My First Non Soccer Award

LeRoy Watkins with the Patriots super bowl trophies

Growing up, I loved winning. One thing people don’t realize about adult me, is that I am extremely competitive. When I do something, I don’t do it to be ok. I do it to be the best. A lot of that drive nowadays is internal, but when I was younger I wore that on my sleeve. So with soccer, my favorite sport, my goal was to be a pro. I worked my butt off to get good. When it came time to go to college I got a scholarship to play soccer at Northeastern (which I thought was in Chicago at first, but that’s a whole different story for another day). I majored in soccer and because my parents always told me that I should have a backup plan just in case my soccer career got derailed by an injury, I also majored in Finance and Insurance. By the time I left Northeastern I was top 10 in points, captain of the team, and helped lead the school to its first ever NCAA appearance. When the opportunity to move on to the next level presented itself, I decided I was done. For the first time in my life I didn’t have soccer. I needed something to fill that competitive void and I found it with my first job out of college in door to door sales. I can talk for days about this pyramid scheme experience, but for the sake of this story all you need to know is I made it to the top of the pyramid after about 16 life changing months. When the challenge of that experience was starting to wear off, I started MyBike. 

After doing a commission only job, 6 days a week, for 12 hours a day, making the leap to full time entrepreneur was easy. The basic idea behind MyBike was renting bikes with advertising inside the triangular bike frames. Like my door to door sales experience, I can write for days about the start up process for MyBike, but again, for the sake of this story all you need to know is my marketing plan. It consisted of me locking bikes around Northeastern University with advertisements that said Apparently my ad bikes worked because the Boston Globe called to do a story about me, then I was published nationally in Bicycle Retailer and Industry News magazine. After that everyone wanted to feature me. It was crazy. All of those competitive juices that I had in my soccer days and in my door to door sales days were flowing again. It felt great. But through all the press and perceived success, I was losing money hand over fist, so I needed a real job. One thing people don’t know about me is that I hate working for someone. I don’t like having a boss. So when I took a job as a head hunter for Michael Page International, it was out of desperation to pay my credit card bills and to get health benefits to see a doctor. 

I remember this part of the journey like it was yesterday. I was in Target at South Bay Plaza looking to buy stuff for the company, when my gigantic MyBike PDA phone that I couldn’t afford rang. It was BusinessWeek Magazine and they wanted to feature me as a top entrepreneur in America for a 25 under 25 article. My friend Melissa Cohen who was working at Metis Communications hooked it up for me, and I am forever grateful for her. The BusinessWeek writer needed to follow up our phone call with a few questions and we agreed to communicate further via email. All of her emails came when I was at my job at Michael Page and my boss really did not like me doing MyBike stuff on company time. But I genuinely didn’t care as I was secretly hoping the be fired because I thoroughly hated working for someone. Unfortunately I did not get fired, but I did get reprimanded after getting found out. As life would have it, one of my coworkers blew the lid on my quasi secret MyBike emailing during work by yelling, “Yo, LeRoy, you’re on the front page of Yahoo!” Everyone went to Yahoos homepage and boom, there I was, the featured image as one of the top 25 Entrepreneurs in America Under 25. That was really crazy. But what is even crazier is that I just won my first non soccer award. The thought of winning a non sports trophy never crossed my mind. Now that I knew I could compete in business and win stuff, I was even more motivated to be the best. I quit that job and with the help of my mentor, Glen Juszczyk, I started working at Viking Sports February of 2007. 

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