CaboPress 2021: Build Your Business In A Pool And Over Decadent Meals

Can you really advance your business at a conference where sessions happen in the pool at an all-inclusive, five-star resort? Of course!

CaboPress Afternoons

There is something magical that happens when you’re at the coast; when you’re looking out over the vast expanse of sparkling blue ocean in front of you, watching the surf slide in and out over the sand, and listening to waves crash melodically over the rocks and across the shore.

As you close your eyes, take a deep breath in, and blow it out slowly a peaceful calmness settles over your body and mind — and suddenly, the world seems much bigger, your obstacles and challenges seem much smaller, and everything you dream of seems possible.

There is something magical that happens when you’re a part of an intimate group of like-minded people; when you’re surrounded by others who walk a similar path, understand your daily life like no one else can, experience similar challenges, and are working toward similar goals.

As you let your guard down, open your mind, and allow yourself to be vulnerable, it creates a space for meaningful connections — and suddenly, you’re navigating deep conversations about everything from sales and revenue to managing and growing a team to personal and professional satisfaction.

There is something even more magical that happens when the two come together to create a transformational experience; when you’re immersed for several days in conversation with like-minded people — at breakfast, in pools, over lunch, at dinner, and on the patio at night — along the coast, with the ocean in the background, which is exactly what you experience at CaboPress.

CaboPress Collage With Group Photo

What Is CaboPress?

Hosted by my friend Chris Lema, CaboPress is billed as the best business conference in Cabo. Brian Clark says it should really say best business conference in Mexico, and while I think every attendee would agree, I’d argue that CaboPress is the best micro-conference period.

Not because the session topics are carefully planned and the session hosts are selected specifically for the topic.

Not because the attendees are hand-picked from far more applications than there are spaces and highly curated to ensure that everyone can learn from each other.

Not because every detail from your ground transportation to your lunch group to your dinner conversation topics and even optional morning workouts are carefully planned to help you get the most out of the event.

Not because the event favors conversations, discussions, and authentic interactions over prepared presentations and slide decks.

Not because it takes place at a stunning, all-inclusive, five-star resort in Cabo with incredible restaurants, fabulous drinks, beautiful pools, a world-renown wine spa, and impeccable service.

It’s because of the schedule.

Unlike other conferences that run you ragged and overload you with information, at CaboPress, you have time to learn, consider, and ponder. You have the space to think through an idea that pops into your head during a session and chat with others about it to flesh it out.

  • Early mornings at CaboPress are optional. Join the early crew for a beachfront workout or hit up the breakfast buffet — I loved snagging a made-to-order omelet, bacon, potatoes, and fresh fruit every morning!
  • The event kicks off each day at 9:00 am with two back-to-back sessions in a pool. During each time slot, one session is geared toward product businesses and the other is geared toward service businesses. You attend the sessions most relevant to your business where hosts share information then facilitate a discussion with attendees.
  • You have lunch with the same small group each day at the restaurant of your choosing. This not only gives you the opportunity to get to know each other better but a chance to talk through and further explore topics and ideas from the morning sessions.
  • Afternoons are considered free time. Some people walk on the beach and feed the fish. Some people visit the spa. Some people take naps. Most, however, congregate in a beautiful pool overlooking the beach to share personal and professional stories, ask for and give advice, dive deeper into topics from the morning sessions, and strengthen new and existing relationships.
  • Everyone attending CaboPress comes together again in the evening so Chris can share event announcements, provide instructions for how to find your dinner group, and hear the discussion prompt for the night. Then the groups spread out across the resort restaurants for amazing meals and conversation.
  • Finally, the day ends as everyone congregates on an outdoor patio to relax, hang out, enjoy some drinks, and smoke cigars. These casual evenings under the stars are a great way to wind down the day.

Fair warning: As you may be able to tell from the photos included in this post — most of which were shot by the amazing Shawn Hesketh of WP101) — CaboPress will ruin you for all future conferences to come.

