Ep. 250 – Unleashing The Power Of Your COO

Today’s episode is a little different. Recently Cameron was featured on the Author Hour podcast hosted by Hussein Al-Baiaty, and we’re happy to give you the opportunity to hear that conversation. Cameron was there to talk about his latest book, “The Second in Command: Unleash the Power of Your COO.”

During their wide-ranging discussion, Hussein and Cameron discuss the qualities and behaviours that make a great COO, as well as some of the challenges they face on a daily basis. They explore Cameron’s early life growing up with entrepreneurial parents – particularly his father – and how they gave him the support and guidance he needed to come into his own as an entrepreneur. Of course, they also discuss the new book and some of the thought processes that went into writing it.


In This Conversation We Discuss:

  • Cameron’s background and how his path to entrepreneurship began at just seven years old.
  • The distinction between writing books and having books written, and why Cameron prefers one over the other.
  • Why his parents allowed Cameron the space to fail and succeed, and to learn from both experiences.
  • The importance of having an effective COO in your business.
  • Some of the biggest challenges faced by COOs.
  • The kinds of qualities a great COO should possess.



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I’m super excited about this episode. I got my man, Cameron Herold, with me. I’m a big fan. I got to say thank you for your time. I appreciate you joining the show. 

Hussein, thanks for having me. I appreciate it.

This is your fourth book with Scribe. However, it’s your sixth overall. It’s like you like writing or something. I love it because I’ve gained so much knowledge from you. I have some funny stories about 1-800-GOT-JUNK? but we’ll get to that later. I want to get our audience to know you a little bit. In doing so, I love going back in time and getting people to talk about their youth, where they grew up, the people that influenced them, and what got you into this entrepreneurship world, into the place where you’re at now. 

I’m going to cover that, but I need to address one thing quickly. No, I do not like writing books. I like having books written. That’s why I work with Scribe. They’ve made the process so simple for me. We can talk about that later. The thought of sitting down and writing a book is hard for me, and you guys have made the process so simple. Thank you for that.

Let’s go backward. I was groomed as an entrepreneur. When I was about seven years old, my dad was an entrepreneur. Both sets of my grandparents on both sides of my family were entrepreneurs. I was groomed as were my brother and sister and I to all be entrepreneurs. For a long time, my sister runs her own business. My brother runs his. I’ve run mine, but I ran one even when I was in university. I was 21 years old. I had twelve full-time employees in my own company. I’ve had that entrepreneurial venture.

In fact, I did a talk that was on the main TED website about raising kids as entrepreneurs. It was called Let’s Raise Kids to Be Entrepreneurs. It’s had over a couple million views. I was groomed to be an entrepreneur and thought like an entrepreneur, but got involved in an organization called College Pro Painters when I was in my early twenties. I was a franchisee. What’s interesting about a franchisee is you are an entrepreneur inside of a system. There is a system created for you and you get to execute it. In many ways, I was like a COO. I had this system and I just had to make it work. I didn’t have to think of it and create it all on my own.

I started to work full-time at the College Pro head office in coaching franchisees. I coached 120 entrepreneurs by the time I was 28 years old. When Elon Musk’s brother, Kimbal Musk, was a franchisee. I hired him, trained him, and coached him for a year. I also hired, trained, and coached Peter Rive, their cousin who built Solar City. Both were early-stage entrepreneurial. I was coaching before coaching was even a thing.

I left there and I was partnering with a chain of auto body collision repair shops. We built out a group of auto body shops to about 65 locations and took that company public. I left there and I was hired as the President of a private currency. Similar to what Bitcoin is doing, we did it many years ago. We had 30,000 companies buying and selling, using our digital currency instead of the US dollar. We sold that company, but right as the stock market was about to crash when the NASDAQ fell by 78%, we were selling right into that crash. The $64 million valuation, by the time we closed, was worth about $3 million.

When you’ve lost everything, what do you do? You become a garbage man. I joined my best friend, Brian. He had been my best man at my wedding. I joined him to coach him and help him grow a small business. I was employee number fourteen. It was called 1-800-GOT-JUNK? They had twelve franchises and wanted to grow the business. I joined and became his Chief Operating Officer. I took the company from 12 locations to 330, from $2 million to $106 million, and from 14 employees to 3,100 employees in six and a half years.

That was several years ago that I left there now. I started coaching CEOs of real companies all over the world. I’ve coached the CEO and the second in command at Sprint. I coached a monarchy in the Middle East. I’ve coached a number of technology companies that have sold for well over $100 million. I started an organization called the COO Alliance, which is the only network of its kind in the world for the second in command.

