Boardrooms to Broadswords: How a Passion Became a Real Business | Ep 032
In episode 032, Sam Donaghey and Michael Johnson sit down with George Appling, entrepreneur, author, and Vistage chair, to discuss building a business that aligns with personal passion.
George shares how he transitioned from corporate leadership to launching Sherwood Forest Faire, the lessons he learned about timing, self-awareness, and intentionality, and how he built businesses that thrive without him. He also dives into scalable hiring strategies, business ownership vs. legacy wealth, and why choosing the right path matters.
Tune in for insights on scaling with purpose, building a self-sustaining company, and making business decisions that align with your values.
Listen On:
In This Episode, You’ll Learn:
- Breaking Free from Expectations: How George Appling set a four-year deadline to discover his true passion.
- Vistage and Peer Advisory Groups: How business leaders benefit from structured mentorship and feedback.
- The Journey to Owning a Renaissance Festival: How George transitioned from corporate leadership to building Sherwood Forest Faire.
- Scaling a Seasonal Business: The challenges of continuous investment, staffing, and long-term growth.
- Turning Passion into Profit: How strategic vertical and horizontal integration strengthened the festival business.
- Finding Your True Calling: A framework with five paths to align passion and work.
- Building a Self-Sustaining Business: The hiring, governance, and leadership strategies that allow businesses to thrive independently.
- Leaving a Legacy Without Handouts: Why George believes in supporting his children through education and opportunity rather than inheritance.
- Therapeutic Horsemanship for Veterans: How working with horses helps veterans and first responders manage stress.
- Staying True to Your Values in Business: Why building a business you love leads to long-term success.
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Transcript
George Appling
So when I was 36 years old, I put a note in my calendar. I don’t know if you guys remember, we used to have BlackBerries that were on our belts like holsters, and we thought we were cool, like we had a little pistol on our belt. So I had a little BlackBerry with the thumb board, and on my 40th birthday, I put in a note that said “STOP” in all capital letters. And what that meant was stop doing what the economy expected me to do and do what I deeply, genuinely was passionate about. And I didn’t know what that meant, right? I didn’t really know at 36 years old what I was deeply, genuinely passionate about, so I gave myself four years to figure it out.
Sam Donaghey
This podcast is brought to you by Fast Slow Motion, a team of expert consultants that have helped thousands of growing businesses build scalable systems on the Salesforce and HubSpot platforms. To learn more, visit fastslowmotion.com. Welcome to the Fast Slow Motion podcast, where we teach you how to build a business you love while enjoying your life.
I’m your host, Sam Donaghey, and today I’m joined by George Appling, an entrepreneur, author, and mentor to other business leaders, as well as Michael Johnson, Director of Growth here at Fast Slow Motion. George, Michael, it’s great to see you both today, and thanks for joining us.
George Appling
Glad to be here, Sam.
Sam Donaghey
So, George, you’ve got a super fascinating story. You know, it’s about your journey from the corporate world to where you are today as an entrepreneur. But before we get into that, I wanted to talk for a moment about how you and Michael connected. And I’m really glad that Michael could join us for this conversation today, since you guys know each other through an organization called Vistage.
Now, Vistage provides a lot of value for business leaders, and it’s really something that our listeners should hear about. So, Michael, first of all, can you tell us about what Vistage actually is?
Michael Johnson
Vistage is a fantastic organization that provides something that’s really rare for owners, key leaders, and founders, and that is peer group input. Vistage puts you in groups with your peers and with a chair, where you meet regularly, share problems, work through issues, and learn from each other. I think everybody knows that the more successful you are, the further you get up in an organization, the amount of feedback you get diminishes—unless you’re really intentional about it.
Vistage is a fantastic organization that enables leaders, key leaders, and founders to get that feedback, share, learn, and grow together, and it produces fantastic results.
Sam Donaghey
And George, you’re basically what Vistage calls a chair, right? So what exactly do you do in that role?
