Meet the Group
Cole Gillespie
LPL Registered Administrative Associate
AZ Insurance Lic. # 19662409
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After a professional baseball career of 13 years, including parts of 6 seasons at the major league level, Cole joined Gillespie Group Wealth Management as a licensed assistant and has quickly become a valued member of the team.
Throughout his baseball timeline, Cole was widely regarded as a great team player, detailed, and someone who does things the right way. He brings this same dedication to financial services. Cole helps ensure client needs are met at GGWM while continuing to be an advocate for athletes across the country. His journey is one of perseverance and determination aided by a sound routine and great structure. Cole is in a distinctive position to help many of our athlete clients.
Born and raised in Oregon, Cole chose to stay close to home for college while pursuing baseball at Oregon State University. He played a pivotal role on the National Championship Beavers baseball team in 2006, while also garnering Pac-10 Player of the Year and First Team All-American honors. Later that year, Cole was drafted by the Milwaukee Brewers in the 3rd round, eventually making his MLB debut with the Arizona Diamondbacks in 2010. As a testament to his perseverance, Cole completed his degree at Oregon State during the final couple off-seasons of his baseball career.
Cole resides in Scottsdale, Arizona with his wife, Victoria, and their golden doodle, Rex. In his free time, Cole loves to play golf, play chess, travel, and have friends over for a good old fashioned couples’ board game night.
Sheena Gillespie
Director of Operations
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Having spent 15 years in management and customer service, Sheena (and her husband Brett) decided it was time to put her skills to use at the family business. Sheena is the “glue” for Gillespie Group and as Director of Operations, her responsibilities are many. Her attention to detail, outgoing persona, and smiling greeting face undoubtedly help enhance the client experience.
Sheena’s genuine joy for helping and connecting with others has always been apparent. At her previous employer, where she was a wholesale apparel buyer, district manager, and personal shopper, customers would rave about how comfortable Sheena made them feel. Having seen the yelp reviews pour in over the years, it’s no wonder why Brett recruited her for GGWM.
A proud “Navy Brat,” Sheena has spent most of her life in San Diego, where she also graduated from San Diego State University with a degree in cognitive psychology. She is a lover of animals, a gifted carpenter, an explorer, a writer, and amazingly, has a 5 Star rating on Uber (rare!).
Brett Gillespie
LPL Financial Advisor
CA Insurance Lic. # 0H75550
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Brett founded Gillespie Group Wealth Management after successfully recruiting his wife, Sheena, and his brother, Cole, to form the family business. The vision was, and always will be, to build lifelong relationships, personally and professionally, based on a foundation of trust, candidness, and affability – all within a family environment.
Brett spent the early part of his career with Metlife Financial Planning, then several years with a reputable local firm, Symbio Financial Partners, before opening his own businesses – a desire he has had for many years. In establishing GGWM, Brett has maintained his affiliation with LPL Financial, the country’s leading independent Broker/Dealer, and takes pride in offering high-touch, personalized investment and planning advice to his clients, who range from business owners to professional athletes.
Born and raised in Oregon, Brett ventured to San Diego in 2000 to play baseball and study business at the University of San Diego. Armed with a blistering fastball, a hopeful baseball career ended after some injuries and perhaps to a greater degree, an inability to locate the strike zone! San Diego remains home and GGWM Headquarters to this day.
When not helping his clients pursue their goals, Brett serves as the Chairman for an annual golf & dinner fundraiser event for SEAL Future Foundation, a nonprofit that equips retiring Navy SEALs with the tools and resources to get healthy and successfully transition to the next phase of their lives. Among Brett’s other passions are an afternoon on the golf course, surfing, playing chess, reading, and exploring new places with his wife, Sheena, and their fur baby, Yoshi the Shiba Inu.
