Leveraging Relationships to 10X Your Business with Cameron Herold – EP 118

Interview with Cameron Herold

Rick Sapio

Leveraging Relationships to 10X Your Business with Cameron Herold

Cameron Herold, a.k.a. The “CEO Whisperer,” had 15 businesses by the time he was eighteen and is the mastermind behind 1-800-GOT-JUNK?’s spectacular growth from $2 Million to $106 Million in revenue in just six years.

Cameron is a living embodiment of a person crushing it in business while leading a life full of joy and fulfillment. Eighteen months ago, he and his wife decided to sell all their possessions and travel the world. That not only didn’t harm his financial success, but it also bolstered it even further.

During all this time, Cameron didn’t lose sight of why he became an entrepreneur in the first place… To build the lifestyle of his dreams.

In today’s episode, we discuss why surrounding yourself with smarter people than you is better than any other growth strategy, how establishing sound leadership systems will skyrocket the success of your business, and the ground rules for a successful exit strategy that will benefit all parties involved.

Featured on This Episode: Cameron Herold

✅ What he does: Cameron Herold is a top business consultant, best-selling author, and speaker. He’s the mastermind behind hundreds of companies’ exponential growth and has indirectly touched thousands of businesses through his work. At age 21, he had 14 employees. By 35, he’d helped build his first two 100 Million Dollar companies. By the age of 42, Cameron had engineered 1-800-GOT-JUNK?’s spectacular growth from $2 Million to $106 Million in revenue in just six years. His companies landed over 5,200 media placements in those same six years, including coverage on Oprah. In 2016, he founded COO Alliance, a company designed to support the Second-in-Command, High-Level Leadership Training & Peer Support For COOs, VPs of Operations, GMs, and Presidents Who Run Company-Wide Operations.

💬 Words of wisdom: Being an entrepreneur for me was never about money. It was about the lifestyle and the ability to be where I want when I want.” Cameron Herold

 🔎 Where to find Cameron Herold: Twitter | LinkedIn | Instagram | Facebook

Key Takeaways with Cameron Herold

  • A life of purpose is built upon meaningful experiences, not material possessions.
  • The financial and lifestyle freedom that comes with being an entrepreneur.
  • Tips on raising entrepreneurial kids who will crush it in business and life.
  • Focus on your network to build your net worth. No one gets to the top alone.
  • How Cameron landed the Qatari Royal Family as clients during an airplane ride.
  • How to know whether going to an event or a speaking engagement will be worth your time.
  • Where CEOs get stuck most often and Cameron’s tips for creating bulletproof leadership systems.
  • Why growing the skills of your leadership team is the most effective scaling strategy.
  • We’re not promised tomorrow, so make the best use of today.

Cameron Herold | Why I Love Being An Entrepreneur

Cameron Herold Tweetables

“There are really smart people that are doing really smart things. Just do what they're doing, and it'll get you most of the way.” - @CameronHerold Click To Tweet “Growing your COO, growing the skills of your managers and leadership team, that's what's going to scale the company, not just putting the CEO into their own mastermind group.” - @CameronHerold Click To Tweet


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Read the Full Transcript with Cameron Herold

Justin Donald: What’s up, Cameron? So good to have you on the call.

Cameron Herold: Hey, Justin. Thanks for having me. Nice to see you again.

Justin Donald: Yeah, this is great. Well, we’ve been talking about it for a little while and, you know, I feel like the timing’s always perfect as these things work out. And so, I’m excited to talk life and business and all the cool stuff that you’re up to.

Cameron Herold: Well, I think the last time we talked, our friend, Brad Weimert, had us on the call together and we were drinking tequila. So, thankfully, we’re not drinking tequila right now. I don’t need any in the middle of the week.

Justin Donald: Yeah, that’s right. Yeah, we got some Clase Azul. So, he sent us all these little bottles and we got a chance to kind of have a happy hour toast.

Cameron Herold: Yeah.

Justin Donald: But I think you somehow had a big bottle, not the small bottle, if memory serves me correctly.

Cameron Herold: You have a great memory. So, what happened was, I guess, in the United States, you guys have the half-size bottles like 13 ounces. And in Canada, they can only order the 26 ounces, the 750 ml. So, you guys all had 350 or 375. I had 750. I didn’t know. And people were like, “Yeah, I just finished my bottle.” I’m like, “I got to drink more.” So, I’m like pouring away. I ended up drinking about 17 ounces, which is about 4 ounces more than anybody’s bottle had. And then he told me afterwards. I’m like, “Dude, that is not fair.”

Justin Donald: That’s a classic Brad move. I love it. I think that’s hysterical.

Cameron Herold: Yeah.

Justin Donald: I’m glad it happened to you, not me.

Cameron Herold: Right. That was a good time, though.

Justin Donald: So, you’re doing some really cool stuff in the world. We were just talking before we went live here about the travels that you’re up to, and you said that you literally have been to 20 countries here really recently. I’d love to hear kind of the progression of this, how this happened. You’re empty nesters now. So, I mean, that’s part of it. So, tell us what’s going on because this podcast is about lifestyle first, and I feel like you’re living it.

