Known as Mr. Wonderful from "Shark Tank" and the signature timepieces he wears with a red watch band, venture capitalist Kevin O'Leary has learned the hard way how to protect his collections.

O'Leary has had two of his personal watch collections stolen over the years, prompting him to become a critic of the traditional insurance market and leading him to launch his own specialized insurance platform.

He said that putting a watch on your home policy doesn't always work because they insure for the depreciated value of the timepiece.

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"When you buy a Rolex for $17,000, 10 years later it's worth 58," he said in a video recently posted on X. "You need to be insured for the replacement value."

O'Leary said his WonderCare Luxury Insurance platform can generate a policy in nine seconds using artificial intelligence. The AI pulls global auction data every 24 hours so customers remain protected at replacement value. 

The cost to insure high-end watches through WonderCare ranges from $43 per year for a Tudor Black Bay Fifty-Eight valued at $3,625 to $866 per year for a Patek Philippe 5172G worth $73,700, according to the insurance platform's website.

WonderCare policies protect against loss, theft or damage with no deductible, unlike a typical homeowner's policy, according to the company's website. 

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Many people who commented on the post were critical of O'Leary's expensive watch-collecting hobby, with one person posting, "What a gluttonous thing to own."

Another questioned the wisdom of investing in watches, posting: "I thought you were about making money, not throwing it away on watches. Oh wait, you're not the pansy, we are." 

Others indicated that WonderCare is something they could use themselves and appreciate fine watches. 

"It's nice to see him doing some thing that shows care for other people and their thing especially those beautiful watches I've seen those watch collections he gets it in not everybody knows a good time piece it's becoming a lost art," another person commented.

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Because he's been robbed of his watch collection more than once, O'Leary spreads his watch collection across nine cities, each with its own vault.

O'Leary, who has said he wants to be buried with his watch collection, draws a line between collecting for sentiment and investing for returns, arguing that watches "mark time" by commemorating life's major milestones — from a major business deal to a graduation. 

Despite his penchant for five- and six-figure timepieces, he offers a fundamental rule for aspiring collectors: "The real rule is — never borrow money to borrow a watch, ever. Just buy a watch you can afford," he told Money.ca. 

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