Kevin O’Leary became a millionaire after selling his software company Softkey to Mattel for $4.2 billion in 1999, but says the moment felt anticlimactic.

Kevin O'Leary said on Fox News that New York City mayoral candidate Zohran Mamdani's policies will make capital, taxpayers and developers leave the city.

Shark Tank investor Kevin O'Leary says most people will never start a company, insisting that only about one in three has the grit to thrive as an entrepreneur and taste true freedom. What ...

O’Leary says he’s optimistic when he speaks to policymakers about powering the AI boom, namechecking U.S. Interior Secretary Doug Burgum, Oklahoma Governor Kevin Stitt, and Alberta Premier ...

"Shark Tank"'s Kevin O'Leary advised budding entrepreneurs to "work for 24 months in a sector you love" before launching a business.

"Shark Tank"'s Kevin O'Leary advised budding entrepreneurs to "work for 24 months in a sector you love" before launching a business.

Kevin O'Leary has expressed concern over the increasing difficulty Americans are experiencing in contributing to their 401(k) plans due to overspending.

According to O’Leary, small businesses are taking the brunt of the damage, not necessarily from looting, but from the complete collapse of foot traffic in affected areas.

Kevin O’Leary's weighing in on the Trump vs. Elon feud -- and he’s not holding back. Mr. Wonderful’s dropping truth bombs, no filter, no fluff.

“Shark Tank” investor Kevin O’Leary brushed off the significance of the public feud between President Trump and Elon Musk, saying the two men “really need each other” and will find a way ...

Kevin O’Leary said Tesla shareholders are "used to the chaos" after the company's stock price dropped as much as 17% amid Elon Musk's feud with President Donald Trump.

For one view on President Trump’s trade wars and his battle against Harvard, Amna Nawaz spoke with Kevin O’Leary, a businessman, celebrity investor and a regular on the show “Shark Tank ...