From Solo to CEO: The Evolution of an Entrepreneur

The Transcript

From Solo to CEO: The Evolution of an Entrepreneur

Voiceover: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at RainmakerPlatform.com.

Welcome to Unemployable, a show for people who can get a job, they’re just not inclined to take one — and that’s putting it gently. If you’re a freelancer or a solopreneur, Unemployable is the place to get actionable advice for growing your business, improving your processes, and enjoying greater freedom day to day. To get the full experience, register at no charge at Unemployable.com. You’ll get access to upcoming webinars and more.

Brian Clark: Welcome to Episode 2 of Unemployable. I’m your host, Brian Clark.

Let’s go ahead and dive right into today’s topic. Ultimately, this lesson is about the way you think and how that influences the kind of business that you have. After 17 years and nine businesses, I run the gamut of roles and levels of sophistication outside the traditional world of employment. Been quite a ride to say the least.

When I look back, I can identify four distinct phases that I’ve gone through. One of which may correspond to where you’re at currently or where you want to get to.

Are Freelancers ‘Lesser’ Than Entrepreneurs?

First up, I want to address the distinction that a lot of people are quick to point out — often quite smugly. It’s the idea that freelancers and consultants, maybe even solopreneurs, are not real entrepreneurs. Now, there are definitely distinctions — just as there are different kinds of entrepreneurs, frankly. But some entrepreneurs tend to look down on freelancers and consultants as if they’re some kind of lower life form.

I don’t agree with that.

As far as I’m concerned, if you’re operating without a job, you’re running a business. At minimum, you’re an independent economic actor that supports yourself and your family. That alone deserves respect. Some people stay in the role of freelancer or consultant because that’s what they want to do. What’s wrong with that?

Why ‘Should’ Is a Dirty Word for Unemployable Types

There’s always room to improve things so you’re even happier, but don’t listen to anyone who tells you that you should be doing this or that or something else. ‘Should’ is a dirty word for us unemployable types. You’ll hear that emphasized over and over on this show.

Other people do want to evolve beyond the freelance role, or maybe evolve beyond service businesses in general. The most common thing I hear is the desire to move from clients to selling something else, like products. I get that. I made the same transition.

Let’s take a brief look at my path over the last 17 years. Many of the ideas here will provide the foundation for strategies that we’ll dive in deeper to in the future.

That I Was More Clueless Than You … Guaranteed

Before we can actually talk about the four phases, we have to talk about a pre-phase — which I call ‘clueless.’ This was 1998 when I quit my nice, cushy attorney job in a very well thought of law firm and just dove in head first. Now, keep in mind, I was a liberal arts major with a law degree and four years of experience as an attorney.

Technically, I was not qualified to do anything except practice law. I’d never taken a business course, never read a marketing book — truly clueless. Now, in some ways, that was a blessing, but I wouldn’t advise anyone to just quit and hope to end up on their feet. I operate great under pressure, actually better, but my advice is don’t quit your job until you’re ready to go.

My idea was basically that I wanted to find a way to make a living writing, but I didn’t want to write books. I didn’t want to write screenplays because that meant I had to deal with New York or LA and had to ask permission all over again. Guess what, certain types of people don’t like to ask permission to do anything.

I was looking around online, and I saw people publishing email newsletters. You may be familiar with Chris Pirillo. He’s been around online for a long time. That’s what he was doing, topical email newsletters, and he was selling advertising against those for what seemed to be a lot of money, looking at his rate card. Found out later that what you say you want is not always what you get. But, of course, like I said, I was clueless.

I was successful in building audiences by creating content, a skill and an approach that has served me well the entire time. These days that’s called content marketing, and the world is trying to adapt to that. That’s just what I wanted to do. In many ways, I was lucky in that sense. But I was making zero money. It was very difficult to get advertisers, and I didn’t know what I was doing anyway.

Basically, in 1999, I read my first marketing book. It was a book called, Permission Marketing. Again, this was a blessing that I knew nothing about marketing before because this was very different approach to traditional marketing, I should say. Basically, the first book I ever read was perfect for online marketing, which is what I’ve been doing the entire time.

