06/25/2025
7 Unhinged Founder Stories
Success stories often get polished over time.
But the truth?
Some of the world’s most successful founders did unhinged, scrappy, and downright hilarious things to survive.
Here’s 7 wild things entrepreneurs actually did to start or grow a business:
FedEx’s Founder Gambled the Last $5K in Vegas
When FedEx was on the verge of collapse, Fred Smith took the company’s last $5,000 to a Las Vegas blackjack table. He won enough to keep the business alive *for one more week*—just enough time to secure funding.
Lesson: Sometimes you just have to bet it all (maybe not like Fred though 🤣).
Steve Jobs Cold-Called HP at Age 12
Jobs cold-called Bill Hewlett (the co-founder of HP) asking for spare parts for a school project. Not only did he get the parts—he got a summer job.
Lesson: There’s power in just asking.
Nasty Gal’s Sophia Amoruso Dumpster-Dived Her Way to Millions
Sophia started by dumpster diving for vintage clothes and flipping them on eBay. That side hustle became a multi-million dollar fashion empire.
Lesson: Real resourcefulness beats perfection.
Elon Musk Slept on the Factory Floor
In Tesla’s toughest years, Elon literally slept on the factory floor and showered at the YMCA. He wouldn’t leave until the production line was back on track.
Lesson: The journey won’t always be pretty and will require relentless grit.
Under Armour Was Sold Out of a Car Trunk
Kevin Plank drove up and down the East Coast selling shirts from his car trunk before Under Armour became a billion-dollar brand.
Lesson: Sometimes distribution is you.
Airbnb’s Cereal Hustle
When Airbnb was struggling to survive, the founders literally sold cereal to keep the company alive.
They created limited-edition boxes called Obama O’s and Cap’n McCain’s during the 2008 election and sold them for $40 each.
The cereal sales kept Airbnb afloat long enough to get into Y Combinator.
Lesson: Sometimes saving your startup means becoming a cereal entrepreneur.
Sara Blakely Sold Fax Machines While Building Spanx
Sara sold fax machines door-to-door by day, hustled Spanx by night, and snuck her prototypes into Neiman Marcus bathrooms to convince store buyers.
Lesson: Do whatever it takes (but do it legally 👀).
These are real Do’ers. These are the kind of people doola helps to start a business and grow an empire.
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