The Entrepreneurial Roller Coaster With Cameron Herold

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Today on the podcast we have Cameron Herold, Founder of The COO Alliance.

Cameron is known around the world as The Business Growth Guru. Cameron was groomed as an entrepreneur as a kid.

By age 21, Cameron had 14 employees, by age 35, he had already helped build his first two 100 million dollar companies, by the age of 42, Cameron engineered 1-800-GOTJUNK’s, insane growth from two million dollars all the way up to 106 million dollars in revenue at their peak.

That was with 3,100 employees and he did that in just six years. His companies have landed over 5,200 media placements in those same six years including coverage on Oprah.

Cameron’s one of the most well-respected businessmen in the world, yet he still battles failure, hardship, insecurities and struggles.

We’ll be discussing the best advice he ever got at the age of 20 and how that actually was the defining point of his life. He shares what  R&D means and why people overcomplicate business when just getting started. And Cameron openly shares his biggest insecurities and fears even after decades of success and much, much more.


Key Points From This Episode:

  • “Just do it”: the best advice Cameron got at the age of 20.
  • Being groomed as an entrepreneur at a young age.
  • Why your RND should stand for rip off and duplicate.
  • Listening and just getting started as your two cores.
  • Building relationships and asking for referrals.
  • Cameron’s God and Grandmother rule.
  • Looking for the path of least resistance and working smart.
  • The importance of transparency in business.
  • Why Cameron wouldn’t recommend a franchise to someone starting out.
  • How not listening led to failures along Cameron’s journey.
  • Discover where the COO Alliance is heading in the future.
  • The balance between being entrepreneurial and operational.
  • Listen as Cameron defines failure as not trying.
  • What the education system should look like according to Cameron.
  • Hear about Cameron’s challenge for credit idea.
  • Advice for somebody looking to get into business.
  • Getting systems in place and growing your business.
  • How Cameron steps out of his comfort zone.
  • Assessing risk by starting with your goal and working backwards.
  • And much more!
















Links Mentioned in Today’s Episode:

Cameron Herold —

Cameron on Twitter —

Cameron’s books on Amazon  —

The COO Alliance —

1-800-Got-Junk? —

College Pro Painters —

Cameron’s TED talk —

Mastermind Talks —

Dan Martell —

Eben Pagan —

Connor Blakeley —

Gary Vaynerchuk —

Kimbal Musk —

Peter Rive —

UpWork —

Hire My Mom —

Fiverr —

Dave Asprey —

Hal Elrod —

Transcript Below

Read Full Transcript


“CH: Yeah, so a lot of times I’ll get people sending me a note saying, “Hey, would you mentor me?“ I’m going to say, “No, I’m not going to mentor you because that’s a long term relationship.”


[0:00:12.1] ANNOUNCER: Welcome to The Fail on Podcast where we explore the hardships and obstacles today’s industry leaders face on their journey to the top of their fields, through careful insight and thoughtful conversation. By embracing failure, we’ll show you how to build momentum without being consumed by the result.

Now please welcome your host, Rob Nunnery.


[0:00:38.0] RN: Hey there and welcome to the show that believes embracing failure in a hyper focus way is the only way to achieve your dreams. In a world that only likes to share successes, we dissect the struggle by talking to honest and vulnerable entrepreneurs. This is a platform for their stories and today’s story is of Cameron Herold. At age 21, Cameron had 14 employees, by 35, he had already helped build his first two 100 million dollar companies, by the age of 42, Cameron engineered 1-800-got junks, insane growth from two million dollars all the way up to 106 million dollars in revenue at their peak.

That was with 3,100 employees and he did that in just six years. His companies have landed over 5,200 media placements in those same six years including coverage on Oprah.

Cameron’s one of the most well-respected businessmen in the world, still battles failure, hardship and securities and struggles. We’ll be discussing the best advice he ever got at the age of 20 and how that actually was the defining point of his life. What RND means to Cameron and why people overcomplicate business when just getting started,

and what his biggest insecurities and fears are even today after decades of success and much more of course. But first, I have a lot of travel coming up and luckily, all I need to travel with is a backpack for one reason only, it’s a shirt from an awesome Toronto company called Unbound Merino, they have clothes and apparel made out of merino wool and get this, you can wear it for months without ever needing to have it washed.

It’s a traveler’s absolute dream and it would turn you into a minimalist really quickly. Never check a bag again, check in at the show notes page for an exclusive fail on discount that you won’t get anywhere else. And, if you like to stay up to date on all the fail on podcast interviews and key takeaway’s from each guest, simply go to and signup for our newsletter at the bottom of the page. That’s


[0:02:26.3] RN: So, sitting here with Cameron Herald, we’re in Carmel California, just to give you a little context, we’ve got a beautiful backdrop here of the hills in Carmel, it’s not on the water, we’re inland a bit but Carmel Valley, it’s beautiful.

[0:02:41.4] CH: It’s pretty awesome actually.

[0:02:42.7] RN: You just got in?

[0:02:43.7] CH: Yeah, I got here about half hour ago and then got swarmed in the lobby and started – got into my panic attack right away and I panicked, I get nervous with stuff so I got nervous right away, realizing I don’t remember everybody’s name, they all knew me and I couldn’t remember them and so yeah, I got in my head a little bit but…

[0:02:59.5] RN: It’s stressful a little bit.

[0:03:00.9] CH: Good to be back.

[0:03:01.7] RN: You came straight form Phoenix?

[0:03:03.3] CH: Yeah, flew in from Scottsdale.

[0:03:05.8] RN: That direct American flight?

[0:03:06.8] CH: Yeah, to Monterey, it was great, there were six of us on the plane too.

[0:03:10.2] RN: Nice, I went from so, yesterday I came in, I did San Diego to Phoenix to Monterrey. Which is better than going like san Diego to San Jose then getting a car or trying to figure that out.

[0:03:21.5] CH: Yeah.

[0:03:22.5] RN: It was okay though. Cool, thanks for joining me.

[0:03:24.9] CH: You’re welcome, glad to be here.

[0:03:25.6] RN: Happy to have you here and happy to chat about your journey. Obviously you have COO Alliance, you helped kind of the right hand man, and entrepreneurs scale their current businesses but before we go in to kind of that, I want to go back to kind of your entry into entrepreneurship. Take us back to the first time that somebody actually gave you money in exchange for a product or service?

