The Introduction Part

There is a lot of talk about entrepreneurship these days. Not that it’s a new subject, mind you. Indeed, without entrepreneurship (if we are to take the word to the full extent of its meaning), the world would be an exceedingly bland place. However, with the rise of the internet and the associated technology and platforms out there to make it ever more accessible there has come an unprecedented ease of entry, as it were, into the marketplaces of the world. There has also been, as should probably be expected, a corresponding rise in the marketing of dreams come true being just a few simple clicks away. “Buy my course, bro. Buy my course. It’ll change your life”.

Terms like “digital nomad” have become common place among those who would seek a better, easier and more financially rewarding way of life. A life lived travelling the world and working from a laptop. A life lived far away from the horrors of being canned in an office with its dresscode, flourescent lights, office politics and the slow but inevitable creeping up of middle age.

“I’m with a small startup building a paradigm shifting, scaleable, multi-platform, real time updating, ultra user-friendly product with a team of super talented programmers that just happen to be the same people I get drunk with on the weekend” or words to that effect is another common one. Yes, anyone can be an entrepreneur, no?

In the meantime, the rest of us dumbasses are left  to somehow navigate the truth that you are selling your time to someone else while the dreams you had in your youth become evermore spectral and distant.

“Ah, remember when we were going to start our own business selling Beanie Babies?”

“Come on, man. It’s Friday. Don’t talk like that. Happy Hour at the usual spot errr….?”

“Yeah… I mean..I guess. Let me get my jacket. It’s just that…”

“Dude, shut up about the Beanie Babies thing. Seriously, That was just a pipe dream, bro. Nobody even buys Beanie Babies anymore, dude. Come on.”

And so it goes.

Ouch! Is that a bit heavy? Yeah, maybe. But the truth is there are generally more than a few hurdels between the would be entrepreneur and success at entrepreneurship. And there must be the spark; that one event or thought or conversation or realization that leaves with the resolve to actually drop shop, stop talking and start doing.

For me it was a slow burn of frustration and my patience being tested by increasingly bizarre people in equally bizarre environments with little or no promise of things ever improving or incentives ever arising. I had peaked in my mid twenties and it was either accept that (and the salary) or move on. So I moved on. It’s doubtful I ever would have entertained thoughts of such things if I hadn’t been so utterly dissatisfied with my working situation. It is quite true that we grow not for lack of adversity but often because of it.

Looking back, it is surprising how much we can take and how much we can get used to simply because it is easier than taking any kind of massive action to change your life. Interestingly, though, once you do start to take action each incremental step brings with it amazing value and potential. And that’s because you are actually building something for you and your family; assuming you have a family. But, incremental steps are, well, incremental. So it can be somewhat difficult to notice any significant change or progress for quite a while. Especially if you are a narcissist or have somehow never come to terms with the fact that the world in general couldn’t care less about who you are and has a fundamentally different nature than you imagined it to have when you were still in high school. Not to sound condescending but it is a mistake to put too much importance on yourself simply because you are you.

However, the fact remains that anybody can be an entrepreneur. And, I would venture to guess, that it has never been easier. But that may be a little misleading to say. Let me rephrase that. It has never been easier to get started as an entrepreneur than it is today. Succeeding. on the other hand, is probably just as frustrating, dumb, hard, time consuming and scary as it ever was.

Anyhoo, to the question below:

What is an entrepreneur?

Most have some general semblance of what this word means: “It’s someone who has their own business, bro.” And that definition is generally useful enough to hold a conversation with people about the subject. But did you know that this is actually a compound noun? That is, entrepreneur is a combination of two words from French?

They are:

entre: “to enter”


preneur: “taker”

So effectively, entrepreneur means something like “entrance taker” or “one who goes in first”. It can also be translated as “builder” which brings even more connotations to the word. It is always an interesting experience to look a little further into the nature of the language we use on a daily basis and to gain a better understanding of all those words and stuff, no? Entrepreneurship, in the literal sense of the word, it would seem extends not simply to businesses but really to any creative endeavor. In a very real way artists, inventors, scientists, warriors, leaders farmers and anyone trying anything new in a new way to make something better or more interesting could understand this notion of entrepreneurship: entering into something.

