This essay is based on a conversation with George Appling. It has been edited for length and clarity.
I started out on the quintessential American Dream path. I grew up in a solid middle-class environment with a mother who was a teacher and a father who was an accountant. Both of my parents were the first generation to attend college, so they were thrilled when I enrolled at Texas A+M University to study business.
After graduation, I was hired by the management consulting firm McKinsey & Company to work as a business analyst. A few years later, the company paid for me to attend Harvard Business School. As a consultant, I traveled all over the world helping companies answer their key strategic questions.
I eventually became an executive, and later CEO, of a private equity-owned cell phone retailer that had over $1 billion in revenue. It was a lucrative job. By the time I was 36, I had $1 million in the bank.
I loved my job and the technology I promoted, but it wasn’t my passion. I was helping wealthy companies get even wealthier, and that was fine, but I didn’t want that to be my whole life. So I took my Blackberry out of my hip holster and wrote a note on my 40th birthday. It simply said, “Quit.” That day, I vowed to stop doing what the world wanted me to do and start doing what I wanted to do.
I traveled the world as an executive and returned home every year for the Renaissance Fair.
The first time I went to a Renaissance Faire was on a middle school field trip, and as soon as I walked in I felt like I had found home, my soul had come into my body and I felt like I belonged here.
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I’ve been going to the Texas Renaissance Festival every year since I was 16, and even when I lived in Australia, England, and Russia for work, I would return home to keep the streak going. I love everything about it: the music, the animals, the artisans.
I did the math and realized there were people making a lot of money running Renaissance festivals. I realized I could create a business opportunity out of my passion. In February of 2010, I co-founded Sherwood Forest Fair, a medieval Renaissance fair outside Austin. I was 40 years old and it was the right time to start chasing my dream.
I went from business meetings to toasting at fairs.
I had enough financial stability that I felt comfortable taking the risk of quitting my CEO job to start the fair, so I focused on building that business for two years, from 2012 to 2014. I also learned more and more about fighting and started performing in sword fighting shows.
I was literally at a fair on my horse one day and an old friend called me about a venture he was starting. I told him I was dressing up and couldn’t talk, but he invited me to come and see his tech. I was so impressed with it that we started a software company together.
Courtesy of George Appling
From 2015 to 2018, I had a foot in both worlds: I was running the fair and building a tech company. I traveled to Barcelona in February just before the fair season to attend the annual tech networking event, Mobile World Congress. I stayed up until 2am before catching a flight to Austin to kick off the fair with a midnight toast.
It was demanding, but I really loved what I was doing.
I currently run eight businesses.
These days, much of my time and attention is focused on the Sherwood Forest Fair. We’re open weekends in March and April and run summer camps in the summer where kids can get hands-on and learn everything from blacksmithing to horseback riding. I also co-own a mead business, sell historical weapons and armor, and rent out our castle.
Additionally, I also do some unrelated activities: I do executive coaching, where I coach people to become “passionate entrepreneurs,” and I also help run an audio software business.
All eight of my businesses are doing well financially. But what matters most to me is the joy the fair and summer camp bring to people. I want this to be my legacy and have set up a trust to continue the fair after I pass away.
When I’m on my deathbed, I want my last words to be, “The show must go on.”
