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My 100th Monogram Box

One hundred months of subscription boxes.

It feels almost unreal to say that out loud. That I’ve curated 100 different subscription boxes over the past 8 ½ years. And yet… here we are.

When I look back at where it started, I can still picture myself stressing over every tiny detail of that very first box. My “Lilly Pulitzer-inspired” box, packed in a plain brown craft box I stamped by hand. During the early days of my subscription box, more always felt better, so I just kept adding things, forgetting all about profit margins, and hoping my customers would be happy. 

Fast forward to today? My process, my confidence, and my profit margins look completely different.

From Brown Boxes to Branded Moments

That first year, I thought adding more products would make the box feel more valuable. But over time, I learned the magic is in the experience. The way the boxes make my subscribers feel. Instead of thinking that more is better, I choose one wow-worthy item and curate the rest of the box around it.

And the packaging? Let’s just say we’ve come a long way from those stamped boxes and logo tape. When I reached 100 subscribers, I finally ordered my first custom boxes in my signature turquoise. A few years later, we gave The Monogram Box™ packaging the full glow-up it deserved.

The Good, the Bad, the Never Ugly

Out of those 100 boxes, some stand out more than others, for better and for worse.

There was the box where FedEx left their truck door open, and my boxes ended up all over a busy road in my town (yes, really).

The “Oh My Gourd” box that I thought was funny, but many of my subscribers didn’t. Lesson learned - give them what they want! 

And the custom-designed green Christmas sweatshirt that subscribers still talk about – and still wear – years later.

Every one of those moments taught me something. How to plan further ahead. How to problem solve and pivot. How to listen (really listen) to what my subscribers wanted, even when it wasn’t what I expected.

Behind the Scenes

Today, we plan boxes 6–8 months in advance. I still start with one main item and build the rest of the box around it. And yes , I stopped packing boxes myself after about 45 of them when we moved into the Warehouse (the team kindly told me I was… in the way).

And my favorite hack? An automatic paper folder for packing slips. A little thing, but it saves so much time every month.

What I’ve Learned About Subscribers

You’d think by our 100th box I could predict exactly what my subscribers will love. But they still surprise me. Sometimes it’s the smallest detail that gets the biggest reaction.

So what keeps them coming back month after month?

• The seasonality. Their style needs change, so the box does too.
• The surprise. That feeling of opening something unexpected every month.
• The connection. They know I care about their feedback and use it to make each box better.

Apply My Learning to Your Subscription Box Journey

If you’re sitting at box #3 or #33 right now and wondering if you’re on the right track, let me tell you: you are. And if you haven’t launched yet, this advice is for you, too! 

• Consistency matters more than perfection. 
• Growth happens when you keep showing up, even when no one’s cheering you on yet.
• And more than anything, remember: building a sustainable subscription box business is a long game.

One box at a time, you’re building something bigger than you can see right now.

So keep going. Your 100th box is closer than you think.

Join me for this episode as I share the story of my first 100 subscription boxes and how the lessons they’ve taught me can help you reach your 100th box and beyond.