970: Second In Command with Cameron Herold
13 Nov 2025 · 23 min
Cameron Herold helped grow 1-800-GOT-JUNK from $2M to $106M and now runs the COO Alliance, a global community in 17 countries. He explains what separates great second-in-commands from weak ones, why CEOs often fail to trust their COO, and how the role changes as a company scales.
Questions this episode answers
17 countries
At least $5 million in revenue
About $40 million in revenue
One 3-hour online event per month plus two in-person 2.5-day events per year (next in-person at MIT).
285 COOs
Chapters
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Welcome to the podcast. This is your host, Seth Green. Today I have the awesome good fortune to interview somebody I consider a mentor and that I follow. Cameron Harold. Known around the world as the business growth guru. At age twenty one, he had fourteen employees by age thirty five, he'd helped build his first two hundred million dollars companies. By the age of forty two, he engineered one, eight hundred. Got junks growth from two million to one hundred six million dollars. He's got multiple best selling books including Double Double Meeting, Suck, Vivid, Vision, Free PR, The Miracle Morning, and my favorite, the Second in Command, How to Get the Most Out of Your Coo. Cameron, thanks so much for joining us.
Of course, Seth, thanks for having me appreciate it.
Our pleasure. So let's go back in time. You grew helped grow one eight hundred got junk from two million to one hundred six million. And then you chose to step aside.
Kind of. I was the second in command. I joined Brian as his fourteenth employee. When I left, we had three thousand one hundred employees system wide. And I had helped the company go from two million to one hundred six million. In that six and a half years, Brian and I met one Thursday morning thirty minutes before the leadership team meeting as we usually did. And I ordered my traditional eggs Benedict and he ordered a grapefruit. I went grapefruit. You've never ordered grapefruit. Fruit. He was my best friend. I mean, he's never ordered grapefruit. ¿What the fuck you doing? ¿Ordering grapefruit? And I'm like, I'm totally getting fired. And the first thing out of his mouth was, I think it's time that we part ways you were the right guy to take us to one hundred million. But I know you're not the guy to take us to the billion. So that was the day that the party was over and I had to go off and figure out my next trajectory. And Brian spent twelve months trying to find my replacements. And he brought in the former Starbucks President of USA to replace me. She came in and said, what a cute little company. And I'd been pulling my hair out saying, holy shit, this was big.
So congratulations on the incredible success not just from what eight hundred got junk, but everywhere. ¿So what do you? I think it's interesting that you write in the book about how different coos and different teams can get you to different levels.
Yeah. And by the way, that was totally the right decision that he made right. I was the right person for the season that they were in that very entrepreneurial million to one hundred million season. Their current coo, Eric Church. He and I have been friends for thirty five years. We started a fraternity together in Ottawa, Canada, in nineteen eighty seven. I was president year one, he was president year two. Eric has been an amazing coo from the one hundred million to four hundred fifty million. But he would have been horrible in the six and a half years that I was there because he didn't have the skill set to take it to the one hundred million mark. He did have the skills to go from the hundred four. ¿So it's a really strange role in trying to find the right person who fits you culturally fits the skill set and is there for the right season that you're in in that company as.
Well because you could certainly be the right person the right skill set but the wrong time, right?
Or yeah, or you could be the right person but in the wrong company. You know, I've been running the COO Alliance now for six years. We've got members from all over the world. I've interviewed two hundred and eighty five COOs on my second in command podcast. I would be a horrible COO for ninety five percent of their companies because I either don't match the right season that they're in, or I don't have the skills that match the weaknesses of their CEO. ¿Right? Maybe it's a CEO who needs someone to run finance. That's a weakness of mine. Maybe it's one. So you have to have the right skills, you have to match the culture, you have to match the CEO. It's a really tough role to hire.
For so that segues into the bulk of today's interview. ¿What inspired you to start what is the COO Alliance for our folks who don't know? ¿And what inspired you to start it?
