The following is an interview between Bobby Garon of Naples, Florida, and VoyageMIA.
Today we’d like to introduce you to Bobby Garon.
Hi Bobby, so excited to have you with us today. What can you tell us about your story?
I got into finance and insurance in a fairly traditional way. I studied finance at Florida Gulf Coast University, and early in my career I focused heavily on the technical side of the industry, dealing with the products, the numbers, the licensing, etc. I worked in roles across banking and insurance advisory at JPMorgan Chase and Morgan Stanley, and earlier on as a licensed insurance advisor handling commercial and personal lines at Brown & Brown Insurance. Along the way I picked up my FINRA Series 6, Series 63, and SIE licenses, along with Florida Life, Annuity, and Property & Casualty insurance licenses.
One of the bigger transitions for me was moving from insurance advisory into banking and wealth management. On paper it sounds like a lateral move within the same industry, but professionally it was closer to starting over. I had the licenses and the technical background, but none of the relationships or track record that actually build a business on the banking side. I had to get comfortable being the new guy again, even in a field I already understood, which isn’t as easy as it sounds.
That experience is a big part of why I don’t take relationships for granted. Today, I’m based in Naples, Florida, where I help individuals and families think through financial protection and planning, and I try to bring the same approach that helped me rebuild then: showing up consistently and listening first, long before I ever talk product.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Making the shift from insurance advisory into banking sounds simple enough on paper, but professionally it was close to starting from zero. I was never worried about my licenses or my technical skillset. What I underestimated was how much of this business runs on people already knowing and trusting you, and in this new lane, I didn’t have that yet.
There were a few rough months of making calls to people who had no real reason to trust me yet, and hearing a lot of polite no’s. I remember sitting in the parking lot after a meeting that had gone nowhere, wondering if coming back had been a mistake. It wasn’t the job itself that was hard. It was rebuilding credibility in a market where I didn’t have a track record yet.
What got me through it was just putting in the reps, showing up to the same events, following up when I said I would, staying consistent even when nothing seemed to be moving. Becoming a father since then has reinforced the same lesson in a different setting: consistency matters more than any single big effort.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I’m a finance and insurance professional based in Naples, Florida. I work with individuals and families on financial planning, protection, and long-term security. My background spans banking, insurance advisory, and securities, which gives me a broader view than someone who’s only worked in one lane of the industry.
What I specialize in, more than any single product, is helping people get past the intimidation that usually surrounds financial decisions. Financial and insurance conversations can feel overwhelming, especially for people who feel behind or unsure. My job is to make that conversation feel less like a sales meeting and more like sitting down with someone who genuinely has your interests at heart.
What I’m most proud of is staying consistent with people, bringing the same patience and curiosity to every client regardless of their situation or how much business is on the table that day.
What sets me apart, I think, is that I don’t treat every client the same way just because their policy or plan looks similar on paper. Every person walks in with a different story, and I’d rather spend extra time understanding that story than rush to a recommendation that technically checks a box but doesn’t truly fit their life.
Are there any apps, books, podcasts, blogs or other resources you think our readers should check out?
Honestly, some of the most useful resources in my life haven’t been industry specific. I try to stay disciplined about reading things outside of finance, since a lot of what’s shaped how I work with clients came from observing people, not studying spreadsheets.
Two books that have helped me are “Atomic Habits” by James Clear and “How to Win Friends and Influence People” by Dale Carnegie. The first reshaped how I think about consistency, both with clients and at home. The second is decades old at this point, but it still holds up better than almost anything modern written on building real trust with people.
As for apps, I use Headspace fairly regularly. It’s a meditation and mindfulness app, and I mainly use it for short guided sessions to reset between meetings. Between client work and being a new dad, it’s become a simple way to stay present instead of constantly running ahead to the next thing on my list.
