Growing a Dynasty from the Garage Up: An Interview with Shirl Penney

Shirl Penney’s entrepreneurial journey could very well be a movie or a best-seller. He grew up in “the sticks of Maine,” was raised by his step-grandfather, experienced several years of homelessness as a child but never missed a day of school and eventually became the first in his family to attend and graduate from college. His career in finance began with a 16-hour bus trip from Maine to Manhattan, where he interviewed in a suit he bought from the Salvation Army store.

 

By 2010, he had started his own firm, Dynasty Financial Partners. Seeing an opportunity to provide breakaway advisors with proprietary technology, financing and a step-by-step process for becoming an independent firm, Shirl launched his company as a service provider for registered investment advisors (RIAs). Earlier this year the firm filed to go public. 

 

Ahead of the Future Proof Festival, I sat with Shirl to discuss his business philosophy, his passion for horse racing and how he started Dynasty Financial from an office in his garage. 

 

Future Proof: Most Future Proof attendees will know you as the CEO and President of Dynasty Financial Partners, but you describe your wife as the co-founder of your business. What lessons have you learned about business from your wife?

 

Shirl Penney: This is a little bit of a secret I’ll share. My family and I were living in Saratoga Springs, New York, while I was trying to build Dynasty. My two girls were still very little and I was constantly on the phone, trying to raise capital. This was after the 2008 financial crisis, so I was even making trips down to New York City to raise funds. 

 

I came home on one of those trips and my wife took me to the garage. In the corner of the garage she had built this walled-off area that took up about third of the space. It looked like a giant box in the corner of the garage. Even today it gives me goosebumps to think about.

 

I walked over to the box and opened the door. Inside was an office. It had hardwood floors, crown molding, a fireplace and air conditioning. There was a TV above the fireplace. It was gorgeous. 

 

My wife, Mary Ann, built it with her own hands and the help of my father-in-law. She said, “A big-time CEO is going to sit in this office, so we had to make sure it looked nice.” 

 

She read my business plan, helped design the Dynasty logo, the marketing materials and approved all of our first hires. She is the best judge of character of anyone I’ve ever met. She has been more right about talent, in particular, over the course of my career than I’ve been. 

 

Entrepreneurs thinking about starting a new business need to overcommunicate, not just with their partners in the business—but start by overcommunicating at home. The real co-founder of your business is your spouse and sometimes entrepreneurs don’t realize that.

 

Mary Ann teaches me the importance of prioritization and to focus on what’s most important in life. She is also the CEO of Team Penney Racing. 

 

FP: What is Team Penney Racing? 

 

Shirl: Team Penney is a term that we use in our family when my two daughters, my wife and I are doing something together as a family. Team Penney Racing is our own horse racing stable. 

 

FP: What attracted you to horse racing?

 

Shirl: I was captain of the baseball team when I was at Bates College. One of the things we loved to do as a team was go to the horse track. We spent so much time at the horse track we started calling ourselves the track team.

 

I fell in love with horses and decided that I would like to own one if I could afford it. If you’ve ever been close to race horses, they’re absolutely beautiful. And unbelievable athletes. Most of them—but not all of them—are friendly. 

 

Team Penney Racing had some early success about 15 years ago, when we won the Black-Eyed Susan Stakes, and over the years we’ve owned about 125 horses. 

 

Team Penney Racing is also about camaraderie. 

 

We might get 50 to 100 friends and family at a race. For someone who is as busy as I am with work and traveling, to have so many people that you care about—together—for the excitement of the race, is absolutely special. I always say that I’ve won before the gate even opens. 

 

FP: As you advance in your career, are there any lessons that you wish you had unlearned or graduated from more quickly? 

 

Shirl: I was a young man in a hurry. I would tell young Shirl that you don’t have to be in such a hurry. It will all come to you in due course. Truly successful people in life, and in business, are the ones who empower the team.

 

You can be an All-Star individual contributor—and that’s what you are: an individual contributor. It’s better to be a world class leader and to have all the All-Stars on the team.