[0:03:48.0] CH: I’m going to go a little later than that then I’ll go back to it because I think that the whole being afraid to fail kind of concept for our audience and our listener right now. There was one defining moment in my entrepreneurial career when I was allowed, I was kind of given permission.

I was 20 years old and I was looking to buy a franchise of a company called College Pro Painters which is the largest residential house painting company in the planet. I was in university. They don’t sell you the franchise, they award it to you but you have to buy a vehicle and buy ladders and hire a bunch of people and you sign a 67 page franchise agreement and I was scared.

You’re getting a theme now, I’m scared. I remember calling my dad who was probably my very first mentor and he said, “There’s never a better time in your life to go bankrupt.” He said, “Try it, if you fail, it doesn’t matter but you’ll always regret not trying if you don’t” and the next day I signed a 67 page franchise agreement and had I not done that, I would not be anywhere today.

It gave me the foundation for all my business learning, it gave me the foundation for other business opportunities that I was presented with, it gave me the launchpad for 1-800-got junk. Literally that night, when he said to the word, “There will never be a better time in your life to fail because you don’t have anything, you got nothing, you don’t have any kids.”

I’ve got four kids now, I’ve got an estate that we live on, I got responsibilities, I’ve got homes in two cities, I’ve got – I have to make it happen.

[0:05:12.5] RN: You had a full-time job right now and you didn’t have any of those other businesses, you had lived your life like job to job.

[0:05:19.3] CH: I’d be too scared.

[0:05:19.1] RN: You have family, you’d be too…

[0:05:20.7] CH: Too scared.

[0:05:21.2] RN: Exactly, I wouldn’t be able to, I’d be paralyzed. Because failure would crush you at that point.

[0:05:24.1] CH: Even today in my business world today, it would be hard for me to pivot and do something completely different because I built a really great business now that the fear of failure is pretty big but I’ll tell you, that was the best advice I ever got at 20 years old was, just do it.

There’s never better time – you don‘t go bankrupt, you know, you’re always going to figure it out, you’re going to find a way. That was probably the defining point. If I go back to the earlier parts when the first time anyone – I was groomed as an entrepreneur, that’s why I had to start at 20 because the first time I ever did anything for money, I was eight.

I actually did a TED Talk about this. I have a talk that’s on about raising kids as entrepreneurs. It was originally subtitled instead of lawyers and then they cut out the instead of lawyers, it’s still been on the main TED site for seven years now.

My first entrepreneurial venture, my dad had these license plate protectors, you put them on the back of license plates and he made me go sell them door to door, I was eight. I was in grade two and I was knocking on doors and I was scared to death and the first guy said, “No.” I was like, all right, but if I go home and tell my dad, I didn’t sell any, he’s going to be mad at me so I’m going to knock on the next door and that guy said, “No,” then I knocked on the next door and they said, “No.”

I’m like, I still have to keep doing this and have to sell something. Then the next guy said, “Yes,” the fourth guy.

[0:06:40.2] RN: Were you mind blown?

[0:06:41.6] CH: I was over the moon. “Wow, he just bought one, this is awesome” and I went running back to my house and I said to my dad, “I sold some. “He goes, “How many people said no?” And I said, “Three and one said yes” and he goes, “Keep going until you get 10 no’s.”

I’m like, “But somebody said yes.” He goes, “Keep going till you get 10 no’s.” Then I went to the next house and they said, “Yes“ so I had now sold two in a row and I was like, that hooked me right away. I got two yes’s in a row and I don’t even remember if I got to 10, I’m not sure how long the business venture lasted, whether I did three blocks or 30 bucks.

[0:07:10.7] RN: Right.

[0:07:12.1] CH: I wasn’t afraid of failing so much as afraid of failing my dad. I was afraid of failing him because he was coaching me. You know, I was taking his advice and he taught me how to say what to say to the door and let me do it.

[0:07:23.5] RN: Is this like a structured thing like your dad consciously made the effort like, “I’m going to teach Cameron how to do this.”

[0:07:29.0] CH: Yeah, we were groomed as entrepreneurs, my brother and sister and I, my dad was an entrepreneur, both my grandfathers were – I even married into an entrepreneurial family and today my brother and sister and I all own our own companies as does my brother in law, as does my wife.

It’s always –

[0:07:43.2] RN: It worked.

[0:07:44.8] CH: That’s all I’ve ever known. Yeah, this was a defining – there were a lot of things like that, you know, swimming in the ponds at the golf course and pulling out golf balls and then selling them but I also learned to split them up into different groups, you could sell the bad ones as shite balls and the good ones, then you have like the pinnacles and deviations that I could sell for two bucks.

I learned marketing and packaging and then I probably had 15 business ventures by the time I was 15 years old.

[0:08:06.5] RN: That’s awesome.

[0:08:07.1] CH: you know, comic book arbitrage where I’d buy comics form the poor kids and then I would bike up to where the rich kids lived and setup a card table, I had a card table on my back and I would set it up and then I would sell them to them and then I go back down and buy them from the poor kids again because then I just realized you buy those, sell high and I got beat up one day because one of the rich kids found out where I was buying the comics. Yeah, that’s where I started.

[0:08:28.1] RN: That’s cool. So, for somebody that wasn’t groomed in kind of that entrepreneurial environment. Let’s say they just got out of college, what’s kind of your advice for them trying to get into that? Knowing they aren’t kind of cut from the cloth of getting a nine to five job.

[0:08:44.5] CH: You know, college and high school and grade school, I think ruins us. Unless you’re in the top 2% of kids, you’re told every day that you’re stupid and you’re told that you’re not smart because the A plus kids are smart but everybody else isn’t. I was a C minus all the way through school.

What I would take when I’m coming out of school now is you don’t have to be the smart person that all of the information exists. Your RND should stand for rip off and duplicate. Just take the best practices that already exist and do those, instead of trying to figure it all out, just do what the best people are doing.

Momentum will create your momentum. Just start and don’t worry about having the perfect website, don’t worry about having the perfect pitch, don’t worry, just start selling and you’ll figure it out as you go.

