A Review Of CaboPress, A Mastermind-Style Event By Chris Lema

A review of Chris Lema's CaboPress event, including a peek inside the event, why attendees find it so transformational, and my thoughts on small conferences and tiny events.

I recently returned from one of my favorite business events of the year — CaboPress. It’s a small conference meticulously planned and organized by Chris Lema that brings together a group of business owners for three full days of transformative experiences.

CaboPress is an event like no other and it may just ruin all other events for you.

The event is held at the Fiesta Americana Grand in Los Cabos, a spectacular five-star resort with impeccable service, gorgeous rooms, amazing food, stunning pools, and incredible views. The resort is also all inclusive, which means all food and drinks of all types are included — and they don’t skimp on the quality either. I think we all ate like kings.

Speaking of pools, all of the sessions are held in the pool. Not near the pool or by the pool, but in the pool, in your bathing suit (and a swim shirt if you’re smart). This means you don’t have your laptop or phone (mostly) and instead, you’re fully engaged in the sessions. And, let me just say that when you’re in a gorgeous infinity edge pool, looking out over the sandy beach to the ocean, with palm trees swaying in the breeze, you can’t help but relax and let your guard down.

CaboPress Sessions in the Pool
At CaboPress, you’re not sitting in a conference room listening to presentations, you’re in a pool participating in the conversation.

An Event Designed With Purpose

What’s really unique about CaboPress is the way it is designed.

There are only four 90-minute sessions each day, two at 9:00 am and two at 10:30 am. This means that each day:

  • You only attend two sessions in the morning, which means you’re gaining value information and insights, but you’re never hitting that point of overwhelm or feeling like it’s too much. And, if you’re not feeling the session you’re in, or you just want to check out a little of both, all you have to do is swim across the pool.
  • You enjoy lunch with a handpicked lunch group you get to know very well because you have lunch with them each day. What’s wonderful about this is day it provides time to recap the different sessions attended and talk through any of the things that bubbled up for you.
  • The afternoons are unscheduled and open for you to spend them anyway you wish. Most people head back to the pool to hang out, enjoy beautiful cocktails, get to know the other attendees better, and talk more about what’s really going on in each other’s businesses.
  • The whole group reconvenes for dinner and with instructions from Chris on how to find a dinner group and one topic to discuss at dinner, we all split up and head to one of the many restaurants to choose from for a fabulous meal and more casual conversation that is truly powerful.
  • After dinner, again the time is yours to spend it how you wish, but most people converge on an outdoor patio for drinks, cigars, and more conversation.

If you haven’t figured it out yet, CaboPress provides just enough structure to ensure you walk away with true value, insights, and information to move your business forward without overwhelm. The rest of the event is all about making personal connections, having meaningful conversations, allowing yourself the downtime needed to think through the ah-has and ideas you get, and getting past the places you have felt stuck.

The Fiesta Americana Grand In Los Cabos
CaboPress is held at the all-inclusive Fiesta Americana Grand in Los Cabos, an incredible five-star resort.

An Event Without Speakers

I told you that each day, there are four sessions available to choose from, so you can attend the two that best fit your needs. But CaboPress doesn’t have any speakers, instead it has hosts.

CaboPress hosts lead the sessions and act not as speakers delivering a polished presentation, but as a session guide and facilitator that gets the session going, shares their personal experiences and insights, and then engages the entire group in an interactive discussion where everyone is invited to share what has worked or not worked for them, ask questions, and answer questions.

With hosts there to guide the session and keep it on track, attendees benefit from the collective wisdom of everyone attending the session—and sometimes the greatest nugget of information an attendee will get or biggest ah-ha they will experience will come from another attendee jumping in and sharing. As a three-time CaboPress host, I have to say, it’s pretty fantastic to watch it all unfold and see attendees participate and react to the group dynamics.

CaboPress Hosts Lead Discussions
Here’s a quick snapshot of the High Value Courses discussion I lead as a CaboPress host.

Small Events Make Big Differences

Small events like CaboPress with about 40 people, and tiny events like retreats with around 10 people are where it’s at for me. While I love big conferences and the networking, and the parties, nothing compares to the experiences and connections small events deliver.

Over the past thirteen years, my biggest business breakthroughs and the ah-has and ideas that have led to my most profitable decisions have almost all come from small/tiny events where I was really able dig into my business and focus on what I need most, what my goals are, and what needs to happen for me to achieve them—and have the meaningful conversations with others that simply wouldn’t happen at a large event where you’re “on display.”

Small/tiny conferences and events allow you and everyone else there to relax, let your guard down, and be real and fully present. It’s why you rarely saw anyone at CaboPress on their phone or behind a computer. It’s also why so many people got home and wished they actually took some photos. When you’re truly in the moment, you’re not thinking about documenting who you’re with and showing everyone else on social media what you’re doing, you’re engaged with others and building relationships that will impact your business in ways you may not even begin to imagine.

