Oak Drive Monthly Update - May

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

One other major development this month: Johnny and Mallory welcomed their first child into the world.

Mother and baby are doing great, and we're all excited to meet the newest member of the Oak Drive team.

Naturally, Oak Drive took a back seat for a bit while Johnny enjoyed a very generous one-week paternity leave.

Now that I mention it, it kind of feels like he's been on paternity leave for a while.

I know we've been talking about these shirts forever, but they're finally on their way from Peru.

It's been a long process getting to this point, but they're finally making the trip across the ocean and into our hands.

There's still plenty to do once they arrive. We need product photography, product pages, and a handful of finishing touches before they're ready for launch.

Hopefully the next update includes actual shirts delivered to our warehouse manager (aka Johnny) instead of me continuing to promise that they're almost here.

Also, for anyone unfamiliar with how tariffs work, we'll be paying an extra 10% on top of our purchase order to the U.S. government. As if they don't already get enough of my money.

Thanks for that one, Trump.

We got our first sweater sample from Peru this month, and it gave us a pretty clear picture of what we don't want.

I was basically swimming in the damn thing.

Even after carefully measuring reference sweaters, putting together a detailed tech pack, and even using the metric system, I thought I had removed just about all room for interpretation. Apparently not.

Looking back, the fact that I expected them to get it right the first time might be the funniest part.

The good news is that the material itself is great. We just need to dial a few things in.

At this point we've learned that every sample comes with a new lesson, whether you asked for one or not.

Moving on to other mildly infuriating things.

I've been battling to get our hats across the finish line. The sampling process has been tough. Fonts get changed, embroidery comes out looking awful, or some other detail decides it wants attention.

That said, I think we're finally getting close.

We've had the artwork professionally digitized, gone back and forth with the factory more times than I'd like to admit, and have gotten to a place where Johnny is almost happy.

For those who haven't met him, that's about as happy as he ever gets.

We'll see.

Such is life.

A lot of our time this month was spent working on the website.

Our goal isn't to launch a generic Shopify store with our logo slapped on it. We want Oak Drive to feel unique and polished from the moment someone lands on the site.

That means working through photography, layouts, copy, product pages, and all the little details that people never notice when they're good but notice when they suck.

The website is still a work in progress, but the plan is to launch a much more complete version once the shirts arrive and we can photograph both the tees and hats.

We're getting there. Slowly.

But we're getting there.

Until next month,

-Nick