Ep. 213 – The Power Of A Second In Command With Vision

In today’s episode, we feature a special appearance of Cameron Herold on The Greatness Machine with Darius podcast. Cameron discusses with Darius the power of a second in command with vision, as one of the most vital aspects of choosing the right fit for your second in command. 

Cameron offers up several key traits to look for that can save you a lot of time and money. Make sure to take notes and also subscribe to Darius’ podcast – The Greatness Machine. 

In This Conversation We Discuss:

  • Understanding your why 
  • The big traits that are necessary to push a business forward
  • Why every business needs a Vivid Vision® 
  • How important core values play in leadership 
  • The most common struggles many entrepreneurs deal with 


Check out The Greatness Machine with Darius: Click here to listen 

Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book: The Second in Command – Unleash the Power of Your COO

Subscribe to our YouTube channel – Second in Command Podcast on YouTube

Get Cameron’s online course – Invest In Your Leaders

We’re blessed to have Cameron on the show. I’m so happy to have you share your work. 

Darius, this is amazing. By the way, you were a part of what is the best class to come out of the EMP program. It used to be called Birthing of Giants. It’s now called the Entrepreneurial Master’s Program. Brian Brault was your facilitator, right?

It’s Jeffrey Calibaba. It was Verne and halfway through, Jeff came in.

Got it. You were part of a different class, so you weren’t the best class. You’re a good one though. Sorry.

We had Andy Bailey, John Ratliff, and Ken Sim. 

You guys had a great class. I remember where you and Andy Bailey were sitting right by the rail. Ken Sim was one of my first coaching clients. You guys had a good class.

It was an experience. For me, it planted the seeds for what became my life’s work at this point, which is building companies and doing it with the use of core values. Now, I have the book coming out. We met there and you came back for my year three. We then connected a bit after that, but you’re the person that introduced me to TED and got me into that world. That was so formative to me that I based this show on how I produced my TEDx Talk or TEDx program. 

Thank you. Not only did we talk about it at TED, but you’ve been to the main TED. We connected that one year and it’s an amazing organization.

It’s a special thing. It has inspired me to change a lot of the things in my life for the better. You were the bridge for that for me. One of the coolest things for me is to be able to get to spend time with friends. When I came up with the idea for the show a few years ago, I said that the Greatness Machine is all around people who have lived their passions to greatness, and it’s hard to do that. A lot of people like to be asleep at the wheel or get focused on something more traditional. There are people out there that are change-makers that are always pushing themselves. I respect you and consider that you’re one of those people. I’m grateful to have you here. 

For me, this is going to go back way before. One of the top three TED Talks of all time was Simon Sinek. What a lot of people don’t know is Simon flew out to Vancouver to meet me in 2003. Five years before his famous TED Talk, he came out to find out if Brian and I were real because he read about us in Fortune Magazine. Simon came out and we spent a full day together and he was drawing his ideas for what became four and a half or five years later the book, Start With Why. Simon was on our board of directors at 1-800-GOT-JUNK? for a year and a half. He spoke at our conference and help us with our marketing way before anyone had ever heard of him.

SIC 213 | Second In Command

Start with Why: How Great Leaders Inspire Everyone to Take Action

I was trying to get Simon into a speaker’s bureau to cover him and they wouldn’t talk to him because he didn’t have a book. They magically missed out on an amazing speaker and business mind. I got exposed to this whole concept of your why or your core purpose, and understanding your why. What I’ve always loved to do is help entrepreneurs make their dreams happen. I learned that at College Pro Painters when I was coaching franchisees, then building all the companies I’ve built as a second in command, and then coaching CEOs. Everything I do is consistent with my why. That’s what helps me live my greatness. It’s understanding why I get up in the morning.

A lot of our audience are entrepreneurs and you’re in their world. In the entrepreneurial world, you’re a known entity. For those that are not entrepreneurs and this is their first time meeting you, do you mind maybe giving a little bit of background on your entrepreneurial experience, and how you got into what you’re now into? 