George Appling
So the chair is the person who just pulls the group together. I have a one-on-one coaching call with each member every month, and I’ve got 12 members. So imagine there’s a week each month where I’m just doing these back-to-back one-on-one coaching calls. And then I organize the Vistage Day, which is a full day once a month where we’re all in a room together.
So imagine there are 12 small-to-medium business local CEOs in a room, and we’re all trying to help each other solve problems. It’s pretty extraordinary. And the organization’s big and old—it’s more than 65 years old. We have over 40,000 members worldwide. Yeah, it’s quite a proven model.
Michael Johnson
Yeah, it’s a fantastic organization, George. I’ve really seen the impact that chairs like you have had in the lives of business owners and leaders. I really appreciate the journey that you’ve taken a lot of us on. So thank you for what you do.
Sam Donaghey
So, George, you left a prestigious CEO role to pursue your passion. Can you tell us more about that? What inspired you to make such a bold move?
George Appling
So when I was 36 years old, I put a note in my calendar. I don’t know if you guys remember, we used to have BlackBerries that were on our belts like holsters, and we thought we were cool, like we had a little pistol on our belt. I had a BlackBerry with the thumb board, and on my 40th birthday, I put in a note that said “STOP” in all capital letters. And what that meant was stop doing what the economy expected me to do and do what I deeply, genuinely was passionate about. And I didn’t know what that meant, right? I didn’t really know at 36 years old what I was deeply, genuinely passionate about, so I gave myself four years to figure it out.
And then, it was only one year later when a friend of mine said the Texas Renaissance Festival was for sale. And that was that moment when the clouds parted, the angels sang, and the lightning bolt struck. That was it. I knew that the Renaissance Festival was the only thing I’d loved my entire life, other than my mother. I’d even had a 38-year streak—I came back to that show no matter where I lived.
That’s the one outside of Houston, Texas. Having lived in Boston for three years, Germany for three years, England for a year, Australia for a year, and Russia for a year, I always came back to maintain my streak at the Texas Renaissance Festival. But it had never really occurred to me that it was a business until that moment when she said it was for sale.
And so I started thinking—yeah, somebody owns that. Then I started thinking about the math and the P&L, and I realized, wait, someone might make a lot of money doing that. So then I took a run at buying the Texas Renaissance Festival, which didn’t work. I took a run at buying the one in Dallas, which got very close—it got within one day of closing, and that fell apart. So then, I co-founded Sherwood Forest Faire, which is the Renaissance Festival for Austin.
Sam Donaghey
So that wasn’t actually a business already in place. That was something that you set up from the ground up?
George Appling
That’s right. Yeah. We started it from the beginning, and we opened our doors for the first time in February of 2010.
And you can imagine it’s a theme park, right? With back then over a hundred buildings, and now there’s over 200 buildings. And I had no idea if 30 people would come through the gate or 300 or 3,000 or 10,000. I’m sweating bullets. And 3,000 people showed up. And I thought, okay, I think we’re going to be fine.
And now we average 10,000 people per day.
Sam Donaghey
Wow. So you average 10,000 people per day? Oh my goodness. So, what kind of unique challenges come with running a renaissance faire that might differ from a traditional business, would you say?
George Appling
A couple of things. One is there’s always an enormous amount of investment—building bars, building stages, underground electricity, flushing toilets, underground plumbing, more parking. And, you know, we’re in this forever, right? This isn’t your tech startup that you’re building to sell and get rich. This is a forever business. My plan is that when they pull the plug on me in hospice, my final words will be, “The show must go on.”
And so, it’s constantly investing but taking it easy, right? It’s a marathon, not a sprint. That’s one of the things that we say in this business a lot—continuous investment. Other than that, you know, there are a lot of seasonal employees. We’re only open on Saturdays and Sundays in March and April for the faire. Then we have a summer camp in July and a Celtic music festival in December. But, you know, there’s a lot of people coming and going. Maintaining a really wonderful culture of people who work there is a challenge, but it’s something we’ve known since the beginning, so we put a lot of energy into it.