 

FP: You experienced homelessness from the ages of 11 to 13. Did that experience factor into your need to move quickly as a young professional?

 

Shirl: Absolutely. There’s no greater motivator. I can tell you, firsthand, that being cold and hungry is a heck of a motivator. 

The reality is I’ve been broke twice. Once as a kid, and again when I went all-in on Dynasty. I was not homeless, nor was I hungry, so it was a better form of broke. But there’s no question that adversity builds character. I had a fair amount of it, as a lot of people do growing up.

 

Even so, I always felt loved by my step-grandfather. I always had one person in my life that believed in me. That was huge. 

 

He taught me that your word is your bond. He was old-school and I like to think that I am, too. You don’t need a handshake or a contract. If you say you’re going to do something, you’re going to do it. 

 

It also takes a community to raise a child and I had a great community.

 

FP: You talk about the idea of “staying close to the field” as key to success. What do you mean by that?

 

Shirl: That’s another element I learned from my step-granddad. He was always present. He made sure that I was present. I actually got an award before I left for college: I never missed a day of school from kindergarten to grade 12. 

 

Proximity to a client is critical in any business, but particularly in ours. Most of the innovation and positive changes come from advisors interacting with clients. That’s where the consumer—if you’re listening and not talking—is telling you about what’s most important. 

 

When I meet with clients it energizes me. We have this really cool wall of plaques that celebrates all of the clients we support. It’s right in the lobby. The receptionist chair is across from the plaques, and one of my favorite things to do is sit in the chair, late at night when there’s no one around, and just go across all those plaques and use that time as a way to connect with our clients.

 

I look at my calendar and make sure I’m moving around the country over the course of the year in a way that allows me to meet with each of our clients.

 

There’s nothing like going out in the field; it’s unfiltered.

 

FP: Future Proof is positioned to be an incredible opportunity to connect with others. What are you most excited about for Future Proof?

 

Shirl: I’m excited about the lifestyle perspective that is going to be present. Future Proof is about humanizing our profession. 

 

I think everyone will have a great time, but I hope that the people who aren’t there will see it—and that it encourages them to think differently about this profession. We need more people in financial services. 

 

Whether you’re retiring from the military, are a retiring school teacher or are transitioning careers, we need more people in this profession. It’s an incredible profession where you can make a huge impact on someone’s life. My hope is that Future Proof inspires younger professionals, as well as people in other professions, to consider entering the financial services industry.



John Swolfs Advisor Circle

JOHN SWOLFS

John Swolfs is the Chief Content Officer at Advisor Circle, a product studio for growth-oriented financial professionals. John is responsible for creating dynamic programs for Advisor Circle’s world-class events which include Future Proof festival and Exchange, the world’s leading ETF event.

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Attendee Experience

Investopedia Top 100 Financial Advisor Reception

Monday, September 12, 2022 5:00-7:00pm PT
HYATT REGENCY CALIFORNIA COURTYARD

Future Proof brings together the best and brightest advisors from across the country. This exclusive event allows the Investopedia Top 100 advisors to reconnect, share insights and celebrate their achievement of being named to this prestigious list.

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Scoop Ice Cream Parlor & Lounge

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Get the latest scoop on pivotal industry topics and current events affecting the wealth space. By leveraging our robust event technology, you’ll have the opportunity to create both peer-led and industry-led roundtable-style discussions. Learn more about the most pressing topics impacting the future of wealth. These hard conversations are made easier as you and your cohorts grab some ice cream and settle in for an informal yet highly engaging conversation.

Future Proof Creator Corner

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rhe Creator Corner is built to support creators, creatives and brands. It’s equipped with a podcast recording studio and first-of-its-kind Collab Lab. The podcast area will afford attendees the ability to record podcast sessions and will feature podcast consultants helping to answer questions of both existing podcast hosts and aspiring creators. The Collab Lab is where asset managers and fintech companies collaborate with leading and emerging finance influencers. Looking for engaging content built for the modern financial professional or investor? We offer high quality video and audio production for all your creative needs.

