The Diary Of A CEO with Steven Bartlett

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Monday, 30 June 2025 - 1 hour 54 minutes

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. He is the Founder of O’Leary Financial Group, Chairman of O’Shares Investments, and bestselling author of books such as, ‘Cold Hard Truth: On Family, Kids and Money’. 

He explains: 

• How to 10X your income without working harder. 

• The biggest lie about investing and what actually works. 

• The harsh truth about becoming rich. 

• The 28-rule habit that is keeping you poor.  

• The wealth rule that took Kevin from $100 to $100,000.

00:00 Intro

02:27 The Ice Cream Store That Changed My Life

04:56 Can Anyone Be an Entrepreneur?

07:09 What I Learned from Working with Steve Jobs

09:23 The Secret Recipe for Success from Elon Musk and Steve Jobs

13:21 The Importance of Having Balance in Your Life and Work

17:08 8 Out of 10 Businesses Will Fail

20:05 The Importance of Listening in Business

22:12 What Are the Attributes of Successful Entrepreneurs?

27:38 How to Grow a Business Aura

29:43 Hiring Women into Executive Roles

33:05 Successful Entrepreneurs from Shark Tank

35:56 No One Outcome Defines What You Are

37:32 Steve Jobs Changed My Life

41:58 The Second Most Important Step to Success

43:36 The Different Types of Leadership

46:47 How to Find Great People for Your Business

47:49 People with Balanced Lives and Diverse Interests Tend to Be More Successful

49:14 Your Personal Relationship with Money

51:53 The Power of Investing Long Term

55:52 Don’t Outspend What You Earn

56:50 Small Financial Mistakes People Make

59:34 Why Do You Wear Two Watches?

59:59 Invest in Dividend Stocks

01:01:42 Are You Bullish on Crypto?

01:04:17 Why You Shouldn’t Buy a House

01:09:21 How Much Your Relationship Impacts Your Finances

01:13:52 The Shocking Link Between Money and Divorce

01:16:40 The 5 Love Languages of Money

01:19:56 The Role of Artificial Intelligence in Your Finances

01:26:56 AI, Welfare and Wars

01:27:48 Is Apple Dying?

01:33:52 Was Steve Jobs Happy?

01:38:23 Are You Happy?

01:45:04 Turning Down Offers That Aren’t Authentic to You

Follow Kevin:

Instagram - https://bit.ly/4kdu3Ai 

X - https://bit.ly/44kRa61 

YouTube - https://bit.ly/4kfyGK5

You can purchase Kevin’s book, ‘Cold Hard Truth: On Family, Kids and Money’, here: https://bit.ly/4lryWqA 

Get your hands on the Diary Of A CEO Conversation Cards here: https://bit.ly/conversationcards-mp  

Get email updates: https://bit.ly/diary-of-a-ceo-yt 

Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb 

Sponsors:

Shopify - https://shopify.com/bartlett   
JustWorks - http://JustWorks.com 

Learn more about your ad choices. Visit megaphone.fm/adchoices

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