CaboPress, Chris Lema, and feeling like a pirate

Scott Magdalein
Nov 18, 2016 · 4 min read

There are tech conferences, entrepreneur conferences, and WordPress conferences…

and then there’s CaboPress by Chris Lema.

In the world of WordPress, CaboPress is like the Bilderberg Conference and Chris Lema is its Shadow Government chairman. Thankfully, neither Chris nor CaboPress are aiming to secure gold mining and oil drilling rights in rainforests. Their motives are far nobler.

Chris Lema is special.

Few people have more quiet influence over the trajectory of WordPress and its sprawling community than Lema. He’s an omnipresent advisor to some of the biggest names and businesses in WPLand, and rightfully so.

Lema is the embodiment of strong opinions loosely held. He speaks with passion about almost everything, but this week I saw him listen with genuine openness to opposing views.

He’s a connector; the person who knows the person you should know and is willing to introduce you with a generous prologue. He’s not stingy with his friendships.

CaboPress is Chris Lema.

It’s full of opinions backed by experience, but without the pretentiousness of unwavering certainty. It’s hot tubs and cigars and meandering conversations that leave your mind full and your heart hopeful.

But to be clear, CaboPress isn’t only Chris Lema. In fact, Lema’s voice was one small input among dozens of sharp-minded, and sometimes sharp-tongued, entrepreneurs.

The hosts are incredible. These are the people who’d only speak for outrageous fees on very large stages if it weren’t for their relationship with Lema. [Side note: At CaboPress, hosts are the equivalent of traditional conferences keynote speakers.]

At what other conference would I be able to talk personally, at length, with the founder of WPEngine and the founder of Copyblogger/Rainmaker, not to mention the founders of a dozen other successful startups and agencies in the WordPress world? It just doesn’t happen.

I feel like a pirate after CaboPress.

I landed in this tropical place, hot and sandy with giant lizards and friendly locals, only to go home with a treasure chest full of invaluables. And that feeling isn’t just the lingering sensation of rolling on Pacific swells in a pirate ship, which is also an experience that only CaboPress could provide.

There’s always that standard followup question from each conference I invest time to attend: What did you get out of it? It’s a big list; bigger than I expected and certainly bigger than any post-conference list of takeaways I’ve ever had.

Charge more. Automate more. Pursue recurring revenue. Don’t neglect services that support products. Diversify your emotional life. Work-life balance is a myth, but worth trying for. Other successful entrepreneurs feel just as anxious as me and that anxiety isn’t fixed by higher revenue. One niche is nice; multiple niches are better. WordPress doesn’t have to be synonymous with cheap. I’ve been doing content marketing all wrong. SEO is a discipline more than a skill. I don’t need to raise money…probably ever.

Of course there’s the trappings of CaboPress that, alone, are worth the trip. I got to dip my feet in the Pacific Ocean while I fed a school of amber jacks and trigger fish.

I woke up to the sound of humpback whales launching their multi-ton bodies into the air right off the beach. I spent a minimum of 3 hours per day literally sitting in a pool with friends talking about our shared passions.

I ate a brilliant filet mignon at Ruth’s Chris and too many fish tacos to count while sitting beachside. I ordered cheesecake from room service.

I rode on a pirate ship and watched acrobats swing from the riggings while break dancers entertained on deck. I saw seals eating out of the hands of fishermen and a big freaking lizard.

So yeah, CaboPress was amazing on many levels.

CaboPress in photos.

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