Most athletes aren’t short on drive.

They’re short on guidance once the uniform comes off.

In this episode, Rob Finkelstein sits down with **John Damon—one of the most trusted performance coaches in the country—to talk about what *really* determines success after sports: **support, standards, and who’s in your corner when the game changes.

John has trained Hollywood talent, elite athletes, and Fortune 500 executives. But his edge isn’t just physical—it’s philosophical. A former **Boston College football scholarship athlete**, John understands the identity shift, the void, and the danger of trying to “figure it out alone.”

That’s why he built **The Cave**—a private training and recovery sanctuary in Charlotte, NC—designed not just to train bodies, but to **protect standards, culture, and mental health**.

About the Guest: John Damon

John Damon is a celebrity trainer, performance coach, and gym designer, widely respected for his intentional, high-standard approach to human performance.

His philosophy is simple—and uncompromising:

Every session is intentional.

Every moment is coached with purpose.

Every outcome reflects the standard.

Through his work with elite performers and executives, John has become a trusted voice for athletes navigating transition, entrepreneurs building discipline, and leaders who refuse to lower the bar.

🔗 Website: https://johndamon.com/

What You’ll Learn in This Episode

- Why **athletes don’t fail in transition—systems fail them**

- How **networking and alumni engagement** change post-sport outcomes

- Why **vulnerability is a strength**, not a liability

- How teamwork applies just as much in business as it does in the locker room

- What most athletes misunderstand about money, identity, and career longevity

- Why environment matters—and how **The Cave** was built to protect it

- The difference between chasing opportunity and **building standards that travel**

👉 **Join the private platform built exclusively for athletes, creators, and leaders:**

[**https://www.alumnidirect.com/**](https://www.alumnidirect.com/)

Because the transition is easier — and far more powerful — **when you don’t walk it alone.**

**Connect with Alumni Direct:**

- Website: https://www.alumnidirect.com/

- Instagram: @alumnidirect

- X (formerly Twitter): @alumnidirect

- Facebook: Alumni Direct

- LinkedIn: Alumni Direct

In this episode of Athletes to Entrepreneurs: The Alumni Journey, host Rob Finkelstein sits down with Ciaran Brayboy — former Harvard basketball player whose path to elite athletics didn’t begin with early stardom, but with late discovery, discipline, and an open mind.

Ciaran shares a refreshingly honest look at what it means to find your lane after the game, especially when your athletic journey starts later than most. From initially disliking sports to discovering basketball in eighth grade, to earning Division I opportunities and competing at Harvard University, Ciaran’s story is rooted in growth, curiosity, and perspective.This conversation goes beyond stats and highlights to explore the real transition moments athletes face — identity shifts, pressure to “have it all figured out,” and the often-overlooked power of relationships.

Rob and Ciaran dive deep into:

Why networking isn’t transactional, but relationalHow cross-sport and non-athlete connections open unexpected doorsThe role of alumni mentorship in shaping life after sportsWhy staying present matters more than chasing the next titleAt its core, this episode is about:curiosity over ego, relationships over resumes, and growth beyond the scoreboard.About Ciaran BrayboyCiaran Brayboy is a former Harvard basketball player whose athletic journey began later than most — and became stronger because of it.After discovering basketball in middle school and rapidly developing through discipline and work ethic, Ciaran earned Division I opportunities and ultimately competed at the Ivy League level. While at Harvard, he balanced elite athletics with academics, initially pursuing a medical path before realizing the long-term value of relationships, mentorship, and alumni connection.Today, Ciaran is passionate about helping athletes think beyond their sport, encouraging them to build authentic networks, seek diverse perspectives, and prepare intentionally for life after competition.At Alumni Direct, we believe the athlete journey doesn’t end at the final whistle — it evolves.If you’re navigating life after sports, exploring entrepreneurship, or looking for a community that understands the transition:👉 Join the private platform built exclusively for athletes, creators, and leaders:https://www.alumnidirect.com/Because the transition is easier — and far more powerful — when you don’t walk it alone.Connect with Alumni Direct:Website: https://www.alumnidirect.com/Instagram: @alumnidirectX (formerly Twitter): @alumnidirectFacebook: Alumni DirectLinkedIn: Alumni Direct

In this episode of Athletes to Entrepreneurs: The Alumni Journey, host Rob Finkelstein sits down with **Gerald Hearns** — former college football **walk-on turned scholarship athlete**, entrepreneur, and **Founder & CEO of Too Cool Alkaline Water.

