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 launched hats and crossed $1,000 in sales — THANK YOU 🙏

📦 😭 Packaging pain: current mailers are tough to open; we’re exploring easier-to-open options

🧢 New hats: Dad hat + Camo samples look good (patch needs some reworking)

👕 Tees: first sample is a big win; MOQ is 200, and we’re considering 400 to launch multiple colors

We’re live. As most of you know, we kicked things off with two 5-panel rope hats—and you all showed up.

Thank you for the support: we just crossed $1,000 in sales! We’re inching toward break-even on our first product, which feels amazing.

If you haven’t grabbed one yet, consider this your nudge: oakdrivebrand.com. Get the day-one piece while it’s around—future you might kick yourself for missing the very first Oak Drive merch. This could be a life-changing opportunity 😉.

Also, a quick shout to Johnny—he’s personally packing every order in our glamorous world HQ (his living room). Do him a favor and make him do more manual labor. He needs it.

Packaging: We heard you—and felt it ourselves. The current mailers are way too hard to open. I did a test order to myself and even knowing the trick, I still fought the thing like it owed me money. We’re exploring options to upgrade our packaging to be more user-friendly so unboxing feels intentional, not like a puzzle.

Assortment: One hat style doesn’t fit everybody (literally and vibe-wise). Some folks don’t wear hats, some don’t love this silhouette, and plenty of parents prefer a classic baseball cap. Translation: we’re leaving demand on the table and the store looks a bit sparse. That’s the challenge of running a fledgling brand. Money is hard to come by and inventory is expensive.

What we’re doing about it: expanding the lineup and accelerating development. I’m hyped on the shirts—the quality is there—but wow, this process takes time.

As we teased last month, we’ve been developing new hat styles—and the first samples just landed. They’re pretty good. A few details need tightening up (especially the patch), but we’re close.

What’s moving forward:

Development takes longer than you expect and ties up cash. Every new product requires upfront spend—samples, revisions, and MOQs—well before any cash comes back. On the flip side, the bigger risk is the store feeling empty and not having products to sell. As good as our hats are, one hat does not make a clothing brand.

So we’re taking the leap: expanding the lineup conservatively (not made of money) but ambitiously. They say you’ve gotta spend money to make money, right? It’s a constant battle between being too cautious and being overly ambitious.

I have to say it: this is one of the most comfortable shirts I’ve tried on—heavyweight cotton that’s soft as butter. The fit is extremely good. We’ve got a few tweaks left (shorten the overall length, add accent details, and finalize a clean woven label), then it’s go time.
For the fabric nerds the shirt is made from 320 gsm Tanguis, ring-spun, combed, organic cotton. I didn’t know what that meant three months ago either. Translation: the Rolls-Royce of cotton.

Timeline: We aimed for Christmas, but we need one more sample to lock in the details—so holidays is a no-go. We’ll have to build a real holiday plan next time—it’s a big miss—but I’d rather ship the shirt right than rush it. With how this sample turned out, we’ll be selling it for years.

How we’ll order: The factory minimum is 200 units, but the quality has me thinking bigger—we’re considering 400 so we can offer multiple colors from day one instead of a single run. It’s not cheap but as I said: spend money -> make money.

How you can help (takes 30 seconds):

Thank you for showing up this early. Every order, reply, and tag genuinely moves Oak Drive forward.

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