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
We finally got pictures.
We first kicked things off with TEG (The Evans Group) on August 27th, 2024—or at least that’s when I logged the payment in our very official Google Sheets tracker. TEG is a U.S.-based product development company that helps emerging brands bring their designs to life, especially if you’re starting from scratch with no experience. That was us.
Now, almost a year later, we finally have something to show for it: photos of our sample sweatshirt and pants.
Yes, the back looks like a diaper. No, it won’t stay that way. First sample’s got problems.
After months of shipping fabrics back and forth, endless tweaks, and more calls with my brother Johnny than I can count, we finally have something that looks and feels real. It’s just photos for now—but after the pace we’ve been moving, it feels like a huge step. Like they’re finally real.
Next week, I’m flying out to LA for the fitting. We get one round of edits on the first samples before they make the final version, so I’ll be there in person to make adjustments to the fit and feel—make sure everything’s just right before we go into production.
Honestly came out great
Should it have taken this long? Definitely not. But does that take away from how excited I am? Also no. What does take away from the excitement is this: I recently met with a potential manufacturing partner in Peru about a t-shirt we’re developing, and they told me they’d create the tech packs, pattern and size-grade the garment —for free. So yeah, realizing we paid TEG $7,556 for basically the same thing? That one stings.
But we move on, its just money right? … right?
The Hat Situation
Yeah… that’s the puckering problem
Let’s talk about the hats. Communicating with our manufacturer has been... challenging. We’re basically collaborating via vibes at this point— and the vibes need a translator.
My brother’s been handling most of the back-and-forth, trying to fix a puckering issue on the front of the hat. He’s sent notes, diagrams, marked-up photos—he even circled the problem area with a big red circle like he was grading a failing paper. The language barrier has made everything harder than it should be, but after much back and forth, we think we’ve finally fixed the issue. So, at least there’s that.
The frustrating part is that the quality hasn’t been bad—it’s actually pretty good. If we can just iron out the communication (pun intended), we might be in business.
The TikTok Grind
I’ve been trying to keep the TikTok momentum going... and wow, I completely underestimated how hard this would be.
It’s one thing to have ideas. It’s another to turn those ideas into actual videos that don’t make you want to bury your phone in the backyard out of secondhand embarrassment. I’m slowly figuring it out, though. Each video feels slightly less awkward than the last, and I’ve learned a ton just by forcing myself to hit “post” and move on.
After way too much debating over half-inch rectangles… we’ve chosen our label.
The worst part is sinking 3–4 hours of your free time into making and editing a video—only for it to get 120 views and 1 like (from my girlfriend). Those are the ones that really make you want to just stop. But I’ve been trying to stay focused on keeping the momentum going and not getting too caught up in the numbers.
The goal isn’t to go viral overnight… or maybe ever—it’s to build a record of our progress. Hopefully, someone finds their way to our page one day and sees not only the quality improve, but also that things weren’t perfect when we started. Because they’re definitely not. And I don’t think they’ll ever be.
After way too many iterations... here’s the one that stuck. Our final label design.
Wrapping Up
All in all, things are slowly but surely moving forward. Some lessons have been expensive, others just frustrating, but every step feels like it’s adding to the foundation of what we’re trying to build. We’re not moving fast, and we’re definitely not moving perfectly—but we are moving.
Appreciate you following along and being part of this. Whether you’re here out of curiosity, support, or just waiting to see if this whole thing flames out spectacularly, I’m glad you’re here. Until next time—onward.
- Nick
P.S. If you think someone else might like this, send it their way.
▶ Song on repeat: Going Under by Borgeous, Loud Luxury
▶ Current read: Project Hail Mary by Andy Weir
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