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. 14h ago

    From Stanford Soccer to Founder and CEO of Joey AI | Carly Malatskey

    What happens when you stop optimizing for title or prestige and start optimizing for what you can learn? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with Carly Malatskey, founder and CEO of Joey, an AI matchmaker rethinking how people meet. Before becoming a founder, Carly played for Stanford Women's Soccer, where she won two NCAA Division I national championships. She went on to work as a software engineer and venture investor at Floodgate before leaving venture to build Joey. Carly also hosts She Leads, a podcast featuring 150+ conversations with founders and leaders. Carly and Rob talk about her path from the soccer field to software engineering to venture capital, and what finally pushed her to start her own company. She shares how cold-emailing and creating her own opportunities shaped her career, why she chose to follow great people early on instead of chasing titles, and how the lessons she learned as an athlete still show up in how she builds teams today. 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. Carly's path from Stanford soccer to software engineering and venture capitalWhy she left venture capital to start JoeyCold-emailing and creating your own opportunitiesFollowing great people early in your careerOptimizing for learning over title or prestigeHow athlete skillsets translate into entrepreneurshipWhat she's building with Joey and where dating is headed✨ Create your own opportunities Carly didn't wait for the perfect opening. Cold-emailing and reaching out directly opened doors that a traditional path wouldn't have. ✨ Optimize for learning, not titles Early in her career, Carly chose roles based on who she'd work with and what she'd learn, not the title attached to the job. ✨ Athlete habits carry over to entrepreneurship The resilience and team-building instincts Carly built on the soccer field now shape how she leads at Joey. Carly Malatskey is the founder and CEO of Joey, an AI matchmaker rethinking how people meet. Before becoming a founder, Carly played for Stanford Women's Soccer, where she won two NCAA Division I national championships. She went on to work as a software engineer and venture investor at Floodgate before leaving venture to build Joey. Carly also hosts She Leads, a podcast featuring 150+ conversations with founders and leaders, and brings lessons from elite athletics into how she approaches resilience, team-building, and entrepreneurship. Instagram: https://www.instagram.com/carlymalatskey/LinkedIn: https://www.linkedin.com/in/carlymalatskey/TikTok: https://www.tiktok.com/@carlymalatskeyJoey Instagram: http://instagram.com/calljoeyai Listen to Athletes to Entrepreneurs: The Alumni Journey on YouTube, Spotify, Apple Podcasts, and other major podcast platforms.

    From Stanford Soccer to Founder and CEO of Joey AI | Carly Malatskey
  2. Jul 22

    Former College Soccer Player to Co-Founder and CEO of Bridged Platform | Natalia Bowles

    Your network is your net worth. Just ask a college athlete who built a company out of it. In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with Natalia Bowles, a former college soccer player, fitness entrepreneur, and founder of Bridge Platform. Natalia played soccer at Azusa Pacific University and Trevecca Nazarene University, where discipline and teamwork shaped who she is today. She talks about the gap in transition support for student-athletes, and why she built Bridge Platform to close it. Natalia also opens up about becoming a franchise owner of Stride Nashville and how community carried her from athlete to entrepreneur. 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: Growing up playing soccer and the discipline it builtThe missing education around life after sports in collegeWhy networking matters most while you're still an athleteNIL: the opportunities, the gaps, and what needs to improveThe transfer portal and balancing loyalty with opportunityBuilding Bridge Platform to connect student-athletes with employersKey Takeaways ✨ Your network is your net worth — connect with people now, not after you graduate. ✨ Prepare for life after sports early — have a backup plan. ✨ Athletes are built for entrepreneurship — the discipline transfers directly. About Natalia Bowles Natalia Bowles is a driven student-athlete, entrepreneur, and communications professional with a passion for helping others create opportunities beyond the game. She played college soccer at Azusa Pacific University and Trevecca Nazarene University, where she studied multimedia journalism. Natalia is the founder of Bridge Platform, a platform designed to connect student-athletes with project-based internships, networking opportunities, and career experiences that prepare them for life after sports. She is also the franchise owner of Stride Nashville. Connect with Natalia Bowles Website: bridgeplatform.comLinkedIn: https://www.linkedin.com/in/natalia-bowles-963591252/Instagram: https://www.instagram.com/natalia.bowles/?hl=enBridge Platform Instagram: instagram.com/bridgeplatform

    Former College Soccer Player to Co-Founder and CEO of Bridged Platform | Natalia Bowles
  3. Jul 8

    From College Baseball Player to Founder of Constant Sports Management | Conner Schenk

    What does it take to turn an athlete's instincts for competition and relationships into a business built on partnerships? In this episode of Athletes to Entrepreneurs: The Alumni Journey, Rob Finkelstein sits down with Conner Schenk, a former college baseball player and founder of Constant Sports Management. Conner built Constant Sports around sports business advisory, partnerships, and revenue growth. He works with athletes, brands, sports technology companies, and emerging businesses to help build strategic partnerships and unlock new opportunities across the sports industry. He also hosts the Constant Sports Podcast, focused on the future of sports business. In this conversation, Conner talks about how the skills he built as an athlete carried into entrepreneurship, why networking and relationship-building matter so much for athletes, the importance of alumni engagement, and what his own transition out of sports looked like. 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. How the athlete skillset translates into entrepreneurshipWhy networking and building relationships matters for athletesThe importance of alumni engagementConner's own transition out of sportsBuilding Constant Sports Management and the Constant Sports Podcast✨ Athlete skills carry over to business The discipline and relationship-building athletes learn in competition become the foundation for entrepreneurship. ✨ Networking is a skill you build, not a talent you're born with Conner points to connecting and building relationships as a core part of long-term success after sports. ✨ Alumni engagement keeps the door open Staying connected to your alumni network creates opportunities long after your playing days end. Conner Schenk is a former college baseball player and founder of Constant Sports, a company focused on sports business advisory, partnerships, and revenue growth. He works with athletes, brands, sports technology companies, and emerging businesses to help build strategic partnerships across the sports industry. He also hosts the Constant Sports Podcast. Instagram: @Constantsports1X (Twitter): @ConstantSports1YouTube: @Constant SportsLinkedIn: Constant SportsListen to Athletes to Entrepreneurs: The Alumni Journey on YouTube, Spotify, Apple Podcasts, and other major podcast platforms.

    From College Baseball Player to Founder of Constant Sports Management | Conner Schenk
  4. 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

    Former Notre Dame and MLS Soccer player to Founder of Cool Factor Cryo - Jack Stewart
  5. 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.”

    Former College and Pro Volleyball Player to Founder of Beyond the Game
  6. 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

    From College Basketball Player to Entrepreneur and Founder of Sports Mentorship | Drew Knuppel
  7. 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.”

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