CaboPress 2018 – The Remix

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I spent the primary week of October 2018 in Cabo San Lucas this 12 months. This was once my 2d 12 months attending Chris Lema’s CaboPress, a mastermind-conference-retreat held at Chris’s favourite lodge in Cabo.

Right here’s are some footage from my Instagram feed:

Over the 5 days we had been there, my enterprise as soon as once more modified simply adore it did in 2017.

I’m going to speak thru what precisely was once so impactful, and why I really like small meetings like those.

A snappy assessment of CaboPress

To position it succinctly, CaboPress is per week within the fall the place a bunch of marketers and founders, handpicked via Chris Lema, accumulate in Cabo San Lucas at a 5 big name all inclusive lodge, the Grand Fiesta Americana Los Cabos. Tuesday thru Thursday there are 2 periods in step with day in a lodge pool, every led via a “host” invited via Chris.

This 12 months the hosts had been other people like Jennifer Bourn of Bourn Ingenious, Brennan Dunn of RightMessage, Allison Fallon, Tony Perez of Sucuri/GoDaddy, and extra main periods on productized services and products, personalization, e book writing, management, worry, and extra. They’re no longer actually talks, however reasonably facilitated conversations led via any person with deep revel in there.

(Supply: Jennifer Bourn)

The remainder of the day till dinner is loose, and other people both atone for some paintings or chill out. I attempted to do much less paintings this 12 months within the afternoons than ultimate, however nonetheless were given caught in my room a pair afternoons. Thursday afternoon I disregarded my inbox and went to search out other people placing out in a pool, and identical to ultimate 12 months had some enterprise and existence converting conversations (thank you Ken).

In 2017 there have been about 50 attendees to CaboPress. This 12 months there have been 30, about part alumni (like myself) and part new. This introduced, individually, a really perfect dynamic and was once additionally sufficiently small that you might want to hook up with everybody. I hooked up with some guys who had been there in 2017 however I didn’t get to talk with in any respect ultimate 12 months. I’m happy I were given to understand them in 2018!

Twelve months later

Ultimate 12 months, I wrote a recap of my 2017 revel in that defined the spaces I noticed in my enterprise on the time, specifically that:

  1. Credo had turn out to be a services and products, no longer a product, corporate;
  2. Ask questions as a substitute of turning into defensive;
  3. Encompass your self with just right other people;
  4. Be engaged the place you’re;
  5. Don’t fail to remember to have amusing.

This 12 months, I re-realized probably the most identical issues I realized ultimate 12 months and realized some new issues as smartly.

I additionally discovered, upon mirrored image, that I if truth be told did observe the teachings I realized ultimate 12 months broader this 12 months.

Ask questions and “why”

This has been a large theme of my existence for the ultimate 12 months, and it began at CaboPress.

I’ve all the time been a skeptical particular person. As an alternative of seeing one thing this is running for any person and asking why, I’ve tended to roll my eyes at it. This has been to my detriment, and beginning ultimate 12 months at CaboPress I started digging deeper into why one thing is operating or why any person has an target audience.

As an alternative of pondering I’m all the time proper, I’ve been in quest of to be told from others. And it’s been superb for me in my opinion and for my enterprise, and I consider units us up higher for the long run.

Encompass your self with just right other people

In 2017 at CaboPress I changed into painfully conscious that I had to be round just right sensible other people extra steadily. This translated into slightly a couple of journeys this previous 12 months as a way to be round nice other people – San Diego in February, San Francisco in September, Cabo in October, to call a couple of.

(Supply: Jennifer Bourn)

CaboPress 2018 was once higher for me than ultimate 12 months as a result of there have been already other people there that I knew from each 2017 and from puts like MicroConf. As a result of we already had just a little of courting established, lets pass deeper than sooner than.

I were given to be in a lunch crew with Phil and Cori Derksen of WP Easy Pay who I met in Cabo ultimate 12 months. I were given to hang around and smoke cigars and discuss existence and enterprise and snort with my good friend Joe Casabona who’s a developer, path writer, and writer of How I Constructed It which I were given to be a visitor in this 12 months. I additionally were given to hang around with the Beaver Builder guys and communicate technique, and realized much more about running and automating an company from Jen Bourn as a continuation from ultimate 12 months It really was once a good looking crew of alumni.

And I met a ton of recent other people. From nice conversations with my roommate Sam Brodie to business-redefining dialog with Ken Wallace, and alongside the way in which placing out with more than a few WordPress carrier enterprise operators who’re at more than a few phases of enlargement and suffering thru identical issues as me.

The folks at CaboPress are as top-notch as I’ve ever present in one location, and that could be a testomony to how CaboPress is about up.

Be engaged the place you’re

Ultimate 12 months at CaboPress 2017 I discovered myself in my room from time to time wanting to do paintings, when what I actually sought after to do was once be out placing out with other people. As soon as I used to be ready to break out from my laptop, I used to be reminded that as a way to revel in one thing to the fullest you want to be absolutely provide there.

My spouse and I are living in Colorado in order that we will be able to be outdoor up to imaginable. We backcountry ski, she runs, I mountain motorbike. And we like to head backpacking. We actually have a custom of going backpacking over the 4th of July weekend, and in 2018 we spent 2 days virtually utterly about 12,000 toes of elevation. It was once superb.

