Entrepreneurship

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Airbnb cofounder and CEO Brian Chesky
Success

Airbnb CEO Brian Chesky challenges founders with a critical question if they aspire to emulate his success

By
October 22, 2025
Businesswoman working late at night at office.
Success

It’s not 40 hours—Gen Zers don’t know how long they need to work in a week and even experts can’t decide

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October 20, 2025
Chess.com cofounder Danny Rensch
Success

Like Jeff Bezos and Howard Schultz, Chess.com’s cofounder says people doubted his vision—with a 225 million-user empire, he’s now having the last laugh

By
October 19, 2025
Left: Jeff Bezos. Right: Reid Hoffman.
Success

Billionaire bosses like Jeff Bezos and Reid Hoffman denounce work-life balance—and some think working nonstop is key to success

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October 15, 2025
This entrepreneur saw losing her desk job as ‘my ticket to freedom.’ Now her products are sold in 9,000 stores
Success

This entrepreneur saw losing her desk job as ‘my ticket to freedom.’ Now her products are sold in 9,000 stores

By
October 15, 2025
Andrew Feldman, Co-Founder and CEO, Cerebras Systems
Success

CEO of $8 billion AI company says it’s ‘mind-boggling’ that people think you can work 38 hours a week, have work-life balance, and be successful

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October 13, 2025
This millennial went from being a builder on $5 an hour to launching (and selling) Wingstop UK for $532 million—with zero restaurant experience
Success

This millennial went from being a builder on $5 an hour to launching (and selling) Wingstop UK for $532 million—with zero restaurant experience

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October 12, 2025
Scope3 CEO Brian O'Kelley
Success

Gen Z are getting fired straight out of college—but this billion dollar founder was fired 3 times in his 20s and says it was the best training

By Emma Burleigh and Orianna Rosa Royle
October 10, 2025
Multimillionaire serial entrepreneur cried the first time she made ‘real money’—but not in a good way: ‘Wealth doesn’t erase your problems. It magnifies them’
Success

Multimillionaire serial entrepreneur cried the first time she made ‘real money’—but not in a good way: ‘Wealth doesn’t erase your problems. It magnifies them’

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October 8, 2025
Author Jenny Han
Success

How ‘The Summer I Turned Pretty’ writer went from library and Olive Garden shifts to building an empire with Netflix and Amazon deals

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October 6, 2025
Jesse Itzler
Success

This multimillionaire once cleaned meat trucks for $7 an hour, but a coffee shop encounter proved ‘You’re just one move away from changing your life’

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October 6, 2025
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
October 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
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

By
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 

By
September 29, 2025

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