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Mr. Wonderful: Behind the scenes with Shark Tank’s Kevin O’Leary

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Mr. Wonderful: Behind the scenes with Shark Tank’s Kevin O’Leary
Photo courtesy of Kevin O'Leary

There aren’t many successful people who wear more hats than Kevin O’Leary, also known as “Mr. Wonderful” on ABC’s award-winning “Shark Tank.”

In addition to being a well-known TV personality, this Canadian-born, self-made millionaire is a go-to expert in both business and financial markets. He’s also a bestselling author and a talented chef.

At his core, though, O’Leary says he’s a passionate advocate for small businesses — and he says that the small business “umbrella” covers many levels of the trucking industry.

“Every truck driver is an entrepreneur,” O’Leary said. “They do it because they love it — otherwise, why would they do it? To me, it’s the modern-day American cowboy. If you ask me, you get freedom from it.”

During Truckload 2024, the Truckload Carriers Association’s annual convention set for March 23-26 in Nashville, Tennessee, O’Leary will share his no-nonsense wisdom with association members as the event’s keynote speaker.

O’Leary is well-versed in major issues facing the trucking industry, including the electrification of heavy-duty transport trucks, which he believes will happen a lot more slowly than some people think.

“Electric trucking is not efficient yet,” he said. “When you are operating a truck, your job is to take care of yourself and make sure you are successful. That includes contracts, equipment, carriage, etc. If you are going to buy into this technology, show me my payback. How fast am I getting my investment back?”

O’Leary says it doesn’t make sense for a trucking business to spend more money to purchase electric trucks if they aren’t going to get that money back while operating the vehicles.

“You can’t just change like that,” he said. “It’s going to take 30 or 40 years before we figure out how to do things right. All of the tech that helps you operate more productively at a lower cost is what you take advantage of now.”

While O’Leary may be most famous for his appearances on “Shark Tank,” the show that brings entrepreneurs before a group of wealthy investors for a chance at launching their products, he has a broad professional history.

Decades ago, O’Leary co-founded SoftKey Software Products, a technology company that sold software geared toward family education and entertainment. During the late 1980s and 1990s, SoftKey became a major consolidator in the global educational software market, having acquired rival companies via hostile takeover bids.

In 2008, O’Leary co-founded O’Leary Funds Inc., a mutual fund management firm focused on global yield investing. He is the company’s chairman and lead investor, while his brother Shane O’Leary serves as the director.

The fund’s assets under management shot from $400 million in 2011 to $1.2 billion in 2012, he shared. The fund’s primary manager was Stanton Asset Management, a firm controlled by the husband-and-wife team of Connor O’Brien and Louise Ann Poirier.

O’Leary is definitely a savvy businessman with a dynamic personality.

But he isn’t all business. His whimsical side comes alive when he talks about his passion for preparing good food.

When the Truckload Authority team asked who he’d invite to a fantasy dinner party, O’Leary didn’t hesitate to list several names.

“Napoleon, Otto von Bismarck, Henry Kissinger, Attila the Hun, and Cleopatra,” he said. “She was the first woman to run the show,” he said of Cleopatra.

When asked what courses he’d serve to someone like Attila the Hun, O’Leary quipped, “A whole lot of beef.”

On a more serious note, O’Leary says that in his personal life he follows a strict routine and diet.

“When I was younger, I didn’t give a shit about what I ate or drank, and I didn’t exercise,” he said. “That’s all changed because I have realized, ‘I invest in so many things, why not invest in myself?’”

Why the change? O’Leary says he got a “wake-up call” several years ago during a routine doctor’s visit.

“My doctor said, ‘Wow, you are going to stroke out. You are basically gonna die,’” O’Leary said. “My blood pressure was at a crazy level. That is when I started caring about my diet and watching how much I drink.”

As a result, O’Leary says, he’s lost 35 pounds and now feels better than ever.

One of the best parts of his new lifestyle is that he can still enjoy gourmet food.

“I do a lot of cooking,” he said. “I try to find ways to take classics, like French cooking, and swap out the heavy ingredients for something healthier.”

In addition, he greatly reduces the amount of sugar in his recipes.

“We use too much sugar in North American cooking. It kills the taste,” he explained.

When asked about his outlook for the future, O’Leary said one thing he’s most worried about is the state of regional banks as megabanks become the norm.

“Right now, you have 4,100 regional banks,” he said. “In five years, that will be down to 2,000 because so many of them have really bad portfolios in commercial real estate.

“The cost of running a business has quadrupled in terms of interest costs,” he continued. “The Fed rate is 5.5%, but that is not the loan book rate. That rate is between 9% and 14%.”

While the world may think of O’Leary as “Mr. Wonderful,” he says he bills himself as “Mr. Small Business.” He currently supports around 40 entrepreneurs and their ventures.

The bottom line, O’Leary says, is that small businesses must succeed — and banks should find ways to help them.

“It’s wrong that there isn’t any money for small businesses,” he said. “Sixty percent of jobs come from small businesses. Every dollar should be 60% to the small guy and 40% to the big guy. That would be money well spent.”

John Worthen

Born in Pine Bluff, Arkansas, and raised in East Texas, John Worthen returned to his home state to attend college in 1998 and decided to make his life in The Natural State. Worthen is a 20-year veteran of the journalism industry and has covered just about every topic there is. He has a passion for writing and telling stories. He has worked as a beat reporter and bureau chief for a statewide newspaper and as managing editor of a regional newspaper in Arkansas. Additionally, Worthen has been a prolific freelance journalist for two decades, and has been published in several travel magazines and on travel websites.

Avatar for John Worthen
Born in Pine Bluff, Arkansas, and raised in East Texas, John Worthen returned to his home state to attend college in 1998 and decided to make his life in The Natural State. Worthen is a 20-year veteran of the journalism industry and has covered just about every topic there is. He has a passion for writing and telling stories. He has worked as a beat reporter and bureau chief for a statewide newspaper and as managing editor of a regional newspaper in Arkansas. Additionally, Worthen has been a prolific freelance journalist for two decades, and has been published in several travel magazines and on travel websites.
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