The Rise, Challenges, and Legacy of Kevin O’Leary

The Life Story of Kevin O’Leary

Kevin O’Leary is a well-established Canadian businessperson, investor, author, and TV personality.

Known as one of the founders of SoftKey and a key presence of Shark Tank, O’Leary is the type of business owner that made his fortune from almost nothing.

In this article, we will learn more about Kevon O’Leary and how he made a fortune with the right idea and no money.

Early Life and Education

Kevin O’Leary was born in Quebec, Canada, on the 9^th of July 1954, to Georgette and Terry O’Leary. Georgette, his mother, was an investor and a small business owner.

Terry, his father, is a salesman of Iris origin. Through his father, O’Leary obtained Irish citizenship.

O’Leary did not have an easy childhood. Because of difficulties at work, his father turned to a life of alcoholism, causing O’Leary’s parents to get a divorce.

His mother remarried and O’Leary spent most of his childhood years in Cambodia, Tunisia, and Cyprus, due to his stepfather’s job constantly moving.

O’Leary went to his school in Quebec at St. George’s School, after which he obtained a bachelor’s degree from Stanstead College.

He later enrolled at the University of Waterloo, where he majored in Environmental studies. He also joined the Ivy Business School from the University of Western Ontario, where he got his master’s degree in 1980.

Originally, he intended to be a photographer. However, due to his mother’s influence, he decided to become a business owner instead.

“Business is war. I go out there, I want to kill the competitors. I want to make their lives miserable. I want to steal their market share. I want them to fear me and I want everyone on my team thinking we’re going to win.” ~ Kevin O’Leary

Personal Life

In 1990, O’Leary married his wife, Linda, with whom he had two children: Trevor and Savannah. The couple went through a separation back in 2011, but they got back together in 2013.

Trevor began working as an engineer for Tesla, whereas Savannah has a career as a filmmaker and multimedia producer.

During his free time, O’Leary enjoys watching football. He is an avid fan of the New England Patriots, frequently going to their games or watching the live streams.

He is also a wine connoisseur, being a member of the Confrérie des Chevaliers du Tastevin.

During his free time, he likes to take photographs, which he exhibits and sells. The proceeds from his photographs are often donated to charity.

Career Beginnings

While still studying for his master’s degree, O’Leary started an internship at Nabisco, a company in Toronto. Eventually, he was promoted to assistant brand manager, gaining more and more insight into how to run his own business.

After finishing college, he began looking for jobs and started working as a TV producer.

Together with three former classmates, they decided to set up their own broadcast company, “Special Event Television” (SET), which focused on sports. Eventually, O’Leary sold his share of the company to his partners and began pursuing his ventures.

“Working 24 hours a day isn’t enough anymore. You have to be willing to sacrifice everything to be successful, including your personal life, your family life, maybe more. If people think it’s any less, they’re wrong, and they will fail.” ~ Kevin O’Leary

Founding of SoftKey and Initial Success

In the mid-’80s, computers started gaining a lot of popularity. O’Leary saw an opportunity in this – so, in 1986, he decided to lay the foundations of his own software company.

The business was called SoftKey and it provided computer software products to customers.

The company gained a lot of success, especially as computers became cheaper and cheaper in the following years. The demand was increasing with the drop in prices, causing the company to become huge by the late 80s.

In the late 90s, SoftKey acquired two of its biggest competitors: Wordstar and Spinnaker Software.

O’Leary’s Television Career

Later, in 2006, O’Leary made his TV debut at “Dragon’s Den,” Canada’s version of “Shark Tank.” He was one of the show’s venture capitalists, exhibiting a blunt and strong persona. He also appeared in “Shark Tank” itself as one of the judges, until 2014.

In 2008, he also was a co-host on “Discovery Project Earth”, a show on Discovery Channel. In the show, he had the role of a punk who looked for innovative ways on reversing climate change.

Investment and Financial Successes

Aside from business ownership, O’Leary also makes a profit through ETFs and investments. In 2015, O’Leary launched ETFs through O’Shares Investments.

He valued portfolio diversification, advocating that for success, you need the same percentage of bonds as your age.

For instance, if you are a 30-year-old investor, you need to hold 30% in bonds while the rest of 70% should be in stocks.

