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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Six years grinding overseas. Multiple country jumps. Undrafted in 2006. Chris Copeland could have walked away from basketball more times than he can count, but instead he became Belgian league MVP, signed with the New York Knicks in 2012, and earned the nickname The X-Factor over 171 plus NBA games with the Knicks, Pacers, and Bucks.

In this episode of Intangible Podcast, Chris sits down with former NFL center and host Chris Spencer to break down the mindset that took him from undrafted free agent to the NBA stage at Madison Square Garden. They get into the psychology degree that taught him people matter more than basketball, the mom who installed a no excuse mentality before he even knew what one was, and the night he proved to himself, not the world, that he belonged.

Chris also opens up about where real confidence comes from, what most people get wrong about perseverance, why he is grateful for every setback he calls divine timing, and the wisdom he wants to pass on to the next generation of athletes who think success means never losing.

If you are an athlete chasing a dream that feels far away, a parent raising a competitor, or anyone trying to build the mental resilience it takes to compete at a high level, this conversation is for you.

Subscribe to Intangible Podcast for more conversations with elite athletes and coaches about the traits that actually got them to the top, the ones nobody sees on the stat sheet.

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What does it actually take to build generational wealth as a professional athlete? In this episode of the Intangible Podcast, Chris Spencer sits down with Michael Ledo, CEO and founder of Rise Family Office, for the unfiltered conversation most athletes never get to have until it is already too late.

Michael is the nephew of Eugene Parker, the first major Black sports agent in America. He is a two-time Division II All-American running back whose ankle injury became the turning point that led him to build three athletic training facilities, develop over 100 Division I athletes and 15 NFL players, and eventually create one of the most distinctive wealth management platforms for professional athletes in the country.

In this conversation, Michael and Chris break down why a shockingly small percentage of athletes are prepared for life after the game, what it really means to learn the language of money, and the dangerous difference between a financial advisor who preserves your wealth and a family office that grows it. Michael shares real client success stories from Jalen Smith and Jesse Bates and reveals the mindset shifts that separated them from the 78 percent of athletes who go broke within five years of leaving the game, even while 56 percent of those same athletes had financial advisors the entire time.

This episode gets personal. Chris opens up about his own struggle with dyslexia and what it felt like to hide behind the helmet for years. Michael explains why most athletes are hiding too, why the helmet has to come off before real wealth can be built, and how vulnerability is the first step toward operating like a true entrepreneur. From the Five Whys method for finding your real motivation to the off-season calendar that Rise Family Office builds for every client, this is a masterclass in the intangibles of financial performance.

👉 Follow the Intangible Podcast for more stories of grit, resilience, and peak performance:

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