Why Great Entrepreneurs Take Big Risks & Sometimes Get Fired

I never met a great entrepreneur who was afraid of failure. Or who didn’t take over-sized risks to win big. This is why many get fired.

I spent the first 10 years of my career at A.T. Kearney, a long way from the risk taking that is Silicon Valley. Kearney, at 87, is one of the oldest consulting firms in the world. It is a tight partnership and people are rarely let go. Employees grow and develop, and some leave to become industry executives. But part of the culture is that managers shy away from firing colleagues.

I almost got fired a few times. And I probably would have been a better entrepreneur if I had. Except for some great clients, who loved my maverick nature, and a great friend and mentor, Bob Duffy, who is still a trusted advisor and close friend of the firm, I probably would not have become one of the youngest partners in the history of the firm. I might have been fired instead. I was not alone in my lack of conformity. Other Kearney people who worked for me and who now are C-level executives at some of the biggest market cap companies in the valley “transitioned out” because they did not quite fit. I see now that their passion, commitment and obsessiveness work well in the startup world. While I am glad I didn’t get fired, getting fired would have made that clearer to me years earlier.

Great entrepreneurs embody these traits better than I do. And that is why they get fired. I don’t need to list them all. But one everyone knows is Steve Jobs. I can remember sitting in a bar in the Marina with Napster co-founder Sean Parker shortly after he separated from Plaxo thinking that this guy is like Steve Jobs and at some point he is NOT going to leave and is going to change the world. Already he has. He changed it at Facebook. I guess he parted ways there, too. He is changing it again with Spotify.

In hindsight, entrepreneurs get fired because they:

• Take risks the rest of us think are nuts. If they don’t they aren’t going to win.
• See things no one else does. If everyone did, they would be doing them.
• Break the rules. Many times they don’t “get” why the rules exist in the first place.
• Are often more sure than they are right.

Most importantly, though, they get fired because they don’t care. I have never met a great entrepreneur who was afraid of failure. They have a huge need to win, something we often refer to as a “chip on the shoulder to win.” It is so important that they don’t see the cost of failure the way others do. While economic theory has shown most people fear losses more than they value gains, entrepreneurs just don’t care as much as us mere mortals about failure. This is why they win and it is also why they are let go.

If you are going to be a serial entrepreneur, you are probably going to get fired. And you certainly are going to fail. So maybe you should think about:

• Failing with grace.
• Failing though persistence, not because you give up.
• Taking ownership for failure, but not taking it personally. There is a fine line.
• Accepting the risk and being ready for it. Have a base of relationships to support you when it happens.
• Failing as a member of your team. But not failing your team.
• Leading through failure. Don’t walk away.

I am not sure I have ever technically been fired. But I have an incredible letter hanging in my home office from someone who did not “technically” fire me thanking me for my service and extolling my virtues. In other words, while I was not technically fired, I think I was. And I would not give it up for anything.

That “firing” - and other setbacks and failures I have had as an executive, entrepreneur and an investor - were great investments. Of course I hope not to repeat them. But I probably will. And they will make me a better entrepreneur.