Future Proof Live

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Future Proof Live is our full-production broadcast studio strategically placed at the heart of the Boardwalk. Our very own Future Proof anchors will provide all-day commentary featuring casual speakers and celebrity interviews as well as unexpected guest appearances. Future Proof Live extends our one-of-a-kind experience to a larger audience virtually.

PCH Stage

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The Pacific Highway stage is the most versatile stage at Future Proof. With countless setup options, the PCH Stage is your go-to spot for industry insight and innovation, all while staying current with the latest trends in money, culture, tech and impact.

Ocean Stage

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As the beating heart of the boardwalk, the Ocean stage will feature seating for over 500 and have the look and feel of a concert venue on the beach. The ocean stage will host a range of exciting content from industry-changing keynotes to the closing concert featuring today’s biggest musical acts.

Social Audio Experiment

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Podcasts are all the rage, as they excite and entertain audiences from afar. Future Proof changes the game, as we invite your favorite podcasters to host their shows live from the festival. Forget passive listening. Future Proof’s Live Podcast sessions allow you to interact directly with your favorite podcast creators as they record live episodes just feet from the Pacific Ocean.

Brewing Lounge

Coffee bar on Huntington Beach

You can’t expand your perspective and think differently if you aren’t exposed to a broad perspective. That’s why our speaker faculty isn’t limited to traditional finance. The Brewing Lounge will bring out-of-industry experts to present their visions for a new world of wealth. To help fuel the conversations, we’ve created a true coffeehouse feel complete with baristas just waiting to pour you the perfect cup of joe.

Poppin’ Pitch Lounge

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Nobody likes to be pitched, but the truth is we all need a little help keeping up to speed on our dynamic industry. The What’s Poppin’ Pitch Lounge sets the tone, giving you intimate access to short and punchy demos from the most innovative fintech companies in the world. Grab a bag of popcorn, sit back, relax and absorb the next wave of innovation impacting the world around you.

Wheel of Impact

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Future Proof’s Wheel of Impact promotes the power of giving in a fun, dynamic and social way. With a donation of any size, attendees can have the ability to spin the wheel, determining where the donation will go and how it will be used. Land on the “mystery” selection and have a chance to win items, trips and other experiences.

RIA Executive Leaders Reception

Monday, September 12, 2022 6:00-8:00pm PT
Pasea Hotel & Spa

Join 30+ executives from the country’s top-ranked RIA firms for a VIP evening reception.


If you are an executive leader (or owner) of a fast-growing RIA firm and are interested in participating get in touch with us today. Space is extremely limited.

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"Future Proof Closing Night Concert" to become "Future Proof Music Festival"

Tuesday, September 13, 2022 4:30-10:00pm PT
The Future Proof Boardwalk (Outdoor Event Space)

The Future Proof Festival experience roles on as we host our annual music festival. This year’s lineup features an array of artists and musicians covering everything from rock classics to hip hop. Come early and stay late sampling the numerous food trucks and bars. Don’t miss headliners rap legend Big Boi and indie pop sensation Fitz and the Tantrums showcase their talents.* * admission is included with your Future Proof Pass.

"Future Proof Beach Bash" to become "Future Proof Festival Kickoff Party"

Hyatt Regency Huntington Beach Resort

Relax and unwind as you connect with the Future Proof community, as you enjoy and evening of tasty bites, and delicious cocktails as celebrity DJ, DJ Mick sets the vibe as the sunsets on the beautiful Pacific Ocean.

Health Is Wealth Center

Yoga mats laid out for workout

Physical and mental health is the cornerstone of any successful long-term wealth plan. But for years, our industry has prioritized work over health, leading to unhealthy lifestyles and employee burnout. The Health Is Wealth Center provides a warm and relaxed setting, allowing attendees to come in and recharge, grab a drink from the juice bar and eat healthy snacks. The space will also be home to daily group yoga and fitness classes as well as meditation sessions.

