Entrepreneurs

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Photo of Alexis Ohanian
Success

Millionaire Alexis Ohanian walked out of the LSAT 20 minutes in, went to a Waffle House, and decided he was ‘gonna invent a career.’ He founded Reddit

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August 27, 2025
Tommy Fleetwood of England celebrates with the Fedex Cup trophy after winning the final round of the TOUR Championship 2025 at East Lake Golf Club on August 24, 2025 in Atlanta, Georgia.
Success

Tommy Fleetwood finally snapped his historic winless streak—163 consecutive PGA Tour losses—and got $10 million richer in the process

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August 27, 2025
Brian Chesky
Success

Airbnb CEO Brian Chesky says he’s still in founder mode—he personally handpicks staff, treats them as direct reports, and decides who stays

By Jessica Coacci and Orianna Rosa Royle
August 26, 2025
Photo of Lior Lewensztain
Success

Gen Z want ‘secure’ jobs in health care—but this CEO left the industry after realizing he could make millions getting Americans to eat more fruit

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August 22, 2025
OpenAI’s chairman says ChatGPT is ‘obviating’ his own job—and says AI is like an ‘Iron Man suit’ for workers
AI

OpenAI’s chairman says ChatGPT is ‘obviating’ his own job—and says AI is like an ‘Iron Man suit’ for workers

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August 20, 2025
This millennial gut health scientist and founder juggles 5 jobs and 2 kids—she has a ‘strict’ coffee routine and swears by $20-a-day lunch habit
Success

This millennial gut health scientist and founder juggles 5 jobs and 2 kids—she has a ‘strict’ coffee routine and swears by $20-a-day lunch habit

By
August 20, 2025
Photo of Dani Reiss
Success

Canada Goose’s ‘nepo baby’ boss avoided printing CEO on business cards for 10 years after taking over his grandfather’s business at 27

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August 18, 2025
Fredrik Eklund
Success

‘Million Dollar Listing’ star used to sling paninis, but now leads a team closing $15 billion in deals—because someone was ‘stupid enough’ to hire him

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August 17, 2025
A Gen Xer sold his company for $1.6 billion. He kept less than $100 million and gave the rest away because he doesn’t ‘believe in billionaires’
Success

A Gen Xer sold his company for $1.6 billion. He kept less than $100 million and gave the rest away because he doesn’t ‘believe in billionaires’

By
August 15, 2025
Photo of Kevin O'Leary
Success

‘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’

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August 10, 2025
Gen Z dropouts could be your future boss: 20-somethings without degrees are leading the side gigs economy
Success

Gen Z dropouts could be your future boss: 20-somethings without degrees are leading the side gigs economy

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August 6, 2025
Eventbrite CEO Julia Hartz
Success

Eventbrite’s CEO walked away from Hollywood to build a $225 million ticketing company with her own money: ‘If it’s a disaster, we’ll just be broke’

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July 30, 2025
Kevin O'Leary
Success

‘Shark Tank’ icon Kevin O’Leary reveals the 3 things he looks for when investing his millions into a founder

By
July 27, 2025
Gen Z corporate worker annoyed at office
Success

It’s not just Gen Z: these founders hated their 9-to-5 so much they launched their own companies

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July 25, 2025
Billionaire entrepreneur Mark Cuban
Success

Billionaire Mark Cuban reads around 700 emails every day in his quest for near inbox zero—and prefers that to ‘boring’ meetings

By
July 23, 2025

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