The Strategy Behind CaboPress

I’m often asked about the strategy behind the event – the why behind each of the dynamics and decisions that go into planning CaboPress. Here are the ten factors that make it special.

First, decide how you’d like people to feel as they leave.

Most conferences spend a lot of time trying to fill up all the space and time with stuff to do. The assumption is that if people do a lot, they’ll likely find something they enjoyed, or something that was helpful. Or maybe it’s that they’ll think it was worth the cost.

My sense is that the focus should always be on the feeling people are left with. If they regret that they didn’t get enough time to connect, that’s not good. I they feel overwhelmed with too many different ideas that they can’t implement, again it’s no good.

I wanted to design a conference that would have people leaving feeling relaxed and refreshed while also being energized.

Second, curate every participant.

I know this won’t work for a lot of larger conferences. But all it takes is one speaker, one organizer or one guest to ruin someone else’s experience.

I can’t tell you the number of vacations (not even conferences) where an entitled jerk has left me frustrated and distracted.

I remember having a dinner with a bunch of different entrepreneurs a few years ago where one of them talked about an event they used to run where they vetted every single guest, speaker, or entertainer.

For me, that’s been my goal every year. To be super diligent about every single person participating. That has meant rejecting some people. It has meant personally inviting some people to apply.

It has meant days and weeks reviewing applications and paying attention to percentages. Percentages of alumni returning, percentages of service or product companies attending, percentages of men and women attending and more.

Third, limit the new ideas without limiting practical advice.

I don’t know about you, but I’ve been to tons of events that have 2 or 3 tracks, across 2 or 3 days, with 6 to 8 sessions daily. That’s 24 new ideas, at a minimum. And at the end, all I have is high level concepts, little practical advice that pertains to my unique situation, and so many ideas that leave me frozen in fear rather than energized with excitement.

That’s why I limit our sessions to 3 hours a day – giving people tons of time for rest, for follow up, and to engage in the lower-level and more detailed conversations about application. It’s what I call the 4:9 ratio (four hours of content to 9 hours of rest) and I’ll explain the fourth hour in a second.

Fourth, hold it far away from our every day grind.

I know tons of conference planners that spend gobs of money on wifi. And while it’s great for social media, it’s also terribly distracting and can result in people doing work while at the event.

The resort I chose is one I love. It’s also more of a destination location for vacations than for work. And the wifi has been spotty some years. Basically, it’s perfect as a place to step away completely from the hustle of the work, and spend some time reflecting on the work instead.

Fifth, skip lectures and embrace discussions.

Prepared remarks can’t always handle the light of day. You know what I’m talking about, right? A speaker declares something like, “Stop trading hours for dollars,” and you want to ask them why they think the entire legal industry hasn’t fallen over. But it’s a lecture, not a discussion. So off they go on their monologue and you’re still left with questions and challenges.

Discussions are messy. They’re not perfect. But they benefit from multiple participants. And the truth is, you don’t know if the perfect answer you need will come from the moderator or the person standing next to you. But you’ll have better odds of getting answers with every additional person who is participating in the discussion.

It’s why we don’t have speakers. We have discussion hosts. And I use the word host on purpose because I want them to think of their roles as being hospitable to every thread in the discussion, not just their own expert opinions.

Sixth, eliminate logistics and financial interactions.

Have you ever been at a conference or event where you have to find a place to eat. Or deal with the fact that all the close places are super expensive? Or that your credit card isn’t working because you’re out of town?

People pay for CaboPress before they arrive. They buy their own flights long before they get on them. From that point until they’re leaving, there is very little to think about – from a logistics or financial perspective. Holding an event at an all-inclusive resort helps. Especially one with tons of options for food.

Seventh, force engagement.

If you’ve ever gone to a conference with a few other folks you know, you know how easy it is to stick with them the whole time. But that’s not how you’ll get the most out of anything.

So when I was designing the conference, I decided to force lunch groups that were consistent daily. A kind-of small group. And it meant people could debrief regularly with the same folks. Or could dig into specifics with them. It’s the fourth hour of the day I mentioned before. Only this time, the fourth is with the same folks every day.

I also set things up so dinner groups change nightly. Again the goal is to create interactions and engagement that some people wouldn’t choose on their own.

But if you do that, be sure to consider giving them a conversational prompt so they have something to talk about initially as they get to know each other.

Eighth, price it strategically.

A lot of conferences are trying to move their prices down so that more people can attend. Unfortunately, more people doesn’t always make an event better.

I’ve found that pushing the price up slowly each year has helped us keep the event smaller.

It also has the ancillary benefit of ensuring that people see the event in a different light. If I pay $99 for an event, it’s easy for me to cancel my trip and not stress over it. That’s harder to do when I’ve paid much more.

Ninth, keep it small. 

Small is relative. For some people a 200 person event is small. For others a 20 person event is small.

When I thought about it, and the reason we went down from 70 to 45, I was doing the math on how many interactions are required for each person to meet with every other person.

As you likely know – with every person you add, the connections grow exponentially.

But keeping it small and ensures that the people you curated get the most from the others you curated. To me, that’s the winning formula.

Lastly, 9 hours of rest is magical.

Some people need naps. Not everyone is an extrovert. Not everyone thrives in groups.

Creating 9 hours of free time for the four hours of highly engaged time allows people to self-select how they want to use it – from one-on-one meetings to group hangouts to play time in the pool (that also becomes a place for more Q & A).

So those are the ten guiding principles that led me to create an event where discussions are held in the pool each morning, where there are lunch groups, where there is five or more hours of free time daily, all held at a five-star, all-inclusive resort in Cabo San Lucas.