The Unstoppable Kevin O’Leary: From Shark Tank to Rockstar

Most people know Kevin O’Leary as the dark suit wearing, deal making shark from ABC’s massively successful reality series, Shark Tank. “But wait, there’s more.” And in fact, there is a lot more to the Canadian businessman than meets the eye.  

I recently sat down and had a conversation with O’Leary about his rise to fame. I was particularly fascinated by— how he has been able to build such a memorable personal brand, a wonderful new project he is working on and some of the important lessons from his successes (and failures) that he has learned along the way.

If you think you have any idea of what it takes to build a multi-billion dollar empire, you may want to think again.

Here’s what I learned from my conversation with O’Leary:

1. You must have a yin and a yang.

One of the first things that immediately struck me about O’Leary is that he has mastered the seemingly impossible work-life balance.

I know, who would have thought? As much as his character on Shark Tank might seem like he does nothing other than day-dream of cash, deals and royalties, my impression of O’Leary is far different.

“I think business is great if you have a yin and yang,” said O’Leary.

In his case, business and investing are his yang, and photography and music are his yin. In fact, he is currently working on his first album

O’Leary continued, “Business has the discipline of binary (you’re either making money or you’re not). Art and music are chaos. There’s no binary on or off. There is no good or bad music. It’s really what you personally enjoy.”

2. You have to be honest all the time.

I was deeply fascinated by how O’Leary has been able to build such a well known and memorable personal brand. Everyone knows who he is.

He may seem like a tough guy on TV, and he is, but his brutally honest style means he always tells it like it is.

“What I’ve learned in the process  is you have to be honest all the time, even though the news isn’t necessarily good—particularly when you’re investing in a platform of multiple businesses,”  O’Leary said.

O’Leary went on to say, “What you tend to want to do (which is a mistake) is always tell a story where the sun is shining and not fess up to the fact that investing in businesses sometimes leads to failure.”


3. Always diversify when you invest.

Speaking of things not always working, it’s extremely important to diversify when you invest. O’Leary learned this from his mother decades ago. The second rule below I particularly resonate with.

O’Leary had this to say about investing, “Number one is I never own more than 5% of any one position in the portfolio. This is a rule about diversification. It’s the only free lunch in investing. I don’t care where you want to apply it, it holds true.”

O’Leary continued, “Number two, I never spend the principle; I only spend the interest or dividend.”

4. Don’t be afraid to be tough in business.

I know a lot of tough business people like O’Leary who are actually very nice people. Being tough in business doesn’t mean you aren’t a nice person, or have to lie or exaggerate. In fact, being brutally honest seems to be working quite well for the man who earned the nickname “Mr. Wonderful” on Shark Tank.

“Early on, I decided that I would just simply tell it like it is. It got me a bit of a reputation as a tough guy, but in business, my attitude is binary—you either make money or you lose it—so being honest is more important than trying to hide away your failures,” O’Leary said.

O’Leary continued, “I think that resonates with entrepreneurs; they appreciate the truth, because not all ideas are destined to work, and you have to be honest about telling them why you think they’re not. I’m OK with that space. I’m sitting in the Shark Tank sometimes and somebody is crying in front of me… I don’t care, because if you can’t deal with me in there, wait until the real world gets ahold of you. It’s just going to rip you to pieces. Business is hard, and that’s my message.”

5. Entrepreneurs must be willing to sacrifice.

If you think that you can do it all at once, you are sadly mistaken. Focus and sacrifice is the name of the game. Look at O’Leary, who sought out to be a Rockstar and photographer, ended up being a wildly successful entrepreneur and investor, and now is back to pursuing his music career.

It is possible to achieve all your dreams, but you have to sacrifice and focus when great opportunities present themselves.

“An entrepreneur is someone that is willing to sacrifice, because the truth about being an entrepreneur is it’s a tremendous personal sacrifice. The idea that your life is balanced is bullshit,” said O’Leary.

In O’Leary’s case, he may not have reached massive success if he had been stubborn and not put his music on hold while his business career was taking off.

Remember that life is a puzzle that may not be completed in the order you wish. O’Leary’s business career has enabled him the luxury and freedom to be whatever he wants. And now he can live out that childhood dream of being a Rockstar, and I assure you, nobody is going to be able to stop him.

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