Penney Wise: Q&A With Dynasty Financial Partners CEO, Shirl Penney

Daniel P. Simon

Daniel P. Simon


If you’re ever tempted to doubt the power of the American Dream, or feel the odds too stacked against you to succeed, consider Shirl Penney. Penney, 38, is the founder and CEO of Dynasty Financial Partners, a game-changing integrated platform of technology and services for top independent financial advisors. His rags-to-riches life story is too incredible to do justice in a single paragraph and will be the subject of another article (and no doubt book and movie).

Penney rose from incredible poverty, the kind of poverty we like to believe no longer exists in the developed world, to become one of the youngest directors at one of the world’s largest financial firms. Then, he become the successful CEO and founder of Dynasty with a blue chip client roster and a board of directors that reads like the who’s who of Wall Street.

Simon: Your personal backstory obviously shaped so much of who you are today. What specifically did it teach you about successful entrepreneurship?

Penney: I think adversity sometimes builds character. We all face adversity in our lives, just some of us earlier in life.  It helps define and shape our character.  In my case, it also helped me build a very strong self-confidence early in life and, when I realized I could get through difficult obstacles, it allowed me to grow and be ready for the next ones.  I remember people saying to me when I was raising capital for Dynasty that I am facing enormously difficult odds in raising money for a new model in financial services right after the financial crisis.  I remember thinking my life has been a battle against the odds, so what’s one more battle?  My step-grandfather who raised me was a rough and tough man who had not spent a day of his life when he was not poor. But he taught me some valuable lessons that have served me well about integrity and commitment. If you say you are going to do something, your word is your bond and when someone needs you and is counting on you, then stand and deliver and surround yourself by those that would do the same for you. That is the core of what defines family and a team that acts like a family.

Simon: One of the things you obviously learned growing up was work ethic and today you still routinely work 16-18 hour days. Today, we hear so much about the importance of working ‘smart’ but how important (or unavoidable) is working hard?

Penney: If you spend time with top entrepreneurs, the very best ones often have insane work ethics.  No one outworks me.  I got that growing up dirt poor in Maine.  I worked various jobs that were hard manual labor from when I was 11-12 years old.  Sure, we have smart people at Dynasty, but we also have the hardest working team in space. When you can teach people to be very efficient, prioritize the things that matter, have a common purpose, and layer over that a culture of accountability, good things happen.

Simon: You started your career inside some of the largest firms on Wall Street. What surprised you most about going it alone to found Dynasty?

Penney: I went from one of the largest financial firms in the world to my garage!  All my friends who were successful entrepreneurs told me it would be harder than I ever imagined and they were right!  When you go out on your own, your business card has just your name on it. Period. And to a certain extent what you did in the past does not matter.  Raising capital, attracting people to make your vision theirs, convincing clients to come onboard early, managing expectations at home, and not wavering on your belief in yourself can be difficult.  In my case, it took 2.5 years to raise capital, get the founding team in place, launch the business and sign up our first clients.  Then, when you launch, it gets harder!  Those first five years (2.5 pre-launch, and first 2.5 years post launch) were incredibly difficult.  Much harder than I imagined and, frankly, I think a huge barrier to entry for us as I don’t know too many people as crazy as we were to do what we did!

 Simon: In order to scale their great ideas, entrepreneurs need to partner with and ultimately hire people. How difficult was this for you? What did you learn about picking the right people to collaborate with?

Penney: One of the other things I learned about growing up in a small fishing village in Maine is the value of community.  We have been focused on building a first rate community from day one at Dynasty.  We are defined by the quality of people at Dynasty, our investors, our strategic resource partners, and our clients.  We spend time thinking about how is this client or new partner we are hiring going to be additive to our collective community.  We have an acceptance committee to review new teams we onboard to Dynasty network, our employee interviews take forever as we want to socialize them throughout entire firm, and we do a tremendous amount of due diligence on new resource partners before adding them to our platform to be used by our clients.   When you are trying to build a company with a premium brand in its space, controlled growth that allows quality control is very important.

Simon: You made a deliberate decision to offer your staff equity in the business. Why was this important to you and how do you think it has helped the firm grow? (Do you for example have a good retention rate, higher employee engagement etc.?)

Penney: Equity ownership is a core part of our culture at Dynasty.  While our Board of Directors has been a significant source of capital in Dynasty via their personal investments, almost all employees at all levels at Dynasty have bought equity in the firm.  We also have a generous equity program that rewards commitment over time, client service, and driving results.  People at Dynasty spend money like it’s their own because it is!

Simon: You’re still relatively young for the CEO of a successful company. Has that impacted your ability to hire and grow people? Presumably a number of your employees are much older than you?

Penney: I am 38 years old now and starting to get a few grey hairs so want to hold on to that young CEO thing awhile longer!  I am sure when people heard my pitch at 31 years old, when I started this journey, some people may have thought I was young or crazy or both!  Winners surround themselves with other winners and I only surround myself with positive forward-looking people so maybe I just ignored any negatively in my career because of my age as I was always a young man in a hurry.  That said, I have always found that sophisticated people (clients, partners, employees, investors, etc.) evaluate people based on their competence and character more than their age.

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