For many entrepreneurs, success is years in the making. Hudson Leogrande knows this better than most. Over 14 years, he transformed himself from a homeless teenager into the leader of a loungewear brand on track to generate $1 billion in annual revenue, while also serving on the board of David Beckham's wellness company, IM8. Along the way, he learned to convert setbacks into opportunities, launching ventures wherever he spotted an opening.

At 16, Leogrande's circumstances were dire. He had dropped out of school, lacked direction, and was experiencing homelessness, sleeping on the floor of a friend's studio apartment. Yet through the instability, one conviction remained firm: he wanted to build something of his own.

"I felt like I didn't belong, like I didn't fit in," Leogrande told 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 that entrepreneurship lay ahead. He spent several months working a chimney-cleaning telemarketing job while completing high school in the evenings. Ultimately, though, he wanted a role where his income was directly tied to his effort. At 19, he moved into car sales, which gave him his first real taste of running a business — landing his own deals with "no one holding your hand." His performance was strong enough to earn a promotion to manager within his first year.

During his final year as a teenager, Leogrande also launched his first business: an at-home teeth whitening brand called PurelyWhite Deluxe. It would be years before the company turned a profit, so he kept it on the back burner as other opportunities arose.

One proved irresistible. At 22, Leogrande moved to California, where he and several friends launched an "Airbnb arbitrage business," signing long-term leases on Los Angeles properties and subletting them to short-term rental guests. He spent months managing the rentals, sometimes driving out at 10:00 p.m. to resolve last-minute guest issues. At its peak, the operation was pulling in $60,000 a month. Meanwhile, he continued trying — unsuccessfully — to get his teeth whitening brand off the ground.

With the Airbnb venture thriving, Leogrande felt he had finally reached the success he had been working toward for five years. He had gone from homelessness to living in Los Angeles running a six-figure operation. But his founder ambitions pulled him back to New York, where he dreamed bigger. PurelyWhite still had not earned a single dollar, so he returned to car sales to supplement his income.

"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 said. "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 devastated many small businesses, Leogrande says he found his formula during lockdown. An influencer he had met in Los Angeles, known as Aiden, posted a Snapchat video promoting PurelyWhite. Within a day, roughly $4,000 in sales flooded his Shopify account. Leogrande was so stunned he assumed the platform had glitched. Following that initial post, PurelyWhite began receiving hundreds of orders daily. The breakthrough mirrored a broader pandemic-era shift: as consumers spent more time on social platforms, direct-to-consumer brands that leveraged influencer-driven content saw outsized growth compared with traditional retail channels.

He continued riding the Snapchat advertising wave, but when the platform altered its algorithm and PurelyWhite's content views plummeted, the business collapsed. The collapse underscored a well-documented vulnerability for digitally native brands heavily reliant on a single platform's algorithm. At 26, Leogrande was again struggling to keep the company afloat. Still, he sensed something bigger awaited. Two years later, he launched Comfrt.

Launching Comfrt and Approaching $1 Billion in Sales

Long before he had a product, Leogrande had a name. He purchased the trademark for Comfrt with a vision of building a brand centered on comfort — not just physical, but mental. After years of instability and hardship, comfort had taken on a significance far beyond coziness.

Bootstrapping the company with $50,000, Leogrande experimented with products that could convey that feeling. He settled on slightly weighted hoodies and sweatpants, believing they could foster a greater sense of calm and security. That concept became the foundation of Comfrt — a loungewear brand that would later go viral across social media and expand into blankets, backpacks, and pet apparel. The weighted-apparel concept tapped into a growing consumer interest in wellness-oriented and sensory products that gained traction during and after the pandemic.

The company's ascent was not immediate. In its early days, Comfrt had little corporate structure: no executive team managing daily operations, and Leogrande himself did not yet know what a CFO was. As the brand grew rapidly, he poured his savings and earnings from other ventures into inventory. In 2024, the company went broke multiple times.

"I sacrificed relationships, my life, to build," Leogrande recalled. "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."

Comfrt soon staged a swift turnaround, becoming what Leogrande describes as a "true player in the apparel space" by strengthening its operations. He brought on a COO and CFO to help manage the business. And just as PurelyWhite had done, Comfrt began to thrive through the power of social media.

Today, Comfrt maintains a core network of 500 content creators who produce brand videos, and its once-bare-bones operation has grown to 140 full-time employees. The creator network reflects a wider industry move among DTC apparel brands toward building in-house influencer ecosystems rather than relying solely on paid advertising. The company says it is on track to reach $1 billion in revenue by the end of this year, and Leogrande is now running the kind of company he always envisioned.

This story was originally featured on Fortune.com.