Athletes to Entrepreneurs: The Alumni Journey

Rob Finkelstein | Founder of Alumni Direct

'Athletes to Entrepreneurs: The Alumni Journey' is a podcast where we speak with former college and professional athletes from all over the world as they share the joys, successes, failures and lessons on their entrepreneurial journey. Key topics include transitioning out of sports and teaching athletes that there is life after sports. Hosted by Rob Finkelstein of Alumni Direct, one of the top networks for alumni worldwide.

  1. Former Notre Dame and MLS Soccer player to Founder of Cool Factor Cryo - Jack Stewart

    Jun 17

    Former Notre Dame and MLS Soccer player to Founder of Cool Factor Cryo - Jack Stewart

    What happens when a professional soccer player decides to bring elite-level recovery to every athlete — not just the pros? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with Jack Stewart, retired MLS and USL soccer player turned entrepreneur and Founder of Cool Factor Cryo. Jack played at Notre Dame and went on to play professionally for clubs in Chicago, Dallas, Salt Lake City, Minnesota, and Fort Lauderdale. After his playing career, he worked in sports tech and HR sales before finding his entrepreneurial calling in athlete recovery. Jack built Cool Factor Cryo from the ground up — a mobile cryotherapy and recovery business that brings elite recovery tools directly to youth athletes, tournament teams, and sports communities. What started as one truck at an ECNL event has grown into a full franchise opportunity. This conversation covers the athlete-to-entrepreneur journey, the importance of building your network while you are still playing, and why recovery is the missing piece for the next generation of athletes. This conversation is a reminder that life after sports is not the end of the journey. It is a new chapter filled with lessons, growth, connection, and opportunity. ### In This Episode, We Discuss: - How youth and college sports shaped Jack's character and cultural awareness - Why Notre Dame's alumni soccer network became a model for athlete connection - The challenge of keeping your head in the game while planning for life after sports - Jack's "Goldilocks" journey through sports tech, HR, and sales before finding entrepreneurship - How Cool Factor Cryo started at an ECNL tournament and became a franchise opportunity - Why recovery habits formed early can extend an athlete's career and performance - How franchising Cool Factor Cryo is now open and why athletes are ideal candidates Key Takeaways ✨ Start networking before you think you need to.** Jack played across five professional teams. The athletes who thrived after sports were the ones who built relationships while still in the game — not after. ✨ Always be curious and always ask why.** The transition from athlete to professional is a mindset shift. Athletes are trained to execute. Business rewards those who ask questions and keep learning. ✨ Recovery is the gateway to long-term performance.** Tom Brady. Cristiano Ronaldo. LeBron James. They all invest heavily in their body. Cool Factor Cryo is bringing that same access to youth athletes and families. About Jack Stewart Jack Stewart is a retired professional soccer player turned entrepreneur and the Founder of Cool Factor Cryo. He played college soccer at Notre Dame and went on to have a professional career in the MLS and USL. After retiring, Jack worked in sports tech and HR before launching Cool Factor Cryo — a mobile recovery business bringing elite-level cryotherapy and wellness directly to athletes of all ages and levels. Connect with Jack Stewart - Website: coolfactorcryo.com - Instagram: https://www.instagram.com/stories/coolfactorcryo/ - LinkedIn: https://www.linkedin.com/search/results/all/?keywords=Cool%20Factor%20Cryo - Franchising inquiries: jack@coolfactorcryo.com Listen & Subscribe Listen to Athletes to Entrepreneurs: The Alumni Journey on YouTube, Spotify, Apple Podcasts, and all major podcast platforms. Connect with Alumni Direct 🌐 Website: https://alumnidirect.com ▶️ YouTube: https://www.youtube.com/@alumnidirectllc.203 🎧 Spotify: https://open.spotify.com/show/70OS33fNGMmOQbEvCoTdvD

    34 min
  2. Former College and Pro Volleyball Player to Founder of Beyond the Game

