CaboPress With Chris Lema: A Review Of The Best WordPress Conference I’ve Ever Attended

CaboPress was the best WordPress conference I’ve ever attended, and I am filled with gratitude as I sit in the Cabo airport waiting for my boarding group to be called. But CaboPress was more than just a great conference: I can count the last five days as among the most enjoyable of my life.

Update: I’ve written a review of my second CaboPress, and I’d love for you to check it out. The experience was just as valuable, but markedly different than the first.

Application Anxiety

I was nervous going into CaboPress. I was the baby of the group; the newcomer. Like so many others, I had applied on the CaboPress website and waited. My friend Jon Brown emailed a few days after I applied and asked, “You’re going to CaboPress, right?”

“I sure hope so!”, I replied. A few hours later, I received an email congratulating me on having been accepted into the conference. To Jon Brown of 9seeds: I am so grateful for your guidance, kind words, and friendship.

Sailboat at CaboPress

Prescription: CaboPress

While at a doctor’s appointment two weeks prior to the conference, my doctor asked what I was up to. I said, “Well, I’m going to this conference thing in Cabo. It’s really small, but it’s attended by amazing people. I’m looking forward to it, but I’m nervous too.”

Knowing that I’m in the technology world, he took his phone out out of his pocket, looked something up, wrote “CaboPress Chris Lema” on a Post-It note, and handed it to me. Surprised, I said, “That’s it! How do you know about it?”

My doctor explained that he is a fan and frequent listener of Brian Clark’s Unemployable podcast, and that he had listened to Chris’s interview with Brian where CaboPress was mentioned just a few weeks before. My excitement about CaboPress kicked into high gear after I listened to the episode later that day.

Grand FiestAmericana Resort CaboPress

Coping With Pre-CaboPress Imposter Syndrome

My friends can attest to my escalating level of nervousness in the weeks leading up to CaboPress. I knew I would be surrounded by a brilliant group of people and wondered if I would be able to contribute to a conference where the bar for knowledge and success was already set so high. CaboPress is about conversations and sharing, not about taking. If I didn’t have anything to contribute, my first year would probably be my last.

Not wanting to squander the opportunity, I listened to a 10xTalk podcast about how to get the most out of a conference and spent a few hours preparing my introduction and a list of goals I wanted to achieve. I imagined the best possible outcome, but CaboPress managed to exceed it. By the time the conference was over, I had accomplished every goal on my initial list and much, much more.

5-Star Resort Grounds at CaboPress

The Pool Of Talent

Jason Cohen ignored the “oohs” and “aahs” the first time. And the second time. The third time he stopped and turned around to see what everyone was staring at.

Jason, founder of the hugely successful premium WordPress hosting company WP Engine (check out my WP Engine coupon code and review if you’re interested), and I were floating next to each other in an opulent pool. It was our third day of morning sessions, all of which are held in beautiful pools adjacent to all-inclusive restaurants and bars at the luxury resort.

We turned around and watched a huge whale breach in the ocean and land on its back, making a huge splash. It was magical; one of those absurdly perfect, unforgettable moments. The group of twelve had been listening intently to Jason’s first-hand experience bootstrapping and fundraising for his first three companies (all of which were successful and he sold) and for WP Engine.

CaboPress Session In Swimming Pool

After taking a brief moment to appreciate the awesome wonder of the scene, we turned back to Jason to glean as much wisdom as possible from this person whom I came to deeply respect and admire, and am honored to have met. It took only a moment for me to realize that while whale watches can be purchased for ten or twenty dollars, my time was Jason was singular and priceless.

Nights at CaboPress were punctuated by conversations with over cigars and (for others) bourbon. The impromptu gatherings in one of several of the resort’s all-inclusive bars afforded me the opportunity to relax and to truly connect with the hosts, and that left me feeling that with time, hard work, and the guidance of the people like Chris, Jason, Brian, and Karim, I can succeed as well.

CaboPress Pool

PSA: Brian Clark Does Not Mince Words

The first evening, Brian Clark and I sat down and I told him about what I had been working on and how I was planning to grow my business. He listened and said, “Yeah, I don’t think that’s going to work at all.” Great.