Considering you’re at Scribe, Zach Obront was the first COO at Scribe and was a founding member of the COO Alliance. JeVon McCormick came into one of our COO Alliance meetings because he was the second in command to Zach and Tucker. Brittany, who is your COO, was a COO Alliance member for a year as well. I’ve had three. Three of your people have been in the COO Alliance as members. I started a podcast a few years ago called the Second In Command Podcast. I’ve interviewed about 245 very top-level COOs of companies, of brands that we know the names of. I’ve written six books. That’s about it. That’s me on the business.

That’s about it. To say you’ve been busy since seven years old is probably an understatement. 

My first business at seven years old is I did coat hanger arbitrage. I collected coat hangers in the neighborhood and then I sold them to dry cleaners for $0.025 a coat hanger because dry cleaners used to pay you a recycling fee for coat hangers. I remember phoning them all and negotiating. I wanted $0.03 and they only wanted to pay me $0.02. I said, “How about $0.025?” The guy on the phone was like, “How old are you?” I’m like, “I’m seven and I want more than $0.02.” He goes, “Fine, I’ll give you $0.025.”

That is amazing. I love that. Who would you say contributed to that mindset? Was it your father, your mother, your aunt, your uncle that filled some of these things? In your environment, there are a lot of people doing those kinds of things. You absorb. Who would you say is the one that led that torch?

My dad, for sure. My dad was very entrepreneurial, had the idea of the week, and had a different business idea constantly. He inspired me. What my mom did well was she didn’t coddle me. Where so many parents nowadays, when you know Sally’s going to run a lemonade stand, “Let’s buy her a stand. Let’s stand out on the street and call people in.” My parents were like, “Go do your lemonade stand.” They would sit inside the house and I’d come in and talk to them about what wasn’t going well. They’d coach me and I’d go back out and do it.

They stood back and let me fail, stood back and let me succeed, stood back and let me learn from experience. They gave me ideas and coaching along the way and went back out. They also didn’t try to turn every little business venture into some big thing. If it was a 2-day business, a 3-week business, or a 1-year business, that was okay. They didn’t try to turn it into something else. My dad was on the entrepreneurial side of things for sure.

I love that because later on, I talk about the emotions of connecting to these businesses. Especially as a franchisee, you learn that this is a process, a vehicle that you get to drive forward. I feel like at a young age, you were observing and learning, but not getting too emotionally attached to one thing or another, and also learning to fail forward. That’s huge. You’re right. In this world, the helicopter mom and dad just try to do a little too much for that kid that could easily succeed without their inherent constant pushing. I appreciate that you put that in there. 

The child doesn’t learn enough if the parents aren’t letting them learn. If the parents are sitting there calling in the cars to come to the lemonade stand, the kid’s not learning how to do that. If the parents are negotiating with the neighbor, the kid’s not learning how to do that. The parents telling the neighbor “Buy three,” the kid’s not learning how to upsell.

Every business I ran, I could rattle off sixteen different businesses by the time I was eighteen. I could tell you 1 or 2 very solid lessons that I learned from the experience of doing it that would’ve been removed had my parents been there. Each of those lessons stays with me in growing my people. When I’m growing leaders inside of a company, I let them fail and then I talk to them afterwards. I coach them, mentor them, and I use situational leadership. If I’m always doing the work for them, “Let me just do it for you,” that doesn’t scale a company at all.

That’s so powerful. That idea of interference and what you can learn from failing at something, it’s so powerful. Your book was profound. I’ve had the opportunity to swim through it. I want to get through it. This whole concept of the COO, let’s be honest, there are probably ten books a week written on and for the leader. This is the first one that’s come across, at least my lap, about the COO, the person that genuinely takes charge of so many different elements of the business. I know this has been your world, but what inspired you to write this book specifically for COOs? How has that resonated with the work that you do? 

There are two sides to that. The first part is there isn’t enough content out there for the COO or for the CEO on how to hire, recruit, onboard, and build an amazing relationship with their COO. Like you mentioned, there are thousands of books written for the entrepreneur. That was one, I wanted to write a book for that niche. I’d been the COO, I run the COO Alliance, I run the Second in Command Podcast, and my entire world is the second in command. That was one.

Secondly, I realized that if I could codify all these ideas and pull enough ideas from my COO Alliance members and pull ideas from the 245 Second In Command podcast guests and their content together into a great book, I could do them a service as well as giving them some praise and some shout outs, but also cull the wisdom of the tribe and share that. That was second.

