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The Latest Breaking News from Kevin OLeary

Kevin O'Leary Says Business School Teaches You Nothing Until Reality Hits — Reveals How He Learned The Hard Way And Now Spots Winners Quickly

Disclosure: The article was originally published on Benzinga.com on June 19, 2025.

Benzinga

Shark Tank's Kevin O'Leary: Why 'Mr. Wonderful' Says Being Liked Is Overrated in Leadership — Lessons from Steve Jobs

Kevin O'Leary, 'Mr. Wonderful' of Shark Tank, explains why respect and results matter more than likability in leadership, drawing from Steve Jobs' example.

International Business Times UK

Trump Trade Push 'Very Honorable,' Says 'The Big Short' Investor Steve Eisman — He's Fixing Clinton-Era Mistakes

Investor Steve Eisman, made famous by the 2015 movie “The Big Short,” says that he views President Donald Trump’s current trade and tariff regime as both justified and long overdue.

Benzinga

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Mark Cuban Tells Governors Not To Let The Federal Government Take TikTok—'It'll Only Get Worse'

Billionaire entrepreneur Mark Cuban recently told state leaders to push back against federal control of social media app TikTok, warning, “Don't let the federal government take it. It'll only get worse.”

Benzinga

Kevin O’Leary Says You Need a Prenup — Even If You’re Not Rich

Prenups aren’t just for the wealthy. Kevin O’Leary explains why every couple should protect their finances before marriage.

GOBankingRates

The 'Only Thing' That Charlie Munger Got Wrong Was This, Says Kevin O'Leary — But Credits Warren Buffet Ally For Shaping His Investing Style

Kevin O’Leary, a prominent investor and a regular on “Shark Tank,” has recently expressed his disagreement with the late Charlie Munger‘s views on certain investment avenues.

Benzinga

Mark Cuban Says Trump's Nvidia, AMD Export Tax Is What Warren, AOC, Sanders Should've Done — Kevin O'Leary Calls It 'Blackmail'

Mark Cuban and Kevin O’Leary have weighed in on President Donald Trump’s controversial deal with Nvidia Corporation (NASDAQ:NVDA) and Advanced Micro Devices, Inc. (NASDAQ:AMD), with Cuban praising it as a progressive move and O’Leary calling it corporate “blackmail.”

Benzinga

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‘Shark Tank’ star Kevin O’Leary says being liked has nothing to do with success—Steve Jobs taught him: 'You can't worry about whose feelings you bruise'

The multimillionaire investor told Fortune that he learned from working with the late Apple CEO that embracing a “founder’s mindset” involves tough love. “You're going to fail for sure” if you worry about being liked.

Fortune

'Shark Tank' Investor Rashaun Williams Says Gen Z Can Retire Millionaires—If They Ditch This One Habit

A growing number of young Americans are anxious about their financial future — and many are turning to doom spending as a way to cope. However, venture capitalist and "Shark Tank" guest judge Rashaun Williams says Gen Z can still retire as millionaires by following a simple, disciplined approach, Fortune…

Benzinga

‘You’re Becoming a Watch A**hole’: Why Kevin O’Leary Went From Wearing One-Of-A-Kind Watches to ‘Inspiring Young People’

In a candid and surprisingly self-aware moment during a recent Brew Markets interview, O’Leary recalled a confrontation on the Shark Tank set that permanently changed how he thinks about watches — and the message he sends by wearing them.

Barchart

Multimillionaire Rashaun Williams landed a seat next to Mark Cuban on ‘Shark Tank’ by sneaking into events he wasn’t invited to and saying ‘hear me out’

The venture capitalist admits his secret for success hasn’t always been following the norms—but rather manifesting his dreams.

Fortune

‘I Wear Six Pieces a Day’: Kevin O’Leary Wears a Dozen Watches Every Two Days Worth Nearly $1,000,000

In a recent interview with Brew Markets, O’Leary revealed that he doesn’t just collect watches — he lives them.

Barchart

22 Shark Tank Products That Are Either Pure Genius Or Absolutely Unhinged

Get ready for a tour of the best and worst ideas that brave entrepreneurs dared to pitch on Shark Tank.