Then listen. Like really listen because when your customers tell you something, you can iterate, you can tweak it, you can tweak your pitch, you can tweak your market and listen. Those are the two core things.

[0:09:37.9] RN: What was the actual, obviously you had all this – you said, 15 before the age of 15. What was kind of the first real business where things got real throughout the journey?

[0:09:48.6] CH: The first real one was College Pro Painters. I had 12 employees when I was 20 years old, so I had a full operational business with marketing and sales and production and the vehicles and suppliers and six crews painting, six houses at the same time. That was the first.

[0:10:01.9] RN: What kind of money did you have getting started into that? Did you have like a good reserve?

[0:10:05.2] CH: No, I borrowed $3,000 from my dad, I borrowed $1,100 to buy an old van and $1,900 to buy some equipment. Then the guy who sold me the equipment let me pay him $900 of it later in the summer and then I used about $400 to $500 to get some marketing material going and then it was just Gods giver.

A lot of guerrilla marketing, anything I could do that was cheap, talking to people, putting flyers out and I didn’t ask for permission. I remember going to one of the golf clubs because I realized that all those people who were members of the golf club were rich and they could afford to have me paint their house and they might even like hiring a kid to paint their house because they’re giving back in a way.

I went and I stuffed fliers in everybody’s locker. The pro caught me and asked me to leave. So I left and then like an hour later when the pro left, I went back in and I finished off the locker room. You had to, right? There is no other way. I’m not going to – you don’t have the money to start.

Even in business today, you can just build relationships and ask for referrals and talk to your customers and do a great job and ask for another referral.

[0:11:08.6] RN: Right, I think people get so overwhelmed like all the information out there in terms of like, this online marketing course, this internet marketing. There’s just so much out there that you can go back to the basics and break it down really simply right?

[0:11:20.9] CH: Yeah, I go back, I call it my God and grandmother rule that if I wouldn’t do it in front of God and my grandmother then I shouldn’t do it and also, all of the grandmotherisms as I call them are all true, that if you treat people with respect and if you work hard and like – it’s all true.

Business isn’t difficult. I always see that fly. You know, if you’re listening and you see the fly kind of trying to get out the window and it’s banging it’s head on the window but if you look like 10 feet away, there’s a door and it’s wide open, just turn and go out the door.

I always look for that path of least resistance, I look for the easiest way, the shortcuts and I think a lot of people are just – work hard constantly, well, maybe it’s about working smart, maybe it’s about getting to know the right people even why we’re at this event right now, Mastermind Talks is because we’re hanging out with really successful people who are out here to help each other.

[0:12:05.3] RN: For somebody that’s – I was just talking to Dan Martell about this and he said, the number one thing that’s been like his biggest catalyst is people, it’s – you know, in the negative sense where he went to jail because he was hanging out with the wrong crowd but also in a positive sense where he elevated his network and that changed everything for him.

[0:12:22.2] CH: yeah, it’s not who you know, or sorry, it’s not what you know, it’s who you know and then your network is your net worth, right? It’s by spending money, I had a dinner 10 years ago with Eben Pagan who is a big internet marketing guy and I didn’t know who Eben was and we’re having dinner together just the two of us and he said, he asked me where I was investing my money and I was telling him the stocks.

I said, “What about you?” He goes, “This year, I’m putting, I won’t tell you the exact number but it was well over a hundred grand into relationships.” I’m like, “What do you mean?” He goes, “I’m going to spend 40 grand to go to Necker Island and then I’m going to spend 20 to join this group” and he goes, “I figure that if I’m spending time with really successful people.”

It was about 200,000. “My 200,000 will be worth about two million because of the relationships that I built and if I put 200,000 into the stock market, it will probably be worth 220,000.” I’m like “Wow, you’re right. You’re going to get 10% in the market but you’re going to get 10x return on your relationships.”

As long as you spend time getting to know people and being vulnerable and not trying to sell to them, right? Just showing up and –

[0:13:19.0] RN: Not trying to take.

[0:13:20.2] CH: Yeah, trying to give.

[0:13:21.2] RN: So for somebody that doesn’t have 200k to put into relationships right now, maybe they’re just in a job but they know they’re kind of destined for more, like, they don’t have those people around them.

[0:13:30.7] CH: Go to the tech meetups that are in your city, go to some of the meetup groups that are in your city. You know, organize, just post something on Facebook and say you’re getting some people t together for coffee, and go and buy 10 people coffees. I had dinner last week in Austin Texas and I put a note on Facebook and I had 10 CEO’s come to the dinner.

I paid and it was $890 total because one guy bought a $160 bottle of wine. That’s not a lot of money to spend with 10 people, right? You could do that over coffee and it would cost you 50 bucks.

[0:13:57.2] RN: Totally.

[0:13:58.7] CH: Even enough to buy the coffee. I’ve seen people that they call it lobby surfing or lobby con, go to a conference, they won’t pay to go to the conference and they’ll hang out in the lobby at the conference just to talk to people.

[0:14:09.6] RN: Like that lobby con.

[0:14:11.5] CH: Well, I’ll tell you, there’s one of the kids who I mentored, a guy named Connor Blakely, do you know Connor?

[0:14:15.9] RN: Yeah, young guy, right?

[0:14:16.9] CH: Yeah, 17 years old. He’s known as Gen Z guy or Gen Z I guess and I’ve known him since he was 15, he cold called myself and Gary Vaynerchuk on the same day to ask us if we would mentor him, neither of us knew who he was, we both said yes.

I did my first call with Connor when he was 15.

[0:14:30.6] RN: Why did you say yes?

[0:14:32.2] CH: Because he asked and he knew what he wanted. That was the key. Well he actually could tell me the top five things he wanted to learn from me and it was learning, it wasn’t introductions and I said yes that we would do the call, I did a quick skype call with him for half hour and I said, “I need to talk to your parents really quickly to make sure that it’s okay” because it was kind of weird, right?

This guy talking to a 15 year old kid and his parents came in and waved and dad said, “Thumbs up” and I said, “Okay,” we talked and he was very clear on what he wanted to learn. Afterwards, he followed up with an email saying thank you in a physical note that he mailed to me saying thank you.

That was it, that’s all he needed to do and from there, I’ve become a huge fan, I introduced him to everybody I can so that’s another thing, just reach out and ask. Every single person who’s successful got helped by someone at some point in their career and at some point, we, as humans like to help other people.

