He was homeless at 16. Now, he sits on the board of David Beckham’s wellness company and his business is about to hit $1 billion in revenue

Many entrepreneurs chase success for years before finding their breakthrough. And Hudson Leogrande knows the trials that come with building from nothing all too well: over the span of 14 years, he went from being homeless as a teenager to leading a $1 billion loungewear brand and serving on the board of David Beckham’s wellness company IM8. Along the way, he learned to turn setbacks into opportunities, building businesses wherever he saw an opening.

At just 16 years old, Leogrande was down on his luck. He had dropped out of school, unsure of where to place his talents, and was experiencing a bout of homelessness, crashing at his friend’s studio apartment. While his life was unsteady, one thing about Hudson held rock-steady: he wanted to be his own boss and build something of his own.

“I felt like I didn’t belong, like I didn’t fit in,” Leogrande tells Fortune. “At 16, I realized what it was. I wasn’t really interested in existing. I didn’t want to go out to the parties and the weekends. I really wanted to learn this other world…I wanted to be financially literate. I wanted to understand it.”

From high school dropout to serial entrepreneur

Even as a teenager, Leogrande sensed his entrepreneurial future was just around the bend.

He spent several months in a chimney-cleaning telemarketing role while wrapping up high school after the sun went down. But ultimately, Leogrande wanted a job where his earnings were tied directly to his hard work. At the age of 19 he went into car sales, where he got his first taste of entrepreneurship; Leogrande said he was basically running a business, landing his own sales with “no one holding your hand.” He was so good at the job that he was promoted to a managerial........

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