CaboPress Review

From my perspective businesses need 3 types of help to be successful:

  1. Survival
  2. Growth
  3. Support

For me the annual CaboPress business mastermind event put on by Chris Lema provides assistance on all of those levels. Let’s looks at those types of help in detail:

Staying alive …

At the early stages of a startup, the goal is not to die.
A new business can be fragile. That was my experience with LifterLMS. It was fragile in the early days.
Getting one good new idea or learning from another entrepreneur’s mistakes can literally make the difference between business life or death.
I’ve learned many things in conversations at CaboPress that I took action on that quite literally helped us navigate the early fragile days of transitioning a WordPress agency to what has become a sustainable product company.

Scaling up …

Arguably the biggest benefit I’ve gotten from CaboPress is business growth.
I can literally trace back many LifterLMS business growth events in terms of revenue, user base size, and even entrepreneur happiness levels to conversations in pools, restaurants, swim up bars, hot tubs, and the sea at CaboPress.
Some people say it’s hard to track the specific ROI of investing time and money attending events. With CaboPress this is not the case. When I look in the rear-view mirror, the return on investment of CaboPress is crystal clear.
This year CaboPress literally paid for itself (before we even got to Mexico) from a conversation at an airport gate.

The hard thing about hard things …

Entrepreneurship is a lonely road.
As entrepreneurs we spend a lot of time in our heads, working long hours, and often not in the company of other entrepreneurs.
CaboPress for me is a refreshing break from the day to day, and a place to connect with other like-minded people with similar struggles and dreams (professionally and personally).

Specifically how did CaboPress help me?

1) Business relationships – I’ve developed business partnerships, created successful co-marketing with other companies, and built a much stronger professional network with great people.
2) Help transitioning from services to product business – Self funding a product as a bootstrapper is difficult. Funneling agency profits into product development comes with some lean times in the early days. A few key ideas about product road-mapping and marketing from the pools of Cabo allowed us to make strategic decisions that proved successful and allowed the LifterLMS product business to survive and thrive.
3) Tribal community – I’ve found various tribes throughout my life that I became a part of that were helpful and fun. A tribe is a place to learn, serve, and share experiences while also sharing some common goals and values. CaboPress is a personal and professional network of technology entrepreneurs that I’m grateful to be a part of.

Watch LifterLMS cofounders discuss CaboPress


This is a video episode version from the LifterLMS podcast called LMScast. LMScast exists to help course creators find success through ideas, tips, tools, and tactics including and beyond just the technology aspects of building a training based membership site.

2 ways to use these ideas around mastermind events in your education business…

1) Don’t go it alone – Education entrepreneurs need other education entrepreneurs. If you are a course creator consider joining the weekly LifterLMS Mastermind. It’s not in a pool in Cabo. It’s in Zoom. But it happens every week. And there is so much to learn there and an opportunity to join a community of people that get you.
2) Build your own mastermind event for your community – I’m a big fan of creating learner results through a concept I call Course PLUS.
Learners often need more than just course content to get results and achieve the transformation promised in the course marketing. What could you add to your course stack to make it more effective?
COURSE +

  • Coaching
  • Community
  • Mastermind
  • Live Events
  • Retreat
  • Virtual Events
  • Office Hours
  • Guest Lectures
  • Products
  • Services
  • Productized Services
  • Group Projects
  • Software

Could you perhaps add and coordinate mini mastermind groups of 3-6 people as part of your training program for accountability and support?
Could you perhaps offer a live on-location, high level mastermind event or retreat for your most engaged, committed students at an additional cost?
I learned a long time ago that masterminding is a key ingredient if the goal is to learn fast and increase the odds of success in any venture.

Here’s what I’d like you to do next…

Explore Chris Lema’s website and leadership blog where you can get inside the mind behind the mastermind.
Consider creating a live event to pair with your online course or training based membership site.
Perhaps join a mastermind that meets regularly. Don’t know where to start? Try this.
Add social learning components to your LMS website so your students can learn from each other, not just you.

More 2018 CaboPress news

If you want to learn more about CaboPress, check out these recent resources:

Chris Badgett

About the Author: Chris Badgett

Chris Badgett is the founder and CEO of LifterLMS, a learning management system for WordPress. He is an expert in the best WordPress LMS plugins. Chris helps education entrepreneurs create, launch, and scale high-value online courses and training-based membership websites. He believes in democratizing education in the digital classroom and contributing as much as possible to the open-source WordPress community.