    Jun 3

    Former College and Pro Volleyball Player to Founder of Beyond the Game

    What happens when an athlete’s drive stays the same — but the structure that once supported it disappears? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with former UC Davis volleyball player, professional beach volleyball athlete, athletic trainer, coach, and founder of Beyond the Game, Jill Muhe. Jill shares how sports shaped her from childhood, growing up as a “gym rat” with a coach for a dad, playing basketball and volleyball, and eventually choosing volleyball as her main path. She reflects on her collegiate career at UC Davis, her transition into professional beach volleyball, and the lessons she learned from competing at a high level. Key Topics Discussed - Growing up around sports and becoming a lifelong athlete - Jill’s journey from UC Davis volleyball to professional beach volleyball - The emotional reality of transitioning out of sport - Why athletes often struggle after losing the structure of sport - How networking can feel more natural when approached with curiosity - The importance of building relationships before the game ends - Why alumni engagement can help athletes prepare for life after sports - The connection between athlete identity, purpose, and career direction - Jill’s transition from athletic training to coaching to entrepreneurship - The inspiration behind Beyond the Game - Helping athletes navigate job searches, interviews, and career growth - Why athletes need support systems, not just motivation Key Takeaways Your Drive Is Not the Problem Jill explains that many athletes struggle after sports not because they lack motivation, but because the support structure they had in athletics is no longer there. In sport, athletes have coaches, schedules, recovery, accountability, trainers, seasons, and teammates. After sport, that structure disappears — but the drive remains. Networking Starts with Curiosity Jill encourages athletes to approach networking by asking questions and learning about other people’s journeys, instead of only reaching out when they need a job. A simple conversation like, “What you do looks cool. Can you tell me more about your journey?” can open doors and build real relationships. Transition Is More Than Getting a Job Rob and Jill discuss how many athletes focus only on landing the next role after sports. But the deeper challenge is learning how to thrive in a new environment, rebuild support, avoid burnout, and create a life that still feels meaningful. Sport Gives Athletes More Than Competition Jill shares that athletes need to understand what sport gave them on an intrinsic level — whether that is purpose, challenge, connection, growth, structure, or joy. Once athletes understand what they are really missing, they can begin to find those same motivators in other areas of life. About Jill Muhe Jill Muhe is a former UC Davis volleyball player, professional beach volleyball athlete, certified athletic trainer, college volleyball coach, and founder of Beyond the Game. Connect with Jill Muhe Website: https://jillmuhe.comLinkedIn: https://www.linkedin.com/in/jillmuhe/ Instagram: https://www.instagram.com/beyondthegame.co/ Connect with Alumni Direct Website: https://alumnidirect.com ▶️ YouTube: https://www.youtube.com/@alumnidirectllc.203 🎧 Spotify: https://open.spotify.com/show/70OS33fNGMmOQbEvCoTdvD Memorable Quotes > “Hang in there, you will figure it out, and don’t be afraid to ask for help.” > “It will not go the way you think it will. But it will go.” > “Your drive is not the problem.” > “Nothing will ever feel the same way as when you were playing your sport at the highest level you could play it at.” > “We have to understand what sport gave us.” > “Networking is really how most people are landing their first job, their second job, their third job, their job after a layoff, their transition point, their pivot point.”

    40 min
  3. From College Basketball Player to Entrepreneur and Founder of Sports Mentorship | Drew Knuppel

    Jun 2

    From College Basketball Player to Entrepreneur and Founder of Sports Mentorship | Drew Knuppel

