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 position within the year he worked there.

During his last year of teenagehood, Leogrande also founded his first business: at-home teeth whitening brand PurelyWhite Deluxe. It would be years until the company got its sea legs and turned a profit, but Leogrande kept the business on the backburner as new gigs came into the fold.

One opportunity was just too good to pass up. At 22 Leogrande packed his bags and headed out to California where he and a few friends started an “Airbnb arbitrage business,” signing long-term leases on L.A. properties then subletting them to travelers on the short-term rental site. He spent months looking after the rentals, driving around at 10:00 p.m. to solve last-minute issues with guests. Leogrande says that at one point, they were reeling in $60,000 a month. On the side, he was still trying to get his teeth whitening brand off the ground, still to no avail.

With his Airbnb hustle doing so well, Leogrande says he felt like he had finally achieved the success he had been manifesting for five years. And in that time, he had gone from being homeless to living in L.A. with a six-figure operation. But Leogrande was dead-set on his founder ambitions, and headed back to New York ready to dream bigger. PurelyWhite still hadn’t made a single dollar, so he went back to car sales to pad his income, even though his sights were set on entrepreneurship.

“I got back into the car business again, and this time I am the worst employee there, because I was so out of it already,” Leogrande says. “I was like, ‘It has to be PurelyWhite…I didn’t know anything. But then during COVID I quit the car business. I say ‘Screw it. I’m all in.’”

While the pandemic hit many small businesses hard, Leogrande says he really cracked the code during lockdown. An influencer he had met in L.A. named Aiden posted a video on Snapchat promoting PurelyWhite, and within a day, around $4,000 in sales from netizens poured into his Shopify account. Leogrande was so shocked he believed the account glitched. After that first social media post, PurelyWhite began receiving hundreds of orders a day.

Leogrande continued to ride the wave of Snapchat advertising. But after the platform changed its algorithm and views of PurelyWhite content plummeted, his business crumbled. Leogrande was back to keeping the company above water. But the voice in his head told him there’s something bigger out there. At 26 years old, he launched his dream company, Comfrt.

Launching Comfrt and approaching $1 billion in sales

Long before he had a product for his viral clothing line, Leogrande had a name. He purchased the trademark for Comfrt, wanting to build a brand centered on helping people feel comfortable—not just physically, but mentally, too. And after years of instability and hardship, comfort had taken on a much deeper meaning than simply feeling cozy.

Bootstrapping the company with $50,000, Leogrande began experimenting with products that could deliver that feeling. He landed on the idea of slightly weighted hoodies and sweatpants, believing it could create a greater sense of calm and security. That concept became the foundation for Comfrt, the loungewear brand that would later explode across social media, and extend into products like blankets, backpacks, and pet apparel.

But the company’s meteoric rise didn’t happen overnight. In the beginning, Comfrt didn’t have much of a company structure; there was no executive team managing the daily ins-and-outs of a growing brand, and Leogrande didn’t even know what a CFO was at that time. Comfrt was growing fast, and Leogrande dipped into his savings and money from other ventures to get more product. In 2024, the company even went broke several times.

“I sacrificed relationships, my life, to build,” Leogrande recalls. “I would be up and it would be 2 in the morning and I would be approving videos that were supposed to be posted at 10 p.m…I was so addicted.”

But Comfrt made a swift turnaround and became a “true player in the apparel space” by beefing up its operations. Leogrande quickly brought on a COO and CFO to help run the business. And just like PurelyWhite, his hoodie brand began to thrive thanks to the power of social media.

Now, Comfrt has a core network of 500 content creators who make videos about the brand, and its bare-bones operation has grown to 140 full-time employees on payroll. The business says it’s on track to hit $1 billion in revenue by the end of this year, and Leogrande is now running the kind of company that he’s always envisioned.