Steve Harvey had $35 and was sleeping in his car in hotel parking lots.
Within days, he had almost $1,000 and his first TV appearance.
He was ready to quit. He went to a pay phone to call his dad.
First he checked his answering machine. Showtime at the Apollo wanted him on TV that Sunday.
In the video below, he explains why that felt like bad news: "I've got $35. How am I gonna get to New York?"
Then a second message. A gig in Jacksonville, Friday night, $150. He drove three and a half hours.
He killed. The guy who hired him offered another $150 for Saturday. Now he had $300.
He found a $99 round trip to New York, parked his car at the airport and flew with everything he owned in two bags.
At the Apollo that night, he got a standing ovation. They paid him $750.
"I'd never made $750 telling jokes in one night."
Weeks later they asked him to host the show. He says he did it for eight years.
The $750 night only happened because he didn't skip the $150 one.
My takeaway: small money isn't small when it's the bridge to bigger money. I've turned down $100 jobs I should have taken.
Would you have driven 3.5 hours for $150 with $35 to your name?
Sara Blakely started Spanx with $5,000 in savings at 29.
At 41, Forbes put her on the billionaires list. She still owned 100% of the company.
She was supposed to be a lawyer. She took the LSAT and, in her words, "basically failed it." She took a prep course and tried again. That didn't work either.
So she sold fax machines door to door instead.
The idea came from a simple problem. She wanted no panty lines under white pants.
Then Oprah called. Later she went on QVC with her second product and sold over 8,000 in 6 minutes. That's when she knew she wasn't "a one-hit wonder."
Most founders give away pieces of their company just to survive. She kept every share.
In the video below, she explains how she sees money: "Money just makes you more of who you already were."
That line aged well.
In 2021 she sold a majority stake to Blackstone in a deal that valued Spanx at $1.2 billion.
Then she gave every employee $10,000 and two first-class plane tickets.
My takeaway: every share you keep is a decision you get to make later. I've given up a bigger cut than I should have on a side project, and I still think about it.
Would you rather own 100% of something small or 10% of something huge?


