Erin McCoy and Kevin O'Leary Muskoka boat ride discussing philanthropy

I'm here with my great friend Kevin O'Leary, and we are in the beautiful Muskoka on Lake Joseph. We're going for a little boat cruise now. Kevin, you and I have a lot in common, and one thing in particular is about educating people on money, especially women and children. Making sure that you can be financially successful in the future — so tell us more about your books.

You know the genesis of the whole book thing? Because I'm now in my third one, it happened this way: I get about 10,000 emails a month; I can't read them all. I pull a hundred of them in the last week just to get the tonality of what people are thinking.

So, you actually do answer back to people?

Oh yeah!

And what's that?

Sometimes we put them on the air, like in the area with the answers that are particularly good questions. What I started doing is I noticed that there were the same 50 questions being asked of me year in, year out. So, I wrote them all down. I said, "Okay, I'm gonna answer these 50 questions, because I get them every year anyways." And that was the beginning of the first book.

What happens is I sit down at night at 11 o'clock with a bottle of Burgundy, drink the whole thing by one... probably one of yours, craft of course. And then I write, and I read it and I say, "This stuff is great." Then I wake up in the morning, look at it again, and say, "This stuff is so..." Writing a book was really hard work, the first one, but I got better at it. Good therapy?

Yeah, it was. But I answer those questions from the real life experience that I've had. I've made many of those mistakes myself; I don't make them anymore. I'm all about financial literacy now because I realized at the age of five is when you should start teaching children about money — three, five years old. I've got a whole bunch of points on how to do that. I've done it with my own kids; they understand the value of money. You know, I'm not gonna be giving them any of it when they graduate, so they know they've got a tough life to make their way. But I'm gonna pay for them till then; that's what my parents did with me.

At the end of the day, financial literacy is what I write about. And I care what age you are; you can always learn something about how to be better in your relationship with money because it sits at the table with you. To me, a family is like a business; you're building a dynasty together. That's what a family is, and money is right there beside you. Without it, you have a very hard time with everything that you do.

I think it's very important that you give back, and you do your part. So maybe you can tell our viewers what it is that you do.

You know, what I've realized is for the last, I don't know, 20 years I’ve been giving to all kinds of different causes: hospitals, universities, charities, ballets... you name it. And I think what happened to me in the last couple of years is I started looking at it, saying, "How do I know this money that I'm giving away every year is being properly used?" So what I've decided to do is create my own foundation.

So here's hitting the genesis of how it happened: I'm a huge advocate for teenage entrepreneurs. I think there are people in life that know, when they're in grade 10, 11, and 12, they know their destiny is to take a risk and start a business, and I want to be there to support them. I haven't heard of anybody doing it, so that’s the focus of my work.

And here's how it started: last year Maclean's magazine did an article on me and they included a photo I took in 1970 because I've been a photographer for 40 years — another passion. Yeah, I love it; it's a great hobby, and I've enjoyed it as I've traveled the world doing television and investing globally with O'Leary Funds. I always have a camera with me; I've got 68,000 images from the go back decades.

They picked this one image and published it of an airplane at a show years and years ago, and all of a sudden a gallery in Vancouver called up the author and said, "We'd like to sell that in our gallery." And it got me thinking. So, I just sat down with my partners at the CBC and Brookfield, who is a very big man from the gallery downtown, and where’s Kenny in place? I said, "Listen, I'm going to ask all the Corbett, who I met shooting Redemption II, another show. She was on one of the cast members and she's probably one of the world's greatest curators of photography. She's about to open her own gallery."

So, I had a meeting with her and said, "Flo, look at this work. All of them... can you pick 25 images or help me choose 25, and we'll do a photo show?" Brookfield gave up the space for free, the CBC is gonna promote it. We're gonna sell the prints for $6,000 each — they're archival, built by Charles Chu, they're printed, and then the Gilder, which is legendary in making frames, is going to make these artisan handmade frames.

We’ve sold our first three to a corporation this morning. I can't give their name out because there's a house and it wasn't over. Yep, we're still getting the Intel, though. I know, I'm very excited about it because we're gonna launch this and make it public on October 8th. We're gonna have a huge show at a reception at the gallery, and then we'll start selling the prints.

All of the profits from that endeavor go to teenage entrepreneurs, so I hope we do millions in sales, and we're gonna take the show to every Canadian city and major cities in the United States over the next three years. That's my big initiative in philanthropy, and I'm very excited about it because it hits right where I care: teenage entrepreneurs.

So, if you're a teenage entrepreneur out there and you want $25,000 from me, go to the CBC website and enter. You have to have your teacher enter you. Then you have to put a three-minute video up there, and everybody can vote. I'm gonna take one boy, one girl every year, and they can do whatever they want with that $25,000, and we're just gonna grow it from there.

So, we'll make sure that we tweet that out and put that on our Facebook as well and push that out. It would be great, and as soon as the CBC is ready and they turn that site on, I'm gonna be asking everybody to push traffic there, so it'll be great.

Well, Kevin, I'm a huge fan! You have been very successful, but I think you've done it; you've made your mistakes, as you admit. But now what you're trying to do is you're helping everybody else not to make those same mistakes. The fact that you take the time to give back and every opportunity — think of a way in which you can do that — it says an awful lot about you.

Well, thank you! I really appreciate that. And what you do in real estate is probably, in all the asset classes, the most important. In this sense, people buy real estate with debt, and if they do it right, it can be a fantastic experience. But if they get it wrong, it can wipe them out.

So, understanding real estate and mortgages and debt, and maintaining yourself with that is paramount. It is the most important thing anybody can work on. So, I applaud you for that work you're doing, and I think if you keep that theme of financial literacy going, you can't go wrong because most Canadians have the majority of their wealth in their home.

So, I think you and I can cause lots of trouble. I can't wait to do that, along with producer Jake, there, that's holding that camera. So, I think at this particular point in time, we need to go back and have some fun at your place. Let's go open up some fantastical Larry wine! I have just the bottle for you guys.

Well, toast to this gorgeous day and all the real estate on this lake! And by the way, I don't think there's any mortgages here. Alright, you!