Mastering Team Growth with Guest: Cameron Herald
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The first big one is if you don't have an assistant, you are one. For anyone out there in that 1 to 10 to 20 employee zone, if you don't have an executive assistant, you're working on all these minimum wage jobs that drive you crazy and you suck at. Like if I owned your company and found out I was paying you 100 grand or 200 grand a year as a five-person company and you're doing $20 an hour tasks, I'd lose my shit.

My name's Rudy Moore, host of Living the Red Life podcast, and I'm here to change the way you see your life in your earpiece every single week. If you're ready to start living the red life, ditch the blue pill, take the red pill, join me in Wonderland and change your life. Guys, welcome back. Another episode of Living the Red Life with one of my close friends, someone I've known for a very long time, someone that supported me through all my growth, Cameron. Welcome to the show.

- And everybody says good friends, but you stayed in my home with your girlfriend. I don't know, you guys still together? - Now wife, yeah, now wife, yeah. - There you go, so yeah, you guys stayed in my home, gosh, five years ago probably, so yeah. - Yeah, it's not just an internet person I'm Facebook friends with, yes.

Exactly. And I mean, we were just discussing offline. You've known me kind of through my growth trajectory and I've, you know, always looked up to you and someone that kind of helps me and I always go to and listen to whenever it comes to the operations, the team side, all of those things. So it's a pleasure to have you on here today and helping all of my audience and

viewers and listeners on how to grow amazing teams, people and why that's really one of the big secrets to growing a business. So it would be good maybe just for those who don't know you to get a bit of your background for two minutes.

Sure. Yeah, I was groomed as an entrepreneur. I grew up in an entrepreneurial family where my dad ran his own company, as did both sets of grandparents. My brother and sister and I have all run our own companies for about the last 15 to 25 years. And then I also got involved with three companies as the second in command and helped grow those to very large businesses.

One went on to become the largest house painting company in the world. It was called College Pro Painters. Another went on to become the largest collision repair chain in the world called Gerber Auto Collision in the US and Boyd Auto Body in Canada. And then the third was called 1-800-GOT-JUNK. And I got involved with them as the 14th employee as their chief operating officer. And I grew them to 3,100 employees, went from 2 million to 106 million in revenue in six years.

And then I left that company 17 years ago now, which feels like only recently, but it was forever ago. And I started working with companies all over the world. I've coached companies in 28 countries. I've been paid to speak on every continent, including Antarctica. And I've written six books. And then a couple of years, I guess six years ago now, I launched an organization called the COO Alliance and then recently launched one called the Opspot, which is an online mastermind community for people in operations roles.

Yeah, and I mean, it's kind of cool because you, you know, are in this internet marketing, social media kind of mastermind world, but no one really talks about the people side so much, right? We're all here at these events talking about marketing, sales, marketing, promo, social. And then, and that's, you know, and that's great, right? To like 20, 30, 40 staff. And then as we were saying offline, now, you know, we float around that 100 staff mark.

And for me, I spend more time on the people because I can't get the initiatives across the line efficiently, right? The marketing is easy compared to the people to carry it through. So talk about that for a minute. Why is it so important? But so most people in our space, they just don't understand it.

It's not even just in your space, Rudy. It's in every company. I was sitting, this was eight years ago, I was sitting at the CEO of Sprint's office. I was coaching Marcelo Claret, who is the CEO of Sprint. And I was sitting in his office, just he and I, and he turned to me and he goes, when are people no longer going to be a problem? Like, you're the 80% largest company in the United States. People will always be the problem. So what's hard is that companies have to evolve

as they scale, very similar to us as humans. So as an example, how old are you? 32 now. Okay. So when you were two years old, you were Rudy. When you were 12, you were Rudy. When you were 22, you were Rudy. And when you're 32, you're Rudy. But you're a very different version of the same human. You couldn't have run your company as a two-year-old. You would have been horrible running it as a 12-year-old. And you probably would have screwed it all up as a 22-year-old.

So you've had to evolve and iterate as a person. Well, the companies change and I see them changing at every one and every three. So when you have one employee, when it's just you and you get three employees, you now got a couple of people you can divide and conquer. When you get to 10 people, you usually have someone managing some people for you when

When you get to 30 people, you probably have four or five people managing everyone and you're managing four or five people. When you go from 30 people to 100 people, you now have your first leadership team.

