In this episode of Dealmaker$, Shane sits down with Jason Garey — a Mac Hermann Trophy winner (soccer’s Heisman), National Champion at Maryland, MLS Cup Champion with the Columbus Crew, and now one of the most trusted financial planners working with athletes, entrepreneurs, and business owners across the country.

Jason’s story begins in rural South Louisiana, growing up on ten acres, fishing ponds, pecan trees, and a house full of siblings — two adopted, one elite soccer prospect. His parents, both school teachers, started the town’s youth soccer league from scratch because none existed.

He describes traveling the South in search of competition, writing letters to English clubs, and at age 15 living with his grandmother’s elderly friends in Liverpool for a month and a half — attending school, drinking his first pub beer, and dislocating his shoulder for five brutal hours in the ER.

After choosing Maryland over a full ride at Cleveland State, he went from anonymous walk-on to:

• Maryland’s all-time leading scorer

• Four-time Final Four participant

• 2005 National Champion

• 2005 Hermann Trophy winner

He details playing alongside future pros, earning his spot through injuries to others, and the legendary bus confrontation that reset the team’s mindset and launched them into a title run.

Jason then dives into the reality of MLS:

• Being the #3 overall draft pick

• Making $40,000 a year

• Winning an MLS Cup

• Multiple surgeries (two shoulders + major hip)

• The grind, the travel, the roster risk, the mental battles

• The day he knew he wanted life after soccer

He then walks through the second act of his life — the one that required far more courage: Becoming a Financial Planner

• Doing an unpaid internship with his now-partner

• Learning the business from scratch

• Staying up nights studying for the CFP exam

• Building clients slowly

• Battling impostor syndrome when advising people wealthier than him

• Developing a niche serving athletes, retirees, and business owners

His firm now manages hundreds of families and specializes in:

• Athlete financial literacy

• Retirement income sequencing (“the hard part”)

• Business owner exits and liquidity events

• Tax-efficient planning

He shares why the biggest mistakes people make are:

• Not hiring professionals

• Overspending

• Lacking a financial infrastructure

• Not understanding taxes

• Misjudging risk

The episode ends with incredible reflections on confidence, fatherhood, money psychology, purpose, and the freedom of telling a client: “You can retire today. You’re done. Go live your life.”

It’s one of the most inspiring, vulnerable, and practical Dealmaker$ episodes yet.

This is Dealmaker$ — where real deals meet real strategy.