Yeah, The COO Alliance is a network and a community of seconding commands from all over the world. We've got members from seventeen countries we've been meeting for six years. Now, we have one monthly event and every month of the year for three hours online. And then we do two in person events that are two and a half day events. The next one's being held at MIT. And these coos typically about forty million in size, but they need at least five million to qualify for being a member and they can be any title. It could be a COO VP operations as long as they're the second in command of the CEO. So that's what it is. The reason that I started. It was, I actually had three clients that I was coaching and their coos asked me if I would pull together a group of coos of my coaching clients so they could actually get to know each other and brainstorm. And I threw up a one page, landing page and said, for six thousand, seven hundred bucks, you can come and hang out for three days. Twenty five hours later, we had twenty or eleven people signed up to come. So right out of the gate, we knew we had a model. And then, after that three day event where all we did was share war stories with each other and do presentations to each other. Nine of the ten of them wanted to continue meeting. So we knew we had the right model, the right market fit the right price point.
Congratulations on that again. Another successful venture. ¿Why do you think it is that the COO position is so hard to hire for and so hard to keep the right to keep it successful?
¿It'S hard to hire because the CEO really needs to know themselves first, Right? They need to really own it. ¿What are their own personal strengths, What are their weaknesses in terms of the business day to day? ¿What are the areas of the business that feed them with energy, What are the areas of the business that drain them of energy and then what really needs to get done over the next one to three years And can they find the right person who's done it before, who matches their behaviors, who kind of is a good yin and yang fit for them as the CEO and who matches the rest of the leadership team and who wants to come in and do it for the right comp? So you've got all these little pieces that are very, very difficult. ¿What's different from the COO position versus, let's say, the head of finance? If you're the head of finance, you can be the head of finance for most companies. If you're the head of marketing, you can be the head of marketing for most companies. The head of it, the head of engineering, the head of customer engagement, the head of HR. But the COO is literally completely different in every single company. That's why it's tough.
Amen to that. Now, Brian had to figure out and decide on his and come up with the assessment that you weren't the right guy to go from, let's say, one hundred to four hundred million. ¿How do we, as a CEO, as a company founder, become aware of where we are, what season we're in, what skill sets we need to compensate for? Because I love in the book that you're talking about you, you don't want to hire someone whose strengths match yours to be your COO. We're specifically hopefully trying to hire someone to complement our weaknesses. ¿Did I get that? Right.
Exactly. Now, so what Brian started to notice was the things that made me strong in the first six years were things like I was very entrepreneurial. I could literally make it up on the fly and make decisions very quickly. And I could draw on my experience of having built a couple of other franchise organizations. And I was very good at attracting people, retaining people and growing people. All of those and starting departments. All of those things were really, really good when we get to the hundred million mark. I had to be strong at matrix decision making which I wasn't. I had to be much stronger at leading much more senior people which I wasn't. I had to slow down things and get more people involved in decisions because we had to be a little bit more strategic with our decisions. We were operating in four countries, in three hundred, thirty cities, thirteen operating P. And LS. ¿You can't be that entrepreneurial? Make it up on the fly and tell people what you're doing as you're running down the hallway. You need to kind of. And I wasn't good at slowing it down. I also needed to become more corporate in a way. And I really wasn't corporate. I was very entrepreneurial for him. ¿He needed somebody with that new set of skills so that they could take the company to the next level so that he could continue to be him, right? Continue to be culture, continue to be vision, continue to be plugged into what was happening in the market and with growth. But really needed a different person to actually scale it.
¿How do we and CEO's and SEO's we grow and evolve over time, right? You talk about investing in your personal growth and personal development. ¿All the masterminds, for example, that you and I have been a part of how do we as a CEO identify what we need help with now? ¿And how do we find someone whose skill sets match what we're needing assistance with?
