Dynasty CEO Shirl Penney: Focus on Being Unique in a Complex World

The more things change, the more they stay the same.

In less than a decade, the financial planning industry expects to be short roughly 100,000 advisors due to a massive retirement wave. At the same time, the US has gone through one of the greatest eras of wealth creation in history. “There’s more wealth and fewer advisors to service it,” said Dynasty Financial Partners CEO Shirl Penney. 

Meanwhile, artificial intelligence and other technological advances are giving advisors new ways to scale their businesses. But advisors also need to remain focused on what makes their firms unique. Technology can help them serve more clients, but the human element of financial advice remains irreplaceable, Penney told Advisor Upside.

We caught up with Penney at the Charles Schwab Impact conference in Boston last week to discuss the talent shortage in the advice industry, how to avoid distractions in a complex world and the continuing cyborging of financial planning.

When we spoke in 2024, you said advisors’ biggest challenge was tech and that the future of financial planning was becoming more “cyborg” because of advances in AI. Since then, have your thoughts changed? What’s come true, and have things evolved beyond what you were expecting?

All of those things are still true. The list could go on and on, right? You’ve got cybersecurity related issues, you’ve got geopolitical issues, elections, markets. So I think the biggest challenge facing advisors right now is the complexity of the world that we’re living in and all the things that they have to focus on, while also focusing on taking better care of their clients and running their business. 

The way that you solve that is by getting a list of your top six, seven, eight priorities down on paper and then narrowing it down and saying, “OK, what are the one or two things that are truly most important for my business?” And that’s where I’m going to spend my time and attention and outsource — whether it’s to another team member, if you’re a leader of one of these businesses, or to a resource partner in the ecosystem — items four through seven. Focus on the things that make you uniquely you, because the world is going to continue to get more complicated, not less.

What are advisors’ biggest distractions?

We’re at the Schwab Impact ’26. It’s incredible to see the growth of the ecosystem. And while that’s amazing, there’s also so much more choice. If you look at all the new technology vendors that are coming into the space, new and innovative asset management capability, it’s hard to focus on all of that while also focusing on your employees, your brand, the business and taking care of your clients. 

Those who can get really focused on what makes them unique and tech-enable their business so that if they service 200 clients today, they can serve 400 clients tomorrow with the same level of touch and service, they’re going to grow massively disproportionately because the opportunity is so huge.

We always like to ask, what’s something no one is talking about or you think advisors should be paying more attention to?

Well, it’s starting to be talked about more, but the shortage of talent that we have in the industry. There’s a lot of conversation around AI, and like you mentioned we had talked about the cyborging of the industry. That’s continuing to accelerate, but at the end of the day, a human providing advice to another human is not going away. There are important moments in life where you really need an advisor, whether it’s the start of a new career or the ending of your career, the sale of a business, hopefully you’re not going through a divorce or you have a sick loved one, and all of these things that are so human. You want to sit and talk to another individual who has empathy, understanding and proximity to what it is you’re dealing with. And then the technology allows for implementation of it.

We’re trying to bring more of our [military] veterans into our industry, trying to help people transition from other careers, trying to inspire young people to understand that this is an incredible profession where, at its core, you can help people.