Kevin O’Leary

Kevin O’Leary was born in Montreal, Canada, to parents of Irish and Lebanese backgrounds. In his personal recollections, he says his mother remarried after his father’s death, and his stepfather’s work with the International Labour Organization took the family to several countries. These experiences exposed him to different societies and cultures.⁠[1]

O’Leary was born on July 9, 1954. His mother was Georgette Bookalam, and his father, Terry O’Leary, worked for the clothing manufacturer Kiddies Togs. He has a younger brother, Shane.⁠[2][3][1]

In his own account, O’Leary says that his stepfather, George, was finishing a doctorate in business at the University of Illinois at Urbana-Champaign when he met O’Leary’s mother, and that the countries where the family lived included Egypt, France, Japan, Tunisia, Ethiopia, Cyprus, Cambodia and Switzerland. He also says he was diagnosed with dyslexia when he was failing at school; his mother found two McGill University specialists, Marjorie Golik and Sam Rabinovitch, and he says he is grateful to them for helping him excel again.⁠[1]

O’Leary graduated from the University of Waterloo in 1977 with a Bachelor of Environmental Studies in Man-Environment Studies. In 1980, he completed an MBA at the University of Western Ontario’s Ivey Business School. He recalled pursuing business studies to combine his environmental background with commercial skills.⁠[4][5][1]

After completing his MBA, O’Leary founded Special Event Television to produce sports programming. Proceeds from selling the business later helped him start a software company.⁠[1][3]

O’Leary formed Special Event Television with two partners and worked as a producer for hockey announcer Don Cherry. The company’s sports programs included “The Original Six,” “Don Cherry’s Grapevine” and “Bobby Orr and the Hockey Legends.”⁠[2][3]

O’Leary was a co-founder of SoftKey Software Products, Inc., established in Toronto. The Learning Company’s 1998 proxy statement records that he had served from 1984 as president and a director of the pre-1994 SoftKey, which the filings call “Former SoftKey,” and its predecessors. The company’s 1996 annual report likewise dates the start of Former SoftKey’s business to 1984.⁠[2][6][7]

The same proxy statement shows that Michael J. Perik was chief executive officer and a director of Former SoftKey from 1991 to 1994, after serving as vice president of investments at Denbridge Capital Corporation from 1988 to 1991. Robert A. Rubinoff had been a director of Former SoftKey and its predecessors since 1987, and Robert Gagnon served as a director from 1991 to 1994.⁠[6]

SoftKey Software Products, which O’Leary founded (ABCABCABC (American Broadcasting Company) is an American commercial broadcast television network. It grew out of NBC’s Blue radio network, took its name after becoming independent in 1943, developed into a national television network after merging with United Paramount Theatres in 1953, was acquired by Capital Cities in 1985, and has been owned by The Walt Disney Company since 1996. With CBS and NBC it is one of the three traditional U.S. broadcast networks, and it is one of the five networks that rotate in the White House television pool.Open the full entry’s biography gives the founding year as 1986), targeted home education and entertainment software and expanded through acquisitions including WordStar, Spinnaker, The Learning Company, MECC and Broderbund, adopting The Learning Company name.⁠[3]

On February 4, 1994, the company then called WordStar International Incorporated completed a three-party combination with Former SoftKey (SoftKey Software Products Inc.) and Spinnaker Software Corporation and changed its name that day to SoftKey International Inc.; the combination was accounted for as a pooling of interests. WordStar had been incorporated in California in October 1978 as MicroPro International Corporation. After the combination, Michael J. Perik served as chairman and chief executive officer and O’Leary as president and a director.⁠[7][6]

On December 22, 1995, SoftKey acquired control of The Learning Company in the first step of a two-step, all-cash transaction, with merger consideration of $67.50 per share; SoftKey held the entire equity interest from December 27. Total consideration, including estimated transaction costs, was $684.1 million, of which about $543.2 million was paid in cash. Funding included a private offering of $350 million of 5.5% senior convertible notes due 2000, $150 million of senior exchangeable/convertible notes sold to Tribune Company, and a public offering of 2,713,106 common shares that raised about $74.4 million.⁠[7][8]

On December 28, 1995, SoftKey bought Compton’s NewMedia, Inc. and Compton’s Learning Company, formerly wholly owned subsidiaries of Tribune Company, issuing 5,052,697 common shares for a total price of about $104.4 million. For the fiscal year ended January 6, 1996, SoftKey had revenues of $167.0 million and a net loss of $66.0 million, including a $60.5 million charge for incomplete technology tied to products under development at The Learning Company and Compton’s.⁠[7]

