Side hustle hero: The CEO who hit ‘STOP’ and built a medieval empire from passion

At 36, George Appling was at the peak of a high-powered corporate career, a partner at top consulting firms and later CEO of a billion-dollar mobile phone distribution company. By most standards, he’d ‘made it’.

But instead of pushing for more, he made an unusual one-word note on his Blackberry calendar, scheduled for his 40^th birthday.

It read:

‘STOP’.

Intrigued, we caught up with George Appling to find out more.

“I made the ‘STOP’ note when I was 36. I had this vision of marrying my business skills and my passion. I didn’t know exactly what that meant, so I gave myself four years to figure it out,” he told us.

That decision would eventually lead George to swap boardrooms for broadswords and build one of the most successful Renaissance festivals in the United States.

From billion-dollar boardrooms to Robin Hood’s world

George, who was born and raised in El Campo, Texas, didn’t follow a typical ‘side hustle’ path. After studying at Texas A&M University and building a career that included being at partner at both McKinsey & Company and Booz & Co, he climbed to the very top, leading a company with around $1bn in annual revenue.

But something didn’t sit right.

“What ‘STOP’ meant was to stop doing what the economy expected me to do and to rather spend my work energy on something I truly loved.”

That idea simmered for years, until a chance moment changed everything.

“I hadn’t missed a year of the Texas Renaissance Festival near Houston in over 20 years… When a friend told me it was for sale, the clouds parted and the angels sang. I knew then that owning a renfaire [renaissance faire] was the answer to my quest for marrying my skills and my passion.”

Turning passion into a business

In 2010, George and his co-founder Eric opened the Sherwood Forest Faire, a medieval-themed festival set on 25 acres of land east of Austin, Texas.

“We invested heavily to create a permanent theme park even in year one. We also invested heavily in marketing to really “give it a go” in year one. It worked.”

That first year attracted 32,000 visitors across six weekends.

Fast forward to 2025, and the faire welcomed 177,000 people over eight weekends, with 150 shows a day featuring jousting, falconry, theatre and artisan crafts, inspired by medieval England.

The reality behind the scenes

Despite the spectacle, the early days were anything but certain.

“We didn’t know if the marketing would work. We didn’t know if patrons would enjoy the show. We didn’t many things. That was probably the largest stressor.”

And even now, success doesn’t mean smooth sailing.

“Don’t let the drama get you down,” says George. “It will always be there. When you have 2,000 people working on the show, and 177,000 customers, there will be problems. That’s just part of life. There’s no such thing as 10 steps forward. The best life gets is nine steps forward and one step back. So keep calm and carry on.”

It took until 2018, eight years after launch, for the business to become profitable, after an initial investment of around $1m.

A different kind of ‘CEO’

Today, George describes himself as a “passionpreneur”, someone who blends commercial thinking with genuine enthusiasm for what they do.

And he doesn’t just run the event, he performs in it.

“During the faire, I’m an actor,” he tells us. “I’ve played multiple characters over the years. This year (2026) I’m in the Shakespeare troupe called 'The Court Imposters'. We are doing ‘A Midsummer Night’s Dream’ in 27 minutes. It’s a blast.”

He’s also heavily involved in stage combat, serving as the deputy fight director.

When asked what part of running the show he enjoys the most, George says it’s the stage combat.

“There is something deeply bonding about swinging a three-pound steel rod (sword) at your friends. Hearing the audience gasp and cheer during theatre skits is the best.”

It’s a far cry from corporate life, but his business background still plays a crucial role.

“Financial planning keeps me sane, but it’s ‘servant leadership’ [where the leader serves employees and customers, prioritising their needs, growth, and well-being over personal ambition] that is the best thing I brought from the C-suite into the Forest.”

Why a side hustle mindset matters

While George ultimately went all-in on his venture, his approach reflects something many side hustlers overlook - testing before committing.

“A side hustle is a very different thing than diving all-in on a new business. A side hustle can usually have more experimentation. More learning on the job. I like that. Don’t go all-in until you’ve really maximised the probability of success. I kept working at the height of my earning power for the first four years of the faire.”

That measured approach helped him reduce risk while building something entirely new, a lesson that applies whether you’re launching a festival or selling handmade products online.

Lessons for aspiring 'passionpreneurs'

George is candid about the mistakes, too, including one surprisingly common oversight.

“I didn’t pay close enough attention to our early insurance policy. It’s much better now. It’s maddingly boring, but business leaders need to genuinely understand what their insurance will cover and, more importantly, what it will not cover.”

And for anyone dreaming of building their own venture, he recommends learning directly from those already doing it.

“More broadly, interview show-runners and ask them about their key success factors and lessons learned. If you ask 10 of them to speak to you and three say ‘yes’, that’s a win.”

Building a life around what you love

Now 55, George has expanded beyond the festival into other ventures, including a Sherwood Forest summer camp on the same site, where children learn everything from blacksmithing to archery, all wrapped in immersive storytelling.

But his core philosophy hasn’t changed since that one-word calendar entry.

“I get to apply my business skills to the building of the company, but my passion for it hasn't diminished at all – what I love to do most is go to the faire.”

His story is a reminder that a side hustle, or even a full career pivot, doesn’t have to start with a perfect plan.

Sometimes, it starts with a single decision. Stop doing what’s expected and start building something you actually care about.

Image: George Appling performing in the show