The importance of this type of event and experience in my business and personal growth is what drove to me to finally create the Accelerate Retreat for women business owners. I want to create a similar experience for other women, but with masterminding, hot seats, and facilitated exercises and time to bring an idea to life and create a plan to make it happen.

I see so many women who are already strapped for time invest in attending big events and come home fired up with all sorts of ideas, only to get waylaid with all the distractions and demands of everyday life. Implementing those ideas get delayed because there is no plan in place to follow, and soon months go by, and then it’s been a year and you still haven’t achieved the goal you set for yourself when you came home from that conference.

If that sounds familiar, you’re not alone. It happened to me with the first several conferences I attended and it happens to thousands of women around the world every year. I created the Accelerate Retreat to prevent that from happening. I believe that any goal is achievable when you have a plan in place and a map to follow, because then you know exactly what to do and you can take baby steps or large leaps — whatever fits into your schedule.

CaboPress 2018
While not everyone made it down for dinner in time for the group photo, this group of people are some of the smartest and most giving I’ve had the pleasure to spend time with.

The Scary Part Of Small Events

I’m not going to lie, small conferences and tiny events can be scary. You can’t hide at a small event. There isn’t a back row and there’s no faking it. You show up as you are, real, vulnerable, and open—and trust me when I say your impostor syndrome is going to kick in big time.

This was my fourth CaboPress and my third as an event host and I’d be lying to you if I didn’t let Chris know more than once before the event that he didn’t have to invite me and it was okay if he didn’t want me to be a host. I told him we’d still be the best of friends — Chris is like the brother I never had—and it wouldn’t hurt my feelings if he wanted to invite someone else to be a host, someone more qualified.

Of course, Chris told me I was being stupid (but he said it in a nicer way), and I still fought him. I told him that every time I looked at the roster of hosts, I kept hearing that song from Sesame Street, “One of these things is not like other, one of these things just doesn’t belong.” And again, Chris told me to knock it off. I think I was actually irritating him!

Then once at the CaboPress, when surrounded by incredibly successful, brilliant, smart, accomplished individuals, my impostor syndrome kicked in again. I wondered, “What could I even offer these people that would be of value?”

But then I led my session on creating high value courses — it was the one of the two first sessions on the first day — and it went fantastic. Several people approached me throughout the event about the value that came from that session and I got more comfortable and more relaxed and was reminded that I do have my crap together, I have achieved some great things, and I do life very differently than many other people… and have insights on work/life balance that help others in a way that’s bigger than increasing profits by X% (although that’s important too).

It also has been great to receive follow up messages from attendees after the event about the impact something I shared with them had. Some people have already made changes in their life as a result and nothing could make me happier.

The funny thing is that this happens to me with CaboPress every single year. My impostor syndrome kicks in and I freak out, which is why reading the recap posts from other attendees has been so wonderful. Several of them admit to feeling the exact same way and having major impostor syndrome at the start of the event!

So if you ever feel like that… If you ever feel hesitant to register for a small event because of impostor syndrome… Be brave and do it anyway! You won’t regret it, I promise.

One of the Gorgeous Pools at The Fiesta Americana Grand Los Cabos
One of the gorgeous pools at The Fiesta Americana Grand Los Cabos where the CaboPress sessions are held.

What’s Next After CaboPress

Now that CaboPress has wrapped I have a short list of big things that I want to implement and accomplish:

  • Big changes are coming to my agency, Bourn Creative.
  • Clarity about my course offerings is providing major momentum for some new things.
  • I’m excited to be hosting the Accelerate Retreat for women business owners this February (spots are still available).
  • And, I’ve got something totally new in the works that I’m really excited about.

The most important thing about what’s next is that I have a plan. If there is one thing I’m really good at, it’s breaking complex things down into simple steps and pieces. So I’m working the plan and implementing one thing at a time as it fits into my schedule.

Why not move faster? Why not work more hours? Why not hustle harder?

Because as much as I want to achieve my goals and create success, I also want to live inspired, embrace imperfection, and pursue an unbalanced life — one that allows me to enjoy every day and go to sleep every night feeling fulfilled.

If you’re not experiencing that in your life, maybe it’s time for a change.

Maybe it’s time to consider applying for CaboPress next year, joining me at the Accelerate Retreat, or finding another tiny conference or retreat that best fits your needs.

Some links used on this site are “affiliate links.” If you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

Make Things Easier

Get exclusive offers, insights, and resources to help grow your business with more clarity and greater ease.

Sign Me Up!

Pick My Brain

No long commitments or big packages, just quick advice, paid by the minute, right when you need it.

Book A Call!