What Being an Entrepreneur Has Taught Me

I always said I would never start my own business because I didn’t want a jerk for a boss, but on a several occasions the entrepreneurial drive (or perhaps worms) has driven me from the ostensibly secure halls of corporate American out onto the mean streets of entrepreneurship. Out there, fighting tooth and nail for every scrap of work with the ravenous brutes that are the mom-and-pop shops and gigsters of Entrepretopia, I’ve learned a thing or two.

Never put your ego in charge.

A good friend of mine owns his own pallet reconditioning company. He answers to no one, but on his card his title reads, “assistant general manager.” I was giving him some grief about his inability to get an executive position in a company he owns, and he said titles don’t mean anything to him, but it’s always useful in negotiations to claim to have to run a deal past an imaginary boss. It may sound a bit dishonest, but it has allowed him some much needed wiggle room and the ability to turn down some ruinous deals.

Ex-coworkers aren’t necessarily the best leads.

I’ve worked with hundreds of people throughout my career, and many have said I am the best at what I do. Sounds like I should have a golden ticket to success, right? But as it turns out I’ve had very little success selling to ex-colleagues, and I’m not alone in having this trouble. I have worked for several large entrepreneurial firms who hire (usually for a king’s ransom) some hotshot ex-Fortune 500 executive, believing that he or she will be able to leverage contacts and bring in big contacts. In most cases it doesn’t happen. I’ve been on both sides of the equation and I have to say that it was difficult sourcing business to ex-colleagues. It’s something about the blurred lines of the relationship -- a bit like finding out that your new girlfriend once dated one of your friends -- no matter how little reason there is to have things be different, they are. This Pet Cemetery change in the dynamic starts feeling creepy, wrong and uncomfortable.

Of course, that could just be me.

There is never a good time to start a business.

Unless you’re a trust fund baby, there isn’t really a good time to start a business -- you’ll always wish you had more startup capital, more advance orders, a solid customer base or at very least a wealthy 96-year old uncle with no children who still smokes two packs of filterless cigarettes a day despite chronic emphysema and a cough that sounds like a death rattle.

The reality is, starting a business is just like any other major risk -- is there ever a good time to get married? Have a baby? Buy a house? No, but we do it anyway because life is risk and the bigger the risk the greater the reward (well, except for using heroin, that’s just stupid).

There will always be plenty of people to discourage you.

People hate to see people embrace the risks and grab for the brass ring; it reminds them how few opportunities they have pursued and how miserable they are to see people succeed as they look at their own miasmal life and think of what could have been, if they had just had the guts to act. Misery loves company, this we know, but misery loves company so much it will actively make those around it miserable. Go easy on them; they're not mad at you, they just wished they had made better choices in life.

Consider that you may not be a genius.

In his seminal poem If--, Rudyard Kipling observes, “if you can keep your head while all those around you are losing theirs and blaming it on you, if you can trust yourself while all men doubt you, but make allowance for their doubting too…” It's good advice: I am all for staying true to your vision and resolute in pursuit of success, and many’s the time when I had to keep my head while all those about me were losing theirs and blaming it on me. But it’s always been the last line that has resonated with me, “make allowance for their doubting too…” In other words, when someone tells you that your idea is stupid, consider that it might be just that. For every misunderstood genius out there, there are 10,000 perfectly understood idiots; it pays to occasionally consider that you might be totally out of your mind.