O’Leary also dabbled with gold investments, placing around 5% of his portfolio in physical gold. He did not want to invest in the gold-mining companies themselves, as he placed great importance on cash flow.

“Unions are about the collective leverage, the power of numbers versus the power of capital.” ~ Kevin O’Leary

Philanthropy and Social Impact

Kevin O’Leary runs the O’Leary Foundation, a non-profit dedicated to supporting human service, health, and education programs.

The foundation aims to help young entrepreneurs raise money to make their business ideas come true.

O’Leary also advocates for financial literacy, supporting the NFEC’s United for Financial Literacy Campaign.

He used O’Leary Funds to help companies reach that goal and influenced many of his readers through his financial literacy books.

Political Aspirations and Advocacy

O’Leary describes himself as a liberal, advocating for transgender rights and same-sex marriage. He also supports marijuana legalization and regulation.

He believed that “assisted suicide” is something that should be implemented for those who require it, citing Switzerland as an example.

Also, O’Leary frequently complained about the Canadian corporate tax rates, claiming that they are too high.

He made a promise to take out the national carbon tax. He also made promises that he would withhold transfer payments unless they eliminate the tax.

Challenges and Controversies

Throughout his career, O’Leary went through a series of losses as well. In 1995, he announced that through SoftKey, he would purchase “The Learning Company” for $606 million.

After rebranding SoftKey into “The Learning Company,” the HQ moved to Massachusetts and the company experienced great losses from the acquisitions.

Later, in 1999, O’Leary gave his company to Mattel, a business that manufactured toys. He also left Mattel when it began showing heavy losses.

The acquisition, which cost him a total of $4.2 billion, was later referred to as one of the most disastrous business deals in near history.

O’Leary’s Books and Media Ventures

O’Leary also dabbled in the career of a writer. His first book was released in 2022 and was titled “Cold Hard Truth: On Business, Money, and Life.”

He released two more books as sequels to the first one, where he coached his readers on business, career, and education.

Kevin also attempted to join politics in 2017 by campaigning for leadership of the “Conservative Party of Canada.” However, after a lack of support from the people in Quebec, he withdrew his campaign.

“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.” ~ Kevin O’Leary

Recent Ventures and Current Activities

In 2021, O’Leary joined the Board of Advisors of ARHT Media, together with Carlos Slim and Paul Anka. He is also continuing his work as a venture capitalist through O’Leary Ventures, looking for companies that hold great potential.

That being said, after funds have declined over the years, O’Leary no longer manages outside money.

O’Leary also continues to serve as chairman for O’Leary Finds Management LP. In 2021, he took ownership stakes in FTX.com and FTX.US, becoming an ambassador and spokesperson for FTX.

Legacy and Impact

Kevin O’Leary’s legacy is significantly tied to the companies he invested in. Through his appearances in Shark Tank as a venture capitalist, he invested in various startups that could not have started without his success.

His books also had a great impact on business owners who wanted to be successful. His business model served as inspiration for young entrepreneurs, helping them reach success with a strong foundation.

Conclusion

Kevin O’Leary is a strong figure in the business world. He became a multimillionaire by having the right idea at the right time, taking the tech world by the reigns.

His success as a venture capitalist and investor also brought him to the top, contributing not only to his success but also to the success of other business owners.

“So much of life is a negotiation – so even if you’re not in business, you have opportunities to practice all around you.” ~ Kevin O’Leary

Key Points

Kevin O’Leary is a Canadian businessperson, investor, author, and TV personality.
He co-founded SoftKey and was a mainstay on Shark Tank.
Born in Quebec in 1954, O’Leary faced a challenging childhood with his parents’ divorce and lived in various countries due to his stepfather’s job.
He pursued education in Quebec and later at the University of Waterloo and the University of Western Ontario.
O’Leary originally wanted to be a photographer but was influenced by his mother to become a business owner.
He married Linda in 1990; they have two children, Trevor and Savannah.
While studying, O’Leary interned at Nabisco and later co-founded “Special Event Television.”
In the mid-’80s, he founded SoftKey, which became highly successful, acquiring Wordstar and Spinnaker Software.
He began his TV career in 2006 on “Dragon’s Den” and later joined “Shark Tank.”
O’Leary has launched ETFs through O’Shares Investments and advocates for a specific investment strategy.
He established the O’Leary Foundation, supporting young entrepreneurs, and advocates for financial literacy.
Politically, he supports transgender rights, same-sex marriage, marijuana legalization, and has voiced concerns about Canadian tax rates.
He faced business challenges with “The Learning Company” and its acquisition by Mattel.
O’Leary has authored books offering guidance on business, money, and life.
In 2017, he briefly pursued political leadership of the Conservative Party of Canada.
Recently, he joined the Board of Advisors of ARHT Media and continues his venture capitalist activities.
O’Leary’s legacy includes investments in startups through Shark Tank and the influence of his books on entrepreneurs.
His success primarily stems from timely tech ventures and his work as an investor and venture capitalist.

