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How to Build a Wonderful Business with ‘Mr. Wonderful’ | Buffini Podcast

How to Build a Wonderful Business with ‘Mr. Wonderful’ | Buffini Podcast

Buffini Coaching LIVE is a free, two-part series that will give you the strategies, tools, and confidence to own 2026 from day one. On Dec. 3, Brian Buffini will share his legendary Bold Predictions for the year ahead in real estate. On Jan. 22 he’ll be joined by industry thought leaders who will share tactics to help you create the breakthroughs, habits and mindset to win. Learn more here.

To millions of fans of the hit TV show Shark Tank, Kevin O’Leary is “Mr. Wonderful,” the tough, no-nonsense investor who often offers what he calls the “blunt, harsh truth” to those appearing on the show hoping to achieve their own entrepreneurial dreams.

Recently, O’Leary was a guest on Brian Buffini’s podcast, It’s a Good Life, where he discussed his remarkable career, television fame, and tips all real estate professionals can use to achieve their own success.

1. Financial Independence Starts with Discipline

O’Leary’s earliest influence, he said, was not a boss or a mentor, but rather his mother.

“She was fiercely independent as a young woman, didn’t want to ever rely on a man for money. And so even before she got married, she started taking 15% of her salary from the factory and sticking it into a portfolio of telco bonds,” he said. “She had that portfolio for over 50 years. She kept it secret from both her husbands.”

“She never had more than 20% in any one sector and no more than 5% in any one stock, with the exception of one sector during her lifetime. Real estate became the 11th sector,” he said.

When she passed away, the portfolio was “massive,” he noted. He used his share to build a diverse exchange-traded fund and, as his mom did, maintains 20% in real estate.

2. Entrepreneurship Is the Only Real Path to Freedom

A single day working in an ice cream shop changed the direction of O’Leary’s life. When he refused to scrape gum off the floor, he was fired on the spot.

“That moment defined me forever because I realized I don’t want anybody to have the power to control my life. And the only way to avoid that is to become an entrepreneur,” he recalled. “Even though it’s a harder road with more risk, it was still the better path.”

Initially, O’Leary wanted to be a filmmaker and producer but was convinced by his stepfather to pursue a business degree.

Although annoyed by that advice, O’Leary did just that. That education, along with important internships, gave him the foundation to start his first company.

“The first thing I did was start a business doing sports programming, television for the hockey leagues in Boston, New York, Philadelphia — the original six teams,” he said. “It was very successful. And one day somebody came to buy it because I owned something called the format rights. That was my first deal. From that day on, I never stopped starting businesses, growing them, and selling them. And I still do that today, except I’m not the operator anymore. I’m kind of the investor guy.”

3. Your Reputation Matters (Especially Online)

O’Leary notes that real estate agents who want to excel should look to the example of his fellow Shark Tank colleague, Barbara Corcoran.

“She’s very smart. She learned long ago that it’s about personal relationships and trust,” he said. “She wanted her agents to communicate transparently and honestly, help clients make decisions, and gain their trust.”

O’Leary added that a real estate agent’s reputation also extends to their online presence.

“I tell every agent I meet, ‘I’m going to check you out on LinkedIn before I even meet you,’” he said. “I’m going to go online and see what people are saying about you… why wouldn’t I do that? It’s free information.”

“You really have to care about what your online presence is like and what you’re talking about in your local market,” he said. “Real estate is local, local, local. You build a reputation; people come to you. Your customer acquisition cost goes to zero.”

Click here to listen to the entire podcast.

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