Athletes to Entrepreneurs: The Alumni Journey

Former Educator and Div. I Head Basketball Coach To Founder of Stay Shaded | Vonn Webb


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In this episode of Athletes to Entrepreneurs, Rob Finkelstein sits down with Vonn Webb—a former Division I head basketball coach, high school principal, and educator who has taken his life experience and turned it into a powerful mission.


Vonn shares his emotional and purpose-driven journey that led him to found StayShaded.org, a nonprofit focused on educating youth, parents, and athletes about the deadly dangers of fentanyl.Vonn opens up about the tragic loss of his son to fentanyl poisoning and how that life-altering moment became the fuel for his passion to make a difference. From coaching and mentoring athletes to building a platform for awareness, Vonn is an example of what it means to turn pain into purpose.Rob and Vonn dive deep into the athlete transition process, the long-term impact of coaches, the value of alumni support, and the need for stronger communities to help athletes thrive after the game ends.This episode is filled with heartfelt wisdom, real talk, and a call to action that resonates far beyond the court.---Key Takeaways:

  • Transition Is a Journey: Many athletes struggle with identity after sports—early preparation is crucial.
  • Mentorship Changes Lives: Alumni and coaches can offer real support for today’s athletes.
  • Relationships Over Results: The best coaches build bonds that last long after the buzzer.
  • Mindset Fuels Success: Athletes’ mental strength translates to business, leadership, and life.
  • Tragedy Can Spark Purpose: Vonn’s story is proof that you can rise through the pain and help others.
  • Fentanyl Is a Real Threat: Awareness and education are key to saving lives—especially in athletic communities.
  • Entrepreneurship Is a Natural Fit: Athletes are wired to lead, build, and innovate.
  • Network Like Your Future Depends On It: Because it often does.
  • Community Is Everything: Surrounding yourself with the right people can make all the difference.
  • Give Back to Move Forward: Vonn is living proof that impact multiplies when you serve others.
  • Instagram: [@coachdub1](  / coachdub1  )
  • Nonprofit IG: [@stayshadedorg](  / stayshadedorg  )
  • X (Twitter): [@webb_vonn](  / webb_vonn  )
  • Nonprofit X: [@orgstayshaded](  / orgstayshaded  )
  • Website: [www.stayshaded.org](https://www.stayshaded.org/)

---About Vonn Webb:Vonn Webb is a former educator, principal, and Division I head basketball coach who now leads StayShaded.org, a nonprofit organization dedicated to fentanyl awareness, education, and prevention. His journey from the court to the community is filled with leadership, heart, and a commitment to protecting the next generation.--- 🤝 Connect with Vonn Webb:---Connect with Alumni Direct:At Alumni Direct, we’re helping athletes like Vonn—and like you—navigate the transition from sport to life with the tools, connections, and support you need to thrive.📸 Instagram: [@AlumniDirect](  / alumnidirect  )💼 LinkedIn: [Alumni Direct](  / alumnidirect  )📘 Facebook: [Alumni Direct](  / alumnidirect  )You’re more than an athlete. And your next chapter could be your most impactful yet.#AthletesToEntrepreneurs #VonnWebb #StayShaded #FentanylAwareness #LifeAfterSports #AthleteEntrepreneurs #CoachForLife #MentorshipMatters #AthleteTransition #AlumniSupport #PurposeDrivenLeadership #YouAreMoreThanAnAthlete #AlumniDirect

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Athletes to Entrepreneurs: The Alumni JourneyBy Rob Finkelstein | Founder of Alumni Direct