Gerald shares a raw and real look at what happens when the game ends and life begins. From grinding his way onto scholarship, to building businesses, to leading as **President of Team America**, Gerald breaks down the mindset shift every athlete must make to win beyond sports.

This conversation dives deep into the realities of **identity, discipline, networking, and life after the scoreboard**, and why athletes who prepare early don’t just survive the transition — they thrive.

At its core, this episode is about:

**owning your identity, building relationships, and choosing discipline over regret.

*About Gerald Hearns

**Gerald Hearns** is a former college football player who went from **walk-on to scholarship athlete**, proving that discipline and consistency create opportunity.

Today, he is the **Founder & CEO of Too Cool Alkaline Water**, an entrepreneur in the beverage and vending space, and the **President of Team America**, a nonprofit dedicated to helping athletes grow through education, exposure, and leadership development.

Gerald is deeply committed to **mentorship, alumni engagement, and preparing athletes for life after sports** — financially, professionally, and personally.

---

**Connect with Gerald Hearns**

- **Facebook:** Gerald Hearns

- **Instagram:** @GeraldHearns | @TooCoolWater

- **LinkedIn:** Gerald Hearns

At **Alumni Direct**, we believe the athlete journey doesn’t end at the final whistle — it evolves.

If you’re navigating life after sports, exploring entrepreneurship, or looking for a community that understands the transition:

👉 **Join the private platform built exclusively for athletes, creators, and leaders:**

[**https://www.alumnidirect.com/**](https://www.alumnidirect.com/)

Because the transition is easier — and far more powerful — **when you don’t walk it alone.

Connect with Alumni Direct:**

- Website: [alumnidirect.com

- Instagram: [@alumnidirect]

- X (formerly Twitter): [@alumnidirect]

- Facebook: [Alumni Direct]

- LinkedIn: [Alumni Direct]

In this episode of Athletes to Entrepreneurship: The Alumni Journey, host Rob Finkelstein sits down with Chris Izmirlian, founder of Job Commander — a compatibility-based hiring platform designed to fix what’s broken in traditional recruiting.Chris breaks down why resumes fail most job seekers, how hiring managers spend just 3–6 seconds reviewing applications, and why ghosting has become the norm instead of the exception. Job Commander flips the model by focusing on who fits, not just who checks boxes — blending hard skills, soft skills, personality traits, and values into smarter job matching.This conversation is especially powerful for student-athletes and emerging professionals navigating career transition — people with discipline, leadership, and coachability who often struggle to translate their experience onto a resume.At its core, this episode is about: Compatibility, fairness, feedback, and restoring humanity to the hiring process.What You’ll Learn in This Episode:🧠 Why Resumes Are Broken: The truth about how little time recruiters spend reviewing applications.🤝 Compatibility Hiring Explained: How Job Commander matches people based on who they are, not just keywords.📄 Beyond the Resume: Why resumes fail to capture leadership, teamwork, and adaptability.🤖 AI in Recruiting: How AI is reshaping hiring — and where it helps vs. hurts.📬 Ending Ghosting: Why every applicant deserves a response, even if the answer is no.🎓 Student-Athlete Advantage: Why athletes are ideal candidates — and how Job Commander helps translate their value.🚀 Streamlined Hiring: How simplifying applications benefits both employers and job seekers.🔄 Career Transitions Done Right: Supporting emerging talent through clarity, feedback, and fit.About Chris IzmirlianChris Izmirlian is the founder of Job Commander, a compatibility-based hiring platform built to modernise recruiting by focusing on fit, fairness, and feedback. His mission is to eliminate ghosting, reduce bias, and help employers connect with high-potential talent — especially student-athletes and emerging leaders transitioning into the workforce.Chris is passionate about using technology to connect people, humanise hiring, and create better long-term employment outcomes.🔗 Connect with Chris: [https://www.linkedin.com/company/jobcommander](https://www.linkedin.com/in/christopher-izmirlian/)At Alumni Direct, we help former athletes build meaningful communities long after the roar of the stadium fades. If you’re navigating a career transition, exploring entrepreneurship, or looking for peers who understand the journey — you’re not alone.👉 Join the private platform built exclusively for athletes, creators, and leaders:https://www.alumnidirect.com/Because the transition is easier — and far more powerful — when you don’t walk it alone.

