Industry Analyst & Strategist

CaboPress Breaks the WordPress Event Mold

I just returned from CaboPress and it is unlike any WordPress conference, period. I almost feel like that’s all the should be said, go to the site, read up on it, and you’ll understand. In short it’s a business conference created by the highly respected writer, speaker, and business coach, Chris Lema. It’s also much more than the sum of its respective parts: location, sessions, and networking.

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Cabo San Lucas and Pools

You can’t talk about CaboPress without referencing the Cabo part, Cabo San Lucas. The hotel sits along the coast, with all the sun you can imagine. Yes, it’s relatively hot and humid (for my taste) but that problem is solved by pools. And not just for enjoying, all the sessions and hours of networking happen in the water.

My first thought was that this would be uncomfortable, distracting, and just weird. I could not have been more wrong. Doing so much in the pools actually is comfortable, relaxing, and disarming in a way that makes paying attention to speakers, and each other a genuinely bonding experience. I haven’t spent that much time in the water in years.

It’s a brilliant plan, and with multiple other factors, keep the conference size intentionally small and intimate. Read the respective parts (event background) link above.


I was at every session slot. When was the last time you did that at any event. Usually the “hallway track” is where you’ll find me but not at CaboPress. Given the intentionally small nature of the conference there isn’t much else to do but more importantly, the speaker quality is beyond compare. This is a business conference for business folks, it just happens almost everyone attending has a WordPress relationship. None of the topics consisted of setting up a template, or developing a plugin. While those types of sessions are critical at a WordCamp – all of us attending are looking to grow and succeed in a competitive economy. The curated speakers covered partnerships, sales, pricing, strategy, and more. You could be an artisan woodworker and learned how to grow your business by 100% in the three days of presentations. Amazing.


So you’re in Cabo, relaxed, and surrounded by folks energized in growing their business and creating success. While you might “technically” be a competitor, the urge the collaborate and grow supersedes that kind of thinking.

You’re going to meet folks casually on Monday, you’ll be introduced to more during the sessions, and then a little bit of magic occurs. Chris creates for you a lunch pod, you’ll be having lunch together everyday (Tuesday through Thursday), and I can only speak for myself, my pod was amazing. They deserve shoutouts for the the inspiring conversations, meaningful advice, and camaraderie: John Doherty, Founder and CEO of Credo, and Chris Teitzel, founder of agency Cellar Door and Lockr.

Did I say a little bit of magic? I mean a lot of magic. Chris’s lunch pod curation was unbelievably spot on. We had a enough shared experiences, though in different types of companies, that may everything work.

The curation doesn’t stop at lunch, dinners are a bit more ad hoc however defined by a purpose and goals. I think I only had dinner with the same person once, groups are around four or five people.


Really simple:

  • Greatly improved and refined strategic thinking
  • New folks who I know I’ll be working with in my role at Cloudways
  • Fantastic tan
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