In this candid conversation with Kevin Leahy, President & CEO of Connecticut Wealth Management (CTWM), we explore the pivotal moments and hard-won lessons behind growing a business from a small practice into a thriving one.
Kevin shares what many business owners eventually discover: scaling isn’t just about growth. It’s about shifting your mindset, building the right team, and learning to lead in a new way. From taking big financial risks to making tough personnel decisions, his insights offer a window into what it truly takes to build a lasting, value-driven business.
Q: Was there a moment when you realized CTWM had become more than just a small practice?
The concept was always there: comprehensive planning, working as a team, fee-based, not selling products. But in the early days, I never imagined more than a small group of people serving a small group of clients.
It wasn’t until we hit around 20 people that it clicked: this is a real business. We were steadily attracting new clients and teammates. Sometimes that felt easy; other times we wondered if we’d ever find the right person.
With growth came complexity. We needed professional financial management, HR, and benefits, things I hadn’t considered at the start. That’s when my thinking shifted from “let’s hire one more person” to “we need professionals who are businesspeople, not wealth managers.” I began to see hires not as a cost, but as an investment.
Once you’ve navigated that yourself, you start to spot the same growing pains in the businesses you serve, even before they do. In many ways, we are the people we serve; we just happen to run a different kind of business.
Q: From the outside, it seems like you’ve had a strong team—but did you ever feel like you were carrying the weight alone?
It depends on the day. Some days, I feel the full weight—the buck stops with me. If something goes wrong, it’s mine to own. And when things go really well, often I benefit first, which is great but also a little strange. I get why people say, “It’s lonely at the top.”
That said, I’ve never truly been alone. In the early days, my co-founder Denis and I made most of the decisions together. Others were part of that too, but when you’re small it’s hard to see past that particular moment. Decision-making can get messy. Sometimes no one acts; sometimes everyone acts at once.
One of the biggest long-term challenges has been figuring out what each person, including myself, is best at. Early hires wore a lot of hats. As we grew, we became more intentional about putting people in roles where they thrive and bringing in new talent when needed. Denis is a perfect example of this. As a founder, many people think he must be involved in the day-to-day operations. He has a gift for building external relationships, so not only would we be foolish to take him out of a role in which he excels, he’d likely be less happy too.
Hiring early on was mostly a gut feeling, which was wrong sometimes. Today, I’d like to think we hire with more precision, making sure candidates excel at what we need and fit our culture and values.
Q: What were some of the biggest risks or challenges early on—and what helped you push through?
The biggest challenge was making the leap. I had a good job, good pay, and stability. But it wasn’t fulfilling, and we couldn’t build the kind of company we envisioned.
So, I left that behind and borrowed over $2 million to start something new—with no guarantee of success. I remember telling my wife to open those credit card offers we usually tossed, just in case we needed backup cash. She’s not a risk-taker, so that was a big, scary moment for both of us.
Looking back, it sounds like a great origin story. But at the time, it was terrifying. As I sit here today, that experience gave me deep empathy for people who take real entrepreneurial risks. And the rewards, far beyond financial ones have been worth it.
The harder, less obvious challenge was learning how to lead and manage people. I thought I was communicating clearly, but I wasn’t. We had a great model, but aligning a team was messy.
Over time, I learned you can’t live with underperformance, and you definitely can’t live with cultural misfits. Once you see it, you can’t unsee it. Sometimes, the best thing you can do is make the hard call. That’s how you build a team of A-players, and our clients and colleagues deserve nothing less.
Q: What’s one question every business owner should ask themselves?
Ask yourself: What’s my vision?
Not just your mission, like making a great product or delivering top service, but the bigger picture. What do you want the company to become? What should it look like in five or ten years? And why?
For us, it started with serving clients and creating a good life for our families. In the early years, Denis and I probably thought about the “finish line” as the end of our careers. Now, that vision has evolved. We want the firm to continue turning life’s aspirations into reality for clients and teammates long after we’re gone.
The challenge is too many business owners are stuck in the daily grind and never stop to ask: What’s the point? What’s the end game? Asking “What’s the vision?” is a powerful place to start.
Q: What’s the best piece of advice you’ve received as a business owner?
Get the right people on the bus, the wrong people off the bus, and make sure everyone’s in the right seat.
It all starts with who’s on your team. With the right people, things flow. Without them, even simple things feel hard.
Equally important: culture is king. Culture affects everything that goes on in an organization and is reflected in its people. The right culture supports the right people and helps the business thrive, even in hard times. The wrong people, even if talented, can quietly hold you back. Letting go of someone who is talented but not the right fit is one of the hardest parts of leadership, but it’s necessary.
No amount of technology or processes can replace what moves the needle most: people and culture.
Wrapping Up
Kevin’s story is a powerful reminder that building a business isn’t just about scaling—it’s about evolving. Growth requires clarity of vision, the right people in the right roles, and the courage to make hard but necessary decisions.
CTWM didn’t become a business by accident. It became a business by design: one decision, one risk, one lesson at a time. For fellow business owners, the takeaway is simple but not easy: Keep asking the big questions. Stay focused on the people. And remember, culture isn’t just a buzzword. It’s the foundation of everything that lasts.
Interested in learning more about how we help business owners navigate growth, succession, and beyond? Contact us today!