In this week’s episode of Athletes to Entrepreneurship The Alumni Journey, Rob Finkelstein sits down with former NFL offensive lineman and Tully co-founder Adam Redmond— an athlete who went from Harvard football to the NFL, and then forged a new identity as a builder in the sports-tech world.

Adam opens up about the real challenges athletes face when the final whistle blows: rebuilding identity, expanding your network beyond the locker room, understanding life after sports, and pursuing new passions with the same discipline you brought to the game.

This conversation is a masterclass for any athlete navigating transition — especially those stepping into entrepreneurship, tech, or leadership roles beyond the field.

The heart of this episode?

reinvention, relationship-building, curiosity, and the courage to chase interests beyond the sport.

What You’ll Learn in This Episode

- 🏈 Sports Was the Foundation: How Adam’s competitive mindset and discipline shaped every chapter of his journey.

- 🎓 Harvard to the NFL:*What it taught him about pressure, preparation, and the value of academic and athletic balance.

- 🚀 Building Tully:** Why Adam co-founded a sports-tech company focused on simplifying athlete performance data — and how it’s changing youth sports.

- 🤝 **Networking the Right Way:** Why true networking is about *relationships*, not transactions… and how that mindset opened unexpected doors.

- 🎯 **Preparing for Life After Sports:** The role Harvard’s career services played, and why athletes must explore interests early.

- 📊 **Performance Data, Simplified:** How Tully removes the friction of collecting and analyzing athlete data for coaches, parents, and organizations.

- 🔍 **Identity Beyond the Game:** Adam’s honest look at the challenges of stepping away from the NFL and building a career from scratch.

- 🧭 **Chasing Curiosity:** Adam’s advice for athletes: *follow your interests, build real relationships, and allow the next chapter to unfold.*

---

About Adam Redmond

A former **Harvard offensive lineman** and **NFL player**, Adam Redmond spent multiple seasons in the league before transitioning into entrepreneurship. Today, he is the **co-founder of Tully**, a sports-tech platform designed to streamline performance data collection for athletes and coaches at all levels — especially youth sports.

Adam is passionate about athlete transitions, relationship-driven networking, and empowering the next generation of athletes through accessible technology.

🔗 Connect with Adam:

https://www.linkedin.com/in/adam-redmond-30a49757/

---

Special Invitation from Alumni Direct**

At **Alumni Direct**, we help former athletes build meaningful community long after the roar of the stadium fades. If you’re navigating your own transition, exploring entrepreneurship, or simply looking for peers who understand the journey — you’re in the right place.

👉 **Join the private platform built exclusively for athletes, creators, and leaders:**

https://www.alumnidirect.com/

Because the transition is easier — and far more powerful — when you don’t walk it alone.

In this week’s episode of Athletes to Entrepreneurship: Alumni Journey, Rob Finkelstein sits down with NBA Champion, broadcaster, and Chosen Family Wines founder Channing Frye — a player who spent 14 years in the league, reinvented himself multiple times, and now uses his platform to help others navigate life after the game.

Channing opens up about the emotional, mental, and spiritual shift that happens when the final buzzer sounds on a pro career. From seeking therapy… to rediscovering hobbies… to redefining identity as a husband, father, and entrepreneur — Channing brings raw honesty and real guidance to every athlete facing transition.