Anyway, returning to the conventional meaning of the word, the notion of entrepreneurship meaning not only to run a business but to conceive of it, build it and enter into it all by your lonesome is exactly what makes it, well, so effing hard. Yes, entrepreneurship is hard. Even if you sign up to all kinds of Mastermind Bros Facebook groups and jabber at coffee shops about yourself and wear skinny jeans and call Gary V your “guru” and take 200 selfies a day, a lot of the real process of being an entrepreneur is going to suck. We’re talking less sleep, less income, more stress and more responsibility not as a temporary thing until your genius finally becomes known (took you long enough, guys) but as a way of life. A way of life you willingly enter into with absolutely no guarantee as to what’s at the end of the tunnel. Yes, eventually the less sleep less income thing will eventually change but it will take time. And in the interim, as Yoda would say, “questions yourself you will”.

So it is a very, very good idea to ask youself if you are cut out to be an entrepreneur. Or, at the very least, to ask yourself if you are willing to go through the process required to get there.

Keep in mind, I’m not trying to speak as a hyper successful billionaire entrepreneur here. I’m simply stating the universal facts of the situation based on my own experience. If you’d like to learn about the specifics of what I went through personally (starting an English school in Japan), you can read about it here on my blog at If not, read on to discover the key points I learned calling it quits at my weird hack office job and striking out on my own:

You will be working for free: yes, gone will be your salary and, in its place, you will be paid nothing. In fact, until the revenue you gain from your clients exceeds your expenses you will be a nothing master, my friend. Oddly, this wasn’t immediately obvious to me. After working like the dickens my first week I kind of happened to notice that I hadn’t actually made any money for it. There was no pay day coming.

It will likely be more expensive than you think: this really depends on the particulars of the industry and business model you go into. There is a tremendous variance here but suffice to say that it is generally true that your expenses will be far more expensive than you previously thought. They will also be in addition to your normal living expenses. Personally, I ended up paying two rents, two sets of utilities, two parking lot rental bills a monthly remodel loan payment and my own health insurance and social security payments. This is something to take into account (pun intended) when you are starting out as being unable to meet your initial operating costs can very well sink your ship, so to speak, before it gets out of the harbor.

Be gosh darn careful with the capital you have: whether your startup capital has come from investors, a loan, your parents or your savings it is one of the most precious resources you have. And, my oh my, can you go through it in a hurry if you’re not careful. Admitedly, I was something of what is technically referred to as “a dumbass”. That is, unused to such funds in my account I reverted to the 10 year old with a job mowing lawns mentality and simply spent it here and there without really keeping track of it. It doesn’t have to be something that keeps you up at night but you shouldn’t get too deep into the “it’ll be cool, bro” mentality either. Economic reality can be a savage beast when you are handed the bill in full for not staying on top of your expenses.

You will be forced to deal with things you never saw coming and there will be dumb obstacle after dumb obstacle: Have you ever worked for a company and constantly asked yourself “Why? Why does it have to be so dumb?”. Well, it turns out flawless concentration and the ability to manifest the perfect system are extremely rare in this world. As the guy in charge you will be made utterly and completely aware of this little fact. You may be surprised by how many unforeseen obstacles arise. Some of them your fault others; simply the fault of the world for being the way it is. However, the biggest obstacle, it turns out, will likely by you. That is how you manage your time, your customer relations, your health and your dedication to the job. You see, as an entrepreneur, if things go south there is no one to blame but yourself.

There are also times when the most bizarre things come screaming out of the blue simply to ruin your day or potentially even your business. I will never forget the day my school nearly flooded because of a typhoon. The water got in but only enough to soak the first meter or so of carpet along the windows. I ended up ok but it was certainly no fun getting there. A flood? Are you kidding me?

It will likely take longer than you think: This is another one that caught me by surprise: the time it takes to bring your monthly revenue up to a point that equals or exceeds what you were making as an employee. Assuming you don’t somehow justify yourself in stealing all of your clients from your previous employer and thereby give yourself a ludicrously unfair start, it will likely take some time for you reach the point where your revenue (after expenses) equals roughly what you were making on a monthly basis at your job before. It took me roughly 3 years. And, even now, my income can fluctuate like crazy. Thankfully, the income on my worst months is still higher than my best was as an employee before. Yes, there is secuirty in having Ye Olde salary. But, in being an entrepreneur you will, at first, have nothing. Ideally, this will be a temporary phase after which you will return to your previouse income and then hopefully surpass it. But it will usually take a bit longer than you think.