We tend to say yes but you have to respect their time. If you call and say, you know, “Hey, will you mentor me? “You’re going to say no.

[0:15:26.7] RN: I was going to ask, what’s the difference between what Connor did versus somebody you have said no to?

[0:15:32.1] CH: Yeah, a lot of times I’ll get people sending me a note saying, “Hey, would you mentor me?” I’m going to say no. I’m not going to mentor you because that’s a long-term relationship. That’s what I do for money as well. I coach and mentor CEO’s all over the world, they pay me to do that. Chances are, probably not going to do it for free.

Connor didn’t ask me to mentor him, he said, “Do you have 15 minutes, I’d like to do a quick call with you to ask you these five questions.”

[0:15:54.0] RN: Totally different.

[0:15:55.0] CH: Sure, done, right? Absolutely. Then guess what happens after 15 minutes. “Hey, do you mind if I ping you in a month or so with a follow up question?” For sure. Then guess what happens, all of a sudden, that’s like – I get emails and texts. Literally, I got a text message from one in the plane today.

I got a text message for like – I get text messages from Connor and emails form Connor all the time asking me questions and I will go through brick walls for this guy now.

[0:16:16.6] RN: It’s because he came strategically?

[0:16:18.9] CH: Yeah and he understood what he’s looking for. Yeah, there he is, 3:00, he texted me again.

[0:16:23.6] RN: That’s great. Did you run into any hard – obviously it was a big mental shift to actually invest in College Pro Painters. Did you run into any struggles, hardships at the beginning or any massive failures through that business?

[0:16:38.5] CH: For sure. I was probably six weeks in to running the business and I hired four or five of my really close friends to move to the city to work for me. We were about six weeks into the business and they thought I was making tons of money and they hated me.

I was almost bankrupt and wasn’t making any money. What they saw was revenue, they didn’t understand all the expenses , they didn’t understand the difference between revenue minus expenses equals hopefully profit and I wasn’t making any. I went and told my dad, again, my first mentor, right?

My dad said, “Well why don’t you show them your accounting?” I’m like, “What do you mean?“ He goes, “Just literally show it to them, take your numbers and put it right in front of them” so I have all the guys over and we had pizza and beer and I showed them my numbers and within a half an hour, they were all worried we were going bankrupt and they were committed to help me grow.

I turned the whole thing around, that open book financials.

[0:17:28.0] RN: Being transparent before is like a cool thing right? Because a lot of business owners try to hide that stuff.

[0:17:33.4] CH: Well, I think people, again, there’s nothing to hide you know? Either your employees think you’re making too much money which is almost always the case because they can’t add up all the expenses and they don’t understand.

I told my assistant the other day that 42% of my gross revenue goes to the government. She had no idea right? If I run a seminar and I have people paying seven grand for a couple of days to come and – they don’t understand that 42% of that doesn’t even hit my pocket.

[0:17:56.4] RN: Not just going into your bank account.

[0:17:58.3] CH: It’s gone, right? Plus the expenses and the food and the marketing. They don’t always sad that stuff up. I think transparency is really, it’s easier too.

[0:18:06.5] RN: Yeah. What was the transition from College Pro Painters, what was the evolution there and where did it go?

[0:18:12.7] CH: College Pro was there for seven years, I was a three years running a franchise and then four years at the head office and I worked at the head office, coaching and mentoring franchisees so I would recruit, interview, hire and train franchisees and then coach them for four months and two of the last franchisees that I hired and coached.

One was Elon Musk’s brother Kimbal. The other was his cousin Peter Rive who runs Solar City and they both worked for me, it’s their very first, I taught both first…

[0:18:38.8] RN: First business?

[0:18:39.6] CH: yeah.

[0:18:39.8] RN: Very cool.

[0:18:40.2] CH: That does a reference for Elon in his first round of funding because they wouldn’t back Elon, they backed Kimbal with his College Pro Painters experience.

[0:18:46.9] RN: That’s awesome.

[0:18:47.5] CH: Elon’s book as well, it’s pretty funny.

[0:18:48.6] RN: Yeah, that’s cool. What actually made you want to go to the head office? Did you still have the franchise, is it still running on its own?

[0:18:56.4] CH: Once you, at the end of every year, you have to reup and take it for the next year so at the end of three years, it was – I was done, finished school and I saw an opportunity to learn how to really run businesses.

As an example, there’s 60 people at the head office and we would hire and recruit and train 800 franchisees who would then hire 8,000 painters and then in four months, we’d paint 64 million dollars in houses and then 8,800 kids would quit and go back to school.

I was in the top 30 people in that company so every year, getting taught how to build a 9,000 person company was pretty huge training.

[0:19:29.1] RN: That’s cool.

[0:19:29.7] CH: That’s where I got a lot of my peer to peer business training.

[0:19:31.8] RN: Got it. You might be a bit bias here but – because you kind of got in to the entrepreneurial world in the franchise model. For somebody looking to get into business for the first time.

[0:19:41.1] CH: I don’t like franchises.

[0:19:42.2] RN: Okay.

[0:19:42.7] CH: Yeah, I’m not a big fan of franchises because most franchisors, the reason they franchised is they couldn’t make enough money on their own so they decided to sell franchises as a way to leverage. Now, if it’s a really good system, talk to the franchisees if the franchisees are making money, then it can be okay.

When we built 1-800-got junk as an example. Our franchisees made tons of money. Everyone wanted to buy more franchises because the franchisees did well and we did well.

[0:20:07.4] RN: Got it.

[0:20:07.8] CH: But there’s lots of systems where it’s not a good model.

[0:20:09.8] RN: Got it. What’s been like the most massive failure for you on your journey?

[0:20:15.5] CH: One was not listening. Where we had some – I imagine you can tell kind of outgoing and extroverted at times and I’m also introverted, that’s weird. We had a head of finance who was very quiet and very amiable, very analytical who kept telling, us at 1-800-got junk to be careful. I was the chief operating officer, I took it from 14 employees to 3,000 and right around the pinnacle of our growth, probably when we were about 2,000 employees.

