What 40 Years of Failure Taught Me About Success with Cameron Herold – EP 300

Justin Donald: Well, hey, Cameron. Good to have you back on the show for round two. I'm glad you're here in Austin hanging out and maybe making this a home base in the US.

Cameron Herold: Yeah, maybe for sure. My wife and I are looking at this as our forever home in the US market.

Justin Donald: I love it.

Cameron Herold: Too many reasons.

Justin Donald: So, we have to talk real quick. I mean, we got all kinds of things we can get into, but you've spent five years now traveling. You sold everything five years ago, whatever you could fit in a suitcase or two, and that's it. And so, you've been country to country to country for five years. I think I've been to 94 countries, but in the last five years, I think you've gotten to almost that number.

Cameron Herold: We've done 80 in the last five years.

Justin Donald: Wow.

Cameron Herold: Yeah, it's crazy town. And some of them, seven or eight times. Like, I've been to Dubai 10 times, Italy seven times. We've been moving a lot.

Justin Donald: That is incredible. So, what are the biggest takeaways from that, from like life of you had a home in Canada, in Vancouver, you had a home in Scottsdale, and obviously you'd done other travel and have other toys, and all that. But you sold it all. So, are there lessons or things you've learned, or was there this purging of material possessions, and you're like, "Oh wow, I actually don't miss it as much as I thought"?

Cameron Herold: Yes to all of that. So, it's kind of like everything. There's the glass half full and the glass half empty. The getting rid of one big lesson was don't join a lot of golf clubs because I gave back my golf course membership in Vancouver. I gave back my one in Scottsdale. I gave back my tennis club. So, I walked away from all that money, which was crazy. And then you look at all the stuff that we had that is now gone, given away, gifted, sold on Facebook Marketplace, donated. I donated pretty much a full two-bedroom worth of stuff to an old landlord from 10 years before that I knew he was going through some financial trouble. I gave him a bedroom suite, a dining room suite, some office furniture, some carpeting, some kitchen stuff, and I just gave it to him as a thank you, because he'd really helped me out 10 years before. That felt really good.

You realize how little you need. And I think I had 12 or 13 belts. Now, I have a brown one and a blue one, for real. I have three long-sleeve shirts. I used to have closets filled with clothes. So, the hard part was getting rid of stuff that there was an emotional tie to, like photo albums. We took all the ones we liked and had them digitized and then threw out dozens and dozens of photo albums. Family heirlooms. It was which ones do you keep, and which ones do you throw away? And then silly things like I loved my wine glass collection that I had, or I liked my cookbook collection that I had. You throw it all out. You give it all away. And then being down to, so that part was hard and good at the same time.

The other thing that's really hard right now is having any feeling of awe, like any feeling of comfort, like if you go home at the end of the day, you can sit in your comfy couch, you lie in a bed, you like your pillows, right? I think I've done 180 Airbnbs in the last five years.

Justin Donald: Oh, my goodness.

Cameron Herold: So, I've never had a comfortable pillow, right? And friends, like, you've got friends that you can call on. I have to find a new friend group pretty much every week. So, that's been hard, as well as exciting.

Justin Donald: That's interesting. So, moving forward, you're potentially going to make this a home base. Somewhere in the US, you're going to have a home base. I hope it's Austin. I'd love to see more of you. What does that look like? Like, how much are you here versus how much are you traveling?

Cameron Herold: Well, so I'm a Canadian citizen. My tax base is Dubai. My company is based in Dubai. I'm a Dubai resident, but I only have to go, I have a golden Visa, I only need to go one day over a 10-year period. So, now I'm legally only allowed to be in the US 120 days a year. Otherwise, I'll trip over their tax rules, and I can only be in Canada 180 days a year. So, buying a place in the US, it would be three to four months a year. I love it here. I've got lots of friends here. I like the lifestyle here. There's too much going on in Austin, but I won't be in one place forever. So, we're looking at probably Northern Italy as a place, and then a place in New Zealand called Wanaka as their Southern Hemisphere. And look to have three homes that we would kind of rotate time through, and then still do bucket list activities and trips, and some adventure travel.

Justin Donald: Sounds like an epic lifestyle. I love it. All right. So, in order to get here, there are successes, obviously, but what people don't normally talk about are the failures, and often there are more failures than successes, and I think it'd be really fun to get into that.

Cameron Herold: Get into it? All right. So, I've been talking a little bit recently with some friends about failure, and I realized that there's not a single entrepreneur who I've ever met that will talk about the failure online on social media in the moment that they're in the actual failure. Right? We're not going to talk about being robbed or theft or embezzled or firing our best friend or not being able to meet payroll or the marketing campaign that didn't work, or not enough cash coming in, or arguing with the landlord. We never talk about any of those issues in the moment, because we're too vulnerable. So, we don't tell our employees, right? Sometimes we don't even tell our spouse, because we're really trying to panic through the fear.

And we live in this really compressed world, but we will go online and go, "Oh, here I am in Sicily on the ocean, having my beautiful life.” We talk about the good stuff, and then we'll talk about the stressful stuff a couple of years later when it's done. And I think it's because we have to protect our business, our investment. And then I've been interviewed so many times on social media but also doing live speaking events. I think I'm just getting tired of telling all the success stories, so, yeah, wanted to go and talk about some of the failures.

Justin Donald: Oh, I love it.

Cameron Herold: Where do you want to start, life or business, or all of it?

Justin Donald: Yeah. I mean, I think you know it's interesting, you would set up this talking about like you don't share the failures in the minute or in the moment, and I have these times where I'm like trying to think, like, "Yeah, small ones is easy to share. The big ones are really tough to share.” And some of it is like I have to emotionally come to grasp and come to terms with, like, what happened. And like the big stuff, it's like the first thing I want to do is blame someone else, like it's not my fault, it's someone else's fault, right? So, it's almost like you got to go through this process to you're like, "No, I need to own it. This was on me.” And then, more importantly, what did I learn from this, so that it never happens again?

Cameron Herold: So, I've always been good at the introspection, at blaming myself. I learned something when I was really young: that when you point your finger at someone, there are three fingers pointing back at you.

Justin Donald: That's right.

