Last week, our family road tripped to Texas, so that we could cross an item off our Bucket List. My wife and I are huge Fixer Upper fans, and have dreamt of spending time (eh, money) at Magnolia Market. So we did. (Both road trip, and spend lots of money.)
On our way down there, we had the pleasure of driving through Oklahoma—a first for my wife, as I had been to Oklahoma City for a conference.
One part of Oklahoma I had never been to was a small town named Checotah, which more than likely a tiny percentage of the world (myself included) has/had never knew existed. My wife, however, had, and she made that known as we approached it.
“Oh my goodness, we’re going to be driving through the small town that Carrie Underwood grew up in.”
Then it hit me. I had heard that name before. The very last song on Carrie’s debut album is called “I Ain’t in Checotah Anymore.” Well in that very moment—and it wasn’t for long— we were in Checotah.
According to the US Census Bureau in 2010, a mere 3,335 folks claimed the 74426 zip code of Checotah, Oklahoma as their hometown. And from Carrie’s mouth, it is quite small:
“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?”
Well, not only did Carrie Underwood win Season 4 of American Idol, she is sitting at the top of the list for contestants who have sold the most albums in the United States—with nearly 17 million.
Think about that. A small town girl, 21 at the time, left everything behind and auditioned in St. Louis, Missouri with Bonnie Raitt’s “I Can’t Make You Love Me.” After her audition, then-judge and producer of the show, Simon Cowell said:
“I think you’re very good. I think you should stay good at what you’re doing as well.”
The “what you’re doing” was about her singing country music—something Simon admits he, in general, wasn’t a huge fan of. Five rounds into her season, Carrie sang “Alone” by Heart, to which Simon said this afterward:
“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.”
A small town girl, from Checotah, Oklahoma.
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 wonder what would have happened had I not asked my audience if they would buy a WordPress theme.
Because when I did, I created the premium theme market within WordPress, which has likely generated more than a hundred million dollars of sales for those of us who sell them.
Over the last eleven years, I have learned many lessons about courage and risk in entrepreneurship. They didn’t always come easy, but they are things that I want to pass along to you.
1. Follow your intuition, because sometimes it just might be right.
“Hindsight is 20/20,” they say, and in my entrepreneurial experience, this has been true many times. Looking back at a trivial, yet monumental, decision illustrates just how much this is accurate.
When I first started blogging, I was using a free Blogger account. It was great, without any problem, and seemed to be all that I was looking for in a publishing platform. Months into my first blog, a friend recommended that I look into this thing called WordPress, and explain in grave detail, how the installation process went.
Huh? I said. Why would I want to switch off of something that was working for something that required what seemed to be a long, gratuitous process?
He told me it was worth the time to look into, that owning my content was better longterm, and that WordPress would ultimately provide me with many more options for publishing and customizing content.
After a few hours of research, I decided that heeding his advice was a smart move—one that would prove pivotal in my entrepreneurial journey just a few short months later.
It would have been much easier to stay with Blogger because I felt comfortable with the process and how things worked. On the other hand, I knew that I was settling out of safety, and was probably limiting what I could be doing online.
My gut told me to step outside my comfort zone, roll up my sleeves, and quite frankly, get dirty. When I followed my instinct, I learned a fundamental lesson in working for yourself: 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 my venture of freelancing and internet shenanigans, I received an email that changed the direction my entrepreneurial world was heading.
It was a cease and desist letter, which kindly requested that I rename my product (Revolution WordPress theme) because it was causing confusion in the marketplace and infringing on their trademark.
I panicked, quite extensively.
I cried the night I received it 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 when you’re sent a cease and desist letter?” and was overwhelmed with the variety of suggestions that I found. Anywhere from ignoring it, to contacting an IP lawyer. A what? I asked myself.
Thanks to Google (again), I discovered that IP meant “Intellectual Property,” which after Googling a third time, learned that it meant “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 set up a call the following day to discuss my situation. The tl;dr of that conversation was this: Don’t worry, rebrand your product, email them back, apologizing and sharing with them that you have taken steps to do just that—rebrand the product under a different name.
My first instinct when receiving that letter was to “fold ’em.” That evening, I was so freaked out 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.
I chose to “hold ’em,” and let things play out. They did, and nine years later, the StudioPress brand is stronger than ever—and I never served time.
3. When the benefits outweigh the risk, pull the trigger.
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 selling themes, and thought I was “protecting my work” by the proprietary license I had implemented. Because that’s what creators do, am I right?
After witnessing many discussions that had been taking place within the WordPress community, I quickly learned what open-source was—and also what open-source wasn’t. According to Wikipedia, here’s the definition:
Open-source software is a type of computer software whose source code is released under a license in which 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. I was on the fence 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.
Did I really have the courage to make another colossal change and risk (again) things falling apart? This was livelihood we’re talking about, and the only source of revenue that my family had.
Everything changed the moment I saw this comment left on a blog by the founder of WordPress, Matt Mullenweg:
“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 are focusing 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, just email me.”
While I admit I have no formal education when it comes to business, I knew this was an opportunity—the opportunity—that could make a difference in the long run. Yes, it meant putting my current method of operation in jeopardy, but I felt like it was the right move.
A few days later, I booked a flight to San Francisco to meet with Matt and the CEO of Automattic, Toni Schneider, to discuss my decision to change the licensing of my software to open-source. Guess what? I changed it, and have never looked back.
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 embrace the fact that I was smart enough to seize the opportunity which presented itself in front of me.
It’s been twelve years since I took the leap of faith and became a creative entrepreneur. I can assure you it hasn’t always been easy, but not a day goes by that I regret my decision—trust me, the risks are worth it.