You might know him for his television appearances on Shark Thank and other TV shows, or for his short-lived political career in Canada, for the book he authored, or for being the founder of a company sold for 3.4 billion dollars.

All of this, and more, it’s Kevin O’Leary.

Coming from a modest upbringing, this entrepreneur and investor managed to grow, as of 2020, a net worth estimated in 450 million dollars.

But how did he managed to grow from almost nothing to being one of the most famous businessmen in the US? Keep reading to discover.

Early Life and Education

Born in Montreal, Canada, Kevin O’Leary’s parents were both immigrants, his mother was in fact Lebanese while his father from Ireland.

Like many other successful entrepreneurs, he suffers from dyslexia and realized that back in school when he used to have a hard time reading. He luckily got treated extremely well to see this condition as a “superpower” from some very talented doctors, this gave a huge boost in confidence to Kevin. (source)

Interesting enough, O’Leary had investing in his blood… Let me explain.

Only when his mother died, O’Leary discovered that she was a skilled investor because she kept her portfolio of dividends-paying stocks and high-yield bonds secret. During her life anyway, she taught Kevin his first principles of investing, such as saving ⅓ of his income.

Soon after divorcing from his mother, his father died at just 37 years old. This was a pivotal moment for young Kevin.

He later cited in an emotional interview how much his father taught him and how much he wished that he could see him now and what he has built along the way.

His mother remarried two years later with an economist working for the United Nations. While his biological father was a salesman, his stepfather was a more formally educated person. Because of the job of his stepfather, Kevin’s family started to move every two years to a new country, from Cambodia to Tunisia.

He later cited this worldwide experience as valuable for him as this made him “successful international investors” (source), as he was able to understand and find more hidden opportunities and patterns all across the globe.

But this wasn’t the only reason why his stepfather has been vastly influential for young Kevin O’Leary, as when he graduated high school he wanted to be a photographer.

His stepfather suggested him, however, to first go study at University, and eventually pursue his career as a photographer after that. This taught Kevin an important lesson, the world isn’t just about what we want, such as pursuing our selfish passion for something, but about creating value for others.

After graduating from the University of Waterloo, he then decided to pursue an MBA in Entrepreneurship at the University of Western Ontario. During college he eventually merged his passion for photography with his newborn understanding of business fundamentals: his first company was a film production company. He later sold his stake in the business for 25,000 and gave him his moderate, but first, business success and experience in entrepreneurship.

“There are two types of people: There are people that own the store, and people that scrape the “$&%@” off the floor. You have to decide which one you are.” Kevin O’Leary

Career as an Entrepreneur

Kevin O’Leary is often referring to a story that changed everything in his life. Back in high school, he started working at an ice cream parlor. When the owner of the shop told him that he had to clean the floor out of used gums, he radically refused and got instantly fired by his boss back then.

The experience humiliated him and made him feel like he was giving up control over his own destiny. That’s the breakthrough moment that made Kevin realize he didn’t want to work for anybody else in his life.

After his first moderate business success with his movie production company right after college, Kevin O’Leary started a new education software company called SoftKey in his basement with tho other business partners.

He initially managed to close an important 250,000 seed funding round, however, the investor backdown last-minute.

He had to take a critical choice, either shut down the company or invest his own money from the video production’s ownership he sold previously.

He went for the second choice, eventually convincing his mother as well to invest $ 10,000 in seed capital.

That choice to persist changed Kevin’s destiny forever. Softkey closed important partnerships with PC hardware distributors and producers to bundle his educational software – most mathematics and English language programs CDRoms.

SoftKey later acquired his competitor ‘The Learning Company’ for $606 million (source) and rebranded his company with the newly acquired name.

Four years after this acquisition Mattel bought TLC for a whopping US$4.2 billion.(source)

Despite that acquisition was later reported as one of the worst M&A operations in US business history and turned out to be a bad choice for Mattel, that was also the moment when Kevin O’Leary’s net worth skyrocketed.

Career as an Investor

Kevin O’Leary has been a prolific investor, from his most notorious deals made at Shark Thank and DragonsDen TV Shows to a stake in StorageNow Holdings for which he served as a Director as well and he later sold his ownership for $4.5 million.

His diversification of risk across different industries and focus on cash flow generating companies has yielded the Canadian businessman a great return on his investment over time.