This conversation hits the heart of what so many retiring athletes feel but rarely talk about:

identity, reinvention, self-care, and the courage to start over.

What You’ll Learn in This Episode

🧠 Why Every Retired Athlete Needs a Therapist: The transition out of sports is emotional, and professional support can be a game-changer.

🔄 The Art of Reinventing Yourself: How Channing approached redefining who he was beyond basketball.

🎨 Exploring New Interests: Why discovering hobbies and passions outside sports is essential to building a fulfilling next chapter.

🧘 Protecting Your Personal Time: How giving yourself space prevents resentment and fuels healthier relationships.

👨‍👩‍👧‍👦 Balancing Family & Self-Care: The honest realities of shifting from a structured athletic life to the rhythms of home.

🎁 Seeing Retirement as a Gift: How the post-career season can open possibilities you never considered.

🔍 Identity After the Jersey: Why understanding who you are now is the foundation for every next step.

About Channing Frye

A former NBA forward and 2016 NBA Champion, Channing Frye played 14 seasons with teams including the Knicks, Trail Blazers, Suns, Magic, Cavaliers, and Lakers. After retiring, he transitioned into broadcasting, entrepreneurship, and winemaking — founding Chosen Family Wines, now one of the most respected athlete-led wine brands.

Today, Channing is an advocate for athlete mental health, reinvention, and living fully in the next chapter of life.

🔗 Connect with Channing:

https://www.linkedin.com/in/channing-frye/

Special Invitation from Alumni Direct

At Alumni Direct, we’re committed to helping former athletes build meaningful community long after the cheering stops. If you’re navigating transition, looking for peers who “get it,” or ready to build your next chapter with support — you’re home.

👉 Join the platform built for athletes, creators, and leaders:

https://www.alumnidirect.com/

Because no one should walk the post-career journey alone.

In this week’s episode of **Athletes to Entrepreneurship: Alumni Journey**, Rob Finkelstein sits down with former NFL running back **Paul Perkins** — an athlete who took the discipline, grit, and preparation he learned on the field and channeled it into a bold entrepreneurial venture: **SipTale**, a fast-rising canned cocktail brand redefining the category with a non-carbonated twist.

SipTale didn’t emerge from a mastermind retreat — it was built through trial, testing, failed batches, new ideas, and an unwavering willingness to keep going. Paul opens up about the reality behind the launch, the influence of his football background, and the mindset required to stand out in a crowded alcohol market.

This conversation goes deeper than business. Paul shares why he’s passionate about creating experiences that bring people together, avoiding the negative stories often attached to the industry, and helping others along the way. His honesty, work ethic, and grounded perspective make this a powerful episode for any current or former athlete exploring life beyond the game.

This episode uncovers the themes that shape Paul’s entrepreneurial journey:

**reinvention, resilience, ownership, and building with purpose.**

*What You’ll Learn in This Episode**

- 🍹 **Building a Better Cocktail:** Why SipTale chose non-carbonated canned cocktails — and how they launched with standout flavors like **Strawberry Margarita** and **Lemon Sidecar.**

- 💼 **Translating NFL Discipline to Business:** How the habits Paul built as an athlete fuel his entrepreneurial focus today.

- 🔎 **Standing Out in a Crowded Market:** What it takes to differentiate a product in a saturated space and why marketing matters more than most people think.

- 📱 **The Power of Social Media:** How Paul uses online platforms to build community, connect with customers, and grow SipTale’s presence in the Arizona market.

- 🤝 **Mission Over Hype:** Why protecting people, avoiding “sad stories,” and helping others succeed are core parts of SipTale’s purpose.

- 🔄 **The Entrepreneurial Mindset:** How embracing different perspectives — including his brother’s — pushes the business forward with more clarity and creativity.

About Paul Perkins**

**Paul Perkins** is an ex-NFL athlete who has carried the discipline and resilience he developed on the field directly into entrepreneurship. Alongside his brother, he founded **SipTale**, a canned cocktail company rooted in innovation, authenticity, and the mission to bring people together through unforgettable drink experiences.

