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What Does It Mean to be Crazy as an Entrepreneur?

Are all entrepreneurs crazy?  If so, what kind of crazy?

Wellspring Software started 25 years ago by brothers, Stu and Greg Neale.  At the time they were routinely told they were crazy.  “This is your third business in nearly five years, are you crazy?”  “You each have multiple kids, you’re crazy to start a business now,” Stu remembers people telling them.

So were they?  “Yeah, probably a little,” Stu says.  “Then again, for us it would have been crazy not to be in business for ourselves.”  So is crazy simply a matter of perspective?

MBA professors will tell you that the idea that some people are born entrepreneurs or that you have to be a little crazy to be one, is a farce.  Through financial risk mitigation techniques and sound business planning, they’ll explain, you can take the crazy out of entrepreneurism.  But can you ever remove all the risk that startups bring?  Can starting a business ever be as stable as joining an established company?

Simply answered, no.  If it were, there would be a lot more new businesses in the world.  What these MBA professors don’t address are the psychological risks, be them perceived or otherwise, that contribute to the notion that startups are precarious business ventures.  Linda Rottenberg, the CEO and co-founder of the global non-profit Endeavor, says, “It’s not an absence of ideas or business techniques, it’s the absences of courage to actually be willing to put yourself on the line and maybe even be called crazy.”

For some, like Stu and Greg, this willingness to be called crazy was second nature.  They had been developing businesses since they were in junior high in Cleveland going door to door in their neighborhood offering snow shovel services.  Is every kid willing to go door to door offering services?  “Fortunately not, or else we might not have had a good business.”

This same craziness was behind the Neale and Peter Paint Company and the Neale Tree Eradication Services they operated in high school and college.  As they got older the products and services became more refined with mopeds in the 70’s, car clocks in the 80’s, and eventually accounting software in the 90’s through today.  But that craziness, that willingness to put themselves on the line, did that ever change?  “No, that was probably the one thing that endured from business to business.  We always thought our ideas were gold, even if in hindsight they weren’t, and we were willing to push them.”

Are all entrepreneurs crazy?  Yeah, probably a little.  But it’s a good crazy, a courageous crazy that allows them to face both financial and psychological risks and move forward anyway.  For Stu, being a little crazy, being willing to put himself on the line has worked, “Wellspring Software has been around for 25 years now, so we’re hardly a startup any more…but that doesn’t mean we’ve lost our crazy.”