I was groomed as an entrepreneur. My dad raised my brother, my sister, and myself all to be entrepreneurs. We’ve all run our own companies for between 15 and 25 years. All I’ve ever known was being an entrepreneur. When I was 21, I had 12 full-time employees in my company. I was running a business when I was in second-year university. I ran a business for three years and then when I graduated from school, I had no debt. I bought a house and started coaching entrepreneurs.

I started coaching entrepreneurs in 1989 before coaching was a thing. I was with an organization called College Pro Painters, where we had 800 franchisees every year that we had to coach, train, hire, and recruit. In 1993, I recruited Kimball Musk, who was Elon’s brother to be a franchisee for me and also his cousin Peter Rive, who built SolarCity. They both worked for me back in ’93. I ended up being a reference for Elon in January of ’95 for his first company, Zip2. I was a reference for their funding round when they only had one employee.

I then went on and co-founded a chain of autobody collision repair shops. In Canada, it’s known as Boyd Autobody. In the US, it’s known as Gerber Auto Collision. We built that up to be now the world’s largest collision repair chain. I left there after four and a half years. I was hired as the president of a private currency company. It was called UBarter.com, similar to what Bitcoin is doing. We were doing it from 1998 through 2000. We sold the company in 2000 for $64 million.

I then left and became the second in command of a small garbage company. It was called the Rubbish Boys. They had changed the name over to 1-800-GOT-JUNK? and I came in as the 14th employee. I came in as the Chief Operating Officer. When I left six and a half years later, we had 3,100 employees system-wide. We ranked as the number two company in Canada to work for. We were operating in 330 cities in 4 countries. We had no debt. We had given up no equity. We generated 5,200 stories about our company and the media. This was prior to social media even existing. We took that company from $2 million to $106 million.

I left there fourteen years ago and started coaching entrepreneurs. My dad called me semi-retarded as I didn’t want to grow an operational company. I just wanted to kick back and I started coaching entrepreneurs. Some of the ones you know, Razor Suleman who was in your class for a while, and then Ken Sim who built Nurse Next Door. Razor sold this company for over $100 million as well.

I coached a lot of good successful companies. I’ve coached CEOs now in twenty-plus countries. I’ve done paid speaking events in 26 countries on 6 continents. I’ve written five books. A few years ago, I started the only network of its kind in the world for second in commands called the COO of Alliance. I have a podcast called Second in Command Podcast. That’s my bio.

It’s funny, especially with friends like you that have accomplished a lot, I’ve seen it as it’s happened. One thing I realized in doing some research before the show was that I met you a month after you left 1-800-GOT-JUNK? That was June of ’07. I didn’t realize that then. That was not something on my radar. I knew that you had been there. I didn’t realize it was that early. 

Let me give you another part that you might not even know. I was fired from 1-800-GOT-JUNK?

I didn’t know that. 

Brian, my best friend, is still one of my closest friends. We hang out all the time. It took us a couple of years to get through it all, but I was the guy that take them from $2 million to $100 million, but I wasn’t going to be the person to take them from $100 million to $1 billion. He knew that it was time that I had to be replaced. We had finished replacing the rest of the leadership team and it was my turn. That was one of the hardest things for him to ever do and for me.

Two days later, I was speaking at an event on his behalf that he couldn’t go to and then a week later, I was speaking at the EO global event about 1-800-GOT-JUNK? Here I am being let go from the company that I had helped build and I’m still out there as a brand ambassador. Thirteen years later, I’m still out there trumpeting it and written all over his book. There’s more to the story.

It was such a big success. For you to do that says a lot about yourself. This is a values statement more than anything. That’s core values play. You knew what you were good at and what you wanted to do. You then took that and created so much. You’re ridiculous. The way you’ve done it has been so impressive. I appreciate you giving that background.

Because of your exposure to the entrepreneurial ecosystem, both from a visionary and operational standpoint, and the fact that you specialize in working with number twos, but do it in this visionary way, when you’re looking at what’s happening right now in the marketplace and the environment with all these businesses with your clients or the people you’re mentoring and coaching, what are you seeing? What’s front and center for you?

The big thing that’s front and center is that the companies that are doing well are the ones that are led by leaders that are leading. They aren’t worried about what’s happening. They’re focused on a vision, driving towards goals, energizing the team, praising people, and creating momentum. The ones that are struggling are the ones that are stuck, staring at social media, and worried about fear. They’re paralyzed by fear instead of deciding that it’s going to be different. FEAR is the acronym for False Evidence Appearing Real or something like that.

