CaboPress 2017

We’re all pretty brilliant folks (especially you, since you’re reading this) and convincing us we could be more-brilliant about stuff isn’t always easy, especially anything that deals with our businesses, relationships, or visions for either or both.

We need evidence. We need proof that if we’re going to change up our strategies or approaches with our money-makers, they will actually work and not be another experiment or “valuable learning experience.” I mean, I like learning new things probably more than most people, but I am not a fan of re’learning something I already thought I knew.

The world is round – I don’t want to learn that it’s not – and CaboPress will teach you how to navigate the WordPress business world regardless of its shape. Here’s how I navigated CaboPress this year.

Reapply sunblock. Don’t forget your ears.

I’d hear this about a hundred times over the next 4 days, and was growing increasingly thankful with each passing 99 degree hour. CaboPress isn’t a vacation, but I suppose you could treat it like one. To get the most value out of the (purposely) limited time, you really need to enjoy it for what it is – a comprehensive, intensive workshop to prove you can improve.

Breakfast at 8.

It’s the most important meal of the day, I guess. I don’t usually eat it, which I guess says something about me. Coffee, eggs, bacon, and try to sit with people I don’t know yet.

This was when everyone was just booting up and readying themselves for the day ahead. Donuts, omelets, cereals, waffles; you name it, I ate it. Here we shared quick stories about ourselves, travels, accommodations, and what we hoped to get from the days ahead. Apply sunblock.

In the pool by 9.

Morning sessions start at 9 on the button. If you’re late, everyone will know because they’re already in the pool and you are not. There are 2 sessions going on at once, one on each side of the pool and usually a different pool each day. My favorite session was Syed’s (of WPBeginner fame) because he’s as passionate about converting visitors to customers as I am about open-sourcing my code. Probably more, actually; and he convinced me that I should be doing more, better, and different.

The pools weren’t private, which meant we were sharing them with all of the other people at the resort. Our swag package consisted of red Gilligan hats and water resistant lanyards, so our crowd stood out amongst all of the others. Not a day went by where someone didn’t ask who we were and what we were doing there. It was fun in a way. Of all the curious retirees, only two really engaged with me about anything – most just seemed confused. They didn’t know what they were missing!

I loved these pool-side sessions. Everyone was so comfortable, and relaxed, and the conversations were unlike any other WordPress related event I’ve experienced. The closest is the VIP Workshops in Napa Valley, which I adored and helped with a few years back. Don’t forget your ears.

Lunch at noon.

There were several restaurants on the resort, all of them had amazing food. My favorite was the Pollo Kiev I found on the final day, and it shot butter onto my swim shorts with my first slice into it, which is exactly what a good buttered-bird does.

We were broken up into very specific lunch groups of 6 people, and we ate with the same people every afternoon. I liked this, because it was really the only predictable interaction on any given day, and acted as a foundation for knowledge sharing across the sessions happening on the other side of the pool.

After lunch, we were free to roam about the resort until dinner. This gave us time to reflect and stash what we learned in the morning, and was really a great idea. We all took advantage of this free time to go snorkeling, take naps, hang out, get drinks, socialize, and get fancied up for a nice relaxing meal with new friends and cocktails. Reapply sunblock.

Dinner at 5.

I don’t usually eat 3 meals a day, but all this social learning meant I needed to keep my wits about me, and everyone knows you can’t do that on an empty tum-tum, so I indulged a bit each night with appetizers, desserts, and wines by the beach.

Each evening we were given a question for our dinner tables, usually about what we learned earlier in the day, but also about what we plan to act on to improve the general profitability of our businesses in the future. This really brought our groups together, and offered up a nice combination of what we each learned and how we’d apply it to one-another’s plans. Don’t forget your ears.


We were at breakfast by 8 every morning, so a healthy morning mind meant more than coffee and eggs, it meant a relaxing evening to wake up invigorated for everything the day had to offer up. No sunblock necessary here, since it’s dark by now.

Every night after dinner, some kind of event was occurring. Fireworks, fire juggling & dancing, disco, and so on. I pretty much loafed about in a pool or found a circle of CaboPressers to chat with about various odds and ends. I found this to be a really nice way to cap off each night, with the anticipation of more fun the next morning.


After reapplying sunblock all day, it’s time for a shower. Don’t forget to shower, otherwise you’re going to slime all that stuff into the bed and roll around in it all night, which is pretty gross. The rooms were spacious and comfy, the staff were exceedingly polite and accommodating, and the water was potable so there’s no worry about using it no matter the faucet.


With 60’ish attendees, it’s an intentionally intimate group, which helped solidify the relationships we all made while bobbing around in a pool together. This was 4 non-stop days of networking, but it was also the 4th year in a row, and my first. I hope I’m invited back, not just for the experience – which is amazing – but to share some success after applying what I learned, and to thank people in person for being so helpful and inspirational the entire year between.

You’ll probably notice I haven’t included any group shots, and not a ton of details about specific oooh’s and ahhh’s. That’s on purpose, really. All of us bonded in person with our stories and vulnerable moments, and that’s the kind of stuff you keep in your heart, not on your blog. And, well, I want you to consider coming next year and having these experiences yourself.

Thank you, Chris, for the invitation and warmth. Thank you, everyone else, for teaching, listening, and encouraging.

Reapply sunblock. Don’t forget your ears. We didn’t! ☀️