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The Entrepreneurist: Jordan Fliegel

David Mielach
Updated Jun 29, 2022

Jordan Fliegel was able to take his passion for sports and turned it into a successful small business. That business, CoachUp, helps athletes find private coaches in a number of sports.

When Jordan Fliegel was in high school he met a private basketball coach who changed his life. Fliegel has been able to take the lessons that coach taught him on the court and apply them off the court to his startup CoachUp, which now has more than 9,000 coaches for athletes in more than 60 sports. BusinessNewsDaily spoke with Fliegel about how passion played a role in his business, why he loves being a business owner and why business owners should always follow their gut instincts.   

BusinessNewsDaily: What did you want to be when you grew up?

Jordan Fliegel: It changed over time. I first wanted to be the guy who rides on the side of the trash truck, because that was the coolest guy that came down my street every day. There were a few other things, and then I discovered basketball, and I wanted to be a pro.

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BND: What did your parents do for a living?

JF: My dad was a writer and consultant, my mom is a writer and editor. Both are retired now and spend their time writing and doing fun stuff. I see them both every week. 

BND: Can you talk a little about your businesses and how you got your start?

JF: In high school, I realized that probably wouldn’t go pro and I went to Bowdoin College. I got an offer to play pro basketball overseas and jumped at that.  I wasn’t able to make it to the NBA, but I did fulfill my childhood dream and played pro for 2 years in Israel and Europe after college. From there I went to business school, and then got into the startup world. Now I’ve found my true calling, and have devoted my life to building great companies with my friends. I was an average high school basketball player who through sheer luck, stumbled upon a great private coach, Greg Kristof, who fundamentally altered the course of my life.

I later became a private coach, to give back and pay forward what I had learned. I wanted to make the same impact for other athletes that Greg had done for me. Private coaching did more for me than just make me a better basketball player, and help me get into a great college. It taught me the value of hard work, and instilled in me for the very first time the belief that I could achieve anything I set my mind to. That quiet confidence and work ethic has spilled over into all aspects of my life. I founded CoachUp because I want every athlete who has a sports dream to receive the help they need to reach the next level in sports and in life. 

BND: What’s the best part of owning your own business?

JF: Being able to hire awesome people who make the company even stronger. 

BND: What’s the biggest mistake you’ve made as an entrepreneur?

JF: Not trusting my gut on core decisions. I’ve done it a few times, and it never works out well!

BND: What was your main motivation in starting this business?  

JF: Change the world. Sounds cliché, because everyone says that, but I want to build a company that really matters. We are helping thousands of people make a living doing what they love, and we are helping thousands of people get better at what they love doing. We are really changing lives. Our mission is one of the strongest assets we have. The people at CoachUp love what we are doing, and believe in the value of it. That motivates us to work hard every day. 

BND: What previous experiences helped you in that journey?

JF: Being an athlete and being a private coach helped tremendously. We guide all of our product decisions at CoachUp based on how helpful the new functionality is to our athletes and our coaches. I also learned a lot at my first job after business school, another online marketplace called I worked there before starting CoachUp, and learned a lot about person-to-person marketplace businesses, and became very attracted to that business model. 

BND: What was the biggest challenge you encountered and how did you overcome it?

JF: It’s been pretty smooth sailing for us, to be honest. Every day brings its own set of challenges, but we have a great team of super-smart, ambitious, and enthusiastic people at CoachUp who push each other to be better every day. If anything, we have so many exciting projects with great potential, and the challenge is staying focused on core things that really matter. 

BND: What is the best bit of advice you have for other entrepreneurs?

JF: Just be yourself. Work hard, and do something you love. Focus: do less, but do it better. And give back when you can.

Image Credit:

Jordan Fliegel / Credit: Jordan Fliegel | CoachUp