How to Build Loyal Clients (and Why It Matters More Than Ever)

A few weeks ago, I spent several days up in Canada, mixing business with a little golf. If you’ve ever been to Northern Ontario, you know how stunning the wilderness can be—dense pine forests, endless lakes, and some of the best fishing you’ll find anywhere. But let’s just say, my experience in the cities especially on the golf course left a different impression.

As a financial advisor and business owner, I’m always observing. What makes people tick? What drives loyalty? Why do some brands earn lifelong customers while others don’t get a second chance?

On this trip, I had a few unexpected experiences that taught me valuable lessons about business, marketing, and how we can all do a better job at building and maintaining loyal relationships with our clients.

When Too Many Rules Kill the Experience

Let’s start with golf. I shelled out $250 to play a highly rated course in Toronto. We were greeted by a starter who told us about the day’s conditions it had rained, so we could only go 90 degrees across the fairways, not the usual direct driving. Fair enough. But then he hit us with the kicker: “You’ve got 12 minutes per hole. If you fall behind, we’ll ask you to skip ahead.”

Wait, what? I had three women in my group, one wearing a walking boot after recent foot surgery. The last thing we needed was to be rushed. And here we were, on a premium course, being pressured like we were late for a flight.

Lesson: Experience Is Everything

No one likes to be micromanaged especially when they’re paying for a premium service. Whether you’re on the golf course or in a financial planning meeting, rigid rules can ruin the experience. Clients want structure, yes but more than that, they want flexibility, empathy, and understanding.

A Detour Worth Taking: Memories, Beer, and Missed Opportunities

On my way to another course, I saw a sign for Guelph, Ontario home of Sleeman’s Brewery. It brought back great memories of fly-in fishing trips with my buddies, where we’d load up coolers full of Sleeman’s bottles and spend the week in nature.

So I took a detour. I expected a great experience at the brewery. Maybe some gear, a cold beer on tap, and a chat with someone passionate about the brand. Instead, I found a lonely gift shop staffed by a bored young woman. No t-shirts above size 1X, no hoodies, no koozies—nothing for a guy my size. I left with two mugs and a case of beer, but also with disappointment.

Lesson: Know Your Customers

If you’re in business, any business, you have to know your clients. Sleeman’s missed an opportunity to deepen brand loyalty. No gear for bigger guys? No one excited to share the story of the beer? That’s not how you build raving fans. Make your brand about connection, not just the product.

Harley Davidson, Making Noise, and the Power of Identity

At a business event on the same trip, I heard keynote speaker Ken Schmidt tell the story of how he helped rescue Harley-Davidson from the edge of bankruptcy in the 1980s. His strategy? Stop selling motorcycles. Start selling lifestyle.

When a Harley pulls up next to you at a stoplight, the rider revs the engine. Loud. On purpose. That rev is saying: Look at me. Notice me. According to Schmidt, that’s human nature. We all want to be noticed for our work, our style, our values. Harley tapped into that desire and created a brand that stands for freedom, rebellion, loyalty, and identity.

Lesson: Sell the Emotion, Not Just the Service

Harley riders customize their bikes. They take off the mufflers. They make it their own. That kind of loyalty doesn’t come from horsepower, it comes from heart.

As a financial planner, I’m not just giving advice. I’m helping people feel secure, confident, and in control of their financial lives. That’s my “Harley sound.”

So, What Does This Have to Do With Financial Planning?

Everything. Every business, whether it’s motorcycles or wealth management, depends on loyal clients. Not just satisfied clients—loyal ones. The kind who refer friends, leave reviews, stick with you through market downturns, and look to you for the long haul.

I’ve built my practice over decades by focusing on these four things:

1. Delivering Exceptional Service

You don’t rush through a client meeting like it’s 12 minutes per hole. You listen, guide, and give them your best.

2. Adding Personal Touches

Whether it’s sending this monthly newsletter, checking in after a milestone, or remembering their favorite vacation spot. Details matter.

3. Creating Real Relationships

People don’t stay loyal to faceless brands. They stay loyal to people they trust.

4. Always Improving

Even at 60, I still attend conferences, read books (like Schmidt’s Make Some Noise), and look for ways to get better. Because you deserve that.

Actionable Takeaways for Your Life and Business

Here’s what you can do with all this:

• Look at your own experiences as a customer. What brands do you love? Why?
• Treat loyalty as a two-way street. Go the extra mile for the people who trust you.
• Be human. Don’t just sell a product or service. Tell your story. Make a connection.

Ken Schmidt didn’t just rebuild a brand, he taught a lesson in connection. Sleeman’s reminded me that memories and loyalty are built through shared experiences. And Toronto golf reminded me that rules without empathy can backfire.

I may have come home with a lighter wallet and fewer souvenirs than I hoped but I came back with new ideas for how to serve you better.