5 Former College Athletes Share The Lessons From Sports That Help Them Lead As CEOs


“Leadership is an ever-evolving position.” Those words from Duke’s Coach Krzyzewski evoke the fact that leadership is a journey, ever-changing based on circumstance. As arguably the greatest coach and leader in college basketball, Coach K understands that leadership isn’t just a name or title. Within himself and the athletes he grooms as leaders, leadership is a demanding position that requires constantly getting the best out of your team.

If leadership is an ever-evolving position for athletes, how does it play out outside the confines of sport? When athletes move on, the lessons they learn must be applied to new teams, settings, and professional environments. What does leadership look like on the other side? And how does it evolve for athletes over time? We talked to five former college athletes that are now founders or CEOs. While their leadership styles are all grounded in the foundation of sports, they each take different lessons and advice that inform their approach to managing their teams. The Coin Flyp asked each of them a few questions to unpack how they lead and what their transitions were like.



CEO & Founder, Tru.Inc

Former Professional Hockey Player (Denmark, Slovakia, and Norway), Men’s Hockey ‘12 | Colgate University

Greatest Piece of Advice He’s Received: Just before heading to Sweden to play junior hockey, my uncle told me, “If you are given an opportunity to experience something new that puts you totally outside of your comfort zone, do it.” Despite being exhausted, nervous, or full of anxiety in those moments, not once have I looked back and regretted the experiences of seeing new cultures, meeting new people, and learning from others perspectives. Successful entrepreneurs live in discomfort and find a way to thrive in uncommon situations.

Failure After Sports He’s Learned The Most From: Following a couple of years of pro hockey in Europe, I felt an unearned level of confidence in entrepreneurship. My naivety led me to invest close to $10k in a botched manufacturing run in China as I thought that it would be easy despite no experience. It was the greatest lesson that I could have learned as it taught me the power of knowledge, research and asking the right questions. This lends itself to not only a higher success rate, but also, better relationships and more respect in partnerships.

Biggest Lesson From Sports That Informs How Jack Leads: The power of body language is perhaps the most underrated form of communication in both sports and the workplace. At an early age, my mother, a Boston College tennis Hall of Famer, taught my brothers and I that everyone can’t hear what you are saying on the ice, but everyone can see how you carry yourself. As a leader in business, everyone can’t always hear what you preach, but I guarantee that they take notice of how you carry yourself. Shoulders back armed with a firm handshake and a genuine smile go a very long way.

Advice to Athletes About to Transition: Don’t wait. All to often, I hear of young graduates complaining that they don’t know what to do with their life or at the next stage of their journey. I say, pick anything and at least that way you can cross something off your list that you don’t want to do. Sitting around solves nothing. And if you do know, dive right in and meet with as many people as possible until you find a way into that gig. Persistence can be the most powerful tool of growth, while complacency leads to personal erosion.


CEO & Co-Founder, Trey Athletes

University of Kansas ‘08 | Women’s Basketball

Greatest Piece of Advice You’ve Been Given: My family has always encouraged me to "go for it," regardless of what "it" was. Leaving my town of 80 people to play basketball at Kansas. Moving to New York to become a CPA, without knowing a soul. Switching career paths to move to Switzerland, and later, Bolivia. Completely changing course to earn my MBA from Harvard and co-found Trey Athletes. And many more smaller dreams and calculated risks. No one wants to see people they love struggle, which is why the "go for it" attitude they’ve consistently had creates a special kind of freedom: the freedom to try.

Failure You’ve Learned The Most From: I once received feedback that I was too direct and impatient. In my mind, I was just continuing the competitive, results-oriented approach I was used to. I realized that my approach was not always appropriate or productive in a workplace, so I started observing the supervisors, and saw how they were able to hold others accountable while still keeping them motivated and excited about their work. It taught me that inspiration often produces greater results than fear. Inspiration is much harder to do, which is why I think so many people (in sports, business, and otherwise) default to using fear.

Biggest Lesson From Sports That Informs The Way She Leads Trey Athletes: Leaders come from all roles and personality types. Prior to college, I always assumed that the star performer was the de facto leader. I've since learned there is no singular type of leader; instead, there are many different leadership styles, each with their own pros and cons. A leader serves others by investing in them and bringing them together in pursuit of a bigger goal. If no one is willing to follow you, because they don’t trust and respect you or believe in your vision, then you might be a star, but you aren’t a leader.

