30 Years in EO: 7 Lessons I Learned to Help Scale My Businesses

Back in 1996, after our internet access and content company was recognized as one of the fastest-growing companies in Canada, my brother and I were approached by someone who introduced us to EO. We attended a chapter event in Toronto, and we were blown away. I had no idea that such an organization of like-minded founders who support each other through the sometimes turbulent rollercoaster ride of entrepreneurship even existed. While I was initially skeptical about the time commitment, I gave it a shot and joined EO.

Now, 30 years later, as I reflect on my EO journey, I realize how significantly my participation in EO—everything from learning events, Forum, moderator training and workshops, universities, regional and global opportunities plus family events —has impacted my family, my personal growth, and most importantly, my businesses. Without EO, I truly don’t believe I would have been able to start, scale, and exit as many companies as I have.

Here are 7 key lessons I learned from EO that helped me scale:

1. Start vs. Scale Require Different Playbooks

In 2006, our public company was flatlining. What got us to early success—instinct and firefighting—was no longer enough. A board member even suggested replacing me as CEO. I reached out to a fellow EO member who introduced me to Patrick Thean of Rhythm Systems. At first, I resisted the structure and work we needed to implement. But Patrick insisted that we go all-in, or he would refuse to work with us. We implemented two days of strategic planning, 90 days of execution, daily huddles, core values, goal setting and more — we really went all-in.

The result? We tripled in size within a few years and sold the company to a Fortune 500 firm at a 125% premium to our stock price.

2. Hire Based on Personality

At an EO University, I discovered the DISC personality profiling system, a self-assessment tool that helps identify individual behavioral styles. DISC can help you understand how each person ideally prefers to interact with team members, what motivates them, and their preferred work style. I had each member of my team take the test and suddenly understood why some thrived and others struggled. It became our game-changing hiring philosophy. We built incredible teams by aligning roles with personalities.

To this day, I can usually profile someone accurately within two minutes of meeting them—it’s become somewhat of a party trick.

3. Get Comfortable Presenting in Public

Like most entrepreneurs, I dreaded public speaking. But through EO—where I presented at events and within my Forum—I gained the confidence to handle Initial Public Offering (IPO) roadshows and investor pitches. I remember once when I even rehearsed my pitch at a Forum retreat the night before the roadshow. My Forum members’ feedback changed everything and helped to make the IPO successful.

4. Learn to Lead Leaders

Leading high-level leaders can be as challenging as herding cats. Serving in EO leadership as a leader of leaders—in roles ranging from moderator to chair to regional chair—taught me how to lead dominant personalities. Entrepreneurs and most great executives tend to be strong-willed with a dominant personality. In other words, they are not “Yes” people. They tend to challenge you, which can be frustrating, but if you can manage that while simultaneously inspiring and aligning them, you can scale a company beyond what you imagined.

5. Delegate Responsibilities, Not Tasks

This shift is a game-changer. In Start mode, you do it all yourself. In Scale mode, you empower leaders to do what needs to be done. The key factor here is to assign outcomes—not checklists. When paired with the right hires, delegating responsibilities instead of tasks can unlock exponential growth.

I even discovered a hidden benefit: You get to sleep at night. Your team might be up worrying about the details at 3 am—but you won’t.

6. Hire a Coach Who Stretches You

Patrick Thean was that coach for me. He brought discipline and accountability—not to fix my C-players, but to help A-players operate at an even higher level. Think of your team like they are Olympic athletes, who need the best coaches in the world to perform at their optimal level.

I remember Patrick saying, “Colin, you need to stretch the rubber band.” So, that quarter we set a stretch goal: To migrate 15,000 websites in one quarter, which was double our usual pace. It was intense, but we hit it. The next quarter? 15,000 felt easy.

7. Core Values Matter

After hearing Verne Harnish, EO founder and creator of Scaling Up methodology, speak at a chapter event, our team implemented four core values with Patrick’s help. They became the heartbeat of our culture. I even took it a step further —facilitating a personal value exercise in my Forum and building Forum value statements with other Forums. Core values have become an incredibly important aspect in both my businesses and in my personal growth.

Bonus Lesson: Learn From Others

Back when I was a hotshot twenty-something entrepreneur, I thought I knew it all. I didn’t. EO taught me how to scale by learning from others.

That learning journey was the basis for Start. Scale. Exit. Repeat. —a decade-long project that became an award-winning book, where we interviewed 200+ entrepreneurs, many of them EO members, to uncover what works (and what doesn’t) when scaling a business. I hope the lessons I’ve shared will help every aspiring entrepreneur, established entrepreneur, or exiting entrepreneur as they navigate the wild, unpredictable, yet incredibly fulfilling ride of entrepreneurship!

Contributed to EO by Colin C. Campbell, an EO South Florida member, owner of Startup Club serial tech entrepreneur, and award-winning author of Start. Scale. Exit. Repeat., which recently won the 2025 Gold Medal for Entrepreneurship from Axiom.