Essentially, the mind-shift there was, “I need something to sell.” The Internet is a direct medium. You’re establishing a direct relationship with people through your content delivered by email. If you have something to sell, then you can make money.

First phase, ‘solo,’ 1999-2002. I was, technically, a solo practitioner, which is what they call attorneys who are on their own. It’s a freelance job, really — what’s the difference? You have to find clients. You have to serve clients. Then you have to keep that treadmill running in order to make a living. That was the equivalent, in my mind, of my freelance career. This all came about because I needed money. I understood that I needed something to sell, and the only marketable skill I had was the practice of law. I didn’t hate it enough to starve. Let’s put it that way.

I started yet another email newsletter. This one focused on legal issues related to the Internet, which not a lot of people really knew a lot about. I did. I put that out there hoping I would make enough money to survive. Frankly, it bowled me over. I got so much business that I could have done that full time. I could have built a law firm out of that. But, I still didn’t want to practice law. I was still hoping to keep the first business. The only one that ever failed was my first business. I still thought that would be able to make it, though I was only trying to make enough money to get by.

Inadvertently, because I didn’t want too much legal work, I ended up engaging in some of the best practices you’ll ever hear — and you probably have heard as a freelancer — such as specialize, be very picky about who you work with, create an air of exclusivity and scarcity. All of this stuff that is strategic and works to where you can work with the best clients, charge the most money, and have a happier life — that everyone is hesitant to do because it scares them to death.

Think about it. If you don’t care, like I didn’t, then doing that kind of stuff worked like a charm. But I was coming from a different place of not wanting too many clients. It’s a catch-22. We’ll talk more about that in the future because, if you can have the courage to act like you don’t care, it’s amazing, the effect on your business. But that’s for another episode.

I ended up with the best clients, the highest rate, the retainer agreements, basically the most stable income source and low-stress income source that I could have while I worked on the other business. The mindset shift at this point at the end of phase one, I went from thinking I wanted to be a writer to thinking I want to be an entrepreneur. I’m a person who starts businesses. It was thrilling to me. Instead of a writer, I became an entrepreneur who could write. Again, with this whole content and audience and all that kind of thing, it served me very well.

How I Succeeded at Money, and Failed at Happy

Phase two is what I like to call ‘hapless entrepreneur,’ 2002-2005. That’s a little misleading because I made more money than I’ve ever made before that point. I made more money than if I would have stayed with that big law firm. I was making more money than a lot of the partners in that law firm. Money and marketing were not the problem. The problem was I worked myself to death. Why did I work myself to death? I did not develop processes that would remove me from every little thing.

The business, the clients, they were thrilled. They were happy. Why? Because I worked 16 hours a day, personally making sure that was the case. That’s not sustainable. The business that I went in after the dot-com crash pretty much wiped out the prospects of the first business, which was a huge blessing. It was real estate. I had become an intensive student at this point of copyrighting and direct marketing principles as applied to this new medium of the Internet. I was just looking for a business to start that wasn’t law, that proved that I could go into another field as an entrepreneur and succeed.

You see there, I had something to prove more than I had passion. I had no passion for real estate. It was just very lucrative, and the competition did not know what I knew about anything related to online marketing. At that time, that was when the big shift of buyers looking for home listings online happened, combined with IDX, which is a technology, like an API, that allows brokers to display MLS listings on their websites. This was an entirely virtual business made out of websites, technology. No physical office, no traditional advertising. It worked like a charm. It was amazing.

I had great marketing. I had great tech. Terrible processes. Long story short, by the time I got to 2005, I was majorly burned out and unhappy. I went skiing, snowboarding, actually. Had a nasty fall. Long story short, I ended up with a subdural hematoma. I had to have emergency brain surgery. I’ll put a link in the show notes if you want to read more about that.

When I woke up from that, I was done. I was never going to do anything just for money again. I was never going to limit my ambition based on what I ‘should’ do. Here’s that word again because that business was making a lot of money. I had a little girl and a little boy who was just born. I was being the responsible business-person despite the fact that I was miserable.