You know, it's interesting that you mentioned some of the masterminds. I think you and I first met at the Genius Network maybe eight or nine years ago. I remember sitting chatting with you at lunch one day and by CEO's plugging themselves into those communities and networking with other CEO's. And I think every CEO, by the way, should be a member of two mastermind groups. ¿Because it's kind of like ideas having sex, right? If you're just in one all the time, it's the same people circulating the same ideas. But when you take ideas from two very disparate groups, those ideas spawn into something else. ¿So by having discussions with other CEO's about their COO, you get to understand, well, how are you working with your second in command? ¿How are you having date night? ¿How are you structuring your meetings? ¿What's driving you crazy? ¿What have you benefited from in terms of communication? You start to learn. ¿And that's really what we do in a lot of our COO alliance events is we get all these coos to talk about how do they make their CEO look good, How do they help their CEO become iconic? ¿How do they help save their CEO from themselves? In many cases, the coo is almost the leash to the CEO Dragon or the breaks to the CEO's gas. I've always said that our job is to save the CEO from themselves at times, especially the very entrepreneurial CEO. So I think if you plug yourselves into these communities, you learn more about yourself. You also realize the more that you can start delegating and getting off your plate of things that you might be good at. But drain you of energy that allows you to spend time in your unique ability, it allows you to work in your area of genius. That's going to propel your company. But if you're working in the day to day on stuff, that's a grind on stuff, that's tough. You end up bringing negative energy to the rest of your business day, the rest of your week, it doesn't fuel your company. The other thing that I think happens if you're in a smaller company, Let's say you're at, like about the five million dollar mark. Most entrepreneurs start a company for only one of three reasons. ¿To give us cash, to give us free time, or to actually kind of put a stake in the ground and say, we did it like, look, ma, you know, no hands, I'm success, right? ¿Because in school, we were all idiots, right? So we're still trying to say, hey, I'm smart. But once we built it, once you get to the five million, you know you've done it and you probably got enough cash coming in. The real other reason why you can bring on that coo is to free up your time. So you can have a life to give somebody else the ability to start building your company for you to free up time. So you can have more time, so that you can take vacations, so you can enjoy your life, so you can work your inherit of unique ability. And guess what they're going to offset their own costs because they're scaling the company so quickly. You're actually going to be able to pay for themselves probably within a year as well.
Anyway, you talk. I want everybody to get the book second in command. But you talk. I thought one of the things that was fascinating is you talk about the different roles, and sometimes multiple roles that a coo can play in relation to their CEO. I want people to read it in the book. But can you just give a couple examples to kind of tease them as to what the type different types of roles that COO might need to play at different times.
Yeah, and I'm actually going to preface that as well with the reason I called the book. The second in command is because your second in command might be a president. It might be a COO. Maybe it's a VP of operations. Maybe it's a Director of Operations or a project manager. Your second in command doesn't have to have the COO title. So let's say that you do, though have that COO or that second in command. Harvard wrote an article years ago called The Misunderstood Role of the COO, and they identified seven distinct types of chief operating officers. So you have the executor, the person who comes in to get shit done. Maybe it's somebody there who's helping you pivot the organization or take in a completely different direction, and you need somebody to help you get it done. Maybe it's the other half, a person that can help you divide and conquer to free up your time as we talked about to work in your unique ability. Maybe it's a partner role, a person who really is there with a shared mindset and so much implicit trust that you can literally rely on them for everything. That was a little bit of what Brian and I had because he was my best man at my wedding three months before I joined him. We had such a huge degree of trust and he'd seen me build two other companies that it was literally. It was almost like a breath of fresh air that he knew there was someone there seasoned enough who he could really count on as that kind of partner to help them scale. The other one is the MVP, that most valuable player internally in the company. That's somebody that you know that if you don't give them a more senior role, they're probably going to quit. So you need to handcuff them to the organization. You have the person who is the heir apparent, the person who is clearly going to become the CEO at some point where one of our founding members, a guy named Matt Wool, was the second in command of the company called Acceleration Partners. After two years, he moved into the CEO role, and then Bob Glazier, the CEO, moved into the chairman role. Another one of our members, Zach Morrison at Genuity, did exactly the same thing. They were absolutely the heir apparents. So those are the different styles of coos that you can have inside of the company.
And obviously there's more in the book. ¿What do you think? The biggest mistake, one of the couple of the biggest, biggest mistakes we're making as business owners and CEO's when it comes to our second in command.
