The Single Word That Can Cripple Any Online Entrepreneur

Fear is one of the dirtiest words in the English language — and something that every one of us faces.

I’ve been an online entrepreneur for eight years now, and I have said “I am afraid” an infinite amount of times. You’d think that working on the Internet, where it’s easy to hide and take shots without really being known, would lessen the pain.

In 2007, I faced my greatest leap of faith when I left a cushy job as a project manager for an architectural firm to become a freelance web designer.

At the time, I didn’t know that that journey would be full of ups and downs, and that it wouldn’t be the only time I had to make a serious choice.

In this 12-minute episode I discuss:

  •’s definition of the word “fear”
  • The Boston real estate agent who rejected a freelance design
  • How the premium WordPress theme market started
  • When I left my job to go out on my own
  • The fateful phone call from Brian Clark
  • My personal challenge to listeners of No Sidebar

The Show Notes

The Single Word That Can Cripple Any Online Entrepreneur

Brian Gardner: Hey everyone, welcome to the No Sidebar podcast. I’m your host, Brian Gardner, and I’m here help you identify the things that stand in the way of building your online business.

Together we’ll learn how to eliminate the unnecessary, increase conversion, design a better business, and build a more beautiful web.

Last week we talked about the important keeping things real and how that helps set a firm foundation for your digital business.

It’s no secret that many of us struggle with who we are, and that validation is at the very top of our priority list. Social Media and the Internet make it really easy to wear a mask, but that habit can be devastating.

Today I’m going to take things a step further and talk about something that I’m fairly confident we all have to deal with.

Before I go any further, I have a few things to share.

No Sidebar is brought to you by Authority Rainmaker, a carefully designed live educational experience that presents a complete and effective online marketing strategy to help you immediately accelerate your business.

Do not miss the opportunity to see Dan Pink, Sally Hogshead, punk legend Henry Rollins and many other incredible speakers … not to mention the secret sauce of it all: building real world relationships with other attendees. Get all the details right now at And we look forward to seeing you in Denver, Colorado this May. That’s

Here we go.’s Definition of the Word “Fear”

It’s only one word, and in my opinion it’s the dirtiest word of the English language — are you ready for it?


According to, fear is a distressing emotion aroused by impending danger, evil, pain, etc., whether the threat is real or imagined; the feeling or condition of being afraid.

Let’s focus on the last word of that definition — afraid.

As in … I am afraid.

I can’t tell you how many times I’ve said that phrase. To my self. To others. Or to anyone else who would listen.

I said it last year when I was asked to speak in front of 400 people on the same stage that was shared with Seth Godin and Darren Rowse.

I said it in January when I was asked, or shall I say, told, that I’d be doing a podcast that would be listened to by thousands of people.

I think you know where I’m heading with this. Am I right?

I’ve been an online entrepreneur for 8 years now, and I have said “I am afraid” an infinite amount of times.

And you’d think that working on the Internet, where it’s easy to hide and take shots without “really” being known, would lessen the pain.

Um… NOT. I’ve said it, and I’ll say it again.

I am afraid.

Every time I open Photoshop, or get on a call, or hit the record button — I’m continuously obsessing over the idea that what I do, what I say, what I create won’t be good enough or my work won’t be validated.

This is me. Unfiltered. Talking to you — entrepreneur to entrepreneur.

Let’s go back in time to 2007 when I was stuck in a desk job that, while I was competent and enjoyed what I did, didn’t actually fulfill me. Don’t get me wrong, I loved who I worked with, and being around people — but I was bored. Really bored and often questioned what my future looked like.

So I began blogging on WordPress and taught myself how to design and develop themes — which I started off giving away for free.

At Copyblogger we would call this offering “things of value” to my audience — which at the time I didn’t even know what that meant. Little did I know that I was laying the groundwork to my entrepreneurial journey.

Alongside the themes that I was allowing folks to download, I started blogging about the process, which ironically, we call content marketing.

Content what? Yeah — that. I was a newbie at this business thing, and I didn’t have access to all of the wonderful resources that we make freely available over at Copyblogger.

Fast forward a few months and I was still in my day job, making a few hundred dollars here and there doing freelance design work for folks who were using my themes.

Life was good right? I mean we all aspire to moonlight in a job that we desperately want to leave, but can’t — right?

The Boston Real Estate Agent Who Rejected a Freelance Design

Well next comes my favorite part of my story — the real estate agent whose rejection changed my life. A guy from Boston who, one day, I vowed to send on an all-expense paid trip to the Caribbean for being “that guy” who made this entire thing possible.

I designed a custom WordPress theme for him. One that I thought was absolutely stellar, and that he would come back with rave reviews. One that I thought he’d love and together we’d ride off into the sunset.

He hated it. Well, that’s a little strong — but in reality it was not at all what he wanted. He wanted simple, and I built complex. So I threw the design on the cutting room floor and gave him what he wanted.

I was devastated because I thought my work was great. But all I was left with what a couple of files, $500 from him for the simple work and a bruised ego.

How the Premium WordPress Theme Market Started

So I did what all “I have no idea what I’m doing in the business world” people do — I went to my blog and asked the audience how much they would pay for a premium WordPress theme.

You heard me right. Premium WordPress Theme.

I was inundated and overwhelmed with the responses that I got in the comments of that life-altering blog post. In the business world, I learned that this is what they call … “demand,” and I had an opportunity to supply.

When I Left My Job to Go Out on My Own

As a result of this cray-cray outpour of “me want” that I received, I figured I’d slap up a website where people could purchase this theme.

