Open this photo in gallery Kevin O'Leary is pictured in Burlington, Ont. on April 26, 2017. Mr. O'Leary said he wanted to pay back small vendors out of his own pocket, but because of campaign contribution limits, he is not legally allowed. Fred Lum/The Globe and Mail

Kevin O’Leary sold fewer than half of the available tickets to a fundraising event intended to pay off the $530,000 debt remaining from his failed federal Conservative leadership bid.

By the time the event began on Thursday, organizers estimated about 100 of the 250 tickets – priced at $2,000 each – had sold for the evening event, which was held at historic Casa Loma in Toronto.

“The big challenge I had from the beginning was, what would motivate anybody to help me pay down campaign debt, or any candidate frankly?” Mr. O’Leary said in an interview before the event began. “This is one of the criticisms I have of the system.”

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Mr. O’Leary is a celebrity businessman best-known for his stints on the entrepreneurial TV shows Dragons’ Den and the U.S.-made Shark Tank.

He said he wanted to pay back small vendors out of his own pocket, but because of campaign contribution limits, he is not legally allowed. “If I have the capital, make me pay it. It’s just wrong. It’s un-Canadian, that’s what it is,” he said.

But Mr. O’Leary said he’s not disappointed with the ticket sales, which will total around $180,000 to $200,000. He has pledged to match all ticket sales with donations to charities and other causes.

Mr. O’Leary sought to attract donors to the event by using a taxpayer-funded program for Olympic athletes. As part of his sales pitch, Mr. O’Leary promised to match the $2,000 ticket price with an equivalent donation to the Canadian Olympic Foundation.

Mr. O’Leary said the federal government will also match the $2,000 contribution through its NextGen program to fund future Olympic and Paralympic athletes.

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On Thursday, Mr. O’Leary said he’ll also be making donations to causes chosen by ticket holders, including Sanctuary Ministries of Toronto, which helps the homeless; the Montreal Children’s Hospital; and the Rotman School of Management at the University of Toronto.

At the event, called Three Sharks in a Castle, Mr. O’Leary took the stage with two of his American TV co-stars, real estate mogul Barbara Corcoran and billionaire Mark Cuban, co-owner of the NBA’s Dallas Mavericks, for a discussion about entrepreneurship, the global real estate market, the #MeToo movement and Mr. Cuban’s “potential bid for the presidency of the United States of America” as an independent candidate.

The well-heeled crowd, many holding glasses of wine, sat in white chairs and cheered as the trio took the stage. Many audience members thanked the special guests for attending in a Q&A.

In an interview, Mr. Cuban said Mr. O’Leary is a friend and he was happy to help him. But neither he nor Ms. Corcoran said they were aware the event wasn’t sold out.

“We’re not as much of a draw as we hoped we would be,” Mr. Cuban said with a laugh. “I’m here to help Kevin, that’s all I care about.”

Ms. Corcoran said she never understood why Mr. O’Leary ran for political office.

“I thought he was crazy, honestly,” Ms. Corcoran said in an interview. “Because I think Kevin, above all, loves business. And you don’t have room in your life for two great loves.”

One guest at the event, Crispin Pereira, said he attended because his brother works for Mr. O’Leary, but he is also a fan of Shark Tank.

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Another attendee, Bill Pallett, who runs a consulting business, said he was interested in seeing the TV stars discuss business issues on a more personal level. He said he was aware the event was to pay off Mr. O’Leary’s debt. “It’s like anything – if you’re getting value for money, it’s an honest approach,” Mr. Pallett said.

Mr. O’Leary dropped out of the Conservative leadership race last year before the final vote and endorsed Maxime Bernier, citing the reason as a lack of support in Quebec. Mr. O’Leary said he learned a lot during his run – including that you can’t win a race through social media alone.

“I made assumptions. I was wrong,” Mr. O’Leary said.

Mr. O’Leary said he still maintains an interest in politics. He said he voted for Doug Ford in the Ontario Progressive Conservative leadership race and will vote for him in the June election.

According to Elections Canada records, unpaid claims from Mr. O’Leary’s campaign total $529,184, with nearly $200,000 coming from the candidate himself. He has pledged to pay back vendors before he pays back himself.

Candidates can only contribute $25,000 to their own campaigns, but they are allowed to be suppliers to their own campaigns and may use their own funds to pay for personal expenses as long as they are repaid by the campaign within three years of the end of the race.

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The maximum annual donation to a leadership campaign is $1,575, but Elections Canada rules allow for a higher ticket price to help cover the expenses of the event.

Attendees at the fundraiser will receive a tax credit of $650.

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