Photos Of Chris Lema's CaboPress Event

CaboPress And Covid

CaboPress = my first airplane ride and business travel since March of 2020. As the event drew near, I felt a mix of excitement and trepidation. I couldn’t wait, yet I had a bit of regret. Even vaccinated, I was nervous to be in an airport and on an airplane. In the United States, I felt uncomfortable. People in the airport were unmasked and many didn’t respect personal boundaries. In Mexico, I felt far safer in every situation. From the airport to the resort to the marina, it was obvious that Mexico takes COVID more seriously than the United States.

Grand Fiesta Americana Los Cabos, the resort where CaboPress was held, handled COVID protocols professionally and respectfully.

  • They took temperatures upon arrival as you entered the hotel lobby.
  • All staff members wore masks, clear safety glasses or face shields, and when appropriate, plastic gloves.
  • Hand sanitizer was everywhere and use was encouraged by staff.
  • They took temperatures at the restaurant hostess stands before checking in and seating your party.
  • Room service orders were wrapped in plastic.
  • At the breakfast buffet, staff plated all of the food for you.
  • If a guest wasn’t wearing a mask, they were asked to put one on.

CaboPress brought together 50 people, everything for the event was held outside, and all 50 people tested negative for COVID at the end of the event — the hotel scheduled and administered the tests in their medical clinic.

CaboPress Photo Collage

The CaboPress Secret Sauce

This was my seventh CaboPress and yes, spending a week at a gorgeous resort in Mexico with incredibly smart people is pretty magical.

It’s even more magical coming out of a pandemic when everyone feels blessed and grateful and happy for genuine human interaction. I don’t think any of us quite realized just how much we missed this until we arrived.

But that’s not the real magic…

The real magic of CaboPress is opportunity.

Chris creates opportunities for attendees to connect with exactly who they need to connect with based on their business challenges and goals. The kicker though is that it’s not always obvious who that is — and he may not even tell you. He does it on purpose to encourage you to speak with everyone.

Every single person at the event was selected or invited for a reason and by not seeking out time with each host and attendee, by not asking about their businesses and lives and sharing details about your own, you limit your opportunities to learn and grow.

You see, when you invest in others, they also invest in you.

CaboPress won’t improve your business, provide priceless insights, create ah-ha moments, or increase your revenue — unless you make it happen. You get out of this event what you put into it. It’s up to you to seize the opportunity to:

  • Build a relationship with someone new and discover commonalities you never could have imagined.
  • Deepen an existing relationship with conversations that touch your core.
  • Share an obstacle or challenge and get advice, ideas, and fresh perspectives.
  • Talk about a bold goal and tap others for insights on what to watch out for and how to reach it faster.
  • Run a new idea past unbiased, neutral third parties and get honest feedback.
  • Seek out what you need and keep seeking until you find it — again, the gold nugget that changes everything may come from an unlikely source.

CaboPress Business Conference Sessions and Sunset

Is CaboPress Worth It?

You may be wondering, “What did I get out of CaboPress?”

My answer: EVERYTHING.

I came to CaboPress with some thoughts about changes I wanted to make with Profitable Project Plan and Content Camp — things I was considering but not sure about. I also came ready to talk through some challenges with my services business, an idea for something brand new, and some rough thoughts on refinements to my personal brand niche.

  • I arrived with uncertainty and left with total clarity.
  • I arrived with a challenge and left with a solution.
  • I arrived with an idea and left with the groundwork already laid to implement it.
  • I arrived with a raw, messy idea and left with a clear plan.

I arrived with high expectations and no attachments.

I went with the flow and chatted with everyone I could, and I’m excited for a few new things brewing with potential partners. I also was able to spend invaluable quality time with friends — which was exactly what I needed mentally and emotionally — and getting a couple of spectacular massages didn’t hurt either!

So, is CaboPress worth it? Hell yeah.

As with years past, I left Cabo with the entire next year — for my services business, my courses, and my personal brand — mapped out and prioritized. And, just when I wrap it all up, it will be time to do it all again at CaboPress 2022!

Will I see you there?