🔗 **Connect with Paul & SipTale**

Instagram: **@SipTale**

Facebook: **SipTale**

TikTok: **@SipTale**

*Special Invitation from the Guest**

SipTale is rapidly growing across Arizona — and Paul wants people to experience it firsthand.

👉 **If you’re in Arizona, come try SipTale and taste the new standard in the canned cocktail space.**

---

### **At Alumni Direct, we’re committed to helping former athletes build meaningful community long after the game ends.**

If you’re navigating transition, building a business, or searching for a circle that understands your journey — this is your place.

👉 **Join a community built for athletes, creators, and leaders:**

https://www.alumnidirect.com/

Because no athlete should have to navigate their next chapter alone.

In this week’s episode of Athletes to Entrepreneurship: Alumni Journey, Rob Finkelstein sits down with former professional basketball standout Keaton Nankivil — a Madison-born Badger who took his game across Europe before stepping into a new arena: venture capital.

Keaton’s transition wasn’t a straight shot. From the highs of competing in Germany, Spain, Latvia, and Italy… to the quiet space that followed his retirement, he opens up about the identity shift every athlete eventually faces. His honesty, perspective, and humility make this a conversation every current and former athlete needs to hear.

This episode dives deep into the themes that shape life after sports:

*healing, reinvention, community, and rediscovering purpose.

-What You’ll Learn in This Episode

- 🧭 Navigating the Transition:** Why stepping away from sports requires emotional recovery — and why athletes should give themselves the space to breathe before rushing into “what’s next.”

- 🤝 The Power of Community:** How leaning on trusted people can accelerate clarity and confidence during transition.

- 🚀 A New Path in Venture Capital:** What drew Keaton into early-stage investing and why he’s committed to the intersection of **sports, culture, and human connection**.

- 🔄 Redefining Identity:** How to move from “I’m an athlete” to “I’m a builder, creator, and contributor” in the next chapter.

- 🌍 Sports & Humans First:** An inside look at how Keaton and Alumni Ventures invest in companies that bring people together and unlock human potential.

---

About Keaton Nankivil

After starring at the **University of Wisconsin**, Keaton spent five years playing professionally across Europe before transitioning into venture capital. Today, he leads the **Sports & Humans First** practice at **Alumni Ventures**, backing founders who elevate human experience and connection.

🔗 Connect with Keaton:

https://www.linkedin.com/in/knankivil/

#Special Invitation from the Guest

Keaton and Alumni Ventures operate an **Investment Syndicate** that gives **accredited investors** access to early-stage startups in the sports + human-connection space.

Sign up free — *no obligation to invest:

👉 https://www.av.vc/human-first-syndicate

---

Alumni Direct**, we’re committed to helping former athletes build meaningful community long after the roar of the crowd fades. If you’re navigating transition, craving connection, or looking for a place where your next chapter is supported — you’re in the right place.

👉 Join a community built for athletes, creators, and leaders:**

https://www.alumnidirect.com/

Because no one should walk the post-career journey alone.