Cameron Herold: Yeah. We are not only empty nesters, we’re now empty or like empty housers. So, about 18 months ago, my wife and I sold our home in the US, got rid of the home in Vancouver, Canada, sold our cars, got rid of all of our furniture. We have a 5-foot by 10-foot storage locker in Vancouver with some art and we have us about the same size here in Arizona with some business stuff and a couple of containers of like some family heirlooms that we’ll pass down at some point. But that’s it. I have four pairs of shoes, three pairs of pants, a bunch of gray and black t-shirts, three dress shirts. And I could tell you my entire wardrobe. And we’ve been in the last, I think the last 12 months, we’ve been to 22 countries in 2022, and we’ve got a lot more lined up for 2023.

Justin Donald: That’s incredible. So, what are some of the highlights? What are some of the favorites? What do you think like, hey, this is an experience that most people maybe have never considered but should add it to their list?

Cameron Herold: Well, we mentioned our mutual friend, Brad Weimert. We were in Antarctica together a year ago. So, down in Antarctica, a group of CEOs, spectacular adventure being in the Antarctic and seeing all the penguins and the seals and the icebergs and swimming in the Antarctic was amazing. That was pretty spectacular. And then going hiking down in Patagonia was a great experience as well. We were down there for six weeks and then we were over in Bhutan recently. We did a trip over in Bhutan and stayed in the monasteries with these monks and did some meditations and lived with the monks and hiked at 14,000 feet and hung prayer flags. And just being in Bhutan was kind of cool. It’s not a country that you can go to very easily. You need to have permits and passes. They don’t let just tourists in. And again, a small group of about 22 CEOs, that was kind of cool. Estonia was another really random, cool, small country that we were in, and spent three weeks there this summer. So, just all over. It’s been nice.

Justin Donald: That’s really cool. And what are the highlights so far? What do you think is going to be a highlight for 2023?

Cameron Herold: 2023? Well, my wife has always wanted to go to Australia, so we’re going to spend two months in Australia in November, December. I’ve been five times, but I think it’ll be a highlight to be there and living there will be really cool. Going over to Bali, again, she really want to spend some time in Bali. I’ve been before. She’s up to about 38 countries now. I’m at 64 so she’s catching me. But I think Bali will be a highlight being able to live in a very different climate, very different environment. It’s very kind of hipster right now to be in Bali as well. So, I think being around that lifestyle and very much lifestyle entrepreneurs over there will be great. I’d really like to hit, I think South Korea might be on our plan this year, too, but that would be an interesting one. And I think my boys and I are going to go to Colombia together. I’ve got 19 and 21-year-old boys. So, I think Colombia is going to be my June trip with them. And then we’ve got a trip to Iceland planned and that’s going to be epic.

Justin Donald: I love it. Well, we’ve got some stuff lining up here. That’s cool. We’ve got an Iceland trip planned here for 2023 as well. So, maybe our dates line up. That’d be cool.

Cameron Herold: Yeah. We’ll have to share agendas. We’ll be over there in June.

Justin Donald: Yeah. And, you know, we just love Colombia. We’ve been there many times. We had family living there. So, we’ve been to Medellin or as the Americans like to call it, Mede-yin, Cartagena. I mean, it’s just a really cool country. So, I think that’d be a really fun trip for you and your kids.

Cameron Herold: Yeah. I’ve never been. My wife has spent about a month down there a year or two ago and she raved about it. And so, I think that will probably be the switch. Take my kids down there. They wanted to do something in South America, so that would be a good one.

Justin Donald: One of my all-time favorite drinks that you can find on every street corner there are these Coco de Limonadas. And it’s just these coconut lemonades. Sometimes it’s coconut limeades. Actually, it’s more lime than lemon. It just kind of depends but it’s delicious. And then also Bali is super high on our list. That’s where I ended up proposing to my wife. So, it’s a very special place for us and we absolutely adore Bali.

Cameron Herold: Yeah. You’ve got the right idea as well with the whole lifestyle, travel and lifestyle, just like setting things up, right?

Justin Donald: That’s right. I’d like to hit every country at some point in time. I know that some are easier to get to and others are harder and some maybe are not the best to go to in this current economic season or just everything that’s going on. But, man, I just want to explore the world. I want to experience everything, all the cultures, all the people.

Cameron Herold: I just want to see what’s out there and go through the experiences and meet the people and understand the cultures. At the end of the day, none of this matters. We all die. You know, we’re all just walking each other home, so we may as well enjoy the journey.

Justin Donald: That’s right. That’s right. And I’d love to talk about your journey, how you got to where you are. How did you know that you were an entrepreneur? You started out kind of in more of like a corporate role but that corporate role I feel like defined you. Actually, younger, you may have actually been a full-blown entrepreneur, then you transitioned into corporate America, C-suite, right? And then kind of created a business on that.