Cameron Herold: So, I've always been good at blaming myself for the problem, and I really beat myself up with that, but then I sit with that for a long time. And because I'm sitting with that, I tend to get depressed, or I get stressed, or I get a little anxious. I think we need to actually socialize that failure is part of the entrepreneurial journey, mostly because too many people are trying to be entrepreneurs that shouldn't. Too many people are trying to be entrepreneurs, thinking it's all about lying on the beach with your laptop and having a great life, or flying on a private jet, or driving your Lambo. Yeah, but there's a lot of pain that it takes to get to the night before.

Justin Donald: Yeah, 100%.

Cameron Herold: And then life is hard as well. I didn't realize how hard so many people are struggling with the normal day-to-day until probably seven or eight years ago. Like, I was in my early 50s when I realized that people didn't grow up in a life with a mom and dad together and family Christmases and family trips and brothers and sisters that loved each other, like I just didn't know. I don't know how I didn't know, and I think it's talking about that stuff that makes the humanity a little bit of a richer experience, that it's okay to go through the struggles. It's okay to be vulnerable. It's okay to say, “I don't really know how to do this stuff,” or, “I'm scared,” right?

And then we do talk about it like in our mastermind communities, if we have a coach, maybe, or a therapist, maybe, or a really, really close friend, but we're not sharing it on social, and I think we need to share it more, share the failures more, and then let's back it up to even sharing the failures in the moment more, and being okay with that.

Justin Donald: Totally. I agree 100%, and I think the failures are ultimately what define us, if we can allow the learning from it. And I always tell people, I make a lot of mistakes, I still make a ton of mistakes. My goal is just to not repeat the mistakes that I've made, right? Like, how do I get better, so I don't do that one over again, but there's going to then be something else, but I always share, like, from an investment standpoint, if I only did great in my investing, I would think that I'm better than I was.

Cameron Herold: You know what? So, I got my two kids involved in investing when they're 16. I went to my very first meeting with my stockbroker when I was 16. I'll talk to you about that, because I learned some good lessons at a young age. My two boys, when they started investing, I said I would guarantee their downside for the first three years, as long as they picked the stocks and they invested their money in them, and both of them picked one stock each that they didn't do that well on. And I'm really glad they did, because my oldest son actually picked NVIDIA six years ago and put a lot of money into NVIDIA six years ago, and he's done very, very well with NVIDIA. But he also picked the Gap, and he didn't do well with the Gap, but he learned about retail.

But I'm glad he had a failure, because if he'd only had a bunch of investments like NVIDIA, he'd be too kind of cavalier and too risky, right? So, I think failure is a good lesson. I remember being in Las Vegas when I was 18, and my dad gave me $100 to play blackjack with, and I lost $100 in six hands of blackjack. I had to split and double down a couple times, and I lost it all in six hands. This was 1981. I was sick to my stomach because like that was so much money. It’s still a lot of money. But it was so good that I lost that money, that now I'm just not cavalier with my.. I really don't gamble anymore, because I still feel that sickness of it, right?

Justin Donald: Totally, I love that. I love the perspective that you get when you lose, the pain of it.

Cameron Herold: A couple of my bad investments, I invested in a couple of mining companies in the 1980s.

Justin Donald: Oh, man.

Cameron Herold: And I could have done Apple or Microsoft.

Justin Donald: Oh, no.

Cameron Herold: Right? Why did I do mining companies? Because I grew up in a city of mining speculators. And then I…

Justin Donald: By the way, that's what it is, true speculation, right? The difference between investing and speculating.

Cameron Herold: And getting excited about the local entrepreneur. My dad was an entrepreneur, but he was a bit of a gullible entrepreneur, and he would like these people, and he would put money into their deals, always kind of hoping. And that was a good lesson for me to learn, right? Like, no, these aren't good investments, so now I only buy really good quality stuff. Then I got in, and I invested in this Atlantis Submarine sub-aquatics. They have these tourist subs all over the world that you can go for rides. What a horrible investment. But what was I doing putting $2,000 into this in 1986, $2,000 again in Microsoft, or something back then? And we knew Apple was going to be something, or even IBM, or a company like that.

Justin Donald: Yeah. Well, it's incredible. And by the way, not to beat a man when he's down, but one of our members invested in Microsoft years and years ago, probably around that time frame. And that one specific investment has single-handedly like put her in a very high net worth stratosphere, which is pretty cool to see. And she has never sold any ever. So, she has siblings that have sold. She's just held indefinitely and has done very well.

Cameron Herold: So, you might not like my investment portfolio. I'll tell you what it is, but it's based on having lost some money early and betting on things that were speculative. That's terrified me. So, I only have the stomach now to invest in what I still perceive as quality companies that are growth. So, I have 100% of my net worth, 16% is in Bitcoin. And then in my other 84%, it's 100% in Apple, NVIDIA, Microsoft, Google, Meta, Tesla, Uber. There's a couple of others that are in there, AMD, and just I'm literally in the core 10 tech stocks.

Justin Donald: Berkshire Hathaway?

Cameron Herold: None.

Justin Donald: Okay.

Cameron Herold: No, I'm literally in this…

Justin Donald: Just the tech.

Cameron Herold: That's it. And it's like they're not going away. They just keep printing money. They're buying up their entire market share right now. They're sitting on cash, and if all of a sudden there's a problem, I'll just sell and liquidate it all. But I just keep buying. If the stocks are down, I buy more. Like, if the stocks are down, I buy more. I get excited, but I'm just all in on those.

Justin Donald: Now, that is we've talked a lot about asset allocation in our mastermind community. But it's interesting because an entrepreneur's investor profiles can be a lot different than a traditional investor’s. It's going to be different, also, than a family office. And I think…

Cameron Herold: But you notice there's no real risk there.

Justin Donald: Well, it's funny that I was actually going to comment on that. To you, it feels like there's no risk.

Cameron Herold: Okay.

Justin Donald: I look at that, and I say, "Oh, my goodness, that is such a high-risk portfolio.”

Cameron Herold: Right, because you're all in on tech, right?

Justin Donald: Yes. And so, by the way, that doesn't mean it's not going to work out, but it is really funny, like when you're like, "Oh, well, this is, to me, safe and consistent and makes sense,” and I'm like, "Oh my goodness, I'm uncomfortable hearing about that. I like exposure to it, but…”

Cameron Herold: It’s a lot of exposure.

Justin Donald: Yeah, in moderation, for me.

