Past Speakers
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December 18, 2023
MAYOR JANE CASTOR, City of Tampa, Florida
In 2019, the Tampa community elected Jane Castor to serve as the city’s 59th Mayor and re-elected her in 2023. In 2009, Jane became the first female Tampa Police Chief, serving for 6 years. In her second term as mayor, Jane remains laser-focused on her vision for “Transforming Tampa’s Tomorrow”—a five-pillar strategic plan centered around strengthening community-centric services, enhancing workforce development, increasing housing affordability, improving transportation, and fostering sustainability and resilience.
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December 11, 2023
Cindy Stuart, Hillsborough County Clerk of Court & Comptroller
Cindy Stuart was elected Hillsborough County Clerk of Court & Comptroller in September 2020 and sworn into office on January 5, 2021. Before her election as Clerk, she served eight years on the Hillsborough County School Board.
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December 4, 2023
Col (Ret.) DJ Reyes, JD, MA, National Veterans Rights Advocate Senior Mentor Program Coordinator, Tampa FL Veterans Treatment Court Appointee, US Secretary Veterans Affairs Advisory Committee on Homeless Veterans
J Reyes is a retired US Army Colonel with over 33 years of faithful service to our great Nation. Earning his bachelors, masters, and juris doctor degrees from the University of Notre Dame, the US Naval War College, and Temple University School of Law, DJ’s leadership resume also includes key command and staff positions in special forces / special operations, military intelligence, infantry, airborne, air assault, Joint, Interagency, and Multi-National organizations. Combat and contingency deployments included tours in Iraq, Afghanistan, North Africa, Bosnia, Kosovo, Haiti and Korea.
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November 27, 2023
Ed Ellsasser, CEO, PrimeGroup Insurance
Ed is the CEO of PrimeGroup Insurance which he started in 1999. PGI has 40 employees with offices in Tampa, Orlando, and West Palm Beach. PGI offers commercial insurance, employee benefits, and personal insurance including home and auto. PrimeGroup’s Core Values centers on clients, employees,
and giving back in the communities where we do business. PGI has been nominated for many awards over the years including Best Places to Work, Small Business of the Year, Tampa Bay Business Journal Top 20 Tampa Bay P and C Agency and Health Agency, and the Corporate Philanthropy Award. Ed
previously was a partner in PrimePay which had 500 employees and a 160 million dollar exit in March of 2021 and has been an investor in real estate and other businesses. Ed attended Indiana University where he earned his Bachelor of Arts in Economics. -
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November 13, 2023
Van Ayres, Superintendent, HIllsborough County Public Schools
Van Ayres serves as Superintendent of Schools for Hillsborough County Public Schools (HCPS), the nation’s seventh largest school system. He was appointed to the role on November 2, 2023.
Before being appointed Superintendent, Mr. Ayres served as Chief of Strategic Planning and Partnerships where he used his visionary leadership to direct and implement the district’s 5-year strategic plan, all while fostering community relationships. -
November 6, 2023
Matthew Gordon, CFO and Co-Founder, The Pickleball Club
Matt Gordon is a Co-Founder of The Pickleball Club whose mission is to build the nation's leading dedicated indoor pickleball facilities.
Mr. Gordon’s career spans business operations, finance and law. Mr. Gordon is a noted expert on legal topics related to visa-investment
organizational structure and visa-investment policy. He is the editor of the leading legal treatise on the EB-5 program, “The EB-5 Book”
and is a frequent writer and lecturer. He has also done policy work at Harvard University’s Kennedy School of Government and with the
White House. In February 2016, Mr. Gordon testified in front of the House of Representatives Judiciary Committee as a policy expert on
EB-5 matters.