Cameron Herold: Yeah. So, I was actually groomed as an entrepreneur. I did a talk that’s on the main TED website about it’s called Let’s Raise Kids to Be Entrepreneurs. It’s got a few million views. Still on the main TED website today. I had about 15 different businesses by the time I was 18 years old. When I was 21 years old, 20 or 21, I think I was 20, I had 12 full-time employees in a company that I owned. So, I was in second-year university, ran my own business, had 12 employees way before being an entrepreneur was cool. Like, that was 1986. So, being an entrepreneur was not cool in ’86. We were the greedy capitalists, you know, kind of vilified humans back then. But my dad was an entrepreneur. Both grandparents were entrepreneurs, and he and my grandparent’s mom really kind of groomed my brother and sister and I to all be entrepreneurs, and we’ve all really run our own businesses since then. Brian, who is the founder of 1-800-GOT-JUNK, he and I were in a forum together in the Entrepreneurs’ Organization for four-and-a-half years, and he watched me build two other companies. So, I was a partner in a franchising company for what’s called Gerber Auto Collision in the US, Boyd Autobody in Canada. We built that out. It’s about a $2 billion company. I was one of the three partners in that firm, and then I was hired as the president of a private currency company, and we built that company out and built it and sold it. And then I joined Brian to be his second in command. But there was only 14 employees. It wasn’t a big corporate company at the time. I was employee number 14.

When I left six-and-a-half years later, we had 3,100 employees and I’d been the COO for that journey. But by the time it got corporate, I was pulling my hair out. I was literally going, “This is big. This is overwhelming.” And funny, they actually replaced me with the former president of Starbucks U.S. and when Lonnie came in, she saw the company and went, “What a cute little place.” And I’m like, “F*ck. It’s so big.” Yeah. I was leaning more in the entrepreneur. And then I left there 16 years ago. So, I’ve been running my own business now for the last 16 years, started the COO Alliance, which is a network of second in commands from all over the world about six years ago. I’ve now written six books. I’ve been paid to speak in 27 countries. I’ve been actually paid to speak now on every single continent, including Antarctica. I got paid last year to speak in Antarctica to a maverick group.

Justin Donald: That’s incredible. Well, I mean, what a resume.

Cameron Herold: Well, let me touch on something because I almost forgot. When I was about 16, my dad took me to the golf club and we sat down at about 12:00 and we were getting ready to go out golfing and he started showing me all the people walking into the golf club and he said, “You know, he owns a car dealership and she owns a clothing store and he owns this business and she owns that business.” And there were all these entrepreneurs coming to play golf on a Wednesday at 12:00. And we went off and played golf and we came back and it was 5:00 and we’re sitting on the balcony and I’m eating my fries, you know, with gravy and drinking my cherry coke. And he’s eating his like onion rings and drinking his whatever. And he’s pointing to all these people walking in at 5:00 to play golf and it’s summer. So, the sun sets like 9:30 at night up in Sudbury and he’s like, “He works for a car dealer and he’s a lawyer and she’s a teacher and he’s a dentist and he works for this company.” He said, “Do you remember what all the people did that were here at 12:00?” And I said, “Yeah, they’re entrepreneurs.” And he said, “Do you notice the difference?” And I said, “Yes. If you’re an entrepreneur, you can play golf whenever you want to.” And he said, “That’s why I’m an entrepreneur, so I can do what I want when I want, and I can have the lifestyle and the life that I want and not have to report to somebody else.” Being an entrepreneur for me was never about money. It was about the lifestyle and the ability to be where I want when I want. And it’s always stuck with me. What’s weird is the money always come anyway. Like, by focusing on having a better life, I delegate more. I say no to the wrong things. I say yes to the right things. And somehow it just keeps lining up in the right order for me.

Justin Donald: What a great life lesson at that age, at a young age where we’re at a defining age, young and very open to different things. Like, I feel like so many impactful conversations happened for me in my 18 to 24 age range, you know, maybe even early on, on the sales side of things once I was, what, 14 years old. So, I love hearing that and I’d love to even follow up on that because you had mentioned your TED Talk. And by the way, I thought your TED Talk was incredible. One of the things that was a big takeaway for me from your TED Talk was how you opted not to do allowance but rather decided to find a way to help encourage an entrepreneurial spirit for your kids to be able to make their money. I’d love for you to speak to that.

Cameron Herold: Well, there was two parts to that. One is that’s the way I was raised. So, I was told by my dad, “You’re not getting a f*cking allowance. There’s some sh*t you have to do around the house anyway, so you better do it. And then there are some other things that if you spot the opportunities, we can talk about it and I’ll pay you.” So, I’d be sitting down one day and be like, “Hey, Dad, the backyard needs to be cut.” And he’s like, “Yep.” I’m like, “I’ll do it for five bucks.” “No way, man. I’ll pay you three bucks.” I’ll be like, “How about four?” He’s like, “3.75.” I’m like, “Done.” So, here I am like spotting an opportunity, having a hustle, negotiating with my dad, even in a playful way that I know he’s going to pay me something but then I get to go out and cut the grass and I get the money. What he was teaching me was there’s an endless amount of opportunities if you look for them to make money. Negotiation is not a bad thing. It’s a skill. You have to meet somewhere. Both sides have to meet or you’re never going to get a deal. And an allowance is simply a paycheck that you get the same amount of money every single week and you’re probably going to try to do the minimum amount of work to earn that same amount of money every single week so you’re not going to be opportunistic and look for things. And my dad’s going to have to nag me all the time to go earn my money, right? So, he was teaching us at a very young age to be entrepreneurial, not necessarily to be an entrepreneur yet, but certainly to be entrepreneurial.