SoftKey signed a merger agreement with Minnesota Educational Computing Corporation (MECC) on October 30, 1995, and completed the acquisition on May 17, 1996, for 9,214,007 common shares at a total price of about $284.6 million. On August 12 that year it acquired French educational software company Edusoft S.A. for 752,275 shares, a total price of about $13.3 million, and in September it acquired Dutch consumer software publisher Domus Software B.V.⁠[7][9]

On October 24, 1996, SoftKey International changed its name to The Learning Company, Inc., which the company said reflected its expanded emphasis on educational software. In fiscal 1996 it had revenues of $343.3 million and a net loss of $405.5 million, and as of March 1, 1997, it had about 990 full-time employees, with headquarters in Cambridge, Massachusetts.⁠[9]

On October 23, 1997, The Learning Company acquired all of the equity of Creative Wonders for about $37.8 million, and that year it also bought Learning Services, Skills Bank, Microsystems and TEC Direct for stock. On December 5 it issued 750,000 shares of Series A convertible participating preferred stock in exchange for $150 million of 5.5% notes that investors had bought from Tribune Company, each preferred share convertible into 20 common shares. Fiscal 1997 revenues were $392.4 million and the net loss was $475.7 million, including $515.0 million of amortization, merger and other charges. As of February 2, 1998, it had 1,525 full-time employees; its Canadian subsidiary owned a building in Sherbrooke, Quebec, and leased space in Mississauga, Ontario, and Calgary, Alberta.⁠[8]

On April 9, 1997, O’Leary signed a three-year employment agreement providing a base salary of at least $400,000 a year and a target cash bonus of up to $300,000 a year. The company’s 1998 proxy statement lists his 1995 salary as $300,000; his 1996 salary as $400,000 with a $312,125 bonus and options on 1,000,000 shares; and his 1997 salary as $400,000 with a $300,000 bonus and options on 475,499 shares. As of March 2, 1998, he beneficially owned 1,212,657 shares, or 2.4% of the common stock outstanding, including 212,158 shares issuable on exchange of exchangeable shares held by a corporation he wholly owned.⁠[6]

On March 5, 1998, The Learning Company acquired control of Mindscape for a total of about $152.6 million, about $122.6 million in cash and the rest in 1,366,743 shares. On June 2 it acquired Sofsource for 1,641,138 shares valued at $45 million, and on December 3 it acquired Palladium Interactive for 788,547 shares. It signed a merger agreement with Broderbund Software on June 21, 1998, and completed the merger on August 31, exchanging 0.80 of a Learning Company share for each Broderbund share and issuing 16,848,753 shares in a pooling of interests.⁠[10][11]

Following a September 9, 1998, letter from the Chief Accountant of the U.S. Securities and Exchange Commission to the American Institute of Certified Public Accountants, The Learning Company revalued its in-process technology after discussions with SEC staff and filed amended quarterly reports; the incomplete technology charge for the Mindscape acquisition was reduced from $103 million to $40 million. For fiscal 1998, the company had revenues of $839.3 million and a net loss of $105.4 million.⁠[11][10]

On December 13, 1998, The Learning Company signed a merger agreement with Mattel under which each Learning Company common share would be exchanged for $33.00 of Mattel stock, at a ratio between 1.0 and 1.2 shares based on Mattel’s average closing price on ten randomly selected days out of the 20 trading days before the merger took effect. When Mattel announced the deal the next day, it was valued at about $3.8 billion; the products involved included Carmen Sandiego, Reader Rabbit, Oregon Trail, Myst and Riven.⁠[11][12]

Between December 16 and 23, 1998, Learning Company stockholders filed six purported class actions in the Delaware Court of Chancery, New Castle County, alleging that the company’s directors breached their fiduciary duties in the Mattel merger; four also named Mattel for allegedly aiding and abetting. The plaintiffs sought to enjoin the merger or rescind it if completed, plus damages. The company said it would defend the actions and pursue the merger.⁠[11]

Mattel and The Learning Company completed their merger in May 1999. On March 31, 2000, Mattel’s board decided to dispose of its consumer software business, principally The Learning Company, classifying it as discontinued operations. On October 18, Mattel transferred The Learning Company to an affiliate of Gores Technology Group in exchange for rights to contingent consideration linked to future operating earnings, asset sales and other events.⁠[13]

The joint proxy statement dated March 26, 1999, explained that O’Leary and Michael J. Perik had amended employment agreements taking effect when the merger closed: Mattel would pay each a $650,000 annual base salary to remain officers of its Learning Company division; maximum aggregate severance under each agreement was about $5.25 million, excluding any gross-up payments; each would receive premium-price options on 1,000,000 Mattel shares after the merger; and their existing options would convert into Mattel options and become immediately exercisable.⁠[14]

