Running a business with a spouse is hard enough without adding insurance regulations to the mix, but that is exactly the story Brad and Julia Dees bring to Sarasota SpeaX. The couple built Dees Insurance Group from the ground up in downtown Sarasota, and the conversation spends real time on how they divide the work, where they clash, and why the partnership has held together through the pressure of running a brokerage as a two-person leadership team.
What separates Dees Insurance from a typical agency, by their own account, is a heavy bet on education. Rather than just selling policies, Julia and Brad talk through how they built a following by explaining insurance to their clients in plain language, particularly on social media, at a time when most agencies were still leaning on cold calls and referrals. That approach has turned into a real differentiator as Sarasota's population keeps climbing and new residents arrive needing to understand coverage for the first time.
The hosts push the Deeses on how Sarasota's rapid growth has changed the insurance conversation for their clients, many of whom are themselves other local business owners navigating the same market pressures. It becomes a window into how fast the region is changing from the inside, seen through the lens of two people who talk to dozens of Sarasota families and businesses every week about risk.
As always, the episode closes with the hosts' favorite local ritual, getting the guests' take on Sarasota's ever-expanding roundabouts, before sending Brad and Julia through the Rapid Fire Gauntlet. It is a fun, fast finish to an episode that otherwise makes a strong case for education as a business strategy in a town where everyone is still learning how things work.
Running the Business Side by Side
The most candid stretch of the conversation comes when the hosts ask Brad and Julia how they actually divide responsibilities day to day, and the answer is less about a formal org chart than a working rhythm built over years of trial and error. Julia and Brad describe leaning on each other's strengths rather than splitting the business cleanly down the middle, an approach that keeps decisions moving without either one feeling boxed out of the parts they care about most.
That dynamic matters more in downtown Sarasota than it might elsewhere, given how fast the client base is growing and how many of those new clients are themselves small business owners navigating insurance for the first time. Dees Insurance Group has positioned itself as the brokerage willing to explain the fine print rather than just sell the policy, and Brad and Julia argue that patience is exactly what a rapidly changing Sarasota market needs right now.
What you'll take away
- Dees Insurance Group built its brand around educating clients rather than just selling policies.
- Social media became a core marketing channel for explaining insurance concepts to a growing local audience.
- Running a business as a married couple requires clear roles and communication under pressure.
- Sarasota's rapid growth is reshaping the kinds of insurance questions local clients are asking.
Places mentioned: Downtown Sarasota