    What does it look like to finish your last college game and immediately start building a company? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with Drew Knuppel, a recent University of Tampa graduate, former NCAA Division II basketball player, and founder and CEO of Sports Mentorship LLC. Drew didn't wait around after sports ended. He took everything he learned on the court — the discipline, the communication, the ability to connect with people — and channeled it into building something for the next generation of student-athletes. Sports Mentorship matches current student-athletes with college athletes and recent grads who've been through the same transition, all virtually and nationwide. In this conversation, Drew is honest about what the transition has actually felt like — three months out, still adjusting, still figuring it out — while also sharing how staying active, staying connected, and leaning into entrepreneurship has kept him moving. He gives a real, balanced take on NIL, talks about the gap in athlete transition education, and explains why networking is the one skill every young athlete needs to develop before they ever leave their sport. This conversation is a reminder that life after sports is not the end of the journey. It is a new chapter filled with lessons, growth, connection, and opportunity. Drew's journey from youth sports to NCAA Division II basketball at the University of TampaThe gap in transition education for student-athletes — and what schools need to do differentlyHow to network without feeling intimidated, especially as a young athleteNIL: the benefits, the pay-for-play problems, and what the loyalty cost looks likeThe athlete skills that translate directly to entrepreneurshipSports Mentorship LLC — how it works, who it's for, and how to claim a free 30-day trial✨ Don't let your mind take away a great opportunity Networking feels awkward — especially when approaching coaches or people at a higher level. Drew's advice: get out of your own head, come prepared, and bring something of value to the conversation. ✨ Athlete skills are entrepreneur skills Organization, punctuality, communication, and the ability to relate to people — these are things athletes build over years of competition. Drew says those intangible skills have been the real foundation of running his company. ✨ There is a real gap in athlete transition support Most schools offer a one-day workshop and call it done. Drew lived it, and it became the reason he built Sports Mentorship — a platform providing real, ongoing mentorship for student-athletes. Drew Knuppel is a recent graduate of the University of Tampa, where he played NCAA Division II Basketball and earned his Sports Management degree. He is the founder and CEO of Sports Mentorship LLC, a company built around helping student-athletes understand that life is about far more than just their sport. Through virtual, nationwide mentorship sessions, Sports Mentorship connects student-athletes with current college athletes and recent graduates who can guide them through the journey ahead. Website: https://sportsmentorship.com/🎁 Free 30-Day Group Mentorship Trial: https://sportsmentorship.com/start/promo/free-30-group-founders/Instagram: @sportsmentorshipFacebook: sportsmentorshipTwitter/X: @sportmentorshipLinkedIn: sportsmentorshipListen to Athletes to Entrepreneurs: The Alumni Journey on YouTube, Spotify, Apple Podcasts, and other major podcast platforms. In This Episode, We Discuss:Key TakeawaysAbout Drew KnuppelConnect with Drew KnuppelListen & Subscribe

    31 min
  4. Former College and NBA Basketball Player to Founder of The Sole Survivors. Gary Forbes.

    May 28

    Former College and NBA Basketball Player to Founder of The Sole Survivors. Gary Forbes.

    What happens when a lifelong basketball dream evolves into a mission to impact millions of lives? In this episode of Athletes to Entrepreneurs: The Alumni Journey , Rob Finkelstein sits down with former college and NBA basketball player Gary Forbes to discuss his remarkable journey from the courts of Brooklyn to the NBA, and ultimately to becoming the founder of The Sole Survivors. Gary shares how his love for basketball began at an early age, the lessons he learned playing at the University of Virginia and UMass, and the perseverance required to reach the highest level of professional basketball. He opens up about competing with Type 1 diabetes, overcoming multiple knee surgeries, and navigating the difficult transition when his playing career came to an end. Today, Gary has turned his experiences into purpose through The Sole Survivors , a nonprofit and multimedia platform dedicated to empowering children living with chronic health conditions. Through superhero storytelling, education, and community, Gary is helping young people see their challenges not as limitations, but as superpowers. This conversation explores resilience, entrepreneurship, networking, athlete identity, health advocacy, and the importance of creating opportunities for the next generation. Key Topics Discussed - Growing up in Brooklyn and falling in love with basketball - Chasing the dream of playing in the NBA - Lessons learned from college athletics at Virginia and UMass - Why networking and relationships matter long after sports - The athlete mindset and entrepreneurial success - Transitioning out of professional basketball - Playing professionally while managing Type 1 diabetes - Overcoming adversity, injuries, and setbacks - The inspiration behind The Sole Survivors - Empowering children through storytelling and representation - Building a purpose-driven brand with global impact - Advice for athletes preparing for life after sport Key Takeaways Success Starts with Belief Gary shares the mindset that carried him from a childhood dream to the NBA: “If you think you can, you're right. If you think you can't, you're also right.” Athletes Are Built for Business The discipline, accountability, teamwork, resilience, and work ethic developed through sports create a strong foundation for entrepreneurship and leadership. Your Network Matters Building authentic relationships throughout your career can create opportunities, mentorship, and support long after your playing days are over. Turn Challenges into Purpose Gary's journey with Type 1 diabetes inspired him to create a platform that helps children see themselves as heroes rather than defined by their diagnoses. About Gary Forbes Gary Forbes is a former NBA player, entrepreneur, health advocate, and founder of The Sole Survivors , a children's multimedia platform empowering kids with chronic health conditions through storytelling, education, and optimism. As one of the few professional athletes to play basketball while living with diabetes, Gary uses his journey to inspire resilience, wellness, and purpose around the world. His mission is to help children transform adversity into their superpower through media, community, innovation, and advocacy. Connect with Gary Forbes 🌐 Website: [https://thesolesurvivors.com](https://thesolesurvivors.com/) 📸 Instagram: https://www.instagram.com/garyforbes_ 💼 LinkedIn: http://linkedin.com/in/gary-forbes-082b5b267 Connect with Alumni Direct 🌐 Website: [https://alumnidirect.com](https://alumnidirect.com/) ▶️ YouTube: https://www.youtube.com/@alumnidirectllc.203 🎧 Spotify: https://open.spotify.com/show/70OS33fNGMmOQbEvCoTdvD Memorable Quotes “Your network is a big part of your net worth.” “Your present situation is not your final destination. “The game is never over. Sometimes you run out of time, but the game is never over.” “We're creating superheroes for every childhood health challenge in the world.”

