Rising Stars: Meet Oliver Wilcox of venice beach/austin

Today we’d like to introduce you to Oliver Wilcox.

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I started Maybe Today in 2016 in Brooklyn, New York. In the early days I did everything myself, including printing every order by hand, made to order. In 2021 I moved to Los Angeles and kept building the brand there.

In 2024 I took an odd job on a military base in Haiti. I only meant to do it for a short while, but the money was good, so I stayed two years. I couldn’t leave the base and worked 12 hours a day, 7 days a week, on a rotation of 90 days on and 3 weeks off. I used that money to fund Maybe Today. Since I couldn’t print orders myself from Haiti, I moved the brand to production and shipping partners, which forced it to grow beyond me working with my hands.

Haiti also gave me a lot of downtime. I started journaling heavily, and that turned into an app, currently in beta, that asks you questions and eventually writes your entire life story. I built a few other apps in that downtime too.

I got back in May 2026 and I’m now living in Austin, Texas, because the economy is so weird. I found a fun job here with a cool furniture company, and I’m doing that while building Maybe Today into something better than ever. I run the brand solo, handling the design, the photography, the Shopify build and the ads. I started with $5K and have a lot more now. It’s crazy what you can do with some money and stability.

My last official drop was this fall, and I’ve seen a great response. We just passed 22k orders since I started, and I think we can hit 25k by the end of the year.

I’ve learned so much from everything in life, and it’s crazy how life is like that. I’ve always been very fond of chess, and I’ve found that chess strategy shows up in day-to-day life.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
No, it hasn’t been smooth. I’ve failed several times. I’ve put real money into products and marketing ideas that did nothing, and some of that money came from 12-hour days I couldn’t get back.

It started with the way I ran the business. For the first stretch I did everything myself, printing every order by hand, made to order. That doesn’t scale, and it meant the brand was only as big as the hours I had.

The biggest challenge has always been money. I started with $5K, and the brand couldn’t pay for itself for a long time, so I had to find a way to fund it. That’s how I ended up on a military base in Haiti. I couldn’t leave, and I worked 12 hours a day, 7 days a week, 90 days on and 3 weeks off, running a brand from a distance the whole time. I couldn’t print orders from there, so I had to build real production and shipping partnerships. It was forced, but it made the brand better.

Running it solo is its own challenge. I handle the design, the photography, the Shopify build and the ads, so every mistake is mine. Every failed product or campaign cost me my own money, and I had to learn to figure out what actually went wrong instead of just trying the next idea.

Right now the challenge is time. I’m working a full-time job while building Maybe Today, so I have to be selective about where my hours go. The failures taught me to put money behind what’s already working instead of what I hope will work.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I run Maybe Today, a streetwear brand, and I do almost all of it myself: the design, the photography, the Shopify build, the paid ads and the content. My background is in marketing, so I treat the brand and the business as one job.

We’re known for heavyweight, quality pieces, and our Hell Was Boring hoodie is the one people come back for. I like clothes that look and feel better than they should for the price, and I like telling the story behind them instead of just posting a product.

What I’m most proud of is that I started with $5K, funded it with my own money, and have passed 22k orders. No investors, no team. A big part of that money came from two years on a military base in Haiti, working 12-hour days, 7 days a week. The brand grew while I was gone because I built real production and shipping partnerships to run it without me.

What sets me apart is that I can do every part of the job. Most people who start a brand are good at one thing and hire out the rest. I can design the product, shoot it, build the site and run the ads, so I move fast, I know where every dollar goes, and I’ve learned from my own failures instead of paying someone else to make them for me. In Haiti I also built a life story app, now in beta, and I’m putting what I’ve learned into a class for people starting their own brands.

Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
I wouldn’t call myself reckless, but I’ve taken some big risks.

The biggest was Haiti. In 2024 I took a job on a military base and ended up staying two years. I couldn’t leave the base and worked 12 hours a day, 7 days a week, 90 days on and 3 weeks off. I gave up two years of being around my own brand to earn the money to fund it. I didn’t know if Maybe Today would still be there when I got back. It was, and it was bigger.

The other risk is one I keep taking: putting my own money into the brand. I started with $5K and have never had investors, so every product and marketing idea I tried came out of my own pocket. Several of them did nothing, and that money was gone. I’ve failed more than once and kept going.

Here’s how I think about it. Every time we step outside, we’re taking a risk. I could die at any given second, so why would I be afraid to risk money? Money isn’t water, food or oxygen. You can make it back. If you’re going to bet on something, bet on yourself. I did that in Haiti, and I’d do it again.

I also like having stability behind me. A steady job I like here in Austin means one bad drop doesn’t end the brand, so I can keep swinging.

Contact Info:

• Website: https://www.maybetodaynyc.com
• Instagram: @maybetodaynyc