Cameron Herold: Well, that's why we're looking at buying three homes so I can sell off some of my NVIDIA and Google, and I can invest in a couple of homes, so at least have some diversified a little bit. I'm in a good cash-earning year. Anyway, let's go back to some failures.

Justin Donald: Well, I love your Bitcoin position.

Cameron Herold: No more mining companies, anyway. No more mining companies.

Justin Donald: All right. So, yeah, let's talk. Let's get into some of your business failures, because I think that that's going to be the first place where we'll have a very relatable audience to some of these what maybe in the moment were catastrophes, but there's probably a lot of good that came from them. Just took time to realize it.

Cameron Herold: I'll go to one that just kind of came to mind, and it's a failure of kind of leadership. I just took myself for a long time too effing seriously, and I would show up being serious and driven and focused, and not enjoying the journey, not having fun. And I remember back to when I ran my first real company, I was 20 years old, I had 12 full-time employees, and I had five of my closest friends from college move five hours away to live in the city I grew up in, Sudbury.

Justin Donald: Wow. Side note, by the way, 40 years as an entrepreneur, I just want to make sure that the audience kind of has some reference here. So, this is like you kind of starting out, and I know you've done some stuff when you were younger, too, so I don't want to discount that. This is like real deal adult.

Cameron Herold: This was 12. I had 12 full-time income. We painted 78 houses that summer. So, when five of my friends moved to the city that I was in, their whole summer was working during the day, playing basketball, being out on my lake, on my windsurfer, hanging out, hanging out with my friends, going for beers, but I was working, and I was working, and I was working, and I don't remember having fun those three summers. And I remember losing my friendships. I remember my friends being there, and me feeling distant and disassociated, and not around them, and that was a real failure. It is, why did I take it so seriously that I forgot to enjoy the journey as well? You know, why would I lose relationships?

They did well, they made good money, but we weren't friends anymore, because I was playing businessperson, because it was so serious. So, I think that was a big one for me. And that's something I won't do anymore. I won't let business get in the way of my friendships and my relationships and my time with me and my time with my kids. That was a big one.

Justin Donald: I love that you started there, because I think that if we're being critical of ourselves, like the best area to improve in is exactly that, relationships, the things that are going to make a person the wealthiest that they can be is having those rich relationships. But sometimes it takes losing them or at least going through a process where it's the relationships in jeopardy, to recognize how valuable it is.

Cameron Herold: Yeah. I have another one on inspect what you expect that I would delegate, not abdicate, but I would delegate projects and metrics to people, responsibilities to people on the team, and just trust that they had it, and I missed the point that they didn't have the skills to necessarily make it happen, or they didn't have the time and the confidence to make it happen, and I just let things go too long and too far. So, at one point, we had 120 people in our call center, we had four full-time people managing and listening in on their calls, and we decided to call the call center one day to see how we were doing, and our calls sucked.

I mean, it took five or six seconds to pick up the call. We didn't wow the customer, didn't handle the objection, didn't ask for the order. They're terrible. So, we went into the office and asked the quality assurance team, "Can you show me what you listen in on when you do the calls?” They had an 86-point checklist for a three-minute phone call.

Justin Donald: Whoa.

Cameron Herold: Like, whoa. Who developed this?

Justin Donald: Are we majoring in the minors here?

Cameron Herold: Way majoring in the minors, right? And then somebody, and I can talk to that point. Then somebody said to me, “I don't think anyone's even using the quality assurance reports.” So, we asked the managers, "Hey, with all these reports you're getting, what do you do with them?” They said, "Nothing. They're drivel. There's way too much information there for us to even worry about.” But because we'd never looked at what people were doing in their roles, we had four full-time people producing work that no one was using, and our call center was struggling because we had never really inspected it. So, I learned to kind of, yeah, that whole saying of, "Inspect what you expect,” but that was a big lesson to learn when you have 120 people kind of going sideways for a whole year. That was a bad one. You talked about majoring in the minors.

Justin Donald: Yeah.

Cameron Herold: If I go back to 2002, so at 1-800-Got-Junk, I was the COO there, and one of my franchisees called me up. His name was Alan Reimer. He was our franchisee in Philadelphia, and I was on them in that particular week. As an entrepreneur, we see all the details, right, stuff that we could improve, stuff that's important. And what was driving me crazy was every franchisee was using a different email signature. I was pretty early in the email days, 2002, only seven years into email, but I wanted branded professional emails, and they all had different logos and different colors and fonts, and it was driving me bonkers. And he called me up, and he goes, "Cameron, you're majoring in the minors.” I'd never heard the saying before. I'm like, "What do you mean?”

He goes, “You're right, our email signatures suck. But do you know that you have 30 franchisees that have no marketing calendar, no marketing budget, no marketing plan, and you're worried about our email signature?”

Justin Donald: Wow.

Cameron Herold: He said, “Why don't you worry about what does matter?” And I was like, whoa, big lesson there too.

Justin Donald: That’s great.

Cameron Herold: But I'd have the humility of leadership to go, "Wow, you're really right.”

Justin Donald: You should be able to listen from one of your guys.

Cameron Herold: Yeah, not argue, and not argue for the point that that email signature was still wrong. It's irrelevant that it's wrong, because the bigger thing, right? So, that's the one thing, keep the one that keep the main thing the main thing.

Justin Donald: That's right.

Cameron Herold: That whole stuff is really powerful.

Justin Donald: Yeah, these are great lessons.

Cameron Herold: Want to hear how we almost bankrupted 1-800-Got-Junk?

Justin Donald: I would love to. And by the way, what's funny is you may look at these as your failure, your situation. I guarantee, like, I hear this, and I'm like, "Ooh, that reminds me of this one time where I had an epic failure, very similar.” And so, I know as people are tuning in, they're going to have their own experiences that they can relate to this, so I love it. I think this is such a great topic.

Cameron Herold: I hope so because it feels horrible talking about them. It's not like I'm used to standing on stage talking about here are all our good successes and how you build it, but maybe there are some lessons in the failure.

Justin Donald: Yeah, I think there are, and people know your lifestyle. They know you've done well enough to have recovered from all this, so.

Cameron Herold: Well, there are some hard parts in the moment, so.

Justin Donald: You always learn the most from the hard parts. You always do. You realize how human you are and how easy it is to make mistakes, how blinded you can be by other things, how inexperienced we are, how little we actually know.

