Prospecting Can Be Fun: How not to become “the Roth IRA guy”

Prospecting is part of the job for every advisor and every business owner. If you want a healthy pipeline, you’ve got to keep meeting people.  

But over the past two decades I’ve realized that prospecting doesn’t have to feel like pitching. And if it does feel like pitching, you’re doing it the hard way. 

Very early in my career, a good friend gave me feedback that changed everything. He said “Todd, every time we get together, you’re always talking about Roth IRAs.”  

And the truth is… he was right. 

I love Roth IRAs. I still do. But I realized I was starting to become that guy—the one who walks into a room and people think, “Oh great, what’s he selling now?” 

That’s the fastest way to kill relationships before they start. 

I want people to know what I do, but I never want them to feel pressured. 
No hard sell. No pitch mode. When the time is right, they’ll come to that conclusion on their own. 

My approach: do things I’d do anyway 

Here’s the trick that made prospecting feel natural: 

I got involved in things I already cared about, things I’d do regardless of my career and, over time, they started to be a source of new clients.  

A month after I graduated college, I went to my first College of Business alumni meeting at the University of Central Florida. I loved my college experience. I love cheering for the football team and supporting the program. So being involved made sense. 

It took years before that involvement turned into actual clients, but it was never wasted time, because I enjoyed it and I was building real relationships. 

Another example is my kids’ elementary school. I’d be involved in their school no matter what I did for work, but about a year ago, the school president started a professional dads group.  

We meet monthly. It’s dads in different fields, and it’s turned into a real networking and business development community. It also supports the school, because members donate to be part of the group. 

Again: win-win. 

When you meet people inside a community you genuinely care about, trust forms differently. You’re not a business card. You’re a real person. 

And when someone eventually thinks, “I need financial advice,” they don’t start from scratch. They already know you, they already trust you, and they already understand what you do. 

That’s the softest (and strongest) form of prospecting I know. 

Charitable work: where relationships get real 

One of the biggest impacts in my life came from a local organization working with inner-city kids near downtown Orlando. 

I learned about it in college, before I even knew what career field I’d choose. It was a Saturday morning tutoring and mentoring program for elementary-aged kids. I went… and I kept going. 

For 10 straight years, every other Saturday from 9:00 to 12:00, I showed up. 

Over time, I realized many of the other volunteers were business owners, doctors, attorneys; exactly the type of people I’d want to know in any world. 

But I wasn’t walking around handing out business cards. I was working beside them, serving kids, showing up consistently. They got to know me. They trusted me. And yes, clients came from those relationships. 

Even more meaningful: staying in touch with some of those kids, who are now grown adults. That’s the kind of “return” you can’t measure on a balance sheet. 

Toastmasters: networking without trying to network 

Another surprise for me was Toastmasters. 

I joined a local group eight or nine years ago because I’ve always enjoyed public speaking and wanted to improve. The goal of Toastmasters isn’t networking; it’s becoming a better speaker. 

But networking happens anyway because people share real stories. In speeches, you hear sincere, personal details you’d never get at a typical business breakfast. 

In my first speech, I unexpectedly got emotional and started crying while telling part of my story. That’s not something I’d ever plan, and it’s definitely not something you’d reveal in a first “professional” meeting. 

But afterward, people connected with me on a deeper level: 
“I went through that too.” That’s relationship-building that goes beyond surface-level “what do you do?” 

The bottom line 

A lot of people start out thinking prospecting means going to every networking breakfast in town and collecting a stack of business cards. 

Sometimes that works. But often it’s repetitive, transactional, and exhausting. My approach is simpler; prospect where you already belong. Do what you genuinely care about and show up consistently. 
Let people learn who you are without feeling sold to. 

When you build trust the right way, business becomes a byproduct, not the point, and prospecting is all part of the fun.  

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