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20 Years of Tidewater: Built by People, Driven By Purpose

Before there were milestones, there were moments. The early mornings, the big ideas, the small wins that turned into something bigger. The relationships built over time. The people who showed up, grew together, and helped shape Tidewater into what it is today. As we celebrate our 20th anniversary, we’re not just looking back at where we’ve been; we’re reflecting on the voices, memories, and experiences that made us who we are.

Twenty years ago, Tidewater Management Group was founded with a vision – to create something meaningful. What’s been built since then is more than a company.

It’s a community.

While our growth spans across the country and our impact reaches thousands, the true story of Tidewater isn’t found in the numbers. It’s found in the people who have shaped it every step of the way.

Because at it’s core, Tidewater has never been just a business.

It’s a family.

The Moments That Shaped Us

Every company has its milestones, but the ones that truly define a culture are often the ones you can’t measure.

For many on our team, it started with something simple: the people.

Caitlin Kealey

Caitlin shared, “My very first impression of Tidewater was how kind my colleagues were. After almost 6 years spent here, I’m so thankful to say that it still holds (even when we are up against each other during team activities!). The best times of year are when we compete during scavenger hunts (my team always wins – for the record) and our annual White Elephant exchange during the holidays. Being surrounded by such genuine and hardworking people truly makes a difference in my day-to-day.”

For others, Tidewater has been a place of growth from the very beginning.

Logan Boggis

Logan shared, “I first came to Tidewater when I was 18 as a summer intern during my sophomore year of college. I kept coming back during breaks, and after graduating, starting full-time here felt like an easy decision. Since then, I’ve grown into my role as Digital Marketing Manager (with a little push from Todd). At Tidewater, you’ll find people who push you, believe in you, and want you to grow.”

And sometimes, it’s the unexpected paths that leave the biggest impact.

Megan Gilliam

Megan shared, “I started working at Tidewater in 2013. I was fresh out of college, living back home in Maryland, trying to apply to every job I could. I came upon a job listing on Craigslist (yes, Craigslist used to have legitimate job postings) that made absolutely no sense to me but was in Raleigh, NC. About a month later, Todd Fincher told me to pack my bags and come to Raleigh. Brian and I moved two weeks later.”

More Than a Workplace

What makes Tidewater special isn’t just what we’ve built – it’s how we’ve built it.

It’s in the shared experiences – the ones that turn coworkers into lifelong friends.

Logan Boggis

Logan captured it best: “My favorite memories are in the small moments: trivia and drinks after work, ridiculous scavenger hunts where I get way too competitive, and seeing who can eat the most saltines in a minute (it’s harder than you think)! I’ve grown up at Tidewater, and I’m incredibly grateful to be part of this team and this 20-year milestone.”

It’s also in the meaning behind the work itself.

Bobby Heptinstall

Bobby shared what makes the work so impactful: “When I started here almost twelve years ago, I had no idea what I was stepping into. It didn’t take long to realize the impact our work has on both agents and clients. I’ve always had a soft spot for seniors, thanks in large part to my grandmother, and that connection has made this career path really meaningful. Watching agents grow and succeed while also helping clients feel confident and supported as they navigate Medicare is very rewarding. It truly feels like a win for everyone involved.”

And for those who have been here since the early days, the growth has been something truly special to witness.

Mike Newton

Mike reflected, “Time has gone by fast. Watching us grow has been fun, but the most fun has been watching our families grow with us and seeing the opportunities it’s brought to so many of us. I remember when it was just Todd, Chad, and me in the small office down the street…when Serena first applied, and Megan’s interview after she applied on Craigslist. I have so many fun memories…just happy to be here since the start.”

A Culture That Carries Forward

From early road trips to big goals and defining moments, the culture of Tidewater has always been rooted in belief – in the company and each other.

Ronnie James

Ronnie shared one of those moments: “Maybe my favorite was when Todd, Chad, and I met up in Statesville and drove to meet an agent to recruit him. We talked about big dreams for TMG, and that’s when we committed to being all-in to make TMG the best it can be. It was a great trip.”

That same commitment has carried through the years of growth and change.

Chad Wilkerson

Chad reflected, “My 15-year journey with Tidewater has been truly inspiring. Together, we have achieved remarkable growth, overcome numerous challenges, and built lasting relationships. I am proud to be part of a team that continues to strive for excellence and am excited about the future we are creating together.”

And along the way, the impact of the work has never been lost.

John Elliott

John shared a moment that brought it all into perspective: “A favorite memory of mine is a dinner I attended with Todd and Jennifer Fincher and some of our partners on one of our incentive trips to Aruba. Listening to the business and personal stories of the agents we work with had me in full laughter, surprise, and made me realize the importance of agents leading clients to the right products. That dinner made me realize that what we do is important, and I try to bring as much value as I can to the agents who have chosen to partner with TMG.”

Looking Ahead

Twenty years is a milestone worth celebrating, but it’s also just the beginning. If the past shows us anything, it’s that the heart of Tidewater isn’t just in what we do, it’s in who we do it with.

It’s in the relationships, the memories, the growth, and the people who show up to build something meaningful together.

Here’s to the laughter, the challenges, the wins, and everything in between…To continued growth, lasting relationships, and even more memories ahead.

Here’s to the next 20 years of Tidewater Management Group.

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