• Drew

Get out of your bubble...

Updated: Oct 9, 2019

“What are the fitness people doing at a WordPress conference?”


I am pretty sure that is what the 50+ attendees were thinking when we first arrived at the 6th Annual CaboPress Conference. Heck if I am being completely transparent - It's what we were thinking too!! When the entire group gathered for the first time on Monday night, you could practically hear the song from Sesame Street playing in the back ground. You remember….“One of these things is not like the other”.


A small part of the CaboPress Crew

CaboPress is the preeminent Mastermind style conference in the WordPress industry. Business owners of all types involved in the WordPress space apply to attend and are then hand selected by the host. Once selected, they all travel to Cabo San Lucas for four days of mentally intensive sessions…..in a very physically relaxing environment. It is the ideal situation for entrepreneurs to mix with like-minded peers to brainstorm the next innovation, integration and/or inspiration. * Problems were identified and owned.

* Solutions were suggested and thought through.

* Partnerships were formed and strategic alliances were started.

All in two formal sessions a day, (which were conducted pool side), an organized lunch, a rotating dinner and some of the most interesting afternoon ‘free time’ discussions I have heard at any conference I have either attended or presented at. Again, all in the comfort of a pool.


Drew fully involved in the 'Hero's Journey' session

Hundreds of entrepreneurs apply every year – this year there were a total of 55 attendees……including ‘two fitness people’....which really does beg the question…….why were Joy & I there at all?


Easy Answer – The Host wanted us there:

CaboPress is presented every year by Chris Lema, a major figure in the WordPress community and someone we are lucky enough to call friend. Over the last several years we have been a small part of his 100+ lbs weight loss journey (check out the before/after he posted a few months back below) and the simple answer to the question is he wanted us there to provide attendees and their guests the opportunity to also focus on their health and fitness with morning workouts.


Day 1 Work Out Crew!!


But anyone who knows Chris knows he is far from simple.


Harder Answer – He wanted people out of their Bubble

We all live in a cocoon of our own making. We associate with the same people day in and day out. We go to the office with same coworkers. We get on Zoom Meetings with the same associates. Attend a small group with folks from the same church. Play golf with your kid’s friend’s parents. Even social media platforms leverage algorithms to make sure you see all the posts from within your bubble. Whether we want to admit it or not – we are all in a bubble.


I think Chris wanted us there to expand people’s bubbles not to mention burst our own.

  • We presented on the impact fitness has on mindset.

  • We shared how we put family first while building a business together.

  • We shared how our kids are involved in our business and now our partners.

  • We challenged people to be better with their time prioritization.

  • Oh – and the analytics guy in me could not keep his mouth closed about how data should be used prescriptively vs. just writing history lessons.

And I don’t think any of that was expected from ‘the fitness people’ but Chris knew what to expect and how to burst the bubble to get us all thinking differently.


I would be remiss though if I let you believe this was all one-sided. Joy and I left challenged to rethink and retool several of our business strategies and processes. We are going to take a really hard look at the customer journey, every element of our marketing and communication is going to be run through a different filter and don’t even get me started on the mind stretch the ‘Experimentation’ session put me through.


It has also made me realize that we all need to acknowledge our bubble and then actively seek experiences outside of it.


#CaboPress Founder Chris Lema

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