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Each year, the top thoroughbred racehorses in the world - along with their owners, trainers, jockeys and their racing teams - tirelessly train, prepare and gear up for what is known as ‘The Most Exciting Two Minutes in Sports’ – the Kentucky Derby. During those two minutes, the horses will race their way around the oval of the track, charging through furlong after furlong, where eight furlongs total a mile. On Around the Track, the Most Exciting 15 Minutes in Wealth Management, our guests are asked a series of eight rapid-fire questions, symbolic of the eight furlongs comprising the typical track.

Around the Track allows Shirl to combine two of his passions into one - the wealth management industry and his love for the sport of horse racing. Shirl will host top' corporate athletes' - Dynasty Network advisors and some of the top business leaders and entrepreneurs in wealth management and beyond - to discuss how they have gotten to where they are now and what their next "Kentucky Derby" or big goal might be.  

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Around the Track Races

Ep. #6: Lisa van Walleghem

CEO & Founder of MAXIMAl Investment Partners

We may not be racing horses, but the Dynasty Community is always up for a friendly competition. Find out who has the most views this month with the
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And They’re Off!

Welcome to Around the Track hosted by Dynasty CEO, Shirl Penney. Get ready for "The most exciting 15 minutes in Wealth Management!"

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Ep. #3: Jason Fertitta

President of Americana Partners

Ep. #5: Michael Rose

Managing Partner of Rose Capital Advisors

Ep. #2: Ed Swenson

Co-Founder and COO, Dynasty Financial Partners 

Horse Racing – A Penney Family Tradition

Ep. #1: Alan Harter

Founder and CEO of Pactolus

“When I captained the baseball team at Bates College, the team always had an affinity for going to the horse track. You would think a group of competitive college athletes would be going for the gambling or a cold beer, and for some, that was certainly a draw, but for me, I was more fascinated by the sport itself and the athletes running around the track. I just loved the horses and the characters on the backstretch. Back then, I thought someday, if I could afford it, I would own a Thoroughbred racehorse.” – recalls Shirl of when his interest in racing was born.

Initially dipping their toes in the water with syndicate involvement, Shirl and his wife and CEO of their racing and breeding stable, Mary Ann, launched Team Penney Racing in 2004. Over the years, they have won some of the top races throughout the country, always with lots of family and friends in tow. Away from his work at Dynasty, Shirl and his family have centered their lives around horse racing. They raised their two daughters in Saratoga Springs, New York – home to the oldest racetrack in the country – before moving Dynasty to St. Petersburg, FL, where the family can now be found racing their horses at Tampa Bay Downs. 

Shirl, Ann Clare, Mary Ann and Townsend Penney with their star mare Flipcup

“I feel racing has been a wonderful escape for me over the years. Being with the horses and with my family and friends has been amazing as it’s a great way to get people together to cheer for your horses. Having everyone together, I feel like I have already won before the gates even open,” reflects Shirl.

Over the years, Shirl and Mary Ann’s passion for racing has grown, as has the number of racehorses in their stable. Shirl has shared his passion with his partners at Dynasty, Dynasty’s RIA team members & their clients, and countless resource partners with trips to the track and group photos in the winner’s circle becoming a common Dynasty outing. Dynasty’s annual client event at the Kentucky Derby, complete with tickets in the “Mansion” high above the finish line, is one of the most popular advisor and client events at Dynasty.

Ep. #9: Katherine Forrester Schneewind

Founder & CEO, 

High Note Wealth



Ep. #4: Tom Durkin

Former Race Caller for NBC Sports & the New York Racing Association

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Ep. #8: Marty Bicknell

CEO & President of Mariner Wealth Advisors

Ep. #7: Steve Tenney

Founding Partner & CEO of Great Diamond Partners

Ep. #9: Katherine Forrester Schneewind

Founder & CEO of High Note Wealth