Kevin O’Leary Net Worth: How Much Does The Wittiest Shark Earn?

Kevin O’Leary has a success story that’s made for books and screens. With a motto of “Don’t cry about money, it never cries for you,” the world-renowned entrepreneur has amassed a fortune that few have the courage to dream, let alone pursue and make their own. Hailing from Canada, O’Leary is also a businessman, author, politician, and TV personality.

During his stint on ‘Shark Tank’, he came to be known as “Mr. Wonderful” and “the Shark with the sharpest teeth.” He was seen as quite mean, but brilliant. The man has a string of successful businesses and his net worth is estimated to be $400 million as per Celebrity Net Worth. Learn all about his journey of starting with zero cash and a big idea to owning multiple successful companies.

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How Many Companies Does Kevin O’Leary Own?

Kevin O’Leary began his career with SoftKey Software Products in 1979, which he operated from his basement. Soon, sales reached new heights and he earned big bucks. Between 1995 and 1999, the venture capitalist bought almost all of his software competitors, including Mindscape, Broderbund and the Learning Company. Softkey even adopted the TLC name after O’Leary bought it for $606 million. It was in 1999 that TLC was sold to Mattel for $4.2 billion in 1999.

Between selling his company and going after new acquisitions, he also set up his own mutual fund company, O’Leary Funds. He also founded O’Leary Fine Wines. These are at the heart of what the man with a multi-million dollar net worth values. His advice on making money? In O’Leary’s own words – “Here’s how I think of my money: As soldiers. I send them out to war everyday. I want them to take prisoners and come home, so there’s more of them.”

As far as his investments in companies on the business reality show, ‘Shark Tank‘, is concerned, O’Leary is associated with 23 start-ups. The list includes Basepaws, BenjiLock, Bottle Breacher, Certifikid, DrainWig, Geek My Tree, Honeyfund, Illumibowl, Le-Glue, LovePop, Monti Kids, Potato Parcel, Pop It Pal, PRx, Rareform, Rounderbum, SnarkyTea, Surprise Ride, Waivecar, Wicked Good Cupcakes, Wine and Design, Deskview, and Boost Oxygen.

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What Is His Relation With The Wedding Industry?

Mr. Wonderful is a part of the wedding industry as well. Three of his most successful ‘Shark Tank’ businesses – Bottle Breacher, Honeyfund, and Wicked Good Cupcakes – are major players in the wedding market.

Started by husband-and-wife entrepreneurial duo Eli and Jen Crane, Bottle Breacher makes unique 50-caliber bottle openers from recycled bullets. Honeyfund, on the other hand, is a free honeymoon and wedding gift registry. Lastly, Boston-based Wicked Good Cupcakes is a pastry company that went from bringing in $350,000 to $8 million annually after O’Leary stepped in. He often calls it one of the best deals he has ever made.

Other companies of O’Leary that are dominating the wedding industry are Plumfund, LovePop, O’Leary Wines and Songlorious, among others.

Weddings surely generate huge money for businesses, but personally, O’Leary believes that the sum is best invested into the couple’s future. In an interview with CNBC, he recalled his own low-key wedding to his wife Linda. “I said to my wife, ‘Why go in debt?’ Let’s invite our friends over, let’s buy a few cases of beer and I’ll order some pizza. When … you’re starting out, the worst thing you can do is put yourself in debt for your wedding,” O’Leary said, adding “I know it sounds romantic to spend a lot of money — it’s crazy to do that. Save your money, invest it and later you can take everybody out for a great time on the interest you’re making off your bonds and the dividends your stocks are paying.”

What Are His Most Successful Companies?

While O’Leary has invested millions in various deals, per him, the two companies that have made him the most profits were Plated and Groovebook. He told CNBC Make It, “I’ve had many, many successes on ‘Shark Tank’ and many, many failures. That’s the nature of venture investing. But, I’ve had some really big winners. Plated, one of my deals, got sold to Albertsons, the grocery chain, for $300 million dollars. That’s the biggest exit in ‘Shark Tank’ history.” He made a 1,346 percent return on his investment in 2017 itself.

Another big ‘Shark Tank’ win for O’Leary was Groovebook – a photo-printing app subscription service launched by Brian and Julie Whiteman. The company’s sale within two years of ‘Shark Tank’ investment fetched millions. “The deal was only 18 months old at the time of the sale,” O’Leary said. “The co-founders became millionaires. That’s a great outcome.”

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