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
TL;DR 🧾
We missed last month 😅 (holiday time warp) — we’re back ✅
We’re designing the next hat drop 🎩 and building a real drop schedule 📅 (no more winging it)
We’re on hat manufacturer #3 🤝 (yes, really) + can test with a 50 MOQ 📦
We’re fixing the packaging 📦 because the boxes are too hard to open 😤 (blame Johnny if you’ve suffered 👉😄)
Shirts are officially going into production 👕🔥: 400 total (200 MOQ per color 🎨 x 2 colors)
Johnny on christmas
We know… we missed last month. Consider this our official apology letter. Somehow the holidays always feel like you have time, and then boom — they’re over and it’s suddenly February. If you noticed, thank you for missing us — we’re choosing to take that as a compliment.
Alright, here’s what we’ve been up to:
Designing new hats 🎩
We’re trying to systemize our drops a bit more.
Up until now we’ve basically been winging it — designing things, sampling, tweaking, and then launching whenever the product is finally ready. Which is fun… but it also means we don’t really have deadlines, milestones, or any kind of repeatable rhythm.
So we’re changing that. We’re building an actual drop schedule with timelines for each step (design → sampling → production → photos → launch), and as part of that, we’re designing the next drop as we speak.
Also: we’ve started working with our third hat manufacturer. Yes. Third.
We’re pretty particular about the shape and fit, and it’s taken a couple tries to find one that really nails what we want. The upside with this new partner is they’ll let us do a 50 MOQ, which makes it way easier to test a drop without going all-in.
Upgrading our packaging 📦
We’re upgrading our packaging because… we heard you.
The boxes have been way too hard to open. Not to point any fingers, but as you know by now Johnny is the Oak Drive packing expert — so if you personally experienced this problem, you can go ahead and blame him. Not exactly the unboxing experience we were going for.
So we’re making a few changes:
Easier-to-open boxes (this is the main one)
More branding on the inside so it feels more “Oak Drive” the second you open it
Custom mailers for the shirts so tees show up looking intentional — because shirts are finally going to be in production, but more on that later
As soon as we have the updated packaging in hand, we’ll share it (and yes, we’ll test it by seeing if a normal human can open it in under 10 seconds).
Pulling the trigger on 400 shirts 👕
Alright… this is the big one: we’re officially pulling the trigger on 400 shirts.
A quick note on why that number: our manufacturer’s MOQ is 200 per color — so if we want to do two colors, that’s the deal. 200 + 200 = 400. Simple math, mildly terrifying commitment.
But like I told Johnny: you need stock to sell, and at some point you have to actually take the jump instead of debating it forever. Also — the shirts are dope, so I feel pretty confident we’ll move them. It might take time, but I’m not worried about them eventually selling.
Also, the production time is 95-100 days so need to move fast on these things so that they’re ready sooner rather than later.
We’ll share more as production gets moving (and as soon as we have a real timeline + progress to show). And yes, we’re also getting custom mailers for the shirts so they show up looking intentional — but more on that soon.
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That’s the update. Appreciate you being here and following along while we build.
Talk soon,
Nick
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