Years ago, I asked a friend who was obsessed with golf where his obsession came from.

“There are two things about golf, Micah,” started George. “The first thing is that is the ultimate competition. Just me against the course. Every time I play, the course presents new challenges.”

George then lowered his voice, as if he was telling me a big secret. “More importantly, when you play golf, there is a moment when you hit the perfect shot. Then, for the rest of your life, you are trying to hit that shot again.”

Recently, I have been thinking about what makes an entrepreneur unique. Why do we do what do when we do it? What compels an entrepreneur to get up after being beaten into the ground, only to rise up and do it all over again?

We are chasing the perfect success.

At some point in our lives we experienced what we consider to be the perfect success. It may not have been something that drove a lot of money, it could have been something extremely simple, or even a short series of events.

For me, my first perfect success was when I was nine, and I was able to convince my friends and cousins to work for me. When I could articulate a vision (lets make enough money to go to Jack-in-the-Box and see a movie) that everyone bought in to. (BTW, that perfect success was followed by my first failure, when Jack-in-the-Box screwed up my order and the movie was so bad, I, for the first and only time in my life, walked out.)

In many cases, this perfect success isnt self-evident when it occurs. Its is only afterwards that we realize how important that moment was, and how much we both miss and want it again.

Drug addicts will often talk about the “perfect high.” How they will reach a point where they are exactly, perfectly euphoric, and then the moment passes and they spent the rest of the time trying to achieve that moment again. As they get more and more addicted, it gets harder and harder to achieve that moment.

Same with entrepreneurship. It gets harder the more you do it. The expectations rise, the game gets bigger. Most entrepreneurs dont look to do something smaller after a positive outcome, rather they look to go big. Their sense of the perfect success has grown beyond the initial idea.

By the time I got to high school, making enough money to eat and see a movie was no longer interesting. I knew I could get people to work with me, and I ran several smaller businesses (the biggest was probably a pool cleaning business), but I started to learn that I could profit from connecting people. As a broker, I would connect buyers and sellers of things and take a small cut. I guess you could say I was Independence High School’s personal eBay.

In my pool cleaning business, I hired the most popular kids, which gave me access (and protection – which if you know Independence High in San Jose, was important), and would create connections that ultimately created win-win-win relationships for everyone.

For each of us, there is a perfect success that we are trying to achieve. We talk about it; we think about it; we analyze it. We test and retest and do it over and over again, until there is that moment of achievement that cant be surpassed.

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“Micah has a lot of potential that he is leaving on the table. He should leave his ear open and his mouth shut.”

My teacher, in Kindergarten, scrawled that across the bottom of my year end report.

“Micah needs to spend more time inside the lines.”

Another favorite line from that report.

Right now, most people reading those two lines are doing what I did when I read them (yes, even at 6 years old), laughing. Micah staying within the lines? Forget it? Listening, rather than talking? C’mon now.

Yet, as much as I would like to discredit those statements, the truth is that they are well, true.

Lets talk about the second one first. To operate within a society effectively, one must, at some level, be part of that society. One most embrace the similar. Even if your goal is to change the status quo. Stick with me for a minute. Its important to be familiar to those that you want to engender change, so that they dont need to overcome acceptance of you, before they work on acceptance of your ideas.

Now, I would consider myself in many ways to be different. Eccentric even. I have tattoos. I wear shorts and flip-flops every day (even in winter). You have probably seen me not wear a t-shirt, specifically a Threadless tee, maybe 6 or 7 times in my life. I swear awfully (my favorite swears are “fuck ‘em” and “those motherfuckas!”) I have weird eating habits.

This difference in many ways is a hindrance to the acceptance of my ideas. I know this. I think that those that are willing to accept the crazy realize that there is something interesting beneath. The people that end up joining with me on the crazy adventure of a startup tend to walk, in many ways, to the beat of their own drums. Its our collective crazy that leads to overall success.

I battle with myself to spend more time in the lines to ensure that people (partners, friends, employees, etc) dont get so hung up on the crazy.

Ms. Rock’s (I think that was her name. It might have been Ms. Shoelaces) assessment that I need to open my ears and keep my mouth shut was equally astute.

Last year about this time, I was invited to attend the Summit Series conference in DC.

I took a red-eye from SF to DC, and randomly, my friend Thomas Knoll was on the flight. He invited me to breakfast, and as we walked over with a group of people, I met Ethan Bloch. Ethan looks just like that dude in Royal Pains, and is one of the smartest people I have ever met. His business partner, Dan Martell, was someone who people had suggested I meet, so over the course of three days, Ethan, Dan and I connected several times. I learned a ton about Flowtown, which is a solid startup, but more importantly, I learned about how Dan and Ethan ran the company. How they decided on new products, how they interacted with their customers. I learned about something called Lean Startups.

The basic premise of Lean Startup is that you ask before you build. You keep yours ears open and your mouth shut. I spent a lot of time over the course of the next several months reading and learning about the concept and practice of Lean Startup. I asked a lot of questions. I listened.

A couple of months ago, I started to teach myself Ruby on Rails. There is a concept called TDD (Test Driven Development). The idea is build a test that when passed will indicate that you have built the right thing. Imagine that.

