Annie Bailey is a former Division I lacrosse player at the University of Colorado, a boarding school graduate from Culver Academies, and now a CEO and Equity Partner at Rise Sports Advisory — a firm built to help elite athletes build generational wealth, not just a paycheck.
In this episode, Annie breaks down exactly why 75 percent of NFL players end up broke or divorced within five years of retiring, what the average two-year NFL career actually means for long-term financial planning, and why the identity crisis that hits athletes when the sport ends is just as dangerous as the financial one. She also pulls back the curtain on how Rise works with NIL athletes in college all the way through retirement — using a slow, steady approach to financial education that builds real discipline before the big checks ever arrive.
We also get into the mental health side of this, including why Annie believes asking for help is still one of the hardest things for athletes to do, why trust and someone who makes you feel good are two completely different things, and why the most important word she chose to lead by in 2026 is nurture.
If you are a young athlete, a parent of an athlete, or anyone trying to understand what financial success actually looks like after sports, this conversation is for you.
Rise Sports Advisory: risesportsadvisory.com
Follow Annie on Instagram: @anniemorschesbailey
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