Why Most Deals Fail with Shark Tank's Kevin O'Leary
The Home Service Expert Podcast
Tommy Mello
4.8 • 705 Ratings
🗓️ 8 December 2025
⏱️ 46 minutes
🧾️ Download transcript
Summary
Kevin O'Leary is a seasoned entrepreneur, investor, and television personality best known as "Mr. Wonderful" on Shark Tank. Before he became "Mr. Wonderful," he was building software companies and collaborating with innovators like Steve Jobs — experiences that sharpened his belief that clarity, product focus, and disciplined execution separate real businesses from the noise.
After selling his first company in one of the biggest tech acquisitions of its era, O'Leary launched O'Leary Ventures, a diversified investment firm that backs founders who value data over ego and performance over posturing. His portfolio now stretches across consumer goods, technology, manufacturing, and financial products, reflecting his philosophy that a good deal is simple, scalable, and rooted in numbers that actually add up.
Known for his blunt honesty and zero-fluff communication style, O'Leary has become a global voice for business clarity in a world drowning in hype. Both on and off the show, he forces entrepreneurs to think sharper, defend their decisions, and understand exactly why a deal is — or isn't — worth doing.
Transcript
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| 0:00.0 | Most people talk 70% of the day, listen 30. |
| 0:03.0 | You should actually listen 70% of the day, talk 30. |
| 0:07.3 | Because when you listen, you get more power. |
| 0:09.7 | Welcome to the home service expert, where each week, Tommy chats with world-class entrepreneurs |
| 0:15.5 | and experts in various fields, like marketing, sales, hiring, and leadership to find out what's really behind |
| 0:22.6 | their success in business. Now, your host, the Home Service Millionaire, Tommy Mello. |
| 0:29.3 | Before we get started, I wanted to share two important things with you. First, I want you to |
| 0:33.6 | implement what you learned today. To do that, you'll have to take a lot of notes, |
| 0:42.7 | but I also want you to fully concentrate on the interview. So I ask the team to take notes for you. |
| 0:57.3 | Just text notes, N-O-T-E-S, to 888-526-1299. That's 888-526-1299, and you'll receive a link to download the notes from today's episode. |
| 1:02.4 | Also, if you haven't got your copy of my newest book, Elevate, please go check it out. |
| 1:06.8 | I'll share with you how I attracted and developed a winning team that helped me build a $200 million company in 22 states. |
| 1:08.7 | Just go to elevate and win.com forward slash podcast to get your |
| 1:12.5 | copy. Now let's go back into the interview. Today's guest, Harley is an introduction. Kevin O'Leary |
| 1:17.7 | sit next to me, known as millions as Mr. Wonderful from Shark Tank, world class investor, entrepreneur, |
| 1:23.4 | business leader who built and sold the learning company in one of the largest tech deals of all time. |
| 1:29.2 | He went on to launch O'Leary Funds and O'Leary Ventures and today manages a diverse portfolio |
| 1:34.1 | that spans everything from fintech to crypto to consumer brands, bestselling author, |
| 1:39.8 | global speaker, and a straight shooter on personal finance leadership and entrepreneurship. |
| 1:45.2 | Kevin's not here just to talk about money, but also discipline, decision making, and how to build |
| 1:49.6 | wealth that lasts. Kevin, I'm really excited that you're here, brother. |
| 1:54.2 | I appreciate it. Why did you decide to do this is my first question? |
... |
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