Entrepreneurship

Insomnia Cookies founder and CEO Seth Berkowitz
Success

Insomnia Cookies CEO made millions selling his company to Krispy Kreme, but has a warning for entrepreneurs: ‘It can be lonely, it’s a solitary life’

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October 3, 2025
Kenn Ricci and people drinking champagne on jet
Success

Flexjet’s chairman was living with his parents—then he borrowed $500 from his dad to help buy a company, and became a billionaire

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October 1, 2025
Mark Cuban
Success

Mark Cuban says his best investment of all time was still living like a student after college—including sleeping on the floor and driving a $200 broken car 

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September 29, 2025
Apryl Shackelford in her classroom with students
Success

This teacher quit crowded classrooms to run her own microschool—now she’s earning over $100K and finally doesn’t have to work a summer job

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September 28, 2025
Photo of Reid Hoffman
Success

LinkedIn’s cofounder Reid Hoffman says seeking work-life balance is a red flag that you’re ‘not committed to winning’

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September 26, 2025
Jimmy Donaldson taking a selfie
Success

MrBeast’s $5 billion empire runs on generosity—but at a cost

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September 26, 2025
Barbara Corcoran on top of the Empire State Building
Success

Shark Tank’s Barbara Corcoran says one trait tells her instantly whether an entrepreneur will flop or succeed—if you do this, you’ll ‘lose my money’

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September 25, 2025
Derrick Hayes
Success

‘Tyler Perry said something to me I’ll never forget’: Big Dave’s Cheesesteaks CEO learned a big lesson on when ‘to leave them in the sand’

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September 25, 2025
Self-made millionaire behind $4 billion Skims says it all began with a cold call to Kris Jenner: ‘I have no delusions of who gets to run a business’
Success

Self-made millionaire behind $4 billion Skims says it all began with a cold call to Kris Jenner: ‘I have no delusions of who gets to run a business’

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September 23, 2025
Mike Bloomberg
Success

Billionaire Mike Bloomberg was fired after dedicating 15 years of his career to Salomon Brothers—the next morning, he founded his media empire

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September 23, 2025
Charlie Kirk
Success

Charlie Kirk had a message for the over 2 million unemployed Gen Z NEET men: You don’t need college to make your dreams happen

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September 22, 2025
Insomnia Cookies founder and CEO Seth Berkowitz
Success

Insomnia Cookies’ CEO runs a sweets empire worth $350 million—but as a college junior he delivered cookies across campus at 2 a.m.

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September 21, 2025
Sara Blakely smiles on stage
Success

Billionaire Sara Blakely says she launched Spanx with just $5,000 from selling fax machines—and never took on a single investor: ‘I bet on myself’

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September 20, 2025
Will Shu
Success

Deliveroo CEO Will Shu turned 100-hour weeks on Wall Street into a $4 billion food empire. Now he’s cashing out with $250 million

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September 18, 2025
Sara Blakely
Success

Spanx billionaire founder kept the brand a secret—even from family—for a year. If she hadn’t, she says she’d probably still be selling fax machines

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September 16, 2025

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