He then furrowed his brow, took about a minute in silence to think, and suggested an alternate path to success that could absolutely work. In that half-hour conversation, Brian helped me to change the way I think about my business. I know that he genuinely wants me to succeed. Following up with him the next day, he said, “Yeah man, I just don’t want to see you set out on the wrong path.” He was right and his advice is spot on.

That conversation really exemplifies CaboPress and what it means to me. I didn’t get a watered-down, Pollyanna story — I got to sit down with a leader in the industry and get no-nonsense feedback. I wouldn’t have it any other way. A huge thanks to Brian, who is (for anyone who doesn’t know) a very cool guy.

Balcony View At CaboPress

Ruth’s Chris, Star Trek, and Westworld (written with added neuroticism for effect)

Wednesday evening, our group piled into vans and descended into the city of Cabo San Lucas to go to Ruth’s Chris Steakhouse. By this time, I was following Jason Cohen around like a teenager waiting to ask his crush to go to prom. He sat down. I sat down next to him and he didn’t swat me away. “Phew!”, I thought to myself. “I’m in.” (Just to be perfectly clear, I am highly exaggerating my level of neuroticism.)

At first, the conversation felt forced. Thank God for Joe Guilmette: An experienced skydiving instructor, his conversation with Jason about small aircraft — which was quite interesting — delayed Jason from realizing that he had made a huge mistake by sitting too far away from the hosts to be rescued by an “important client issue”.

Sure, I’d been in a Cessna or two — and rest assured that I let them know — but that wasn’t enough material for 2 more hours of small talk. Knowing I had to do something, I summoned the courage to ask a simple question. A courageous question. And so I took a deep breath, said a quick prayer, and through cracking voice, blurted out:

So, are any of you guys into Star Trek?

The conversation came to a grinding halt. For anyone who isn’t used to being picked last in gym class, allow me to clarify the circumstances: Whenever anyone asks a Star Trek-related question in public, fans have learned two main survival skills:

  1. Before responding, pause for one to two seconds and wait for someone wearing a varsity jacket to say, “Ugh. Star Trek is… stupid!” and, if that is heard, remain silent to avoid a beating.
  2. Temper your response so as not to appear too into Star Trek until you gauge others’ level of interest.

After what seemed like hours (but was more like an immediate response to my question), Jason responded, “Of course I like Star Trek.” So did everyone else, and with the exception of the Westworld discussion, our table talked Star Trek for the rest of the night. I have provided an excerpt to illustrate:

“What’s your favorite episode of TNG?”, I asked my roommate Joe across the table.

“Data’s Day,” Joe responded without hesitation.

“That Wesley Crusher was cute,” said Raquel.

Then, in an apparent, misguided attempt to fit in, someone said, “Which series do you think was better: The Next Generation or Enterprise?” Silence.

Rolling his eyes, someone looked at me and whispered what everyone was thinking: “Well, that’s a dumb question.”, and of course I agreed.

Later that evening, I asked Jason if he watched the HBO series Westworld. He said yes and patiently listened as I told him one of my theories about the show. Then he said, “Do you want to hear my theory?” Of course I said yes, and then he blew my mind.

Cabo Arch At CaboPress

The Karim Of The Crop

Another CaboPress highlight was the series of conversations I had with Karim Marucchi about the direction of my business. After asking permission to “be mean” (which I consented to immediately, knowing he was just going to be helpful and direct), Karim gave me an alternative, less-flattering interpretation of what I had said during my introduction. I agreed with his assessment. Then he asked a series of tough questions about my business that I couldn’t answer. Karim then told me to CaboPress confidential to help clarify my thoughts and I promised that I’d follow up with him soon.

I worked hard during my off-time to accomplish the task. On Thursday, I had the honor of sitting down with Karim for a thorough discussion of what I had done. Warning me that he would “be mean” again and interpret my work like an investor would (Karim’s way of saying, “Put on your big boy pants because here comes the truth!”), he asked me questions and gave me honest feedback about the work I had done. He poked holes in the weak parts and helped me to build upon the good.