What I’m noticing is that good leaders are leading. In my first book, Double Double, I talked in one of the chapters about how to grow when it’s slow. That was one of the things I talked about. In times of distress, economic downturn, or issues like the pandemic, leaders have to lead because the followers are dying to follow someone. They’re scared.

We talked a little bit when we caught up a few moments ago. You met Simon in 2003. I met him in 2008 or 2009, and I met you in 2007. You were doing the Vivid Vision work then. I’m pretty steeped in the entrepreneurial committee, so people are always like, “Have you ever heard of this book called Vivid Vision?” I’m like, “I’ve heard of it.” “Darius, do you know this thing I learned at our EO chapter, there’s a guy named Cameron Herold?” I’m like, “Yes, I know, Cameron.” It’s funny because you’re so entrenched in the community, I don’t know if someone comes up more than you do, honestly. I don’t know if anyone’s ever told you that, but I’m telling you that right now. You come up all the time from many different directions. 

I’d love to know the bad ones.

No, they’re always good and meaningful. It’s a testament to the work you’re doing. My question for you is how did you come upon the Vivid Vision work? You worked with Simon and his thing was more of a marketing approach to connecting at a higher level. You guys did this at 1-800-GOT-JUNK? Do you mind digging into that a little bit?

We did it before 1-800-GOT-JUNK? Brian’s company was called The Rubbish Boys. My company was UBarter.com. Another friend of ours, Dan, had a company called PadTech. There were 120 entrepreneurs from the EO chapter in Vancouver, which was the first mastermind group that I ever joined. It was called YEO, back in the day, the Young Entrepreneurs Organization. It was the network of entrepreneurs that owned companies doing greater than $1 million in revenue.

We had a monthly lunch event where they were bringing in a speaker who was going to talk about sports psychologists and how high-performance athletes utilized vision. There were 16 of 120 who went to lunch. The 104 were too busy. We went and learned how athletes utilized vision at the highest level to accelerate their performance. The professor was teaching us how athletes could do it, and how we could take that into the business world, get the vision in our mind, and communicate it to employees. He gave us the idea.

We went back to my office later that week, Brian, me, and Dan. We each worked on what we’re calling our painted pictures at the time, now called the Vivid Vision. Brian was writing one for 1-800 GOT-JUNK? I was writing one for the barter company, which we sold two years later. Dan was working on one for PadTech that he still runs now. That’s where we learned the idea.

Over the years, we started communicating it mostly at EO chapters and groups we were asked to speak at. Our growth was happening and getting all this press. We ranked as the number one company in British Columbia two years in a row and then number two in Canada. People wanted to know how we did it. We talked about how we did it. It was around vision, people, meetings, and strategy. We taught the systems and then it took off. That’s where we learned it.

I don’t know if I mentioned it, but I stepped down as the CEO of my company back in November. I was on a podcast early on and the question was something around what’s the biggest regret or toughest thing you ever did. I said, “Stepping away as CEO of my company was tough.” It is a great company. I’m very proud of what I built there and what it continues to be built there. 

It’s a blueprint for a core value-driven organization through and through, but my personal core values were not aligned with what I had been doing for many years. I felt like I needed to move in a different direction. To come to that realization was super hard. The aftermath was when your identity is tied to being in these high-profile roles. When you were at 1-800-GOT-JUNK? and as you built that, there are a lot of identities that got tied to you. You had done that and you were the guy. 

There was so much identity tied to it that I refused to ever have it happen again. I refused to ever let my identity become trapped and wrapped up in a brand. The reason for that is I just wanted to be me. That’s why I never decided to join a coaching group. I just wanted to be Cameron. I helped create it, but we created a cult and it was by design. I wanted something more than a business and a little bit less than a religion. We are in that zone of a cult. Once you’re out of the cult and you look back in, you’re like, “I’m glad to be gone.” It’s also affected me that I’ll never work overtime anymore. I’m done every day at 5:00.

