Gerrard is a trusted business and tax advisor to entrepreneurs, closely held family businesses, and startups. He is a Florida Bar Board Certified Tax Attorney and serves clients across various industries including finance, hospitality, technology, real estate, healthcare, manufacturing, and entertainment. His experience as both a business-tax attorney and CPA is the best of both worlds for many clients and the skillsets he mastered in both areas stand out among his peers. Gerrard understands the financial implications of tax matters while navigating the legal aspects of complex tax law and business law matters for his clients and their advisors. His law practice includes representing early-stage startups to mid-size businesses and advising on capital raising, M&A, debt-refinancing, structuring complex transactions, and estate planning and asset protection. Gerrard serves as outside general counsel to for-profit organizations which include a registered investment advisory firm with $300 million in AUM and multiple non-profit organizations. In that capacity, he advises management on issues ranging from minimizing legal exposure and contract drafting and review, to daily operational matters. Having over a decade of experience representing taxpayers against the Tax Division of the U.S. Department of Justice, the Internal Revenue Service, and state and local taxing authorities, Gerrard devotes a significant part of his practice to helping taxpayers both domestically and internationally navigate all aspects of federal and state tax controversy matters. These matters include but are not limited to IRS liens and levies, employment and payroll tax, IRS appeals, CDP hearings, IRS audits, and examinations, IRS installment agreements, offer in compromise, and when needed, litigation in the U.S. Tax Court. Gerrard serves in various leadership roles within the Florida Bar and in his community. He is the 2023 – 2024 Chair of the Florida Bar Tax Certification Committee and serves on the Executive Council of the Tax Section where he is a Co-Chair of the IRS Collection Activities Subcommittee. He is a member of the Real Property Probate and Trust Law Section. He is also a proud board member of the UCF Alumni Board and sits on the Advisory Board of the Orlando Sports Foundation, Inc. As an attorney, Gerrard received the esteemed AV Preeminent rating by Martindale-Hubbell, the highest rating for attorneys who are ranked by their peers for exhibiting the highest level of professional excellence for their legal expertise, communication skills, and ethical standards. He has been recognized in publications such as Best Lawyers®, Super Lawyers, Florida Trend Legal Elite, and Orlando Family Magazine as an Awesome Attorney in Tax Law. In his spare time, Gerrard enjoys spending time with his family and is an avid sports fan of the Toronto Raptors NBA basketball team and enjoys rooting for the UCF Knights and Florida Gators sports teams. He is a supporter of Orlando City SC and Chelsea FC football clubs.

Ashley N. Naylor received her Bachelor of Science degree in finance from Florida State University and her Juris Doctor from Florida State University College of Law. She joined the firm after graduating from law school in 2013. Her primary practice areas are estate planning, probate, and trust administration. She is a member of Volusia County Bar Association and Florida Bar Association. She is also a member of the Real Property, Probate and Trust Law Section of the Florida Bar.

Trisha Dellinger received her Bachelor of Arts degree in political science from the University of North Carolina at Chapel Hill and her Juris Doctor from the University of Miami School of Law. She was admitted to the bar in 1997 and joined the firm in that same year. During her 25 plus years with Pyle, Dellinger & Naylor, PLLC, she has continuously concentrated in the areas of real estate and business transactions, elder law, estate planning, probate and trust administration. She is a member of the Volusia County Bar Association and Florida Bar Association. She is also a member of the Real Property Council of Volusia County, Academy of Florida Elder Law Attorneys, National Academy of Elder Law Attorneys and the Elder Law Section of the Florida Bar.

Craig R. Woodward practices law in Woodward, Pires & Lombardo’s Marco Island location. He joined his father, Arthur V. Woodward, Esq., in 1980. With decades of knowledge of the history and development of the local area, Craig brings a wealth of experience and insight to his clients in solving their legal matters. He handles real estate law, zoning issues, estate planning, probate, business law, and local government law. He represents hotels, restaurants, time-share projects, contractors, marinas, land developers, homeowner associations, real estate companies, banks, and private individuals. Craig held Board Certified in Real Estate Law by The Florida Bar from 1993 – 2023, having been the first Collier County attorney to receive this certification. He is rated AV Preeminent® by Martindale-Hubbell® Peer Review Ratings™, the rating standard given only to attorneys who rank at the highest level of professional excellence for their legal expertise, communication skills, and ethical standards by their peers. Active in the community, Craig was the keynote speaker for Marco’s 50th Anniversary in 2015 and was awarded the Lifetime Achievement Award by the Marco Island Chamber of Commerce and “Keys to the City” by the City of Marco Island, Marco City Council. He regularly writes historical articles and delivers lectures on Marco Island’s history, including to Leadership Marco classes each year. Craig is also Vice President of First Title & Abstract, Inc. and President of North Marco Utility Co., Inc. He was previously attorney for the Marco Island Independent Fire District (1991-1995).

