Greg Gaines
From IT Professional to Legacy Franchise Owner
How a Father's Search for Legacy Led Him to British Swim School
Greg Gaines Franchise Ownership Success Story
Table of Contents
Introduction / Background
Greg Gaines built his career in IT.
He had decades of professional experience behind him, including leadership roles spanning customer service and technology. He'd even run his own business before, as an eBay Power Seller, so the idea of ownership wasn't foreign to him.
But something was missing.
His IT career was fulfilling and rewarding. It just wasn't enough.
The Trigger: Building Something for the Next Generation
A few years ago, Greg's son was born. That changed how he thought about his career.
"I realized that my current career as an IT professional was certainly fulfilling, was certainly rewarding, but I thought there was probably more I could do that would benefit him long term."
He wasn't just looking for a new job. He was looking for a legacy, something both he and his son could be proud of.
Franchising made sense to him for a simple reason: a tried-and-true model he could execute on, rather than build from nothing.
His connection to Terry started small, a LinkedIn outreach from someone on Terry's team, asking if he had any interest in franchising.
"It just so happens that at the time I did."
The Initial Direction: Casting a Wide Net
Terry didn't hand Greg a list of franchises right away. He took the time to understand what actually drove him.
For Greg, that meant:
- A meaningful impact on his community
- A connection to children specifically
- A proven, tried-and-true business model
- Cost-effective operations
- A strong, sustainable business model
From there, Terry brought back a handful of franchises he thought could be a fit. Greg and Terry went back and forth, narrowing the list to three or four real contenders, eventually landing on two finalists.
The Turning Point: Choosing Tried and True
One finalist was a fundraising franchise built around high school students. Greg liked it. But it lacked a long operating history, and Greg wanted something proven.
The other was British Swim School, with over 45 years in operation.
"You can't get any better than saving lives, particularly saving kids' lives."
The long track record mattered. So did the mission. As Greg learned more, his interest only deepened.
"Every day, every week that I learned about it, my passion for it just grew and grew."
The Franchise He Chose: British Swim School
British Swim School wasn't just a category Greg liked. It connected to his own story.
"I started swimming at the age of four. I've got that long history of swimming."
Beyond the personal connection, the operational model fit how Greg wanted to build a business: partnering with existing pool facilities rather than building expensive standalone locations, keeping overhead manageable while reaching families who needed the service.
The HYBB Difference: A Caddy, Not a Salesman
Greg described Terry's role with a simple analogy.
"He's sort of like a golf caddy. He may understand the terrain and the distance and the wind and which direction it's blowing and how hard, but ultimately you're the one who has to take the swing."
What stood out most was that Terry's focus was never on closing a deal. It was on the right fit.
"For him, it's not a transaction. It really is about him being proud of the work that he's doing, that he can look back and say, hey, I helped this person change their life, change their career."
Greg was direct about the outcome: "Without Terry, I will say that I don't see a scenario where I would have landed on British Swim School. But I can honestly say that I can't think of another franchise that would have been a better fit for me."
Family, Lifestyle & Building a Legacy
For Greg, this wasn't only about income or independence, though both mattered.
"To be your own boss, you're ultimately accountable to yourself, which comes with its pressures but also its freedom."
His decades of leadership experience in customer service and IT gave him a foundation to build on. But the deeper motivation was always his son, and the chance to build something tied to community and legacy rather than a paycheck.
The Outcome
Greg's first territory choice hit a snag: he couldn't secure the pool partnerships he needed. Rather than force it, he pivoted to a different territory, one with stronger options, including a partnership with a local LA Fitness that welcomed the business with open arms.
Through the HYBB process, Greg:
- Evaluated multiple franchise concepts before narrowing to two finalists
- Chose British Swim School for its 45-year history and life-saving mission
- Built out a territory with strong pool partnerships after an early setback
- Launched with an experienced aquatics manager and swim instructor
- Reached 36 students and climbing within a month of opening, with more inquiries coming in
- Is now planning future partnerships with hotels, senior centers, and fitness centers to expand access across the territory
"Without Terry, I don't see a scenario where I would have landed on British Swim School. I would absolutely recommend him to anyone that's looking at franchising. I think he's just one of the best in the business, if not the best."

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