Cameron Herold: Yeah, we're all still growing, man. We're all still growing. Every day, this is the biggest thing we've ever done, too, right? Every day, the company gets bigger. It's like pushing a snowball up a hill. It's tough. So, 1-800-Got-Junk, I was the chief operating officer. We had about 3,000 employees system-wide. We were operating in 330 cities, four countries. It's been massive, huge business. And our VP of Finance came up to me one day, and he said, "Are you sure we're not growing too quickly? You sure we're not opening up too many locations?” And I was like, "No, no, we got this.” And he goes, "Okay.” And he kind of walked back to his area, and we kept plowing forward.

And about three months later, we had a new CFO joining us, and she had been the CFO at Business Objects, a huge, huge company, billion dollar company, and she basically pulled the fire alarm one day and said, "We're going bankrupt.” We’re like, "What do you mean we're going bankrupt? We're growing like crazy. We're the number two company in Canada. We've doubled our revenue six years in a row.” She said, "We're running out of cash. I'm like, "Well, we've got $5 million in the bank.” She goes, "No, you had $5 million in the bank. We'd spent $2 million on an office renovation and a move. We'd spent $800,000 on employee bonuses, $600,000 on taxes, $400,000 on a glass stairway to connect the three floors together, and we drained the $5 million in our bank.”

I'm like, "No big deal. Let's just go ask the bank for a credit line, look how good we are.” Because we had no credit line, no loans, nothing. We'd built the entire company off cash flow. We went to the bank, and the bank said, "We can't loan to you.” We're like, "Why not? Look how good we are.” They're like, "You don't know how to run a company.” We're like, "Sure, we do. Look how big we are.” They're like, "No, you don't understand how to leverage the balance sheet. You don’t understand cash flow. You don't understand budgeting.” We're like, "Sure, we do.” They’re like, "Well, if you had, you wouldn't have spent all the money.” We’re like, “Well, we didn't need your money because we had all the money.”

Like, we were so naive in understanding. They said, "If you'd come to us when you had 5 million in the bank, we would have loaned you 5 million, but we're not loaning you a penny.” So, Brian, the founder, had to go to his mom and borrow $420,000 to meet payroll.

Justin Donald: Oh, my goodness.

Cameron Herold: The next day, we paid everybody. Then we fired 30 people out of the 248 at the head office. Then I spent two weeks phoning all of our vendors, telling them they weren't getting paid for 90 days. We didn't pay ourselves expenses. We cut the leadership team's pay. Like, we went into full-on scramble mode because we'd almost bankrupted the business.

Justin Donald: That's scary.

Cameron Herold: And the big lesson I got from that was if you're not willing to listen to your team, like your VP of finance, hire someone you're willing to listen to, but God gave us two ears and one mouth, and we need to use them in that ratio. Now, Facebook was just starting that same month, that was like early 2007, so we weren't really on social media because it didn't exist. But I'll tell you, I would not have been on social media talking about the problem in the middle of the problem.

Justin Donald: That’s right. Yeah, you could sink the company indefinitely. That is permanent loss if you do that. So, I do get why sometimes we need to, in the moment, not share these.

Cameron Herold: Yeah. It's brutal.

Justin Donald: Yeah, the full transparency of what's happening. Maybe, let's punt it down the road a little ways.

Cameron Herold: I'll talk about health?

Justin Donald: Yeah, while we’re on it.

Cameron Herold: I got lots of failures.

Justin Donald: Let’s hear them all. Yeah, this is great.

Cameron Herold: So, you're healthy. I'm healthier now. I used to weigh 40 pounds heavier than I do today.

Justin Donald: Well, you look great.

Cameron Herold: Thank you.

Justin Donald: Yeah, you look fantastic.

Cameron Herold: I'm 182 today. I was 222 pounds when this story happened. So, it was October.

Justin Donald: When was this?

Cameron Herold: October 2000. I have a picture. I was very, very obese.

Justin Donald: So, I didn't know you at this time, because I kept thinking to myself, I don't know you being that heavy.

Cameron Herold: Yeah, I know. I have really good course correction. So, it was October of 2000, and I was running an internet company in Seattle. We had 900 employees at the business, and one of the VPs turned to me. I was the head of corporate development, and he turned to me and said, "Are you okay?” And I turned around in the elevator and said, "Yeah, I'm fine.” And I collapsed on the floor of the elevator and started crying.

Justin Donald: Oh, my goodness.

Cameron Herold: And I was having a nervous breakdown.

Justin Donald: First one, I'm assuming, that you've ever had. You didn't even know what it was in the moment, right?

Cameron Herold: No. I just knew that I needed a drink and a cigarette, which I don't smoke, and I don't drink anymore, but I sure did then.

Justin Donald: Oh, my goodness.

Cameron Herold: So, I went to the doctor a couple weeks later, and my wife and I were buying a home, and I needed to get insurance for the mortgage, and you had to have a medical to get the insurance or something. So, I’m getting the medical, and the doctor goes, “What’s going on?” I go, “Not much. I’ve got this weird metallic taste at the back of my neck. It’s kind of like I’m chewing on tinfoil or something. It was this weird taste. It’s the best way I can describe it. My neck and shoulders were always tight, and I had this taste at the back of my neck.” And he goes, “What’s going on?” I go, “Not much.” I said, “You know, the stock market has crashed by 78%. The NASDAQ had crashed,” because it was the fall, October 2000.

And so, we lost our $64 million valuation. We’d sold the company for $64 million, but by that point, it was only worth three and a half, and we hadn’t been able to get out yet because we were public and there. And long story, we lost the company.

Justin Donald: Oh, my goodness.

Cameron Herold: And so, we’re firing 300 people of the 900.

Justin Donald: You lost the company.

Cameron Herold: We lost our $64 million. We were out at three.

Justin Donald: Oh, my goodness.

Cameron Herold: Yes. Whole story there. And I got married, but I realized I’m not in love, and my wife is pregnant, and I’m already trying to figure out how I can leave. And my mom’s dying, she’s stage 3B cancer. And we’re buying our first house, so that’s kind of cool. And I’m moving from Seattle up to Canada, so that’s kind of neat. And I’ve just quit my job and my wife has quit hers.

And the doctor’s like, “And there’s nothing going on?” I’m like, “No, everything’s good.” So, he gave me this test, and if you fill out all the points and if you have 150 points, you have a 50% chance of a heart attack. If you have 250 points, you have a 95% chance of a heart attack. I had 435 points.

