CaboPress 2018

The view from just outside my room at CaboPress 2018

It was the last night in Cabo. There I was, sitting on the patio after dinner, breathing in cigar smoke, listening to snippets of a conversation, then jumping into another, laughing hard with the group as we shared stories, enjoying drinks, and just taking it all in. It felt surreal and perfect. It was clear that we’d all had an incredible experience.

I had added my name to the CaboPress waiting list just the week before. It turns out I had stumbled into perfect timing. Chris Lema sent me an email – there had just been a cancellation and he had an extra room. He invited me to join and I booked my flights. I’d heard good things from former attendees, but I didn’t really know what to expect. I’ve never been to Mexico and the idea of sessions held in a pool was intriguing, but it seemed like it could also be terrible.

It was perfect.

Reflecting back on the past few days, a few highlights stand out to me.

A great host makes a big difference

13 years in WordPress and this was actually my first time meeting Chris. I’d heard good things and had positive expectations, but I didn’t know what to actually expect. I’m a bit of an introvert and being in a new environment where I don’t know folks well is a stressor.

On Monday evening, Chris called us together in the lobby to welcome us. As we pressed in to the group, I fought with my fears.. “Wow, I don’t know most of these people.. Do I really belong here? Do I have anything to offer?” After a few moments of light introductions, Chris cut right to the chase. He encouraged us clearly and directly – “You all belong here.” He reminded us that we each have much to offer and that we’re all here to learn and grow together.

I felt comfortable again and as Chris explained how the next few days would play out my fears transformed into excitement.

A great host makes a big difference. Chris Lema is a great host.

The benefits of “different”

Chris designed CaboPress to be inherently different. On Tuesday morning, we kicked off the first session on “High Value Courses”. By itself, it would have been a great session. Jennifer Bourne set the stage and then lead us into a focused discussion covering a range of strategies and tactics for thinking about and offering high value courses to our customers.

But having that session in a pool, introduced an entirely new dynamic. With no laptops, no presentation, and each of us in our swimming suits with various degrees of sunscreen applied, it was clear to our brains that this was different.

The environment made it hard to not be relaxed and engaged. As a result, I found the sessions more memorable and more impactful. When I think back on Allison’s session on writing a book or Brennan’s session on personalization, I have a whole additional range of senses and context that deepen the message’s resonance.

In a world with increasingly strong pulls at our time and attention, it was great to go to event that required less time (only two sessions a day) and gave more because it chose to be different.

The benefits of giving

Chris had set the stage for us on the opening night. He reminded us that we were each invited because we have something of unique value to give. Our hosts, each extraordinary and remarkable in their own right, were there to lead discussions, not lecture. Accordingly, we would each get out of the sessions what we put in.

I took the message to heart and focused my energies on leaning in, on listening, and on looking for ways that I could contribute my own experience and expertise.

As I did so, I discovered new questions to ask myself and began seeing the answers to questions I didn’t know I’d been asking. There is incredible inherent benefit to giving and the context and environment of CaboPress provides rich opportunity to do so.

What I received

On a personal level, I made new friends. Over lunches, dinners, and pool side chats, I got to know new people and deepen my context / relationship with folks I’d already known. Life is so much better with friends and I look forward to growing friendships with the folks I met in the months and years to come.

On a professional level, over the sessions and through personal and group conversations I developed a broader perspective, a deeper context, and a richer appreciation for the diversity of our open web ecosystem. I love WordPress even more : ).

I look forward to developing partnerships and creating new opportunities around the values we’ve identified individually and collectively.


CaboPress 2018 was excellent. Chris has created an extraordinary experience that will stick with me for years to come. If I get the privilege of being invited back I look forward to returning and if I don’t (Chris tries to keep alumni to less than 50%) I look forward to hearing the experiences of the new folks!

Jonathan Wold

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Jonathan lives and works in beautiful Coeur d'Alene, Idaho.