Kevin O'Leary has 13 seasons of 'Shark Tank' under his belt — but it's not his ownly accomplishment

Kevin O’Leary, popularly known as “Mr. Wonderful,” is a household name in the world of business and entrepreneurship. The shrewd star of Shark Tank stands out not only for his wealth but also for his sharp business insights and no-nonsense attitude on the show. With 13 seasons under his belt, O'Leary has built a savvy investment portfolio as well. 

Kevin O'Leary's top deals on Shark Tank

One of O'Leary's most prominent investments on Shark Tank was in the Boston-based baked goods company Wicked Good Cupcakes. Back in 2013, being as cunning as he is, O'Leary negotiated a lucrative royalty deal with the company.  He invested $75,000 in the company in exchange for $1 for each cupcake sold until his investment was repaid, and then $0.45 for each cupcake in perpetuity. 

While the company had only $150,000 in total sales at the time he made the deal, that number grew to a whopping $10 million within three years, according to an on-air update in 2016.

Another successful investment of O'Leary was in cat DNA testing company Basepaws, and a photo-printing app subscription service called Groovebook. O'Leary often refers to Groovebook as one of his best-ever “Shark Tank” investments, the investor told CNBC Make It in 2018.

Along with Mark Cuban, O'Leary made an investment of $75,000 in the company in exchange for a shared 80% of the licensing deals. It didn't take long for the investment to pay as less than a year later, the company was sold to Shutterfly for $14.5 million.

These and dozens of other investments along with his various business ventures allowed Mr Wonderful to amass a 'oh-so-wonderful' fortune as well. 

O'Leary, also known as "Mr. Wonderful," built his wealth through entrepreneurial ventures, television appearances, investments, and endorsements. His initial fortune came from the success of the software company SoftKey International, which he co-founded. Later, he gained prominence through his roles on reality TV shows like "Dragons' Den" and "Shark Tank." Kevin O'Leary has an estimated net worth of $400 million. He's recognized for his straightforward, often candid feedback to entrepreneurs on these shows, which contributed to his on-screen persona and nickname.

Kevin O'Leary's income streams are diverse. He has earned significant amounts through his business ventures, particularly the growth and sale of SoftKey International and subsequent investments. O'Leary's appearances on TV shows like "Dragons' Den" and "Shark Tank" also contributed to his income, as he received fees for his role as an investor and mentor to aspiring entrepreneurs. Additionally, O'Leary has authored several books on business and finance, generating royalties and speaking engagements.

His investments in various companies and endorsement deals further bolster his financial portfolio. Mark Cuban's impact on Bottle Breacher has been transformative since the business secured a deal with him on Shark Tank. However, it's essential to recognize that Cuban, along with Kevin O'Leary, manages vast companies, making their involvement a balancing act. While their platforms offer tremendous opportunities, entrepreneurs like Eli Crane understand the realistic constraints on their time.

Kevin O'Leary's earnings from his role on "Shark Tank" are substantial, averaging around $30,000 per episode. With the show typically running 24 episodes per year, his annual income from the program totals approximately $720,000. O'Leary's involvement as an investor and mentor on the show has been a consistent source of income for him.

In 1986, O'Leary started Softkey in a Toronto basement, initially facing funding challenges. The company, publishing CD-based software, grew into a major player in educational software, acquiring rivals like WordStar and Spinnaker.

In 1995, Softkey's acquisition of The Learning Company for $606 million led to its transformation and later acquisition by Mattel for $4.2 billion in 1999. O'Leary became involved with StorageNow Holdings in 2003, a Canadian storage services developer, later acquired for $110 million.

In 2008, O'Leary co-founded O'Leary Funds, a mutual fund firm with a global yield focus, reaching $1.2 billion in assets. The fund later faced penalties for Securities Act violations. In 2015, O'Leary Funds was sold to Canoe Financial. O'Leary also ventured into private equity with O'Leary Ventures and explored areas like mortgages, books, and fine wines. O'Leary launched an ETF in 2015, emphasizing value investing and advocating for portfolio diversification based on age.