Your Boss is Ready to Fail, Are You? Assess Your Startup Risk Tolerance

Do you have the right risk profile for a startup?

The odds of a new business succeeding are about the same as those of a new marriage—not great. But like newlyweds, entrepreneurs aren’t deterred by the likelihood of failure.

In their minds, the risks associated with a startup are far outweighed by the rewards. Are they for you?

Fear Itself

For Jason Jacobs, founder of RunKeeper (one of my fav apps, if you must know) becoming an entrepreneur was the dream, not the specific company he founded.

When asked in an interview with Mixergy.com if he feared failure, he responded, “If I fail gloriously and this goes nowhere, I’ll be a failed entrepreneur. But at least I’ll be an entrepreneur.”

Startup Risk Assessment Question 1:

Ask yourself this—if your job, and paycheck, went away tomorrow would you think, “at least I tried?”

Failing Forward

In a SmartBrief on Entrepreneurs survey, 65 percent of entrepreneurs said they’ve failed at one or more startup. Almost 8 percent said they’d launched three to five failed startups. And in the ultimate “try, try again” example, nearly one percent said they’d failed six or more times. Ouch.

Yet most entrepreneurs don’t bemoan these defeats. Failures are viewed as such a right of passage that serial entrepreneur Steve Blank suggests entrepreneurs shouldn’t approach investors until they have a minimum of three failed business cycles under their belt.

He also defines a startup as “a temporary organization used to search for a scalable and repeatable business model.”

Startup Risk Assessment Question 2:

Ask yourself this—if you took a job at a startup, could you view it as a temporary position and move on to the next without regret?

Don't stop thinking about tomorrow. Did Fleetwood Mac know something about startups?

Misery Loves (a Startup) Company

There’s so much failing going on among startups that there’s an entire conference dedicated to it. Failcon (yes, that’s really the name) is an annual conference where entrepreneurs gather to discuss, you guessed it, failing. The goal of Failcon is to learn from each other’s mistakes and share some of your own.

Do you know any other area of life where failure is so accepted? So talked about? So celebrated?

Startup Risk Assessment Question 3:

Ask yourself this—would you consider a failed startup a success for your career?

Your entrepreneur boss is ready to fail. Are you?

If you hesitated, on any of the questions, even for an infinitesimal fraction of a nanosecond, you need to turn around and bolt. Run straight towards that corporate job.

Yes, you may be bored from time to time. No, there won’t be any hope of gloriously, ridiculously large payouts from equity stakes in the company. But you know what there will be? For you, at least. Sanity. You won’t find nonna that here.

If you answered yes to all three; a resounding, unquestionable, unshakeable hells-to-the-yes, you just might have the right fail tolerance and the right risk profile to work for a startup. Strap on your crash helmet and give it a shot.

Just don’t come crying to me if it all goes to hell in an infinitesimal fraction of a nanosecond. You’ve been warned, my friend.

[Photo credit: Watz via Flickr]