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Shark Tank’s ‘Mr. Wonderful’ Details His Investment Philosophy

Shark Tank’s ‘Mr. Wonderful’ Details His Investment Philosophy

Kevin O’Leary Analyzes Current Financial Trends and His Investments on Popular Podcast

Stansberry Investor Hour host Porter Stansberry interviewed serial entrepreneur and Shark Tank star Kevin O’Leary. The two businessmen and media personalities had an animated discussion about deal structures, value investing, and wealth preservation.

Known as “Mr. Wonderful” for his brash and demeaning on-air personality, O’Leary made the bulk of his fortune as the co-founder of SoftKey in the 80’s.

“I’m just telling people the truth about business, which is binary,” O’Leary said. “You either make money, or you lose it. People appreciate that over time. I stop people from making disastrous mistakes. If you think I’m tough on Shark Tank, wait until you see what the real world will do to you. I’m your best friend. I’m the only shark that tells the truth.”

This decade, O’Leary started mutual fund management firm O’Leary Funds and a beverage company, O’Leary Fine Wines. He goes into business always looking to sustain his wealth while making steady gains.

“My mother used to have a saying, ‘Never spend the principal… just the interest,’” O’Leary said. “She was the same way on stocks. She wanted to get paid a dividend. When you invest in something, it has to provide an ongoing return in addition to potential capital gains all the time.”

When it comes to private equity and angel investing, O’Leary loves to structure royalty deals – particularly in family business – instead of asking for equity splits or other ownership options.

“You don’t have to be an equity owner to align your interests with an entrepreneur,” O’Leary told Stansberry. “A royalty stream can do that too.”

The discussion finished with O’Leary sharing the secret to his brand-building: honesty.

“Tell the truth,” O’Leary said. “The first time you lie to your significant other, you lose 50% of the equity in that relationship forever. You can never get it back to where it was. So why don’t you just tell the truth every day?”

Listen to the episode with Kevin O’Leary at

About Stansberry Investor Hour

From business, investing and politics to entertainment and social issues, the Stansberry Investor Hour with Porter Stansberry and Buck Sexton offers candid, intelligent, and entertaining takes on today’s most important headlines… inviting a variety of insightful guests to join the conversation. It is becoming a required stop for politicians, the media, and financial and economic experts. The show has been host to a wide variety of prominent names from all sides of the spectrum and has a global audience in more than 100 countries. It is ranked highly in the Investing section of iTunes. New episodes release every week.

Stansberry Investor Hour podcasts can be accessed at

The latest episode with Kevin O’Leary can be heard at

About Stansberry Research

Stansberry Investor Hour is a part of Stansberry Research – a subscription-based publisher of financial information and software, serving millions of investors around the world.

To learn more about Stansberry Research, visit

About Porter Stansberry

Porter Stansberry founded Stansberry Research in 1999 with the firm’s flagship newsletter, Stansberry’s Investment Advisory. 

Prior to launching Stansberry Research, Porter was the first American editor of the Fleet Street Letter, the world’s oldest English-language financial newsletter.

Today, Porter is well-known for doing some of the most important – and often controversial – work in the financial advisory business. Since he launched Stansberry’s Investment Advisory, his string of accurate forecasts has made his advisory one of the most widely read in the world and has helped his readers both avoid catastrophe and make incredible gains.

For example, his dead-on prediction of the mortgage meltdown got the attention of Barron’s, who said Porter’s work was “remarkably prescient… Nothing, as far as we can see, has happened to contradict his dire prophecy…”

At Stansberry Research, Porter oversees more than a dozen of the best editors and analysts in the business, who do an exhaustive amount of real-world, independent research. Together, his group has visited hundreds of publicly traded companies to bring Stansberry Research subscribers the safest, most profitable investment ideas in the world, no matter what’s happening in the markets.

About Buck Sexton

Buck Sexton is host of the nationally syndicated talk radio program, Buck Sexton with America Now, heard on over 100 stations across the country.

Buck is a political commentator and national security analyst who appears frequently on the Fox News Channel and CNN. Buck has also had the distinction of being a guest host for Rush Limbaugh, Glenn Beck and Sean Hannity on their nationally syndicated radio shows, and is the only talent to have hosted all three shows.

Buck formerly served as a CIA officer in the Counterterrorism Center (CTC) and the Office of Iraq Analysis. He completed tours of duty as an intelligence officer in Iraq and Afghanistan, as well as other hotspots around the globe, and led intelligence briefings for senior U.S. officials including the president. Buck also served in the New York Police Department (NYPD) Intelligence Division working on counterterrorism issues.

A graduate of Amherst College, Buck was born and raised in New York City, where he currently resides.


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February 2018
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