And we had been absolutely provide there. No telephone reception, no pinging alarms. Actually, our telephones ran out of battery and it was once superb.

This previous 12 months I’ve made an effort to be as provide as I will the place I’m. We moved to Denver in past due 2016 and it’s the place we plan to stick, so I’ve made an effort to be provide right here via going to get beers with pals, enticing in the local people, or even just lately were given an administrative center out of doors of the home.

CaboPress 2017 taught me that, and 2018 bolstered it.

Don’t fail to remember to have amusing

Above all, existence isn’t supposed to be a slog. We every so often assume it’s, however actually should you’re no longer having (a large number of) amusing then one thing is VERY off.

We must have a great time and be capable to sit back some even whilst we’re rising companies and being execs. Once in a while longer weeks are vital, however we additionally wish to take steps again someday to get a broader view on enterprise and existence.

At CaboPress, this implies placing out within the pool with a drink to your hand and going deep with other people. Like in 2017, at CaboPress 2018 I had probably the most best possible and maximum impactful conversations of the entire time whilst placing out within the pool with a lager in my hand.

And it was once depraved amusing.

2018’s CaboPress classes

This 12 months at CaboPress, I realized some new issues that had me come away refreshed, excited, and filled with ideas. Actually, at the flight from Cabo to Dallas (layover) I had an Go out Row in particular in order that I may just write down my ideas from the week. five,000 phrases later…

High quality > amount

CaboPress 2017 was once about 60 other people. CaboPress 2018 was once 30, with part new attendees and part alumni. There have been other people at 2017 who I didn’t talk with, however I were given to understand this 12 months and I’m a little bit bit unhappy I didn’t meet them in 2017 as a result of they’re superb other people.

I’ve all the time prioritized having a huge community of other people, however in the previous couple of years I’ve long past deeper with fewer other people and it’s been superb for me in my opinion and for my enterprise.

By means of distinctive feature of fewer other people, I felt much less like I had to meet as many of us as imaginable and as a substitute that I may just pass deeper and feature high quality conversations with extra other people. It labored, and I’m for it.

Ask “Why”

I’ll be truthful – there have been some other people each in 2017 and 2018 at CaboPress that I judged, once I hadn’t met them but. I’m no longer pleased with it, however it’s true.

Considered one of my centered during the last 12 months has been to be extra inquisitive and not more judgmental. As an alternative of being judgmental, I selected to invite myself why they could be there. And the one approach to reply to that was once thru having conversations.

And thru the ones conversations, I were given to understand some superb other people.

In a similar fashion, when any person puzzled one thing in my enterprise (as I’ll extend on beneath) I selected to invite “Why do you are saying that?” as a substitute of in an instant protecting myself.

The ones “why”s made the entire distinction.

What were given you right here gained’t get you there

Trade is a adventure. Once in a while what has served you smartly to get so far isn’t going to take you to the place you need to head.

I feel I first heard that from Wil Reynolds, however it was once bolstered at CaboPress right through a dialog.

Any individual was once asking me who my enterprise’s major competition are, and I advised them. They went and checked out the ones competition, then my website online, and requested me:

“No offense, however are you a prime worth vetted community or a shitty listing?”

Ouch. When additional pressed, they mentioned:

“Your ‘competition’ have hundreds of other people indexed, you’ve gotten about 90 purposefully. So, are you a prime worth community or a shitty listing?”


Watch this house.

Get transparent on who you’re

At CaboPress 2017, at the first evening any person requested me if I used to be on the proper desk once I went to the Product desk. I noticed right through the process that dinner that I used to be certainly on the improper desk, that my enterprise had in truth turn out to be a services and products enterprise.

That realization modified many stuff for the previous 12 months.

Whilst my enterprise has grown smartly during the last 12 months (simply employed my first FT particular person, generated over $20M in annualized mission earnings over the primary three quarters of 2018), I’ve in my opinion had some struggles.

Don’t get me improper – 2018 has via a long way been my best possible 12 months on the subject of how just right and strong I think concerning the enterprise, however it’s additionally had its exhausting occasions (a few of that have been brought about via a nasty response to a drugs as a result of my herniated disc). Alongside the way in which I’ve felt like some issues within the enterprise are misaligned.

Taking a step again at CaboPress let me after all see the ones misalignments and likewise how they’re misaligned with me in my opinion, the imaginative and prescient I’ve for the corporate, and who I’m changing into as an entrepreneur and a pacesetter.

As soon as once more, watch this house.

Thank you Chris et al

I’d be remiss not to take a minute to thank Chris in my opinion. Your mentorship over the previous couple of years has been helpful and my enterprise almost definitely would no longer be right here if no longer for you. Thanks for being so giving to others. You’ve impacted my existence and plenty of others in a large approach.

And a large due to the entire unbelievable conversations I had at CaboPress 2018. Thanks Brian for each the tactical and strategic talks we had about productized services and products and personalization. Thanks Joe for the deeper existential chats and the good cigars. Thanks Jennifer for the continuing mentorship on automation and existence stability and construction the enterprise that helps your existence. Thanks Chris for the deep questions and ideas about existence and enterprise.

Listed here are a couple of extra footage to remind all people of the impactful week that CaboPress 2018 was once:


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