Month 1 — $10,000
Month 2 — $20,000
Month 3 — $40,000
Month 4 — $80,000

Those aren’t cumulative numbers, my friends — that was per month.

At one point, I’m pretty sure I had a conversation with my wife Shelly that went something like … “Uh, I think it’s financially irresponsible for me to stay at my job and think I should do this full time.”

And the worst thing happened to me after I said that. She agreed.

This meant I was faced with one of the biggest decisions of my life. One that impacted me. One that impacted her. And one that impacted my 3 year old.

I was afraid.

I had a full time job. I had insurance. I had a 401K plan. I had guaranteed vacation time. I had security.

But I also had limitations — financially and creatively.

There were barriers that were practically untouchable and the things I wanted to do and places I wanted to go would have been infinitely placed on hold if I decided to stay in my comfort zone.

But there was something exciting about the idea of working online. Something exhilarating about being one of “those people” who were lucky enough to bring a laptop to Starbucks and stay there all day to work.

I knew deep in my heart this was a no-brainer decision and one that I’d more than likely never regret. But … I was afraid.

Afraid that I’d make the wrong call, that things would collapse and that I’d bring my family down along the way.

The voices in my head got louder. The skepticism haunted me and continually grew deeper. In my heart, I wanted to jump and not look back.

So I did. Jump, that is.

And you know what? I haven’t looked back.

It was my instinct that I followed back then, and one that didn’t let me down. In fact, 3 years after making the leap, this company that I started was doing seven figures a year. You may have heard of it. We call it StudioPress.

In 2010 I was living the dream. We had just moved into a really nice house — one I thought we’d never be able to afford. We were taking vacations to places I’d never thought I’d visit. Shelly was a stay-at-home-mom, and things were stable — and safe. I thought to myself, “Ok — now this is nice.”

The Phone Call and Proposition from Brian Clark

But then I learned a lesson in life — that fear always has a way of coming back. Sometimes it’s in the form of another experience or opportunity. And this time it came at me in the form of a call from Brian Clark.

Yes, “the” Brian Clark from Copyblogger. He was a competitor of mine in the premium WordPress space, and had a legal background — which always freaked me out. Like I was doing something wrong — you know, in a “I have no idea what the heck I’m doing” kinda way — and that he’d find something to sue over.

Fortunately this wasn’t the case. The gig he had going wasn’t — well — going well and he wanted to see if I had any interest in partnering up with him to sell themes.

After getting over the “OMG he’s an Internet celebrity” thing, I think I coherently muttered the words “yes, absolutely” to him.

The idea of it all sounded great on the surface — but then reality sunk in and I realized that he was asking me to change what I had going at the time.

I was my own boss, I was making my own decisions — I was the captain of my own boat. The one that I built and the one whose direction I dictated.

He was asking me to give up full ownership of StudioPress — my baby. The thing I created and the thing that was dear to my heart — something I was so incredibly proud of.

And before we officially worked out a deal, he threw another curve ball at me. He asked if I wanted to take it a step further and merge StudioPress into a bigger company.

Typically the words “Hey, I’m heading to Colorado to meet with 4 people who I’ve never met and putting the multimillion dollar thing we have going right now at risk” isn’t received well by a wife, but she trusted my instinct.

So an hour after “Hey, I’m Brian — the StudioPress guy, nice to meet you guys,” we practically had an operating agreement written.

This hodgepodge we created back then is now called Copyblogger Media.

The company that employs and puts food on the table for close to 50 families. The one that’s now doing close to eight figures in annual revenue. The one that recently launched an entire digital marketing podcast network.

And the one that is putting on a conference for 800 people in “the” Ellie Caulkins Opera House in Denver, Colorado this May.

We have so much responsibility. We have so much risk. But with that risk, comes reward. And the reward is often extremely sweet.

None of this would have been possible had I succumbed to my fears — back in 2007, and back in 2010. And I’m sure at some point in the year two thousand and something there’ll be another decision to make.

I’m not perfect, and I’m the first person to admit there was a degree of luck that happened to me along the way.

But what I can say with certainty is that I would have definitely missed out on some great opportunities, missed out on developing some great relationships, and missed out on the opportunity to share all of this with you on a podcast network we built if those words … I am afraid … crippled me.

Who knows, maybe I’d be living a “sort of” comfortable life working as a project manager in a cubicle. Maybe we’d be happy with an “ok” life and enjoy the “safety” of it all.

Or maybe I’d be enjoying a life of fulfillment. One that brought me joy every day, and one that presented fun challenges to overcome and one that I cannot stop loving.

Right now I am writing out the script of this podcast episode while listening to music and sitting at Starbucks.

Guess which road I went down?

The one where I overcame my fear. And as Robert Frost says, “the one less traveled by.” And my friends, I mean this with all that I know — that has made all the difference.

Fear is a sidebar in our life. It’s something that gets in the way of doing what we want, of building what we want and enjoying what we want.

It’s something that haunts us. It’s something that leaves us with difficult decisions.

This is my story and thank you for listening.

My Personal Challenge to the Podcast Listeners

I challenge every one of you to identify what’s blocking your success. So say it with me friends…

No fear. No sidebar.

If you like what you’re hearing on the podcast, the best way to support the show is to leave a rating and/or comment over on iTunes.

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Each week my friend Allison Vesterfelt and I curate the very best and most interesting articles when it comes to designing a simple life — at work, at home and in the soul. Seriously, do it.

Until next week, this has been Brian Gardner.