One is to not give them enough time. One is to think, okay, they're really good, they're really solid. I'll just let them do the job. That abdication or walking away from some of that day to day can actually really, really hurt. Often, what the person really needs is your time. ¿They need date night, right? They need it's almost like a husband and wife building a traditional family. Need time away from the kids. They need time to go on vacation together. They need time just to have fun away from the stress of the day to day. The CEO needs to give that time to the COO. Regular meetings, fun outside of the office. I remember when I was the second in command for an auto body collision, repair franchise. I said to the CEO, right at the very beginning when we were starting it off, I want a half hour meeting with you every Monday. And Terry's like, oh, I don't need that. I'm like, no, no, this isn't for you. I need time with you to bounce ideas, pick your brain, stay on the same page, stay in sync. We're not even in the same office. ¿I just gotta, like, Gonna be our water cooler time, right? So that's one second is that the CEO's often don't clarify the vision of where they're going. So I call it a vivid vision document that if you can get your team on the same page as you, that's really powerful. But if the COO is not completely aware of where the CEO wants to take the company, what it looks like, what it feels like, then they're usually bobbing and weaving, trying to make decisions along the way, and that usually gets in their way. Then I think the third is probably to have that implicit trust. I had a CEO one time he said, i just hired a second in command, it'll take me about ninety days to know if I've got the right person. I said, well, that means you suck at interviewing. You should never have hired that person until you knew everything about them. You need to know on day one enough information about that person that you're willing to give them the keys to your office. You know, your bank account, passwords, your passwords for all your software. You should let them take your spouse on vacation like you need to know. So much about this person that the trust is completely implied because they are going to be running your company for you. So I think that would be the third one is not trusting or understanding the person enough that you can trust them.
You've achieved so much success in so many different venues. ¿What's your biggest challenge now.
On business or personal business? ¿Biggest challenge? ¿I think it's always marketing, right? It's staying ahead of the curve. ¿And what's happening with marketing? We're in a strange time right now where I think we're technically in a period of almost stagflation where we've got a bit of recession happening with inflation. ¿So it's where do you spend your marketing dollars and how do you attract the right people? I'm becoming more and more convinced that our marketing has to be into running really great events with really great speakers. So that our members just love it and stay and renew and refer, you know, versus marketing. I think marketing is probably the big challenge.
Your passion is obvious. ¿What do you like best about what you're doing now?
Well, I've really designed it. So I'd say, it's not what I'm doing. It's how did I design my life to be able to have this happening my wife and I decided two years ago to just start traveling the world. So we sold everything and we've been full time on the road. I'm talking to you right now from Spain. Tomorrow we leave and we head off to Iceland. In two weeks I'll be up in Alaska with my two kids. So we're constantly on the road and traveling and exploring the world. And I like that I've been able to design businesses that fit into that. So that I can have a life first and time with my spouse and my kids and my friends and myself and still run really great businesses that really serve a great need.
That is absolutely incredible. We know your time is incredibly valuable. We appreciate you spending it with us while you're overseas for our folks watching and listening who want to learn more. ¿Where is the best place for them to go to learn more about you? ¿And where is the best place you want them to go to get the book?
Yeah. All of my books, including the second command are available on Amazon, Audible and iTunes. And Love to get some more reviews. When you read them, please leave reviews. They should definitely check out the Coo alliance and then also check out a new company that I just launched called the op spot. ¿And that's for anybody in your company that works in any operations roles? The director of ops or ops manager, VP operations. Great place to put those people to grow their skills. I've always believed that the more we grow the skills of our people, the more they'll grow our company and then, lastly, my course invest in youn leaders. It's called investinyourleaders. Dot Com is all of the core skills that I've used to grow the leadership teams on all of our companies in the past. It's kind of a giveaway to get your people involved in that too.
Awesome. Well, we greatly appreciate your time again. We know it's incredibly valuable. This has been Seth Green for sharkpreneur with Cameron. Harold Cameron. Thanks again for joining us.
Of course, man. I appreciate it. Good to see you.
Good to see you. Thanks. ¿Everybody for watching or listening? We will talk to you or soon you need money to fund your idea, product or service. ¿Are you ready to take your business to the next level, but need capital.
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