To have those boundaries says a lot about what you learned and where you moved on from there. I appreciate that because I feel like there are a lot of similarities for me. I have an accountability partner and he is one of the most successful people I know. Through the years, I’ve met some successful people. He brought up your book. He’s like, “Have you done your vision?” I said, “I’m going to,” but I haven’t done it because I’m digesting things right now. I said, “I’m trying to get clear on my personal values because I feel like that’s where I went wrong.” It’s not fair for me to create a vision until I’m clear on my values because I don’t want to create a vision based on achieving. I’m a glutton for achievement and that doesn’t necessarily align with my values all the time. 

This is me being a little self-indulgent. You had said this and I’ve been using this. I said, “Cameron said I decoded the core values. If he said it, it’s real,” but I’m proud of that. When you look at businesses doing that, it’s easier to do it for a business than it is to do it for yourself because there’s way more risk for me. If I get it wrong in the business, life goes on. If I get it wrong for myself, I got to live with myself. 

Not only that but when you establish your core values and roll out your vivid vision for yourself to people, you’re the only one to blame when it doesn’t happen. You’re the only one to blame for breaking it. You’re very accountable. In the business world, when you want to grow a great company like a 1-800-GOT-JUNK? or Tesla, you have to obsess about them as if everything depends on them.

SIC 213 | Second In Command

Second In Command: When you establish your core values and roll out your vivid vision for yourself to people, you’re the only one to blame when it doesn’t happen.


Without a question. 

My core values for my company are pretty similar to what my core values would be for me. Delivering what you promise is my first one. That’s easy. Be open and vulnerable. Show respect for everyone. Grow big, act small. That’s the small-town values that I’m never going to let go of and then have some fun. Those are pretty consistent with who I am. I don’t think it’s that hard to put them out there. Most people don’t want to do the work and go, “What do I stand for? What do I believe in?”

Do you think that that’s because it’s easier to be asleep? 

Most people don’t even think about it. Remember that we are operating in a group of people that are already super high-performance. I don’t know what the exact number is, but only 3% of companies are ever doing more than $1 million in revenue. Let alone $100 million in revenue, rank as one of the best companies to work for, or net promoter scores of positive 90. We’re operating at such a high level. I’m in four mastermind groups, and people used to talk about the TED Conference being expensive. It’s the least expensive of the four mastermind groups I’m in.

The main TED Conference is less than Genius Network, War Room, Baby Bathwater, Strategic Coach, and MastermindTalk. I got six different mastermind groups I was in and some for five years. When our peer group is operating at that high of a level, I don’t think it’s hard for us to put core values in place and let them. The average person doesn’t even know what core values are. When you go out and look outside at the average person living out there, it’s a quantum leap for them to even think about that.

That makes an amazing point. You take for granted what you get used to sometimes. You have a higher awareness of this than I maybe do, but I take it for granted. I’m like, “Of course, you got to know your core values, how else do you make decisions?” To your point, the average Joe is not doing that. Going back to what you said earlier in the conversation, that speaks to the power of leadership.

The Guy Kawasaki asked me, “Why is it that every company you coach turned to gold?” I said, “I only touch gold.” I don’t coach crappy companies. Even when you were in the EMP program, I don’t know what it was, but there were probably 8,000 EO members globally and 65 were selected to be in that program a year. You’re operating above the top 1% line.

It’s of no surprise that you would know this stuff, but the 8,000 EO members would be exposed to it, but they’re in the top 1% in the global businesses. You drop down a level to the average company in Austin, San Francisco, or St. Louis. They don’t know this. They’ve never heard of Simon Sinek or TED. I’m amazed still at the number of people that don’t know this because they’re so trapped in either being busy, raising their kids, or watching the NFL game.

This is where I’ve been struggling a lot over the last couple of years, especially now in the United States at least. Right now, there’s a leadership crisis in the world. What I’m saying unapologetically is I believe mission, vision, and value-based organizations will be the leaders for the next ten years in every single industry that there is. I believe that it is necessary for that to happen so that entrepreneurship can become the model for change at the governmental level. 

