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The Latest Breaking News from Kevin OLeary

Kevin O'Leary became a millionaire from a $4.2 billion deal—but said it was 'very anticlimactic'

The Shark Tank star and Mr. Wonderful says hitting his first million after selling Softkey to Mattel for $4.2 billion felt like a blip—and every millionaire and billionaire he knows agrees.

Fortune

How Much Richer Kevin O’Leary Has Gotten Over the Last 5 Years

When it comes to O'Leary's fortunes and how his wealth has changed over the past few years, it's not as simple as you may think to find exact figures.

GOBankingRates

Kevin O'Leary Predicts Who Will Control the Strait of Hormuz After the Middle East War Subsides

Kevin O'Leary predicts a multinational coalition will seize control of the Strait of Hormuz to ensure energy security after the 2026 Middle East war. US Treasury Secretary Scott Bessent considers 'unsanctioning' 140 million barrels of Iranian oil to curb soaring global prices.

International Business Times UK

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How star of Oscar-nominated film lost $1000 at Sunday’s ceremony

IN FULL

The Independent UK

Kevin O'Leary Placed A Big Bet On Marty Supreme's Timothèe Chalamet Winning Best Actor. How Much Did He Lose?

That's no small amount of change.

Cinemablend

Marty Supreme star Kevin O’Leary bet $1,000 on Timothée Chalamet’s Oscar win – and lost

‘Marty Supreme’ star lost out on the Best Actor award to ‘Sinners’’ Michael B Jordan

The Independent UK

Timothee Chalamet's Mary Supreme co-star loses bet after star fails to win Best Actor Oscar

Timothee Chalamet's Marty Supreme co-star, Kevin O'Leary, is $1,000 down after Timothee Chalamet lost out on Best Actor at the Academy Awards.

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Conan’s bits, O’Connell’s fangs and Jafar Panahi unimpressed: Oscars 2026 viral moments

In a year that largely stuck to script, host O’Brien’s antics and the It Was Just an Accident director’s stare at Kevin O’Leary got the internet talking

The Guardian - US

Kevin O'Leary's Oscars Chain Is Another Trading Card With An Eye-Watering Price

It costs a pretty penny.

Cinemablend

Oscars 2026: The most questionable celebrity looks on the red carpet

From Kevin O’Leary’s confusing NBA card necklace to ‘Sinners’ star Jayme Lawson’s candlestick-shaped dress, these were the most divisive looks on the carpet

The Independent UK

'What a waste of money': Shark Tank star Kevin O'Leary urges couples to ditch the extravagant wedding and do this instead

The investor says dropping big money on a honeymoon vacation is also "really stupid.”

Fortune

Here's Why Billionaires Like Elon Musk, Mark Zuckerberg Use Mortgages to Buy Mansions

Billionaires like Elon Musk and Mark Zuckerberg choose to take out mortgages despite their immense wealth to leverage tax breaks and use their free cash for better opportunities.

International Business Times UK

1 in 5 Gen Z job seekers are bringing mom or dad to interviews—and some are even letting them negotiate their salary with the boss

Facing a brutal job market, some Gen Z candidates are bringing mom or dad to job interviews—or even letting them negotiate their pay. Employers say it’s a major red flag.

Fortune

KISS Co-Founder Gene Simmons Tells Hollywood Stars Like Ben Stiller and Mark Ruffalo to 'Shut the F*ck Up' Over Politics

Gene Simmons criticises Hollywood celebrities like Ben Stiller and Mark Ruffalo for commenting on politics, urging them to focus on their art.

International Business Times UK

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Fortune

Kevin O'Leary doesn't care if you work from your basement. He just wants to know if you can ‘execute’

Companies forcing workers back to the office are potentially giving up their best talent, he said.

Fortune

Ring is one of the largest companies ever to come out of Shark Tank. Its CEO says he prepared for his pitch like an Olympic athlete

Jamie Siminoff’s Olympic-level prep turned a rejected offer into a $1 billion exit.

Fortune

Shark Tank's Kevin O'Leary says if he were 25 today, he’d chase these two booming opportunities in the world of AI

O'Leary says young entrepreneurs shouldn't chase flashy AI, they should instead try to build its backbone.

International Business Times UK

Kevin O' Leary Backs Large-Scale Data Centre Projects in US, Canada to Provide Gigawatts of AI-Ready Power

Shark Tank's Kevin O'Leary is spearheading data centre projects in the US and Canada, aiming to deliver up to 15 GW of power for AI and cloud computing.

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GOBankingRates

The Dumbest Financial Advice From Millionaires That Could Cost You Money

From investing myths to bad money tips, GBR breaks down why popular financial advice from millionaires can be misleading, outdated or wrong.

Fortune

‘That résumé goes right into the garbage’: Kevin O’Leary says it’s a ‘horrific signal’ for Gen Z to bring their parents to job interviews

A 2025 study showed 77% of surveyed Gen Z job seekers have brought a parent to a job interview.

Fortune

Amazon Ring's founder is back with a hard pivot to AI. How Jamie Siminoff went from 'Shark Tank' reject to $1 billion brand

Ring’s founder wants to get the company back to his original vision.

The Conversation

Cameos in ‘Marty Supreme’ ask audiences to dig deeper

In the lead-up to Oscar season, Josh Safdie, the director of Marty Supreme, has been elaborating on the many cameos in his film that build on real-world associations to create a rich cast of characters.

Reason

Mr. Wonderful v. BitBoy Crypto: Shark Tank's Kevin O'Leary Awarded $2.8M in Defamation Suit

Defendant has apparently "informed his psychiatrist ... that he believes he is dead and in a waiting room for Hell."

We Got This Covered

Kevin O’Leary claims an average American ‘does not give a damn’ about Epstein

Actually, average Americans do give a damn. But people like O’Leary clearly don’t.

The Independent UK

Mark Ruffalo leads celebrity backlash against Kevin O’Leary after attack on Billie Eilish’s anti-ICE speech

Millionaire warned music and movie stars to ‘shut your mouth and entertain’ after Eilish used Grammy acceptance speech to speak out against ICE

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