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Quick answers
Did Anand Dhillon co-found Cover?
Yes. Y Combinator's company page for Cover, checked 2026-10-15, lists its founders as Karn Saroya (Founder/CEO), Anand Dhillon (Founder) and Natalie Gray (Founder/Design), in the Winter 2016 batch. TechCrunch's 2018-10-02 story on Cover's US$16 million Series B says Saroya went to high school with Anand Dhillon and that Saroya and his co-founders have deep ties.
Is he Canadian?
Yes. Techvibes' 2017-07-14 report on Cover's US$11 million in funding, now hosted by BrainStation, describes Karn Saroya and Anand Dhillon as Canadian entrepreneurs and former Shopify employees. TechCrunch (2018-10-02) says the team's previous startup, the fashion marketplace StyleKick, was acqui-hired by Shopify. Natalie Gray's TechTO talks describe Cover running offices in San Francisco and Toronto; see the Cover page.
What happened to Cover?
It wound down in 2022, terminating all but a handful of staff in June that year after funding and acquisition efforts failed and moving its policyholders to another insurer; see the Cover page. Directory listings describe Dhillon as a co-founder of Re, the onchain reinsurance protocol Saroya started afterwards, but Re's own press page, checked 2026-10-15, does not name him, so this profile does not list a current role. No public page states where he lives, so no city is listed.
Has Dhillon spoken at TechTO?
No. Co-founder Natalie Gray presented Cover on the TechTO stage twice in 2018, and Karn Saroya spoke in February 2020; Dhillon has not taken a TechTO stage.