Willie Cauley-Stein's Entrepreneurship, Community, and NCAA Reform Needs

KSR · December 30, 2025 · Listen to Original Episode →

Original Title:

TL;DR

Willie Cauley-Stein's transition to training and business ventures, like his golf apparel brand, demonstrates a post-athletic career path focused on community building and entrepreneurship in Lexington.
The discussion highlights the NCAA's struggle to regulate the transfer portal and NIL, creating chaos and potentially disadvantaging high school recruits and long-term player development.
Willie's personal experience with financial mismanagement after his NBA career underscores the critical need for comprehensive financial literacy education for student-athletes.
The podcast touches on the evolving landscape of college sports, where athletes are increasingly viewed as professional student-athletes, necessitating a reevaluation of NCAA rules and support systems.
Willie's commitment to sponsoring local youth, exemplified by providing shoes and a coat to a young athlete, showcases a dedication to giving back and fostering community engagement.

Deep Dive

Willie Cauley-Stein, former UK standout and NBA player, joined Kentucky Sports Radio to discuss his post-basketball career aspirations, family life, and community engagement. Cauley-Stein is actively developing a golf brand, "Lit Tour," which blends his passion for golf, fashion, and community building, aiming to establish a strong presence within Kentucky before expanding. He also shared his experience coaching and mentoring young athletes through his "Brick House Skills Academy," highlighting the personal fulfillment derived from witnessing their improvement and the tangible impact of providing essential resources like shoes and clothing to underprivileged children.

Cauley-Stein detailed his plans to establish a training facility in Lexington, collaborating with former players and coaches to foster the next generation of athletes. He expressed a desire for his own children to attend school in Lexington, reinforcing his commitment to the community. His current ventures include expanding the distribution of his golf apparel line, "Lit Tour," through various retail partners and online platforms, with a focus on organic growth and community engagement. He also shared a heartwarming story of sponsoring a young athlete, David, providing him with new basketball shoes and winter clothing, an act that deeply moved the recipient and underscored Cauley-Stein's dedication to giving back.

The conversation also touched upon the evolving landscape of college athletics, particularly the NCAA's challenges with the transfer portal and name, image, and likeness (NIL) regulations. Cauley-Stein offered a player's perspective, acknowledging the current "chaos" and the need for clearer rules, while also emphasizing the importance of financial literacy and long-term planning for athletes who may not reach professional careers. He advocated for comprehensive financial education within collegiate programs to equip student-athletes with the skills to manage their earnings and build sustainable futures, drawing from his own experiences with financial mismanagement after his NBA career.

Action Items

Audit personal financial literacy: Identify 3-5 knowledge gaps in budgeting, investing, and tax management.
Develop a financial literacy curriculum: Outline 5 core modules for athletes, covering budgeting, investment basics, and tax implications.
Track personal spending habits: Monitor expenses for 2-4 weeks to identify areas for potential savings.
Create a personal investment plan: Define 3-5 investment goals and corresponding strategies.
Establish a bill payment system: Implement a process for timely payment of all personal bills.

Key Quotes

"I feel like my man's about to be on tour at the rate it seems he's playing these days uh, you know these days uh I like to say I'm on the lit tour. Yeah, the lit tour. The lit tour. Yeah, two tees, two tees."

Willie Cauley-Stein describes his current passion for golf as being on the "lit tour," indicating a dedicated and enjoyable pursuit of the sport. This phrasing suggests a playful yet serious commitment to his golf game, highlighting it as a significant focus in his life.

"Yeah, I mean, fall goes well this year. Um, one of my daughters uh gets to start kindergarten this year, her first year of kindergarten. So, um, we wanted to move back here and then uh, I just didn't want to move her in the middle of the year."

Willie Cauley-Stein explains his desire to relocate back to Lexington, emphasizing family priorities, specifically his daughter's first year of kindergarten. This decision reflects a commitment to stability for his children and a preference for establishing roots in a familiar community.

"And bro, it was the most like gratifying thing watching like a kid get better in 20 minutes. Like couldn't hold a ball and then after 25 minutes, he's hitting like three in a row. I was like, oh bro, I'll sit here for an hour and a half and watch you shoot the same shot until you can hit five in a row."

Willie Cauley-Stein expresses the profound satisfaction he derives from his training program, particularly witnessing tangible progress in young athletes. The detailed example of a child improving their shooting ability illustrates the rewarding nature of his coaching, highlighting his dedication to fostering skill development.

"Yeah, I don't know if you guys remember, um, he was a manager of ours, Michael Stump, um, when I was here. Um, was also the one, my, my roommate at the lodge. But he's, he's one of my partners in it."

Willie Cauley-Stein discusses his business partnership with Michael Stump, a former manager and roommate from his college days. This quote establishes a connection to his past and highlights the collaborative nature of his current ventures, indicating a network of long-standing relationships.

"It's so tricky when you have kids, like you don't necessarily want to coach or train your kids, right? But like, I don't know, I guess I'm in a little different spot where I wouldn't probably wouldn't anybody else to train them, but I don't know, there's just, it just depends on how they take it, you know?"

Willie Cauley-Stein reflects on the complexities of coaching his own children, acknowledging the potential challenges while expressing a unique perspective on his own family. He suggests that while it can be difficult, he might be an exception, emphasizing that the child's receptiveness is a key factor.

"It's like, I don't know what if you ever felt yourself in a moment of, here's a perfect example, you ever been driving around and you drove seven miles and you were like, how did I just drive seven miles? You're in the motion zone, like your body's just doing it."