Special stockholder meetings of both companies were scheduled for May 7, 1999. The merger was completed on May 13 as a stock-for-stock transaction accounted for as a pooling of interests: each Learning Company common share converted into 1.2 Mattel common shares, and Mattel issued about 126 million shares.⁠[14][15]

On October 4, 1999, Mattel announced that earnings from its Learning Company business would fall short of expectations; at the acquisition, Mattel had expected the unit to earn $50 million. In the third quarter the segment had sales of $195.0 million and a loss of $132.5 million, against a profit of $54.5 million a year earlier. Mattel attributed this to about $58 million of distributor and retailer returns and allowances, about $56 million of added bad-debt reserves (including $35 million tied to one major distributor), and its decision not to complete an e-commerce and licensing transaction expected to yield about $60 million in pre-tax earnings. In the second quarter Mattel had already recorded a $345.0 million non-recurring pre-tax restructuring and other charge tied to its merger integration plan.⁠[15][16]

After the October 4 announcement, stockholders filed purported class actions in the U.S. District Courts for the Central District of California, the Southern District of New York and the District of Massachusetts, as well as a derivative complaint in Los Angeles County Superior Court; Mattel said the suits were without merit and that it would defend them vigorously. In November 1999, Michael J. Perik and O’Leary left The Learning Company, and Francesca Luzuriaga was named chief operating officer of Mattel Interactive, the unit overseeing the business. In February 2000, Mattel chief executive Jill Barad left the company’s top post.⁠[15][16][17][18]

In March 2000, the stockholder suits against Mattel were consolidated into two lead cases: Thurber v. Mattel, Inc. et al., under Section 10(b) of the Securities Exchange Act, and Dusek v. Mattel, Inc. et al., under Section 14(a). The defendants were Mattel and certain present and former officers and directors, and the plaintiffs alleged that false or misleading statements in the merger’s joint proxy statement and elsewhere had inflated Mattel’s stock price. The U.S. District Court for the Central District of California dismissed both cases with leave to amend in January 2001 and, in December 2001, denied motions to dismiss the amended complaints. A separate class action by former Broderbund stockholders, In re Broderbund, alleged that The Learning Company had misstated its financial results before Mattel acquired it; it was dismissed in May 2001 and appealed to the Ninth Circuit. Stockholders also filed derivative suits in the Delaware Court of Chancery, Los Angeles Superior Court and the Central District of California concerning the acquisition and severance packages for certain former executives. Mattel maintained that the actions were without merit.⁠[19][20]

On December 5, 2002, Mattel announced an agreement in principle to settle the shareholder litigation related to its 1999 acquisition of The Learning Company: Mattel and its directors’ and officers’ liability insurers would pay the plaintiffs a total of $122 million, Mattel expected its own pre-tax cost, covering the uninsured portion and legal and professional fees, to be about $25.5 million, and it agreed to negotiate certain corporate governance procedures with plaintiffs’ counsel; the settlement required a final written agreement and court approvals. Mattel later recorded a $25.4 million settlement charge in 2002 and a $7.8 million gain from an insurance recovery in 2003, describing the litigation as settled in 2002.⁠[21][13]

A July 2000 Mattel filing shows that its consumer software business, consisting primarily of The Learning Company’s assets, posted a 1999 loss from discontinued operations of $190.8 million, and that Mattel’s net investment in the business was $462.0 million at December 31, 1999. Mattel’s right to future consideration under the October 18, 2000, transaction could also be based on 20% of the new company’s enterprise value at the end of five years. In the fourth quarter of 2001, Mattel received $10.0 million after Gores Technology Group sold the entertainment and education divisions; in the third quarter of 2002, after Gores completed the sale and liquidation of non-cash proceeds from the education and productivity divisions, Mattel recognized an after-tax gain of $27.3 million and in October 2002 collected $43.3 million.⁠[22][20][23]

In 2003, O’Leary co-founded Storage Now, a developer of temperature-controlled storage facilities. It expanded through development and acquisitions before In Storage REIT acquired it in March 2007.⁠[3]

Storage Now’s operations extended to 11 cities, and its clients included Merck and Pfizer.⁠[3]

O’Leary began appearing on Canada’s entrepreneurship investment show Dragons’ Den in 2006 and later became an investor on ABC’s Shark Tank. Known publicly as Mr. Wonderful, he assesses business plans and discusses investment terms on the shows. He also appeared on Discovery’s Project Earth and served as a CNBCCNBCCNBC is an American business and financial news cable channel launched by NBC in 1989; it merged with its rival FNN in 1991 and since January 2026 has been part of Versant Media Group, spun off from Comcast.Open the full entry commentator.⁠[24][3]