Sam Donaghey
That’s incredible. I did see some of the things that you do there as well, like the artisans and the crafts. One thing stood out in particular—I think it was Thorin’s Viking Mead that caught my eye. How’s that going?
George Appling
Amazing. Actually, Thorne is my cousin, and I think he’s the number one selling mead in Texas now.
And that’s actually a funny story. During the opening season of Sherwood Forest Faire in 2010, he walks up to me and says, “You know, George, I make mead, and it’s better than all the other meads.” And he had this black overcoat—he opens it up, and there are bottles on the inside liner, like a drug dealer. He says, “You should try my mead.”
And I’m just humoring him, like, fine, he’s my cousin, I’ll drink his moonshine. So we sit down, and I’ve been a renaissance festival nerd for decades at this point—I’ve had all the meads. So I try his mead, and I say, “That is better than all the other meads. What’s going on here?”
And he says, “Well, my family’s been making this for generations. It’s kind of what we do.”
And I said, “Okay, well, then we should figure out how to sell it here next year.” And he goes, “Well, that’s the problem. I don’t know how to do things legally. I keep getting arrested.” It’s like, you can’t just sell mead out of the back of your truck—it’s illegal. But that’s what he would do.
And I said, “Okay, well, I know how to do that. I know how to do business legally.” So then we set up some legal entities, and now we’re business partners. And it’s going extremely well.
Michael Johnson
Yeah, that’s an incredible story because, George, you started something you’re passionate about and created essentially a captive audience. Now he’s got this product-market fit that he may not have had before. He’s got a market to go to that’s easily accessible for him, and you guys can succeed together. So that’s really fantastic.
George Appling
From a business strategy point of view, there’s this concept of vertical integration and horizontal integration. The national mead market is a majority at renaissance festivals, right? It didn’t take long to realize that being in the mead business means two bites at the apple. That really worked—that’s vertical integration.
And then, horizontally, I own the land. We’re only open for eight weekends in the spring, so I thought, well, we have to do something else. That’s where we created the summer camp, the music festival, and the site rental for live-action role-play. I’m completely in love with my businesses, but the old strategist from years ago is still there, trying to make good decisions for everybody.
Sam Donaghey
Well, I suppose we could segue from that into any advice you could give to our listeners. A lot of people talk about wanting to start a business, but they have trouble choosing what to focus on. It sounds like—I don’t want to put words in your mouth—but it sounds like your journey unfolded naturally. You got opportunities, grabbed them, and they grew organically.
But how would somebody identify their true calling if they were starting out? Do you have any advice for them?
George Appling
Yeah. Last month, I published a book on this topic called Don’t Settle. The book is a framework through which the reader can choose the relationship between their passion and their work. But that’s not to say your passion and your work should be the same thing. That’s just one of the five paths. This framework leads you down a path of making a choice between these five paths.
One is passion now, right? That makes sense if you know what your passion is and you know you can monetize it and you know you can make enough relative to your need for financial security. Those are some pretty tight conditions, right? So there’s passion now, there’s independence, which is where your passion and your work don’t have anything to do with each other. And that’s okay if that’s your choice, right? You will be much more comfortable and content with that choice if you made it.
As opposed to the economy making it for you, there’s the experiment path, which is kind of hovering around learning. And that’s particularly for people who don’t know what their passion is. There’s the money path. And we all know people on the money path where it’s passion-smashing—I’ve got to be rich. And then maybe after they’re rich, they can think about passion later.
And then there’s the balance path, which is what I did. And it’s, I know I want to marry my work and my passion, but not yet. I want to have financial security. I want to have capabilities. I want to see the world. I want to have a reputation. I want to get ready to switch over to the passion path several years down—10, 15 years later—so that my probability of success is higher.
So, I really believe in this framework for choosing the relationship between your passion and work, and it can always end up with your passion and work being the same, but it doesn’t necessarily mean now.
Michael Johnson
Yeah, I think your book is super well-timed, George, because I saw a stat recently that said that for Gen Z, between 60 to 75 percent—depending on where you look—really value impact and passion in their work. That’s what they’re looking for. Whereas I think in generations before, that wasn’t as high of a percentage.