Karim suggested that we follow up again via Skype after I’ve made more progress, an offer that demonstrates what CaboPress is all about. The giving goes beyond the conference, and Karim wasn’t putting on a front for me. His generosity and willingness to help is genuine. My experience with Karim is one of many that in itself would have exceeded my expectations for the entire conference.

This article could go on and on. I haven’t mentioned any specifics about what I learned, because that’s part of the deal: CaboPress is a place where everyone can be honest; where numbers can be discussed and problems shared with the knowledge that they go no farther than the walls of the 5-star Grand FiestAmericana resort.

Cabo from Pirate Ship

Chris Lema

Before wrapping this up, I wish to extend Chris Lema a heartfelt thank you. The amount of planning that goes into this event is formidable and its execution was impeccable. Chris is one of those “giving by default” individuals and I must admit that I still feel a little bit intimidated in his presence, despite his protestations that I need not feel that way.

What’s really, really cool is that the hosts at CaboPress aren’t standing still themselves. They don’t say, “We’ve made it and we’re done.” Instead, they say, “We’re growing too. Here’s how we got to where we are, and here are the challenges that we face as leaders.”

In spite of the amazing level of success he has already achieved, I believe that Chris’s career remains on a sharp upward trajectory. CaboPress is a reflection of Chris’s quiet leadership and dedication to the WordPress community. His attitude and passion permeate the entire CaboPress experience and he genuinely wants everyone to succeed.

I think what most impresses me (and possibly intimidates me) about Chris is his refusal to allow others to believe in the limiting thoughts and excuses that hold them back. Even though I sometimes think “I’ll never be a millionaire”, I know that Chris believes that’s just not true. And through his belief I’m able to challenge and overcome the limitations I place on myself.

He doesn’t just talk the talk: Chris has overcome these thoughts himself, and he wants to help others do the same. My time with Chris left me feeling energized, inspired, and grateful.Pirate Ship At CaboPress

Pillaging And Plundering The Open Source Community

I would be remiss if I did not mention the pirate ship. Yes, we had dinner on a pirate ship. I said that I wanted to be a pirate when I was 7 years old, and 25 years later, that wish came true.

Pirate At CaboPress

A Welcoming Community

I mention this not to brag, but to demonstrate the quality of the people I met and their willingness to accept a relative newcomer to the community at face value. Before I left, two companies offered to bring me on as an SEO consultant, and the developer of another plugin told me that our half-hour conversation in the Cabo airport “blew his mind” and that the cup of coffee he bought me was “the best 50 pesos he had ever spent”. (It may well have been the only 50 pesos he had ever spent, but I’m honored nonetheless!)

During one conversation, Jason Cohen told me, “It’s amazing what you’ve been able to build. I think what you really have is a world-class CaboPress secret. If you go to CaboPress to get awesome advice, you should be able to make 100x more than you’re making now.” (What happens in CaboPress stays in CaboPress.)

In short, I came in nervous and left with the feeling that I had contributed and that I belonged. Payette Forward is all about giving back. So is the WordPress community, and CaboPress is an example of that attitude in action.


My roommate, Joe Guilmette, deserves a special shoutout. I have been using WP All Import, the plugin he develops and supports, for the past year and I’m a big fan. It was awesome to sit down with the developer of a plugin I have come to love and have him show me how he uses the plugin, and some awesome features I didn’t know about.

I also want to thank Blair Williams of MemberPress for your awesome conversation and for making me feel welcomed (check out his CaboPress review too!), and Sherry Walling for the awesome session you led on mental health and our fabulous discussions throughout the week. To my fellow Group 7s, especially Chris Wallace of Lift UX and Tara Claeys of designTLC: thank you for your guidance and inspiring conversation. And thank you to everyone else as well.

Sunset From Pirate Ship At CaboPress

CaboPress: The Best WordPress Conference I’ve Ever Attended

For me, CaboPress was one of those singular experiences that couldn’t have been scripted better if someone tried. I’ll be forever grateful to Chris, the stellar hosts, and the brilliant attendees who surrounded me. I’ve made new friends and left feeling like I truly do belong.

