Shirl Penney’s story is the kind of American Dream narrative that feels almost too remarkable to be real. Raised in a tiny fishing village by his step-grandfather, Penney’s childhood was defined by struggle. But through his grandfather’s sacrifice, his relentless drive and a belief in the power of education, he built himself into one of the most influential figures in wealth management today.
As the founder, president and chief executive officer of Dynasty Financial Partners—a firm with a network of Registered Independent Advisors overseeing more than $150 billion in client assets, today—Penney isn’t just a business leader. He’s a visionary, reshaping the independent wealth management industry.
Bridgette Bello, publisher and CEO of Tampa Bay Business and Wealth, interviewed Penney in front of a live audience at American Stage, in St. Petersburg. This interview has been edited for length and clarity.
See photos from the event here.
What’s it been like being on the cover of Tampa Bay Business and Wealth this month?
You all did an amazing job—thank you. I’m 48 years old and, for the first half of my career, I was uncomfortable sharing my personal story. I didn’t think I needed therapy or anything; it just felt self-serving. A mentor once told me, “If you tell your story, it will inspire more people,” and that stuck with me.
When we sat down at Urban Stillhouse, it was such a comfortable conversation. You and your team absolutely nailed it. The best part has been hearing from people who say it helped them. We all face adversity at different times. If sharing my experience helps even one person, it’s worth it.
This room is full of CEOs and business owners who could benefit from your experience. One of those areas is raising capital. What’s that like?
I’ve done it well and I’ve done it not-so-well. I became a first-time CEO at 32. I worked on Wall Street and was lucky to learn from legends like Sandy Weill and Jamie Dimon. But when we left to start Dynasty, my wife and I went two years, seven months and four days without a paycheck. If you want to take the island, you’ve got to burn the boats.
We raised capital from individuals who let us keep control. My board chairman is Harvey Golub, former CEO of American Express. Our early board was a Who’s Who, but not everyone ended up being the right fit. One of the hardest parts of scaling a business is having tough conversations with good people, especially if they’re friends. At one point, seven of my college buddies worked at the company and, over time, I had to let some go—even godparents to our kids.
You have to make decisions based on what’s best for the company and you’ve got to hold on to control as long as you can. Every other entrepreneur in my peer group, 15 years ago, gave up too much too early. Now we’re backed by some of the biggest names—JPMorgan, BlackRock, Schwab—and we’ve kept that control. That’s key.
I remember you saying you came here for Tampa but fell in love with St. Pete. Can you talk about that?
We were touring the Tampa Club and someone pointed across the bay and said, “That’s St. Pete,” then joked that it’s basically like New Jersey to New York. I laughed. I actually lived in New Jersey. My wife’s a coal miner’s daughter, from West Virginia, and I’m from a small fishing village, in Maine. That metaphor didn’t quite work on us.
So, we changed our flights, visited St. Pete the next day and immediately fell in love. We still spend time in Tampa—we have great friends there—but St. Pete gave us what I call a “big business hug.” Everyone—city officials, other business leaders, the media—was so welcoming.
You’ve talked about the importance of choosing the right partners. What do you look for?
We were very intentional naming the company Dynasty Financial Partners. “Dynasty” represents winning over time, “financial” grounds us in our industry and “partners” reflects how we treat everyone—clients, vendors, teammates.
We don’t allow the word “vendor” at our office. Everyone is a “resource partner.” Partnership means mutual wins and that’s the only kind of relationship that’s sustainable. That philosophy has been core to our success.
Let’s talk about your daughters. You grew up in poverty. How do you instill that same grit in your kids when they’re growing up with privilege?
Great question. Honestly, you can’t fully replicate that experience and you shouldn’t want to. My wife has a great phrase—we give them the “gift of want.” They have to work for things and we emphasize values over stuff.
They volunteer, they’ve been on mission trips and they’ve seen where I grew up. But being cold and hungry is a whole different motivator. You can understand hardship intellectually, but it’s not the same as living it. So, we focus on experiences, love and building character through effort.
You also put a lot of focus on team building. I remember how your entire team visited St. Pete before the move. Why was that so important?
One of our philosophies is “success is best when shared.” At some point, you have enough success and then you ask yourself, “Why keep pushing?” For me, it’s about impact.
When we were evaluating the move, we broke the team into groups—young professionals checked out the social scene, families toured schools, others explored the arts. We curated field trips. It was amazing. More people wanted to move than I expected, which forced some hard conversations, but also led to healthy turnover.
Since moving, we’ve hired 150 people, many from top companies like Google, Bank of America and JPMorgan. We’re up to 35 open roles right now.
You said earlier that everyone at Dynasty has equity. Why is that important to you?
Everyone—receptionist to executive—owns equity. We’re aligned. Some of our early team members have already retired because of what that equity’s become. That creates opportunity for new talent.
In hindsight, I probably gave away too much equity early on, especially to friends. If I could do it over, I’d tie more of it to performance. But you live and learn.
You’ve brought in big names like Cathie Wood to St. Pete. How do you keep convincing people to come?
I just show them around. When people see the lifestyle, the community, the infrastructure—especially the airport—they’re hooked. I joke that I fly Allegiant to Albany or Bangor for $35. It’s hard to beat.
We’re also investing heavily in tech and AI, but our differentiator will always be our people. That’s what clients value—real advice and service, not just automation. And that starts with a strong, aligned team. ♦
ABOUT ‘CEO CONNECT’
TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. Evara Health Foundation, Source 1 Solutions, Capital Investment Advisors and Home Safety Solutions were presenting sponsors. The host sponsor was American Stage. TBBW’s video partner is Empowering Creative.
The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.
Partnering with TBBW provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.
For information about event sponsorship opportunities, email Jason Baker at [email protected].