In this episode of Athletes to Entrepreneurs: Alumni Journey, Michael Lynch reflects on his early years growing up in a single-parent household and how sports helped shape his identity and purpose. He opens up about lessons learned from his father—who also served as his baseball coach—and how teamwork, character building, and perseverance became guiding principles both on and off the field.From his days as a student-athlete to his impact as a changemaker, Michael’s story is a reminder that the values built through sports—discipline, teamwork, and leadership—can drive meaningful change far beyond the game.---Key Takeaways- Sports were a foundation of Michael’s identity and community.- Growing up in a single-parent home taught him resilience and adaptability.- His dad’s role as both father and coach deeply influenced his character.- Lessons from teamwork and competition helped him navigate life’s challenges.- Family life revolved around sports and the relationships it created.- The discipline and character built through athletics became tools for leadership and service.--- Connect with Improve Your Tomorrow (IYT)- Instagram: [@iyt_official](https://www.instagram.com/iyt_official)- Facebook:* [IYT Main](https://www.facebook.com/IYTMain/)- **LinkedIn:** [Improve Your Tomorrow](https://www.linkedin.com/company/improve-your-tomorrow)- YouTube:** [IYT Channel](https://www.youtube.com/channel/UCKXkwgVQELw9a7uweA8XEJg)---Connect with Alumni DirectJoin the **Alumni Direct** community — where athletes, alumni, and professionals come together to network, share experiences, and access resources that support life beyond the game.- 🌐 **Website:** [alumnidirect.com](https://alumnidirect.com/)- 💼 **LinkedIn:** [Alumni Direct](https://www.linkedin.com/company/alumni-direct/)- 📸 **Instagram:** [@alumnidirect](https://www.instagram.com/alumnidirect/)- 👍 **Facebook:** [Alumni Direct](https://www.facebook.com/alumnidirect/)- 🐦 **X (Twitter):** [@alumnidirect](https://twitter.com/alumnidirect)- 🎥 **YouTube:** [Alumni Direct](https://www.youtube.com/@alumnidirect)Discover meaningful connections, business and career opportunities, and a community built to support your journey after sports.---Tune InListen now on *Athletes to Entrepreneurs: The Alumni Journey* — where former athletes share how the lessons from sports helped shape their journeys into entrepreneurship and leadership.

In this powerful episode of Athletes to Entrepreneurs: The Alumni Journey, host Rob Finkelstein sits down with William Person, a former nine-year Team USA Bobsled athlete whose career and life were forever changed by CTE (Chronic Traumatic Encephalopathy).

After years of competing at the highest level, William faced the devastating effects of CTE — confusion, depression, and loss of clarity — until discovering Hyperbaric Oxygen Therapy (HBOT). The treatment helped him regain focus, restore his energy, and reignite his purpose.

Today, William is on a mission to raise awareness about brain injuries in sports, fight for transparency for youth athletes, and build a nonprofit CTE Recovery Center to help athletes, veterans, and civilians heal at no cost.

💡 In This Episode:

• William’s journey from college track athlete to Team USA Bobsled

• The mental and physical toll of CTE on former athletes

• How hyperbaric oxygen therapy changed his life

• The challenges of transitioning out of competitive sports

• Why networking and purpose are vital for athletes post-career

• William’s mission to build a CTE Wellness Center and educate future generations

• Athletes face major challenges transitioning after sports.

• CTE is a silent battle that many former athletes face without support.

• Networking and connection are critical for post-career success.

• Hyperbaric oxygen therapy can play a major role in brain recovery.

• William is leading the charge for transparency and long-term brain health in athletics.

Help William open a CTE Recovery Center to provide free treatment for athletes, veterans, and civilians suffering from brain injuries.
Your donation helps fund a medical-grade HBOT chamber, housing, and travel costs so those in need can receive care at no cost.
👉 Donate Here: https://gofund.me/93ff9c6e

📘 Facebook:

• One Man with a Chamber HBOT

• William Person

💼 LinkedIn:

• William Person

📸 Instagram:

• @willp1234567

▶️ YouTube:

• Brain Injury Survival

🎵 TikTok:

• @hyperbarichealing

  
  

  
  

Alumni Direct helps former athletes, entrepreneurs, and professionals stay connected beyond their careers. Join a supportive community that empowers meaningful relationships, mentorship, and new opportunities.

🌐 Learn more and connect today: www.alumnidirect.com
💬 Follow us on LinkedIn: Alumni Direct

🎙️ Athletes to Entrepreneurs: The Alumni Journey explores how former athletes channel their drive, discipline, and teamwork into new ventures and purpose-driven lives beyond the game.

#AthletesToEntrepreneurs #WilliamPerson #CTEAwareness #BrainHealth #HyperbaricOxygenTherapy #SportsRecovery #MentalHealth #AthleteTransition #AlumniJourney #RobFinkelstein #AlumniDirect