At 30, you've got a management team, but they're all rookies. They've really never done it before. They're trying their best. They're working their hardest. Often you've promoted them to their level of incompetency or their ceiling of complexity. When you get to 100, you're now bringing people in from the outside and then the politics start to come in and it gets a little tougher and then you go from the 100 to 300. So there's some iteration points that happen in a company.

I'm just listening to all that because it's kind of, you don't know, you know, we haven't connected as much in the last year or two because you've been busy traveling the world and stuff and living the life. But that's basically our story, right? And it's, you know, one of the things I say to my C-suite, we reflected a lot this last year. One of our biggest mistakes is that we, you know, recruit people, we try and promote from within and

then it backfires because then they're not good enough, then you can't demote them, right? And then it ruins the relationship. So that was one of the biggest lessons probably in the last two, three years I've noticed. Just because they're a great supervisor and designer doesn't mean they can handle the politics of a team of 10 and hiring and firing and discipline and the ops within that department.

Yeah, so the only way that a company can actually promote from within is if they are ahead of the curve on growing the skill sets of the people. So what tends to happen, let's say that you have a manager of, well, in your case, it would be a marketing manager, but that would be a bad example. Let's say you've got an operations manager or a customer service manager or a sales manager. If they're managing the business and you're a $3 million company, they can probably still do it when you're a 6 million.

they can probably do it as a 12 million, but it's almost impossible that they can still do their role as a $24 million company because after three doubles, it's almost eight, nine times bigger. It's just really, really different. So what tends to happen is you have to start growing the skill set around areas like situational leadership, coaching, delegation, running meetings, hiring, onboarding, and training of people.

handling conflict, messaging, all of the kind of soft, we call them the soft skills of leadership that you bring someone in from the outside, they're really good at all that, but they don't know the company. So then you have a cultural shift. So ideally what you want to do is grow the people before you need them to be competent in those roles, which means identifying emerging leaders early

And usually starting a year to 18 months before you need them to have the skills and start growing their skill sets and capacity so that when they get there, they're good at it. Almost like as a kid, you know, when we're being groomed by our mom and dad to kick us out of the house when we're in our 20s, they teach us how to do laundry when we're 12. They teach us how to clean the house. They teach us how to do yard work and how to shop for groceries and make eggs. So when we move out of the house, we're competent as a young adult.

That's kind of what we need to do with our emerging leaders. But what tends to happen is we go, let's promote Sally. She's been really good. And then, oh, Sally's struggling. Well, of course she's struggling because it's all completely new.

Yeah, yeah. And I think the other thing that is interesting to me is you talk about the entrepreneur growing, right, and how they're constantly changing. I found, too, that like me and maybe my C-suite that are more experienced, we've grown a lot faster and matured a lot faster than maybe some of the staff.

So I kind of noticed, you know, that famous saying, he who gets you there, you know, he who got you here won't get you there kind of thing. And it's not all the staff. It's kind of like you kind of see it, right? It's like starts to have spotlights on people. They were great when we were at 2 million, but now we're going to be at, you know, we're doing, we're at 20 million. They're not so great, right? As a department head or a head of tech or whatever, whatever it is. So that's been fascinating too. Yeah.

We identified a number that a mid-level manager can only take a company through two doubles in revenue. And Ben Horowitz, who wrote the hard thing about hard things, said you can only take them through one triple. So there's a kind of defined phase that you really have to be very cognizant of as a company.

Yeah, and when, you know, generally we almost double every year so that it becomes like every two or three years, right? It becomes this pattern. And what, so what would you say, you know, for entrepreneurs listening, they're trying to build their first team of 10, right? They're going to a million, a couple of million. You know, a lot of the people I work with, it's them trying to do a bit of everything. They bring in a couple of VAs, a couple of people on Upwork. How do they do it the right way with all of your years of experience?

The first thing is that in the early stage, in the first 10 people, you need to hire a bunch of people that are really good at doing lots of things but don't have deep domain expertise at one thing. Don't try to hire an expert because they probably don't have enough to do yet, but you need people that can manage others, can manage freelancers, can manage projects, can deliver. They're really comfortable with bobbing and weaving and kind of changing directions because as entrepreneurs, we tend to change directions very quickly in the early days.