And then now doing that with my kids, you know, they wanted money and I’d be like, “I’m not giving you a weekly or monthly check, but look around.” And sometimes they didn’t see the opportunities. So, I’d say, “Look, we have a pear tree. There’s pears all over the backyard. Go pick them up.” And they’d be like, “Okay. How about, you know, whatever?” And we’d have fun with it and then off they’d go. And then there were also other things that were just part of, “No, you live in this household. When I’m telling you to clean the dishes, we don’t get to negotiate with that. That’s called you didn’t see the opportunity. Now, you’re having to do a job.”

Justin Donald: I love it. I just think it’s amazing. And to anyone who is paying an allowance, maybe this is just food for thought. I know each child is a little different but I think the more that we can help foster an entrepreneurial spirit where we can get into discovering things, discovering how to offer value, I think that that’s just really exciting and substantive in today’s day and age. So, I think that’s great. You know, I was thinking about this. You’re earlier talking about being part of EO, Entrepreneurs’ Organization. I know you’ve spoken for them a lot, and I think the first time we actually met was a decade ago when you came to St. Louis. I was living in St. Louis at the time and John Ruhlin, our mutual friend, was like, “You got to come here. This guy speak.” And he’d been trying to get me into EO forever and I didn’t see the big picture of it, didn’t see how it could help me at that time. And so, I went to your message and I was like, “Man, this guy has figured life out. I’ve got a few hacks I’m going to just walk away with here.” And then I heard some of the stories of how John and you connected and what a cool kind of full circle scenario where now we are friends and get a chance to connect and get a chance to share ideas and business concepts. I’ve learned a lot from you over the years and I’m excited to continue to do that.

Cameron Herold: John has become a very, very close friend. Were you involved in Cutco as well?

Justin Donald: I was. I was. That’s how I paid for college.

Cameron Herold: It’s like everybody I meet that got involved with Cutco is amazing. Like, Brad Weimert was Cutco and John Ruhlin is Cutco. My coauthor of the Miracle Morning for Entrepreneurs, Hal Elrod, was Cutco. And you all really have this kind of formulaic, you’re all like nice guys who are entrepreneurial, who show gratitude. And yeah, there’s something that was really cool about it. They either recruited all of the same people or they really gave you some good, grounded skills. Yeah. John and I met through EO and he always was, “I wouldn’t be here where I am in the business world without putting money to joining these different entrepreneur groups I’ve been in.” You know, I was an EO member for five years and I’ve worked with them in 26 countries. I was a Strategic Coach member for seven years. I was a Genius Network member for seven years. I went to my fourth Baby Bathwater event this year. I’ve been to five Mastermind Talks events, a couple of War Room events. Like, I’ve really invested in getting into these networks so that I’m not the smartest person in the room. I’m just in the right room learning from these people and also learning who can help me when I don’t know the hows. Right?

Justin Donald: Yeah, that’s incredible. And by the way, I’d love to even touch base on this more because, I mean, I would totally agree. I would not be where I am today had I not invested in my education, had I not put myself in rooms with people playing the game of life, business, wealth building at a much higher level than I was, to even just open my eyes to what was possible or to glean some strategies periodically that I could copy. You know, I feel like one of my gifts is that I can be a good copycat, you know? I mean, who’s doing it well? And I’ll go copy him.

Cameron Herold: My dad again when I was 16 said that I would never be smart enough to figure it out on my own. And he said, “Your R&D should stand for rip off and duplicate.” There are really smart people that are doing really smart things. Just do what they’re doing and it’ll get you most of the way. Because I wasn’t the smart kid in school. I got a solid 2.3 GPA, maybe 2.4. I can show you my transcript. It’s embarrassing. Oh, I always just look for the cheat sheets.

Justin Donald: I love it. And what a great hack, right? You could go to get your Ph.D., your doctorate or master’s, or you could just hang out with the people that do that and kind of partner up with them and learn all the things that they’re doing. I mean, that really has been where the vast majority of my success has been. And at one point when I wrote my book, I added up that I had spent over $1 million investing in myself in my education, in whether it be masterminds, partnerships, coaching, the best legal advisors. Whoever and whatever it was that was best in class, that’s what I wanted. I know you’ve done the same.

Cameron Herold: It’s funny. I’m just going to make a note to add mine up. I haven’t quantified what it is but I’m going to find out what it is because it’s certainly substantial. It’s interesting. Years ago, I also believe in kind of things happen for a reason, like the synchronicities and karma. Years ago, I was told to go. I was in Santa Monica at a Strategic Coach event and somebody said, “Hey, while you’re there, have lunch with this guy, Eben Pagan.” And I’m like, “Who’s Eben Pagan?” And this was like 20 years ago. So, I go off to have lunch with this Eben Pagan guy who’s now become very, very well-known in business. We had dinner actually. We were eating fish tacos at the James Beach Cafe in Santa Monica. Anyway, over dinner we’re talking about investing, where are we investing our money? And I was like all these stocks and these, you know, funds and real estate, blah, blah. I’m like, “What about you? Where are you investing?” He goes, “I invest in masterminds.” I’m like, “What are you talking about?” And he said, “I will put $250,000 this year into being in the right rooms. I’m going to Necker Island. I’m in the Genius Network.” I’m like, “No, no, we’re talking about investing our money.” He goes, “Oh, I understand.” He goes, “What did you get last year as your return?” I’m like, “15%.” And he goes, “Great. So, you put $250,000 in. You get 15% return. I invest $250,000 in masterminds and I’ll generate $2 million in ideas and revenue.” I’m like, “Teach me. What are you talking about?”

