The Diary Of A CEO with Steven Bartlett Kevin O'Leary: This Daily Habit Is Keeping You Poor. Here's What You Should Do Every Time You Get Paid!
Jun 30, 2025
01:52:39
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
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theexperienceplus.substack.com
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
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theexperienceplus.substack.com