Ali Jafarian
Ali Jafarian

Last week I spent 4 days at CaboPress – the best business conference in Cabo San Lucas, Mexico. This is a blog post to encapsulate the experience and reflect on the 4-day journey.

It’s also been months since I’ve put time into writing, so what an apropos opportunity to share new thoughts!


CaboPress 2019 was a small group conference of 40 entrepreneurs from various backgrounds. We had everyone from first-time founders and POCs (proof of concepts) to multi-million dollar businesses and seasoned leaders. This small group environment is designed to help you go deep on specific topics and share ideas/learnings in a collaborative spirit.

That said, CaboPress is unique from other small group conferences in several ways.

The Venue

For starters, it’s hosted on a 5-star resort with all-inclusive access during the entire stay. The all-inclusive experience is attractive for obvious reasons of being pampered and over indulging in food/drink. But more importantly, it allows you to relax and focus on the conference experience instead of making micro decisions on where to eat, how much things cost, what package to choose, etc. when traveling.

As an entrepreneur, I really appreciate this. The potential cost savings aren’t nearly as important as the convenience and time savings of all-inclusive. So thank you Chris for making that easy.

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Until next time, #CaboPress!

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The Format

Let’s just say this isn’t your typical business conference schedule. Each day followed a guided structure from morning through dinner. Here’s the breakdown –


Work sessions were done in the pool every morning. Each session is led by a chosen “host” attendee with a chosen topic. After the host talks for 15-30 minutes the session is opened up to Q&A style discussion. Anyone can ask anything, and anyone can answer anything. This results in awesome insights that bubble up naturally (no pun intended).

Personally, I’ve never done much business in a pool! To that affect, I found it really refereshing to waid water while listening to business discussions. The only major challenge was balancing time in the direct Mexican sunlight! That baby burns quickly if you sit in one spot for too long.


Each person was assigned to a lunch group of 4-6 people, which Chris hand selected. Immediately after the morning session, you break out and eat lunch with this group. The goal of lunch is to identify relational ways to create value for each other. In other words, Chris put us in these groups intentionally because he wants us to uncover specific things related to each others’ businesses.

These lunch groups were really helpful for me because our lunch mates came from very different backgrounds/businesses. We got to learn from Brad and Pete of Delicious Brains, who are building WordPress plugins and new SAAS products. And then we got to learn from James of Automattic, who’s completely rebuilding the Jetpack brand and product offering. The conversation was diversified to say the least.

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Soaking up #CaboPress with some rockstars 👍

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After lunch you have a few hours to use time as you wish. Most of us would sync up in one of the large pools or grab some beach time under a cabana. What’s cool is that many people were not working during these “open” hours. Instead, we found ways to connect and continue discussions fueled by business or life.

I took this time to learn more about peoples’ backgrounds and families. Business usually ended up somewhere in the conversation, but I really enjoyed trading stories around kids and homelife as much as possible. There were many parents in the group, which is always a plus [and preferred bias] for me.


At 5:45 we all meet in the lobby bar for dinner. Chris would give us a quick 15-minute recap and then instruct us on how to break for dinner groups. These groups were also 4-6 people with a certain criteria of who to eat with. Each night presented a new criteria of group matching so you avoid eating with the same people every night. There was also a general question to ask during dinner, which Chris provided.

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Daily Roundup!!! #cabopress

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The question of the night often inspired engaging business discussion, which ultimately led to other avenues of each group member’s story. The dinner setting was a great opportunity to go deep on various topics in an organic way.

After dinner we were able to retire or hang with the majority of folks in after party fashion. However, this is not a get sloppy drunk style after party, but rather a casual gathering with cigar and/or cocktail in hand. In my case, a Joey CaboPress inspired chocolate milk was the weapon of choice 😉

We followed this format Tuesday through Thursday. Three solid days was the perfect amount of time to connect with most people there and not get burnt out.

The Experience

As you can imagine, being in Cabo on a 5-star resort is an experience in itself. It rivals some of the best known beaches on the planet. But that’s not what made the CaboPress experience awesome for me. I’ve been to Thailand and Costa Rica, who both rival Cabo in terms of superior beach experiences.

The real value behind this conference experience is the people.

As I mentioned, we had a varied group of starters to doers. Some folks were conceiving new ideas and establishing early stage growth, whereas others had previous acquisitions under their belts. Some folks were single and still in the 60 hour/week grind, while others had multiple children and travel the world freely as they work. Most people had a unique story with unique skills.

This opportunity to interact with such a unique group is truly priceless. You do not find this at typical business conferences. Chris could probably double the cost next year and I’ll register just as fast (but don’t do that, Chris!).

Now the bad news around this experience…

It will be hard to beat the CaboPress experience! So now I’ll have to anxiously await next year’s invite.

The Host

I saved the host for last because, for me, it was the most impressive part of the conference. And I’m not just saying that to score brownie points with Chris. In fact, I had never even met Chris until this conference. So I’m sharing this in an un-biased manner as someone who doesn’t know him well.

For those of you who don’t know Chris, he’s one of the biggest influencers and thought leaders in the WordPress space. He’s also head of product at Liquid Web and an entrepreneur with many previous success stories. Simply put, he’s quite accomplished in business.

But most importantly, Chris is an amazing human. Here’s why –

I’ve been fortunate to meet lots of humans in my lifetime, and lots of people with success in business. Everyone in business has their own approach and strategies. A lot of people in business also end up having some kind of agenda.

Chris is hands down one of the most strategic thinkers I’ve ever met.

If you haven’t noticed by now, the entire conference was architected with underlying strategy, some of which you don’t even realize until a future “ah-hah” moment. From the session settings, to the lunch groups, to the dinner requirements, EVERYTHING had intentional strategy involved. Literally everything.

And the agenda from Chris’s side is quite simple – how can all these people help each other.

I’m sure Chris could do other things with his time… lots of other things. But he chose to be thoughtful and gracious in bringing this group together. If you know anything about nothing, you know that people do amazing things on this Earth together.

That’s what made CaboPress so special and unique from other conferences I’ve been to. That’s why I took the time to write this blog post. And that’s why I’ll jump at the chance to come back if given the opportunity.

The Takeaway(s)

To put icing on the cake, I also left with some new ideas and validation against some of the business challenges I’m currently facing. My business partner (John), and I, left with answers to key questions around the Credo platform we’re growing. We also left with new relationships and potential partnerships for the business.

A few very specific things I retained as well, which I’ll be applying immediately:
  • Use real-time experiments to validate some of your assumptions, especially things you know you can deliver on. And in doing so, realize that most experiments fail. That’s actually why they’re so valuable. They allow you to learn quickly.
  • It will be very hard to sell your business [at some point] if you’re not completely replaceable. I already knew this, but CaboPress really forced me to think about putting better systems in place across my businesses.
  • Take time to transition out of work each day before jumping back into family mode. This really hit home for me because I’ve been guilty of bringing work into family life in the past.

And of course, it “pays” to get out more and meet new people!

So in summary – CaboPress was a real treat. If you’re looking for a unique setting with amazing people and invaluable content, you should probably figure out how to get on the 2020 CaboPress list.

Ali Jafarian

Ali is a father, husband and serial entrepreneur with a deep drive to create. He writes, records, codes and builds things to inspire the artist in all of us.

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