And it was because he knew the right people that he then could do the right business deals or had the right introductions. So, instead of him trying to figure out how to do something, he would get introduced to somebody who could do it for him as a favor or at a discount or even for… Anyway, fast-forwarded my entire business world that one dinner.

Justin Donald: Oh, it’s incredible. And by the way, one of the things that I just was talking about, so I had the privilege of speaking at the Texas Ranger Major League Baseball team stadium. And one of the things that I added up for the audience was how many people I have taken out to lunch, coffee, or dinner over the course of 20 years because I take a lot of pride.

Cameron Herold: It’s weekly, right?

Justin Donald: Huh?

Cameron Herold: Isn’t it you that does it weekly?

Justin Donald: Yeah. Yeah. Every single week I take someone out and I learn from them. I find someone that knows something more than me or different than me, better than me. And I just spend time with them. I’ve been doing it for over 20 years. Some weeks more than one, but at least one unless I’m on vacation.

Cameron Herold: I saw a post that you did about that on Facebook recently, and I was just like, “Pff,” because I’ve hosted dinners for years, probably only quarterly, but where I’ll have 10 or 12 CEOs together and just hold it sometimes at my home and I do it as a potluck like everybody brings food. But I love the whole like just the focus of once a week going and meeting with a smart person, hangout, getting to know each other, and you never know what’s going to happen, but stuff happens.

Justin Donald: Oh, those are relationships. There are so many things that have happened with them. I mean, the expectation was never that. But you never know who you’re going to get close to or what topic you both relate on and maybe it ends up pairing up for something right away. And so, a lot of people wonder how did I kind of make some of my leaps in the business world and entrepreneurship and investing. And I always say it’s the relationships. It’s meeting the right people at the right time, putting myself in proximity with movers and shakers and people that are inspiring and just a heck of a lot smarter than me.

Cameron Herold: I’ll tell you another one that putting yourself in proximity is I only fly business class now. If a flight’s longer than an hour and a half, and not at the ego. I’m 6 foot 4 so it’s a bit of a – my body’s just big. But I have done and I can quantify the dollar figure that I’ve landed in business deals from sitting in business class. I’ll give you two examples. One, I was flying from Vancouver to Phoenix and I’m sitting beside this woman on a plane and, you know, “What do you do? Blah, blah, blah. I’ve written this book and I dabble, dabble.” Oh, she’s like, “I’ve read your book.” I’m like, “Oh, you’re kidding.” I’m like, “What do you do?” She goes, “I’m the second in command for this business group over in Qatar.” I’m like, “Oh, what do you run?” “Oh, we run like some health care and some infrastructure and some schools.” I’m like, “Oh, wow, it’s really big. You know, what’s the company called?” She kind of kept avoiding, and she finally was like, “Well, actually, I’m the second in command for the royal family, for the monarchy that owns the country of Qatar.” I ended up landing them as a client. She paid me $100,000 to fly to Qatar for three days, paid for my first-class flight, paid for my hotels, gave me $100,000, gave me $50,000 upfront to show up to coach them for three days just because I sat beside her on a plane.

Justin Donald: Wow.

Cameron Herold: And then on another flight, I was flying from Chicago to Miami and I end up sitting beside this guy, Marcelo Claure, who ended up selling his company for $1 billion to Softbank, gets appointed the CEO of Sprint. I land him as a coaching client. I coached Marcelo and his second command for 18 months because I’m sitting beside him on a plane.

Justin Donald: Wow.

Cameron Herold: You just meet more successful people sitting in the front four rows than you do sitting in the back of the plane. And it’s nothing against the back. It’s just put yourself in the proximity of those and you’re more relaxed. You show up more relaxed. You can get work done. You know, you save time because you can board late and get off early and, yeah.

Justin Donald: Yeah, that’s an incredible tip. You know, so it’s interesting because I don’t know that I’ve ever thought about it that way but it’s spot on. And I did fly first class back home just today right before. I mean, I literally was scrambling. I’m like, “Please be on time, flight,” because you and I have our podcast and I got back just in time. I didn’t want to have to reschedule. And it was very obvious that there were some pretty successful people in the front there with me. And I probably didn’t take as much time networking the way that I could have or should have. The person next to me slept the whole time. But what an incredible just mindset shift. I like that. I think that’s really cool.

Cameron Herold: You know, it’s joining the right golf club, joining the right tennis club, joining the Soho House, and just being in the rooms. You just put yourself at a strategic advantage to be able to meet the right people and do the right deals. And again, if it’s out of ego, you’re dead in the water, right? If you’re doing it to be somewhere or take a photo with somebody, forget it, it’s over. But if you’re just doing it because you know that you’re going to have a better chance of meeting good people, you better show up as a good person too. You have to show up with the same level of humility and core values and curiosity. Otherwise, you’re just going to get more, “Great. So, you met me on a plane but I wouldn’t talk to you anyway.”

