My First CaboPress Experience

If you had told me one year ago that I’d be traveling internationally, I would not have believed you.

If you had told me I’d also be speaking in a pool at a conference, I would have laughed.

But indeed both came to pass in September’s CaboPress, an intimate mastermind event in Cabo San Lucas, Mexico, organized by Chris Lema. When I was invited to be a host (more on that in a minute), I was thrilled to meet the amazing people that Chris surrounds himself with in business. Having spoken at events with him over the years, I knew that if iron sharpens iron, this event was the place to be.

After attending, speaking and reflecting on the experience, there are 3 elements that make CaboPress the best business conference in Cabo San Lucas.

1. Location, location, location

Ever spent thousands of dollars and days of your life to sit in a crowded ballroom, elbow to elbow with strangers, struggling to keep up with a dozen slides a minute and wondering when the hell the speaker was going to break for lunch?

I can’t tell you how many events I’ve been to where the city is simply chosen for the fancy stock photos on the sales page. The city doesn’t matter, you’re not going to see it. Little thought is given to the watering and feeding of hundreds – or thousands – of attendees, several events had such tight breaks that I left my lunch table having never received my meal.

Spending months developing great content matters less when your attendees are fighting off yawns, freezing cold sitting on uncomfortable chairs trying to balance a journal and notebook and water bottle and where did my pen go?!

It doesn’t matter how captivating the presentation, your surroundings matter. Not only is the CaboPress resort absolutely gorgeous, with all the amenities you could ever want, it is spacious – as is the design of the event.

2. Intentional Design

Each attendee had a name tag with a number indicating the small group with whom they’d eat lunch. These groups were intentionally arranged to foster conversation, collaboration and to mix people up so alumni met first timers (you do need to have alumni who can point out the best items on every restaurant’s menu).  Lunch was scheduled immediately after the daily sessions which happened, as I mentioned, in the pool.

The pool is not a great space to take notes or type on a laptop, granted, but in every single session I took away exactly what I needed and it stuck with me because it was important. Compare that to the events where I have a notebook full of junk, every speaker’s every bullet point, and have never reread or used that information.

There are just two simultaneous sessions to choose from, one designed for service providers, one geared more toward product developers and both are held in the same pool so if you’re interested in both you can casually swim between them. And with doubled up sessions there are only 4 per day. 9am-noon. That’s it.

All of this is intentionally created for the value to the participants, not the ego of the organizer or a financial goal.

There’s no pitching. No “follow me and join my newsletter list.” No bit.ly link to download slides.

Glorious.

And after lunch, to digest ideas and tacos, is an optional swim in a pool with drinks and good conversation. This is where I had some of the best conversations and met some amazing people.

3. The People

Ever heard the question, “if you could have dinner with 3 people, who would you choose?” I swear that must be running through Chris Lema’s mind as he extends invitations and accepts applications to CaboPress.

While it’s unrealistic to think that everyone at a 50 person event will love each other all the time, this was a room of sharp people with incredible ideas and insights, an amazing ability to implement and innovate and a willingness to generously share what is – and is not – working right now.

Somehow egos fall aside when you’re having your third Sea of Cortez and talking to someone in your swimsuit. Barriers are literally striped away and vulnerability comes faster.

Plus, Chris just doesn’t invite the people who would be pushing their business, trading business cards, angling for a collab. Get the right people in the space and amazing things happen.

As a host, my goal was to share ideas, ask questions in my session and guide a conversation where the contributions of an attendee in the pool was as valuable as my own. Every session brought ideas, insights and ah-ha moments from both the host and the other attendees. I would argue that every event should take advantage of the collective wisdom in a room but when you’ve got 3,000 people with varying levels of experience and, let’s just say, social awareness then it’s not possible.

If it sounds like I believe old events are dying it’s a prediction that’s as obvious as “people hate zoom meetings.” 

The thought of going back to a ballroom and sitting on those stackable chairs with a 40-45 lb “workbook” to be pitched another product, another mastermind group, another affiliate opportunity is unpalatable.

I do understand that this old school type of event is intentionally designed to break down your defenses. If you’re not afforded time to rest, recover, eat and relax and pushed into situations where you feel overwhelmed and lost then you are much more likely to purchase additional pitched products or programs.

CaboPress is different and I’m so grateful for the experience I had and to Chris for curating such an amazing group.

Note: I’m uploading this without all the photos I wanted to include because WordPress is throwing a fit today. Imagine beautiful beaches, tacos, booze… all the good stuff.