The Conference So Good I Created a Site Because of It

I attend a lot of conferences every year, just ask my family. I count myself blessed to be able to travel all over the world, experiencing new cultures and experiences, all while sharing what I’m passionate about. In fact, I’m writing this enroute to my last conference of 2018. Looking back at all the miles traveled, countries visited, and great conversations I’ve had, one conference stands out above the rest: CaboPress.

Let me set the scene: I walk off the plane in Cabo and it’s like any other airport I’ve been at in the world. This one happens to have a lot more people in flip flops, sun hats, and their best Jimmy Buffet gear. Waiting in line for customs was a grueling process where everyone is just ready to be in Margaritaville and not in a line to get your passport stamped. Once through, I head outside to the taxi wait where I see a familiar face, Tony Perez, and we get in a van and head off to our hotel.

At this point I have no idea what’s in store for me. You see, I’ve already been to a few conferences in the past few weeks, along with just coming from a family cruise to…. yup you guessed it Cabo/Mazatlan/Puerto Vallarta. I’m tired from being on the road but have an anxious curiosity around what’s in store for me. This is a conference for a community that I’m not as familiar with, WordPress. I’ve been in Drupal for over 9 years so that feels like home, like family, but WordPress I’m still the “new guy”. The outsider. On top of this, the conference was billed as a conference like none other. Yeah I’ve heard that before, and most the time they’re similar. That’s not to say I don’t enjoy going to conferences, I’m the strange type of person who’s batteries are charged from it, it’s just that I’ve yet to go to a conference that’s really shocked me.

By the time we reach the hotel, I’ve already had an in depth conversation around my company, Lockr, and what we do and learned about content marketing in a way that I hadn’t looked at before. That was just in a 30 minute van ride! The van turns into the resort and I’m blown away. It stops, we hop out and are greeted by one of the most beautiful lobbies I’ve ever seen in the world (and I’ve seen a LOT of lobbies). While waiting for our room we’re greeted with a welcome drink. Good I think, a little liquid courage to help subside the awkward feeling of knowing only a handful of people.

We get to the room, overlooking the water, and then head up to the lobby to grab another drink ( I think you’re seeing a pattern by now, it’s all-inclusive). As people start to filter in, they’re all greeted like long lost friends and one by one they grab a drink and head to the veranda overlooking the water. Once we’re all there, Chris Lema shows up to officially kick off the conference.

I’ll pause here and introduce you to Chris. He’s one of the most genuine people I’ve met who instantly can become friends with anyone he meets. And he’s well known, one of the most respected people in the WordPress community, but he doesn’t show it. You can get from just a few conversations with him that the reason he’s so well respected is because he’s always quick with a great story that drives a point that makes you pause and think for a bit. That and he’s always joking with those around him. This guy just genuinely has fun around people and sharing his wisdom from years in the business.

So there we are, on the veranda overlooking the ocean and Chris welcomes everyone by saying “Welcome to the conference that will ruin every other conference for you.” Bold statement. Little did I know how true it’d be. You see, everyone at that conference is hand picked by Chris to bring a diverse background. There’s people running some of the largest and most successful products in WordPress, there’s agency owners, and there’s people like me who are just getting started on their journey in products and WordPress. The group is small, under 40, and all business owners, founders, builders, entrepreneurs. It’s purposefully small so to create intimate interactions with everyone. After a short welcome and a walk through the conference and little rules (don’t be a bad person) we head out to dinner with our conversation prompts.

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That’s the thing about this conference you learn quickly: everything is scripted and honed to create conversations. Every person selected, roommates assigned, lunch groups assigned, and topic leaders are all there for one thing: to create deep and meaningful conversations that will challenge you to think about your business in different ways.

We had a wonderful meal, and I got to know some wonderful new people. Afterwards we head down to the patio, wrangle up a bunch of tables and start the infamous: CigarPress. More on this later but needless to say this conference is a mix of Chris’ two favorite things in life, his friends/colleagues, relaxing surroundings, and cigars. If you didn’t start the week a fan of cigars, you likely left it as one. No problem for me, I’ve already found a love for a good cigar and brought a few of my own.

