Unplugged at CaboPress: Fresh Insights and New Horizons

I’ve just returned from an unforgettable professional development journey that recharged and motivated me. CaboPress, an exclusive gathering designed for executives and leaders in the digital products realm, is expertly organized by the renowned business coach Chris Lema, set against the stunning backdrop of Cabo San Lucas, Mexico.

This exceptional event was introduced to me by Quickly Hire’s founder, Brad Morrison, and I can safely say it was one of the most insightful workations I have ever had. I am confident I now have the solid foundation required to tap into my full potential. Every moment of my time there seamlessly blended education, relaxation, and motivation.

Since our successful launch of Quickly Hire at the start of 2023, we’ve encountered numerous challenges and navigated uncharted waters. However, my experience at CaboPress has equipped me with the clarity to pinpoint my focus and refine my strategies for maximum impact in our business journey.

“Your struggles aren’t unique.”

This quote from Chris struck a chord because it’s all too common for us to internalize our doubts and insecurities about our performance, believing that we’re the only ones facing these challenges. This self-doubt often leads to imposter syndrome, causing our productivity and performance to fall below the standards we set for ourselves.

However, CaboPress provided an invaluable opportunity to connect with diverse attendees at different stages of business growth and grapple with similar issues. This forum became the perfect sounding board, reinforcing my enthusiasm for a role I’m passionate about.

A conference that exceeded expectations

CaboPress attendees on the beach

Conferences are some of the best places to learn from industry leaders, meet fellow professionals in your niche, and find new perspectives. However, the experience is often limited by masses of people that you might run into once or twice if you’re lucky. Additionally, you’re usually bound to the hotel lobby in your spare time and a cavernous auditorium during the day.

The difference with CaboPress is your experience is genuinely tailored to your individual experience. Everyone I had the pleasure of meeting felt purposefully matched, and that was reflected in the numerous ideas we shared and insights we took away. I later discovered that none of this was by mistake but rather methodically organized by Chris and the CaboPress team to give all attendees added value from each interaction.

Fueling inspiration with every session

Quickly Hire attendees at CaboPress

Each day at CaboPress begins with the option to partake in an invigorating group workout, with the rising sun over the ocean as your backdrop.

Following the morning workout, you’re treated to a breakfast buffet I could happily eat for the rest of my life! It was the perfect opportunity to break bread with your fellow CaboPress attendees. From here,  attendees were divided into smaller groups to hear valuable insights from the designated speaker. I can’t stress enough how priceless these hour-long sessions are. In fact, I’d confidently trade several modules from my MBA for just one of these experiences!

These sessions fuelled how Quickly Hire intends to move forward—the primary beneficiaries being existing and new customers. Using this newfound knowledge, we can directly enhance our hiring practices, streamline processes, and ultimately drive growth and success for existing and new clients.

Elevating leadership and effectiveness

Attendees at cabopress meeting each other

Each session left an indelible mark, offering practical takeaways and a renewed sense of purpose that will undoubtedly shape Quickly Hire’s and my business journey. 

Here are just a few of the outstanding speakers that made CaboPress a fantastic experience:

  • Carey Nieuwhof shared profound insights on becoming a more effective leader.
  • Brennan Dunn exhibited the transformative power of effective segmentation and a tailored approach to enhance your processes.
  • Joanna Wiebe challenged our perspectives on website copy with her game-changing approach to conversion content.
  • Jorge Ahued explored the art of effective onboarding and creating a familial work culture.
  • Chris Lema outlined the distinct approaches required when moving up-market and highlighted common startup bottlenecks.
  • Jennifer Bourn provided expert guidance on generating repeat business, a vital skill in today’s competitive business landscape.

Becoming a reflective practitioner

CaboPress attendees in the pool during a seminar

CaboPress was a profound experience that reaffirmed my professional and personal journey. It highlighted areas for improvement and equipped me to streamline processes effectively. 

As we continue our upward trajectory, I now understand the growth challenges that lie ahead and how to leverage them for immense progress instead of getting bogged down. 

Every business stage brings its own challenges, and the key is not to burn out but to embrace them as part of the journey. CaboPress provided a safe space for vulnerability, enabling connections and insights that transcend conventional networking experiences.

Surprisingly, after an indulgent all-you-can-eat-and-drink conference, CaboPress also motivated me to incorporate healthier exercise and eating habits into my daily routine. The combination of sunrise workouts and discussions on work-life balance energized me to redouble my efforts. I’ve already embraced early morning workouts, finding that even a brief session ignites my creativity.

Shaping the Quickly Hire path

CaboPress attendees in front of the beach

At CaboPress, I uncovered invaluable insights that will shape our company’s evolution. While our roots lie in serving digital agencies, owing to our connection to GoWP, I sought to understand better how we can support startups and enterprises. 

Engaging with experienced attendees gave me fresh perspectives on sales processes, account management, and strategic product development, which are crucial for our growth. This newfound knowledge empowers me to make immediate improvements and chart a dynamic path forward. 

Additionally, sharing thoughts with my software developer roommate sparked exciting ideas about connecting professionals with burgeoning companies and the pain points associated with the freelance side of the gig economy.

I extend heartfelt gratitude to the conference organizers, speakers, attendees, and hotel staff for their contributions to this incredible event.


  • Kolby Joyce

    Kolby is an Account Executive at Quickly Hire, a managed marketplace that matches vetted freelancers with businesses for ongoing collaborations. He lives in Richmond Virginia with his partner Darling. In his spare time, he enjoys being active outdoors with friends and family.