Kevin O’Leary

Timeline of Kevin O’Leary’s Life

1954:

Kevin O’Leary is born in Quebec, Canada, on the 9th of July.

Early Years:

O’Leary spends his childhood in Cambodia, Tunisia, and Cyprus due to his stepfather’s job.
He attends St. George’s School in Quebec.

Late 1970s:

O’Leary obtains a bachelor’s degree from Stanstead College.
He enrolls at the University of Waterloo, majoring in Environmental studies.

1980:

O’Leary earns his master’s degree from the Ivy Business School at the University of Western Ontario.

Early 1980s:

While studying for his master’s, O’Leary interns at Nabisco in Toronto and later becomes the assistant brand manager.
After college, O’Leary works as a TV producer and co-founds “Special Event Television” (SET) with classmates, which focuses on sports.

1986:

O’Leary founds SoftKey, a software company.

Late 1980s:

SoftKey experiences significant success with increasing computer affordability and popularity.

Late 1990s:

SoftKey acquires major competitors, Wordstar and Spinnaker Software.
SoftKey, after rebranding to “The Learning Company,” suffers losses and is later given to Mattel. This deal is later seen as one of the most disastrous business decisions.

1990:

O’Leary marries Linda. They later have two children, Trevor and Savannah.

2006:

O’Leary makes his TV debut on “Dragon’s Den,” the Canadian version of “Shark Tank.”

2008:

He co-hosts “Discovery Project Earth” on the Discovery Channel.

2011:

O’Leary and Linda undergo a separation.

2013:

O’Leary and Linda reconcile.

2014:

O’Leary concludes his appearance as a judge on “Shark Tank.”

2015:

O’Leary launches ETFs through O’Shares Investments.

2017:

Kevin attempts to join politics by campaigning for the leadership of the “Conservative Party of Canada.” He later withdraws due to lack of support in Quebec.

2021:

O’Leary joins the Board of Advisors of ARHT Media alongside Carlos Slim and Paul Anka.
He continues his venture capitalist endeavors through O’Leary Ventures but stops managing outside money.
O’Leary takes ownership stakes in FTX.com and FTX.US and becomes their ambassador and spokesperson.

2022:

O’Leary releases his first book titled “Cold Hard Truth: On Business, Money, and Life.” He later releases two more books as sequels.

Legacy:

O’Leary’s legacy involves his investments in numerous startups through Shark Tank and his impact on young entrepreneurs via his books and business model.

This timeline covers the major events and milestones in Kevin O’Leary’s life as described in the provided text.

Life Lessons

From the life story of Kevin O’Leary, we can extract multiple teachable lessons, which can inspire and guide budding entrepreneurs, investors, and anyone keen on personal development. Here are some of the key lessons:

