Fight to the finish

I find that anyone who isn’t an entrepreneur often has a rosy-tinted impression of what it means to be in business. They seem to think you’re instantly rich, with tons of free time on your hands, and that “writing off” expenses somehow means you don’t have to pay for them.

If only!

The most appropriate analogy that I can think of to describe what it means to be an entrepreneur is fictitious boxing underdog Rocky Balboa. Not the victorious heavyweight champion of the world, but the bloodied and battered punch bag who was pulpified by Apollo Creed.

Small business owners are a lot like Rocky. They enter the ring with the same heart-pounding trepidation, dreaming of the big win but often naively under-prepped for what’s in store. Their quest for the title usually starts with an idea: a eureka-moment vision of being their own boss and setting their own hours, of making some money and building a legacy. Taking the giant leap from dreamer to scrapper might be forced upon them by changes in their health or work status, or it might be from a long-fought realization that there’s just no escaping the call to self-employment… but once they make that jump, they’re all in. That’s when the pounding begins.

Being a small business owner means you’re going to get knocked down and out with depressing regularity. But like Sylvester Stallone’s famous big-screen persona, entrepreneurs keep coming back for more.

They fight to be top-of-mind with clients who seem to think of them only when it’s to request a donation. They do constant battle with 14-hour days, knowing that failure comes without a social safety net. They combat paperwork and regulations and taxes and underground competitors. Yes, being a small business owner means you’re going to get knocked down and out with depressing regularity. But like Sylvester Stallone’s famous big-screen persona, entrepreneurs keep coming back for more. Apparently, a masochist by any other name is…

Which begs the question: why in the name of all that’s holy would anyone sign up for that? You’ll find a couple of answers in our story about serial entrepreneurs (“For the love of the game”). We talked to a number of people who are seriously addicted to startups. Some of them were contenders from the ring of the bell; others used their smack downs as training to tackle bigger and better opponents. All of them are fighters.

Former occupational therapist turned photographer/ online retailer/techpreneur Kelly Lawson likens her venturesome spirit to a crow-like attraction for shiny new things. “I see an opportunity… and I feel compelled to chase after it—to feel the outcome.” Tom Hickey estimates he’s founded a whopping 23 companies in his career to date (one of which he sold for $87 million)—and he’s still a few years shy of his 50th birthday. His passion, he says, is figuring out how things work. Once he has that under his belt, he’s ready to move on to the next challenge.

Shelley Simpson, now on her third private enterprise, says exit strategies are essential to defending your entrepreneurial title. While you have to be persistent in jabbing away at every opening, she says you also have to recognize where the opportunity ends.

Gordon Stevens has launched seven new businesses since walking away from an executive position with Goldman Sachs about 15 years ago and five of them are still in operation (an impressive 71 per cent success rate). He could have let those two failed enterprises dampen his entrepreneurial spirit, but he didn’t. Stevens, like thousands of others like him throughout Atlantic Canada, is a true contender.

To quote the Italian Stallion himself, “It ain’t how hard you hit; it’s about how hard you can get hit, and keep moving forward. That’s how winning is done.” Small businesses are our economic champions. This issue is about giving them the respect and recognition they deserve.