Episode Overview
What does it take to recognize when you’ve outgrown the path you thought you were on—and have the courage to choose a different one? In this episode of Real Talk, Mark O’Donnell, Visionary at EOS Worldwide, sits down with EOS Implementer Chris Heileman to unpack a journey shaped by early entrepreneurship, hard-earned leadership lessons, and a pivotal decision to redefine success.
Chris reflects on growing up with limited resources, finding opportunities where he could, and steadily building a career in the restaurant industry that took him from entry-level roles to the CEO seat. Along the way, he shares what worked, what didn’t, and how a failed concept revealed deeper issues around focus, alignment, and leadership structure. That experience ultimately led him to EOS and to a realization that his strengths, energy, and long-term vision were pulling him in a new direction.
The conversation explores what it means to let go of the vine, the impact of having the right people in the right seats (RPRS), and the clarity that comes from aligning work with life priorities. Chris also opens up about the personal moments that shaped his decision to become an EOS Implementer, the habits that support his day-to-day discipline, and how he now measures success through balance, mastery, and meaningful work with clients.
Key Takeaways
- Early experiences shape entrepreneurial instincts: Chris’s childhood ventures reveal how problem-solving, creativity, and leadership start long before formal business roles.
- Success without alignment has limits: Even profitable businesses can stall or fail when core focus, vision, and leadership alignment are unclear.
- EOS shows role fit, not just performance: Knowing the difference between Visionary and Integrator work helped Chris recognize where his energy and strengths truly belonged.
- Letting go of the vine enables scale: Embracing the Delegate & Elevate Tool and placing the right people in the right seats transformed the business and Chris’s leadership load.
- Expert guidance accelerates adoption: Working with an EOS Implementer brought clarity, proper timing, and accountability that self-implementation alone couldn’t provide.
- The EOS Life is built on discipline: Intentional habits, structured time, and clear priorities create balance, impact, and long-term sustainability for leaders.
Full Episode Transcript
Early Entrepreneurial Roots
0:01
Mark: This is just to bring out all of the fantastic stories of our implementor community. We have over 850 EOS Implementers doing business in 40 countries, and you are in Grand Rapids, Michigan. So I want to dive in and, one, thank you for being on, and two, ask what is your entrepreneurial story? How did you get here? Tell us a little bit about yourself.
Chris: Yeah, well thanks for having me on, Mark. I’m excited to do this. I’ve been looking forward to it. So, entrepreneurial story—if I went back, I would say I was a childhood entrepreneur. I was kind of a hustler when I was a kid. We were really poor, and so I was always trying to find ways to make money. My brother and I were always hustling, always looking for ways in the neighborhood to make money.
My first real entrepreneurial venture was in Michigan. We have a 10-cent bottle and can return. I recruited some of the kids in the neighborhood, including my little brother, and we helped collect cans and return them to make money that way.
Then I found out—I’m not sure where I learned this—but you know the movie Goodfellas, where they had that big heist at the airport, the biggest in history? Well, we figured out what ours was. There was a beer distributor nearby, and it was a little nefarious in our dealings. We found out they had a bunch of beer cans, and we found a way to get our hands on them.
I hired a bunch of kids in the neighborhood to help return them because these were huge bags of cans and bottles. That was the business until it all fell apart, when they started trying to pilfer them and return them on their own. It just kind of fell apart.
That was my first real business: getting everybody together and sending them off to different stores to return the cans. I didn’t want to walk into a store with a giant bag of cans, so I figured if I could get all these kids together, they could return them, keep some of it, and bring the rest to me. I also had paper routes and mowed lawns, all that kind of stuff.
Mark: It sounds like you were missing an enforcement mechanism for your aluminum can cartel.
Chris: Yeah, that would have been good to have—an enforcer to strike some fear into those kids.
Mark: That would have been a good idea. Your Visionary brain would have been helpful.
Building Restaurant Leadership
3:13
Chris: Yeah. Then I got into the restaurant business when I was a kid, and I discovered I was really good at it. My first job was at Burger King. I could flip Whoppers faster than anybody, work the drive-thru, and I got really good at different parts of the restaurant industry. Once I started doing that and was able to make money doing it, that really became my passion.
I’ve held every role in the hospitality industry, from dishwasher to CEO of a company. I’ve done every job you could do in restaurants. I started in the back of the house as a dishwasher, then cook, then sous chef, then chef for several years. I loved that.
Someone gave me a shot at leadership. My mentor, Chef Dave, made me a sous chef and then a sushi chef. That was my introduction into leadership. I worked my way up, stayed in the back of the house for a long time, then moved into the front of the house—general manager, director of operations—and ultimately became CEO of a restaurant company here in Grand Rapids.
That’s where my entrepreneurial journey really started. I helped grow the organization from a small family restaurant into multiple locations and different concepts. I co-founded one that did pretty well, and another that failed miserably, which we learned a lot from.
That’s also where I got introduced to EOS. I read Traction and went to an EOS talk done by Ken Bogard. That just did it for me. After reading the book and hearing Ken speak, I thought, “This is everything I’ve been trying to figure out.” Gino had figured it out and put it into this simple, beautiful system. I went to a couple of EOS talks Ken did, brought my leadership team to the second one, and said, “We’re doing this.”
