The board is not your father and also, not Darth Vader

I’ve started six companies, two are in progress and four have exited. Through my journeys I’ve accumulated many lessons and even more scars. Here they are, the things I wish I had known. Some of them I keep relearning, like a donkey bumping his head into the same tree again and again.

The board is not your father and also, not Darth Vader

I think many founders imagine the board is there to offer advice and assist. Even be a shoulder to cry on. Nothing could be further from the truth. A good board member is a state machine with no memory. He/She will give you the best advice they can based on the information you give them at that moment in time. That’s the job. So sort yourself out before you call.

Another board lesson

Never show up to a board meeting without getting consensus first. Otherwise you have a bunch of people with no recollection of the last conversation, trying to figure things out together. Your board doesn’t hate you, they are busy, and assume you can run the company. If you can’t they will get rid of you. It’s the job description.

One more for the board

Be accountable. This is another one about them not remembering anything. If they need to remember whether or not you delivered on your promises, they will be stressed. Show up and say: “last time I said this and I failed at some of it” followed by details. This way, you are one less thing for them to worry about. Be the easiest thing in their busy day.

It’s all about the business cycle

Start ups that don’t run out of money don’t fail. By definition this is true. If you run out of money it’s because you didn’t plan for the business cycle. Unless you are making money fast, you need to raise against milestones and achievements. It’s as simple as not putting enough gas in your car to get to the next gas station. The map is the business cycle, the decision cycle, the product cycle etc…you get it.

Don’t trust your lawyer, even when he's telling the truth

Your lawyer is not a business man/woman. If he or she was, they wouldn’t be a lawyer. If you are letting your lawyer give you business advice, you must be truly lost, or lacking confidence. Either way you’re falling down. Trust yourself. Even if you’re not sure, by definition you know your business better than anyone.

You are not a trickster…or are you?

My favorite book on the reality of entrepreneurship is “Trickster Makes This World: Mischief, Myth and Art by Lewis Hyde et al.” Take Prometheus, who stole the fire from the Gods and gave it to man. Bill Gates, brought us the PC from IBM. The entrepreneur feels comfortable in the chaos. He gets it, while others don’t. Then things settle down and folks think they don’t need him. Then he gets crucified, see Prometheus, Loki, Joseph…Steve Jobs got fired. Enjoy it, you are part of a long tradition. One time, after I sold my company, a board member who was CFO at large public company, came to me and said “I heard you walk on water.” I should have known what was coming next, same as that other guy who walked on water.

Delegate don’t abdicate

The first time you go from 2 to 12 to 70 people you don’t really understand how an organization works. you might think putting someone in charge is the definition of delegating. Actually that’s abdicating. Delegation is when someone else is in charge and you are responsible.

Lightning in a bottle

So much of success is about luck. Especially first time entrepenuaers who crush it. These people are still way more awesome than you, because at the end of the day, it’s about execution. Not being lucky is no excuse. Own the bottom line. You’ve either won or you haven’t. Greatness often comes as an overnight success that was years in the making. Another way of saying it: failure is not an option so long as you decide that the game ends, when you win.

Better scared then bored

It’s why you’re doing it. My motto is “better scared then bored…except for when I’m scared”. Someone once came to me for advice about his aspirations to be an entrepreneur. At a certain point in the conversation I looked at him and said “this is not for you”. If you need to check the temperature of the water before you jump in the pool, go get a job. (At the time, I actually said “if you’re checking to see if there is water in the pool etc.” but now I think it’s ok to check for water). Entrepreneurship is defined by its uncertainty, embrace the uncertainty..it’s your destiny.