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In this monthly column, Brian Gardner explores the challenges of operating a WordPress-based business and shares insight into servicing and refueling the human soul.

A few summers ago, our family road tripped to Waco, Texas, to cross an item off our Bucket List. We are huge Fixer Upper fans (Chip and Jo!) and had dreamt of visiting Magnolia Market.

As we were driving through Checotah, Oklahoma, my wife shouted, “Oh my goodness, we’re driving through the town that Carrie Underwood grew up in.”

I questioned how she knew such a random thing, but something about Checotah sounded familiar. Then, a few minutes later, it hit me. I had heard that name before. The last song on Carrie’s debut album is called “I Ain’t in Checotah Anymore.” 

According to the US Census Bureau, a mere 3,142 folks claimed the 74426 zip code of Checotah, Oklahoma, as their hometown. And directly from Carrie’s mouth, it is a small town:

Where sixty-nine meets forty

There’s a single-stoplight town

And back when I was really young

A part of that burned down.

You might be wondering, “Why does any of this matter?”

At age 21, Carrie left everything behind and auditioned in St. Louis, Missouri, for American Idol. She became a contestant, and five rounds into her season, she sang “Alone” by Heart, to which then-judge and producer of the show Simon Cowell said:

“Carrie, you’re not just the girl to beat. You’re the person to beat. I will make a prediction: Not only will you win this show, you will sell more records than any other previous Idol winner.”

Not only did Carrie Underwood win Season 4 of American Idol, she also has sold more than any previous contestant—with over 65 million records globally.

A small-town girl from Checotah, Oklahoma, risking it all.

Life Lessons About Courage

We are all faced with moments in our lives where we can either leave the comfort we’ve always known to start something new or stay where we are. These decisions are never easy, and there is no guarantee they will lead to seven Grammys. 

I often look back at my journey and wonder how things would have gone had I not left my job as a project manager at an architectural firm.

I also wonder what would have happened had I not asked my blog audience to consider buying a WordPress theme. 

Lucky for me, the theme sold, and I started a revolution that created a market that likely has generated hundreds of millions of dollars in revenue.

Over the last fifteen years, I have learned a lot about courage and taking risks in business. Of course, things didn’t always come easy, but I learned a few significant lessons that I want to share.

1. Follow your intuition because it often is right.

“Hindsight is 20/20,” they say, and in my experience, this has been true many times. Looking back at a trivial yet monumental decision illustrates how accurate this is.

When I first started blogging, I was using a free Blogger account. It seemed to be all I was looking for in a publishing platform, but then a friend suggested that I look into WordPress. He walked me through the tedious process of setting it up.

Huh? I asked myself. Why would I want to switch off of something that was working for something that requires a lot of effort to get started?

He told me it was worth the time to look into and owning my content was better long-term—that WordPress would ultimately provide me with more options for publishing my content and creating a design I love.

After a few hours of research, I took his advice. It was a decision that proved pivotal in my entrepreneurial journey just a few months later.

It would have been easier to stay with Blogger because I felt comfortable with the process and how things worked. But, on the other hand, I knew that I was settling out of safety and was limiting my potential online.

My gut told me to step outside my comfort zone, roll up my sleeves, and get my hands dirty. When I followed my instinct, I learned a lesson in being self-employed: The greater the risk, the greater the reward.

2. Know when to hold them, know when to fold them.

The legendary Kenny Rogers once sang:

“You got to know when to hold ’em, know when to fold ’em,

Know when to walk away and know when to run.”

Two years into owning a business, I received an email that upended everything. It was a cease and desist letter, which requested that I rename my product (Revolution WordPress theme) because it was causing confusion in the marketplace and infringing on their trademark.

I cried that night because I thought everything was over. The job and security I had left to pursue this dream could be coming to an end, and I didn’t know what to do.

I Googled “What to do with a cease and desist letter?” and was overwhelmed with the various suggestions that I found. Anywhere from ignoring it to contacting an IP lawyer. A what? I asked myself.

I discovered that IP meant “Intellectual Property,” which is “a work or invention that is the result of creativity, such as a manuscript or a design, to which one has rights and for which one may apply for a patent, copyright, trademark.”

So I did that. I emailed a local IP lawyer that evening and called the following day. The tl;dr of that conversation was this: Don’t worry, rebrand your product, email them back, apologize, and share with them that you have taken steps to do just that—all under a different name.

My first instinct when receiving that letter was to “fold ’em.” That evening, I was so scared that I almost shut down the website entirely, out of fear that the FBI was on their way and that within hours I’d be hauled off to prison. That wasn’t the case, as much as I had convinced myself it was a real possibility.

But I chose to “hold ’em” and let things play out. So I rebranded to StudioPress, and fifteen years later, things are still going strong—and I never served time.

3. When the reward outweighs the risk, hit the “go” button.

Back in 2006, when I decided to sell WordPress themes, I didn’t understand what “open-source software” was. At the time, I was making thousands of dollars a day and thought I was “protecting my work” with the proprietary license I had implemented.

After witnessing many discussions within the WordPress community, I quickly learned what open-source was—and what open-source wasn’t.

According to Wikipedia, here’s the definition:

Open-source software is computer software whose source code is available under a license. The copyright holder grants users the rights to study, change, and distribute the software to anyone and for any purpose.

The way I was conducting my business was not in alignment, and I was conflicted about whether or not I should do anything about it. After all, my business was doing quite well, and I had already weathered the cease and desist letter and subsequent rebranding.

I asked myself, Do I have the courage to make another colossal change and risk (again) things falling apart?

My livelihood was at stake, and my premium theme business was the only source of revenue that my family had. But, everything changed the moment I saw this comment left by Matt Mullenweg, co-founder of WordPress:

“There are many ways you can make money without violating the letter or spirit of WordPress’ GPL license, in fact, a lot more than just peddling code. It’s disappointing that so many otherwise-talented designers focus on the short-term, not unlike the sponsored links era. I’m happy to give significant promotion to theme designers who stop fighting the license of the platform which enabled their market to exist in the first place, email me.”

While I admit I have no formal education in business, I felt this was an opportunity to take the next step. And I knew it was the right thing to do.

A few days later, I booked a flight to San Francisco to meet with Matt and then-CEO of Automattic, Toni Schneider, to discuss my decision to change the licensing to open-source.

Guess what? I changed it, and the rest—as they say—is history.

High Fives Everywhere

“I can’t believe this is happening to me. The weirdest thing is that it was just a dream, and now it’s real. It’s hard to believe sometimes.” —Carrie Underwood

Some days I feel as though it was pure happenstance—that it was merely a stroke of luck and I was in the right place at the right time. Other days, I embraced that I was smart enough to seize the opportunity presented in front of me.

I never set out to build a business that would one day be acquired. It’s been fifteen years since I took the leap of faith, and while things haven’t always been easy, I have no regrets about the decisions I have made.

Life often throws us curveballs, which is something we should all expect. I know that I have had my fair share of them, and I assure you that I will see some more. But I’ve learned that having the courage to risk it all can sometimes be the difference between a strikeout and a home run.

So when that happens to you—personally or professionally—I encourage you to step up to the plate, wait for the pitch, and swing with all of your might. And when you do, I’ll be waiting for you at home plate as you round the bases. With high fives everywhere, as the fans go wild.

The Giants Win the Pennant! The Giants Win the Pennant!

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