Today, Kevin O'Leary is known as a personal finance expert: He's an investor on ABC's "Shark Tank," the chairman of ETF company O'Shares Investments, and the author of three best-selling books about money.
But even O'Leary has made a few poor money decisions while discovering the finance lessons that later built his career. O'Leary sat down with CNBC Make It to discuss his most embarrassing mistakes, what he learned from them and other money confessions.
CNBC Make It: What is your first money memory?
Kevin O'Leary: I was born dreaming about money. I came out of the womb thinking "cash flow"; that's exactly what happened. It's been on my mind since my first breath. And that's the way it should be for everybody: Money is your friend from the day you are born to the day you die.
Who taught you about money?
You know who taught me about money? My mother. She was always thinking about it too, she was always wanting to make sure she had enough for herself and she wanted financial independence, and from the age of 5 years old she talked to me about that. "Never spend the principal, only the interest," [she said].
What was your first job?
My first job was at an ice cream parlor. I worked there for a day and I got fired, and that's when I learned that there are two types of people: There are people that own the store, and people that scrape the s--- off the floor. You have to decide which one you are.
How much was your first allowance?
You know, inflation has played a role in this. My first allowance was 50 cents a week, and I realized boy this sucks. I need more.
What is the cheapest thing that brings you joy?
Breathing. I like being alive.
What is the most fun you've ever had spending money?
One day, I just decided that I wanted to have a Porsche. I drove it home, my wife happened to be in the back yard when I was pulling up. She looked at me, and she said, "Oh no, another bald a------ in a Porsche." Her exact words. Every time I pull that car out today, she says the same thing. I don't care, I like the car.
What is the most embarrassing purchase you've ever made?
I think I was in Houston, Texas and I don't know, I had a couple of hours free, and I said to my driver, "Take me to where they make the most elegant, exotic cowboy boots in this town." That evening I was going to make a speech about investing and I thought, "Everybody will be wearing cowboy boots, I'm in Houston!" So instead of putting on my black shoes, I bought these crazy boots made out of snakeskin and all kinds of feathers on them and a little bell on the top. I walked out on stage and everybody looked at me in horror. I looked like a real dork. I still have those boots. I never wear them and they cost a freakin' fortune.
What is money?
Money is freedom. That's what money is.
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Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."