In 2007, O’Leary became a founding investor and director of Stream Global Services, Inc., a Boston-based outsourced business services company.⁠[3]

In July 2008, O’Leary’s fund business launched its first product, the O’Leary Global Equity Income Fund. In less than two years, O’Leary Funds raised C$1 billion across seven closed-end and five open-end funds. Its primary manager was Connor O’Brien; O’Leary, the public face of the brand, did not select investments and provided “consulting services.”⁠[25]

In 2009, ABC launched the entrepreneurship investment show Shark Tank, with O’Leary joining Barbara CorcoranBarbara CorcoranBarbara Corcoran is a real estate entrepreneur, investor, author and television personality. She founded The Corcoran Group and sold it to NRT in 2001. Known for her role on ABC’s Shark Tank, she also writes books, hosts a podcast and speaks publicly.Open the full entry, Kevin Harrington, Robert HerjavecRobert HerjavecRobert Herjavec is a Croatian-born Canadian entrepreneur, investor and television personality. He founded BRAK Systems and Herjavec Group, became a longstanding Shark Tank investor, and serves as a Cyderes board member, advisor and investor.Open the full entry and Daymond JohnDaymond JohnDaymond John is an American entrepreneur, investor and television personality. He founded and serves as CEO of streetwear brand FUBU and brand strategy consultancy The Shark Group. An original investor on ABC’s Shark Tank, which premiered in 2009, he was appointed a Presidential Ambassador for Global Entrepreneurship in 2015 and founded Black Entrepreneurs Day in 2020.Open the full entry as its original five investors. The show’s listing described him as a venture capitalist.⁠[26]

In August 2009, O’Leary joined CBC News Network and launched the business program The Lang & O’Leary Exchange with Amanda Lang, his longtime colleague at BNN, as part of the fall 2009 relaunch of Newsworld as CBC News Network; it aired on weekdays. In September 2012, one half-hour of the program moved to the main CBC Television network.⁠[27][28]

In February 2012, Jamba Juice Company announced its acquisition of Talbott Teas, a Chicago tea company that had appeared on Shark Tank, with founder Shane Talbott joining Jamba as Vice President Innovation; the announcement did not disclose financial terms. The announcement states that Talbott Teas received an offer from O’Leary on the show and that, after the broadcast, he worked with Daymond John and Barbara Corcoran on the larger deal with Jamba.⁠[29]

On August 11, 2014, the CBC announced that O’Leary would end his co-hosting of The Lang & O’Leary Exchange and his commentary role on CBC News Network, with Amanda Lang hosting a new business program that fall. Earlier that year he had announced his departure from Dragons’ Den, and he was to join Bell Media on September 1 as an on-air contributor, appearing on BNN, Canada AM and Newstalk 1010 among other shows.⁠[27][30]

Explaining his departure, O’Leary said that once CTV began airing Shark Tank in Canada, filming both shows became increasingly difficult, so he chose the one with the larger audience: Shark Tank had 9.3 million viewers in the United States, while Dragons’ Den averaged about 1.4 million the previous year. He was then still chairman of O’Leary Funds and said he spent two-thirds of his time there.⁠[31]

At the Ivey Leaders Forum on November 6, 2014, O’Leary shared advice on entrepreneurial pitches with business students. He emphasized explaining an opportunity clearly in under 90 seconds, demonstrating the team’s ability to execute and knowing key financial figures. He also identified organizational culture, customer service and sales skills as business priorities.⁠[5]

On October 15, 2015, O’Leary Funds Management LP announced that it would combine its mutual fund and closed-end fund businesses with Calgary-based Canoe Financial under the Canoe name. The O’Leary management contracts Canoe was acquiring covered more than C$800 million in investment assets, bringing the funds Canoe managed to almost C$4 billion; O’Leary was to become Vice-Chairman of Canoe, and Stanton Asset Management, led by Connor O’Brien, was retained as sub-advisor for selected strategies. O’Leary said more than 50,000 Canadians invested in his funds.⁠[32][33]

On February 17, 2016, O’Leary Funds announced that the transaction had closed, with Canoe becoming trustee and manager of the O’Leary Funds and the O’Leary Canadian Bond Yield Fund renamed the Canoe Canadian Corporate Bond Fund. The O’Leary brand was retired: the former family of 14 O’Leary mutual funds added about C$750 million to Canoe, ten of them were to merge into Canoe funds between April and July of that year, and four closed-end O’Leary funds totaling about C$100 million were also to merge into Canoe mutual funds.⁠[34][35]