He kept saying, “Be careful, you’re spending too quickly, you’re opening too many corporate locations, we’re spending too much on bonuses, this office renovation is too expensive” and the CEO and I kept saying, “We’re fine, we’re good,” because in our head, we were, we though we could manage it all and then one day we needed to borrow some money because we’d spent five million dollars of our current cash on office renovation and moves and bonuses, et cetera.

We went to the bank and the bank said, “Well you don’t let have any cash.” “Yeah, no, of course not, that’s why we’re here. We’ve been profitable every year for six years, we’ve used all of our own money, we have no debt“ and they went, “Well that’s really stupid” and we’re like, “Why? Isn’t it smart to not have debt?” They said “No.

You actually should have leveraged your balance sheet, you should have come to borrow money when you had five million, you should have come to borrow five million.” “We didn’t need it.” They said, “But you don’t understand finance,” we went, “You’re right, we didn’t.” We didn’t really understand how the financial world worked. The big lesson was that you know, if you’re buying a house, you get a mortgage but when you’re building a business, a loan is just like a mortgage against your business.

If you take a little bit of cash in the right way to allow yourself to grow, you can fuel your growth but we also wouldn’t listen to someone who is quiet because we thought, well I don’t even know if we thought we knew better, we just weren’t listening.

Now what we decided was if we have someone who we’ve hired, it’s our job to listen to them otherwise why did we hire them in the first place? We hired really smart people and we put systems in place to make sure that we listen.

[0:22:01.7] RN: What’s been the toughest part? I’m talking, because obviously entrepreneurs, it’s all a roller coaster, right? High’s tons of high’s, tons of really low lows.

[0:22:11.7] CH: I had a massive low five months ago, I got hit with a $420,000 tax bill that I didn’t know was coming. Right at the left field.

[0:22:21.4] RN: That’s the thing, they never end, right?

[0:22:22.8] CH: the day before I went away on Christmas holidays with my wife.

[0:22:25.3] RN: It’s the worst timing too.

[0:22:27.0] CH: It was brutal. I sat down and I cried, probably smoked a joint, a drink and I just – I made a list of every expense I could cut. I made a list of everywhere that I could quickly bring in cash and it was all very low hanging fruit, it was like, quick and easy things that I could do to cut and drive revenue and drive gross margins fast as possible. Three and a half months later, I was done, I paid it, I covered it and it was good but it was extraordinarily scary.

[0:23:00.1] RN: So that’s interesting because it sounds like how long was it that you were like in shock before actually?

[0:23:05.9] CH: 10 days.

[0:23:07.3] RN: Okay so 10 days and then you’re like, “Okay I got to devise a plan”.

[0:23:10.0] CH: It was the whole Christmas holidays where I promised myself I wouldn’t work. So I just decided while I was gone, I would just be in the moment with my wife and be in the moment and be in the moment and it was hard but I knew myself well enough that if I started working on the plan, I wouldn’t be able to enjoy the holiday. We need to recharge as entrepreneurs. We’re like a phone that you have to plug your phone or it doesn’t work. We need to recharge and allow us –

[0:23:35.1] RN: And if you don’t you’ll come to a breaking point.

[0:23:36.5] CH: Yes, you come to a breaking point fast.

[0:23:39.6] RN: Yeah, what are you most excited about today? What are you working on?

[0:23:42.9] CH: What I’m working on now is the COO Alliance for sure. It’s the only network of its kind in the world for second in commands. There are a million groups for entrepreneurs and there’s places for marketers and engineers and lawyers but no one had ever put anything together for the second in command. So I’ve got the only network where the COO’s or VP Ops, GM’s can actually mastermind together, learn from each other, leverage each other.

[0:24:03.1] RN: Got it. Do you feel like you are more on the creative strategic side because obviously the COO side is very systems driven process, driven operations. Which side do you feel like you’re strength’s at?

[0:24:13.6] CH: I’m kind of an anomaly. I play both sides where I’m very entrepreneurial because that was the world I grew up in but I am also very operational. So I have ADD bipolar and I am on spectrum for turrets. So according to the medical system, a little bit disaster but I’ve learned that those are all my strengths so I don’t medicate for any of those but my OCD, I am obsessive-compulsive enough that that counters everything. So I am operational to a point but I would be a terrible COO past the 100 million.

[0:24:46.7] RN: Got it.

[0:24:47.1] CH: You know we took 1800 got junked from two million to a 100 million and then when I left, they were to go from a 100 million to a billion, I can’t do that part.

[0:24:54.5] RN: Got it, what’s the difference?

[0:24:56.3] CH: It starts getting big, you know we had 3,000 employees. We were operating in 330 cities and four countries, you know 46 states, multiple languages, 250 people at the head office it just is big. It’s political, there’s cross matrix decision making, you are dealing with consultants, it’s just big and you can’t be entrepreneurial. You can’t make decisions the way that you make them as an entrepreneur. You know when you are in the 10 to a hundred employee range, being an entrepreneur is easy because you can make decisions on the fly.

You can trust your gut, you can trust your gut when you got 3,000 employees. You have to trust the data, you have to trust the analytics. You have to challenge your assumptions and I am not that good at that.

[0:25:36.7] RN: How would you define failure?

[0:25:38.7] CH: How do I define failure? I don’t really think about failure, I don’t know, probably next question.

[0:25:46.3] RN: Yeah, let’s think about when you are starting like College Pro Painters.

[0:25:49.9] CH: I think it’s not trying. I think it’s not trying, someone asked me the other day what would the words be on my tombstone when I said, “He Tried” it sounds a little sad in a way that I rethink it every once in a while but he tried.

[0:26:02.1] RN: He did it, like you went for it.

[0:26:03.7] CH: I just tried, right? I tried my best as a husband, I’ve tried my best as a dad, I’ve tried my best as an entrepreneur and a friend. I’ve tried and I think failure for me would be not trying.

[0:26:12.8] RN: I like it. I like it.

[0:26:14.9] CH: Because I always measure down, I don’t measure ups. There’s always going to be someone who’s richer, who has a fancier car or a flashier wife or something. My wife is pretty amazing but there’s always somebody who’s got bigger and flies private and so if you measure against that then you are always going to feel like a failure.

[0:26:32.0] RN: Because there’s always somebody there.