Advice to Athletes About to Graduate:

  1. Make thoughtful and engaged decisions. With so much going on between school and sport, don’t become a passive actor in your own life. Take control of the things you are learning, the experiences you are getting, the people you are meeting, and the goals you are setting. Every month, you should reflect on what happened, how you felt, and how it impacts the next month of your life. It could be a word document, a video recording, a poem, or whatever works for you, but you need to zoom out regularly to keep yourself on the right path.

  2. Broaden your network. Seek out non-athlete friends. The fact they are having a fundamentally different college experience is a good thing; it means you have a lot to teach one another. Find the commonalities in your experience,  learn how they spend their free time, how they view college, and how they are preparing for careers. This will broaden your perspective on what is normal, and provide you with a diverse group of friends for the rest of your life.

  3. Practice transitioning your skills. Yes, you are crazy busy. That doesn’t mean you can’t stop by career services for help building a skills-based resume or to participate in a mock interview. Building skills in sport doesn’t mean you can communicate them to someone else or apply them in the real world. A crucial part of this is to get traditional work experience. You may train year-round and can’t do a standard 8-10 week internship, but that’s not an excuse. That week off between post-season and the start of off-season conditioning? Set up a 3-day job shadow. Your favorite people in the athletic department? Ask if you can help out around the office one afternoon a week. The boosters who come to team events? Form genuine relationships with them by sharing your story and asking them about theirs. There are people around every corner who can help you transition your skills, and it’s up to you to seek them out.


CEO & Co-Founder, Jopwell

Yale University ‘11 | Men’s Basketball

Greatest Piece of Advice He’s Been Given: In the early days of Jopwell, I had the incredible opportunity to meet with a hero of mine, NBA legend Magic Johnson, whom I am now lucky enough to have as a mentor. I told him I was having trouble finding my footing in the corporate world since being an athlete had shaped my identity for so long. Mr. Johnson knew how I felt and shared insight on how he was able to successfully transition from basketball player to businessman. He explained that the character traits that he gained from playing basketball — discipline, adaptability, hard work, confidence, competitiveness, and teamwork — allowed him to carve out his own niche in the business industry and differentiate himself from his competitors. He didn’t tell me exactly what to do but rather showed me that I, too, had transferable skills that could be applied to the business world. Hearing his story made me realize that each of us has our own unique gifts and talents that can help us deliver value at work and grow our careers, and that was great advice.

Career Failure He’s Most Proud Of: When I told my parents that I wanted to leave finance to launch Jopwell, they told me I was crazy. One on hand, they were right. I had no experience in tech, recruiting, raising capital, or managing employees, and I was sure to face additional barriers just by being a Black man. On the other hand, they were wrong! I had a sound idea and the right co-founder, and knew I could do it. But I learned a ton from their doubts. If I was really going to do this — essentially ignore the people who are looking out for me — failure was not an option. Now I have an opportunity and a responsibility to help pave the way for future founders of color, so while venturing into unknown territories was exciting and nerve-wracking at the same, I am so glad I took the leap.

Biggest Lesson From Sports That Informs How He Leads Jopwell: I’ve been lucky enough to have several incredible coaches in my basketball career, and I think there are many parallels between a good coach in the sports world and a good manager in the corporate world. This is something I talk a lot about in my new book Let Them See You. In any game, winning is the ultimate goal, but it’s always more complex than simply scoring more baskets, and a good coach knows that. A coach knows that each team member has distinct responsibilities and goals and adds value in different ways. When everyone involved knows the playbook and understands how and where to contribute, wins come easily. If, on the other hand, each player tries to score every time they have the ball, the game ends up a confused mess. We’ve all seen little kids swarm a soccer ball like its magnetic. This team will almost certainly lose, and the locker-room culture will soon become tense and toxic as players feel disgruntled. In both cases, it’s up to the coach to create a framework for the players to succeed, to teach them the playbook, and make course corrections as needed. The same is true at work—each team member has a playbook to follow and a role to play according to their skills and abilities; each offers unique ways to contribute to successful business outcomes, and it’s up to the manager to steer everyone toward the same goals.