Third was it’s going to become a marketing vehicle for the COO Alliance, the more people that learn about this concept and then say, “I should plug my COO into this network too.” There are 100 groups for entrepreneurs. Entrepreneurs can join YPO, Vistage, EO, Genius Network, or Strategic Coach, all kinds of groups for entrepreneurs. There are groups for marketers, engineers, and lawyers, but where do the COOs grow with each other? Where do they go to hang out with each other? The book will be a marketing vehicle for that as well.

That’s so powerful. I love the clarity in your vision and what you write about and how you get to fine-tuning those things. It’s exponential. This is your world. You want to build the base camp for them. You want to build all these opportunities and resources for them. You’ve done that so beautifully. I love that you laid that out so well. In your experience, what are the biggest challenges that COOs face, or maybe perhaps ones that you face during your work running those businesses? What would you say is the number one thing that your book tries to address as far as that challenge is concerned? 

The big one is that there is no quick fix to find a COO. I’ve had a lot of people in my business career ask me if I’d be the COO for their company. I’m like, “You don’t know anything about me. You don’t know anything about my real skills. You don’t know anything about the areas that I struggle in business. I don’t know anything about you. How could you possibly want me to be your COO yet?” They’re like, “You were a COO of 1-800-GOT-JUNK?” That company is completely different.

Let’s say that I was a single guy and I was looking for a wife. I was like, “You’ve been married before. Why don’t you be my wife?” Just because that person’s been a wife doesn’t mean she’d be a good wife for me. What I wanted to show entrepreneurs and CEOs is how you identify what you’re looking for, how you identify what you’re not looking for, and how you go and recruit that person to bring them into your business.

Once you have them, how do you build that strong relationship? How do you build trust? How do you build stronger communication with them so that you can build that strong yin and yang relationship with that COO? At what point is the person the wrong fit? At some point, the organization may outgrow that person as well. You have to understand that natural transition to make as well and how to make that transition.

As COO, you don’t necessarily own the company, but you’re helping it grow and thrive and all these things. However, opportunities may come up where you may be recruited to be a CEO somewhere else, like in this topic. How do you know, as a COO, that your time here, perhaps based on the conditions and all these things, is done and you’re onto something else more challenging perhaps, or more unique? Where did you find that moment of, “I’m ready to transition or go deeper into coaching?” 

My story’s a little different. The way I found out that it was the right time to go was my best friend who was the CEO and Founder of 1-800-GOT-JUNK? told me it was time to go. We had taken the company under my role as COO. I took them from $2 million to $106 million. He sat me down, he said, “You’re the wrong guy to take us to the billion. You’re the right guy to get us from $2 million to $100 million, but the wrong guy to go to $100 million to $1 billion.” I was like, “You’re right.” We both broke down crying and recognized it was time.

I should have left the company 6 months to 9 months before. I was too big at that point. We had 3,100 employees, we had 330 locations, we were operating in 4 countries, we had 13 interrelated businesses, had 4 countries that we were operating in, we had 248 people at the head office, and I was running 7 business areas. It was just big. That was too big for me.

When they replaced me, they brought the former president of Starbucks US in as my replacement. She walked in and went, “What a cute little company.” I knew it was the wrong thing and I probably should have left six months earlier. The way you know it’s the wrong fit is if you’re not having fun and if your skillsets are being so challenged that you can’t scale.

Typically, a C-level person can only go through 2 or 3 doubles in the size of the company before they probably can’t continue to run it. I did six. I doubled the size of the company six times in a row. When you go from $2 million to $4 million, from $4 million to $8 million, from $8 million to $16 million, you’re probably at your peak now. It’s probably a different style of organization at that point unless you can continue to invest in your own skills and grow your own skillsets. I was fortunate that I had a lot of strong leadership skills and could scale it, but I was the fifth of five leadership team members in a row to be replaced. I was the last of the original five to get replaced on that six-year path.

What a rapid growth. It’s so good to have that awareness as well, adopting the awareness to be like, “I’m capped out at my skill level,” to go invest in myself, to go get that training, whatever it is, to join obviously what you created, a place where I can grow as a COO so I can eventually perhaps grow into taking a company from a $100 million to $1 billion at some point. That’s so powerful to know what you are strong at, what you’re weak at, and to perhaps look for something else to challenge yourself. What happened after 1-800-GOT-JUNK? Where did you go on to? 

It’s funny because Brian, the CEO of 1-800-GOT-JUNK?, is a two-time Scribe author as well. He wrote WTF?!(Willing To Fail) and then BYOB: Build Your Own Business. Everybody should read WTF?! (Willing to Fail). Once I left 1-800-GOT-JUNK? I sat down and I did a series of journals. Every day for about three months, I spent twenty minutes every morning and just journaled. I did mind maps, lifelines, and lists. I’ve still got the actual notebook that I did it all in where I tried to examine what did I love about the business, what was I good at, what did I suck at, and what did I hate. In fact, a lot of my lessons from that journaling became chapter seventeen of my first book. It was called Letters to My Younger Self called Double Double.