Willie Cauley-Stein explains the concept of the "motion zone" by using the relatable experience of driving without conscious recollection. This analogy helps to illustrate a state of automatic, fluid action, which he connects to both athletic performance and everyday activities.

Resources

External Resources

Books

"The Lit Tour" by Willie Cauley-Stein - Mentioned as a personal golf brand.

Articles & Papers

"The Lit Tour" (Personal Golf Brand) - Discussed as a personal golf brand.

People

Willie Cauley-Stein - Guest on the show, discussing his personal golf brand, family, and future plans.
D Mills - Mentioned as someone Willie Cauley-Stein plans to work with for a training program.
Michael Stump - Former manager and partner in Willie Cauley-Stein's training academy.
Darius - Mentioned in relation to discussing the alumni center.
Rammell Bradley - Mentioned as a celebrity sighting at Tolly Ho.
Devin Booker - Mentioned in relation to a story about someone licking his car.
Steph - Mentioned as someone Willie Cauley-Stein watched play golf.
Betty - Mentioned as a friend's mom and a phenomenal golfer/teacher who got Willie Cauley-Stein into golf.
Josh Teeter - Mentioned as a PGA Tour golfer texting in about setting up foursomes.
Wookash - Mentioned as a special guest who might join the show.
Matt - Mentioned as being off for the holidays.
Shannon - Mentioned as being off for the holidays.
Billy - Mentioned as being off for the holidays.
Mario - Mentioned as being off for the holidays.
John Calipari - Discussed in relation to the transfer portal and NCAA rules.
Jeff Goodman - Mentioned as having received a statement from the NCAA.
Trenton Flowers - Mentioned as an NBA player considering returning to college.
Cuba - Mentioned as a friend of Willie Cauley-Stein who coaches at a junior high.
Dave - A young man sponsored by Willie Cauley-Stein for his skills academy.
Cal - Mentioned in relation to John Calipari's comments on the transfer portal.
Chad Baker-Mizra - Mentioned in relation to financial literacy.
Alicia - Mentioned as having a cooking video and recipes for managing MG symptoms.

Organizations & Institutions

Kentucky Sports Radio (KSR) - The name of the radio show.
KS Bar and Grill - Location where the radio show is broadcasting from.
T J Smith Law Office - Sponsor of Kentucky Sports Radio.
Clark's Pump Shop - Sponsor of Kentucky Sports Radio.
A Vision Glass Tech Machine - Mentioned in relation to a phone number.
Comedy Up Broadway - Venue hosting New Year's Eve events and other shows.
Netflix - Mentioned in relation to a comedian.
AGT (America's Got Talent) - Mentioned in relation to a finalist.
Commonwealth Cares - Sponsor of a segment, promoting local charities and raffles.
Tolly Ho - A restaurant in Lexington that is closing.
UK (University of Kentucky) - Mentioned in relation to students, basketball players, and alumni.
Granger - Company mentioned for auto-reordering and supplies.
Cosentyx - Medication discussed for hidradenitis suppurativa (HS).
Odoo - Business software platform.
National Football League (NFL) - Mentioned in relation to sports analytics.
Pro Football Focus (PFF) - Mentioned as a data source for player grading.
New England Patriots - Mentioned as an example team for performance analysis.
HBCU (Historically Black Colleges and Universities) - Mentioned in relation to school pride and atmosphere.
Uber Eats - Delivery service mentioned.
NCAA - Mentioned in relation to transfer rules and player eligibility.
NBA - Mentioned in relation to players and financial matters.
Kentucky Branded - Retailer selling Willie Cauley-Stein's hats.
Golf Headquarters - Retailer selling Willie Cauley-Stein's hats.
Golf Exchange - Retailer selling Willie Cauley-Stein's hats.
Sanacon - Event where Willie Cauley-Stein handed out hats.
Dick's Sporting Goods - Store where Willie Cauley-Stein bought shoes and a coat for a sponsored child.
Nike - Brand of a puffer jacket.
Harden's - Brand of shoes.
Mortar Golf - Website where Willie Cauley-Stein's products will be available.
CVS - Pharmacy and community store.
Audible - Audiobook platform.
iHeartRadio - Podcast and radio platform.
MG United - Website with recipes and tips for managing MG symptoms.

Tools & Software

Odoo - All-in-one business software platform.

Websites & Online Resources

cosentyx.com - Website for information on Cosentyx.
odoo.com - Website for the Odoo business software.
commonwealthcauses.org - Website for Commonwealth Cares events.
kentuckybranded.com - Website for Kentucky Branded, selling Willie Cauley-Stein's hats.
mgunited.com - Website with recipes and tips for managing MG symptoms.
audible.com - Website for audiobooks.
iheart.com - Website for iHeartRadio.
cvs.com - Website for CVS.

Other Resources

Hidradenitis Suppurativa (HS) - A medical condition discussed in relation to Cosentyx.
Transfer Portal - Discussed in relation to college sports player movement.
NIL (Name, Image, and Likeness) - Discussed in relation to college athlete compensation.
Financial Literacy - Discussed as a crucial skill for athletes.
Queen of Hearts - Raffle mentioned by Commonwealth Cares.
Bourbon Collection Raffle - Raffle mentioned by Commonwealth Cares.
Quiz Night - Event at KS Bar and Grill.
The Lit Tour - Willie Cauley-Stein's personal golf brand.
Brick House Skills Academy - Willie Cauley-Stein's skills academy.
The Motion Zone - A concept related to focus and performance, discussed in golf and free throws.