[0:26:33.2] CH: And that’s how the school system is, there is always somebody smarter so that meant I was a failure and I refuse to accept that today that I measure against all the kids who I was smarter than. Wow, I am actually pretty smart or I am making a lot of money, I am pretty successful and so I think failure is just not trying.

[0:26:51.5] RN: You talked a little bit earlier about the education system, what should it look like?

[0:26:57.3] CH: Oh, well it’s different as well all right? Remember I went to school, so I am 50, I went to school, finished school 30 years ago, there was no Google. To look something up you have to go to the library, go through a Dewey decimal system and a filing and you had to find a book and then you took the card to go find a book and it was out. So then you went back to the system like it was insane right? So you had to be the smart person.

You had to memorize everything because you didn’t have a network to tap into. Now I think the school system should be completely different. The other thing I think – so one thing is everyone should get an A. There should be no grades, everyone should get A’s because to systematically every single day tell people they’re stupid is destroying our entire economy right? But if you have it for everybody you are actually really smart and build their confidence.

It should be half of what school is about. All the tests should be open book, all the tests should be in groups, it should be about collaborating, researching, problem solving as groups, leveraging each other’s resources, leveraging each other’s strengths. Hey, you are good at design, you are good at research, you are good at copy, figuring that out and working together as a team. So collaborating, problem solving, researching, presenting as a group and everybody gets an A.

And you can do your research and study whatever the hell you want. So if you want to study podcasting, go for it. You want to study Native Indians? Go nuts. You want to study World War whatever? That’s your prerogative but –

[0:28:16.4] RN: People should be doing stuff they are interested in, right?

[0:28:18.2] CH: Right, it’s insane so –

[0:28:19.3] RN: Well I know that’s what you do.

[0:28:20.5] CH: So the school system is so stupid and it would relieve the pressure off the teachers because now the teachers wouldn’t have to grade everybody. The teachers would be there to encourage and align and I think what’s going to happen and we’re going to see it in the next ten years, the school system as we know it today will be completely destroyed.

[0:28:33.3] RN: It will have to be.

[0:28:34.0] CH: Yeah and the university pay for come out with theory for four years and come out with debt is insane. It will collapse as well.

[0:28:39.9] RN: It’s such a big institution though, what do you think is going to be the downfall of it that will actually make that shift happen?

[0:28:47.0] CH: Well I’ve got an idea that I actually wanted to do a TED Talk on it is to take almost a challenge for credit system where you say, you get companies like Google that they will say they will hire 10% of their workforce as long as they don’t have a degree, like you can’t have one. So 10% will not have one but they will provide enough points that they’ve gained from doing things. So you can get points for apprentice, you can get points for traveling around the world.

You can get points for doing Con Academy courses, you can get points for coming to events, you can get points for job shadowing and there’s all these points that you gather and the points will actually give you a degree like certification and based on what we are saying is challenge for your own darn credit. If it takes you three weeks or three years, it doesn’t matter and guess what? It’s free.

[0:29:30.6] RN: Yeah, I love that. That’s awesome because you are actually doing stuff that you want to do.

[0:29:34.5] CH: Yeah, I would hire people like that. I could go to the Mastermind Talks tomorrow and tell a 150 entrepreneurs to sign up for it and every one of them would.

[0:29:41.9] RN: 100% they really would.

[0:29:43.5] CH: Everyone so I think that is the kind of movement that will happen because people are just pissed off.

[0:29:48.2] RN: Is that something that you want to be in the forefront of like actually?

[0:29:51.3] CH: I would spearhead it and I would talk to people and get it going as a charity and a movement but I have a business and kids so.

[0:29:58.3] RN: Not dedicating your life to it.

[0:29:59.8] CH: Well it’s funny like Simon and I where Simon and I have been friends for 15 years since before anyone knew the two of us, we have known each other. In fact, I have hired him to do our branding and remarketing –

[0:30:07.5] RN: How did you guys meet each other initially?

[0:30:09.0] CH: He flew out to meet me because he read about me in Fortune Magazine and he wanted to find out if 1-800 got junked and myself and Brian were real literally. So he flew from New York to come and meet us for lunch and he and his partner were running an ad agency at the time. So when we were doing our TED Talks, his TED X was about his upcoming book and mine had nothing to do with anything I made money at which is so stupid.

So people interview me all the time about raising kids as entrepreneurs. I’m like, “Yeah, I am not like anybody else” right? So yes, I might want to spearhead something like this challenge for credit system as an idea and a concept because I think someone would latch onto it.

[0:30:44.5] RN: But do you not ever think about doing it for money?

[0:30:48.6] CH: No, for free.

[0:30:50.3] RN: Or you’re so in the zone for what you do.

[0:30:52.1] CH: There is no reason for anybody to actually – oh sorry do you mean doing which?

[0:30:55.7] RN: I mean like you said, you did the TED Talk and so you don’t make money with, is that something that you feel strongly enough about to pursue that as a business opportunity?

[0:31:04.0] CH: Oh no, yeah I wouldn’t want to pursue. I think this challenge for credit idea should be done for free and it shouldn’t cost anybody any money and it should be crowd sourced and literally is a way to – I really want to tear apart the school system. I’m so fundamentally pissed off at the way I was treated.

[0:31:17.5] RN: A lot of people are, yeah.

[0:31:18.1] CH: I was literary destroyed, it’s the reason for my insecurity. It is the basis for me being as confident as I should be with all my successes, I still walk around saying, “I hope people like me, I hope they think I am smart” that’s fucked up. That’s because 18 years I’ve been told I was stupid.

[0:31:32.6] RN: Were your parents kind of counter balancing that a little bit like obviously raising it like an entrepreneur?

[0:31:37.5] CH: No, my mom wanted me to work harder, she came from that protestant work ethic, work hard. My dad couldn’t have cared less about school. If you had to cheat to get by, that’s cool, here’s how you cheat. Here’s how you write your cheat cheats and slide it under. My dad was all about the shortcuts so I don’t think he really cared. My dad went to a university but he went to school to be a dentist and then never used his degree. So I think he understood as well.

[0:32:00.5] RN: What did he ended up doing?

[0:32:01.9] CH: Running his own company. He ran some gas stations and then became an automotive industrial reseller that supplies a lot of big companies with automotive parts.