I still have a lot to learn. I am honored and humbled to have had the opportunity to attend, and I hope to have the same opportunity again next year. They say that when the student is ready, the teacher will appear. I submit that when the student is ready, Chris Lema will accept his or her application into CaboPress, a slew of teachers will appear in the stunningly beautiful pools of the 5-star Grand FiestAmericana resort, and all will learn together as whales breach over the open seas.

CaboPress Year Two: Different

My approach to my second CaboPress was markedly different than year one. Last year I arrived with solid plans for my business, and I was sure they were going to work. In no uncertain terms, the hosts told me that plan A wouldn’t work. Plan B, they said, sounded better than plan A, but they weren’t too crazy about it either. But I was determined to make plan B work. It was one or the other in my mind, and I chose the other.

After many months of trying and very little succeeding, I arrived at this year’s CaboPress much more receptive to feedback about the overall direction of my business. I was OK being a blank slate. This year I came to really listen and learn.

On The Plane To CaboPress

“Wait… So Why Are You Here?”

CaboPress is branded as a WordPress conference. The first question someone asked me on the way to the resort was, “You run an iPhone website, right? You’re a publisher. What are you doing here?”

It wasn’t the first time I had been asked. After several people (including Brian Clark) raised the question last year, I started to wonder too. What was I doing at CaboPress? Shortly after this year’s conference was announced, I asked Chris Lema.

The truth is that CaboPress is as much a business conference as it is a WordPress conference. Yes, I have an iPhone website with great content (which is built on and inexorably linked to WordPress, and I’m a developer, and I can help WordPress businesses with my skillset). But the other guests and I share more in common as business owners than may be obvious at first blush.

And so I developed a simple response to the question about why I belonged: “Because we are both entrepreneurs and face the same challenges. And because Chris Lema says I do.”

Reflections On The Community

One thing I notice about the WordPress community is that there are a lot of great products created by people who don’t know how to market or charge enough money for them.

There are exceptions. When I look at the hosts and the guests, business savvy seems to me to be the distinguishing factor.

But They Have A Point.

Business conference aside, I am going to be attending iPhone technology, affiliate marketing, and online publishing conferences over the next year. Diversity is wonderful for knowledge, and I do need to make endemic connections in my space.

Jennifer: Bourn To Give Great Advice (I Know…)

I explained the issues I experienced to Jennifer Bourn, and she told me why my ideas for an SEO course hadn’t worked out: Regardless of my level of knowledge or success in the field, people don’t know or trust me as an authority in that space. That information helped to alleviate my own frustration and gain clarity about what went wrong. These are universal business lessons that I need to learn, and the CaboPress hosts are wonderful teachers.

Actionable Insights, No BS

Syed Balkhi gave me honest feedback and helped me realize that to succeed, I need to focus on my strengths and on what’s working. He drew upon his experience as a publisher, product owner, and businessman to share insights into new opportunities for my business to grow.

Lema On Leadership

I’m always looking to improve my skills as a leader. One of the most poignant conversations I had was with Chris Lema. I asked, “What would you say my greatest weakness is as a leader?”

“I’d say you’re asking the wrong question,” he replied. “If a child gets one A, one B, and one C on a report card, I wouldn’t dwell on the C. I’s ask them how they achieved the A and B, and how they can apply those strengths to bring the C up.”

The View From The Hotel

Conversations Over Lunch

My assigned lunch group was outstanding. I met Chris Badgett of LifterLMS at last year’s CaboPress and he’s become a friend and trusted source of information over the past year. He invited me to do my first-ever Podcast interview on the excellent LifterLMS podcast this year, which is something I’ll always be grateful for.

Rahul Bansal, CEO of rtCamp, is the creator of the web hosting software I use on many of my websites. Anil Gupta of PixelDots almost moved me to tears with the story of how he got started and the amount of charity work he does.

On the last day, Aleksander Kuczek guided the conversation in an unexpected direction with the following question: of the seven deadly sins, which motivates you? As a table made up of entrepreneurs, pride was the obvious choice for all of us. We decided to dig deeper, and that’s where things got tricky. Those types of deep, provocative conversations exemplify what CaboPress is all about, and we grew closer from the experience.

