Entrepreneurship

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YouTube founders Chad Hurley and Steve Chen
Success

The founders who cashed out on YouTube, Reddit, and Instagram—and missed out on becoming today’s billionaires

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September 13, 2025
Sebastian Siemiatkowski
Success

Klarna’s cofounder worked at Burger King and lived on welfare before starting the buy-now, pay-later firm. It’s now worth $16 billion after IPO

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September 12, 2025
Mike Repole sits in front of a microphone
Success

Billionaire who sold two companies to Coca-Cola says he tries to convince people not to become entrepreneurs: ‘Every single day, you can go bankrupt’

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September 12, 2025
YC co-founder who backed Airbnb, Dropbox, and Reddit says high school isn’t the time to launch a startup
Success

YC co-founder who backed Airbnb, Dropbox, and Reddit says high school isn’t the time to launch a startup

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September 8, 2025
Mick Hunt
Success

This podcaster went from a top insurance salesman to #1 on Apple Podcasts making $7 million a year. He tells Gen Z they just need a phone to copy him

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September 6, 2025
Jensen Huang signs with a marker.
Success

Nvidia CEO Jensen Huang sent research reports on Sundays to SoundHound’s CEO for feedback—an unusual ritual that helped grow the $5 billion AI firm

By Preston Fore and Orianna Rosa Royle
September 5, 2025
Big Dave's Cheesesteaks CEO and founder Derrick Hayes
Success

Multimillion-dollar restaurant CEO splurged on Range Rovers and McLarens—but now he’s ‘mindful’ about spending because the economy is unpredictable

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September 5, 2025
Big Dave's Cheesesteaks founder and CEO Derrick Hayes
Success

Big Dave’s Cheesesteaks CEO grew up in ‘survival mode’ selling newspapers and bean pies—now his chain sells a $12 cheesesteak every 58 seconds

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August 30, 2025
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
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
Keyvan_Mohajer headshot
Success

SoundHound’s millionaire boss founded 3 software startups before even graduating—he tells Gen Z who want to be their own boss ‘don’t just throw darts randomly’

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August 16, 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
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

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