SIC 250 | Power Of Your COO

WTF?! (Willing To Fail)

It was during that journaling exercise that I realized there were a few areas of business that I loved to do, that I got energy from doing, and I was really good at. That was coaching entrepreneurs. It was doing speaking events. It was doing media interviews and networking. Those were things that I was good at, I loved doing, and I got energy from. There was a bunch of other stuff that I might have been really good at, but I didn’t get energized from.

I tried to build a business that allowed me to only work in the areas of my unique ability and just not work on the other stuff. For fifteen years, I haven’t had any deliverables with any of my clients. I don’t do work for clients. I tell them what to do and then I let them go do it. The COO Alliance, I’m not even there teaching them all. I’m rounding them all up and letting them teach each other.

That’s so powerful to have that moment in time when you can sit with yourself and examine. I’ll tell you a funny story. I’m in Portland, Oregon, and I started a t-shirt printing company in college. We grew to about seventeen employees at one point, which was amazing. However, I had my girlfriend at the time, wife, one of her friends had a franchisee. He needed some t-shirts, whatever. I got to print some of those t-shirts at one point and I was super stoked because it was a big account. We did it twice. What’s interesting is, it’s moments like that where small companies like that, locally, trust in your work, trust in your product, and trust in what you’re doing. 

I too loved the media, getting out there, and getting my print shop in front of different organizations to be of service. I love this connectivity. At the end of the day, that taught me a lot. The printing world is huge. By the time I sold it in 2020, I had learned so much. I was in that phase in 2021 and even 2022 where I was doing a lot of self-examining and doing that journaling like crazy, trying to figure out what I loved about building that business and the things I don’t want to do again, which led me to coaching because I love teaching as well. 

I love this path and this moment in time where you get to solidify what you want to do next. Sometimes, people don’t give themselves enough time to rekindle those fires to be able to go deeper. You talk about Brian, but what other people that you’ve worked with that you help promote their work in a way that challenges them as CEOs to make those hard decisions? Can you give an example of something where people didn’t want to listen to you, but at the end of the day, made the right decision? 

There are a lot of those. I used to coach Elon Musk’s brother, Kimbal. I was a reference for Elon and Kimbal in their very first round of funding for Zip2 in January 1995. I’ve got a lot of stories I can go back to. Let me do a huge one for you. Sitting with the CEO of Sprint, the 82nd largest company in the United States, just he and I sitting in his boardroom talking about one of his core C-level employees, and Marcelo saying that he wanted to fire this guy but he couldn’t. I’m like, “Why not?” He goes, “He’s worked for us for twenty-plus years. He’s got a C-level title.” I’m like, “Last time I checked, you’ve got a CEO title. You’ve said this person is toxic, no one likes him, you don’t like his results, he’s too corporate and bureaucratic, and he is not entrepreneurial.”

Marcelo put a red X through his name. Marcelo said, “When are employees no longer going to be the problem?” I laughed. I said, “They’re always the problem because we care about people. The more that you care about people, it’s always the hardest part of your business. You’re running the 82nd-largest company in the United States. If people are a problem for you, they’re always a problem.”

I go to small businesses where I’ve coached someone who had to fire their mom or fire their best friend. There are all kinds of things. The hardest part with business is there is no manual for all of the stuff that we have to do. The original first franchisee for Portland committed suicide. We got a phone call that Phil Martin had shot himself. What do you do with that?

SIC 250 | Power Of Your COO

Power Of Your COO: The hardest part with business is there is no manual for all of the stuff that we have to do.


I remember getting the phone call and I turned to Brian. He was on the phone talking to somebody and he was crying. He was talking to Phil’s wife and I was talking to Phil’s GM. What do you do with that? Business is hard. That’s where if you have the right second in command or if you have that right COO, you’re not lonely. You’re not in that role all by yourself.

What Tucker and Zach had when they started Scribe, originally Book In A Box, was they had that two-in-a-box model to divide and conquer and build this thing, where Tucker was the spokesperson and the vision and Zack was operations and execution. They brought Britney as their COO and then they hired JeVon to come in as the CEO. You need to have some of those key people. Otherwise, it’s a really hard path as an entrepreneur.

Yes, you’re 100% right. From 2008 or 2009 all the way until 2020, there was some darkness and some loneliness. You just feel lonely. It’s hard to talk to your peer who may have a great career at some job or whatever. The entrepreneurial spirit is strong. However, it is consistently challenged because it’s wrapped in human emotion. 

