Cameron Herold was fired as COO by his best friend and company founder when the business hit $100 million and needed different skills to reach $1 billion. He explains his revenue-doubling rule: senior leaders typically stay effective for two doublings before needing a new skill set. Trust was slowly rebuilt through public acknowledgment, though the hurt lingered.
Chapters
I was in an unhealthy relationship with work where the business was my brand, the business was my everything. I had nothing else to talk about other than it was a very unhealthy relationship I had with building a business. It was hard for me to rip myself away from that, to even know who I was. And I think there was a real primal hurt there. And then for Brian, he'd also taken off his left arm and said, oh, fuck, now what am I supposed to do? So we had a leadership team meeting every single Thursday. For an hour and a half to discuss strategy and go through the numbers together. And the meeting would start at 8:00. Brian and I every week on the Thursday would meet at 7:00 for he and I to get in sync before the leadership team would then mink. So we got together at 7:00. We were meeting at the Vancouver Club and I ordered my traditional Eggs Benedict. I weighed 40 pounds heavier than I do today. And Brian ordered a grapefruit. And I'm like, the fuck are you doing ordering a grapefruit? You've never ordered grapefruit in your life. Like, you, you're like Eggs Benny with extra sauce, like grapefruit. And he just looked at me and he started to cry. And I'm like, oh shit, I told your assistant last night you were going to fire me today. I go, what's up? And he goes, I'm sorry, it's over. And he said, you were the right guy to get us to $100 million, but you're not the guy to take us from $100 million to the billion. You're the entrepreneurial COO and I need more of the corporate COO. So it took 12 months for them to find my replacement. They brought in the former president of Starbucks USA. She'd run all North American operations. For Starbucks, she came in to replace me. She came in and said, wow, what a cute little company. And I was fucking pulling my hair out because it was big. I was crying so hard that Brian made me take a taxi home and he drove my car home because I was dysfunctional. It took me at least 4 years to trust him after that. And it was because of the way that it was done. And we've talked publicly about this. When he wrote his book, his first book, Willing to Fail, I was like, I hope he just mentions me. And it was, you know, page 3 I was mentioned, then page 12. I think it was like 7 or 8 times in the book, and he never mentioned anyone from the leadership team, which I thought was weird, but I also really saw how much he valued me. So that's what started to rebuild our trust. There's some other things that had happened behind the scenes with him that had broken his trust of me, that he'd done. So there was some stuff happening that was, that's never been talked about. That he knows and, and knows why there was some things happening. Here's how weird it was. So not only was I let go by my best friend, but 4 days later he asked me if I would go on stage to speak at an event because he was busy trying to figure out how to replace me and asked if I could go speak to 400 people in a slot that he'd been booked for. And then 4 months later he called me to say, can you go speak at another big event? That like, so I was there speaking on behalf of the company even though I was still going like Fuck you, why did you do it this way? This doesn't make any sense. And then for him, he also had to go through these struggles. We were texting last week, like we're really close friends now. But it was just a hard thing, and partially it was because I was in an unhealthy relationship with work where the business was my brand, the business was my everything. I mean, Shelby, when I met you, it was back in the Got Junk days, right? And I had nothing else to talk about other than, it was a very unhealthy relationship I had with building a business. So I think it was hard for me to rip myself away from that. To even know who I was. And I think there was a real primal hurt there. And then for Brian, he'd also taken off his left arm and said, "Oh, fuck, now what am I supposed to do?" Like, in the book, when you read it, he gave so much credit for the fact that he never could have even built it had I not been there. So I think it was hard for him knowing that he'd let his best friend go for probably the right reasons, but the board really mismanaged it in the way to do it. I went into the company a week later to actually read out a resignation and say goodbye to everybody. And so It was this really weird, you know, thing. Yes, I have a group coaching program for CEOs. And the beauty of my group coaching calls is you actually get to ask me questions on every call. You're not just listening to other CEOs. Drop me an email, cameron@cameronherold.com for more information. I actually write about it in my book, The Second in Command. The last chapter is called When the Party's Over, because at the end of the day, in fact, I was in this room about 5 years ago with Clay Mask from Infusionsoft, and we were talking about how long a mid to senior level person can stay in your company. And we both agreed that it was through 2 doubles of revenue. So if you're a $5 million company and you have the head of marketing, the head of marketing can probably be your head of marketing at $10 million. They can probably be your head of marketing at $20 million, but there's no way they can still be your head of marketing at $40 million from a $5 million company unless they're really upleveling their skills. So I was the last person on this whole leadership team of 5 people to be replaced over the 6-year period. So it was the right thing. And I just talk about it in the book as to how to do it in the right way. I knew that it was done. I literally told Brian's assistant Christina the night before, I'm like, I think Brian's gonna fire me tomorrow. She's like, shut up, go home, you're an idiot. Like, we'll see you in the morning. And then I always took a different path out. It's 60,000 square feet. So I was walking out of the business in this weird direction. And Helen, our head of HR, was sitting filling out some paperwork in a boardroom. And as I went to say goodbye, she turned the paperwork over and I'm like, I'm totally getting fired tomorrow. Like, no one had ever turned over paper. I was a fucking COO. You don't turnover paper. So I knew it was coming. I knew it was wrong, and I knew I was the wrong guy to scale it. There's a good way and a bad way to do things, and it just wasn't done well.
