Article first published as Why A Prominent Start-up Executive Wants You to Get Fired and Fail on Technorati.

Kim Kovaks, Founder and CEO OptionEase, recently spoke to a class of emerging entrepreneurs at UC Santa Barbara. With over 700 customers, OptionEase has become the leading enterprise class SaaS solution for stock option and equity compensation tracking and compliance. Kim shocked some of the students by telling them that she hopes they fail.

In this 8-minute video excerpt from her talk, Kim describes why, "failure is my favorite word at my company now." Kim also discusses the importance of focus and why she does not hesitate to hire people who have previously been fired.

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You can watch Kim's talk below or on YouTube here:


The video begins with Kim describing her experience speaking at an Inc. 5000 conference. One of the primary messages she conveyed to the Inc. attendees was the importance of focus, especially during a startup's early days.

"There are a lot of things that entrepreneurs need to do. Yes, you need to be dedicated. Yes, you need to have that entrepreneurial spirit and you've got to stay up late…but people lose sight of the fact that they (have to) stay hyper-focused. You have to stay on focus because, as an entrepreneur, you are going to get ideas coming at you every second. We encourage it…but it doesn't mean you have to act upon (each idea). You never want to close your ears off, but you also want to be sure to remain on focus."

Failure Is A Winning Strategy


"People are so concerned about being successful all the time that sometimes they take shortcuts to be successful. I had a salesperson who would basically do anything with the client to get the deal. It was killing our company…she always had to sell something that didn't exist. She couldn't sell what we had.

(I told her) you've got to fail. You are going to lose deals. You're going to fail and you're going to learn how to overcome those failures with the next deal and sell what we have, not what we're going to have in six-months. I am telling everybody (at my company) 'It's OK to fail.'


"If (Roger Bannister) had run a four-minute mile the first time out of the gate, would he have run for nine-years? Probably not. He might not have recognized that it was the wind behind his back, that it was the training he was on, the shoes he was in, he may not have had an opportunity to test all those failure points.

If you ask someone who just got lucky how they (succeeded), they're like, 'I don't know.' They don't know because they never had a chance to fail."

Healthy startup cultures do not penalize employees for making mistakes because they know that the only employees who never make mistakes are those who never do anything. Unlike Big Dumb Companies, successful startups must focus on achieving results and cannot afford to expend energy affixing blame. Such environments encourage employees to internalize and take ownership of their missteps, which helps them avoid repeating them.

Getting Fired

Kim told the UC Santa Barbara student entrepreneurs that they should never fear being fired from their jobs. According to Kim, "You're not pushing the limits (if you are not afraid of getting fired). People in larger companies are reluctant to have you in their face about stuff."

Kim went on to note that employees with stock options should aggressively question their bosses because they are essentially investors in their startups. As Kim puts it, "I really went right up to the edge and had I been in bigger companies, I would have been canned, for sure. People would say, 'Why is she asking these questions?' and I would always come back and say, 'Because I am an investor in this company.'"

For employees who are fired, Kim counsels them to not despair. Rather, she encourages them to, "…think about why (they were fired). Was it the right place? Were they not receptive to you or was it just time? Sometime I have (hired) the best employees who were canned somewhere else and the reason they were canned is because they were way out-thinking the prior company. Push the envelope. At some point you've got to … be willing to take the risk."

As Kim's talk makes clear, startups should embrace failure, focus and previously fired employees. In an intellectually honest environment, more insights are gained by dissecting why a decision was wrong, than by ignoring mistakes, blaming others and taking shortcuts to achieve short-term success.

Image courtesy of Atom Smasher

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