Justin Donald: Yeah, that’s good. That’s powerful. And from the standpoint of mastermind, I mean, some of them are cheaper than others, but overall, they’re not cheap. I mean, this is a real investment. These things range in price from maybe a few thousand dollars on up to, you know, there’s one that I have friends that run one that’s $250,000 to join. You’ve got one that’s $100,000. You got a ton that are out there at 35,000 to 55,000. So, yeah, but if you can figure out how to get a return on those dollars, it’s not about how much is it. Like, I stopped worrying about that a long time ago. It’s what value can I get from it? Can I get more than whatever the number is? It doesn’t matter what the number is. Like, one of the people I paid to coach me was $250,000. My friends told me I was crazy and I said, “What matters is can that coaching produce a greater return or just break even of $250,000 in income,” which it did and it did quickly.

Cameron Herold: Yeah. And if it does, then you got that momentum creates momentum, right?

Justin Donald: That’s right.

Cameron Herold: So, I call it the trifecta. If these three things happen, I’ll say, “Hell, yes,” to going to that event. Number one, can I get ideas on how to grow my company and my clients’ companies? So, am I going to be in a room where I can grab ideas? That’s number one. Number two, can I hang out with current clients or really successful entrepreneurs? That’s number two. Number three is, can I get clients while I’m there without being a sleazy salesperson? If I have to walk around to try to sell my stuff, bad deal, bad group for me, bad group for them, they’re not going to want me there. But if I can be in the room, maybe I’m a speaker, maybe I’m just in the right room and there’s lots of downtime to get to connect and talk and I know the value or the level that they’re at, then it’s a hell yes. And so, I was in Bhutan recently hiking with the monks and staying in these monasteries. And, you know, I paid I think it was $15,000 for my wife and I to be at that plus our airfare so call it $20,000, $25,000. But I’ve landed a coaching client and a COO Alliance member. That’s $85,000 right there. So, I’m like a 3.5X return and I had fun. I was there for like a week in Bhutan hiking and it was amazing and I’ll do that again. So, I’ve signed up with them to go to Uganda and go check out the gorillas in Uganda in June.

Justin Donald: That’s awesome. I love it. Yeah. And it’s really fun when you can go on something, have some sort of business transaction, cover the cost of the event or the travel or the experience, whatever it was. I mean, that’s always just so much fun to do. So, I’d love for you to talk about the COO Alliance because a lot of people kind of, I guess, favor or lean towards things for the founder, the visionary, the first in charge. Talk about what COO Alliance is like and just even having a place where second in command where a chief operating officer can actually go to learn, grow, network with all people in the same field.

Cameron Herold: So, there is a countless amount of groups for entrepreneurs, right? We’ve got YPO, the Young Presidents’ Organization, the Entrepreneurs’ Organization, Vistage, Genius Network, GoBundance, Baby Bathwater, Maverick, like so many groups for entrepreneurs, right? And then recently, I spoke at a conference called the American Society of Association Executives, and it was 7,500 trade associations for groups. There’s groups for doctors and psychiatrists and engineers, auto body shops, and marketers. There’s no groups for second in commands. There’s this whole audience of people that had nowhere to go, and they kept going to the entrepreneur events but they don’t fit in. And I joke about it. It’s kind of like a guy showing up at a baby shower. We’re not meant to be here. Like, sorry, even though it’s 2023, we just don’t fit at a baby shower or a bridal shower. Like, the guy’s not supposed to be at a bridal shower and the woman’s not supposed to be at a bachelor party. They’re supposed to have… Right? Entrepreneurs are supposed to have their events and they don’t fit at the COO Alliance.

So, we don’t even let entrepreneurs join the COO Alliance. It’s a mastermind community, members from 17 countries. We only allow the second in command to join. You have to do at least 5 million in revenue just to qualify. Our biggest member is 1.2 billion and we’ve got about 40% of our members are women. And it’s an event that I don’t teach them. I just facilitated. I could actually hand you the agenda for next week’s event. You could literally moderate the agenda, and all of our members would get just as much value as if I ran it. So, it’s about them connecting with each other. We bring in experts every month for them to listen to and learn from, and then they have their breakouts and group discussions and we run two in-person events a year, one in Scottsdale and one at MIT. That’s it.

Justin Donald: That’s awesome. I love that you do that and I love that you have a place for people that there’s a real need that they can go fulfill, you know, learning and growing with other even more successful COOs. I think it’s great. You know, one of the interesting things for me is I have the Lifestyle Investor Mastermind is kind of how that’s shaking up, who’s coming in, what does that look like? And though we have a lot of entrepreneurs, we definitely have a lot of second in commands. We definitely have a lot of high-income earning professionals, whether it be attorneys, doctors, dentists, you know, people in various different medical fields. And so, it’s really kind of a nice thing because you got someone that kind of specialized, high-income sales professionals. I mean, you got someone in every niche and it’s just neat watching them all kind of hang out, get to know each other. And we’ve definitely recommended many people over your way where we’re like, hey, they could make leaps and bounds for those that are actually COOs.

Cameron Herold: Well, thank you. Thank you. Yeah. You know what’s interesting about when you have like the Lifestyle Investor Mastermind or the COO Alliance Mastermind or even some of these others is because we’re not in the same industry, I call it ideas having sex. You know, you take an idea from a high net-worth lawyer or high net-worth dentist or high net-worth COO or a high net-worth CEO about investing, those ideas percolate and become some other cool things. But if it’s all lawyers in the room, it always falls back to talking about law. Nobody wants to talk about it. After a while, it’s just kind of boring, or certainly, any non-lawyers don’t want to be in that room, right? So, it’s nice that you have that place for them for sure.