Bored Panda

Kevin O'Leary Says He Moved To Florida Despite Owning A House In Boston Due To Elizabeth Warren, Lambasts Senator For Supporting Zohran Mamdani

‘Shark Tank’ investor Kevin O'Leary said he decamped to Florida despite still owning a home in Boston because of Sen. Elizabeth Warren (D-Mass.), and blasted the Massachusetts Democrat for backing New York City mayoral nominee Zohran Mamdani.

Benzinga

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Benzinga

Kevin O'Leary Says People Are Wrong To Think That 'Likability' Matters: 'I'm Not Here To Make Friends, I'm Here To Win'

The renowned investor and television personality Kevin O'Leary is doubling down on his unapologetically blunt leadership style, arguing that success is built on execution, not popularity.

GOBankingRates

What Kevin O’Leary Says Shoppers Should Expect From Walmart and Trump’s Tariffs

Here's what "Shark Tank" investor Kevin O'Leary had to say about what customers can expect from Walmart amidst tariffs.

Benzinga

Kevin O'Leary Rejects Trump's Tariff Rebate Plan, Says Taxpayers Want To See The National Debt Paid Down

President Donald Trump recently suggested that revenue from tariffs could be returned to Americans in the form of rebate checks. He floated the idea as a way to give back to "people of a certain income level," noting that the U.S. is generating "so much money" from tariffs.

Benzinga

Kevin O'Leary Slams Trump for 'Whacking' BLS Chief After Disappointing Jobs Report: 'You Don't Shoot the Messenger' [CORRECTED]

Editor’s Note: This article has been updated to correct a misspelling of Dr. McEntarfer’s name.

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Benzinga

Kevin O'Leary Defends Trump's Tariffs As Markets Shrug Off Hikes: 'I'm An Investor. I Don't Listen To All The Noise'

Investor and entrepreneur Kevin O'Leary backed Donald Trump's aggressive new tariffs, saying markets care about policy—not political noise—and that capital is still flowing into the U.S. economy.

Benzinga

'Shark Tank' Star Kevin O'Leary's Main Motivation Is Proving His Haters Wrong, Not Making Money

"Shark Tank" investor Kevin O'Leary has a simple secret for staying motivated: he loves proving people wrong. "I just love it when people tell me, ‘Oh, you can't do this, you can't do that,'" O'Leary recently told Fortune.

Benzinga

Kevin O'Leary Backs Trump's Tariff Strategy: Calls It a 'Value-Added Tax,' Says He Can Be 'Very Pragmatic'

Investor and television personality Kevin O’Leary, AKA “Mr. Wonderful,” came out in defense of President Donald Trump’s trade and tariff policies, framing them as a strategic response to global trade imbalances.

Fortune

Gen Z can retire as millionaires, ‘Shark Tank’ star Rashaun Williams says—they just need to quit doom spending and follow his 3 tips

Gen Z is watching boomers unretire and doom spending their money in despair—but seven-figure wealth is entirely achievable, the multimillionaire ‘Shark Tank’ star Rashaun Williams tells Fortune.

Benzinga

Kevin O'Leary Says All 54 Of His Small Businesses Are Using AI To Cut Costs, Stay Competitive Amid Tariffs

Kevin O'Leary, also known as "Mr Wonderful," says artificial intelligence is helping businesses like his fight inflation and survive margin pressure brought on by new tariffs.

Benzinga

Kevin O'Leary Says The 'Tariff Drama' Is Settling And The Market's Calming Because Trump 'Found The Loophole'

Investor Kevin O’Leary, better known as “Mr. Wonderful” from the “Shark Tank” TV show, believes the U.S. market is stabilizing despite recent trade tensions because President Donald Trump has figured out a workaround on tariffs.

International Business Times UK

Kevin O'Leary Says This $28 Purchase Is a Waste if You Make $70K—Here's What He Says to Buy Instead

Kevin O'Leary Says Spending $5 a Day on Takeaway Coffee Adds Up Fast—Urges $70K Earners to Invest Instead and Build Long-Term Wealth

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