Justin Donald: Oh, my goodness.

Cameron Herold: I was clinically redlining.

Justin Donald: And this is based on change and…

Cameron Herold: All the stuff that’s happening simultaneously. Yeah, like, losing all your money, losing your company, having a child, getting married two months before. I had 9 of the 10 most stressful events happening simultaneously.

Justin Donald: But isn’t it crazy, though, mentally, and I think a lot of us as entrepreneurs or at least Enneagram 7s, are like, “Yeah, everything’s fine.”

Cameron Herold: “No problem. Easy.”

Justin Donald: “We’ll get through it.”

Cameron Herold: Easy. Easy, easy, right? Because I would finish the day, I would be in the office by 7 because I had no life. I would work all day and feel really good about running the company because I had no life, no hobbies. I would smoke during the day. I even had booze at my desk, and I would, like, slide a little shot into my coffee once in a while. Then I would go for dinner. It was the height of the dotcom era, so we’d go to one of the best restaurants in the city. I’d start with two Manhattans, some red wine, and finish with Grand Marnier, and I’d go home at 8:30, 9 o’clock at night, have a cigarette, and go to sleep. And I did that every day of the week. And then I would drive back to Vancouver, where my wife was living. I was commuting between Vancouver and Seattle.

Justin Donald: Oh, my goodness.

Cameron Herold: And I thought everything was fine. So, when I had the nervous breakdown and then talked to the doctor, then I realized it wasn’t. So, then I started to change my diet and get healthy. But yeah, I almost lost, I think I probably almost lost everything.

Justin Donald: No kidding.

Cameron Herold: And that was just not being aware.

Justin Donald: Intense.

Cameron Herold: Yeah, it was brutal.

Justin Donald: But also, one of those things where it’s like, I think sometimes hard-charging alpha personalities, you can see it in men and women, but I think it’s often that you see it in these male entrepreneurs where it’s like you just put your head down, and you work.

Cameron Herold: And you go. And you know what else is weird?

Justin Donald: And you sweep this under the rug, and you just charge forward.

Cameron Herold: Because you don’t know any other way, but charging hard when we’re struggling isn’t the path. It’s hard to disconnect, but you don’t see that. So, that October, I was written up in The Wall Street Journal as one of four, they called us the supernovas, people whose careers had gone really far and flamed out with stress.

Justin Donald: Oh, no.

Cameron Herold: I was getting press about my stress coverage. That’s not a good thing to get press about. But yeah, I just didn’t know. I wasn’t aware. And now I have the signals. I catch myself being tight, right? Or I see myself going 100 miles an hour, or I realize I’m not going to the gym or I’m not doing yoga, or I’m not listening to music, or I’m not just, like, practicing self-care.

Justin Donald: Well, but you also have better boundaries, and you’re not back to back. So, you’re at a slow enough pace. You might go full force in a moment or in a thing, in a season.

Cameron Herold: Yeah, and then I disconnect.

Justin Donald: Right? But you’ve got strong boundaries around it, so you have the time and space to pause and kind of be introspective, like you said earlier.

Cameron Herold: Yeah, the boundaries I think have been key, and I really had to learn those. The other part was, and this was 2007, right, as I was leaving 1-800-GOT-JUNK. I was at a cocktail party, and one of the women that worked for me, her husband was on our board. And Jillian came up to me, and she goes, “Cameron, you know what? You’re effing boring.” And I was like, “What do you mean?” She goes, “All you talk about is work. It’s the only hobby you have. You have nothing of interest.” And I was like, “Wow, I’ve lost everything.”

I wasn’t doing any of my ho– I wasn’t playing golf. I wasn’t playing– well, they didn’t have pickleball or padel, but I wasn’t playing tennis, wasn’t hiking, really wasn’t skiing. Do you know that Brian and I had built 1-800-GOT-JUNK together. I ski raced until I was 21. He used to ski, and for the six and a half years that we built the company, I didn’t know that he ever skied.

Justin Donald: Oh, my goodness sakes.

Cameron Herold: And he didn’t know that I ever really skied.

Justin Donald: That’s crazy.

Cameron Herold: That’s dangerously on tilt, right?

Justin Donald: Yeah.

Cameron Herold: I didn’t go to festivals, wasn’t listening to music. Like, I just had no hobbies. And then I was sitting at a mastermind around 10 years ago with Dean Graziosi, big real estate investor, entrepreneur. And Dean and I ended up crying, just the two of us sitting, talking. We said, “How would you want your kids to describe you?” And Dean said, “Oh, as a successful entrepreneur, real estate, internet marketer, whatever.”

And I got choked up, and he goes, “Why are you crying?” I’m like, “I don’t want my kids to talk about what I do to make money, and I think that’s all they’ve got.” And that was a moment for me 10 years ago that the switch flipped a second time, where I realized I want, if someone asks my kids, “What does your dad do?” I want them to say, “He hikes, and he travels, and he hangs out with friends, and he plays golf, and he plays tennis, and he goes to Burning Man.” “Oh, what does he do to make money?” “Oh, yeah, he runs the COO Alliance, and he has a course. He’s a coach.” So, if you asked my kids today, “What does your dad do?” I guarantee they don’t talk about what I do to make money.

Justin Donald: That’s awesome.

Cameron Herold: But that was a real failure point again at 50.

Justin Donald: Yeah. What a great defining moment, though. Like, what a great pivot to have that realization. And by the way, thank goodness for a mastermind where you can actually be vulnerable and get down to the root cause or at least have the time and space and the people that allow you to have the clarity that you have to make big changes in life.

Cameron Herold: It’s fun, right?

Justin Donald: It is.

Cameron Herold: You play pickleball, I can tell.

Justin Donald: I love pickleball.

Cameron Herold: I thought so.

Justin Donald: Yeah. And I’m newly into padel.

Cameron Herold: Padel’s great, right?

Justin Donald: It is. It’s a lot of fun. It’s a different strategy. I’m figuring it out.

Cameron Herold: And by the way, for everybody who’s watching right now, if you’re in the United States, you can call it paddle. If you’re in Europe, you call it padel. If you’re in the United States, you call it Ibiza. If you’re in Europe, you call it Ibitha.

Justin Donald: Perfect. Hey…

Cameron Herold: Ibitha playing padel. Ibiza playing paddle.