Something is going to happen at the governmental level because it can’t keep happening as it is now. Social media is going to become our social consciousness. Social media is going to allow the truth and allow a bit of an uprising to demand change. We can’t let the government be run by bureaucrats anymore. There’s too much waste and too many problems. I’ll go on the record of saying this. I don’t like Donald Trump as a human being and as a person. I don’t like how much he lies.

I certainly like a lot of the crop and waste he’s trying to get rid of. I like how fast he’s able to get some people moving. I’m very impressed with a lot of the change but I wish he would do it in a nicer way. I wish he would be a nicer person. If we could have more change like he’s doing with the right core values underpinning it, we could have some stuff happening.

He’s not respecting the old-guard ways and I’d say that too. There’s some stuff he does that I hate and some stuff he does that I like, but I could probably say that about any politician. My issue with him is that I believe leadership starts from the top. I don’t agree with his values. Therefore, no matter what, I can’t support people or leaders whose values I don’t align with.

I could never let anyone work inside my company who treats people the way he treats them. You don’t call people names. We learned that in grade school. Here, we have one of the leaders of one of the leading countries in the free world and he calls everybody that he doesn’t like by some degrading name. It’s not cool.

It’s simple. Leadership starts from the top. 

One of my core values is to show respect for everyone, and that breaks one of my core values.

My number one core value is heart, which is happiness. My second one is love. I’m like, “That’s not love.” My third is the eye of the tiger, which is what we do to protect those that need protection. Are we stepping up to be the voice for the little guy that can’t protect himself? I don’t like bullies. A bully needs to get punched in the mouth. When I see someone bullying, my natural instinct has always been I’m going to punch that guy in the mouth.

When I see this guy bullying, everything in my body is like, “I’m going to sock him in the mouth.” I told somebody on this show. He’s an older guy and if I was standing in front of him and started talking crap to me, I’d be like, “Let’s take this outside.” I’d take it outside with Donald Trump and I would be unapologetic about beating him up. That’s a core value thing for me. I’m staying true to my core values. 

You may want to rework that one.

You’re getting to work with some of these amazing leaders and companies. Right now, we have a leadership crisis governmentally in many places in the world. We have a real health crisis. When you see these things and see that there are some people leading, my question for you is what can those do to emulate the ones that are leading? What are some ways that you see that there is a fix here? 

I don’t. My world is obsessing about great entrepreneurs and entrepreneurial companies. In the vacuum of everything else that’s happening, I can’t worry about it all. The biggest company that I’ve ever coached at the leadership team level is the CEO and the second command of Sprint for eighteen months. They’re the 82nd largest company in the US and I was coaching them. I was out in my sandbox. My world is the entrepreneurial company, so I can’t talk about how we can emulate leaders or how those leaders can change. I can talk about how you can build fantastic company cultures which is my zone.

I appreciate that. Going back in that direction then, with the stuff you’ve been working on, you’ve published, four books now? 

Five books.

I was off by one. I bought three of them. 

My co-author of The Miracle Morning for Entrepreneurs is based in Austin, Hal Elrod.

SIC 213 | Second In Command

The Miracle Morning for Entrepreneurs: Elevate Your SELF to Elevate Your BUSINESS

I’m going to be on his show. 

We co-authored The Miracle Morning for Entrepreneurs together a few years ago.

He’s a friend of a few friends, John Ruhlin. 

I was talking to John. He almost stayed at my house for the next four days.

He’s such a good dude. Do you know Amber Vilhauer? 


You got to connect with her. I’ll make the intro. She’s amazing. He’s a client of hers. He comes up a lot right now. That guy is doing well. Going back to what I was saying before, here you are putting all this great work into the world. You had five books. What’s next for you? What’s next on your conquering list?

Back to your question about why are most people not heart-centered or following core values. If they would read The Miracle Morning for Entrepreneurs and follow the systems that we put in there, they would wake up and start their day differently, and be focused with intention, gratitude, and visualizations. There are so many good things in those books that are powerful. What was your question?

With all the amazing work you’re putting out in the world, what’s the next big thing for you? 

