CaboPress – A Business MasterMind (I Think)

For the past three years Chris Lema has invited me to join him at his event – CaboPress. For three years I have declined the request.

I declined previously for two reasons:

  • Didn’t think I had much to offer,
  • Afraid of the impressions hanging out on a resort in Mexico would have on my team.

What I failed to realize however is that it wasn’t about what I could offer, but the impacts it would have on me as an individual, and more importantly the renewed insights I could bring back to the team. In short, like many of the decisions in my life, I was an idiot.

This year, with the beginning of a new chapter in my life I said yes. As I sit here and reflect on that decision, I feel strongly it was one of the best decisions I have made in a long time. 

The CaboPress Experience and Insights

This year I was a host at CaboPress. I was asked to lead two conversations – Hiring and Acquisitions (Selling Your Company). Notice that I reference the act of “Leading a conversation” not giving a talk. I believe that’s a key distinction worth highlighting.

As with most things, I have never led a conversation like this. Or have I?

In retrospect I realize that the idea of leading a conversation, while foreign to me at first, was very natural as it’s something I do on a daily basis.

I didn’t choose the topics. This is Chris’ event, as such he curates every aspect – including the exact conversations he wants to happen. It provides him an opportunity to clearly define the experience and value he wants his attendees to walk away with. I have a new found appreciation for this approach.

The most interesting, impactful difference, was where the conversations occurred. They are in a pool, with a beautiful backdrop, with heat on your back and cool water running over your skin. Imagine the state you are normally in when in a pool (minus the times in Vegas); the odds are you’ll reminisce to a peaceful experience. There is something disarming about being in your swim trunks, in a pool, physically detached from your armor of clothes and electronic defenses that lowers your daily defenses.

I believe it’s the environment that facilitated the conversations, and coincidently new relationships, I was able to foster.

Impactful Conversations

I travel a lot, and have done so for many years. Been around the world multiple times, met some amazing people and have had some of the most interesting conversations. My conversations at CaboPress rank up there with some of the most interesting, and will undoubtedly will be some of the most memorable and impactful for me.


Because I found them not be pretentious or exhausting. They were genuine. The conversations were not superficial, and not one conversation carried an ask. It felt as if we all went in, regardless of our backgrounds, with our intentions to make it as beneficial as possible. To do this, we all had to actively let our guards down and speak frankly.

I watched the introverted work the courage up to ask, “Excuse me, can I get a minute of your time.” I watched the extroverted working on their active listening skills.

Unlike most events, these were not full days sessions. They all started at 9 am, and ended around noon. The rest of the day was spent as you wished, and coincidently most of us continued to hang out with each other. We continued the conversations well into the evening. Unlike other events where I normally have to disconnect myself from the experience, here I found myself engaged the entire time.

Most Impactful Session

I enjoyed each session I attended, but one specifically stood out to me – Mental Health, led by Dr. Sherry Walling; Founder of ZenFounder. A clinical psychologist specializing in executive coaching for entrepreneurs.

It was impactful because like so many, I too have struggled with mental health. I’m not exactly sure why, but my aptitude and tolerance around the conversation of mental health has changed dramatically over the past couple of years. I have no doubt that it has to do with all the discussions Cory Miller, of iThemes, has been facilitating on the subject.

An image by Cory on the Iceberg of Life.

My specific mental health issues have been compounded by experiences that pre-date those of building and running a company. Something I have never talked about openly, outside of the VA and the safety of my home.

This talk, and our ensuing conversations, has inspired me to collected and share some of my thoughts. Which I’ll do in future posts.

Most Interesting Observations

The most interesting observation for me were the number of repeat attendees. Specifically, the impact this event has had on them and their companies.

I can think of two specific conversations with the Beaverbuilder and LifterLMS teams. In both instances, they both attributed their successes and decisions, to pivot from a service company to a product company, to CaboPress and the influences Chris has had on their professional lives.

How fascinating, to have this kind of impact over a three year period and see the recommendations and ideas come to life.

The World of Service Businesses

I really enjoyed talking to the Agencies that I had never heard of.

Two specifically come to mind:

Emagine, led by Brett and Bill, two kindred spirits that I am sure are my brothers from other mothers. Most have built a business that dates back to the 90’s building solutions for their customers. They employ over 50 people, and they don’t sell WordPress to their customers, they sell them solutions.

We’ve never had a customer care or ask about WordPress specifically. – Brett (Imagine with a Boston Accent)

Then there is MultiDots, lead by Anil Gupta. A 150 person agency out of India, built over the past 8 years. They are a full development shop; not just specializing in WordPress, but in a wide array of development efforts and supporting a number of large US and Canadian brands.

While brief, I was able to learn a good deal about Anil. He has always wanted to have a product company, but starting out he was limited in funds. As such, he built a service company. Now, with enough cash he is going back to his desire of products, while maintaining the operations of the project business.

I was specifically fascinated by his ideals around how to treat your people, and how the culture in India led him to implement some changes to help offset the norm. The most interesting to me was the housing allowance (no interest and no timetable to repay) he provides to his employees that are looking to buy a home (having a home in India is really important, but difficult to get a loan for).

My Final Thoughts

I want to give Chris Lema my sincerest thanks, and appreciation. You have been a friend to me when I least deserved it.

If you don’t know Chris: he’s the VP of Product at LiquidWeb, Story-Teller extraordinaire, Coach and friend of mine. 1,000 apologies for my stubbornness over the past few years, but know that I truly enjoyed the opportunity. I know you mentioned potentially pivoting in future years, but I encourage you to reconsider.

For those that I met and were willing to share vulnerabilities and stories, thank you. As I think back on the conversations I realize how little I know, and how much I admire what you are all doing.

I leave thinking: how can I take the fire that burns in your souls and transplant that into my colleagues and organization? How can I transfer the experiences you’re going through, and make that something we as an organization can instill in every person.

If you find yourself reading this, and find yourself on the fence about a similar event in your industry – just do it. Don’t worry, you’ll probably gain more than you realize. Yes, people will make comments etc.. but you know what, who cares? Your success will be defined by the decisions you make, not theirs… #beyou

I look forward to tracking each of your journey’s. I stand at your disposal and willing to serve.



  1. M Asif Rahman on October 22, 2017 at 1:50 am

    Nice write up Tony! Thanks for sharing!

  2. Sujay Pawar on November 2, 2017 at 2:43 am

    100% agree.. It was great to see you in person :)

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