The Unspoken Value Of CaboPress

Before I wrap up my review of year two, I want to touch on the value of this conference. I had many one-on-one conversations with people who charge hundreds of dollars per hour for consulting, and I had access to people who don’t sell their time at all (because they don’t need to). And it all took place at an all-inclusive 5 star resort. Despite its relatively high sticker price, from a dollars and cents perspective, CaboPress is a real bargain.

Suruci Dre Armeda Tony Perez CaboPress

With Dre Armeda and Tony Perez of Suruci

CaboPress Is A Good Thing.

Seeing as how this is a review, I’d like to share some personal reflections about the conference: CaboPress is good for the WordPress community.

It’s also a platform for Chris Lema to demonstrate his leadership and organizational ability. Chris’s name is on the swag. And it should be. 

To pull off an event like CaboPress is no small feat. Does Chris benefit personally from it? Yes, but his success does not preclude anyone else’s. It accelerates our successes. I’m proud to wear a shirt (last year’s shirt) with Chris’s name on it when I go to WordPress conferences.

What CaboPress Is Not

CaboPress is not a WordCamp. I’ve never heard the kind of information that’s shared in CaboPress at a WordCamp, and I certainly have never had the opportunities to have follow-up conversations about my own business with the speakers themselves.

WordPress: The NCAA Of The Tech World

The WordPress community prides itself on being a tight-knit, nurturing, democratic community from top to bottom. Speakers are not paid to speak at WordCamps or reimbursed for travel expenses. WordPress isn’t about competition; it’s about sharing and giving and learning. Except none of that is really true.

I’m no expert on the intricacies of the NCAA and I am not saying their decision not to pay players is incorrect. However, one possible explanation for the lack of real opposition to the practice of “no pay for play” is that there is no alternative for 99+% of players.

Not so with WordPress. There are several problems with promoting a culture that attempts to run counter to real-world business practices in an effort to be perceived as selfless. The purpose of this article is not to digress into a critique of the community at large. Perhaps that will be in a future article.

And so, my fellow members of the WordPress community: ask not what WordPress can do for you—ask what you can do for WordPress.” – No one, at least out loud

It’s my belief that one reason for the success of CaboPress is that it does not live in denial about what it is. Speakers aren’t only there out of the kindness of their hearts. Attendees pay a fair amount of money to attend, but still get more than they pay for.

CaboPress creates an environment that leads to open sharing for the same reasons the “open community” fails: By giving hosts free trips to Cabo, they are in turn motivated to share — because they’re being paid. By making attendees pay for the privilege of attending, they are made comfortable to ask hosts the difficult questions and not feel like they’re taking too much of their time. CaboPress works without the Press.

Backing up for a second: There are amazing, selfless people in the community who give and give and give. But they aren’t the leaders of the community. With few exceptions, they aren’t the millionaires. They are the people who buy into the ethos; who have learned to trust; and who may be disappointed in a few years.

In line with real world business practices and the reality of SEO currency, only two people have been given a “follow” backlink in this article: Chris Lema, whose importance to my development as a businessman goes beyond words, and Chris Badgett, who featured me and gave me the opportunity to speak on my very first podcast.

Since I’ve Been Back

Google Analytics After CaboPress

I started to implement what I learned as soon as I returned. Everybody in the WordPress community knows that SEO is a dynamic animal, but traffic on this website up 20% in one month. I’ve opened dialogs with affiliate partners. I’ve hired people. I’ve let people go. I’ve set projects aside and refocused on what’s working. CaboPress is a business accelerator.

New Direction

I came away from this year’s CaboPress with a renewed focus and new sense of direction. At the request of the hosts, I won’t share specifics, but the knowledge I garnered from our pool sessions was candid and drew upon the hosts’ personal successes and lessons they learned from their failures.

Chris Lema hosts a wonderful conference, and for the second time, I’m honored to have been counted as one among this amazing group.

About Author

I'm a former Apple employee and the founder of Payette Forward, and I'm here to help you with your iPhone.

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