We’re looking forward to introducing you to oliver wilcox. Check out our conversation below.
oliver, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What is a normal day like for you right now?
Right now, ‘normal’ is anything but. Since we last spoke, I’ve made some dramatic changes. Pre-COVID, my brand, Maybe Today, was my full-time hustle—designing, printing, shooting photos, shipping orders. But when the pandemic wrecked the supply chain and my biggest distributor in Hong Kong went under, I had to pivot. I took a design job at a cannabis brand in LA, funding the business on the side, but couldn’t afford the same production scale. After getting laid off, I went to a location that, I cannot disclose, for a labor job on a military base—grueling hours, but zero living costs. It’s letting me rebuild the brand better than ever, with a full new line dropping this fall.
So, a normal day? Wake up at 6 AM, shower, grab coffee, 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. It’s relentless, but every day gets me closer to relaunching. I’ve attached some of the new pieces—this is the comeback phase.
Can you briefly introduce yourself and share what makes you or your brand unique?
Sure! I’m Oliver Wilcox, the founder and designer behind Maybe Today—a brand built on raw creativity, resilience, and the kind of hustle that doesn’t quit. At its core, Maybe Today is about more than just clothing; it’s a mindset. Every design, every piece, comes from a place of turning obstacles into fuel.
I have been designing and making clothes since I was 14. I have worked for several other brands before starting my own in 2016.
Before COVID, I was all-in: designing, printing, shipping—everything hands-on. But when the pandemic hit, supply chains collapsed, my biggest distributor folded, and I had to pivot hard. I took design gigs to keep the dream alive, even working as a laborer in this 3rd world country to fund the comeback. Now? I’m channeling every ounce of that grind into a new line—better designs, sharper execution, and a story that proves you can rebuild from scratch.
What makes Maybe Today special? It’s not just apparel; it’s a testament to adapting, pushing through, and creating something meaningful when the odds are stacked against you. Right now, I’m laser-focused on the fall launch—this isn’t just a drop, it’s a reset. And yeah, I’m doing it all while working 12-hour days on a military base. If that doesn’t sum up the brand’s ‘make it happen’ ethos, I don’t know what does.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who taught you the most about work?
My parents, without a doubt. They were both self-made and showed me what real work ethic looks like. My mom ran a business that put together welcome packages for newcomers—she’d spend hours packing bags with coupons and brochures from local advertisers. She was always hustling, always ‘on,’ and that mentality stuck with me.
My dad was a contractor, and he taught me two things that shaped how I approach everything: First, the value of creating with your hands—there’s nothing more satisfying than building something tangible. And second, the importance of doing things right. He drilled into me, ‘If you’re going to do something, do it properly.’ That meant precision in your work, keeping your space clean, and never cutting corners.
Between her relentless hustle and his craftsmanship, they gave me the blueprint for how I run my brand today—hands-on, detail-oriented, and all-in.
Was there ever a time you almost gave up?
Yes, absolutely. There was a point where sales had slowed way down, and I felt completely disconnected—like I’d lost touch with what my audience wanted. I was pouring every extra dollar into the brand, but the results just weren’t there. It got to the point where I convinced myself it was over. I stopped designing, stopped running ads, and for months, I was barely scraping by with just a handful of sales a day.
Then, almost out of nowhere, I had this breakthrough—a way to significantly improve the product’s quality without adding extra work or overhead. The margins took a small hit, but the trade-off was worth it. That one idea reignited my creativity, and things started turning around. Looking back, I realize sometimes you have to step away to reset. That low point ended up being the push I needed to come back stronger.
So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
I don’t know. I read a quote recently that said something like, ‘Everyone you meet has their own version of you in their head.’ And I think that’s true—the only person who really knows the ‘real you’ is you. Everyone else just has their own perception.
That said, I don’t put on an act. I’m not an actor. I don’t dress or behave differently depending on the environment—I’m only capable of being the ‘real me.’ Whether that aligns with how people see me? That’s up to them. But I’m not out here playing roles. What you see is what you get.
Okay, so before we go, let’s tackle one more area. If you knew you had 10 years left, what would you stop doing immediately?
Honestly? I don’t think I’d stop doing anything—I’d just shift priorities. I’d get the hell out off of this military base, for starters. Spend way more time with family. Surf more. But I don’t think I could ever fully ‘stop’ working—my brain doesn’t have an off switch like that.
The grind is part of who I am. Even with a deadline hanging over me, I’d still be creating, building, pushing forward. Maybe I’d work smarter, but I’d never stop entirely. Life’s too short for half-efforts, but it’s also too short to sit still.
Contact Info:
- Website: https://www.maybetodaynyc.com
- Instagram: https://instagram.com/maybetodaynyc
- Linkedin: https://www.linkedin.com/oliver-wilcox-design
