From Side Job To IWearYourShirt.com: A Startup Story
by Jason Sadler
Taking a paycheck from a 9-to-5 is easy — you show up, you do your work, you get paid. Running your own business? That’s a different story — you show up, you do your work, but if nobody buys into your idea, you don’t get paid, and you risk the possibility that your entire livelihood could come tumbling down around you.
But thinking back to where I was five years ago, I wouldn’t have it any other way.
In 2006, I was about two years into my job as a graphic designer for the ATP World Tour (men’s professional tennis). Like most entrepreneurs, I felt completely unmotivated to work for someone else. My biggest fear was becoming a complacent corporate drone, so to challenge myself, I started helping a college buddy get Web design work on the side. What began as sending off a few emails to my contacts turned into hours of work each night, with no promise of any additional income. Still, I found myself excited to check the emails for my gig — constantly thinking about all the great opportunities waiting for me when I got home from my “real” job.
Once I got a taste of the passion and motivation that came with working for myself, I didn’t want to let it go, and began realistically considering leaving my job. I was nervous to leave the security of the corporate world, but didn’t care for the thought of climbing the corporate ladder. The promise of a new job title and a slight bump in salary wasn’t the least bit exciting to me. I started to wake up each morning with dread for the work day ahead.
I distinctly remember having the conversation with my future business partner over dinner. We talked about the six-month salary reserve I had if I decided to leave my 9-to-5 job. We talked about all the “what ifs.” What if we didn’t get any clients? What if we couldn’t pay our salaries? What if? What if? And then I realized that I was “what if-ing” myself out of a great opportunity that had arrived at the perfect time in my life. The next day, I walked into my boss’s office and gave him my two weeks’ notice.
Fast forward a year and a half, and I was the happy co-owner of a successful web design company. We were making money. I wasn’t stuck in a corporate office anymore. I had exactly what I wanted.
But then something happened: a new idea popped into my head. An idea that eventually would consume my thoughts day in and day out. An idea that was all I wanted to talk about and all I wanted to focus my energy on. I wanted to get paid to wear T-shirts. I had tasted the creative freedom of working for myself, but this was an idea that was mine alone. So I began realistically considering pursuing it.
I knew in my gut that there was a huge opportunity to promote businesses using social media, but convincing someone that I could do it with T-shirts was a challenge, to say the least. In those beginning days and months, I took to my contact list and emailed every single person I knew. I didn’t ask them to buy anything or write any press. All I asked was for them to listen to my idea and pass it on if they thought it was worth sharing. It’s amazing what word-of-mouth can do when you come to people humbly and honestly. Soon, the word began to spread and sponsors were pouring in.
But there was another problem. When I started IWearYourShirt.com, I knew I couldn’t just abandon my business partner (or my income) without any certainty that my business would catch on. I tried juggling my side business and helping to run the Web design business, and after a year of wearing both hats, it became apparent that it was time to make another life-changing career career decision. The situation was all too familiar — I wondered, do I stick to working on both ventures, where neither of them get 100 percent of my effort, or do I focus on what I’m passionate about and what I can pursue wholeheartedly?
With a little guidance from family and friends, the decision this time around was much easier. It was time to take that final leap of faith and focus every ounce of my time and energy on bringing my vision to life.
It’s been over three years since I started IWearYourShirt.com, and I’ve doubled in company growth and tripled in revenue each year. I think back to my days at the ATP, and while I gained some valuable experience, I don’t have a single regret about leaving the corporate world to do my own thing.
Is it hard, knowing that your success or failure rests entirely in your hands? Yes. But there is no greater satisfaction than going to sleep at night, knowing that I work for myself and waking up every morning to continue to bring to life an idea that few people thought would succeed. And that feeling is far more valuable than any paycheck.
Jason Sadler, Official T-Shirt Wearer at IWearYourShirt, hasn’t always been wearing T-shirts for a living, but has always been creative. Fox Business has called him the “Entrepreneur of the Century.”