So, if you wanted to build a test for say, scoring a touchdown, your test would determine the location of the football, and if it was in the end zone, and a certain set of rules applies, then it would pass. As you coded, pieces of the test would pass, pieces would fail, and you would continue to develop until the test passed in full.

Lean Startup, in many ways, is the application of that concept to product development.

What is a success to you? Who is your customer? What is their problem that you are solving?

These are all tests that when you begin, you are failing. All the product development you doing are to pass the tests. Sometimes, that means building something completely different that you originally planned.

It also means that you have to connect and speak with your customers. It means that in the process of product development you have to keep your ears ope and your mouth shut.

I guess I really learned everything I need to know in Kindergarten. (Thanks Ms. Shoelaces, Dan and Ethan for reminding me of that).

Related articles

• Lean Startup is a Rigorous Process (ashmaurya.com)
• A lean startup isn’t necessarily a small one (venturebeat.com)
• Dan Martell Shares His Journey, Cust-Dev Case Study of Flowtown (foundora.com)
• Why I am an Entrepreneur (learntoduck.com)
• Flowtown: How It Failed Then Succeeded At Creating A Product Customers Love – with Dan Martell (mixergy.com)

There must be something in the Boulder air, as there seems to be a large amount of contemplation going on. My friend Brad is closing in on his 45th birthday, and it seems to have forced him to turn his thoughts internally, having written about it more than once.

I really like taking most of the Thanksgiving holiday to spend time with myself. I usually dont go home or hang out with friends. Most invitations are declined, and I try to stay silent through out the four days.

After a fairly messy six months at Graphicly, the question that seems to be sitting in my brain is a simple one: “Why am I an Entrepreneur?”  After all, if I had chosen to work at a large company, and had worked my way up the ranks, there is a pretty good likelihood that I would have a solid job. Maybe a wife and kids. Perhaps a bunch of golf buddies a solid 401k, and if everything worked out properly, I would get to have sex with my wife more than once a week.

Why did I chose the life of an entrepreneur? For most, its a lonely life. You spend more time with your laptop than any living creature. I have literally worn through keyboards and watched computers smoke because of how hard I push them. I travel so much, that I really dont know Boulder very well, or have a local network of friends. If I were to list out the folks I physically spend the most time with, none would be in Boulder.

Its a cheap life. I make less money now annually than I did 5-6 years ago. Yeah, I had the exciting times of building and selling a company, but mostly because of my own idiocy, not much of that money is left. I put a fair amount of cash into Graphicly in the early days, which caused many to question my sanity, but I believe strongly in where we are going. I watch most of the pennies that exit my pocket now, and often spend money on Graphicly and its employees without reimbursement. Does that make me some sort of saint? No, it makes me an entrepreneur.

Its a life of questions. Being an entrepreneur is living a life filled with questions. Every day I wonder if the decisions I am making are good ones. Am I truly helping Graphicly grow? Am I helping everyone within the company get better? What about the team? Is it solid? Can they gel? Am I stepping up enough? While the company may fail; I want to make sure that I am not the reason for that failure.

So why do I do it?

I love problem solving. I love being creative. When I was in the 5th grade, I decided I wanted to learn a musical instrument. So I chose the trombone. Why? Because I liked the fact that you changed the sound by moving the telescopic slide, and that precision mattered. (Apparently, my mom decided that it wasnt the best instrument for me to learn, since after several practice sessions at home, she suggested the violin. And by suggested, one day the trombone was replaced by the violin. When I asked my mom, she simply said, “Micah, trust me, the family and our ears will be pleased by this switch.”) Over the years, I have tried to learn all kinds of instruments, none of which I took to.

I want to be part of something bigger than myself, but in which, I had a hand in building. I want to be able to look back at my accomplishments and see my fingerprints in them.

I enjoy leading. Its hard in the corporate world to find a position that gives you the opportunity to own a project or lead a team at an early ago. My first job out of college was at a non-profit in DC. After a couple of weeks, my boss called me into her office and sat me down.

“Micah,” she said, “You have to learn that you have to pay your dues.”

Silent, I looked at her quizzically.

“Let me tell you a story.” She lowered her voice as if the mere telling of the story would raise the demons of her past. “When I started my first job out of college, I came into the office one Saturday, and re-arranged all the furniture. Can you imagine?!?”

I could, she was a pretty proper person.

“The hubris I had to assume that I, fresh out of college, could rearrange the furniture without even asking. That I would assume that everyone would just be okay with it. Do you understand what Im saying, Micah?”

I did.

I realized at that exact moment, that I would never be successful in a big company. I am not a dues payer.

So why am I an entrepreneur? Because when I rearrange the furniture without direction, I will be judged by the arrangement, not my age or rank. I wanted to be able to succeed or fail based on my production and contribution. I wanted to control my ability to be successful, and help the people around me be successful, not because I know how to navigate the politics inherent in a large organization, but because I enable people to be successful through their own efforts.

Mostly, I am an entrepreneur because its an expression of who I am, and regardless of how hard Ive tried in the past, I can just be me.