And so your book is really well-timed, and I’m just wondering, do you have any advice for entrepreneurs or business owners that are maybe looking to start additional businesses or diversify the businesses they own? What advice could you give listeners to really help them along that path?
George Appling
I’ll give you two very specific pieces of advice. One is don’t trust your own assessment of your own capabilities. People are pretty bad at assessing their own capabilities, right? Something like 80 percent of all humans think they’re smarter than average.
You need to test your capabilities before starting a business, but don’t rely on yourself. Go talk to other people—former professors, trusted mentors, family members—and give them explicit permission to be hard on you and tell you where your gaps and weaknesses are.
Because people will fool themselves into thinking they’re ready before they are. And when you find gaps, be open to that feedback and think through how to close them.
Guidance number two is, I’m a big believer in writing down a formal business plan. And I mean really—like a 20-page presentation on your business plan.
The reason is that it forces you to think holistically. It forces you to think about what problem you’re solving. Who are you solving it for? How are you going to tell them that you’ve got their problem solved? What’s the five-year financial outlook, the total addressable market? How much can you get? What does the P&L look like?
And really writing all of that down just forces you to think holistically. I’ll add a couple of things in there that business plan templates don’t have.
One is timing. It turns out timing is the most important correlated variable to startup success. And there’s not a page in the business plan template that says the time is right. So you’ve got to create that yourself.
The second is there’s no template in the business plan for failed analogs—companies that tried to do something similar to what you’re trying to do, but it didn’t work. So study failure and create that page in your business plan.
I’ll give you a quick example on each one of those.
On studying failure—when I decided to get into the Renaissance Festival business, I went and found 75 Renaissance Festivals that had failed. And I scored them based on the reason they failed. The large majority had one thing in common—the landowner and the business owner were different people.
And so you can imagine, as the business starts to grow, the landowner just raises the rent. Or, as it seems to happen in this world, the landowner wants to have his own bar—because everybody wants to own a bar. And so then they end up having this fundamental disconnect, and it falls apart.
So when it came to getting into Sherwood, I insisted on owning half the land. I had a business partner—we were 50/50. And that was a big drama because he had bought the land with a silent partner. And I insisted on buying them out.
To be his business partner, I had to buy them out. And he ended up sacrificing a 15-year friendship to force them to sell to me. But I wasn’t going to give up on the number one reason that these businesses fail. I’m convinced that was the right thing to do, and I think my co-founder would say the same.
On the timing thing—there’s this great TED Talk. I forget the guy’s name, but he’s a Silicon Valley venture capitalist. And he took 100 companies that he had funded and 100 companies that other people had funded. He scored them on success—state equity value at exit—and he just scored all the variables he could think of to find correlations to startup success.
He found the high correlations were the quality of the business plan, the technology, the team, the funding, and the timing. And it turned out the timing had the highest correlation.
But you’ve never seen a business plan template where there’s a slide that says, “Why is the timing right?” Right? So you’ve got to do that yourself.
I just went off on a tirade there—I need to calm down.
Michael Johnson
Just to follow up there—do you think it’s more important to do some of this work? You talked about a combination of self-reflection and essentially market analysis, writing a business plan, looking at what’s out there.
Is it important to do that before and wait for the right time? Or do you recognize the time first and then do some of that hard work?
George Appling
You come up with a business that you want to build because you love it. Hopefully, you’re also good at it. Hopefully, you’re solving a problem that needs to be solved, or you’re solving a problem better than it’s currently being solved.
That’s kind of the beginning. And then when you’re writing the business plan, you have to ask yourself in a very tough-minded way—is the market ready for this solution?
And I think it is. So timing is not the first thought. The business idea is the first thought. And then you’ve got to answer the timing question.
Michael Johnson
Love that. I think I know the answer to this, but it seems like self-awareness is really, really critical to starting a successful business or building a business that you love. Could you talk a little bit more about self-awareness? And maybe if someone doesn’t have a high sense of self-awareness, how they could get it?