Justin Donald: That’s the age-old question here is, is it paddle or padel? And I’ve heard it both ways, so I like…

Cameron Herold: It depends on where you are, tomato, tomato.

Justin Donald: I like it. Like, I’ve got a good group here that plays both pickleball and paddle, so.

Cameron Herold: Well, and if you do that property investment with Brad, you’re going to have a pickleball court right next door to you.

Justin Donald: That sounds really nice to me, yeah. Yeah, lot on the horizon here. A lot on the horizon. So, we could obviously go dive deeper into losses and tragedies and failures, but would you say that there are certain takeaways? You’ve shared some, as you’ve pivoted from, hey, this failure, and…

Cameron Herold: Yeah, what are the lessons from it all?

Justin Donald: This is the change. But yeah, are there any key lessons that really stand out? Like, I love the defining moment and that shift with your family, with your kids, and being able to basically say, “My dad is not his business. My dad is–” right?

Cameron Herold: Some of the key lessons, well, this is one. I got it tattooed on me to remind me. So, this is the Ram Dass quote, “Walking each other home.” It’s in Hindi, but it’s a reminder that none of this matters, right? That we’re just doing this and taking care of each other until we die, so we may as well enjoy the journey. That’s been a big lesson for me, a big defining moment for me, is just to remember that don’t get so wrapped up in the day-to-day of the business, to enjoy the whole journey. To be more human with the people that I’m with and realize that they’re all struggling, that we’re all struggling, has been a big lesson. The listening more than I talk and being more curious has been a big lesson.

Justin Donald: That’s good.

Cameron Herold: Really listening, really caring about my employees. Not about their dog’s name and their birthdays, but, like, who they are and the humanity of who they are, and really, really caring about them because all this other stuff will take care of itself later, I guess has been a big one. Living within my means. Really living within my means. Like, I’ve invested 15% or 20% of everything I’ve ever made all the time. I’m excited about it and I’ve got my kids doing it, but I don’t need to have all the TVs. And do you know that I only bought my first pair of nice jeans about seven years ago?

Justin Donald: Wow.

Cameron Herold: I was just Levi’s until I was 53, because it was like, “I don’t need to spend $300 on a pair of jeans when these $100 Levi’s are quite good,” right?

Justin Donald: Yeah.

Cameron Herold: But then because I was investing, then now I’ve got money that I’m sitting there that I can kind of play with a little bit. So, that was a big one.

Justin Donald: You know, it might be fun. We had talked off-camera a little bit about even some investment moves, not necessarily failures, could be failures, but just some investment things that you’ve picked up over the years. We got into it a little bit. I don’t know if there’s anything else that you want to share with that, that could be fun for our specific audience, because people that tune in here, they love the entrepreneurship journey, they love the idea even of transitioning in many cases from W-2 to entrepreneurship or side gigging.

But then I think the masses, and we got people on both sides of the aisle, right? We’ve got corporate America, we’ve got entrepreneurship. But I think everyone’s really interested in investing, Lifestyle Investor type of income to cover life, that sort of thing. Like, how do we make good choices around money, investing, cash flow, etc.?

Cameron Herold: So, let me, I’ll give you some thoughts around it that I think are really applicable for everybody who’s listening or watching. We have to make it very normal to talk about money.

Justin Donald: Yes. Completely agree.

Cameron Herold: And it’s scary to me how few people do and how few people know about it. So, my assistant, who’s been working with me for 10 years, I finally got her investing, but she only told me three years ago that no one had ever taught her. She’s like, “My dad didn’t know. My mom didn’t know. We didn’t talk about it in school. My friends are embarrassed to talk about it, so we just didn’t know what to do.”

Justin Donald: Oh, man.

Cameron Herold: I didn’t know that. I didn’t understand that. So, now I’m spending time with all of my employees, with all of my nieces and nephews, setting them up and showing them what dollar cost averaging means so they can buy. Like, if you have a really good stock and it goes down in price, don’t sell. Get excited and buy more of it. Like, something good is on sale.

Justin Donald: Yes.

Cameron Herold: Like, if you’re going to buy a Porsche and the Porsche is 30% off, go buy the Porsche. It’s on sale, right? It’s a good brand.

Justin Donald: Totally.

Cameron Herold: So, get excited about dollar cost averaging. And then teaching them about compound growth. So, I built a little spreadsheet. I can share it with you and we can share it with people.

Justin Donald: The eighth wonder of the world, according to Warren Buffett, right?

Cameron Herold: But people don’t really see it, right? So, you’ll say it, so I built a spreadsheet to show it and how it works.

Justin Donald: I like that. Most people are visually oriented, so it’s powerful.

Cameron Herold: Well, the spreadsheet shows if you invest $10,000 a year from the time that you’re 20 until the time that you’re 30, okay? Just 10 grand a year for 10 years, starting at 20, and you get 10% growth. By the time you’re 60, you’ll have $3.2 million just because of the normal compound growth of starting at 20. Now, if you start at 30 and you invest $10,000 a year for 30 years, so you’ve invested three times as much, you’ll only have $2.2 million by the time you’re 60. That’s crazy.

Justin Donald: That’s a big difference.

Cameron Herold: I showed that to my nieces and nephews when they were between 13 and 18 years old. They’re just like, “Can we start now?” So, I’m like, “Yes, we can start now.” So, then what I said is, “Pick three stocks. They have to be good ones. You have to tell me why you’re buying them. And if you buy them and hold them for three years, I will guarantee you, you have no less than what you put in.” So, they all invested. I guaranteed their downside. And they’re all now excited about investing.

Justin Donald: By the way, I love that, guaranteed their downside. Can you just elaborate on that? Because I think there are a lot of parents that’ll tune in that I hope you just copy this. Like, this is a great strategy that builds confidence for kids or people.

Cameron Herold: Or adults. So, I did it with my sister.

Justin Donald: Don’t invest. They don’t know this world.

Cameron Herold: So, two years ago, I said to my sister, “You still don’t have Bitcoin, and I’ve been talking about it since 2014. Like, how is it possible?” I have a Facebook post in 2014 saying I was accepting Bitcoin. “How is it possible that it was 2024 and you don’t have any?” She goes, “I don’t understand it. I’m scared.” She’s an entrepreneur who’d run her own company for 28 years, owns lots of real estate. She was scared about Bitcoin.

