including origination, evaluation, and execution of investments. As a member of the Investment Committee, he serves on the boards of several Osceola portfolio companies including Central Medical Supply Group, Forward Solutions, Industry Services Co., PayrHealth, Quote.com, Revelation Pharma, and Tendit Group. Ben has completed over 65 M&A transactions to date across a wide variety of industries.
Previously, Ben served as CEO of Avesta Asset Management, a private equity firm focused on value-add multifamily real estate investments. Before Avesta, he was CFO of Advantage Waypoint, an outsourced business services company, where he helped lead the acquisition of 24 businesses before an eventual sale to Apax Partners. Ben also spent six years in the investment banking groups of Bear Stearns and Raymond James and five years as a United States Air Force officer and hospital administrator.
Ben earned an MBA from Duke University and a BS with Distinguished Graduate designation from the United States Air Force Academy. Ben lives in Tampa with his wife and two sons and enjoys fishing and snowboarding.
Patrick is responsible for originating, evaluating, and executing new investment opportunities, as well as partnering with portfolio companies to develop and execute strategic and operational initiatives. Patrick currently serves on the boards of Central Medical Supply Group, Forward Solutions, Industry Services Co., Revelation Pharma, Tendit Group, & Flotilla Partners. Patrick’s previous board participation includes Direct Travel, GKIC, Hero Practice Services, iSystems, and Tranzonic.
Prior to joining Osceola, Patrick was an Associate with Silver Oak Services Partners, a middle-market private equity fund based in Chicago with over $1.1 billion under management, where he was responsible for investments in the business, healthcare, and consumer services industries. He began his career in the investment banking division at William Blair, where he was involved in a variety of merger and acquisition transactions.
Patrick earned an MBA from Northwestern University’s Kellogg School of Management and a BS degree in Finance from Miami University. He also serves as a member of the National Advisory Board of his alma mater, Archbishop Moeller High School. Patrick lives in St. Petersburg with his wife and daughter, and enjoys playing mediocre rounds of golf and exercising with his dog, Luna.
Will oversees all aspects of Osceola’s day-to-day operations including all finance functions, management company and fund tax matters, administration of the firm’s compliance program, and managing fundraising and investor relationships. As CFO and COO, Will also sits on the investment committee and opportunistically assists with due diligence and post-close portfolio company integration and management.
Prior to joining Osceola, Will was a Vice President at Third Lake Capital, a family office in Tampa, and Director of Finance and Operations at Silver Rock Financial, the investment arm of Michael Milken’s multi-billion-dollar family office in Los Angeles. There, he built out the fund’s infrastructure to allow for trading and management of additional asset classes and shepherded the eventual spin-off and registration with the SEC allowing the firm to raise outside capital. Will began his career in the alternative investment industry at S Squared, a micro-cap hedge fund in New York with $2 billion of institutional capital under management where he served as Controller and Director of Fund Operations overseeing the finance, compliance, trading, and investor reporting functions.
Will holds a CPA designation and earned an MBA from Pepperdine University and an MS from Columbia University. He earned a BS in Finance with a minor in French from Grove City College. He sits on the board of Le Pelican, a non-profit seeking to provide education and vocational training to Afghan women and children. Will lives in St. Petersburg with his wife and enjoys hiking through national parks and following Major League Baseball.
Michael founded Osceola in 2014 and is focused on management and value creation efforts within Osceola’s portfolio companies, broadening the firm’s relationships within target industries and investor networks and other key operational initiatives. As a member of the investment committee, Michael sits on the boards of CMS Technologies and Talent Group and is a board observer with Anuvia.
Prior to Osceola, Michael served as President of Two Rivers Ranch, a holding company with extensive corporate and real estate holdings throughout the United States. 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.
Previously, Michael founded Academic Financial Solutions (“AFS”), a student lending company that specialized in student loan consolidation. Over five years, AFS grew to become one of the largest student loan lenders in the United States. Michael led AFS through an acquisition with Frontenac Company, a prominent private equity firm based in Chicago.
Michael earned an MBA from the University of South Florida and a BSBA with honors from the University of Richmond. He is active in his community and church with his wife and three children and enjoys following sports, spending time outdoors, and traveling abroad.
Miles is responsible for all aspects of the deal process including thesis development, identifying and evaluating investment opportunities, and supporting portfolio companies.
