Jack Ashby

Jack’s insurance career began with Self Defense Liability through USCCA before he transitioned into the commercial insurance sector, where he found his niche. With years of hands-on experience and a deep understanding of the challenges that come with running hard-to-ensure businesses, Jack is not just an agent—he’s a client, too. As a business owner himself, he knows firsthand the complexities and unique needs of industries that often find it difficult to secure coverage. His passion for helping his clients stems from his own experiences, and that personal connection is what sets him apart.

With a body covered in tattoos (and more on the way), a love for cigars, and an appreciation for firearms, Jack connects naturally with the communities he serves. He understands the lifestyle and culture of his clients because he is part of it. Whether it’s artists, shop owners, or small business entrepreneurs, Jack builds meaningful relationships and is always accessible—whether it’s through a quick call, text, email, or even social media, he is never far away.

Beyond insurance, Jack’s commitment to service runs deep. A proud US Marine veteran who served in Afghanistan, Jack has always been driven to give back to his community. His work with Micheal’s Foundation, an equine therapy non-profit, is just one of the many ways he stays involved. As a Shriner and Freemason, Jack also dedicates time to helping fellow veterans, particularly those dealing with PTSD and substance abuse issues. His compassion for his fellow service members is unwavering, and his volunteer work reflects his commitment to making a difference.

When he’s not working, Jack embraces the outdoors and the hobbies that bring him joy. From fishing, hiking, and hunting to horseback riding, he stays connected with nature. Jack has a particular fondness for tattoos, often paying for new pieces with old pirate coins—a unique tradition that adds to his character. In addition, Jack is a passionate sports fan, supporting both the Portland Timbers FC and Orlando City SC, staying loyal to his roots while embracing his new home in Central Florida. He shares these adventures with his two dogs and his amazing girlfriend, with whom he experiences life’s many thrills and adventures.

Jack’s approach to insurance is rooted in authenticity, experience, and a genuine desire to help others. Whether you’re inking your next tattoo or running a small business, Jack understands what it takes to succeed and has your back every step of the way.