The current focus is the COO Alliance. I’m growing this network for the second in command. There are so many great groups for entrepreneurs, marketers, engineers, and lawyers, but there was never a place for the COO. I have my podcast, the Second in Command Podcast. That’s where we only interview the second in command. We won’t interview the CEO. I had Hal’s assistant on the podcast. I had the second command of Bumble, 15Five, TINYpulse, Cleveland Indians, and Shopify. I have all these great brands and it’s getting behind the scenes with them.

I have two more books that I am working on in the rough content right now. One is on the highs and lows of CEOs. It’s about why we’re bipolar as entrepreneurs and how to ride that bipolar wave more successfully. The second is around the two-in-a-box model of the CEO-COO relationship where we have that peer partnership, and how to leverage off of that role. I am working on those.

The first one, that’s a talk you do too, right? 

The highs and lows of CEOs is a talk that I do. Tim Ferris published it on his blog ten years ago. He loved it and wrote all my content there. He talked about me there. That’s been something I’ve talked about for years. I’ve had a number of entrepreneurs after either reading that chapter in Double Double or hearing me speak at an event on it that have said that I’ve saved their life.

I had a guy walk up to me who was running a $50 million company with $5 million a year in profit, happily married, with three kids, healthy, and involved in his church. He came up to me and said, “You’ve saved my life. For the last six months, I’ve been suicidal. I thought I was going crazy. Now, I realized I’m just an entrepreneur.” He was sobbing and shaking on my shoulder. He’s standing right by the door at Endicott House at EMP where we did that MIT program together. He was standing out the door shaking on my shoulder.

The problem for entrepreneurs is that we are very alone in our fear, insecurities, vulnerabilities, and stress. The fact that we’ve mortgaged everything and have recruited somebody to join our team, even though we’re not sure if we’re going to make it happen. We’re always on that lunatic fringe. People will be like, “I’ve got highs and lows too,” but you don’t have your house mortgaged and didn’t hire somebody away from a company, and not sure if you’re going to be successful. You’re getting paid every week. I haven’t drawn a salary in a few months.

We are under a magnified amount of pressure. We can’t talk to a lot of people about it. The entrepreneur can’t go tell his employees they’re scared. You can’t go tell your accountant friend or teacher friends because they don’t understand. I talk about that cycle that we go through and how to navigate that cycle successfully.

I do think that there’s something about proving that you’re good enough, and entrepreneurism gives you this tool. A lot of it comes from an achiever mentality. A lot of entrepreneurs I know were athletes or drawn toward sales jobs. It’s things where you get that endorphin shot in the arm that says, “I’m good. I’m the best.” Is there something around self-aggression? Coming from my position, I’m the biggest jerk in the world to me, “I’m not good enough. I better do more. I better build a bigger business.” 

There’s a lot there. I’ll give you an interesting data point. The medical community has nicknamed bipolar disorder the CEO disease. Most entrepreneurial CEOs are on the spectrum for medication for bipolar. Because we’re hardwired, the energy that we carry is why people will quit their job, invest, and follow us. The stress and depression are simply us being too hard on ourselves, not taking a break, and trying to work through it. We don’t understand how to navigate these natural highs and lows. It gets magnified because of the scary world we live in by ourselves.

Many entrepreneurs are trying to get that third-party validation. That’s why they love the press. “Look at me,” What are you doing tomorrow? We were on Oprah, but a week later nobody cared. We’re still getting back up and keep running the business. That is part of it. Because you are heavily identified with the brand, anything that goes wrong or sees that’s wrong with your company, you take it personally. Whereas the reality is none of these matters. We’re all going to die. None of these actually matters.

That’s one of the reasons why having clarity around values and vision is so meaningful. A woman by the name of Monique Rhodes has a business called The 10 Minute Mind. I don’t know if you know her. She’s a New Zealander and she was a friend of mine through Stagen. She said, “Darius, we beat ourselves up when we lose, and we celebrate when we win. Equanimity is about doing neither. It’s about being and experiencing.” I wanted to get your thoughts on this. My mantra that I’m landing on is the win is the path. Getting to be on the path is the win. Do you know Stephen Jagger? 

Yes. He lives 10 or 9 blocks from me.