As of January 31, 2016, of the 12 former O’Leary funds with track records long enough to receive a Morningstar Rating, two had three stars, two had two stars and eight had one star; the largest, O’Leary Canadian Bond Yield, held C$143 million in assets at the end of that month.⁠[35][34]

O’Leary entered the Canadian Conservative Party leadership race in January 2017. On April 26, he announced his withdrawal and endorsed Maxime Bernier. He cited insufficient support in Quebec and his assessment that this would prevent a national electoral majority as reasons for leaving.⁠[36]

At about 11:30 p.m. on August 24, 2019, Linda O’Leary was driving the family boat back to their cottage from a dinner party when it collided on Lake Joseph, in Seguin, Ontario, with a Nautique that was stopped on the water; Kevin O’Leary and a family friend were also aboard. The Nautique, owned by Irv Edwards, was operated by Richard Ruh; two of its passengers, Gary Poltash, 64, of Florida, and Suzana Brito, 48, of Uxbridge, Ontario, died, and three other people were injured.⁠[37][38][39]

On September 24, 2019, the Ontario Provincial Police announced charges against both operators: Linda O’Leary was charged with careless operation of a vessel under the Canada Shipping Act, and Richard Ruh with failing to exhibit a navigation light while underway.⁠[40]

In November 2019, relatives of Suzana Brito filed a lawsuit in Superior Court in Oshawa, Ontario, seeking C$2 million in damages from Kevin O’Leary, Linda O’Leary, Richard Ruh and boat owner Irv Edwards; the claims in the statement of claim had not been tested in court.⁠[41]

The O’Learys denied negligence and liability and asked the Federal Court to limit damages to C$1 million under the Marine Liability Act; Edwards and Ruh also denied responsibility and sought to limit damages. In May 2020, the O’Learys sued Edwards and Ruh for more than C$3 million, and the Brito family filed a counterclaim challenging the limit and seeking C$3.5 million for Suzana Brito’s death. After the O’Learys’ Federal Court motion, the related legal actions were temporarily put on hold.⁠[39]

In March 2020, O’Leary spoke publicly about the collision, saying he felt for all the victims, including his own family, that he felt “horribly for the families that lost loved ones,” and that the forensic evidence should be fully disclosed to all the families, including his.⁠[38]

In written testimony later submitted to the U.S. Senate, O’Leary said he signed a paid endorsement agreement with FTXFTXFTX was a cryptocurrency exchange founded in 2019 by Sam Bankman-Fried and Gary Wang that operated FTX.com, moved its headquarters from Hong Kong to the Bahamas in 2021 and was valued at $32 billion in January 2022. In November 2022 it filed for U.S. bankruptcy protection amid a liquidity crisis, and Bankman-Fried was later convicted of fraud and related charges. Its reorganization plan took effect in January 2025, after which the FTX Recovery Trust began paying creditors in stages.Open the full entry in August 2021. He reported approximately $15 million in compensation, plus about $3 million toward some tax obligations. He said he invested around $1 million in FTX equity and approximately $10 million in tokens held in FTX wallets.⁠[42]

On August 30, 2021, WonderFi announced the completion of its reverse takeover, with its shares to begin trading on the NEO Exchange under the symbol WNDR the next day. The announcement listed O’Leary among the company’s key strategic investors, alongside Argo Blockchain, BIGG Digital and Josh Richards.⁠[43]

On September 14, 2021, Justice Richard Humphrey, in Parry Sound court, found Linda O’Leary not guilty of careless operation of a vessel. He found that the Nautique’s navigation lights were off, while video evidence showed the O’Leary boat’s navigational lights to be clearly visible; he concluded that alcohol “played no part” in relation to the charge, and noted that the Crown had produced no expert evidence on safe boating practices or on a safe speed in the circumstances, and that the court could draw no conclusion on the O’Leary boat’s speed, including whether it was excessive.⁠[37]

On January 4, 2022, WonderFi and First Ledger Corp., the parent of Bitbuy, announced that WonderFi would acquire the Canadian crypto exchange for around C$206 million in cash and stock, with closing expected in the first quarter of 2022. O’Leary, an investor in and strategic advisor to WonderFi, called the combined management teams excellent at execution and said the deal gave WonderFi the “bandwidth, assets and licenses” to offer an institutional-grade platform. WonderFi’s name nods to his nickname, Mr. Wonderful.⁠[44]