So, I said, “Here’s the deal. If you invest $25,000, but it has to be $5,000 a week for the next five weeks because I want you to learn dollar cost averaging. At the end, as long as you hold it until 2030, December 31st, 2030, then I will guarantee that you have at least $25,000. If it goes to 20, if it goes to 15, it goes to 10, I will at least make sure that you have at least 25 grand. And if it goes up, anything that goes above 25, I get 10%.” She goes, “Done. Let’s do it.” I’m like, “Great.”

Justin Donald: That’s awesome.

Cameron Herold: I did that for each of my nieces and nephews. So, the guaranteeing the downside means is whatever you invest, I’ll guarantee that after three years you have at least that much money. Okay?

Justin Donald: That’s awesome.

Cameron Herold: But you can’t sell your stocks.

Justin Donald: I love that.

Cameron Herold: You got to watch the pain.

Justin Donald: Got to hold it.

Cameron Herold: Because I want them, even if they lose, I want them to know, oh, why did– like, my sister bought Peloton five years ago. I’m like, that’s a stupid business. It’s a good hype. It’s a cool brand. It’s a horribly run company, and what happens? She loses 90%, right?

Justin Donald: It looked like everything was going great during COVID.

Cameron Herold: Not when you look at the P&L.

Justin Donald: Okay, yeah, yeah.

Cameron Herold: Right?

Justin Donald: So, by the way, this is a good distinction.

Cameron Herold: They had raised money.

Justin Donald: Of why you’re investing. So, you’re talking about going heavy in tech, but also, this tech that you’re talking about is very cash flow positive.

Cameron Herold: Correct. I’m looking at very fundamentally strong companies. Apple and Google. Google is sitting on so much money it’s disgusting.

Justin Donald: That’s right.

Cameron Herold: Google now is literally starting to own the AI sector. They’re not going to go away, right? Put money in. And if all of a sudden, we wake up one morning and find out, oh, they’re the new IBM and they’re going to go, then sell it all. But, like, why do I want to bet in some hype speculative stock? I don’t– anyway.

Justin Donald: Oh, I love it.

Cameron Herold: But let’s talk about that at dinner.

Justin Donald: That’s right.

Cameron Herold: Let’s talk with our friends about it. So, I learned this at a group called GoBundance. The founders are from here, right?

Justin Donald: That’s right.

Cameron Herold: You know them.

Justin Donald: Love them, yes.

Cameron Herold: Mike McCarthy and Dave Osborne.

Justin Donald: Had them both on the podcast. Love them both dearly.

Cameron Herold: So, I was at one of their events 10 years ago. And at one of the dinners, I was in one of the VIP dinners, they were all passing around their financial statements. And I was like, “What are you doing?” They go, “We’re showing each other our stock, our investment accounts.” I’m like, “Oh, my God, there’s no posers. Like, everyone is telling the truth. Everybody’s showing, everybody’s learning.” I’m like, “That’s so powerful. But why don’t we do that with our friends and family?” So, I started that 10 years ago when I started GoBundance with my brother and my sister and my dad.

Justin Donald: That’s so cool.

Cameron Herold: And every December 31st, we show each other our growth for the year.

Justin Donald: That is so great.

Cameron Herold: And it’s hard when my brother still gets 3.4%, but he’s starting to see when I’m getting 26, 18, 27, and he’s going, “Oh, sh*t. Can you teach me?”

Justin Donald: Well, if you’re not doing this, then what he’s doing just, it will be the thing that he does. He has no comparison, right?

Cameron Herold: And he doesn’t know, right? Because he’s scared.

Justin Donald: Doesn’t know. He’s afraid.

Cameron Herold: And no one teaches him.

Justin Donald: That’s right. He doesn’t know how to do it, doesn’t know how to allocate into different things, but now, he’s got the comparison and you see a huge difference. I mean, that’s a motivator.

Cameron Herold: So, I was coaching a company recently, a CEO of a company, and they’ve got about 500 employees, and he said, “You know what I’m really proud of is we have a 401(k) matching program for our employees. So, anything they invest, I invest the same.” I said, “It’s terrible.” He said, “Why is it terrible?” I said, “Because you’re not teaching them anything. What I want you to do is teach them about dollar cost averaging, teach them about compound growth, teach them about buying a house and renting, teach them about controlling their own cash flow, teach them about having a personal budget. If in addition to that, you want to do a 401(k) matching, go for it. But why don’t you teach them about managing their financials?”

Justin Donald: I love that.

Cameron Herold: And he’s like, “Oh, my God, I never even thought about it.”

Justin Donald: It’d be interesting even to check the stats of, okay, what percentage of these 500 employees are actually utilizing the full match, right?

Cameron Herold: And even if they’re using it, they still don’t understand it.

Justin Donald: They don’t know it.

Cameron Herold: They’re not excited about it.

Justin Donald: I’m actually curious on participation rate.

Cameron Herold: Yeah.

Justin Donald: Is it like, so I hear a lot of people are like, “We got a matching program.”

Cameron Herold: It’d be very low.

Justin Donald: It’d be super low. And it’s also…

Cameron Herold: And because, but you know what? Those people have five TVs at their home when they only need two. Remember when you were growing up, you’re a little younger than I am, a lot younger probably. What are you, 50?

Justin Donald: Yeah. I’ll be 46 here next month.

Cameron Herold: Okay. So, when you were growing up, you had flat screen TVs already. We didn’t. We had one television. I was the remote control. I had to lie on the floor and turn the channel.

Justin Donald: We definitely had the big TV growing up. Yeah, yeah, yeah.

Cameron Herold: We had one television for a family of five, right?

Justin Donald: That was us, too. Yeah.

Cameron Herold: Okay. Now, you’ve got one in the family room, one in the kitchen, one in the living room. You got one in each everybody’s bedroom. Like, you don’t need six televisions. What you need to be doing is investing for your retirement, investing for your kids’ education, investing so you can have cash flow, so you can quit your crappy job and enjoy your life, right?

Justin Donald: Cash flow. Invest for cash flow.

Cameron Herold: But no one teaches that.

Justin Donald: That’s right. By the way, I’m in 100% agreement that the other things should be taught. I would actually venture to guess, and maybe you can track this with the CEO if you’re still doing coaching with him, I would venture to guess the more that is taught outside of the matching program, the higher percentage of participation will be inside the matching program.

Cameron Herold: Yes, because then they get excited about it.