He was a mate of mine for a hot minute. His younger brother, Kevin spoke at my first TEDx event. He was trying to be a speed skater. His talk was amazing. The name of the show that we did was TEDxGoldenGatePark and the theme was The Pursuit of Passion. His talk was called The Passion of Pursuit. He said, “On my ride over here from SFO to the Young Museum in Golden Gate Park, the cab driver ask me what I do for a living. I answered that I’m a speed skater. The cab driver then said, “Are you an Olympian?'” He said, “That would be like someone asking me what I did for a living and I said, I’m a real estate agent, and them saying, “Are you the number one real estate agent in your country?'” 

He said, “It’s funny that’s where we go with those questions.” He then showed his whole story. He said, “I did this because I wanted to enjoy the process of doing it. Not with the expectation of becoming an Olympian. Maybe it happens, maybe it doesn’t.” I’m sitting there and this is the show that I’m putting on. I spent a year and a half working to curate this thing. I’m like, “I wish I could enjoy the process for something.”

I spent the previous twelve years not enjoying the process, but I always wanted that outcome. I always wanted to win. I spent the next eight years doing it and built an enormous company. At the end of the day, I realized that this is an insatiable appetite. I could be running a $10 billion company and it won’t matter. I will want to run a $100 billion company after that.

It’s a learned wisdom that at some point most entrepreneurs learn. Sometimes it’s from burnout. I was lucky to burn out. I got written about burning out in the Wall Street Journal twenty years ago. I was written up as one of four supernovas whose careers went high and flamed out with stress. I was 34 years old and I was written up as somebody who burned out in their career, but I learned from that. When I met you, I don’t know if you remember, but I weighed 37 pounds more than I weigh now.

You’re way leaner. 

I have this photo with Steve Jagger. He was standing right beside me when I took this photo.

I don’t remember you looking like that.

I was 222 pounds. You look at me now and I’m not weighing 222 pounds. I’m weighing 184.4. At my heaviest, I was 222 pounds. I was standing with Steve Jagger getting that picture at his book launch. That was in 2007 or 2008. I wasn’t a happy dude. I had to burn out a second time to realize and sink in that this is the journey. This isn’t what matters.

I had this discussion with Dean Graziosi, a famous marketer. We were talking about how we want our kids to describe us. When I asked Dean this question, he started to cry. It then got me crying. I said, “When your kids’ friend’s parents say, “What does your dad do?’ How do you want them to describe you?” He goes, “They described me as a good marketer and I’m on the internet. I’m always selling stuff. I have a big company.” I said, “Is that what you want your kids to think of you and to remember you by?” He started to cry. I’m like, “Exactly.”

SIC 213 | Second In Command

Second In Command: When someone asks your kids, “What does your dad do?” how do you want them to describe you?


I’m the same right now. I didn’t want my kids to remember me as a workaholic or somebody who is always working. I want them to describe me as the guy who golfed with them, went hiking with them, made family dinners, and sat down with them. Finished work at 5:00 because I wasn’t trying to catch up because I’m never going to catch up.

I have started to rethink what’s the purpose, and the journey is fun. I enjoy the journey, but getting every project done isn’t the big goal because I’m going to add more projects. I’m already successful. I wrote about this in Double Double ten years ago. I said, “Everything I do from this point forward is a bonus. I’m already there.”

Ten years from now, what’s happening to Cameron Herold in his world? 

I’m fully retired. I’ll be 64. I’m not going to be working. I’ll have enough passive income or investment income that I’m not going to be. I’m going off the grid to start living globally where I’m going to be living in different cities around the world for 1 to 3 months per city. I’m building out the CEO of Alliance, but spending time with friends, traveling the world, and living globally. I could read you the list. I’ve got a list of about 35 cities that I want to live in globally. Probably out of Portugal or Estonia. I’m Canadian, so I can move out of the US tax grabs.

When are you doing this? 

In September of 2021 because my youngest son goes away to university, and my oldest son is already in university. I don’t need to be here. They can come and travel to see me. I can come back to Vancouver once in a while. I want to live in Barcelona, Amsterdam, Paris, Buenos Aires, Santiago, etc.

I don’t know if you’d be willing to do this, but will you send a list to your friends like myself and let me know so I can come and visit you? 

