[14][21] His stepfather's international assignments caused the family to move frequently, and O'Leary lived in many places while growing up, including Cambodia, Ethiopia, Tunisia, and Cyprus.

[26][27][32] O'Leary attributed his future business success at The Learning Company as a result of the extensive marketing skills that he honed during his assistant brand management days at Nabisco.

The company achieved limited success with minor television shows, soccer films, sports documentaries, and short in-between-period commercials for local professional hockey games.

Desperate to secure funding, O'Leary turned to using the proceeds that he gained from selling his SET share while also convincing his mother to lend him $10,000 in seed capital to establish SoftKey Software Products.

[39] As the software and personal-computer industries were proliferating throughout the course of the early 1980s, O'Leary convinced printer manufacturers to bundle Softkey's program with their hardware.

Softkey products typically consisted of software for home users, especially compilation discs containing various freeware or shareware games packaged in "jewel-case" CD-ROMs.

[6] In 2003, O'Leary became a co-investor and corporate director at StorageNow Holdings, a Canadian developer of climate-controlled storage facilities controlled by Reza and Asif Satchu.

[6] O'Leary later sold his shares which yielded a windfall profit exceeding $4.5 million through realized capital gains, with his initial stake being originally valued at $500,000.

[6] In March 2007, O'Leary joined the advisory board of Genstar Capital, a private equity firm that focuses on investing in health care, industrial technology, business services, and software.

Genstar Capital appointed O'Leary to its Strategic Advisory Board to seek new investment opportunities for its $1.2 billion fund.

[47] In November 2014, O'Leary Funds Management agreed to pay penalties to the Autorité des marchés financiers for violating certain technical provisions of the Securities Act.

[51] On October 15, 2015, O'Leary Funds was sold to Canoe Financial, a private investment-management company owned by Canadian businessman W. Brett Wilson.

In August 2021, it was announced O'Leary would take an ownership stake in the parent companies of FTX.com and FTX.US as part of his compensation for becoming a "spokesperson and ambassador" for FTX.

[67] FTX subsequently went bankrupt due to CEO Sam Bankman-Fried secretly using client funds to make speculative bets that were unsuccessful.

For example, in February 2022, the U.S. 11th Circuit Court of Appeals ruled in a lawsuit against Bitconnect that the Securities Act of 1933 extends to targeted solicitation using social media.

On the show, O'Leary developed a persona as a blunt, abrasive investor, who at one point told a contestant who started crying, "Money doesn't care.

[81] O'Leary has said that the nickname serves both as a tongue-in-cheek reference to his reputation for being mean,[82] as well as a reflection of his view that his blunt assessments are helpful to misguided, naive, and inexperienced entrepreneurs.

[83] Besides his acerbic demeanor, domineering imposition, and blunt television persona, O'Leary has also gained a reputation on both shows for preferring deals in which he loans the entrepreneurs money in exchange for a percentage of future revenue, rather than taking a share of the company.

[94]In 2009, O'Leary hosted a Winnipeg Comedy Festival gala called Savings & Groans in which he performed a Dragon's Den style sketch in which Sean Cullen and Ron Sparks tried to get him to invest in their invention - the wheel.

[4] Having also been a co-host of SqueezePlay on Bell Media's Business News Network (BNN), he returned to the Discovery Channel on September 1, 2014, to join as a contributor for its radio and television stations such as CTV.

[103] In January 2016, O'Leary offered to invest $1 million in the economy of Alberta in exchange for the resignation of Premier Rachel Notley[104] and appeared with four other prospective leadership candidates at a conference for federal Conservatives in late February 2016, where he gave a presentation titled "If I Run, This is How.

[108] In February 2016, Maxime Bernier, a Conservative Quebecois politician, criticized O'Leary, calling him a "tourist"[109] for wanting to be prime minister without being able to speak French.

[8] That same day, his former Dragons' Den co-star Arlene Dickinson stated that she found O'Leary to be too "self-interested and opportunistic" to be qualified for the office of prime minister.

In 2017, O'Leary described hypothetical trade negotiations between US President Donald Trump and Canadian Prime Minister Justin Trudeau as "Godzilla versus Bambi".

[124] He has accused Rep. Alexandria Ocasio-Cortez, a New York politician, of "killing jobs by the thousands," citing higher corporate taxes which she favors.

[129] He has criticized the lack of funding of the Canadian Armed Forces and supports spending the NATO recommended 2% of GDP on military expenditures.

[129][133] O'Leary has proposed creating a "fast track" for citizenship for immigrants who graduate from college or university and find employment, as well as for their spouses and children.

O'Leary publicly stated that the law promoted mediocrity since rich people would be discouraged from running and hurt the businesses that had pledged money for his failed leadership campaign.

[145][146][147] In a 2022 CNBC interview, he mentioned that he has obtained a United Arab Emirates citizenship in order to be able to partner with Emiratis on investments.

The driver of the other boat, Richard Ruh of Orchard Park, New York, was charged with "failing to exhibit navigation light while underway".