Resilience in the Face of Adversity: Despite facing a challenging childhood due to his parents’ divorce and having to move to different countries, O’Leary managed to find his way, demonstrating that personal hardships can be overcome.
Influence of Family: The influence of family can shape one’s career decisions, as evidenced by O’Leary’s shift from wanting to be a photographer to becoming a business owner, influenced by his mother.
Constant Learning: Continuous education and self-improvement are vital. O’Leary not only pursued a bachelor’s degree but also went on to earn a master’s degree. His diverse educational background contributed to his versatile career.
Identify Market Trends: O’Leary’s establishment of SoftKey during the rise of computers showcases the importance of identifying and capitalizing on market trends early on.
Adaptability: From his role as a TV producer to being an investor on Shark Tank, O’Leary displayed adaptability in various professional roles, proving the importance of being versatile and open to new opportunities.
Risk and Diversification: His investment strategies, like having the same percentage of bonds as your age or investing 5% of his portfolio in physical gold, show the importance of calculated risk and portfolio diversification.
Giving Back: Through the O’Leary Foundation, he emphasizes the significance of giving back to the community and supporting future entrepreneurs.
Financial Literacy: Advocacy for financial literacy underscores its importance in individual growth and making informed financial decisions.
Political Involvement: Engaging in political and social causes you believe in, as O’Leary did with issues like transgender rights, same-sex marriage, and tax reforms, shows that one can use their platform to advocate for change.
Learning from Mistakes: O’Leary’s venture with “The Learning Company” and its subsequent losses demonstrate that even successful individuals face setbacks, and it’s crucial to learn and adapt from them.
Diversifying Career Paths: By branching out into writing and media ventures, O’Leary underscores the importance of diversifying one’s income streams and professional pursuits.
Leaving a Legacy: O’Leary’s investments in startups through Shark Tank and his books highlight the importance of leaving a lasting impact that benefits others.
Timing is Everything: The narrative underscores the significance of having the right idea at the right time, as seen in O’Leary’s tech venture with SoftKey.
Seek Mentorship: The early stages of O’Leary’s career at Nabisco and learning from professionals highlight the significance of seeking mentorship and gaining insights from more experienced individuals.
Relationships Matter: Despite facing personal challenges, such as separation, O’Leary and his wife Linda managed to reconcile, emphasizing the importance of personal relationships and working through challenges together.

In conclusion, Kevin O’Leary’s life story is a testament to perseverance, adaptability, continuous learning, and the importance of recognizing opportunities. These lessons can serve as valuable insights for individuals in any stage of their personal or professional journey.

Facts

Kevin O’Leary is a Canadian businessperson, investor, author, and TV personality.
He is one of the founders of SoftKey.
Kevin O’Leary was a presence on the TV show Shark Tank.
Kevin O’Leary was born in Quebec, Canada, on the 9th of July 1954.
His parents were Georgette and Terry O’Leary.
Georgette was an investor and a small business owner.
Terry was a salesman of Iris origin.
O’Leary obtained Irish citizenship through his father.
Due to his stepfather’s job, O’Leary spent parts of his childhood in Cambodia, Tunisia, and Cyprus.
He attended St. George’s School in Quebec.
O’Leary obtained a bachelor’s degree from Stanstead College.
He majored in Environmental studies at the University of Waterloo.
O’Leary got his master’s degree from the Ivy Business School at the University of Western Ontario in 1980.
He originally wanted to be a photographer.
In 1990, O’Leary married Linda and they have two children, Trevor and Savannah.
Trevor works as an engineer for Tesla and Savannah is a filmmaker and multimedia producer.
O’Leary is a fan of the New England Patriots.
He is a member of the Confrérie des Chevaliers du Tastevin.
O’Leary started an internship at Nabisco in Toronto during his master’s studies.
He co-founded “Special Event Television” (SET) which focused on sports broadcasting.
In 1986, O’Leary founded SoftKey.
SoftKey acquired Wordstar and Spinnaker Software in the late 90s.
O’Leary made his TV debut in 2006 on “Dragon’s Den”.
He appeared on “Shark Tank” as a judge until 2014.
In 2008, he co-hosted “Discovery Project Earth”.
O’Leary launched ETFs through O’Shares Investments in 2015.
He invests around 5% of his portfolio in physical gold.
O’Leary runs the O’Leary Foundation which supports young entrepreneurs.
He supports the NFEC’s United for Financial Literacy Campaign.
O’Leary describes himself as a liberal, advocating for transgender rights, same-sex marriage, and marijuana legalization.
In 1995, SoftKey acquired “The Learning Company” for $606 million.
O’Leary’s acquisition of “The Learning Company” was later referred to as a disastrous business deal.
He has written books including “Cold Hard Truth: On Business, Money, and Life.”
O’Leary attempted to join politics in 2017 for the leadership of the “Conservative Party of Canada” but withdrew his campaign.
In 2021, he joined the Board of Advisors of ARHT Media.
O’Leary took ownership stakes in FTX.com and FTX.US in 2021.
He serves as chairman for O’Leary Finds Management LP.
Kevin O’Leary’s legacy includes investments in various startups through Shark Tank.
His books have impacted many business owners and young entrepreneurs.
Kevin O’Leary became a multimillionaire through timely business ideas and investments.

