- The Florida Bar in 1997
- U.S. District Court, Middle District of Florida in 2000
Overview
An attorney at Jimerson Birr, P.A., Sean A. Espenship is a Florida-native attorney and CPA where he combines more than 25 years of corporate, tax, and litigation experience with a genuinely entrepreneurial point of view.
Dual-credentialed as a licensed attorney and Certified Public Accountant, Sean advises growing companies, family businesses, real estate developers, contractors, and private-equity-backed platforms on formation strategy, complex tax structuring, risk management, major acquisitions, reorganizations, partner buyouts, multi-state expansion, business succession, and estate and asset protection. He is equally comfortable at the very first whiteboard meeting with a startup founder and at the closing table of a nine-figure deal. He advises on optimal entity structures tailored to operational, tax, and market needs, handles formation and compliance, and crafts governing documents and agreements that safeguard interests while anticipating future opportunities and obstacles.
What sets Sean apart is that he has actually lived many of the same challenges his clients’ face. Since 2007 he has owned and operated a small rural water utility company in Lake City with his brother. In 2014 he founded The Jacksontucky Distillery in Jacksonville Beach, where he serves as master distiller and personally produces award-winning bourbons—including multiple gold medals from the San Francisco World Spirits Competition, the most prestigious and competitive spirits competition on the planet. He previously served as General Counsel for a $30 million enterprise that expanded across multiple states, ultimately overseeing a structure of 45 separate entities under one umbrella.
That real-world operator experience—coupled with nearly two decades of state and federal courtroom litigation—gives him a practical, battle-tested lens when counseling clients on entity choice, governance documents, shareholder and operating agreements, private equity raises, zoning and land-use matters, contract negotiations, corporate disputes, delivering tax-smart, goal-aligned solutions for every facet of the business lifecycle, as well as providing sophisticated estate and asset protection planning designed to preserve wealth across generations while guarding against spurious lawsuits and unfounded creditor claims.
A few law-school stories still circulate: on what he describes as “a complete whim,” Sean sat for the CPA exam during his final year of law school and passed all four parts on the first attempt, a rare triumph when the national pass rate was 13–15% at the time. He just shrugged and kept moving.
A Jacksonville Beach native and proud Fletcher High alum (Go Senators!), Sean never strayed far from the shore—the “Salt Life” is in his blood. He and his wife, the stunning Carolina from Medellín, Colombia, chase adventures with their daughter, traveling frequently between Florida, Colombia, and wherever the next family gathering or good wave might be. In his free time, you will catch him surfing, walking on the beach with his girls, strolling on bikes at low tide, weekend jaunts to St. Augustine, watching his beloved Liverpool FC at his favorite pub (Lynch’s), or tinkering in “The Lab”—the affectionate name for his Jax Beach craft distillery—where he refines his whiskies with a nod to his moonshining ancestors from Lake City.
Sean brings serious legal and tax horsepower to the table, but he delivers it with the perspective of someone who has met a payroll, lost sleep over a state alcohol audit inspection, celebrated gold medals, and signed personally on every line of credit. Clients say he feels more like a trusted co-founder than outside counsel—and that’s exactly how he likes it.
