FearlessnessThere are countless things that I’ve learned about business during the past decade or so, things that have been learned working for other companies and things that have been learned building my own. Being the owner of a company where I also have a full time job means that you learn some very interesting things about people who play on one side of the fence or another.

In particular, there is a huge chasm of difference between those people I’ve met who are entrepreneurs and those who choose 9-5 career paths. Of course, talking to people who work for someone else you’ll hear many of them talk about their own ideas for great success – building their own ideas and companies, eventually escaping the corporate world for one of their own choosing. Why is it then that so many people end up sticking in those careers for 10, 20, even 30 years? In my opinion, there are three major differences between a “true” entrepreneur and people who only dream of being one:


During my time running my own businesses and working for companies I don’t have ownership in I’ve had to opportunity to meet a ton of very successful people, and some very unsuccessful people. One of the biggest themes that you’ll pick up about those successful people, and specifically those successful entrepreneurs, is a sense of fearlessness. Whether it means quitting the day job to start the business of their dreams or investing their life savings into their idea, these are all the same people who have such optimism and grit that they’re willing to put all their chips into their endeavor just for the chance at success.

Fear is the biggest hurdle to overcome when it comes to starting a business. If you’ve ever worked in corporate America making a solid salary with benefits and 401k matching options it can be absolutely terrifying to take away that safety net. What if things don’t work out? What if you get sick? What if the economy sours?

Questions like those are the dividing lines between people who go into business for themselves and people who don’t. In this sense starting a business is just like jumping out of an airplane. Will your chute open or won’t it? There’s only one way to find out, and that’s that fearlessness innate to entrepreneurs that makes all the difference.

Failure is Guaranteed

Great, you made the jump out of the plane. Good for you. Now let’s talk about your chances of launching a successful business.

You usually hear things like “failure is not an option”, but when it comes to starting your own business, failure is something you absolutely have to get comfortable with. I’m not talking about catastrophic, ‘you can’t pay the rent and you have to live under a bridge’ failure, I’m talking about a lot of little failures that add up over time and seem to cripple many people into giving up.

These can be failures like not winning your first big account, blowing a presentation, not getting the funding from an angel that you were pinning your hopes for the year on. It could be not driving as much revenue as you wanted, having to let go of one of your first employees because you can’t pay all the bills. While these are very real failures there is a distinct difference between how an entrepreneur handles it and how a dreamer handles it: Entrepreneurs understand that losing a battle doesn’t mean losing a war. They understand that “overnight success” is a make believe term and that most of the successful owners you hear about had to grind it out, day by day, year by year before they had their shot.

For those people that had the courage to make the initial jump into starting a business this is a truly terrible way to end things. To chase your hopes and dreams, to make that big gamble on your own success, only to see it disintegrate before your very eyes. The truth is that not every business will make it and that not every business was a good idea in the first place. Behind that, though, there are some very successful companies that came right up to the brink of failure only to keep the faith and keep pushing along until they found success.

One of my favorite examples of this mindset is from FreshBooks founder Mike McDerment. You can read about the failures they had to come up against here.


Read anything about starting a business and you’ll pretty quickly come across the term of being an evangelist for your company. To be honest, this seems like a hokey buzz word people throw around a lot that means nothing (think ‘synergy’). You need to peel away at it for it to be prescient in the slightest.

Try consuming the idea of evangelism this way: Nobody cares about your company the way you do.

While your friends and colleagues may be interested in your idea or your endeavor, they don’t really care the way you do. They have full time jobs, kids, and their own problems to worry about.

A long time ago I thought that some of my ideas were so grand that they would blow people away. That people would be so impressed that they would immediately band around it and launch me into the stratosphere of success. Boy was I wrong. Reactions have ranged from mild interest to downright awkward changes in conversation topics, and that’s not a bad thing.

As the owner of a business, I am user number one, the earliest of adopters. It’s lonely being alone, and it’s not going to change unless I put in the work to convince people to adopt as well. That means perseverance and not expecting everyone to share my fervor.

For the successful entrepreneur or potential entrepreneur out there this means that you need to embrace the fact that you’ll be in sparse company for a while, that you can’t let disinterest get to you. Even mighty Google and Facebook had to overcome these in their own right, so why would you get a pass?

There are plenty of other factors and habits of successful entrepreneurs available, and much more verbose ways of covering the same topics, but in my opinion how you handle these three facets of business ownership are foundational pieces that will largely determine success or failure.

Steve is a career online marketer with over a decade of experience managing large scale online marketing campaigns (SEO, SEM, etc.). He is also the co-founder of ListHere.com, a small business marketing platform focused on the classified ad marketplace.

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