Justin Donald: Yeah, it’s fun. So, tell me, you said you’ve written six books. Your sixth one is literally about to drop. And as this episode comes out, it will be out. Tell us about this. So, this one’s really cool because it is called The Second in Command. Right? And this is like, you know, the playbook for COOs. So, I’d love for you to share more on it.

Cameron Herold: Yeah. This is the first book that I actually wrote with any strategic reasoning. My first book was a way to raise my brand awareness and raise my speaking fees. And a couple of mine were a little bit more opportunistic because I had opportunities to write books with Scribe. I was an advisor to Scribe, and they helped me push a few books out and then I co-authored that one with Hal Elrod that did really well. The Second in Command was I kind of realized that I was sitting on all of this IP. You know, I’ve had 245 guests on the Second in Command Podcast. I’ve had hundreds of members of the COO Alliance and I had all these ideas from them and systems from them that was about how do you recruit them and how do you bring them on to your company and how do you build a good relationship with them and how do you get good results from them? And it’s never been codified and there’s not much out there on the subject. You know, again, there’s tons of books written for the entrepreneur, so this is written for both, the entrepreneur and the COO. It’s how do you find one? But then if you are one, how do you find the right company to match for you as well?

Justin Donald: That’s fantastic. Well, coming from someone that has had to play both roles and I know you have two, what a breath of fresh air that there’s an opportunity for entrepreneurs to find how to fill this void and for those that are skilled and qualified here to be able to learn and grow. I’ve been a COO more by need than choice. I have the ability to do it in businesses that I’ve started and that I’ve been involved in. But it is certainly not one of my greater strengths. It’s more like when I get done, I am zapped of energy. It is much better to find someone that this is in their wheelhouse. They get energy from doing this. There’s, you know, things about it that are automatic. So, for me today, when I start projects, when I buy businesses, buy franchises, the first thing I do, even before I buy it, because I get the COO lined up so that way I know that things are going to be in the right shape because I know I should not be in that role.

Cameron Herold: You know, it’s interesting that even if you’re a kind of person that wants to have the good lifestyle, that wants to have balance and be able to spend time with your friends and your family and your hobbies and your spouse, hiring a COO isn’t necessarily because you need it. It could be because you can have one, you know, and then all of a sudden you have this person who can run a lot of your business for you to free up your time, to have a better life, also to free up your time so that you’re only working in a couple of your uniqueability areas that you really love and really feed you with energy. So, it can also really set up the business for an exit too. If you’re ever looking to sell your company, one of the best ways to get a high exit value is to have the team of people running it for you so the company doesn’t rely on you anymore.

Justin Donald: That’s good. Talk more about that. I feel like in my audience, there are a lot of people that are scaling businesses, that have sold businesses that have bought businesses. I’d love to hear you elaborate on that and really the value, right, because people want to buy system-oriented businesses with the people in place that can run those businesses. I mean, often they’ll swap executives in and out upon acquisition, but sometimes they don’t and they want to know that person’s in place so they can trust that things are actually running well and that they’re running effectively without the founder, that it’s not a founder brand or company, that it is a system-based brand or company.

Cameron Herold: Yeah. You don’t want your systems walking out the door every night at 5:00 and going home, right? You want the systems deeply ingrained in the organization so that machine continues to run. And one of the best ways to and that’s why you don’t need an earnout when if you’re buying a company and the company runs and the people are handcuffed and the systems are in place and the redundancies are covered, cool. Ciao bella like, see you later, buddy. You know, I have a friend of mine who I introduced to an M&A firm years ago, and he sold this company for 107 million. He was doing 37 million in revenue, wanted to sell for 52, sold for 107 with no earnout, got 100 million in cash, a note for 7, no earnout, was able to walk away, day one, is because he had the second in command. He had the leadership team. He had the SOPs in place. And the company that was acquiring them recognized, “You know, we don’t really need you. So, yeah, I guess you can just go. That’s cool.”

Justin Donald: Yeah, I love it. You know, it is interesting to see. You know, there are a lot of investments I do in this space, whether it be direct investments, even funds that invest in companies. And I know it is very common when a company is bought that you want to take the top person out because they’re… You know, a founder in a role is often not the right fit. It can be but it is often not the right fit, right?

Cameron Herold: Most often when you buy the company, that founder is now going to be a pain in the ass. They’re not going to want to work as many hours. They don’t want you to make any changes. So, that’s the other part is you actually don’t want them to be there anyway. But if you need them to be there, it’s not as attractive as an acquisition. So, the other thing is like I was coaching a company based in Florida years ago. I coached them from 40 employees up to 700 and they raised about 255 million from Warburg Pincus right at the end of my coaching time with them. And I was talking to Bobby, their CEO, and I taught him this one system. He goes, “Wow, that’s going to change my company.” I’m like, “No. What will change your company is teaching all 32 of your C-level and VPs. That’ll change your company. But you being the only person that knows how to do this, will give you like a little tiny incremental leverage, but teaching everybody will tilt the universe.” So, growing your COO, right, growing the skills of your managers and leadership team, that’s what’s going to scale the company, not just putting the CEO into their own mastermind group.