[0:32:09.2] RN: Got it, so for somebody looking to get into business for the first time, you worked with mostly experienced entrepreneurs but maybe you’ve had this conversation a lot with them and you are obviously in this Mastermind Talk groups so for somebody just looking to get started in the business, don’t have an idea, don’t know where to get started –

[0:32:25.3] CH: How old are they, 20?

[0:32:26.3] RN: No, let’s say they are 25, 26, a few years in corporate America.

[0:32:31.8] CH: I would say quit your job today, cold turkey and go find four companies in your city. Let’s say you’re in Austin, Texas. Go find four of the best companies to work for and ask them if you can apprentice for them for six months each and you will do whatever they ask. All you want is minimum wage or nothing, somewhere between zero and minimum wage but you want to be able to sit in some board meetings. You want to go sit in with the CEO once in a while and do all the other stuff.

And just create a little process for yourself to be surrounded by these smart people. If you do that with four amazing companies over a period of a year or two, you will learn a ton.

[0:33:09.0] RN: Yeah, I love this so much more because like I say, I have read that question and so many people are like start the side hustle which keep your job, start the side hustle which that is not what worked for me. It worked for me quitting cold turkey and going to jump into a new business and learning and I actually went the route that you pretty much said. I went to work for a company that was selling health and beauty products and I learned how to sell them online working for them.

[0:33:34.4] CH: Yeah I don’t think the side hustle works because I you can spend a lot of your side time learning and watching podcasts and listening to podcast and learning online. That’s great, reading and devouring and starting to put it on place but to be successful you’ve got to dive in.

[0:33:49.4] RN: Total immersion, yeah. I love that answer because everybody is side hustle, side hustle and –

[0:33:56.0] CH: Well even I see businesses today so I will coach on entrepreneurs today who have this next business that they are starting and I said, “You know sitting on a toilet is okay but if you sit on two toilets it gets kind of messy” and you can’t sit on two toilets. You have to get your one business up and running and then have a team running it for you to allow you to have the time to go run your second one.

[0:34:13.4] RN: What would you say for somebody that’s a solo entrepreneur that they have a business that’s running. They’re doing everything themselves, maybe they have a couple of VA’s, what would you tell them in terms of scale of actually growing that and getting systems in place?

[0:34:26.2] CH: Sure, a couple of things. One, if you are only able to work for two hours a day let’s say you’re critically ill or your spouse was or your family, you could only literally work for two hours a day, what would you do during those two hours? And then start delegating except that, that’s one starting point. Secondly, think about how much money you are making this. Let’s say you are making 100 grand, that’s $50 an hour, start delegating everything that’s on your list that is worth less than $50 an hour.

And then start leveraging places like Upwork or Hire My Mom or Fiverr to just get miscellaneous stuff done and out the door so that you can keep working on the critical things and then last is momentum creates momentum. So don’t worry about perfect. No one actually cares about perfect even whatever you got in university or high school, no one ever looked at your university transcript since. That’s the thing that pisses me off the most is when they kept saying go for A’s no one’s every cared since.

They could have said go for C’s that would have been enough, right? So I think if you are starting your business and you’re going to get going just get some stuff out the door, don’t worry about the perfect website, just launch one. Don’t worry about the perfect sales call, just do one.

[0:35:29.9] RN: That’s a great point because I think so many people getting started think with their first business it’s going to be the only business they ever do it’s going to be this is it, it has to be perfect.

[0:35:39.2] CH: Yeah that will be one of seven.

[0:35:40.8] RN: Exactly and that’s for almost everybody. I am sure there is the anomaly of somebody had started their first business and they still do it today maybe, I don’t know. I haven’t met that person but I think it does paralyze a lot of people.

[0:35:53.2] CH: No, for sure it does.

[0:35:54.6] RN: What’s the last thing you did to get outside of your comfort zone to stretch your limits a little bit?

[0:35:59.9] CH: Oh God.

[0:36:00.2] RN: Whether it’s business or personal.

[0:36:01.7] CH: Wake up this morning? No, I woke up, I talked to a couple sitting beside me at a table today in a restaurant because I don’t like talking to strangers so I decided to force myself to say hi to them. That was out of my comfort zone.

[0:36:15.8] RN: A hundred percent right? It sounds so simple but it makes you grow.

[0:36:19.5] CH: Yeah, I am pretty much always out of my comfort zone now. I’ve started to give up on being insecure and I talk about it because then that gives me strength so yeah, I am always out of it. I am stretching, coming to Mastermind Talks. I love being here because I am stretched by every single person that’s here, right? Everyone is doing amazing stuff. I am learning that if I go in and ask questions and find out what they are doing and what they are working on like I am fascinated by this technology you’re using for podcast. You just keep learning by asking questions.

[0:36:47.4] RN: And is it how exciting? I know you said you’re extroverted but also introverted, how do you do in this big group settings with a lot of people?

[0:36:54.8] CH: Drink, yeah drink. True, it’s true. I leverage a little bit of that to just relax. I realize that everybody is a little nervous. I’ve also realized years ago that every single person is really a 16 year old trapped in an adult body, right? You’re the 16 year old Rob, I’m the 16 year old Cameron. You are actually a warmer version because you’ve got a sweatshirt on, I realized I didn’t bring any sweaters today in here.

[0:37:19.1] RN: I’m making you sit on the patio.

[0:37:20.4] CH: Yeah, so I realize that everybody is a little scared. Everybody is a little awkward, everybody is a little insecure and everybody is actually more worried about their own shit than worried about you so just go talk to people so you just go.

[0:37:30.2] RN: How do you assess risks when you are looking at whether it’s a new business, a new investment, what do you take into account?

[0:37:37.0] CH: I reverse engineer so I start with a goal and then work it backwards so I look at probably what the ROI would be and what my time and money is going to be to get there. I try to rip off and duplicate, I try to find paths that other people have done like I am actually starting a podcast without wanting to be a podcaster but I am going to start interviewing second in commands. Everybody is interviewing the entrepreneurs, no one is actually interviewing the person who is putting it in place.

So I am just going to talk to all the second in commands of all the people that get interviewed and I want to find out like what do you use and what makes a good podcast and what doesn’t and what’s the proper amount of time and how many do you release and for post-production does it really matter or doesn’t and I just want to ask questions. So instead of me trying to read lots of books, I’ll just talk to 10 guys that are doing it and that will get me most of the way.

