Entrepreneurship.

The other day, I’m having a cup of coffee — no latte, just coffee — with a man whose opinion I respect. It is a mutual respect, one built over a long period of time. Some of that time spent in close consultation, some of that time passing with few words exchanged.

We get to talking about what it means to be an entrepreneur — between us we have more than 70 years of experience, but we both struggle to put meat on the bones of that subject.

Here is what we say to each other.

“I hate that word,” I say. “It feels like one of those bullshit words that we make up to describe unpleasant things such that they may be discussed in public without feeling as if we have insulted people.”

“Yeah,” sayeth he, “it is the kind of word people use to describe excrement, thinking that it will temper the smell.”

Our conversation goes back and forth along that same line.

“I don’t think you just wake up and decide one day you want to be an entrepreneur,” say I.

“Not unless you were born into it,” he says. “The sons of entrepreneurs have less difficulty with it, because every kid has a suppressed desire to be just like their old man. Even if they didn’t like their father and it is something they intended to avoid. Blood is blood.”

“Yeah, I think it helps to be a person who is not overwhelmed with respect or fear of society and order. One thing I want to add is that daughters are in the same boat these days. Plenty of daughters of entrepreneurs — both their mothers and fathers — become entrepreneurs.”

“OK, I’ve got no problem with that, but let me change gears on you. I remember being in the military [he, like me was a combat engineer officer, glorified infantry who build and blow stuff up] and getting a platoon and being given a one sentence frag order that often was, ‘Get your ass up there, lieutenant, and sort that shit out, most rickety tick.”

I laugh because I remember it the exact same way.

“At some time, an idea gets into your head and it begins to grow, like a brain tumor. You either decide you’re going to cure the pain (aspirin) or make life better (vitamin).”

“Yeah, I agree with that, but sometimes you just want to do something. When you [meaning me] were in the real estate business, I used to envy your idealistic desire to just build great buildings. It was so damn pure. Naive as Hell, Ayn Rand naive, but pure. And, by God, you did build some great buildings.”

“I wanted to do that since I was ten years old. I would look at those buildings and we would talk. They talked back.”

“Which says to me that being a little crazy is a good attribute for an entrepreneur. You agree?”

“Yeah, I think you have to be a little nuts, but you have to have something elemental — a burning, unquenchable fire in your gut.”

“And if you don’t have it? Or it isn’t an unquenchable fire? What then? Do you say — not for me or do you wait?”

“I guess you’re not ready. I think there is some real wisdom as it relates to timing. If you want to be an entrepreneur, don’t wait until you have a wife, two kids, a mortgage, college loans, a couple of car notes, and a boat note. Be aware of you own situation as it relates to timing and whether you can afford to stoke that fire in your gut.”

“I agree with that. Sometimes, the entire process from idea to signing the Articles of Incorporation and the Corporate ByLaws can be two weeks. The idea ambushes you and you say, ‘Why the Hell didn’t somebody else already do this?'”

“Yes, I agree with that. I do think that colleges are filling young people’s heads with the idea that being an entrepreneur is a higher calling, as if it’s the Holy Ghost and you.”

“Agreed, but I also think that colleges are being smart to realize it — entrepreneurship — is something different than just taking management or finance in college. The ability to get an internship with a startup or a venture capital firm is a huge leg up. Just learning the language is a step forward. The thing I ask myself is do any of these professors really know anything about entrepreneurship?”

“Like anything else in life, some do and some don’t.”

“OK, so what does it take? I’ll go first. It doesn’t hurt to be organized. The more orderly you are, the easier it is to see when you’ve wandered off the gameboard.”

“OK, I think if you’re going to be an entrepreneur, you should never go it alone. Find a co-founder, somebody who has a complementary skill. Nobody can have all the skills.”

“Fair play. I guess it’s obvious, but you have to be able to lead. You should discipline yourself to have a plan — Vision, Mission, Strategy, Tactics, Objectives, Values, and an idea of what the Culture is going to look like.”

“That was my line, damn it.”

“Where do you think I got it? OK, everything is going to take twice as long and cost twice as much; contingency is a real cost and you will spend every stinking cent of it.”

“Everything you work hard at — you will get better at, eventually.”

“You have to find your own rhythm, your own leadership style, your own voice. Don’t be afraid to tailor the message to the audience.”

“Not everybody is motivated by equity. Don’t force your values on anybody else as it relates to equity. There are a lot of people who want to come to work, do good work, get paid, go home, and follow some other passion. There’s nothing wrong with that.”

“Every step of the way, solicit advice from somebody who has done it before. It is not humility; it is just being smart.”

“Hire good people. Give them a clear charge as to what you expect from them. Write down their objectives. Have them tell you what they “heard” not what you said. Keep score using the objectives.”

“Failure isn’t fatal. Along the long road to becoming an overnight success, there will be a lot of tough days, weeks, months, and suddenly a light will turn on and you will realize — hey, I am making real progress. It takes, on average, seven years to become an overnight success.”

“When raising money, never get mad at the money. It will change its mind. You will talk to 200 people. 20 of them will be interested. 10 of them will come to a meeting with their checkbook in their pocket. 5 of them will write you a check. That’s the way it works. There are more reasons why someone turns you down than there are reasons why somebody writes you a check. Don’t fixate on it. Just get the money and build the company.”

“You will pivot at least once. The pivot will be fairly pronounced, but you will feel better about the azimuth you are on after the pivot than you did before the pivot.”

“There will come a time when you doubt yourself, doubt the idea, doubt the market. Get a good night’s rest. See if you feel the same in the morning. If you do, don’t tell anybody. Think your way through it. Go see a trusted confidante. Tell him what you are thinking. Back up every sentence with a fact, evidence, data. You will feel better though you may still have doubts.”

“When you feel those butterflies in your gut, hang on. They will become condor size soon with great big talons and they love to swim in stomach acid and tear your guts apart. Unfortunately, that is perfectly normal.”

“Good one. There are a lot of people who have trod this path. You can do it. Promise yourself you won’t look back for a year. When you do, you will be amazed how much your have grown, learned, accomplished. But it takes a year.”

“Forgive yourself for everything except being lazy. There is no excuse for being lazy.”

“Luck plays an enormous part in everything. The earlier you come to work, the later you stay, the harder you work, the luckier you get.”

“Nobody ever drowned in their own sweat.”

“OK, now we’re just getting sloppy. That’s the end.”

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car. Have a great week.