It was the summer before 7th grade, and I was too young to get a job. My brother James was allowed to work at Young's Bike Shop, a Nantucket Classic while I was supposed to spend another summer going to day camp. Not that I didn't love Strongwings, I was just ready for the independence cash grants a ten year old.
Disappointed with my lack of opportunity, I walked into the Tennis Loft, a new store open opened by my father's old tennis pro, Tina Hoskins-Burney. If complete strangers won't give me a job, maybe Tina will! Unfortunately, friendship wasn't enough to overcome child labor laws. Instead, Tina offered to teach me how to string tennis racquets. For the next four weeks, every Tuesday and Thursday I watched her string, and by the fifth week I was allowed to weave my first crosses.
At the end of the summer I convinced my parents to provide me the capital to start a racquet stringing company serving my father (a voracious tennis player), his friends, as well as Middle School, squash team, and whomever else needed a racquet restrung.
For the next three years I built the business in my spare time, keeping a refined log book of customers, and even starting a rewards program. The first website I ever built was an up-to-date inventory of the strings I had in stock as well as an expected wait time. At its peak I was stringing between 5 and 7 racquets a week.
My freshman year of High School I started playing lacrosse. During tryouts a friend's strings snapped making his lacrosse stick useless. When no one knew how to string the head, nor where to get it strung, I jumped at the opportunity. I learned how to string and die Lacrosse heads. By the time I was ready to string my first customer's head, the season was halfway over. And as I so painfully learned, despite buying string, die and carving a spot in the garage, lacrosse strings don't fray that often. Over the entire season I had one customer; the friend from week one had found a shop to do it, and referred me a friend out of sympathy. Tennis and Squash were much more lucrative markets.
By the time I left for boarding school for sophomore year in Highschool I had made more than enough money to make up for my losses in my unsuccessful expansion plan pay my parents back for the machine and be profitable.