Why Great Entrepreneurs Take Big Risks And 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 85, 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 at the firm and has been there since I was in kindergarten, 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.
(Ben T. Smith IV is a serial entrepreneur, investor and a co-founder of MerchantCircle.com and Spoke.com. Follow him on Twitter at @bentsmithfour)



Jonathan T. Kaplan said on November 14, 2011
As a patent attorney who works with start-up companies all the time, I have to say that I wholeheartedly agree with what Ben says. Ben seems to have done a wonderful job at capturing the entrepreneur personality.
Yori said on November 14, 2011
Phew… Now I do not feel so bad anymore about being fired from my first two jobs — the bartender job of my college years, and my first R&D job as programmer
The only caveat I would add to Ben’s essay is that a good entrepreneur should be able to tell that when something is gray, big, has large ears and a trunk and smells like an elephant, there is a good chance it is indeed an elephant. In other words “Failing through persistence” might be good learning, but “Failing through delusion” is bad.
Jack Herrick said on November 14, 2011
One of the reasons I have not accepted venture capital money at wikiHow is that I wanted the freedom to go in directions that most venture capitalists wouldn’t want to travel. If I had taken venture capital funds, I’m pretty sure I would have been fired in wikiHow’s early years when it looked like we were failing miserably.
Sean Conway said on November 14, 2011
Excellent post! I think you are right on in this post. As an entrepreneur I see many insignificant purposeless rules as business opportunities. The reward of winning is outweighed by the chance of possible loosing 10 times in a row. Sometimes getting fired I see as a win, it means you shook up the organization or the train of thought to an extent where it changed peoples outlook in the organization. Many times that is needed in large organizations
Christopher said on November 14, 2011
Great post Ben. I agreed with a lot of what you said, and blogged about it at ScratchPaperblog.com, but I dissented a little around the question of taking big risks. I think, as I explained in my post, that great entrepreneurs take carefully calculated risks. They look bold and wild from the outside, but they are not as risky as they seem. Be curious to see what you think of my conclusions – feel free to leave a comment there, whether you agree or disagree.
Jonathan L. Gal said on November 14, 2011
During these days of risk aversion, it seems that risk taking and failure are career killers. I am a serial entrepreneur with some big risks, big failures, and some firings in my background. At age 45, I am trying to figure out my next step forward, but the culture these days doesn’t seem friendly to this “entrepreneurial background” of mine.
Jonathan L. Gal said on November 14, 2011
And, trying to work from home with 4 small children is driving me nuts, to boot!
Jonathan L. Gal said on November 14, 2011
And, trying to work from home with 4 small children is driving me nuts.
Bill Waters said on November 15, 2011
I’m curious to know, Ben, how you manage some of your investments knowing what it takes to be hugely successful? In our area, Waterloo, Ontario (home of RIM and a number of tech startups – 164 in the last year alone), we have a healthy pool of small to midsized investors, and a couple of very large ones. In building my company from nothing in 1999, I saw an opportunity to expand internationally in 2005. For that I needed capital. I took on one of the largest investors in town who, after becoming fully invested, got nervous on the ‘risk’ and changed the rules. I was tossed from the company. I proceeded to start from scratch again. In two years, with no investor, I started a new company doing the same thing and surpassed the original company in revenues. I have spun off a division (valued at $7.5 million within 10 months), working on another (gaining contracts with the largest retailers in the Country within 6 months) and have a good foundation of custom development contracts.
I agree with what you are saying, but as an entrepreneur, the challenge is in finding key partners who are entrepreneurs themselves and who can relish the journey. You can mitigate the risks of failure by ensuring your partners, companies, bosses have the heart (I was going to say something else there) to be successful. Hard to find though.
Kevin Cornel said on November 15, 2011
I agree with everything except the comment about not caring about getting fired. Getting fired means you have come to an end of that journey and must now find another path to follow. Perhaps, like Bill Water above, it is a better version of the same path, but like Sisyphus you must begin again pushing that heavy rock up the hill. Having started four companies and been fired from a few corporate roles in between I can attest. An entrepreneur cares about being fired, being told that quest has ended, and facing the need to find the ‘next big thing’.
michele ruiz said on November 16, 2011
As a Latina Entrepreneur, I can totally relate. Great post. Thanks!
Darren Stahl said on November 16, 2011
However, it does not follow that everyone who takes unreasonable risks, breaks rules, cannot follow direction, and gets fired, is going to be a great entrepreneur. There are lots of entrepreneur wannabes who dress in black, act quirky, use lots of buzz words and occassionally become unreasonable, because they think that’s how successful entrepreneurs act.
Grumpy Loser said on November 18, 2011
This is the biggest load of crap. It’s not the size of the risk, it’s the size of the win that defines the greatness. Otherwise we have sites dedicated to all the big risk taking losers or to all the small dry cleaning business owners that risked everything to come to the US and build a better life for their family.
Richard Roberts said on November 18, 2011
I spent a lot of years looking for the one big hit that was going to be the work at home and live the good life answer. I took a lot of risks and ultimately lost as big as I risked. I could have blamed to economy, the political climate, or the weather. I finally realized that it was possible that the BIG thing wasn’t my thing. But, rather than give up, I just tried doing several small things and adding them up, it turned out to be no less in it’s value, and in many ways more, than what that ONE big thing might have been.
Reinout Schotman said on November 21, 2011
Good point. This is the classic risk-reward discussion applied to career development.
1) Bigco’s, especially publicly listed ones, want predictability, therefore they thrive on people who deliver predictable results. Low risk, therefore low reward.
2) Entrepreneurs thrive on uncertainty, because it is there where they see opportunities. Therefore they are for high risk, high rewards.
People in 1) outnumber those in 2), but what people in 2) must remember is that people in 1) constantly fail. They fail in seeing the opportunity. Every day. And that’s why when they get fired they need social security.
RichardGroves said on November 21, 2011
An interesting post that definitely gives a different side to be being fired. The main point I belive Ben is trying to make is that by being fired you can reflect on your current experience and understand how to move forward. If he hadn’t been fired he wouldn’t have improved, whether that is in a certain field or relaising you were in the wrong field/industry/job position.
John (TentBlogger) said on November 22, 2011
LOL. love this.
i can vouch for this. personally.