George Appling
Yeah. So when I think about self-awareness, I’m a huge believer in the power of intentionality. And I hinted at this earlier, saying even if your passion and your work don’t have anything to do with each other, if you’ve gone through a structured thinking process and made that decision, you’re going to be happier with it.
You’re going to be more productive. You’re going to be more content. I’m a big believer in intentionality. I’m a big believer in agency. So I think when you talk to mental health practitioners, they’ll often say the first hurdle with a patient is agency—it’s convincing them that they can take steps and make their lives better.
When I give my book talk at universities, I end with this page that says: “1.0 raised to the 365″—the metaphor being one step a day, every day. 1.0 raised to the 365 is 1.0. But 1.01 raised to the 365? It’s 37, right? So if you can take one more step each day, you will make your life better every day.
So I’m just a huge believer in agency and intentionality. And you’ve got to be self-aware to do that. The way to become self-aware is to be intentional and to accept your own agency.
Michael Johnson
You own several businesses. You’ve got a lot of entrepreneurship experience. What do you enjoy most about your businesses today?
George Appling
I think I enjoy not having a boss. That’s pretty good. I’ll tell you what I’m really happy about now. I was doing an interview last year, and the interviewer said, “George, you’ve got eight companies. If you got hit by a bus and died on the way home, how many of them would survive?”
And I said, “All eight.”
And he said, “There’s no way that’s true.”
I’m like, “I promise you, none of them would miss a single beat. None of them would have a revenue decrease. They would all keep doing exactly what they’re doing because they don’t actually need me.”
So I spent a lot of time getting the right people in seats, getting the right values in place, and putting the right decision structures in place so that my companies don’t actually need me.
Which segues into—what do I enjoy? I enjoy being able to engage in what I want to engage in. Now, I’m engaging in these big opportunities. Like today, I’ll be signing a deal to spend $60,000 buying ten golf carts. Well, it turns out we pay $50,000 a year to rent golf carts. Okay, so that’s an easy one, right?
And I’ve pulled the trigger on a million-dollar solar farm. The government is paying for most of it, and it’s going to take away my $70,000-a-year power bill. So I’m excited to work on big things like that.
Sam Donaghey
I love that. And just while we’re on the topic, because you mentioned something about getting the right people on the bus—this is a topic that I’m fond of. I’m the recruitment director at Fast Slow Motion.
What’s your approach to building teams and finding the right people who can help you manage your various ventures?
George Appling
I spend a lot of time on this with my coaching clients in Vistage. And I’ve got this belief that small business owners underinvest in interviewing.
So I spend a lot of time helping my members—and, of course, I do this in my own business—helping them interview in very intentional and structured ways. What I typically do is take the position you’re trying to hire for and come up with the five qualities that you need in that person.
It might be that you need a self-starter. It might be that you need expertise in a certain thing. It might be that you need them to have a certain network. Whatever it is, here are the five things that you need.
Then, we come up with either a formal test or a couple of insightful questions that get at whether they have that quality.
For your interviews, you end up with this 10-question interview guide that really digs into the qualities you need for the role. So the first thing I’d say is—overinvest in interviewing.
Michael Johnson
That works. That’s amazing. And George, once you get the right people in the right seat—what is your process, or what are some of the things you do to empower them to do what you’ve said, which is run the business without you? Essentially, have it run where you can step away? What are some of the things you do internally to get them to that point?
George Appling
Yeah. So we’ve got a pretty normal or standard governance model where we’ll have a quarterly business review once every three months. The whole—what I call Team One—it’s sort of Patrick Lencioni’s Team One or First Team idea—we’ll get together for several hours in a room and just go through everything.
And so that ensures that the eight people who report to me are all on the same page. And we only have to do that once every three months. Then we’ll have a bigger meeting once a year to prioritize the investments, right? Because we’ll invest hundreds of thousands of dollars every year, and so we have a structured analytical exercise to choose what we’re going to invest in.