Again, another huge leap. I actually sold the business to my partner and one of my agents. Within six months, they had run it in the ground. They could only afford to pay me out of proceeds. You get the picture. I got nothing. Once again, I took a leap. I ended up actually in a worse financial situation, but it didn’t matter. Because my mind had shifted in such a radical way, as life threatening events can do to you, that there’s just no way I was going back. My mindset shift at that point, create the business that I want not the one that I should. Huge.

The ‘Portfolio Entrepreneur’ Phase, and Why It Rocks

Next phase. Phase three, ‘portfolio entrepreneur.’ This is 2006 to 2010. This is the Copyblogger.com era, but not the Copyblogger Media era, which began in 2010. I basically started a blog talking about the marketing and content strategies that I used to build those three previous successful businesses, and it took off.

I had no business model for Copyblogger. All I knew was that, if I built an audience, opportunity follows. I would figure out what it is that they needed. That sounds very much like jumping and leaping without looking. In reality, it’s the smartest way to actually start up a product-based business rather than starting with a product and hoping someone buys it. You’re starting with a real group of people that you pay attention to, that you serve with content, with education, with value. Then they tell you, not directly, but they express problems. They express desires. You pay attention and you get that.

I learned my lesson about trying to do everything myself. When it came time to develop products and services, it was all based on collaboration. I had the audience. I had the content skills. I had the marketing skills. Pretty good at strategy and what not. Could not code, could not do everything myself, certainly, so I established relationships with people that could do things I couldn’t.

In 2007, my first partner, Tony Clark, we built an online training course together. He handled a lot of the design, coding, utility work. I handled most of the content. It was a good match. Later, I got into software. Again, not a coder, but I partnered with people who could create things while I handled marketing, distribution, and all that good stuff.

Basically, I was making more money than ever in my entire life again. Less hassle, low overhead. I was basically running four separate companies. The only thing in common that all those companies had was me. Though it came to a point, as we got to 2010, that I had all these smart people involved with me but they weren’t talking to each other. We had a bigger goal, a bigger vision.

How Ambition Can Override Lifestyle … If That’s What You Want

You may say, “Brian, why would you screw up something that great and go build a bigger company with lots of employees and a very different thing?” But again, it was another mindset shift. It wasn’t about money, again. It was about creating the company that was necessary for the larger goal, the larger ambition.

We had a goal to build something that none of those individual companies could build alone. It would take a unified, merged effort. That’s exactly what we did in 2010. We merged four companies together that form Copyblogger Media. The thing we wanted to build is now called the Rainmaker Platform — and it worked.

But I do refer to this fourth phase, the CEO phase, 2010-2015, so far, as my graying years. If you look at my hair in 2010 compared to now, lots more grey, and it’s not just because I’m older. I’m not saying things have been bad.

We’ve had spectacular growth year after year after year. Our objectives have been met. In 2014, we crossed $10 million in revenue. We’ve got over 50 people now. It’s all been good, but it’s a very different set of responsibilities to be a leader and to feel like you’re responsible for all those families. Me, personally, I’m willing to do all of this because of that broader goal, the broader vision that it takes this type of great fantastic group of people in order to do it.

I know there are some people out there who abstractly desire to be the CEO of an eight-figure company. Personally, unless there’s a reason to do that — again, a goal, an ambition — I don’t necessarily think I would do it. I would have stayed that portfolio entrepreneur, constantly starting new things, not owning perhaps the whole thing, owning a slice of it.

But here’s the cool thing that, as we sit here today, is still true. I’m still a portfolio entrepreneur. We’ll dive into this more, but my personal production company, Tangible Digital, owns my share of Copyblogger. It also owns a collection of other projects, including Unemployable.

These other business that I’m starting are not necessarily making a bunch of money, just like for almost two years, I didn’t make money from Copyblogger. You start it, and you figure out what people want based on actual interactions — questions, desires, problems, all of that good stuff. It’s a really cool model. You don’t have to build one company that has 50+ people and $10 million in revenue.

But if you do, hey, that’s not terrible. It’s a mindset thing.

I want to leave you with that. We will pick this up next episode and talk a little bit more. Thanks for joining me. As always, keep going.