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Entrepreneurship

Page 9 of 43
Charlie Kirk
SuccessCharlie 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
SuccessInsomnia 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
SuccessBillionaire 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
SuccessDeliveroo 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
SuccessSpanx 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
YouTube founders Chad Hurley and Steve Chen
SuccessThe founders who cashed out on YouTube, Reddit, and Instagram—and missed out on becoming today’s billionaires
By Preston ForeSeptember 13, 2025
Sebastian Siemiatkowski
SuccessKlarna’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
By Preston ForeSeptember 12, 2025
YC co-founder who backed Airbnb, Dropbox, and Reddit says high school isn’t the time to launch a startup
SuccessYC co-founder who backed Airbnb, Dropbox, and Reddit says high school isn’t the time to launch a startup
By Jessica CoacciSeptember 8, 2025
Mick Hunt
SuccessThis 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
By Preston ForeSeptember 6, 2025
Jensen Huang signs with a marker.
SuccessNvidia 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 RoyleSeptember 5, 2025
Big Dave's Cheesesteaks CEO and founder Derrick Hayes
SuccessMultimillion-dollar restaurant CEO splurged on Range Rovers and McLarens—but now he’s ‘mindful’ about spending because the economy is unpredictable
By Emma BurleighSeptember 5, 2025
Big Dave's Cheesesteaks founder and CEO Derrick Hayes
SuccessBig Dave’s Cheesesteaks CEO grew up in ‘survival mode’ selling newspapers and bean pies—now his chain sells a $12 cheesesteak every 58 seconds
By Emma BurleighAugust 30, 2025
Photo of Dani Reiss
SuccessCanada Goose’s ‘nepo baby’ boss avoided printing CEO on business cards for 10 years after taking over his grandfather’s business at 27
By Orianna Rosa RoyleAugust 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
By Emma BurleighAugust 17, 2025
Keyvan_Mohajer headshot
SuccessSoundHound’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’
By Preston ForeAugust 16, 2025
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Success
Now worth $200 million, Sarah Jessica Parker credits being ‘one of eight kids that struggled financially’ for her hunger, ambition, and work ethicplaceholder alt text
By Orianna Rosa RoyleJune 24, 2026
Success
MacKenzie Scott alone accounted for one-third of America's $19.2 billion in megagifts last yearplaceholder alt text
By Sydney LakeJune 25, 2026
Retail
Amazon's record Prime Day masks a darker truth: Americans are spending more and getting lessplaceholder alt text
By Nick LichtenbergJune 24, 2026
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