My Strange Path to Entrepreneurship

Yesterday, I took a walk with my friend Jeff to get some advice. During the walk, he asked me about my job history and seemed fascinated by some of the twists and turns I have taken. His response to my story was, “You need to blog more about that!” so I am. I thought I would start with a quick list sharing with you the path that led me from starting my first nonprofit to starting Sideways8.

Here goes!

  • My senior year of high school some friends and I started a nonprofit that over three years would serve the homeless in Little Five Points, put on two large youth rallies, run a climbing and outdoor program, and run a monthly coffee shop for college students downtown.
  • During college at Georgia Tech, I took on my first website client. That client was Asby Sewing Company, and they are still a client of Sideways8 today.
  • Two weeks after graduating Georgia Tech in 2003 I got married to my lovely bride.
  • Two weeks after we got married we moved to Cleveland TN, where I took a job as a sales person for Cingular Wireless in Chatanooga.
    • Interestingly, my first sales position at Cingular was at a kiosk in a Walmart. Listening to the cashiers swipe items that go “beep” over and over, all day, was a little maddening.
    • While living in Cleveland, I was also a youth pastor at a small country church.
  • After about a year and a half, we were ready to come home, so I took a job as a Student and Community Minister in Austell, GA (the city where I went to high school just outside of Atlanta).
    • During this time I also taught kids gymnastics, something I had done in college.
    • I also built websites during this time to help make ends meet, since ministry didn’t pay much.
  • Two years later I took an internship at a mega-church to learn how to plant (start) a church.
  • In 2008, my wife and I started Decatur Gathering Church in downtown Decatur, GA. We had meetings in the old courthouse on the square, which was an amazing venue. But, things didn’t go well, and the church didn’t make it.
  • As the church was failing, I took a job as a long-term substitute teacher for seventh-grade special ed. I loved it, so much so that I took the GACE to become provisionally certified to teach middle school and was planning to do that professionally. That was the year that they started firing teachers because of the economic downtown, so I moved on to something else.
    • I also built a lot of websites during this time, basically working three jobs to make ends meet.
  • In the wake of the failed church plant, our family moved into the basement of another family and lived with them for 18 months. We had our third child and brought her home to that basement.
  • When being a teacher didn’t work out, I got a call out of the blue to interview for a job as a graphic designer at an agency doing some cool work, so I went. I was a self-taught¬†graphic designer and underqualified for the job by a mile, but somehow I got it.
  • After two months as a professional graphic designer, it was obvious to me that it wasn’t working. My stuff wasn’t good enough for them to use, I knew it, they knew it. So, when the boss wanted to meet with me, I knew it was to let me go. I was glad he did, for him and me.
  • Having been freshly fired for the first time in my life, I decided I could build an agency as good, or better than those guys. I called up Aaron and finally convinced him to start a company, and in mid-2010 Sideway8 was born.
  • Now our company that started with 1.5 full-time people has seven full-time people and 5 part time people, and we are still growing quickly.

I’m thankful for the weird path that my entrepreneurial journey has taken. Over the course of my life, I have started three nonprofits and two companies. One nonprofit and one company have lasted, I figure two for five isn’t too bad. One thing I have learned on this journey is that failure is not only ok but expected. Setbacks come, time and again, and it is only the people that push through them that will make it. My journey has taught me to push through, and for that, I am profoundly thankful.

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