Moreover, he suggests that investors have their age as the percentage of bonds in their portfolios (i.e., 30% in bonds and 70% in stocks for a 30-year old investor, with an increasing proportion of bonds and decreasing proportion of stocks as the investor ages). (source)

Kevin O Leary’s Businesses

Special Event Television (SET), Sold in 1986

SoftKey – TLC, Sold in 1999 to Mattel

StorageNow Holdings (sold his shares in 2004)

O’Leary Funds, Sold in 2015

Currently, Kevin O’Leary runs O’Leary Ventures, a private early-stage venture capital investment company, as well as O’Leary books, and O’Leary Fine Wines.

On 14 July 2015, O’Leary launched an ETF through O’Shares Investments, a division of his investment fund, O’Leary Funds Management LP, where O’Leary serves as chairman. (source)

A company called Something Wonderful is the one he uses to manage all the investments he does on Shark Thank and previously on Dragondends as well. The name of this company is clearly referring to the nickname he has on the show of “Mr. Wonderful.”

Kevin O Leary Family

O’Leary, as well as his wife, Linda, have been married given that 1990. The couple almost separated in 2011, yet resumed their marital relationship after two years. Linda now serves as the VP of Marketing for O’Leary Wines. They have two children. Trevor, his son, is a music producer as well as DJ.

In a meeting with Inc. Publication, author Brian D Evans O’Leary specified: “Successfully expanding your organization, it consumes your time active. Later in life, you can give for your household things that numerous others can’t have. Because you sacrificed, you’re after that given the benefit of liberty.”



Kevin O’Leary like many other wealthy individuals has decided not to provide more than funds for a comfortable grown-up and education to his kids, as he believes that living out his wealth his kids would have become lazy.

Kevin O Leary Fine Wines

Kevin O’Leary not only has a vast fine wine collection (source), but he as well owns a wine-producing company called ‘O’Leary’s Fine Wines’. His goal with this company is to make accessible to everyone great wine, with price ranges that are between 17$ and 29$.

Kevin O Leary Books

Soon after his appearance on TV Show Dragons Den, he authored his first book called ‘Cold Hard Truth: On Business, Money & Life.’ He later followed on this series with ‘Cold Hard Truth on Men, Women & Money’ and ‘Cold Hard Truth on Family, Kids, and Money’.

Kevin O’Leary Boat Accident

On August 24, 2019, O’Leary was involved in a deadly crash on Lake Joseph in Muskoka, Ontario. When a boat had by O’Leary was involved in a collision with another watercraft, a 48-year-old woman and a 64-year-old male died.

O’Leary said in a declaration that he was cooperating with the police examination, that he was a guest in his boat, and that the various other boat did not have its lights on as well as “left the scene”. The cops specified that both boats left the scene to “go to a place and also both called 911.”

On September 24, Linda O’Leary, the operator of the O’Leary’s watercraft, was billed with “negligent procedure of a vessel” under the small vessel guidelines of the Canada Shipping Act, a cost that carries a maximum 18 months imprisonment and a $1-million fine. The driver of the other watercraft, Richard Ruh of Orchard Park, New York, was billed with “falling short to exhibit navigation light while underway.” On October 11, the general public Prosecution Service of Canada eliminated any kind of jail time for Linda.

Kevin O Leary’s Houses

O’Leary’s primary house as well as tax obligation residency remains in Toronto, Ontario. He additionally preserves a cottage in Muskoka as well as homes in Boston and also Geneva, Switzerland.



Kevin O’Leary Top Lessons

Understand what motivates you, to do so you have to do what you don’t like early on

Never pursue entrepreneurship for the greed of money, entrepreneurship is about freedom, you do it because you wanna be free to do whatever you like and doing the stuff that you want to do

Do not be embarrassed about success once you have it. You worked hard for it

It’s important, to tell the truth, and be direct, he sometimes is mistaken as mean during the show, but really he’s just trying to be direct and now waste other people’s time and money particularly when they’re investing the money from their family

You need the experience to feed your intuition, with time it will get better

Money can corrupt people if that’s they really care about, get to your core values more is not necessarily more

“A salary is a drug they give you when they want you to forget about your dreams” that fear of failure it’s what get people and entrepreneurs to get shit done

Respect every people the same, from warren buffet to the clerk

Metrics to look for: The idea of getting traction

Focus on what matters. not on what is fancy or the ‘next big thing’ on the few things that make a difference, that’s in Kevin O’Leary opinion the reason why most companies fail

Delegate, if they can achieve it they get promote it, if not, they have 3 other trials or they’re out of their way