On June 17, 2022, the four O’Shares ETFs were reorganized into newly established SS&C ALPS Advisors funds — the ALPS | O’Shares U.S. Quality Dividend ETF, ALPS | O’Shares U.S. Small-Cap Quality Dividend ETF, ALPS | O’Shares Europe Quality Dividend ETF and ALPS | O’Shares Global Internet Giants ETF — keeping their target indexes and the tickers OUSA, OUSM, OEUR and OGIG. On June 21, O’Shares announced the completion of its strategic transaction with SS&C Technologies; O’Leary, chairman of O’Shares, said he looked forward to SS&C’s added scale and enhanced distribution and that the ETFs would continue tracking the proprietary indexes O’Shares had developed, focused on quality and preservation of capital.⁠[45]

O’Leary testified before the U.S. Senate Banking Committee about FTX’s collapse on December 14, 2022. He said he had written the related equity and account assets down to zero and that the losses belonged to his wholly owned operating company, rather than partners or limited partners. He planned to investigate account records at his own expense and had applied to join the creditors’ committee.⁠[42]

His testimony described his shift from cryptocurrency skeptic to investor. He advocated a clear regulatory framework, prioritizing legislation for U.S. dollar stablecoins, and argued that FTX’s failure should not discredit blockchain technology as a whole.⁠[42]

HarvardHarvard UniversityHarvard University is a private research university in Massachusetts, established by the Massachusetts Bay Colony legislature in 1636 and named in 1639 for early benefactor John Harvard. Its principal campuses are in Cambridge and the Allston and Longwood neighborhoods of Boston. It includes Harvard College, graduate and professional schools, and the Radcliffe Institute for Advanced Study. Two governing boards share oversight. Alan M. Garber was president as of October 2026, and the endowment stood at $56.9 billion at the end of fiscal 2025.Open the full entry reported in October 2023 that O’Leary participated in an event organized by its business school and Harvard Innovation Labs. He discussed personal branding, pitches and entrepreneurial setbacks with Reza Satchu and assessed eight student ventures. Winner Crop Diagnostix received a $100,000 investment from Searchlight Capital Partners and advisory support from O’Leary.⁠[46]

WonderAds, founded by O’Leary, announced a partnership with Tatari to provide small businesses with television advertising purchases and measurement across linear television, streaming and online video.⁠[47]

O’Leary appeared in Josh Safdie’s 2025 film Marty Supreme. Distributor A24 lists him among its principal cast alongside Timothée Chalamet and Gwyneth Paltrow.⁠[48]

On January 6, 2025, Project Liberty, founded by Frank McCourt, announced that O’Leary had joined The People’s Bid for TikTok, which it led, to acquire TikTok’s U.S. assets and rebuild the platform without the existing algorithm; O’Leary’s earlier crowdfunding effort, WonderfulTikTok.com, was folded into the bid. The announcement noted that he had about 1.4 million TikTok followers.⁠[49]

That month, McCourt, Project Liberty and an investor consortium including O’Leary submitted a formal offer to ByteDance, a day before the U.S. Supreme Court was to hear ByteDance’s challenge to the law requiring it to sell TikTok by January 19 or face a ban. The value of the offer was not disclosed. O’Leary said the timing reflected concern that the justices were going into Friday’s hearing “under the assumption that the company claimed there were no American buyers.”⁠[50]

On May 13, 2025, Robinhood MarketsRobinhoodRobinhood is a financial services brand co-founded in 2013 by Vlad Tenev and Baiju Bhatt; its publicly listed parent company is Robinhood Markets, Inc., headquartered in Menlo Park, California, United States. The company has grown from commission-free mobile securities trading into crypto assets, retirement accounts, and other financial services, and trades on Nasdaq under the symbol HOOD.Open the full entry announced an agreement to acquire WonderFi for C$0.36 per share in cash, implying a total equity value of approximately C$250 million on a fully diluted basis, through a statutory plan of arrangement under British Columbia’s Business Corporations Act. WonderFi securityholders approved the deal on July 17, 2025, and the Supreme Court of British Columbia granted its final order on July 21.⁠[51]

WonderCare, the watch insurance platform founded by O’Leary, announced an exclusive partnership with The 1916 Company. Using Chubb Studio technology, the arrangement introduced ChubbChubbChubb Limited is a Swiss-incorporated insurance holding company based in Zurich that acquired The Chubb Corporation in 2016 and operates in 54 countries and territories.Open the full entry insurance options into the watch purchasing process.⁠[52]

