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Jason appears in the Top 100 

Innovators & Entrepreneurs Magazine

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Jason Weiss


Jason Weiss, the founder and CEO of Ask Jason Weiss, embarked on a transformative journey that transcended the boundaries of his legal career. After practicing law for over two decades, he found himself deep in introspection, pondering how he could reach beyond the conventional teachings of law school. “Throughout my career, I’ve always been a round peg in a square hole,” Jason shares. “Unlike attorneys solely motivated by financial gain, I always prioritized the satisfaction of my clients, often leaving potential profits untapped. Money should never be a barrier to assisting those in need.”

Jason had discovered that his true passion lay in teaching, offering guidance, and acting as a mentor. Harnessing the power of social media, particularly Instagram, he shared his story, resonating with countless individuals who stumbled upon his posts. Before long, Jason became a magnet for attorneys who sought greater satisfaction from their own careers. In his mission to help others navigate paths towards fulfillment when conventional legal avenues seemed unviable, Jason deftly guided them towards alternative business options that could leverage their law degrees.

Now, through Ask Jason Weiss and his podcast of the same name (available on Apple, iHeart Radio, Spotify, Audible, and Amazon), Jason illuminates pathways to fulfillment for attorneys stuck in the quagmire of unhappiness. With a proven track record as a dealmaker, a compassionate heart, and an unwavering commitment to mentoring others, Jason is a beacon of inspiration and transformation that transcends the confines of the legal profession.

Despite his myriad professional accomplishments, Jason’s greatest fulfillment is as a devoted husband and father of two teenagers—an immensely talented son excelling in competitive lacrosse and a remarkable, multifaceted daughter. Proudly passing on his entrepreneurial spirit, both children established their own online apparel stores.

Jason’s educational background includes a Juris Doctorate, cum laude, from the University of Miami School of Law, and a BA with honors from the University of Florida. Licensed to practice law in both Florida and Washington, DC, his exceptional skills and reputation led to his recent appointment as a board member of Benefits Specialist Inc. He was also elected president of the Leadership Coral Springs Class of 2011, a testament to his remarkable leadership abilities, and has also served as an adjunct professor of sports law at Nova Southeastern School of Law, an adjunct professor at St. Thomas University, and as a judge for the Broward County Teen Court Program.

Jason Weiss
Ask Jason Weiss


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