Five Years of CaboPress

I’m currently in Cabo San Lucas running the conference that I dreamed of six years ago and began running five years ago. I’ve written previously about how I designed this conference to be unique.

Tonight, after the first full day of sessions, I’m delighted by what I’ve seen and experienced. And as I reflect, the success of this conference / retreat over the years has come from decisions that are worth calling out.

Smaller is better than bigger

When everyone is evaluating what it means to be “successful,” we often talk about size: revenue, customers, staff, etc. But the laws of impact can sometimes be inversely proportional to big numbers.

A single connection, a single conversation, a single action taken, can have an incredible impact. But it needs space to breathe, space to germinate.

CaboPress has always been smaller than most conference. But the last two years it had grown to 50-60 attendees. This year it is 30.

And smaller is better. It ensures that people are both seen and heard. And already I’m seeing the results of these connections.

Different people connect differently

Big discussions are great for some people. But others may be intimidated in a group of 10-15 people. Small groups of 4-5 that meet daily helps even the most introverted people build enough trust to share and ask deeper questions.

While half the days are structured, the other half is wide open and that’s where is see the most conversations happen. They may start with family life or movies that make you cry, but end in talks about what Code Brown means at Amazon.

What matters most is that people are making connections and developing trust. And trust is the factor that drives relationships deeper and opens the doors for partnerships, client relationships, joint ventures, job offers and more.

Curation matters most

Over the last four years we’ve had 150 people attend. Yet every time we hold the conference, I keep the alumni down to less than 50%.

This year that meant I had 15 spots for people that had been here before. That meant not having 135 alumni attend.

Every year it gets harder. But it’s what keeps the conference powerful and useful. New attendees don’t feel like they’re intruding.

I tell every new class of CaboPress attendees (including Year Five) that each one belongs here – that each one has been selected, and that this is a highly curated group of folks.

It’s not only true but it helps everyone act with purpose. They don’t know what they’re supposed to get from the event but they know they need to look for it.

This isn’t just a vacation in Cabo. People can do that on their own without me. The folks that come are fully present and engaged – and that always makes the conference a success.

The discussions are equally curated

It’s my conference. So it’s no surprise that I pick the topics and the hosts who facilitate the discussions.

But I don’t pick what’s popular. In fact, attendees don’t even know the session topics when they sign up. They have to trust that I know what I’m doing.

And I don’t pick topics based on their requests. They don’t have a way to make those requests.

No, instead, I invite them to attend sessions based on what I believe they need, even if they’ve never thought they’ve needed it.

And the results after today’s sessions were the same as every other year – people weren’t ready for all that they received and were delighted.

CaboPress is about business

This year I invited some people who don’t identify as being deep in the WordPress ecosystem. And it’s worked as I hoped it would.

The conference never was technical in nature or focused on WordPress as a technology. It had been focused on that market because it allowed me to shape the discussions in ways I knew well.

But business is business. Pricing, marketing, content, customer service, getting advice, team leadership – none of these things are specific to WordPress.

Digital agencies and SaaS companies all face similar challenges as some of our largest WordPress companies.

I’m glad for this as the next five years may see even more transition into embracing companies outside of WordPress, even if I don’t change the name.

I’m trying to ruin conferences for people

Lastly, and I say this with love for a lot of others events, I’m still trying to create an event that ruins attendees for all the other conferences held in ballrooms and convention centers.

Three hours of content each day. Two sessions max each day. Unlimited food and drink each day. Deep conversations and time to reflect each day.

There’s no other way I’d want to do this.

Want more leadership tips?

Subscribe to get my latest notes by email.

I won't send you spam. Unsubscribe at any time. Powered by ConvertKit