This was my first CaboPress, my first time in Cabo San Lucas, Mexico, and my first business conference since COVID. And honestly, it may have set the bar too high for any future conferences.
CaboPress is anything but a typical conference. There are no convention halls, no windowless rooms, and no crowds of people wandering between booths. Instead, it’s a carefully curated business experience—part mastermind, part conference—hosted by Chris Lema.
CaboPress is at a stunning 5-star all-inclusive resort in Cabo San Lucas, Mexico. Everything is taken care of—food and accommodations—and unlike other conferences, there is no Ubering to and from different venues, so you can focus entirely on the experience.
The sessions are held in the pool. Yes, you read that right, in the pool. They last about 30 to 45 minutes, with the remainder of the time dedicated to Q&A and discussions, which makes them both impactful and easy to digest. These intimate talks feel like fireside chats, filled with storytelling, business insights, and shared experiences. There are two sessions each day, with the afternoons free for you to spend as you wish. However, most CaboPressers (let’s coin that, please) head to the pool to network and continue the business discussions. While the sessions were fantastic, the networking was even more powerful, as we could dive deeper into the topics and learn how others handle clients or improve processes.
After the morning sessions, there’s a daily lunch break. The lunch group remains the same throughout the event, allowing you to connect deeply and reflect on the morning’s material. Chris Lema carefully curates these groups, and it shows. Everyone in my group had similar business challenges or were at comparable stages of growth, making the conversations highly relevant and valuable.
Dinners were the final part of each day, with different groupings every night. This allowed me to interact with a wider range of attendees, and each evening brought new topics to discuss. Again, all meals were part of the all-inclusive package, and the quality was exceptional. While most all-inclusive resorts aren’t known for 5-star dining, this one came pretty close!
The result of this setup is meaningful, intimate conversations. I didn’t just meet talented consultants, coaches, and potential vendors—I also connected with people I hope will become good friends.
Now that I’ve covered how the conference is different and how it works, I can dive into the real substance: the impact it made.
The sessions were truly eye-opening and packed with valuable insights. The content was directly relevant to the challenges I’m facing and aligned with my business’s current growth stages. I can’t emphasize enough how impressive the other attendees were—successful and highly knowledgeable in their fields. Many had large social media followings and personal brands I’ve admired online, so meeting them in person was a remarkable experience. I mention the other attendees again because, during the Q&A sessions, their questions and discussions were thought-provoking, often diving deep into challenging topics that even the speakers had to carefully consider before answering.
The sessions and people I heard talk were:
The sessions were well-structured but still had a laid-back vibe. I could relax in the pool, soak up the sun, listen to insightful talks, and then ask tough questions about the challenges I’ve been facing—questions that directly related to the topics being discussed. I walked away with a list of key takeaways from the conference:
After a week in Cabo, I left feeling a bit tired—and maybe a little sunburnt—but completely energized. I was ready to dive back into work, implement the strategies I’d learned, and share the newfound knowledge with my team. Beyond that, I felt a genuine reset. While I do take vacations, this experience was different. I was able to truly relax and connect with so many like-minded individuals. Someone mentioned how all the conversations were in-depth because everyone there was not only smart but truly understood the nuances of business. It’s rare to gather such a brilliant group of people in one place, discussing everything from business strategies to spies (IYKYK), complex accounting, whether we’re living in a simulation, or how to hire international employees without using a company of record like Deel.
I am looking forward to hopefully being invited back and meeting old faces and likely some new ones. I highly encourage anyone running an agency, SaaS, or business online to attend this must-attend event.
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