Why You Should Never Hire an Entrepreneur

The last time I went to work for someone else was more than 20 years ago.

I was barely paying my bills and had spent the previous several months renting office space from a chain-smoking, 70-year-old car dealer while trying to come up with my next business plan. Out of desperation, I decided to take a job as a marketing director for a company owned by a professional acquaintance I admired. He ran a really good business, which I pretty quickly saw I could parlay into no less than 12 other really good businesses.

I brought my plan to the CEO and made what I considered to be a very reasonable ask. In return for building out these currently non-existent spinoffs, I wanted a 10 percent equity piece of any that came to fruition. My boss demurred, saying he didn’t give out equity to employees. Instead, he offered me a generous salary that anybody in their right mind would be happy to accept.

I quit on the spot.

We could get into the financial wisdom of this move–my wife and I certainly did. But in the aftermath of this seemingly dubious gut call, I was much more consumed by how this man could possibly reject my totally sensible proposal. After all, he knew me well enough to know that a fat salary was not what I was after. But now I recognize that in refusing my request he might have simply been abiding a business tenet I’ve long since adopted myself: don’t hire entrepreneurs.

Don’t get me wrong. Like any rule, there are no doubt going to be exceptions to this. And I certainly have nothing against other entrepreneurs, who are some of the most powerful and amazing forces on the planet. They can raise capital, recruit a team, build a company, and unflinchingly face a host of cataclysms that would wilt most other people. But they also tend to be obnoxiously over-opinionated, seek constant attribution, and routinely show a complete lack of willingness to take into account other points of view.

They can be dynamos and icons and world-beaters in companies of their own creation. But working for you, they’ll be far more interested in proving themselves right than they are in helping you accomplish your goals, will outright refuse to do what you tell them, and likely won’t care about the success or failure of any business they aren’t actively running.

These aren’t knocks. In fact, these are the exact attributes many entrepreneurs must draw on to survive the gauntlet of doubts and obstacles that come with building a company from scratch when nobody thinks they can. But to hire someone with these qualities for your business is the equivalent of moving a bobcat into your living room and expecting it to follow the rules of the house. The situation will end badly and you’ll only have yourself to blame for the mess. I know all of this because I’ve been the bobcat. And every time I worked on somebody else’s project, one of two things happened: It either became my project, or those weren’t my friends anymore. Sometimes both.

I’m not some Machiavellian jerk, either. It’s just that entrepreneurs–present company included–simply aren’t meant to exist in the captivity of a corporate org chart. They belong in the wild where their scarcity issues and survivalist instincts can serve them and society in the way the circle of life intended.

Does this mean you should never work with an entrepreneur? Of course not. When I meet a real entrepreneur pushing a great idea, I’m quick to offer them sincere encouragement and assistance–often even an investment. But never a job.

It took me a long time to take this lesson to heart. Early on, I simply didn’t have the discipline to walk away when circumstances landed some corporate impresario on the job market. After all, most entrepreneurs are incredibly magnetic–which sounds great until all that magnetism inevitably starts messing with the compass of your business.

After being burned by my own kind one too many times, I now look for the equally talented, less chaos-inducing cousin of the entrepreneur: the intrapreneur. Intrapreneurs are basically entrepreneurs without the crazy gleam in their eye. They have incredible intelligence, are excellent managers of an idea, know how to smartly deploy resources, navigate set parameters, and work effectively within a defined chain of command. Most importantly, they’re out to help you build the business they were hired to join–not poach an entire department of yours to build one of their own.

Now, many intrapreneurs may very well think of themselves as entrepreneurs, which doesn’t really matter since neither is better or worse than the other on a qualitative basis. But by my strict definition, the difference is simple: intrapreneurs can thrive working for themselves OR someone else; entrepreneurs can and should ONLY work on their own ideas.

Despite my firm membership in this latter camp, I admire and envy intrapreneurs with every fiber of my being. I spend my days seeking them out and spent years of my own life trying to be one. But from college to failed gigs at friends’ companies, I frankly never finished anything that involved doing what someone else told me to. At West Point, I was deluged with the regimentation and well-honed tactics of world-famous military intrapreneurs like Pershing and Sherman; I always identified more with organization-averse outliers like Patton and MacArthur–entrepreneurs if there ever were ones. Suffice it to say, I did not graduate.

I’m not complaining about any of this, mind you. I know I’m exactly where I belong and I have the good fortune to be surrounded by a team of really smart people I deeply care about and to whom I owe the early success of the young business we’ve built together. Our company can literally never have enough people with their passion, purpose, and ingenuity.

But I’m incredibly thankful it has no more than one of me.