Advice to Athletes About To Graduate: Being a student-athlete prepares you for the workforce like nothing else — you’re disciplined, you know how to be a good team player, how to get your work done in the time you have available, and that practice makes perfect before a big game or presentation. My main advice to student-athletes would be to identify those elements that made you the best in your sport and position, and apply that same athletic mentality to your career.


CEO & Co-Founder, BlackFem & On A Wealth Kick

Amherst College ‘14 | Women’s Soccer

Greatest Piece of Advice She’s Been Given: “Slow the fu** down.” I’ve actually had 3 different mentors tell me this, and I’ll be honest I didn’t listen for about a year or even longer. Similar to a fitness test, we are so desperate to pass (and we have likely prepared for the agony) that we take off at the start. This burns you out. The burn out is REAL!

I’ve also realized that the clearer your vision is the faster/better it can become a reality. If you’re moving too fast, you have no time to make sense of what’s going on in your head.

Failure She Learned The Most From: I won’t say when (because it was somewhat recent), but I fired every single employee I had. This is an immense failure because hiring is single-handedly the leader’s role. It was also the absolute BEST thing for my business, but it was one of my greatest failures because it was proof that I was doing things without a sound strategy and spending more time trying to be liked than being a leader.

Biggest Lesson From Your Sports Career That Informs The Way She Leads: There is not a single person on this planet who would call me a “pretty” or “elegant” soccer player. I mean in high school the basketball girls used to call me “tank.” I was scrappy, aggressive, boisterous, but effective as hell. What I learned from my sports career is that it doesn’t always have to look pretty (your marketing docs do though!). What I really mean is you don’t have to have all the answers to be effective and successful. You have to just be you. And in fact, because I was such a different type of player, I was harder to defend. Because my businesses reflect the type of person and player I was, it’s been hard for others to compete.

Advice to Athletes About to Transition: Don’t stop training! Getting back into shape sucks. Being an athlete was so addicting for me because it’s when I experienced my greatest (and longest) periods of bliss. It’s a story every time you play. My athleticism and leadership/business-mind are symbiotic. I read a book every morning when I go for a walk or get on the stair climber to activate my mind.

Starting a business and running a startup is like preseason: training sucks! But, it’s worth it to pass those awful preseason fitness tests. If you’re a woman or minority, these proverbial “tests” will feel like you spent all summer messing around instead of training. It’s not your fault, but you need that heads up.

Training your mind will require the same dedication as your workout plan. If you lose your creative energy (which I did when I got too wrapped up in the administrative part of my job), it will take some serious work to get it back. It’s like coming back from an injury.


Co-Founder, Arbit

Loyola University Maryland ‘13 | Men’s Soccer

Greatest Piece of Advice: Fall in love with your customers, not your product. I think too often startup founders (including myself in the early days) have an idea and become tunnel visioned by it. They fall in love with their idea/product, focus on that, and build, build, build, wasting countless resources, time, and precious capital. They let in what they want to hear and ignore what they don't (which is often much more important feedback). Focus on your customer and study their habits and needs to find out how you, your company, and your product can better serve them.

Post Sports Failure That Taught Him The Most: Going off my previous answer, we built several features in our platform before testing ideas and concepts, rather than the other way around. When we were getting started, this is what we thought we were supposed to do. We thought founders have a vision, then builds a product, and then the customers and consumers come. However, this couldn't be more wrong. I think it is important to do a lot of the processes manually to start and not build until it is completely necessary in order to scale your business and increase your efficiencies.

Biggest lesson from sports that informs the way he leads Arbit: It is impossible to build a company on your own. Every successful sports team needs a good coach and in business you need key strategic advisors to help guide you. You need great leaders and captains, similar to your founders and executives. And you need great role players, similar to your employees. Finally, in sports and business you need great communication throughout your team and you need to all be driven to a common goal. Without this balance it is almost impossible to have a successful startup.

Advice to Athletes About To Transition: The transition away from college sports can be very difficult. Often times, you go from being celebrated as an athlete to being just another employee at a large company. While it can be difficult at times to find your way, continue to work relentlessly to get to where you want to be in life, just as you did in sports. If you're not happy with your career trajectory, it is never too late to make a change. Do something that makes you happy and that gets you excited to get out of bed on Monday morning.