The biggest learning thing for me was having someone in charge of operations, a person. I went through a refugee camp. I grew up in America, so it was a lot of distrust and things that I hadn’t worked through. I didn’t know how to hire someone, which brings me to my next question. What qualities do you think a person at COO-level, or at least 1 or 2 qualities, that you feel you have to possess this quality or this skill to be able to operate at this kind of level, especially when it comes to emotions and human interactivity? That’s the hardest thing when you get to that level of leadership. 

Let me give you the additional part of the Portland story. The Portland franchise later became purchased by Yoree Grozenok. Yoree was on our executive team at 1-800-GOT-JUNK? and he ran the division to sell franchises. The fact that he was now a franchisee and got to sell franchises and lead that division was really powerful for us because he understood it. Something that helped supercharge the company was how much he and his team then understood it.

Here are a couple of core things that you need to be a good COO. Any other C-level has to be good at their domain expertise. The CMO has to be great at marketing. The CTO has to be great at technology. The CRO has to be great at sales. The CFO has to be good at finance. The COO has to be good at interpersonal skills, has to be good at leadership development, and has to be good at everything the CEO sucks at, which is tough.

In some cases, if you have a CEO that is very strong at IT and engineering, the COO has to be good at everything else. If you’ve got a CEO that is very strong at sales and marketing, you’re going to have a COO that might have to be strong at technology. It’s a real weird animal that you’re trying to recruit for. It’s the person who is so strong at what the CEO is weak at and a relationship that becomes, “I’ll show you the cover of the book, like the yin and yang.” It’s the real yin and yang relationship that you’re looking for, that true trusted partner. That’s what supercharges.

That brings a lot of self-awareness to the table. It’s like having those meetings sitting down with potential people that you’re going to work with as a COO, being aware of what you’re great at, and what you’re bringing to the table is an exponential thing that could help both sides of the yin and yang. I got to ask you. What did you enjoy the most? I know you say you want to put the writing on someone else, but what did you enjoy the most about writing this book specifically in relation to the other ones that you’ve written? 

I liked it because I was passionate about the actual content. I cared about COOs. I cared about the actual content itself because I ran the COO Alliance. I had this group of people who I was very passionately engaged in, and that was the core for me. That was what made the difference versus the other books were all generally about business. There was no group that I was emotionally invested in.

I’ve run the Second in Command Podcast and I’ve had 245 podcast guests that are all second in commands. I’ve got 200 members of the COO Alliance from seventeen countries. It’s become a little bit of my world. In pulling the content together for them and helping them, I was much more connected than something that was very general.

When one of your readers picks up this book, and I’m sure many will, and begin to read through it and eventually put it down, what do you hope they feel when they put it down? When they wrap it up, what do you hope they feel and walk away with?

SIC 250 | Power Of Your COO

The Second in Command: Unleash the Power of Your COO

I hope they feel a sense of understanding what it was or what it is that they’re looking for. I hope they have a sense of understanding that there’s a path to get there. You said something about giving them base camp. I’ve been to base camp at Everest and I cheated. I took the helicopter in and I landed at base camp and had champagne breakfast.

There’s an actual walk to base camp. There’s an actual path and a route to get to base camp. There’s an actual path to going out and finding, recruiting, onboarding, and building a relationship with a strong COO. You can’t quick start over that path. You can’t just hire the first one that you encounter. You can’t say, “You’ve been a COO, come be mine.” I try to give people the system to do that so that they can have that success.

That’s amazing. Cameron, you are certainly a rockstar, my friend. It has been a pleasure and an honor to have met you. I was seriously looking forward to it because I felt like I had way too many questions for you at once. I was like, “This isn’t going to be a coaching session. This is an interview.” I wanted to say congratulations on your book. We all love those books that are so unique, but also directly speaking to us.

For those many people out there right now, the COOs of the world, and even CEOs who know they need to help their second in command, you are certainly that go-to person for that work. The book is called The Second in Command: Unleash the Power of Your COO. Besides checking out the book, where can people find you, Cameron? 

All six of my books are available on Amazon, Audible, and iTunes. I did the audio recording for The Second in Commandbook, so it’s in my voice as well. They can also check out the COO Alliance. They can go to COOAlliance.com. Lastly, take a look at the Invest in Your Leaders course. It’s InvestInYourLeaders.com.

Beautiful. Thanks again, Cameron. I appreciate your time today. It was an absolute honor. 

Thanks, Hussein. Appreciate it. It was fun.


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