The Grand Unveil

The Future Proof Boardwalk (Outdoor Event Space)

Future Proof does nothing small. Join us on Monday morning for the grand unveiling of our half-mile beachfront boardwalk complete with activations, meeting areas, multiple stages, and everything else you need to make your Future Proof experience truly one of a kind.

ONYX Advisor Network Meet Up

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Health is Wealth: Surf Lessons

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We are in Surf City U.S.A – of course we are going to have surf lessions. Whether you are catching barrels are just learning to stand come out be part of the community and tick learning to surf off your bucket list.

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Media-Only Networking Reception

Sunday, September 11, 20226:00-8:00pm PT
Monday, September 12, 20226:00-8:00pm PT

Join 25+ key financial media, industry reporters, and other press for a media-only evening reception.


If you are a member of the press and are interested in participating get in touch with us today. Space is extremely limited.

As a member of the press, you will have the opportunity to RSVP for both receptions on Sunday and Monday.

Advisor Networking Dinners

Sunday, September 11, 2022 6:00-8:00pm PT Monday, September 12, 2022 6:00-8:00pm PT

Maximize your time at Future Proof by participating in a 10-person advisor networking dinner organized by us and industry partners. Held at popular downtown Huntington Beach restaurants, our organized Advisor Networking Dinners will provide you with a one-of-a-kind culinary experience while making new friends and catching up with old ones. Space is extremely limited. Must RSVP.

Health is Wealth: HIIT

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Just because you are away from home it does not mean you need to miss your workout. Start each day with a HIIT beach workout hosted by the Future Proof communities Jess Bost. * space is limited, preregisteration required

Health is Wealth: Yoga

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Future Proof puts a value on your health and ability to decompress from the grind of festival life. Begin your day with a focus on centering body and mind for a day of meetings, networking, and more.

Health is Wealth: Meditation

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Your mental health is as important as your physical health. Set the tone for each day as you take the time to relax your mind, center your thoughts and prepare yourself for the day ahead.

Storyteller Series: This Is Not Financial Advice

Sunday, September 11, 2022 6:00-6:30pm PT
The Future Proof Boardwalk (Outdoor Event Space)

Investing has become mainstream and nowhere is this better encompassed than in the new documentary film This is Not Financial Advice. Join us as we invite the cast and crew for an open conversation on the mindset of today’s investors, and take a closer look at investing as a cultural phenomenon and show clips from the movie.

All Access: Fitz & The Tantrums

The Future Proof Boardwalk (Outdoor Event Space)

Join your fellow peers for an all access experience with indie pop sentation Fitz and the Tantrums. This excluisve event is a can’t miss experience for any music fan.

FintechX Demo Drop

The Future Proof Boardwalk (Outdoor Event Space)

Social Audio Experiment:
EYL Presents Market Mondays

The Future Proof Boardwalk (Outdoor Event Space)

Cultural icons and financial influencers Earn Your Lesuire host their wildly popular Market Mondays Show live from the Future Proof stage. This can’t miss sessions ties together market events and education to help investors be better invested.

Social Audio Experiment: Bloomberg's Masters in Business Live

The Future Proof Boardwalk (Outdoor Event Space)

Hear podcast legend and host of Masters In Business Barry Ritholtz for a can’t miss live recording of the most influential podcast covering the world of business.

Social Audio Experiment:
Invest Like the Best Live

The Future Proof Boardwalk (Outdoor Event Space)

Recgonized as one of if not the most influential podcasts Invest Like the Best records live from Future Proof. Join host Patrick O’Shanunessy and his guest for indepth look at the markets, investing and the world of business.

Social Audio Experiment: Bloomberg Sports Live

The Future Proof Boardwalk (Outdoor Event Space)

The world of sports is more than just the games. In this unique session, Bloomberg Chief Corresponded Jason Kelly hosts financial advisorJoe Mclean and his superstar sports clients for an in-depth look at the changing world of sports and why more athletes are embracing investing and building wealth beyond the court.

All Access: Big Boi

The Future Proof Boardwalk (Outdoor Event Space)

Future Proof is all about experiences. Rub shoulders with Big Boi in this invite-only meet & greet in the Future Proof green room.