    29 min
  5. Former College Basketball Player & Founder of Move More Collective | Mike Cavallaro

    May 12

    Former College Basketball Player & Founder of Move More Collective | Mike Cavallaro

    Mike Cavallaro’s journey is a powerful reminder that life after sports is about rediscovering purpose beyond the game. After a career-ending back injury cut short his college basketball career, Mike faced the identity loss and uncertainty many athletes experience during transition. He climbed the corporate ladder searching for fulfillment through money, status, and titles—but ultimately realized something was missing. That journey led him to found **Move More Collective**, a wellness-driven movement focused on helping people improve their physical, mental, and social well-being through healthier lifestyle experiences. This episode dives into athlete identity, mentorship, networking, entrepreneurship, and redefining what wellness and success truly look like after sports. --- Key Topics Covered - Growing up in a sports-driven family - Playing college basketball at Macalester College - Career-ending injury and identity loss - Navigating life after sports - The importance of networking and mentorship - Entrepreneurship and athlete leadership - Building Move More Collective - Redefining nightlife and wellness culture - Mental, physical, and social wellness balance --- Key Takeaways - Athletes are more than their sport - Staying coachable creates long-term growth - Networking starts while you’re still playing - Transition out of sports is deeply emotional - Discipline from sports translates into business - Mentorship can help athletes through uncertainty - True wellness includes physical, mental, and social health --- Powerful Advice from Mike 👉 *“You don't know everything. Keep your head down. Stay coachable.”* 👉 *“Seek out mentors.”* 👉 *“The ball stops bouncing for everyone at some point.”* --- About the Guest – Mike Cavallaro Mike Cavallaro is a former college basketball player and the Founder of Move More Collective, a wellness-focused brand helping redefine social wellness and nightlife culture. After climbing the corporate ladder and finding himself unfulfilled by traditional success, Mike created Move More Collective to push forward a more holistic wellness movement—using physical wellness as a tool to support mental and social well-being around the clock. --- Connect with Mike Cavallaro 🌐 Website: [https://www.movemorecollective.com](https://www.movemorecollective.com/) 📱 Instagram: https://www.instagram.com/movemorecollective 📱 Instagram: https://www.instagram.com/foundingmover 📱 Personal Instagram: https://www.instagram.com/mmcavallaro 💼 LinkedIn: https://www.linkedin.com/in/mike-cavallaro/ --- *Connect with Alumni Direct 🌐 Website: [https://alumnidirect.com](https://alumnidirect.com/) 🎧 Spotify: https://open.spotify.com/show/70OS33fNGMmOQbEvCoTdvD 📺 YouTube: https://www.youtube.com/@alumnidirectllc.203

    34 min
  6. Former College Football and Basketball Player to Founder of Marc Winston Enterprises

    May 6

    Former College Football and Basketball Player to Founder of Marc Winston Enterprises

