In this candid interview, Cameron Herold and guest Tommy explore the danger of equating a business with one’s personal identity. They discuss how many entrepreneurs chase accomplishment, money, and freedom, only to feel empty once those goals are met, citing Gino Wickman’s post‑EOS burnout and his book Shine as an example. Tommy shares his own overwhelm juggling multiple ventures, family commitments, and the pressure to constantly perform. Cameron reflects on his own stage of wealth—living tax‑free in Dubai, having visited 79 countries, and no longer needing more money—prompting a shift toward downshifting, cultivating hobbies, travel, and deeper relationships with his son. Both emphasize that when work becomes the sole source of dopamine, it masks a loss of purpose and personal passions. The conversation underscores the importance of intentional hobbies, family time, and redefining meaning beyond business success. At the end, Cameron offers a free copy of his book The Second in Command to qualifying COOs and CEOs, reinforcing his mission to help leaders build sustainable companies while preserving personal fulfillment.
Chapters
When people say business is my passion or business is my hobby, then I don't want to hear about your hobby because I don't want to hear a lawyer talk about law and I don't want to hear an insurance salesman talk about insurance and I don't want to hear a dentist talk about cleaning teeth. I certainly don't want to hear you talk about building garage doors. I'm trying to find all the things that fill me. Oh, and yes, I help entrepreneurs make their dreams happen. But when somebody comes to me and go, what do you do? Do you know what I say? I travel, I hike, I cook, I go to festivals, I listen to music. They're like, oh, I meant to make money. Oh yeah, I don't talk about that.
There's 2 things that I wanted to talk about. Number one is Gino Wickman. You know, he sold EOS, or at least 87%, and he woke up feeling empty. And there's a great book that kind of hits home with me, A Man's Search for Meaning. And this idea of like, you know, we keep climbing, but there's no finish line. And even when we hit that finish line, the goalpost has moved. I mean, I don't care if it's body fat, I don't care if it's how spiritual we are. It could be overwhelming at times. And I'll tell you, there's one day a month that I get to this field and it's not like I'm burnt out. It's not that I'm— what I realized my hardest thing is I've got all these different teams on top of A1. You got the family office. I'm getting married, building 2 houses. I've got a lot of 3 software. Like there's a lot of irons in the fire and they all need different types of communication.
Mm-hmm.
In fact, one of my teams said, we don't think you understand how much we— how hard we work. And I said, well, my people, when something doesn't work like our scorecards perfectly, I get 50 people a day calling me and they don't sugarcoat it. So if you need me to sugarcoat it to you, I'm just a translator. I'm delivering the message that 50 people called me today. I'd say I'm happy but never satisfied is the best way to describe it.
Yeah.
And so, and Gino said, I woke up and I lost my meaning. And that's why he wrote the book Shine. But what is it like? Like, what's it— and it feels like something's wrong, but it's actually a good thing. But what are your thoughts on that?
I think there's a societal pressure that we're growing up with that we're trying to drive towards something and we don't stop and ask ourselves why. I think entrepreneurs only start a company for one of 3 reasons, either to have a feeling of accomplishment, right? That success that I did it, to have money and to have free time. At some point when you can check those boxes, you have to ask yourself why we're doing this. you know, what is that real reason? Because again, at the end of the day, we are going to die. So what do we want our life to be? What do we want our meaning to be? How do we want to enjoy this journey? And is it really going to work every day? So I'm at this stage right now where I finally have enough money that I'll never be able to spend it all before I die. I won't be able to spend every, every bit of money that I've got. I live in an economic free zone. I don't pay tax anymore. So now my money's really growing. So I'm a resident of Dubai. I don't pay personal tax or like, so What— so I don't need more money. I have the feeling of accomplishment. I've already built all these companies. I've been paid to speak in 29 countries. I got paid to speak on every continent, including Antarctica. So there's no reason to, to feel the praise or pride of doing it anymore. So I'm actually looking at how do I downshift? What is it going to be about? So I'm really looking at my hobbies now. I'm really thinking about what are my passions. I'm really thinking about where do I want to grow personally. I'm really thinking about what parts of the world do I want to explore. So I have a long bucket list. I have a long travel list I was just working on again the other day with countries that I want to go spend time in. I know how many countries I've been to. 79 countries now. I want to get to about 120 of the 193. So I'm really thinking about that stuff. I'm not going to spend my entire life chasing something that doesn't really matter. All right. If you're the COO of a company that does at least $2 million or greater in revenue, or you're the CEO of a company and you're in the United States or Canada, if you would like a copy of my book, The Second in Command for free, go to cooalliance.com/freebook. That's cooalliance.com/freebook. And I will mail you a copy for free. I will even cover the shipping. Jump on that one today.
Well, let me ask you this. This is what's interesting is I got a buddy of mine who's Service Champions. His name's Leland Smith, 2 beautiful daughters. And he'd go in every Saturday and Sunday. Sunday, no one else was there. And when I really talked to him, he goes, dude, this is my passion.
No, like, it's his passion because he doesn't have other passions that fill him, right? He's lost the relationship with his wife. He's lost the relationship with his kids. He's lost the relationship with himself. He doesn't have the same hobbies and passions that he had as a kid. And because of that, the only thing that feeds him and gives him the dopamine is showing up at work. So when people say business is my passion, Or business is my hobby, then I don't want to hear about your hobby because I don't want to hear a lawyer talk about law and I don't want to hear an insurance salesman talk about insurance and I don't want to hear a dentist talk about cleaning teeth. I certainly don't want to hear you talk about building garage doors.
Well, Damon John, I'm out with Joe and I'm out with him. And I said, do you ever get sick of it? Like people just coming up to you? And he goes, Tommy, I don't have to sing a song like Madonna, like their favorite song. When someone comes up to me, I get to influence their life as an entrepreneur and help them build a culture within the community and raise their family, cut that generational curse. And he said so. And by the way, what I realized is he's on the road. He's probably— and I don't know this, he never told me this, so I don't want to, I don't want to imply this, but I don't think his relationships is perfect with his kids or his wife.
Correct. And mine is like, I am so— like last week when I was in Montreal with my son who goes to school in Montreal, running his own business, he just ran his second marathon, ran a 3:35 marathon. He and I played padel twice. It's kind of like pickleball, but a little more— it's like squash and tennis combined. I had so much fun playing with my kid, going out for dinners with my kid, hiking up Mount Royal with my kid. I'm trying to find all the things that fill me. Oh, and yes, I help entrepreneurs make their dreams happen. But when somebody comes to me and go, what do you do? Do you know what I say? I travel, I hike, I cook, I go to festivals, I listen to music. They're like, oh, I meant to make money. Oh yeah, I don't talk about that.
Oh.
I actually wanna talk about what matters to me, not what I do to make money.
Do you wanna watch this?
I'm passionate about what I do to make money, but it's not my purpose.