Finding EOS Alignment
6:26
As I went through the journey, I felt like I hit my ceiling as a leader. I felt like I had accomplished everything I was going to in that company. I had always thought my entrepreneurial journey would lead me into restaurant ownership, but I’m glad it didn’t—this was before COVID, and that would have been a very different story.
In the back of my mind, I always had this idea of starting my own consulting business. I loved teaching, coaching, and helping managers and leaders become their best. At first, I thought it would be restaurant consulting.
But once we started running on EOS and I saw what Ken was doing, I thought, “Man, that job looks really good. I want to do that.” I talked to Ken, read Entrepreneurial Leap and Rocket Fuel, and took the Colby assessment. That was transformational for me. I scored a 93 on the Visionary side and about a 60 on the Integrator side.
Looking back, I realized I had been performing Integrator-type roles that didn’t energize me. What energized me was building organizations, growing companies, opening new concepts. Rocket Fuel helped me realize the vision of the owners and my vision weren’t aligned. That’s when I decided to take the entrepreneurial leap and start my own EOS practice. I went to Boot Camp in August of 2021, about three years ago.
Mark:
Congratulations on the three-year anniversary.
Chris:
Thank you.
Mark: That’s a great story. You mentioned one failed restaurant. What do you think caused that failure, and what lessons did you learn?
Chris: Looking back now as an EOS Implementer, the big issue was core focus. The concept we tried to create was not in our core focus. We were a family-style restaurant company, and we tried to create a high-end, upscale concept like you’d find in downtown Chicago. Grand Rapids wasn’t ready for it, and it wasn’t our sweet spot.
We also lacked alignment. We didn’t have a great leadership team all on the same page. Owners wanted different things, and I wanted different things. We lacked discipline, focus, and accountability. Having EOS would have prevented us from going down that path.
Choosing a New Path
12:27
Mark: Six successes and one failure is a pretty good hit rate.
Chris: I agree. Most businesses fail. That experience definitely shaped how I think about running businesses and how I coach my clients. I follow the EOS process and tools, but when I see something familiar—something I’ve experienced—I put on my coaching hat and say, “Here’s what I’m seeing.” Interestingly, I don’t work with restaurant companies, though I’m starting with my first one next week.
16:50
Mark: When you were CEO, you mentioned being both Visionary and Integrator. How would things have been different with a true Integrator?
Chris: It would have been life-changing. I held onto everything—finance, operations, everything except sales and marketing. Letting go of the vine was totally foreign to me. Once we implemented EOS, I embraced delegate and elevate. I filled the finance seat, the ops seat, and that ops leader became the Integrator. Eventually, I delegated and elevated myself out of a job intentionally.
Mark: Did you self-implement EOS or hire an Implementer?
Chris: We did a 90-minute meeting in February 2020, then paused because of COVID. I self-implemented through the summer using the books and free tools. I didn’t even know about Boot Camp at that point. We hired an Implementer later that fall and did our Focus Day.
Mark: What was the biggest difference between self-implementing and working with an Implementer?
Chris: Having an expert in the room. I thought I knew EOS, but an Implementer knows when and how to introduce tools, how to teach them properly, and how to drive accountability. Ken pushed me hard, and that made a huge difference.
Mark: What tool created the biggest unlocking moment for your team?
Chris: The accountability chart. It gave us real structure. Also, Level 10 Meetings. Our old meetings were three hours long and accomplished nothing. Level 10s changed everything.
Mark: At what point did you realize you wanted Ken’s job?
Chris: Seeing the impact he had and realizing I could make a bigger difference helping many companies instead of just one. But the real turning point was a clarity break in 2020. I was working nonstop, and my wife told me she and the kids had a routine, and when I was around, I disrupted it. It made me feel like an outsider in my own family.
That hit me hard. I realized I needed to make a change. I decided to start my own practice, talked it through with my wife, and she supported me completely. Now my life is completely different. I’m there for my family. I had bro time every morning with my son before school. Everything changed.
Mark: That’s such a powerful story.
Chris: It really is. My life is balanced now. I wouldn’t trade it for anything.
Living the EOS Life
34:50
Mark: Where do you see yourself going with your EOS Implementer business?
Chris: I don’t see myself doing anything else. I love being an EOS Implementer. I’m focused on mastery and doing great work with my clients. I joke with my kids about opening a restaurant someday, but I’m not ready to lose a couple million dollars. I’m happy where I am.
Mark: The EOS life is really a byproduct of discipline. What habits make that possible for you?
Chris: Structure and discipline. My calendar is everything. It’s color-coded and precise. My assistant helps manage it exactly how I like it. I plan my week every Monday morning, hold a Level 10 with my assistant, and structure my days—from workouts to family time to work. When I feel off track, I go back to the calendar.
Mark: Have you always been this disciplined?
Chris: Parts of it, but being an Implementer gave me more control. Reading Seven Habits of Highly Effective People, implementing EOS, and having a personal VTO added more layers of structure.
Mark: What are the last books you’ve read?
Chris: Outlive by Peter Attia. It really changed how I think about sleep and emotional health. I’m also reading The Untethered Soul. Both have been impactful.
Mark: Chris, thank you for sharing your story. Congratulations on your journey.
Chris: Thank you. I’m grateful for the EOS community and for Gino creating this system. I’m so happy to be part of it and to live the EOS life.
Mark: Thank you for coming on the show. We’ll see you at a QC sometime.
