Oak Drive Monthly Update - March

You’re reading Oak Drive’s Monthly Update — a newsletter about me and my brother building a clothing brand from scratch. Each issue shares honest updates, real thoughts, and the actual numbers behind creating something high-quality and sustainable.

No playbook. No overnight success. Just two brothers trying to do it right — one misstep at a time.

Let’s get into it.

— Nick

TikTok: @oakdrivebrand
Instagram: @oakdrivebrand

If you’ve bought, followed, liked, shared, or sent us a supportive message, we appreciate you.

If you haven’t followed us yet, this is me formally asking you to please do that. I’ve lost all shame at this point.

I’ve started a 90-day TikTok challenge, which means I’m posting every single day.

To be honest, this whole thing is a bit brutal.

Some days it feels like I’m actually getting comfortable on camera and figuring out how to speak without sounding weird. Other days it feels like I’m getting publicly humbled by a mobile app.

Trying to figure out what actually drives engagement has been way harder than I expected. I definitely have not found the recipe yet. But on the bright side, I still have 75 more days to figure it out, so there’s still hope. Barely.

Please follow along if you haven’t already. We need more followers. Badly. At this point I’ve lost all shame, so yes, I am begging lol.

And for anyone keeping track at home, the 2026 TikTok scoreboard currently stands at:

Nick: 16
Johnny: 2

Like most things in life, I’m just the harder-working and more driven brother. Still waiting for Johnny to start pulling his weight on the content side, but I’m not exactly holding my breath.

The good news: hats are in pre-production and shirts are officially in production.

The bad news: there’s not a ton of exciting detail to report just yet because a lot of it is still in that glamorous phase known as “waiting.”

That said, I’m really excited to get the hat samples in hand. Once we actually have them here, it’ll all start to feel a lot more real. We’ll be able to wear them, shoot with them, make content with them, and start putting together actual product photography instead of just staring at mockups and AI generated images.

That’s when things start getting fun.

We also ordered our hang tags and seaweed polymailers.

One thing I’m learning is that there are always a million little things to design. Which is fun, but also means a lot more work and thought goes into this stuff than I originally expected.

I’m trying to make Oak Drive feel more cohesive overall, which means thinking more intentionally about the smaller details too — using similar text, branding language, colors, and generally making everything feel like it belongs to the same brand instead of a bunch of random pieces slapped together.

It’s a small update, but it feels like an important one.

Lately we’ve started thinking about what we want to make for fall.

I’m a guy in my late twenties staring 30 straight down the barrel, and with that has apparently come a disturbing new development: I’m becoming more and more of a sweater guy. Somewhere along the way, hoodies started losing ground, and the idea of an elite sweater started sounding more and more appealing. My girlfriend CC would also like credit for this transformation, which, annoyingly, is probably fair. Makes the whole thing worse, honestly. Feels like I’m going soft, but damn, they’re comfortable.

“Man, you’re down bad. CC’s got you puffed up and proper looking like a good boy” (Johnny’s very constructive feedback on the newsletter)

Because of that, I’ve been talking with a bunch of knitwear manufacturers in Peru about developing some kind of waffle knit sweater / sweatshirt.

I polled a bunch of friends to figure out which direction people liked more, and the general consensus was that the sweatshirt was the slight favorite, with the crewneck close behind.

Right now though, I think we’re probably leaning crewneck.

The sweatshirt sounds cool in theory, but I think people like the idea of it more than they’d actually wear it. The crewneck just feels more versatile, easier to throw on, easier to style, and more likely to become something you actually reach for all the time.

The sweatshirt, on the other hand, feels a little more niche. It kind of lives in this oddly specific zone where you want to be comfortable, but also look cool, but also look like you’re not trying to look cool. Which starts to feel a little performative. Very male. Very “I just threw this on” when in reality that was absolutely the goal.

That said, we’re probably going to sample both before making a final decision.

And in an effort to learn from previous mistakes, we’re talking with 4 different manufacturers this time to see who’s actually best instead of rushing into something and regretting it later.

The hope is that by getting multiple samples from different manufacturers, we can find one we can work with for years to come — instead of repeating what we’ve done with hats, which has basically been trying one new manufacturer at a time until suddenly you look up and realize you’re already on manufacturer number three.

We’re still figuring a lot of this out as we go, but things are moving.

Shirts are in production. Hats are getting close. Fall ideas are starting to take shape. And I am apparently now a full-time TikTok employee.

Appreciate everyone following along.

Nick