Justin Donald: That’s right.

Cameron Herold: Right?

Justin Donald: Yeah.

Cameron Herold: And they understand it. And then all of a sudden, because if you go out and you put $1,000 into your 401(k) and it grows by 10% one year, you’re not going to get excited because it’s only $1,100. But if you understand compound growth, you’re like, “Oh, my gosh, I’m one year into a $3 million program.”

Justin Donald: That’s right.

Cameron Herold: Right? But all of a sudden, it takes like five or six years before you see it. My 25-year-old right now…

Justin Donald: Nothing happens, and then all at once.

Cameron Herold: Yeah, exactly, because it’s like a snowball, I mean, you’re not in Austin, but up in Canada where I’m from and we make snowmen.

Justin Donald: I grew up in Chicago. I got it.

Cameron Herold: Okay, you get it. Remember when you’re rolling a snowball, it’s like, “I’m never going to get this snowman,” and then all of a sudden, the snowball just gets big?

Justin Donald: Huge.

Cameron Herold: That’s kind of like compound growth. But we need our employees and our kids and our friends and our families to see that. Yeah, so you got to get– I think we have to socialize it and make it okay to talk about it.

Justin Donald: I completely agree. I love your modeling of it, but yes, it cannot be taboo anymore. We have to be able to discuss it. So, when someone applies to Lifestyle Investor, there’s a pretty, deep intake form, and we ask– I mean, these are all questions that to me, like I want to know, our team wants to know, our member board wants to know so that we can make a good decision on someone getting in or not getting in, or maybe they should go into tribe of investors.

Cameron Herold: Oh, they can’t buy a membership.

Justin Donald: Or foundations. They know they cannot.

Cameron Herold: It has to be approved. I like this.

Justin Donald: They cannot, right? Because I didn’t start Lifestyle Investor to make money, right? I have all of our investments, so we’re good there. So, we’re kind of a one-stop shop in many regards for what we do and the criteria and how high it is and the fact that we say no.

Cameron Herold: You’re like the modern-day Tiger 21.

Justin Donald: Yes.

Cameron Herold: I like this.

Justin Donald: So, I’m super proud of what we’ve built, but after completing an application, the number of people that say, “That is the most I have ever shared on my finances. That is the most in-depth questions anyone’s ever asked me,” I mean, it’s just a type form, right? But it’s…

Cameron Herold: Why is it so scary or so weird? Like…

Justin Donald: I know.

Cameron Herold: Oh, don’t talk about money. Why?

Justin Donald: It makes me sad that…

Cameron Herold: I don’t want to talk about the Chicago Bears anymore.

Justin Donald: That’s the most. And by the way, sometimes it’s like my spouse doesn’t even know this. My family doesn’t know it. And by the way, I say this all, like I’m not trying to be judgmental, whatsoever. I’m sad that this is where we are that we can’t or don’t talk about these things because it’s never going to get better until we can talk.

Cameron Herold: My wife said to me three weeks ago when I was talking about her investment accounts, I’ve really helped her scale up her investments. I said something, she’s like, “I don’t really care.” I’m like, “No, I need you to care. I need you to care and understand. I’ll still watch it a couple times a day, but I need you to care and understand because it’s important.” And she’s like, “Okay, I will.”

Justin Donald: I love it.

Cameron Herold: You know?

Justin Donald: Well, this is a great wrapping point. I love what we’ve covered today. You have so many years of wisdom, 40 years on entrepreneurship, even more than that investing. Where can people learn more about you, Cameron?

Cameron Herold: Easiest place is the main website. It’s CameronHerold.com. It’s H-E-R-O-L-D, so CameronHerold.com. It has links to all of my books, my online course, my coaching, my podcast, YouTube channels, it’s all there.

Justin Donald: And give a plug for the COO Alliance too, because there’s no one else in the space that I know of that’s doing second in command the way that you are, and I think it’s brilliant for anyone who’s running a business that they have a place for their COO to go and learn and grow.

Cameron Herold: Sure. Did you and I originally meet at the Genius Network? Is that where we would’ve met? Or do you remember where we met?

Justin Donald: No, actually, we met through John Ruhlin, the late, great John Ruhlin, at an EO event in St. Louis.

Cameron Herold: Oh, my gosh. Wow.

Justin Donald: You came and spoke.

Cameron Herold: Yeah, I remember that.

Justin Donald: So, it was a long time ago. Yeah. So, it was not too long after he had wowed you with the package of clothing.

Cameron Herold: The Brooks Brothers clothing. Yeah, so you and I were both involved in mastermind communities. So, EO was my first mastermind I joined 30 years ago, and I’ve been in the Entrepreneurs’ Organization and Genius Network and Strategic Coach and Baby Bathwater and Warroom and GoBundance and Maverick, like, so many events, right? And I realized one day sitting at a Genius Network event 10 years ago that there were a lot of groups for entrepreneurs.

And then there were events for marketers and for lawyers and for accountants, and there was nothing for that second in command. So, I decided to start a group called the COO Alliance where no entrepreneurs are allowed, but their second– like, you would never be allowed to come to an event. But Ryan, I think Ryan Casey is your COO.

Justin Donald: That’s right.

Cameron Herold: So, Ryan could come to our events. Ryan can be a part of the mastermind, and Ryan would be surrounded by a bunch of other COOs. So, we started that community up for them so that they can grow their confidence and their connections and grow in their career and grow the companies they’re running.

Justin Donald: Yeah. So, where can people find more about that?

Cameron Herold: It’s all at the same Cameron Herold’s website or COOAlliance.com.

Justin Donald: Perfect. Well, hey, this has been fun. Thanks for coming into town. Glad we could do this live and in person. It’s never more fun than being in the same room.

Cameron Herold: Well, next time we’re doing pickleball.

Justin Donald: Yes, 100%. Maybe we can still get it in this time.

Cameron Herold: Not this, not good. Okay, bye. Appreciate it.

Justin Donald: Oh, one last thing, I love ending every episode with a question for our audience. So, if you’re watching this, if you’re listening to this, what is one thing that you can take today, one step that you can move towards financial freedom and passive income and living the life that you truly desire on your terms? Most people live life by default. This is a challenge to live life by design and really build a life that you desire to be in. So, find something, pick something from Cameron today, and put it into action to move closer to your dreams. Thanks, and we’ll catch you next week.

Cameron Herold: Love it.