Before becoming the creator known as Dessy, founder of Dessy’s Tiny Kitchen and TikTok star @285TonsOfFun, she was scaling rooftops across Florida—not as a creator, but as a hustler in the truest sense: door-knocking for roofing companies, trying to close deals just to survive.
“I started out selling roofs, but something wasn’t adding up,” she says. “I asked the wrong questions… and got fired. That’s when I found out the company was committing fraud.”
With no income, Dessy did the only thing she could—bet on herself. She enrolled in an insurance adjuster training course, knowing that adjusters didn’t have to chase down business like she had. “They just showed up and got paid,” she recalls. “I thought, maybe I could be that person.”
And then—divine timing.
She got a text from Alacrity: emergency deployment in New York, $54/hour, overtime after 40 hours, up to 84 hours per week. That job netted her nearly $24,000 in a single month, even without a license—because emergency licenses were being issued on the spot.
She brought her brother with her. He made even more than she did.
Most people would stop there. But Dessy isn’t most people. The moment she returned from that first emergency deployment, she immediately completed her insurance adjusting course and officially got licensed—laying the groundwork for a more stable and scalable future in the field.
🎥 Going Viral by Being Real
When another opportunity came up in South Carolina, she had her license but none of the special certifications required—yet the recruiter assumed she had them. She took the leap.
“I had nothing but $119. I borrowed my grandpa’s van, turned it into a mobile home, and hit the road,” she says.
This time, she filmed the journey.
Her video—“I’m leaving for a job in another state with no money”—went viral. She didn’t have followers, just raw honesty. But the response was immediate. Viewers began supporting her in real time: sending gifts, money, offering encouragement, buying her gear like Cougar Paws, rope & harness kits, even food.
At night, she would sleep in the van with her live still running. Her audience—millions over time—would watch over her like family. “They’d tell me to lock the doors. They kept me safe. They made sure I kept going.”
⛰️ Climbing Roofs, Building a Brand
Dessy became known across TikTok as The Clever Adjuster — a woman climbing steep roofs in hard hats, showing what most only talk about. And she wasn’t afraid to post her earnings. $20K. $24K. Month after month.
“People saw what was possible. I made them believe again.”
She built a loyal following: The Spicy Gang, who showed up on every live with fire and pepper emojis. Her catchphrase? “Stop Play’n Wid Me”—a phrase she turned into a viral rallying cry and merch line.
Every post had purpose. “Stop Play’n Wid Me and get your adjuster license.” “Stop Play’b Wid Me and go make $20K this month.” Her lives were high-energy, empowering, and real. No filters. Just facts and faith.
During this time, still on her Clever Adjuster account, Dessy began sharing another side of her hustle: cooking meals out of her van and laundromats. She used hot plates, car battery stoves, and gas burners to make full-course meals from parking lots across the country. These behind-the-scenes videos struck a chord—showing not just how she worked, but how she survived.
She became the most influential adjuster on the internet at that time, known by name everywhere she went. Her growth was entirely organic—built without paid ads—and driven purely by impact, relatability, and results.
In a very short time she grew a private Facebook group of over 3,000 members, a Discord community of 6,000+, and built massive anticipation for her upcoming Clever Adjuster mentorship program, which she hadn’t yet released but showed immense potential.
“I was proud to walk away from that roofing company doing fraud. I knew helping people through insurance adjusting was the right way to serve my community.”
💡 A Vision Bigger Than The Job
After traveling across multiple states—Minnesota, Texas, North Carolina—teaching others how to get into the industry, Dessy saw the bigger picture.
At a rope & harness certification course in Georgia, she noticed something: the instructor made $12,000 in a single day from just 20 students. That sparked an idea. Why not create an online course to train others nationwide?
She began planning digital products, affiliate partnerships, webinars, and a full coaching brand under The Clever Adjuster, aiming to teach thousands how to enter the industry.
“If I helped even 100 people make $20K a month like I did… that’s generational impact.”
Although adjusting paid her $20K to $24K per month, her combined income—with social media earnings, affiliate deals, and commissions from training schools—was well above that. Her influence helped others believe they could achieve the same, and many of her viewers went on to purchase adjuster licensing courses because of her.
Before her injury, she had recently partnered with a second training school, creating promotional content and planning a deeper affiliate relationship—one that never fully launched due to her medical pause.
⛔️ A Hard Stop… and a New Beginning
But just as she was hitting her stride and laying the foundation for something truly impactful, injury forced Dessy off the roofs. The physical toll of the job interrupted her journey, but she never stopped adjusting to life or moving toward her purpose.
Dessy had quietly launched a second TikTok account: @285TonsOfFun, even before her injury, with the intention of building a monetized platform focused on product promotion and affiliate content—an additional stream of income to complement her already-growing success as The Clever Adjuster. She hadn’t told her Clever Adjuster audience about it, and vice versa—maintaining both identities separately like a double social media life. She expected it would take time to grow, but her very first video exploded — over 5 million views — and she gained 84,000 followers in less than a week.
Dessy had already begun creating videos about her weight loss journey and recommending products that were working for her, well before the viral explosion of Dessy’s Tiny Kitchen. She promoted these products on TikTok Live, offering honest insight and real-time results—building trust with a growing community. That product-focused content never stopped. After her weight loss journey came the pimple-popping squishy ASMR niche, which drew massive engagement. Eventually, she expanded again into her now-iconic tiny Caribbean food videos under the Dessy’s Tiny Kitchen banner. Today, she continues to promote products alongside a wide range of creative content—refusing to be boxed into one niche. Her community followed—and grew.
📈 From Survival to Strategy
Dessy didn’t just go viral—she built a following around relatability, resilience, and real strategy. She monetized through TikTok Live, affiliate deals, merch, and audience-driven product launches. Today, she’s pivoting once again—into AI automation, digital marketing, and brand consulting.
She continues creating content while recovering, with the intention of one day returning to the field stronger than ever.
“If I can go from $119 in a van to $24K+/month, anyone can. I just showed people what that looks like in real time.”
From The Clever Adjuster to Dessy’s Tiny Kitchen, from viral ASMR to entrepreneurship, Dessy has become a recognizable figure on TikTok—not just for what she does, but for who she is.
You can find Dessy’s content not only on TikTok under @285TonsOfFun, but also across Instagram, and YouTube. Her reach continues to expand, fueled entirely by community, creativity, and consistency—not ads.*
