CaboPress: Connections and Conversations that Matter

With the ongoing health crisis affecting us all, these are challenging times. So it helps me to reflect with gratitude on time spent with close friends, until we can meet up in person again. My friend, Chris Lema, has impacted my business—and my life—in immeasurable ways. And his event, CaboPress, is like no other. Here’s why I can’t wait for the next one.

First of all, we’re not in Cabo right now. Instead, like most of you, we’re staying home and honoring the lockdown guidance, while closely monitoring the ongoing health crisis that’s impacting us all. These are tough times. So it helps me to reflect and be grateful for time spent with close friends, until we can meet up in person again.

Hesketh and Lema Kids in Cabo

I’ve worked from home for over a decade, and we homeschool our three kids. So, not much has changed in terms of our day-to-day routine. Still, we miss being able to travel and visit with our friends. And that brings back fond memories of the many family trips we’ve been fortunate to take in recent years.

Back in October—which seems a lifetime ago—we traveled to Cabo with our dear friends, Chris and Melissa Lema, and their two awesome kids. We spent the first couple of days relaxing and playing together as families, enjoying some much-needed downtime.

Over the week that followed, we attended Chris’ business conference, CaboPress. This marked my third time to attend this highly unique event.

Chris hosts CaboPress at the beautiful, five-star, all-inclusive, Grand Fiesta Americana beachfront resort. It’s a perfect location to relax and recharge while reflecting on your business. The restaurants and food are exceptional, and each one offers postcard views of the Pacific Ocean.

Beautiful Grand Fiesta Americana in Cabo San Lucas
Beautiful Grand Fiesta Americana in Cabo San Lucas
CaboPress Group

Anyone who’s attended CaboPress will tell you that Chris carefully curates the entire event, from the attendees—who apply months in advance—to the hosts, and even the topics discussed during each session. This creates a relaxed atmosphere in which business owners feel safe to openly share about their business (and personal) challenges.

As a result, every participant is highly engaged, committed to giving and receiving advice from each other. It’s an incredibly diverse group of smart, talented business owners who are eager to learn and share transparently from their own experiences.

To a large degree, it’s the caliber of the people who attend that have made CaboPress the impactful event that it is.

If you’re like me, you’ve been to countless conferences where you sit all day, listening to a seemingly endless stream of presenters, most of whom are merely reading their slide deck aloud to a room full of half-awake people. Conversations with other attendees are relegated to small breaks between sessions, or perhaps an after-party.

But at CaboPress, the entire focus is on those discussions, not presentations. So, get this…

Every session at CaboPress is a group conversation that takes place in the pool. The discussions are moderated by hosts, but the most impactful takeaways just may come from the person right next to you!

This year, Chris invited me to facilitate one of the group discussions, on the topic of telling better stories using video. I shared a simple storytelling framework based on the classic “hero’s journey” template. Then we talked about how to use that framework to create more compelling videos that will better connect with the audiences we serve.

Shawn Leads a CaboPress Conversation

During the discussion, several people shared creative ways they were already using video. Then, we brainstormed ways to leverage this storytelling approach to not only make better videos, but also more effective email campaigns, sales copy, and even improve homepage verbiage.

And that’s the kind of practical insights and strategies people take away from CaboPress. Not a bunch of high-level, abstract platitudes, but real-world advice you can apply to your business the day you get home.

The best part? The sessions only take place during the morning.
After the morning sessions, lunches are shared in small assigned groups. Afternoons are free, so there’s plenty of time to unpack ideas, connect with others for meaningful conversations, or just relax and enjoy the gorgeous surroundings.

Each night, we were split into small groups to enjoy dinner at the stellar restaurants around the resort. And the conversations continued after dinner, well into the night, while many of us enjoyed a nice cigar, which was always paired with plenty of laughter.

And that’s kind of the whole point.

It’s impossible to leave CaboPress without being challenged, encouraged, and inspired to do your best, most meaningful work. But the most important takeaway for me has been the friendships I’ve built at CaboPress, which continue long after we’ve returned home.

And it’s those friendships that I find myself missing the most right now, while we’re under quarantine.

Sure, we’re making the most of this time, scheduling Zoom calls as often as possible. But there’s just no substitute for being together, face-to-face, enjoying a meal together, or a meaningful, late-night conversation.

I’m reminded of this quote…

“Be around the light bringers, the magic makers, the world shifters, the game shakers. They challenge you, break you open, uplift and expand you. They don’t let you play small with your life. These heartbeats are your people.”

— Danielle Doby
Chris and Shawn in Cabo
Hesketh Family in Cabo

Chris, I know I speak for every CaboPress attendee when I say that we’ve all been impacted in immeasurable ways because of your investment in our businesses and lives. Thank you for modeling generosity, excellence, and service to us all. Every time I’m around you, I’m challenged to level up. And for that, I’m incredibly grateful, my friend.

To the rest of you, may you find ways to stay connected with others during this challenging time. If I can be of help in any way, please feel free to reach out. And if you’re serious about taking your business to the next level, you owe it to yourself to follow my friend, Chris.

I hope to see you soon. In fact, let’s meet at CaboPress!