Until that time comes, it’s not a bad idea to live as simply as you can.

“Question yourself you will”: More bills? Less income? More stress? Less time? Is this what I signed up for? Nooooooooo! That’s impossible! But, you see, it is possible and, for most of us, there is no going back save for chapter 11 bankruptcy or simply leaving town.

You will gain a new understanding of the term “thick skin” and you will grow stronger: as the one responsible for the success or utter failure of everything, you will necessarily be on the frontlines where your business meets the marketplace. You will deal with the ins and outs, the ups and downs, the profits and losses and the plain stressful complexity of keeping things going. And you will grow stronger for it (provided you don’t pop your cork and run away to go hide somewhere in the interim). You will learn to take the long view, to cut your losses, to take things less personally and to rebound faster. And you will do so because you have to. It’s the only thing you can do if you want to keep moving forward.

You will grow more independent: along with growing stronger as a person you will also likely grow more independent. You will find it easier to say no to people and things you know will simply waste your time and energy. You will also learn to be cool with being alone, putting a ton of work in with no guarantee of any return and other things like acting like a decent human being with manners.

You will find a new sense of appreciation and value for everything around you: once you reach whatever your personal defitinition of “success” happens to be, you will likely have cultivated a new perspective toward the complexities, risks taken and efforts made in the nearly countless elements of your daily life: the roads you drive on, the house you live in, the parks you visit, the stores you go shopping in etc. All of these took tremendous amounts of time and effort to create and, personally, my own journey as an entrepreneur has made me a lot more aware of this.

You will look back on your past and wonder what took you so long to get started: This one is a weird experience. If you do make it as an entrepreneur, even in a small way like me, you will likely look back on your time as an employee at other jobs and wonder why you stuck around so long. You will wish you’d started what your doing now years ago. You will imagine where you could’ve been by now.

You may even, oddly, feel a sense of regret at not getting started earlier. But this is to deny the fact that you are exactly where you are exactly because all of the events in your life happened exactly the way they did. Like, exactly, bro.

You will get the urge to try other ventures: your first taste of succes at entrepreneurship carries a strong potential of sparking the desire to pursue other ventures. To come up with crazy new ideas, cockamamy plans even, of making money and creating products and service for people. This is where the term “serial entrepreneur” comes from. And it can be an amazing thing; especially if you are the type to learn from your mistakes and streamline your process in future endeavors.

You might utterly and completely fail: This is an unfortunate and sometimes harsh reality of entering into something new. It could end up a mess. It could humiliate you and make you look super dumb. It could bankrupt you. It could make you miss the days of being a hack working for someone else. It could even mean moving in with your parents and living in their basement (if they’ll have you and they have a basement, that is).

Yes, failure is always an element. But it can also be a teacher of valuable lessons and an absolutely indisputable reality check as to the relevancy of your idea and the level of your sklls. One thing is true: the market doesn’t lie. And no amount of justification, spending of capital, marketing or generaly dumbassery will convince the market you have a good idea if it’s, well, not a good idea. However, what you learn from failing can often teach you more than a decent business school and in a way that is as visceral and real as it gets. But you have to make sure you don’t pitch a fit about it and give up like a spoiled little girl. No, no. That simply won’t do Because, even in failure, there is progress but to give up entirely is to also put an end to any progress you have made. To say nothing of how dumb you’ll look. 🙂

Alright. So there it is. The things I learned along the way from hack to entrepreneur. Knowledge and experience are funny things. The results of them are all around us yet they can be so very elusive when you really need them. Thankfully, you don’t have to learn everything in life the hard way. And I think this is what is implied by all the talk concerning entrepreneurship here in the information age. It’s not that it’s easy to get there. It’s just easier to access the resources and knowledge to help you get started.

Personally, the most important lesson I’ve learned in my short 4 years since going solo is have a plan and know where you are going and what you are working toward. Despite my sarcasm regarding “Startup Bros Mastermind” groups and tight jeans, there really is a lot of wisdom to be gained out there by doing your research and getting in touch with the right people. You also need to stay grounded and realistic, though. The number one reason people fail is because they think they are someone they aren’t or they have something they don’t; they get too excited, skip the groundwork and blow up before getting to the end of the runway. The number two reason is because they are more in love with the image of being an entrepreneur than they are with the process. And it is a process. Sometimes a long one, sometimes a hard one but almost always an interesting one.

Good luck and have fun.