From Multi-Million Dollar Brand to Military Base Laborer: The Oliver Wilcox Story

The story of Maybe Today NYC isn’t one of sudden viral fame or venture capital. It’s a story about the ultimate hustle, a gut-wrenching setback, and the founder who is literally working a grueling labor job on a military base to fund the brand’s comeback.

This is the true, uncut hustle of Oliver Wilcox, and why the clothes you wear today are a receipt for his unyielding belief in the brand.

The Beginning: Built From Stencils and Sweat

Oliver Wilcox didn’t go to a fancy design school. He learned the craft because he couldn't find—or afford—the clothes he actually wanted to wear.

Growing up in a North Carolina surf town, the initial spark came from a place of necessity. He was an art kid who started by making stencils and spray-painting his own designs onto blank garments. It was messy. It was low-fi. But it was authentic. That hands-on spirit pushed him to dive deep, teaching himself screen-printing and obsessing over Photoshop and Illustrator to bring his ideas to life.

"I made stencils of anything I could think of and spray-painted them onto blank garments. The quality was trash and I knew there had to be a better way."

This dedication eventually led to his first clothing venture. After securing a small investment, Oliver knew one thing: if he was going to take a shot at fashion, he had to go to the heart of it. He packed up and moved to New York. The hustle paid off.

Maybe Today NYC quickly found its footing. Focusing on a raw, street aesthetic and using Instagram as its primary vessel, the brand skyrocketed into a multi-million-dollar operation, complete with distribution deals in Asia and pop-ups in Tokyo. The dream was fully realized.

The Hard Reset: The Day Everything Changed

Then came 2020. The kind of global event that exposed the fragility of every supply chain and every big plan.

For Maybe Today NYC, the impact was devastating. The supply chain collapsed, and the brand’s largest distributor in Hong Kong folded. Suddenly, the entire momentum stopped. Oliver was faced with a choice: let the brand die, or do something drastic to save it.

He chose the latter.

To keep Maybe Today NYC alive, Oliver had to step away from his design desk and take a job that would cover his living costs entirely, allowing him to pour every spare penny back into production, sourcing, and design for the comeback.

The only job that fit the requirements was a grueling, low-glam labor position: working on a military base in an undisclosed location (a self-described "3rd world country").

The Ultimate Hustle: Fueling the Fire, Literally

This is where the true story of Grit and Resilience begins.

Today, Oliver’s 'office' isn't a design studio. It’s a base where he works 12-hour shifts, 7 days a week, fueling military vehicles. The work is tough, the hours are relentless, and the isolation is a constant test.

A normal day: "Wake up at 6 AM, fuel military vehicles by 8:15, then squeeze in emails, website checks, and order logistics. After that, it's a few hours of designing, more fueling, squeezing in whatever work I can, then sleep—repeat. Seven days a week."

He’s sacrificing comfort, time, and normalcy to be the sole investor in Maybe Today NYC's new line. Every single design, tech pack, fabric sample, and production run for this new drop is being funded by the sweat and long hours of his labor job.

Life’s a Gamble: The Clothes Are the Receipt

This journey is why our designs today feel different. They are heavier. They are darker. They are stamped with the undeniable truth of the brand’s current reality.

When you see the “Life’s a Gamble” hoodie, understand that it's not just a cool graphic. It's the philosophy keeping the brand alive right now. It's Oliver pushing his chips all-in on this vision.

Caption: The "Life's a Gamble" hoodie—the brand's philosophy and its current reality.

The new collection—featuring bold graphics like the Dragon and Yin-Yang designs—is a testament to that balance: the chaos of the situation, and the focus required to push through.

Join the Comeback Crew

This isn't just about selling clothes; it's about sharing a story that proves you can rebuild a dream from scratch, no matter the obstacle. It's about living the Maybe Today mindset.

When you shop the new drop, you aren't just getting an item of clothing. You are directly supporting a founder who is physically grinding it out, thousands of miles away, just to keep the brand's doors open.

Every single purchase funds the comeback.