Let’s face it, virtual conferences suck.

Don’t get me wrong, I think they’re great for our current climate, but they’ll never fill the shoes of a real in-person conference.

Queue CaboPress: the most unique conference you’ll ever go to.

Rethink what you know about a conference

After more than a year-and-a-half of Zoom, this past week I had a chance to return to an in-person setting with my peers and, oh boy… it was such a refreshing experience!

Right off the bat, I’m sure you noticed the name CaboPress. Yep, that’s right. The conference is in paradise, aka Cabo San Lucas, Mexico.

CaboPress isn’t like any other conference you’ve ever been to. First off, it’s 5-days long so buckle up for a deep dive. Secondly, it’s a curated list of attendees. Not everyone who wants to go, gets to go. Lastly, sessions and conversations take place in pools and relaxed settings like lunch and dinner.

Chris Lema, the organizer of CaboPress, is a well known speaker and business leader who created CaboPress to bring a different perspective to the conference model we’re all used to: jam packed, formal, and brief.

Chris Lema speaking at CaboPress 2021

I wanted to design a conference that would have people leaving feeling relaxed and refreshed while also being energized.

Chris Lema

This all sounds great in theory, but did he pull it off? IMO, yep!

Why CaboPress’ relaxed conference model works

WordCamp’s are great. I love attending, sponsoring, and speaking at them. However, they’re super formal compared to CaboPress’ standards.

Why’s this? People have their guards up. They’re all there for different objectives and it can be really hard to break through with people or even know who to talk to.

Quality attendees, quality conversations

It’s really hard to meet someone at a traditional 1 or 2 day conference and have a quality conversation. Heck, you’re lucky to get in a handful of in-depth and valuable conversations.

Not at CaboPress.

With a curated list of attendees, you’re talking amongst people who have been hand-picked and are all like-minded. They’re their for themselves, but also there for you too.

The attendees are either from product or service based businesses (or a mix of the two) and their expertise varies widely. If you need help with marketing, there’s someone for you. Have a question about product development? No problem. Some of the best and brightest minds in WordPress are in attendance.

CaboPress 2021 attendees. There were about 50 of us there this year!

Pool sessions

CaboPress is a place where you are encouraged to be vulnerable and let your guard down. The first step, getting into the pool.

Personally I have no problems getting into a pool with strangers. I’m from San Diego so have been doing it my whole life (more like the beach though). For others though, it can be quite a first step.

The pool sessions encourage you to take down your walls and open up in a safe space. You can talk about your successes and your failures. Both in business and in your personal life. What happens at CaboPress, stays at CaboPress.

Me enjoying the pool session. 🤙

Lunch groups

Chris knows each person in attendance and knows your skills and likely challenges. That’s why he chooses the best group for you to have lunch with, because these are the people he thinks can best benefit each other in closer conversation. It’s like being setup on a blind date for business! 😆

How this works is that our conference badges each have a number on them for our lunch groups. After the first day’s sessions are done we all find each other and then are free to go wherever we’d like for lunch. We just have to do it together.

Does he get it right every time? No. There’s bound to be some scratching their heads about their pairings. However for me, I found that I connected with each person in my lunch group this year.

My lunch group for CaboPress 2021

Covid protocols in place

Safety was on the mind of everyone this year. All attendees were required to show proof of vaccination or a negative test before the event began. Mexico is also very strict with their COVID restrictions.

During events in the pool we kept socially distanced and while walking around we were diligent with our mask wearing. In addition, we all were required to take a COVID test to get back into the US and I’m happy to say we all passed.

Should you go to the next CaboPress?

All business owners have struggles. It’s easy to silo ourselves from the outside world and try to fix them ourselves. This can be self defeating. You need peer collaboration in order to succeed.

If you’re constantly finding yourself in a vacuum, then CaboPress is for you. If you already have a mentor, are in a mastermind, and are already overflowing with feedback then perhaps not.

Personally, I’m thankful to have attended this year. It’s been a breath of fresh air, I made some great friends, and have countless takeaways that will keep me busy for at least the next year.

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