Oak Drive Monthly Update - February

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, or shared—we endlessly love you.

If you haven’t, respectfully, we need better.

We (Nick’s girlfriend) finally posted real content.

CC made an amazing video recap of their trip to St. Barths starring Augie, their adorable 2.5 year old nephew who is already carrying more marketing weight than both Nick and I combined.

On Instagram, I got super deep into creating a bunch of random hat designs that I thought were cool and started posting them on our Insta story as our “Design of the Day.”

We don’t intend to produce them immediately, but the initial volley of feedback on these designs has been astonishingly positive. Which is exciting. Who knew I had such a creative flare.

That’s sort of tongue in cheek because Nick and I invested in some help from AI. Oak Drive is now AI-powered.

Funny how when your brother writes the newsletter he conveniently forgets the video that you made… Current score Nick + CC: 2 Johnny: 0 - Nick

We were originally planning on an initial run of 400 shirts.

Not sure exactly how this happened, but I got a lovely text from Nick as I was sitting on the beach in Uruguay informing me that Peru had changed the math on us.

Either they were annoyed by Nick (if you know him, you know he’s annoying as sh%t most of his waking hours) or they were tired of us dragging out feet for such a small sale.

The MOQ conversation with Peru started at 200 units. Manageable.

Then, at the final moment, they upped the minimum to $12,000

As a savvy businessman, I saw the opportunity and tasked Nick with negotiating with Peru for a unit price break if we upped our quantity. He came away with nothing. Add ‘negotiating’ to the list of things I am better than Nick at.

All kidding aside, we are supremely convicted in our shirts, so it really wasn’t a deal breaker. Nick actually sold me on this line “If you want to double your money, do you think you have better odds selling these shirts, or throwing it into the stock market.” I picked Oak Drive.

We’re producing 600 shirts across three colorways:

Heavyweight cotton, durable and just an incredibly solid shirt that you love to wear.

Tentatively, we are planning for a June drop… the only problem is my wife Mal is due on May 6th. Nothing like packing some orders with a screaming baby (and an enraged post-partum wife to wrangle).

We are at the 1-yard line with our dad hat. Every day I keep oscillating between ready to pull the trigger and hesitant for launch. When I first pulled it out of the box I absolutely loved it.

It took us SO long to dial in the right beige, but we finally got there.

The catch is that it’s sort of see-through. You can see the sweatband through the exterior of the hat. In talking with the manufacturer, either we switch to a thicker material (definitely don’t want to do this), or we stick with it as it. Just one of the drawbacks of producing a light colored hat.

144 hats coming your way soon (should I be able to get over the hump and pull the trigger)

We are currently working on two designs for these. They are both awesome.

There’s always a fine balance between speed and precision. Nick and I haven’t quite figured out that balance yet, but the speed thing is sort of out of our control. I feel like every single time we are ready to get products into manufacturing it’s Chinese New Year.

Apparently all of China shuts down for what seems like a decade and NOTHING gets done.

Side note: To all of our buddies with big pumpkin heads, we’re thinking about you. We are looking into structured high-profile options for you. You know who you are.

I hate taxes. Every single cent I pay my accountant is worth it tenfold, but don’t tell him that.

Not only did I have to do everything to file our business taxes (thanks Nick for the help), but I got to be the first one to lay eyes on our profits on the year…or lack thereof…a big red number. Not good.

On the bright side, only up from here.

Thanks to the very few of you who made it through this extremely long-winded recount of our February. I think I write these things for myself more than anything; it gives me the opportunity to throw shade at Nick.

He did ask me to keep this short, I didn’t, but I still don’t believe he can read and even if he can, there’s no way he reads this, so does it really matter?

—

Until next time…

Johnny