And then there’s this kind of standard governance thing where I talk to most of my key directors for 15 minutes every week. So in the span of about 45 minutes, I talk to my site director for 15 minutes, then my entertainment director for 15 minutes, and then my camp director for 15 minutes. It’s always the same three questions:
Did you get done what you wanted to get done last week?
What are you going to get done this week?
How can I help you?
It just works.
Michael Johnson
Yeah, that’s amazing. So you’re able to coach them and focus your time on exactly what they need to make decisions and empower them to do what they do really well.
I love that model. We’ve talked a lot about business strategy—how to build a business and how to let it run. Shifting to something a little more personal, you’ve talked elsewhere about your decision not to leave your kids a cash inheritance. Can you explain the reasoning behind this decision?
George Appling
So, I’m a very serious history nerd. Like, all the books behind me are history books.
And my conclusion, based on all of my reading, is that making your children wealthy is a bad idea. It ends up demotivating them, or at least there’s a very high risk that you’re going to demotivate them and they’re not going to give to the world what they’re capable of giving. You can see examples of that throughout thousands of years of recorded history.
And then if you think through your personal network, you probably know someone who was a millionaire at 18 years old, and it didn’t turn out very well. So, I’m very much in this camp of: when I die, I will leave my wealth in a trust. The trust’s primary mission is to keep the businesses alive—the faire and the camp. But then it will also do some things for descendants. I’ve got money set aside to pay for my kids’ college, and I’ll buy them their first car—it’s not going to be fancy, but it’ll get them to and from places. I’ll also cover the down payment on their first house. So, I’m very much a hand-up guy, not a handout guy.
There are too many cases where making a young person rich carries a high risk of ruining them.
Michael Johnson
I love that—hand up versus handout. How do you think that approach is going to be a foundation or prepare them for success?
George Appling
Well, the good news is my kids have known their entire lives that I’m not going to make them wealthy, right?
So, it’s not a surprise. It’s not weird. It’s not disappointing. It’s just always been there—it’s always been the truth. And I think there are great models for this. The Rockefeller model is kind of what I’m following, and I think that model is supporting something like 1,800 descendants now.
It covers college, a house down payment, and a car. But then the other thing it does—and I’ll put this in my trust—is if they have a business plan that passes muster, the trust might make them a loan to build a business. But they only get that once—unless they pay it back, in which case they can do it again.
It’s not tough love. It’s just being very rational, I think.
Sam Donaghey
George, I’ve seen something as well that you’re involved in, which interests me—you’re the chairman of the board of the Knights of the Grail, and you help military veterans. Can you tell us a bit about that?
George Appling
Yeah, so it’s therapeutic horsemanship.
There’s a famous saying by one of your countrymen, Sam—Winston Churchill said, “There is something about the outside of a horse that is good for the inside of a man.” I’ll add “and woman” on Winston’s behalf. Horses are great for people because they are very empathic.
Your emotions can influence their emotions. Which means, if you want to work with a horse, you have to be very much in control of how you’re feeling. And if you’re not in control, you have to pretend to be in control and convince the horse. It’s very therapeutic.
We’ve got a herd of eight, a world-class trainer, and we have veterans, sometimes active duty and first responders, working with horses almost every weekend of the year.
Sam Donaghey
Fantastic. Well, I’ve got two more questions. How can entrepreneurs stay true to their personal values while building successful businesses?
George Appling
You have to do that. It starts with—what’s the purpose of building the business? I think there’s a massive difference between building a business to sell it and get rich versus building something to run because you love it and plan to run it as long as you can.
Sam Donaghey
Love it. Well, George, we always like to close our podcast episodes with a quote that provides some wisdom or advice for our listeners. Is there a quote you’d like to share with us today?
George Appling
William Marshal, largely considered the greatest knight who ever lived, once said: “Know this, for this is the heart of it—idleness shames a young man.”
Sam Donaghey
Absolutely love it. Well, that’s it for today’s episode. Thanks again to George and Michael for joining us. Remember to subscribe to the podcast on your favorite platform or find archived episodes at fastslowmotion.com/podcast.