Justin Donald: I love it. And you’ve been responsible for helping people scale their companies and exit. You’ve been involved in a lot of M&A transactions. I think the last time we spoke, I mean, there’s a good handful. I don’t know how many it is at this point in time. Is that something that you’re still actively involved in and helping friends, clients to scale and exit?

Cameron Herold: Yeah. I’ve got six clients right now that are working with an M&A firm to exit and I’m coaching them. I call it packaging them up in the Tiffany box with the white ribbon, right? So, that I can actually make them look shinier and more beautiful than they really are or as beautiful as they are and help them exit. But, yeah, I’ve got six that I’m working with right now. I’ve helped well over a dozen, three or four that have had $100 million exit pluses.

Justin Donald: That’s incredible. We had just the craziest experience in November where inside of a two-week or two-and-a-half-week timeframe, we had 12, well, for the whole month… All right. Few stats. Whole month, we had 12 exits. Inside of a two to a two-and-a-half-week timeframe, we had nine people exit their company, literally, just in November, which is just unbelievable, and most of these being a pretty sizable substantial exit. And also, great timing, right, because a lot of money has dried up in a lot of different places. And so, to kind of get that exit on the books in 2022 with a lot of groups that had capital, they had to spend by the end of the year. You know, I was encouraging everyone that I could since it’s been such a frothy year, you can sell.

Cameron Herold: Yeah. Get it done. Were they selling to strategics to private equity? Who are they selling to?

Justin Donald: Both. Yeah, a little bit of each.

Cameron Herold: Yeah. There’s a lot of money out there in the market still, and there’s been a lot of very patient money sitting since around March of 2020. Just pre-COVID hitting, there was money that was being built up and then all of a sudden COVID hit and that money got kind of panicky. And then since the crash just got a little nervous. But there’s some good money still out there to be had but, yeah, it’s definitely the time to sell.

Justin Donald: I love it. So, you know, kind of wrapping things up here and what a fun conversation this has been, what are some thoughts that you might just want to leave our audience with, things that maybe they can be thinking about to kick off 2023 the right way and make some moves?

Cameron Herold: You know, one is and I’ve been talking about this for a few years now, is that none of this actually matters. You know, we’re all going to die. This is just what we do to make money that we need to enjoy the journey and spend time with our friends and family and spend time with ourselves and our hobbies. Because at the end of the day, like none of this stuff actually really does matter. We’re all just walking each other home. You know, my mom died 20 years ago and that was hard for me to go through. She was the first person I knew who died and I was 35. My dad just passed away in September very suddenly at 80, super healthy, swam three days a week, golf three days a week, and then, boom, he was gone. I’m like, “What just happened there?” And it just continues to reinforce to me that this journey that we’re on at the end of the day is a blip in time. Right? So, be passionate about your goals, be passionate about your businesses but don’t forget to laugh and have a good time, and remember the people you’re working with are going through theirs. And then the second part is everybody’s actually struggling with something. Like, every single person you meet or employee that works with you is struggling with something with a debt, with a child, with a spouse, with a disease or an illness, or a worry or a fear or a relationship issue. Like, the human condition is you and I are both struggling with something today. I don’t know what yours is, you don’t know what mine is, but we all have something. And I think us to be cognizant of that and to really give a sh*t about people is pretty important as well.

Justin Donald: That’s powerful. I absolutely love that. And just this whole idea, this whole mantra that people are like waiting for tomorrow, they’re waiting for retirement, they’re saving their money, trying to scrimp until they get there. I want to encourage people to figure out a way to do it both. We talk about this all the time but it’s like let’s live today. We don’t know when the day is the last and we want to live fully.

Cameron Herold: One thing that’s been super interesting for me in the last 18 months of being a nomad is I don’t buy anywhere near as much stuff as I used to because I have nowhere to put it, right? Like, without a house and a car and closet space and garages, I don’t. So, Amazon doesn’t deliver to my house ever because there’s nowhere I would put the stuff. And then I just realized how little stuff I actually need to be happy. So, I think a lot of people can probably have a better life today, enjoy the life that they want more today if they buy a bunch less of the stuff that they don’t really need anyway.

Justin Donald: That is powerful.

Cameron Herold: How many darn TVs do we need?

Justin Donald: Exactly. I think it’s all about, are you spending time with the people that fill you up, inspire you, and that you desire to be around? Are you spending enough time with them and are you doing things that fulfill you in life? And these are all choices, right? These are all decisions we get to make when we’re not on autopilot, just in reactionary mode, and we’re taking time to be proactive, amazing things happen. So, where can our listeners and those watching find out more about you, Cameron?

Cameron Herold: Sure. So, all of my books are available on Amazon, Audible, and iTunes. The COO Alliance is the COOAlliance.com. And then also check out my course. It’s called InvestInYourLeaders.com. It’s all the core skills that you need to be able to grow your managers and your leadership skills inside your company.

Justin Donald: I love it. Just so cool. What a great time. What a great conversation. I appreciate you joining me and clearing your crazy busy travel schedule to come on the show.

Cameron Herold: Thank you, Justin.

Justin Donald: Yeah, my pleasure. I love closing out each episode asking my listeners one simple question and this is that question. What is one step that you can take today to move towards financial freedom, to move towards living a life you truly desire on your terms, not by default, but by design? Thanks, and we’ll catch you next week.

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