Kenneth (“Ken”) V. Mundy is a partner with the law firm of Woodward, Pires & Lombardo, P.A. For undergraduate school, Ken graduated cum laude from Florida Gulf Coast University in 2013. Thereafter, Ken graduated summa cum laude from Ave Maria School of Law in 2016, where he obtained his Juris Doctor. Originally from New Jersey, Ken moved to Naples, Florida, with his parents and sister in 1997. Ken continues to happily reside in Naples with his wife, Taylor, his son, Dallas and daughter, Sophie. Ken is a Certified Financial Litigator (CFL™) focusing on family and marital law, including but not limited to complex divorces, child custody disputes, child support and alimony issues, relocation, paternity actions, and domestic violence proceedings. Ken is committed to protecting, educating, and guiding each client through the difficult and challenging processes associated with family law matters. In every case, Ken ensures his clients are placed in a position to make decisions in the best interest of themselves and their families while also maintaining their dignity and self-respect. Ken is also very involved in the community as he is on the Board of Directors for Meals of Hope and the Naples Junior Chamber, both of which are not-for-profit entities.

Amber is an attorney at Nishad Khan P.L. who focuses on civil litigation and probate administration. Amber attended the University of Central Florida where she earned a Bachelor of Science in Business Administration: Economics. She then attended law school at Stetson University College of Law receiving a Juris Doctor, Cum Laude. She also received an M.B.A. from Stetson University in 2011. Since becoming an attorney, Amber has worked in the Orlando area focusing on estate planning, probate and trust administration and litigation, civil litigation, and family law. Since 2016, she has been recognized as a Rising Star by Super Lawyer for her practice in Estate and Trust Litigation. Amber is licensed to practice law in Florida, the United States District Court for the Middle District of Florida, and the District of Columbia. In addition to her law practice, Amber has been providing pro bono services to the community through the Orange County Bar Association, while serving as a Committee Member and Chair of numerous Orange County Bar Association committees since 2014. In her role as Committee Chair of the Community Service Committee, she was a founding member of the Wills for Heroes Estate Planning Clinic in Orlando. In 2019, that program received the Florida Supreme Court Chief Justice’s Voluntary Bar Association Pro Bono Service Award. She was selected to receive the award on behalf of the OCBA Young Lawyers Section. When Amber is not working, you will find her spending time with her family and her two little boys. On Saturdays in the Fall, she will be sporting her black and gold while tailgating and attending UCF Football Games in Orlando. Go Knights!

Scott Willinger is a practicing lawyer in the state of Florida handling Estate matters.

Michelle Gilbert is admitted to the Florida Bar (1986), Washington, D.C. Bar (2020), Middle District of Florida (1988), Northern District of Florida (2005), Southern District of Florida (2006), U.S. Supreme Court (2000), and U.S. Court of Appeals for the Eleventh Circuit (2003). She matriculated at the University of South Florida (B.A., 1982, cum laude), and the University of Notre Dame Law School (J.D., 1985). She is a member of the following associations: Greater Tampa Association of Realtors; Bay Area Real Estate Council, Inc., Board of Directors; Hillsborough County Bar Association (Real Property, Probate and Trust Law; Solo and Small Firm; and Military and Veteran Sections); Florida Bar (Real Property, Probate and Trust Law; Business; and Solo and Small Firm Sections- Executive Council); American Legal and Financial Network; Legal League 100 (Vice Chairperson, 2016-19; Advisory Council Member, 2014-19; Special Initiatives Working Group, 2017- present); National Association of Default Professionals; Attorney Agent, Westcor Land Title Insurance Company and The Fund. She has managed the firm’s expansion into probate, estate planning, guardianship, civil litigation, business transaction and commercial collections, and oversees Sapphire Title & Escrow Company, launched in 2015. She is court approved counsel for guardianship cases in the Florida Thirteenth Judicial Circuit. Michelle has practiced real estate and business law since 1989, specializing in default servicing legal work, including litigated foreclosures, real estate closings, evictions, and commercial litigation. She works closely with the default industry by speaking at webinars and conferences, writing for industry publications, and consulting on various issues relevant to the industry. She was named 2021 Top 25 Women of Law by DS News, as well as selected as one of MReport’s 2015 and 2018 Leading Ladies. She taught the Florida Thirteenth Judicial Circuit Certified Process Servers Course from 1993 to 2014, and has written the chapter on service of process in real estate cases for the Florida Bar, since 2010.