[0:38:20.0] RN: That’s exactly it and I think it’s like you said, it is not talked about enough, like COO’s I mean it was on my last business I had a partner and we got into the business’s partners by so we were working for an entrepreneur like working for that health and beauty company. We both learn the skill there, we’re both like okay they changed a lot of things. We wanted to leave and now we have the skill to go do it on our own.

But we just jumped into that because we were both trying to escape that company and we become partners without every considering should we be partners like does your skill set compliment mine and absolutely know.

[0:38:59.2] CH: I would say that for most people as well that are sitting and thinking about starting a business, you don’t need a partner and I think that is an insecurity that people take. Let’s start a business, who can I start one with, do it with me and you don’t need one. What you need is to surround yourself with mentors or people who you could ask questions of and realized that everybody is a little bit scared but to give it half your company to another person –

[0:39:21.6] RN: Just because you are insecure?

[0:39:23.0] CH: Right this isn’t having a family. You don’t technically need another person. Well you don’t even really need another person to have a family but it’s easier, right? You are not raising kids here. You are going to hire people, you’re going to outsource, so the confidence thing you can get over. A person isn’t going to ever solve that confidence, it’s not worth giving up half your business for that.

[0:39:41.6] RN: It’s crazy saying it was exactly the situation I was in and we had the same skill set so it is not even like he was a good process systems guy because that is not me.

[0:39:50.9] CH: Sure, you probably got along because you were both the same.

[0:39:52.9] RN: Exactly but great friends, bad business partners.

[0:39:57.1] CH: Happens a lot.

[0:39:58.0] RN: I’m sure.

[0:39:59.5] CH: I even got a couple of my clients who are co-CEO’s working with marriage counselors right now and I’ve got a marriage counselor who half of her business is focused on co-CEO’s and she just runs them through the normal marriage counseling work because it is all about relationships and trust and dedication and yeah, it’s interesting.

[0:40:18.2] RN: That is interesting so what are you most excited about moving forward? Obviously you are passionate about the alternative education and getting that change but with everything that you do in your coaching and COO Alliance.

[0:40:28.8] CH: I’m excited about finding a sweater for tonight. That’s going to be key here.

[0:40:32.9] RN: Jayson wasn’t lying, it is going to be chilly tonight.

[0:40:34.6] CH: I don’t read stuff and I was going to rush talking and I just threw a bunch of stuff in the suitcase, yeah I was thinking warm and I just left Scottsdale. So what am I most excited about, I am excited about the COO Alliance for sure, I’m definitely excited about a couple of my books that have come out. So I’ve got one book called Meetings Suck that has done really, really well and my first book Double-Double six years ago is doing great.

And then a third one that just came out that I am giving everyone a copy here is called The Miracle Morning for Entrepreneurs, a walkthrough with Hal Elrod. So I am excited about those and some of my clients, I am coaching some really, really cool companies. I’ve been coaching Dave Asprey from Bulletproof Coffee and coaching a guy named Hussein who’s gone from four million to 58 million on Amazon and I just got some really cool entrepreneurs that I coach.

[0:41:18.6] RN: In Toronto?

[0:41:19.2] CH: Yeah, oh do you know him?

[0:41:20.3] RN: Yeah, we had a dinner in Toronto together.

[0:41:22.5] CH: Yes, so I coached him for four years, I still coach him today. I literally started coaching him and he was almost bankrupt. He couldn’t afford to pay my bills two of the months and I said, “I am not stopping coaching you now. I am going to coach you anyway if you can ever pay me back, pay me back but we are going to get you there” and he’s killing it. So I am excited about a number of my –

[0:41:37.0] RN: So you really invest in this guys if that is the case. There’s a deeper relationship there.

[0:41:42.8] CH: Oh yeah and there is a million coaches, I am not coach. I’m much more a mentor and because I have built companies and a lot of them are really good cultures like really strong company culture, that’s really what I am known for as well.

[0:41:54.0] RN: How’s Hussein? Has he had a big team?

[0:41:56.4] CH: He’s got about 45 people.

[0:41:57.3] RN: Okay, with selling with stuff on Amazon, do you teach them on culture aspect like is there a good culture there?

[0:42:04.2] CH: Oh yeah, great culture. He’s got I think 78% positive net promoter score on his employee satisfaction. Yeah, he does really well. He’s selling on Amazon, he’s just there. It’s where their customers are buying, he’s got an office filled with people that are a lot of numbers people but a lot of marketing sales packaging, copywriting, design, he’s got some really cool people.

[0:42:23.4] RN: He’s a smart guy, I like him a lot.

[0:42:24.8] CH: Wicked smart.

[0:42:26.2] RN: Yeah, he’s really cool awesome man. Well I appreciate you taking the time.

[0:42:28.9] CH: Oh you’re welcome.

[0:42:29.8] RN: I’ll let you get a sweater.

[0:42:31.2] CH: I know, I am freezing right now, this is nuts.

[0:42:33.2] RN: I appreciate it man.

[0:42:34.1] CH: I appreciate it, thanks for having me.


[0:42:38.3] RN: All right, so you can find Cameron @cameronherold on Twitter and of course, to all the links and resources Cameron and I discussed including more information on his current books and ventures can be found on the page created especially for this episode. That will be at and next week, we’ve got a good one. We are sitting down with my good buddy, Nick Tarascio. Nick is the CEO of Ventura Aviation and other than Unbound Merino with Dan Demsky, Nick might have my favorite company in the planet.

Outside of just running the Ventura Aviation company, he was a pilot by 16, he was flying liter jets by 19 and now he does this really fun flight adventures with incredibly interesting people and entrepreneurs, spontaneous last minute trips where you just hop in a plane and go. He’s making me want to get my pilot’s license so I can join in on the fun but we have a great chat, very light hearted, casual you don’t want to miss it.

And if the podcast has your wheels turning a bit, please email me at and let me know what your biggest struggle is in either getting started or breaking through the next level of wherever you’re at and as I continue to build up Fail On with the goal of helping people embrace failure, share their struggle and decide once and for all to create change in their lives, I’d be really grateful for a couple of things.

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