On February 12, 2026, the Southern District of Florida awarded O’Leary $2.828 million in his case against Ben Armstrong: $78,000 for reputational harm, $750,000 for emotional distress and $2 million in punitive damages. It also denied Armstrong’s motion to set aside the default judgment. The case concerned false allegations Armstrong published in 2025 about a 2019 boating accident and disclosure of a private telephone number. The order records that O’Leary was not the driver and had not been charged with an offense.⁠[53]

O’Leary Digital, chaired by O’Leary, announced a joint venture with WestGenCo to advance Wonder Valley in Utah’s Box Elder County, while reporting permitting work in Alberta, Canada. The stated 7.5-gigawatt capacity for each location was a long-term plan.⁠[54]

On March 25, 2026, MIDA first formally presented the Stratos data center project to the Box Elder County Commissioners, followed by a full presentation at a regular commission meeting on April 22; about 1,500 people attended the special commission meeting on May 4. The county states that the project would use a closed-loop chilling system with dry cooling and no continuous water draw, drawing on existing agricultural water rights tied to the property owners selling the land rather than on the Great Salt Lake or new water sources, and would generate its own power on site using natural gas from the nearby Ruby Pipeline.⁠[55]

Box Elder County’s project record states that commissioners postponed a decision on April 27 to review nearly 3,000 public comments concerning water, infrastructure and long-term effects. On May 4 they approved related resolutions and an interlocal agreement with MIDA. This did not establish approval of every construction permit.⁠[55]

On June 1, 2026, Robinhood announced that it had completed its acquisition of WonderFi. WonderFi’s shares were expected to be delisted from the Toronto Stock Exchange at or about the close of trading on June 2, and the company expected to apply to cease being a reporting issuer under Canadian securities laws.⁠[51]

School of Hard KnocksSchool of Hard KnocksSchool of Hard Knocks is a business-interview media brand founded in 2021 by James Dumoulin, Jack Dumoulin and Joshua Smith, based in Austin, Texas. Its street interviews, long-form videos and podcast explore guests’ careers and business experiences. It also operates content services and the School of Mentors community.Open the full entry published “I Spent A Day With Shark Tank Billionaires!”, featuring O’Leary among its interviewees. The official description lists wealth building, business judgment, failure and opportunity among the discussion topics. Original video: https://www.youtube.com/watch?v=rv-GiWg_FPk (opens in a new window).⁠[56]

Azimut GroupAzimut GroupAzimut Group is an independent asset and wealth management group headquartered in Milan, with businesses spanning asset management in public and private markets, wealth management, investment banking and fintech. Its listed holding company, Azimut Holding S.p.A., trades on the Milan Stock Exchange (AZM.IM); the group operates in 20 countries and had total assets of about €158.9 billion at the end of September 2026.Open the full entry announced that it had signed a definitive agreement to acquire all of Beanstox Inc.BeanstoxBeanstox is a digital investment advisory company headquartered in Boston that was founded in 2018 by Kevin O’Leary and Connor O’Brien. Through a mobile app it offers individual investors automated portfolios built from ETFs for a monthly subscription; in September 2026 Azimut Group announced an agreement to acquire all of its shares, with closing expected in the fourth quarter of 2026.Open the full entry, an automated investment advisory app, marking its entry into the U.S. direct-to-consumer wealth management market. Beanstox was co-founded in 2018 by O’Leary and chief executive officer Connor O’Brien, with O’Leary serving as chairman; the platform is a U.S. registered investment adviser that builds automated portfolios from low-cost ETFs.⁠[57][57][57]

Closing was expected in the fourth quarter of 2026, subject to regulatory review and other customary closing conditions, including completion of a corporate reorganization and an advisory client consent process under the Investment Advisers Act of 1940; the purchase price was not disclosed. Beanstox’s current management team was to continue leading the business. O’Leary said that many Americans were not yet investing and that Azimut’s backing would help many more people get started.⁠[57][57][57]

O’Leary Digital’s project FAQ describes both the Utah and Alberta sites as being in preconstruction. The company states that development will proceed in phases, with expansion dependent on approvals, infrastructure and resources. Planned capacity therefore does not represent completed or operational facilities.⁠[58]

O’Leary’s business activities include O’Leary Ventures, O’Shares and wine brands. He also practices photography, plays guitar and publishes books on business and personal finance.⁠[3]

O’Leary Ventures partnered with North Dakota to establish Wonder Fund North Dakota, planning $45 million in investments in early-stage companies meeting State Small Business Credit Initiative requirements. The program focuses on companies’ economic contributions to the state and provides branding and marketing support to portfolio businesses.⁠[59]

