On April 8, Phillips’ New York Spring Session came to a close. On this occasion, the auction house—renowned for its prestigious watch collections—announced a partnership with the specialized insurance company WonderCare, the latest venture from Canadian serial entrepreneur and collector Kevin O’Leary.
Kevin O’Leary, President of Leary Ventures and Beanstox, made his fortune in the consumer software industry. He has also built a strong reputation as an avid collector of high-end timepieces.
In 2024, he conceived the idea of launching the first insurance company designed for watch collectors.
Two years after its launch,WonderCare—as it is called—has just scored another major coup by becoming thepartner for Phillips’ New York Session Spring 2026 online auction, the epicenter of prestigious watch auctions since 2015.
Comprehensive, borderless insurance
The latest Phillips New York Sessions once again highlighted independent manufacturing, mechanical complexity, and provenance over mere brand recognition. The star lot of this spring edition, an F.P. Journe Centigraphe Souverain, with an estimate ranging from $80,000 to $160,000, sold for $355,600—more than double its high estimate. Meanwhile, an F.P. Journe Automatique Lune Havana sold for $190,500, while an Audemars Piguet Royal Oak Perpetual Calendar went under the hammer for $139,700, placing them in second and third place on the podium, respectively.
The auction house and private sales firm chose this occasion to partner with Wondercare real-time insurance coverage, which offers a streamlined process for collectors wishing to protect their new acquisitions. Its implementation draws on the expertise of Bacs & Russo.
Integrated into the Phillips experience, WonderCare already allows U.S. buyers to access real-time quotes, digital policy management, and global coverage, all backed by the Chubb insurance and reinsurance consortium.
Thus, Kevin O’Leary’s latest venture aims to modernize the collecting experience. On one hand, this new offering allows Phillips to add a service-oriented feature to its shopping experience. On the other, WonderCare can position itself at a key moment in the product lifecycle to remove barriers: the acquisition phase.
On its website, the platform presents itself as comprehensive insurance tailored to the evolving needs of luxury clients. It offers protection against loss, theft, or damage with no deductible, unlike traditional home insurance policies limited to $5,000 or less.
A response to a pressing need
Buying the watch of your dreams at auction has never been a problem, provided you have the necessary funds. Insuring it, however, is a much more complex matter.
This is particularly ironic in an increasingly uncertain world, where beautiful watches attract covetous eyes and where social media makes their wearers easy targets—both at home and out on the street.
A study by the Franco-Swiss startup Grace published in late 2025 cited fear of theft, loss, and damage as the main barrier to purchasing a luxury item (51% of respondents).
A avid collector, Kevin O’Leary learned this the hard way. Like many, he had added riders to his home insurance policy covering watches, jewelry, and works of art.
The year following a theft, he discovered that his home insurance premium had skyrocketed, even though only watches had been stolen and the property had suffered no substantial damage.
He then pinpointed a widespread problem that the industry had never addressed until now: why is it that when a collectible is stolen, its value depreciates when it should be the opposite?
“Most home insurance policies—or a significant number of them—provide for a depreciation in the value of the insured item. In the case of a watch like a Rolex Daytona, the price should appreciate year after year. Yet, you won’t be able to replace it if you lose it in five or ten years, nor if it’s stolen the very day after purchase.”
With 8 million followers across all his platforms, the businessman wanted to raise awareness among his audience and see if there was a business opportunity there. The results were immediate:of the 800 inquiries he expected from his 15-second sponsored ad, he received… 3,500!
Thus, after three years of development, WonderCare was launched in 2024.
Its concept is to allow watch collectors to insure part of their collections for an annual cost of 1.7% to 2.1% of the watch’s value.
“We stand out by focusing first and foremost on the end-to-end experience of watch enthusiasts, andwe are expanding into other luxury assets such as fine jewelry, designer handbags, art, and collectibles.” explains its website.
As the founder likes to repeat, his insurance only makes sense for owners who don’t keep their watches in a safe and who travel frequently.
Designed at launch for the American public, the platform was already looking ahead to the United Arab Emirates and Europe.
Read more > Fear of theft is holding back luxury purchases
Featured photo: © Phillips