    Marc Winston’s journey is a powerful example of what life after sports can look like. From playing both football and basketball at the collegiate level to building a career in corporate America—and now leading his own consulting business—Marc shares how discipline, resilience, and mindset shaped his path beyond the game. This episode dives into transition, identity, and how athletes can use what they’ve built to succeed in business and life. 👉 “Embrace the journey—failures and all.” 👉 “Be bold. Go for everything as if you deserve it.” Marc Winston is a former Division 1 athlete turned enterprise leader with over 15 years of experience in global supply chain, procurement, and contract strategy. He has led large-scale operations across Fortune 1 and national organizations. Today, as Founder and CEO of Marc Winston Enterprises, he helps businesses and athletes turn strategy into scalable growth and long-term success. 🌐 Linktree: ⁠https://linktr.ee/marcwinstonenterprises⁠ 📩 Email: ⁠mwinstonenterprises@yahoo.com⁠ 💼 LinkedIn: Marc Winston 📱 Instagram: @_ .winston (underscore dot winston) 🌐 Website: ⁠https://alumnidirect.com⁠ 🎧 Spotify: ⁠https://open.spotify.com/show/70OS33fNGMmOQbEvCoTdvD⁠ 📺 YouTube: ⁠https://www.youtube.com/@alumnidirectllc.203⁠ Key Topics Covered Key Takeaways Powerful Advice from Marc About the Guest – Marc Winston Connect with Marc Winston Connect with Alumni Direct

    33 min
  7. Former Gonzaga Competitive Dancer as Founder and Partner of 8Nine Agency

    Apr 29

    Former Gonzaga Competitive Dancer as Founder and Partner of 8Nine Agency

    What happens when your identity as an athlete ends—and no one prepared you for what comes next? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob sits down with Nicole Bradley — Founder & Partner of 8Nine Agency — to talk about identity, financial literacy, and building a life beyond sports. Nicole shares her journey from Gonzaga competitive dancer to working 20 years in professional sports—and why so many athletes struggle not just emotionally, but financially, after the game ends. This is a powerful conversation for athletes navigating transition, NIL opportunities, and finding purpose beyond sport. Key Takeaways - The transition out of sport is both emotional and financial - Why athletes often feel an identity crisis after the game ends - The gap in financial literacy for athletes and families - Why networking early creates long-term opportunities - How athletes are naturally wired for entrepreneurship - The importance of involving the family in financial education - Why passion makes the transition easier - How NIL is changing the game—but also creating new risks Nicole’s Advice to Athletes 👉 “Stay the course.” 👉 “Take the chance.” 👉 “Find what you’re passionate about — and go all in.” About the Guest Nicole Bradley is the Founder & Partner of 8Nine Agency, where she helps athletes transition from sport into entrepreneurship and financial independence. With over 20 years of experience in professional sports, she now focuses on financial literacy, NIL education, and helping athletes and their families build and protect long-term wealth. About 8Nine Agency 8Nine Agency works with athletes at every stage—from NIL to professional careers—helping them build: - Financial literacy - Long-term wealth strategies - Career pathways beyond sport - A strong financial “team” or roster Focused on guiding athletes from financial literacy to legacy. Connect with Nicole - Instagram: https://www.instagram.com/coachnicolebradley - LinkedIn: https://www.linkedin.com/in/nicolebradley 🎧 Listen & Connect with Alumni Direct 🌐 Website: [https://alumnidirect.com](https://alumnidirect.com/) 📺 YouTube: @alumnidirectllc.203 🎧 Available on Spotify, Apple Podcasts & all major platforms Final Thought Your career in sports may end— but your potential doesn’t. The sooner you build direction, purpose, and financial awareness— the stronger your next chapter will be. Find what you’re passionate about and go all in.”

    33 min
5
out of 5
4 Ratings

About

'Athletes to Entrepreneurs: The Alumni Journey' is a podcast where we speak with former college and professional athletes from all over the world as they share the joys, successes, failures and lessons on their entrepreneurial journey. Key topics include transitioning out of sports and teaching athletes that there is life after sports. Hosted by Rob Finkelstein of Alumni Direct, one of the top networks for alumni worldwide.