Prior to joining Osceola, Miles was a Senior Associate at Tower Arch Capital, a lower-middle market private equity fund based in Salt Lake City with over $700M under management. While there, he executed transactions in the consumer, telecommunications, and infrastructure services industries. Miles began his career at L.E.K. Consulting in the Los Angeles office. While at L.E.K., Miles supported clients in the private equity, media & entertainment, life science, and technology sectors.
Miles earned an MBA from the University of Chicago’s Booth School of Business and a BS in Accounting, cum laude, from Brigham Young University. Miles lives in Tampa with his wife and two sons and enjoys sports, cooking, and traveling (especially road trips).
Kurt is responsible for all aspects of the deal process including thesis development, identifying and evaluating investment opportunities, and supporting portfolio companies. Kurt currently serves on the board of Flotilla Partners.
Prior to joining Osceola, Kurt was a Senior Associate at Cold Bore Capital, a Chicago-based lower-middle market private equity fund where he executed transactions in the healthcare services, business-to-business services, and consumer services sectors.
Before Cold Bore Capital, Kurt was an Associate within BMO Capital Markets’ Investment Banking Group, where he covered the healthcare sector. During his time at BMO, Kurt gained experience executing buy-side and sell-side M&A transactions as well as debt and equity financings. Before joining BMO, Kurt held various roles in financial services at J.P. Morgan and Cambridge Associates. Prior to his career in finance, Kurt served for six years in the U.S. Navy, where he was a Supply Corps Officer. During his military service, he held multiple departmental leadership positions and completed one deployment to Afghanistan.
Kurt earned an MBA from Columbia Business School and a BS in Finance from Penn State University. He lives in Tampa with his wife, two children, and their Alaskan Klee Kai, Domino. Kurt enjoys collegiate and professional football, traveling, reading, cigar tasting, and supporting fellow veterans.
Jake is responsible for due diligence, financial modeling, and assisting with all aspects of deal execution and portfolio company oversight. He is a member of the Industry Services Co., Central Medical Supply Group, and Talent Group deal teams.
Prior to joining Osceola, Jake started his career at Hyde Park Capital, a boutique investment bank, where he worked on sell-side mergers and acquisitions for healthcare, business services, and industrial companies. Prior to his time at Hyde Park Capital, Jake interned with Cherokee Capital, a direct investment family office focused on industrial services businesses.
Jake earned his BS degree in Finance from Florida State University. Jake lives in Tampa with his dog Oliver and enjoys boating and trying new restaurants in his free time.
Prior to joining Osceola, Sean worked as an Investment Banking Analyst at Truist Securities. While there, he worked in the Leveraged Finance group under the Industrials & Services vertical. Sean was responsible for underwriting and originating new credit facilities. Prior to his time at Truist, Sean worked as an Associate at PwC in their Financial Markets group.
Sean earned his MS degree in Finance from Indiana University’s Kelley School of Business and his BS degree in Finance and Entrepreneurship from the University of Louisville. Sean lives in St. Petersburg and in his free time, he enjoys playing golf, watching sports, exploring National Parks, cooking, bourbon tasting, and traveling with his girlfriend and dog, Birdie.
Prior to joining Osceola, Cassy was a full-time student and ran her own small e-commerce business selling coastal-themed home decorations. She also interned with a dance fitness company, where she assisted with finance and operations.
Cassy earned her MS degree in Finance from the University of Texas at Austin, and her BS degree in Economics from the University of Maryland. In her free time, she enjoys swimming, skiing, watching sports, and collecting miniature model buildings. She lives in Tampa with her cat, Darby.
Sara is responsible for managing many of Osceola’s operational initiatives including accounting, investor reporting, audit preparation work, and interfacing with key vendors such as the fund administrator and banking partners. Additionally, Sara collects and compiles key portfolio company data to aid the portfolio valuation process.
Prior to joining Osceola, Sara co-owned & held the role of Director of Operations for a commercial building services business. Before starting her own business, she worked as a project manager for a healthcare management company. Sara began her career in healthcare administration.
Sara earned a BS from the University of Texas at San Antonio. She is a passionate champion of a Door of Hope, a local Tampa Bay foster care agency. Sara was born & raised in Houston, TX but loves calling Florida home. In her spare time she enjoys walking trails, traveling & trying new restaurants. Sara resides in Tampa, Florida with her husband.