Kevin O’Leary: Why He Favors Estrogen-Fueled Businesses

Anyone who has seen the ABC hit reality show, “Shark Tank,” would agree Kevin O’Leary comes across as a cold-hearted businessman. He doesn’t think twice about telling contestants they’re “vampire cockroaches” or “bozos” in the business of selling “crap.”

“I am the only shark that tells the truth,” O’Leary, also known as Mr. Wonderful, said in a phone interview this past Friday. “Everybody is so optimistic about what they’re worth.”

The painful truth is, no matter how calculated and diligent the Canadian mogul is, many of his “Shark Tank” businesses fail. He wrote off a quarter of them in his portfolio last year. In my conversation with him, he explained the one thing that all of his businesses have in common and what people don’t know about him.

Ho: Do you seed invest in companies or do venture capital outside of “Shark Tank?”

O’Leary: I used to. But Shark Tank is such a powerful platform that my preference is always to invest in one that has the benefit of the platform. It’s a form of free customer acquisition.

If you look at something like Wicked Good Cupcakes, which is a commodity, there are thousands of cupcake companies. But the fastest-growing cupcake company in America is Wicked Good Cupcakes. That’s the Shark Tank factor. That’s why I want to be on the Shark Tank. So my bias is fund the companies that I meet on Shark Tank and make them successful and keep their story in front of America on Shark Tank.

Ho: How many Shark Tank companies do you have?

O’Leary: O’Leary Ventures, my private company including all of the deals I’ve done, some Shark Tank, some non-Shark Tank, some private equity, has 32 companies in it.

Ho: What’s your favorite Shark Tank deal?

O’Leary: It’s like asking which is my favorite child. I have so many favorites. I am very happy with the outcome of Groovebook. We just sold to Shutterfly for $14.5 million in cash. That’s the largest exit deal in Shark Tank history.

The most successful I’ve had on an IRR (internal rate of return) basis right now is Wicked Good Cupcakes. It’s phenomenally profitable and successful. Honey Fund has been an absolute home-run hit. It’s the largest honeymoon registry in America today. That’s another Shark Tank deal. There’s many that you haven’t seen yet.

We’re halfway through season seven; there’re spectacular companies this year. Each year the quality of the companies get bigger and the better, and the deals get more complex with different structures being used. I think this season of Shark Tank is going to be a monster. There’re so many incredible tech deals, and we’re only halfway through shooting it. There are more money and more deals in Shark Tank history. We’re all very thrilled. Some of the deals are very large, multi-million dollar deals.

Ho: What is your biggest disappoint in a Shark Tank investment?

O’Leary: Obviously in venture capital, not everything works. I’ve had some failures. Toygaroo would be one of them. It, unfortunately, didn’t work out. Sometimes that happens. I got to take the winners with the losers. But I have more winners than losers, and I just drive on.

Ho: Why didn’t Toygaroo work out?

O’Leary: It’s hard to say. Sometimes, it’s market timing. Sometimes, it’s a shift in pricing. It’s better in some ways, not to focus your time on your losers. It’s better to focus on your winners because that’s where you get your returns. That’s the way I look at it.

I cry every time I lose a dollar. That’s a horrible thing. But I realize it’s just part of being in business. It’s part of being a venture capitalist.

Ho: I’m curious. Why did you like Wicked Good Cupcakes, because you always talk about having something proprietary and cupcakes are a commodity?

O’Leary: Yes. That was a test of the value of the Shark Tank platform. I did a commodity deal to find out what the value of Shark Tank is.

Here’s something else you might find interesting. At the end of each year, my auditors go through all of my companies with what’s called a “going concern” test. If they feel it’s not a going concern, they force me to write it off. Each year we have some of these. At the end of 2014 — I think we were 27 companies at that time — they took seven of them to zero. They wrote them off.

They proposed to me why don’t you do some research on the ones that returned capital because many of them have been huge hits. Some of them returned all my capital and are very profitable. I will hire some interns to do it. And we did. Here’s the stunning outcome: Not some of the companies — but all of the companies — that returned my capital and were winners were run by women. Not some. All of them.

My bias now is to figure out why some of these companies are so successful. There’s an old adage: If you want something done, give it to a busy mother. There may be some merit to that. Their time management skills, their risk management, is clearly superior.

So my bias on Shark Tank today is to invest in women.

Ho: I was really touched when you invested in the woman with the gumbo company because she was a struggling mother. 

O’Leary: Each situation is different. There’s something remarkable going on in America today. We have undervalued women CEOs dramatically. I am not talking about this on a social bias; I am talking about this in financial results. They’ve been stunning for me. The difference is incredible. So naturally, when I am offered two deals, one run by a woman, and one run by a man, my financial results tell me which direction to go, I am going to back the woman.

Ho: You’ve had so much media coverage and written books, is there anything that we don’t know about you already?

O’Leary: I was an artist actually. I was an avid photographer. I play guitar. I always wanted to make a living as a photographer. I was a film editor. I did some editing of the Olympics in 1976. I still do that work today, and I’m trying to get it going again.

My dad told me: “You’re never going to make it as a photographer. You better get a business degree.” It was the right advice. But I am going back to prove him wrong. I am going to make it as a photographer again. What I like to say is that I am a starving artist, but hold the starving.