In September 2017, O’Leary said he had invested in more than 40 companies over nine seasons of Shark Tank. He said his firm’s analysis showed that about 95 percent of women-led companies met their financial targets, compared with 65 percent of male-led businesses; he attributed the gap to some male founders setting unachievable targets and said he simply followed the data in choosing companies.⁠[60]

In September 2022, O’Leary said that 75% of his returns had come from companies run by women, pointing to Wicked Good Cupcakes, Basepaws and GrooveBook. He invested $75,000 in Boston baked-goods company Wicked Good Cupcakes in a 2013 episode, when the company had $150,000 in total sales at taping; an on-air update in 2016 put its sales at $10 million within three years. Less than a year after he invested $75,000 in GrooveBook, a photo-printing subscription app, it was sold to Shutterfly for $14.5 million.⁠[61]

O’Leary has written three books on money and business. The first, Cold Hard Truth: On Business, Money & Life, covers entrepreneurship, business, money and his own life; the 2012 Anchor Canada edition has 247 pages. The second, Cold Hard Truth on Men, Women & Money, was published by Doubleday Canada, an imprint of Random House of Canada; on February 4, 2013, the CBC and Doubleday Canada announced an interview and book signing for it on February 6 in the CBC’s Lower Atrium in Toronto, with the interview hosted by Dianne Buckner.⁠[1][62][63]

The third, Cold Hard Truth on Family, Kids and Money, was published by Doubleday Canada in December 2013. Following on from his previous personal finance book, it covers about fifty common money mistakes families make at each life stage from dating through retirement, addressing saving, spending, debt and credit, and suggests ways to teach children and other family members the value of money.⁠[64]

O’Leary heads O’Leary Financial Group, which includes O’Shares Investment Advisers and O’Leary Ventures. O’Shares Investments was founded by O’Leary and Connor O’Brien; it reorganized the O’Shares FTSE U.S. Quality Dividend ETF (OUSA), O’Shares FTSE Europe Quality Dividend ETF (OEUR) and O’Shares FTSE Asia Pacific Quality Dividend ETF (OASI), all traded on NYSE Arca, from FQF Trust into identically named new series of its own OSI ETF Trust, with O’Shares Investment Advisers becoming investment adviser and the previous adviser serving as sub-adviser.⁠[3][65]

O’Leary married his wife, Linda, when they both had nothing. He recalls that when their children came, the couple had to work as a team to keep the family together, and says he now tries to spend as much time with his family as he can.⁠[1]

He is the founder and chief sommelier of the wine label O’Leary Fine Wines and a member of Boston’s Hamilton Trust.⁠[3]

On November 4, 2014, Quebec’s Autorité des marchés financiers announced that the Bureau de décision et de révision had acknowledged its agreement with Gestion de fonds O’Leary. The regulator had cited a breach of a securities concentration restriction in a portfolio, failure to publish and file a timely press release on changes to a fund’s fundamental investment objectives, failure to hold required insurance coverage, and failure to notify it of changes to registration information by failing to declare that it was the subject of a counterclaim for damages; the firm agreed to pay a C$38,000 administrative penalty and confirmed that it had taken the measures needed to correct each violation.⁠[66]

O’Leary was among the celebrity promoters sued by FTX investors in the multidistrict litigation In re FTX Cryptocurrency Exchange Collapse Litigation in the U.S. District Court for the Southern District of Florida; the plaintiffs alleged that the defendants ignored red flags while serving as brand ambassadors. On May 7, 2025, U.S. District Judge K. Michael Moore dismissed 12 of the 14 claims against the promoter defendants, finding that the investors had not shown the defendants knew FTX was a fraud and that receiving payments alone did not establish a conspiracy; a claim under Florida law that they helped FTX sell unregistered securities, and a claim under Oklahoma securities law, survived. The dismissals were without prejudice, allowing the plaintiffs to amend their complaint.⁠[67][68]

Personal website: His public biography, television work and business activities. Official website: https://kevinoleary.com/ (opens in a new window).⁠[24]

O’Leary Ventures: His investment organization. Official website: https://olearyventures.com/ (opens in a new window).⁠[3][59]

His public X account is https://x.com/kevinolearytv (opens in a new window); his YouTubeYouTubeYouTube is Google’s video-sharing and creator platform, founded in 2005 by Steve Chen, Chad Hurley, and Jawed Karim and acquired by Google in 2006. Built around video uploading, viewing, and creator earnings, the platform has developed Shorts, YouTube Music, Premium, YouTube TV, and products for children, and is headquartered in San Bruno, California, United States.Open the full entry channel is https://www.youtube.com/KevinOLeary (opens in a new window).⁠[1][24]