If you're at all familiar with the hit TV show, Shark Tank, then you are surely familiar with one of its star guests: Kevin O'Leary.

Businessman, investor, writer, financial commentator, television personality--these are just a few of the ways this Canadian entrepreneur is described. But there is another side to 'Mr. Wonderful' that doesn't get discussed nearly enough: the artist.

I was fortunate to have the opportunity to interview Kevin O'Leary. However, before we talked, I spent a considerable amount of time reading up on his work and getting a firm sense of all that he's done. And with such an impressive portfolio, it amazed me how lopsided the content out there was, heavily leaning toward his accomplishments in the world of business with little focus on the creative interests, pursuits, and habits that may have gotten him there in the first place.

It was a compliment for O'Leary to start our interview by saying, "This is an angle I don't think I've done before."

My question was simple:

How does someone who is both business minded and creatively inclined balance those two worlds? What role does art play in business, and vice versa?

"When you think of the binary aspects of finance, business, and investing, it's very black and white. It's scientific--you either make money or you lose it. So when you're making the decisions of risk versus return, in every deal you make, what you need is a little art versus science. I am a big believer in balancing yin/yang. And I believe when you can approach these kinds of decisions from the perspective, chaos, and random outcome of art and music, that's what makes you a better leader and investor. Because what makes a photograph great? You can say what makes an investment great: a 50% return. But you can't say that about a photograph. It's subjective. It's in the eye of the beholder. And that goes for seeing opportunities in business as well," said O'Leary.

To gain a better understanding of how O'Leary actually integrated this way of thinking into his journey, we went back to the beginning of his story his first big company, SoftKey.

My intention here was to see first-hand how O'Leary balanced building a company and working 18 hours a day with still making time for his creative outlets. His answer, of course, was that balance isn't found through separation--business over here, creativity over there.

Balance is found through integration.

"I've never told this story, but this is how it all started. I was working full-time as an 8 plate Steenbeck editor. That was how you edited film back in the early 80s. And my first company, I was the cameraman/producer/editor of the work we were doing covering hockey for the networks. Saturday night hockey was always a huge event, and they wanted to do vignettes on the big players. So I'd have 4 days to shoot it with my team, process the film, record the music, and cut it on an 8 Plate Steenbeck, put in the graphics and titles, and then send it up to a satellite by Saturday morning so it could be beamed down to the network. That may sound easy, but it was very hard to do. Now here's where the business started from the art...

One of the biggest challenges back then was making the titles. So if you put up a photo of Bobby Orr, you'd want it to say Bobby Orr underneath for 2-3 seconds. This was done with very primitive technology back then. And one night I was at a computer club at a library, and I met a man named John Freeman who was an oil engineer and executive. And he'd designed a software product that ran a two pin plotter made by Hewlett Packard. There were no ink jet printers in 1980. The way you did color or any kind of graphic was you did an X/Y plot on a Hewlett Packard plotter made in San Diego. And his software was so eloquent that I could make my own by just typing in Bobby Orr, and then in two minutes the pens would draw the title. I could then shoot it with a camera and save myself hours. So when I saw how well that solution worked, I thought it was so fantastic that it could sell hundreds of thousands of plotters all around the world. So I got on a plane and flew to meet with the executives from Hewlett Packard and I showed them. And that was the beginning of my very first software deal. I went back and forth from San Diego basically in 48 hours, convinced them, and we had our first million dollar sale--while I was still editing film. So it was the solution to a problem that I had as an artist, that was the beginning of SoftKey, which was the predecessor to The Learning Company. But it was the crossover between art and science and business that created the solution."

O'Leary's story is, if anything, consolation for artists and entrepreneurs alike. Often times, we see creativity and business as separate--oil and water. But the truth is, they are not.

In fact, it's right where they intersect that the magic happens.

Published on: Dec 12, 2016
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