Questions and Answers

The information in this post answers many of the questions about Kevin O’Leary. In addition, this section provides a summary and any further information.

Who is Kevin O’Leary?
- Kevin O’Leary is a well-established Canadian businessperson, investor, author, and TV personality known as one of the founders of SoftKey and a key presence on Shark Tank.
Where and when was Kevin O’Leary born?
- Kevin O’Leary was born in Quebec, Canada, on the 9th of July 1954.
Who are Kevin’s parents and what did they do?
- Kevin’s parents are Georgette and Terry O’Leary. Georgette was an investor and small business owner while Terry was a salesman of Irish origin.
Did Kevin O’Leary face any challenges during his childhood?
- Yes, due to his father’s difficulties at work and subsequent turn to alcoholism, O’Leary’s parents divorced. O’Leary also spent much of his childhood in Cambodia, Tunisia, and Cyprus due to his stepfather’s job.
Where did O’Leary receive his education?
- O’Leary went to St. George’s School in Quebec, received a bachelor’s degree from Stanstead College, majored in Environmental studies at the University of Waterloo, and obtained a master’s degree from the Ivy Business School at the University of Western Ontario in 1980.
What was O’Leary’s original career choice?
- He originally intended to become a photographer.
Can you provide details about O’Leary’s personal life?
- In 1990, O’Leary married Linda, and they have two children: Trevor and Savannah. They separated in 2011 but reconciled in 2013. Trevor works as an engineer for Tesla, while Savannah is a filmmaker and multimedia producer. O’Leary is also a New England Patriots fan, a wine connoisseur, and enjoys photography.
How did O’Leary start his career?
- O’Leary began his career with an internship at Nabisco in Toronto during his master’s studies and then worked as a TV producer. He co-founded “Special Event Television” (SET) which focused on sports.
What is SoftKey?
- SoftKey is a software company founded by O’Leary in 1986, which provided computer software products. In the late 90s, SoftKey acquired its competitors, Wordstar and Spinnaker Software.
When and where did O’Leary make his TV debut?

- O’Leary made his TV debut in 2006 on “Dragon’s Den,” the Canadian version of “Shark Tank.” He also became a judge on “Shark Tank” and co-hosted “Discovery Project Earth” in 2008.

How has O’Leary been involved in investments?

- In 2015, O’Leary launched ETFs through O’Shares Investments, advocated for portfolio diversification, and invested around 5% of his portfolio in physical gold.

What are some of O’Leary’s philanthropic efforts?

- O’Leary runs the O’Leary Foundation which supports young entrepreneurs and backs the NFEC’s United for Financial Literacy Campaign. He also promotes financial literacy through his books.

How has O’Leary been involved in politics?

- O’Leary describes himself as a liberal and has advocated for various social causes. He has also commented on Canadian tax policies and even campaigned for leadership of the “Conservative Party of Canada” in 2017, though he later withdrew.

What challenges has O’Leary faced in his business ventures?

- One notable challenge was the acquisition of “The Learning Company” in 1995, which eventually led to significant business losses.

Has O’Leary written any books?

- Yes, O’Leary released his first book in 2022 titled “Cold Hard Truth: On Business, Money, and Life” and followed with two sequels, providing guidance on business, career, and education.

What were some of O’Leary’s recent ventures as of 2021?

- In 2021, O’Leary joined the Board of Advisors of ARHT Media and continued his venture capitalist work through O’Leary Ventures. He also took ownership stakes in FTX.com and FTX.US.

How has O’Leary impacted the business world and society at large?

- Kevin O’Leary’s legacy is closely associated with his investments in startups through Shark Tank, as well as his guidance and inspiration provided through his books for aspiring entrepreneurs.

How would you describe Kevin O’Leary’s success?

- Kevin O’Leary is a prominent figure in the business world who became a multimillionaire by capitalizing on timely opportunities, particularly in the tech sector. His achievements as a venture capitalist and investor have not only contributed to his own success but also to the success of other business owners.

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Randstad Canada, CC BY 2.0, via Wikimedia Commons