Packing Orders with My Mum and Learning the Hard Way 🔴
Inside a week of founder guilt, unexpected lessons, and bold bets on our next move.
I am writing this with my carry-on open on the floor, planning the next week of travel, and feeling a little scattered but also grounded in why I even do this.
This week was messy and special in equal measure. It reminded me that building Sleep or Die (especially in beta mode) is not just about big brand moves or sales numbers but about the small moments that make all of it matter.
If you're new here or you’ve been around since the early rants and raves, thanks for reading. It means a lot to have you here.
A Win I’ll Always Remember 🔴
My mum came to visit for the first time in two years, and this trip was a big deal. We all wanted her to feel at her best. She was only here for four days, but I’ll remember those moments forever.
It was so special to have her see a slice of my world, even if startup founder world can be disorganized and messy.
She came to help me pack up Sleep Tape orders I had to send Canada Post (the ones not handled by our 3PL). Honestly? I didn't expect it to matter much to her. But as she carefully tucked each order away, she told me she felt important. She created stories based on the customer names and gingerly applied each shipping label.
She felt that she had accomplished something real. That she was helping people sleep better, sleep hard, and truly contribute to Sleep or Die’s mission to revolutionize how we think about sleep.
It was such a good reminder that these small acts are the big things.
Of course, the founder guilt was real. She was only here a few days, and I kept bouncing between wishing I was with her when I was working, and thinking about work when I was with her. By Friday, I finally let myself sink in and just enjoy being together. We’d already had our morning at the office. Things were humming along, even if there was more to do.
The WTF of the Week 🔴
File this under “never assume anything.”
A month ago, I shipped back a bulk package of inventory to avoid duties and thought it was handled. Turns out it never actually made it to our 3PL. I only found out last week when we were down to a handful of Sleep Tape left. Cue stock-out stress.
I was definitely shocked. It was a gut-check that if you don't add something to your reminder list, no one else will either. Quick follow-ups are always worth it.
Thankfully, my 3PL was fantastic. Daily emails, constant support. And luck seems to be on our side. It should arrive early next week, just in time for our partnership with 4AM Skin.
The Gut Check on Launch 002 🔴
We received our latest packaging samples after our first major pivot, and they’re still not there yet.
Honestly? If you sat down to design sleep strip packaging in your mind, it would look exactly like this. Expected. Straightforward. Safe.
But we're not in the business of safe. We're doing something revolutionary in sleep, and the packaging needs to match that. I want it to feel as bold as what we're building. As disruptive as our mission.
If you're a paid subscriber, head to this week's poll to help us decide just how wild we should get:
Looking Ahead 🔴
Next week is a whirlwind. NYC Tuesday. Toronto Thursday. A wedding Friday. Then a few extra days in Toronto before heading back to my favourite place at my favourite time of year: home in Vancouver.
Honestly, this is the best season in Vancouver, so it’s bittersweet to be travelling. But there’s something about New York City that just hits different. The energy. The connections. It always makes me feel like the sky is the limit.
I’m especially excited to catch up with Annie and Kelley, two of my favourite mentors from Dream Ventures who always have the best perspective.
Bold and Cheeky Closing: Don’t Sleep on This 🔴
If you're reading this, you're part of why Sleep or Die isn't just a brand, but a growing movement.
Tell me: what would you want to see us try next? What’s a marketing idea so ridiculous it might actually work? Drop it in the comments.
We don’t exist to do what’s expected. Let’s keep pushing.