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Entrepreneurship

Page 9 of 44
Chess.com cofounder and chief chess officer Danny Rensch
Success
How the cofounder of Chess.com went from being a child prodigy in a religious cult to building a 225 million player empire
By Emma BurleighOctober 5, 2025
Photo of 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’
By Emma BurleighOctober 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
By Emma BurleighOctober 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 
By Jessica CoacciSeptember 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
By Preston ForeSeptember 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’
By Preston ForeSeptember 26, 2025
Jimmy Donaldson taking a selfie
Success
MrBeast’s $5 billion empire runs on generosity—but at a cost
By Preston ForeSeptember 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’
By Preston ForeSeptember 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’
By Emma BurleighSeptember 25, 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
By Emma BurleighSeptember 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
By Preston ForeSeptember 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.
By Emma BurleighSeptember 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’
By Dave SmithSeptember 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
By Preston ForeSeptember 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
By Preston ForeSeptember 16, 2025
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Success
Ex-PepsiCo CEO Indra Nooyi worked from midnight until 5 a.m. as a receptionist to pay for her Yale degree—and she says ‘respect went up’ because of itplaceholder alt text
By Preston ForeJuly 6, 2026
AI
Shark Tank's Kevin O'Leary says if he were 25 today, he'd chase these two booming opportunities in the world of AIplaceholder alt text
By Marco Quiroz-GutierrezJuly 5, 2026
Newsletters
Iran strikes 85 U.S. military sites in the Gulf, sparking a global selloff in stocks and a spike in the price of oilplaceholder alt text
By Jim EdwardsJuly 8, 2026
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