Entrepreneurs

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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
September 21, 2025
David Adelman
Commentary

I turned my $2,000 bar mitzvah money into a $2 billion student housing company. Here’s what I learned

By
September 20, 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
September 20, 2025
Brineworks wind plant.
Energy

Exclusive: Climate-tech startup Brineworks raises $5.87 million

By
September 19, 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
September 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
September 16, 2025
Meet a 23-year-old electrician who was a ‘good student’ but skipped college to join Gen Z’s blue-collar revolution. He makes 6 figures
Success

Meet a 23-year-old electrician who was a ‘good student’ but skipped college to join Gen Z’s blue-collar revolution. He makes 6 figures

By
September 14, 2025
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

By
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

By
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’

By
September 12, 2025
Burned out
Commentary

We studied America’s entrepreneurs and found too many of them were burned out, anxious and depressed. We need a well-being revolution

By Samantha Dewalt, Willy Das and Daniela Gimenez-Jimenez
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

By
September 8, 2025
Meet the millennial couple who risked their savings and got a $1 million loan to buy the world’s oldest operating drive-in theater
Success

Meet the millennial couple who risked their savings and got a $1 million loan to buy the world’s oldest operating drive-in theater

By Gene Puskar, Mingson Lau, Holly Ramer and The Associated Press
September 6, 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

By
September 5, 2025
Andrew Filev
Commentary

My $2.25 billion exit taught me that Silicon Valley’s obsession with 100-hour weeks is actually sabotage. It’s a marathon, not a sprint

By
August 30, 2025

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