Kevin O’Leary, famously known as “Mr. Wonderful” on Shark Tank, is widely recognized for his blunt and often aggressive approach. He is unapologetically direct, a trait that some appreciate for its honesty while others find abrasive.

Despite his tough exterior, O’Leary recently shared a vulnerable moment from his past that shaped his views on work, leadership, and entrepreneurship.

The Humiliation That Changed Everything

O’Leary opened up on Facebook about one of his most humiliating experiences—getting fired from his first job at an ice cream shop. As a high school student, he was eager to impress a girl who worked at a nearby shoe store.

However, his plan was ruined when his boss asked him to scrape gum off the floor. Knowing the girl was watching, he refused, arguing, “You hired a scooper, not a scraper.” His boss responded, “You’re gonna do whatever I say. I own the store.