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The next day we wake up and head off to our “sessions”. I put sessions in quotes because this isn’t like any other conference you go to: The sessions are in the pools! We all hop in and begin. Reason number 1 this conference ruins all others, how often do you have a session in a pool overlooking the Mexican coast? Additionally, these sessions are unlike most you go to at a conference because they’re meant to be more of a conversation than a lesson. The session leader talks briefly about their topic to lay the groundwork of what they’re discussing then begin answering questions, asking questions, and quickly the conversation gets deep. We’re all given a chance to talk and ask questions of the leader but also of each other. You quickly realize again that this is scripted and these leaders are some of the top in the world in their topic. Ranging from product building, book writing, Facebook marketing, SaaS pricing etc. it’s all there in the discussions in the pool throughout the 3 days of sessions.

There are 2 sessions at a time, and 2 time slots in the morning. That’s it. After that you grab lunch at one of the 5 star restaurants at the resort with your lunch group to debrief what you learned in the morning (again carefully picked by Chris to provide good conversation).

After lunch though is, to me, the most meaningful part of each day (besides cigars at night). Afternoons are free. You can do whatever, wherever you want (again don’t be a bad person). This is where the magic happens. By getting some of the greatest minds together, in a place that’s remote and away from the busy pace of life, unlimited drinks, sun and pools you spend your afternoons meeting people from all walks of life and business, all there with one purpose: to have meaningful conversations about their business (and yours). Each day was a different location for me, with a different group of people but we talked about everything from life and family to the struggles of owning a business, our product/service and what our plans/goals are for the future. These aren’t light topics, and that’s one thing you quickly learn that makes this conference different. Everyone there is intentional. There’s no awkward small talk about weather, sports, or the latest code release. You just cut the bullshit and get straight to the questions that mean most.

For some this can be daunting. They want to keep a facade up or don’t want to get into the dirty details of their business. I’ll admit, at first I was one of them. But over the week you learn the more you let your guard down, the more you learn from and impact each other. By the final night we were sharing stories, feelings, ideas and challenges that many of us had held back for a long time. Through it we found an even deeper support from the group.

So by the time I got on the plane to leave 4 days later, I was physically recharged, mentally exhausted from all the deep and meaningful conversations, and ready to go implement what I had learned. Plus, I had a group of new people I can call friends, who I look forward to meeting up with each chance I get.

Some look at a week-long conference in Cabo as an excuse to get some sun on the company dime, but CaboPress is anything BUT that. It’s a mastermind conference where you’ll meet some of the smartest, most talented people in their field, and do it in a way that fosters deep and meaningful relationships that last. Past attendees of CaboPress have gone on to create joint ventures, acquisitions, and many other great growth opportunities for their business. It’s a conference I’ll drop everything to go to again, and one that’s worth your time if you’re willing to put yourself out there.

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Oh and for those wondering what the longer story on CigarPress is… I enjoyed many a fine cigars while down in Cabo. I came into the week with a small lingering cough that I had caught from my young children two weeks prior. Well it seems that cigars and coughs don’t mix well and the cough got worse and worse as the week went on. By the last day I was coming down with what doctors later thought was Bronchitis and the flight home I started to get all the other lovely symptoms that join it (fever and body aches). So Saturday morning I went to my doctor and they prescribed me some lovely antibiotics which I thought would help. The next day I awake to hives/rash all over my body and by the time I got back to the doctor’s I had spiked a 103.7 fever and my resting heart rate was up to 120 bpm. Needless to say I found out my first drug allergy and it was a good one. I spent the bulk of that day in the ER getting my body back under control so it didn’t start killing off my organs and spent the next 5 days in the various stages of severe allergic recovery. Luckily the high fever killed off all the bacteria that was in my system causing the cough, so I guess I had that going for me. Does this mean I’ll skip the cigars next time? No way! Just means I know what antibiotic I WON’T be taking if I ever get sick again.