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Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid! artwork

Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid!

The Diary Of A CEO with Steven Bartlett

June 30, 2025

Is this 1 money habit secretly keeping you poor? Shark Tank’s Kevin O’Leary reveals the brutal truth about wealth, business, and getting rich, and what you must change to build real financial freedom. Kevin O’Leary is a Canadian entrepreneur and investor, also known as ‘Mr Wonderful’ on Shark Tank.

Speakers Kevin O'Leary, Steven Bartlett

TopicsBusinessSociety & Culture

Kevin O'Leary (0:00)

Hey guys, it's Selena Gomez. I'm so excited for you to try my new signature Oreo cookie with chocolate and cinnamon flavored cream.

Steven Bartlett (0:09)

Pick it up in stores now.

Kevin O'Leary (0:11)

Pick up a pack of Selena Gomez Oreo cookies at participating Walmart stores. Experience it while it lasts. That is the stupidest thing you can ever do.

Steven Bartlett (0:21)

What is the most important thing for someone who's just trying to grow their money?

Kevin O'Leary (0:24)

So I learned this from my mother and I actually built a whole company around it. Yeah, there she is. So... I haven't seen that picture in a while.

Steven Bartlett (0:42)

Damn.

Kevin O'Leary (0:43)

I mean, what she did, the performance was extraordinary. And with that, she put my brother and I through college. She took care of her family when they fell on hard times. When I saw the results, I said, that's it. That's how I'm going to invest for the rest of my life.

Steven Bartlett (0:57)

So talk me through this. I want as much detail as possible.

Kevin O'Leary (1:00)

Let's start with this.

SPEAKER_3 (1:01)

Kevin O'Leary, aka Mr. Wonderful, is the self-made millionaire and investor who's built and sold companies for billions.

Kevin O'Leary (1:09)

There's a lot of people don't like me for my bloodness. I don't care because there's people that don't think ahead and find themselves mired in debt, but then pissing away money, spending $28 for lunch. I mean, that's just stupid.

Steven Bartlett (1:20)

What about the house?

Kevin O'Leary (1:21)

The mistake that people make is they buy too much house. Never let the mortgage and the cost of maintaining the house be more than one-third of your income.

Steven Bartlett (1:30)

Now, how much does the person that you fall in love with have an impact?

Kevin O'Leary (1:33)

You kidding? It's everything. And I did some research, and most marriages can survive infidelity. They can't survive financial stress. But if everybody that's listening does this one thing, you will have over a million and a half dollars.

Steven Bartlett (1:46)

Kevin, can anybody be an entrepreneur?

Kevin O'Leary (1:48)

No. Only a third of people can become successful entrepreneurs because there's a couple of things that you must achieve to be successful. First...

Steven Bartlett (1:58)

Quick one before we get back to this episode. Just give me 30 seconds of your time. Two things I wanted to say. The first thing is a huge thank you for listening and tuning in to the show week after week. It means the world to all of us and this really is a dream that we absolutely never had and couldn't have imagined getting to this place. But secondly, it's a dream where we feel like we're only just getting started. And if you enjoy what we do here, please join the 24% of people that listen to this podcast regularly and follow us on this app. Here's a promise I'm going to make to you. I'm going to do everything in my power to make this show as good as I can now and into the future. We're going to deliver the guests that you want me to speak to and we're going to continue to keep doing all of the things you love about this show.

Kevin, I'm going to ask you to do something which is quite difficult because I'd find it quite hard if someone asked me to do this. But before we get into the detail, can you give me a 30,000 foot view on your entrepreneurship and investing career? Just the three bullet points that are most pertinent before we dig into those specifics.

Kevin O'Leary (3:03)

Every entrepreneur I've ever talked to that finds himself where I am today has a defining moment where they are pushed into this path. It's something they can remember, and they remember it in perpetuity. And I'll remember my moment getting fired in an ice cream store. That's simple. First day on the job, asked to serve and scoop ice cream, and I did that all day. But when people sample ice cream, they get a taster and they take their gum out and they throw it on the floor. Somebody's got to scrape the gum off the floor at the end of the day. I only took that job because I was very interested in the girl who was working the shoe store, and I figured I could hang out with her afterwards. And I saw her waiting for me, and the woman who owned the store said, you've got to scrape the gum off the floor. And I didn't want her to see me on my knees with a scraper. It was bad for my brand. I was in high school. And she said, no, no, you have to do it. And I said, you hired me as a scooper, not a scraper. She said, how about you're fired? And I didn't know what that meant. And it was the defining moment for me because I realized there's two kinds of people in the world. There's people that own the store, and there's people that scrape the shit off the floor. And you have to decide who you are. And I'm not saying being an employee is a bad thing. Not at all. But for me, it hit me. It just hit me.

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