Yes. That’s part of the allure. If I’m living globally, I get to hang out with EO-ers globally. Probably, for that 3 to 5-year period, I’ll still be doing my coaching stuff and running the COO Alliance. My plan is every city that I go to, I connect with the EO and YPO chapter to speak, have that money, and be able to pay the bills for the month or two that I’m there. Everything else is gravy. Everything else gets put into a pot and builds up as my nest egg.

I love that man. You made me smile. I was supposed to be living in Spain right now, but then COVID hit. 

Austin is on my list. Austin is one of the cities I want to live in. I know the area I want to live in and everything.

I can’t wait until you’re here. We got to hang out. 

I will be living in the big black condo tower on Rainey Street. That’s where I’ll be living because I like that little area with little bars and restaurants. I’ll probably be in Austin for a month or two months, but there are too many friends that I want to spend time with and it’s a cool fun area. I’ll be in the same building as Brad Weimert.

I don’t know what month that’ll be that you come up down here. 

I don’t know when Austin will happen because it’ll probably start with Europe first, but Austin is on the list. I’ll send you the list.

I can’t wait to see it. I always like to ask this everybody and I love knowing this about people. If you knew it was going to be your last meal on earth, have you ever thought about what that would be? If you did, what would it be? 

I have thought about it before, but I flipped one thing. I would probably make it because I have this recipe from a Canadian, Rob Feenie, who made these braised beef short ribs that after they cook and cool down, he chops them up, and deglaze a pan. He does them with a little mustard. They glaze up and caramelize. It’s ridiculous. I would serve that with this German spaetzle and cheese dish that I make that is ridiculous and I would open a good bottle of red wine.

I love it. 

Do you like to cook?

I love to cook. 

I will send you the Rob Feenie recipe for braised beef short ribs. It’s about four and a half-hour from start to finish. Take your time and enjoy the process. You get to chill for three hours while it’s in the oven. Let me know what you think.

I would love that. Thank you. What would the red wine be? Do you have a specific red wine?

It would be Burgundy. All roads lead to Burgundy.

A lot of people know where you’re at, but for those that want to learn more about you, what you’re up to, or where they can find you, where would you like to send them to?

All of my five books are available on Amazon, Audible, and iTunes. That’s an easy one. CameronHerold.com is where all of my information can be found and the website for COO Alliance as well.

If you go to Amazon, there’s a ridiculous amount of stuff on there on the book side and the COO Alliance and CameronHerold.com

The guests that we’ve had on the Second in Command Podcast amaze me. When I was starting, I was like, “I hope I can get to ten episodes.” Now, we’re at 112.

I wanted to talk integrator and visionary with you for a little bit, but we’ll save that for another time. What a treat. This is a guilty pleasure for me to do this show because I get to talk to amazing folks like Cameron. This is such a treat to have you on the show, my friend. Thank you so much. 

Thank you, Darius. I appreciate it. I also grabbed the screenshot of you and me talking to send off to Steve Jagger right now too.

He was on the show a couple of weeks ago. Do you know Jeff Booth? 

Yes. The last time I talked to Jeff in person was leaving Mike Jagger’s birthday party at Steve Jagger’s house. Jeff and I walked up the street together.

He’s going to be on the show.

Jeff’s a wonderful guy. He’s one of the best heart-centered entrepreneurs with a super sad story as well on how much time, effort, and energy he put into building the company and then being removed by the board out of their greed. It’s sad.

I was doing some research on him and saw that. I was like, “I know the name of that company. It’s in Gazelle’s case study.” I didn’t even realize. I’m like, “Why does that sound so familiar?” He’s a scaling-up case study. How it came up was Stephen was like, “You need to check out this guy’s book. He’s got this crazy book right now about what’s happening economically in the world.” 

He’s a smart dude. I listened to Jeff Booth on a podcast and I didn’t realize the level of his intelligence. He’s a super smart guy.

I’m an econ guy so I was listening to him and was like, “I want to talk to him.” He’s going to be on the show. I figured you’d know him because you got those tight circles up in Vancouver that you all run in. 

It’s funny that he was at Stephen’s house. I was walking back up the street.

Thank you so much, Cameron. I love you. I appreciate you spending time with us. It warms my heart to have you here.


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