They have to be good at managing ambiguity. They have to be good at managing kind of short timelines. And then you also have to teach the leadership team, your first couple of managers, to be very good at delegation. What tends to happen is that Parkinson's law says that work expands to fill the space that we give it.

So when we delegate projects to people, if we don't give them a small amount of time and a small amount of money, they're going to end up spending longer and spend more money than we anticipated they would. So there's a real kind of an art to it. It's actually one of the 12 modules in my Invest in Your Leaders course is delegations because nobody ever really learns it.

Yeah, we had to train our team leaders on that note to assign rough timelines per project and then actually build a system weekly where they're auditing the productivity of their team. Because I told you offline, we went to like 110, 120 people, but then...

because we were growing fast and we needed people working, but then we just weren't getting any more done because we didn't have the team leaders in the right C-suite at the time, or department heads at least at the time, managing those people. So then now we've kind of gone, okay, we've got to redo this. We went back a little, thinned out, and we still get as much done now with like 30 less staff, so you can do the maths on that. Most of these were USW2 in office people,

And now we're rebuilding the department heads and C-suite so we can kind of hopefully go to that next phase. Well, there's two big lessons in there. One is that every early stage manager's solution to every problem tends to be hire more people. And it's almost never the solution to the problem. But they're really not good at saying no yet.

They're not good at trying to get more done with less people faster. They're usually not good at automation or optimization of processes yet. So they tend to throw bodies at, and that only works if you're in India, right? Where you can hire 40 people for the cost of one person in Florida. So, and I'm not making light of it. I actually have clients that were in India and we just solve the problems differently over there. We literally throw bodies at problems.

So the second part of that is that we need to teach people how to delegate with a smaller timeline. And instead of telling an employee, I think it will only take you an hour. What we need to say is I only want you to spend an hour.

Very different, right? If someone was coming here to clean my home and I said, it'll only take you an hour to clean it, they'd be like, oh no, it's going to take all day. But if I said, I have friends coming in an hour, clean it in an hour, they'd be done and it would be pretty damn good in an hour, right? But it's not.

it's just a subtle difference in the wording and we need to teach our management team how to do that better the same with spending money right you could order a if i said hey rudy and i are getting together for dinner can you organize dinner for us my assistant might organize the best steak dinner with amazing wines and blah blah blah and i'm like wait i don't drink anymore rudy's going to the gym right afterwards we just wanted some healthy bowl that we could sit and kind of eat in my living room and then get going

but I didn't delegate it properly, right? So the onus is on the receiver. If you're delegating to people, it's your responsibility to learn how to delegate so you get back what you're expecting.

Yeah, and we've practiced a lot of that more recently where I've come in and been a little more structured and we kind of have this motto now where it's like a figure it out. Because when you first start doing this, they look at you white-faced like a ghost. Like, how's that possible to, you know, do the mastermind dinner for 100 people at this price? Or, you know, because the first restaurant they ring says it's not possible, right? And then normal people go, oh, really, it's not possible. I'm like, ring 20 more and then tell me if it's still not possible. Yeah.

So it's interesting because as entrepreneurs, I think we are so innovative and we make things happen and we figure it out and we assume wrongly that sometimes other people that we delegate to do that. So I think for the beginner entrepreneur, it's

building those parameters or those systems, right? That when, as they're building the team, it doesn't get too messy like we kind of experienced. So we're kind of, like I said, going backwards and building those parameters now. So what about, we talked about the one to 10. What about, you know, a lot of my clients and fans and members are a million going to 5 million and then maybe going to that 20, 30 staff level. What would you say for those people?

it's all about communication it's about collaboration it's about alignment it's about making sure that people are working on the right projects and that they're communicating well so that everyone knows what they're working on give you a really interesting example this is years ago we had our operations department working on a very key project for our franchisees and they almost got it to completion and they needed finance to integrate some of the projects so that the swipe card technology could work

And finance came back and said, we can't even look at it for the next four months. And they weren't exaggerating. They were integrating a brand new CRM, a brand new accounting system. There was no way they could touch this project because it was about 50 hours of work or 100 hours of work for them, which would have ballooned. But because operations never told finance it was coming, it wasn't finance's fault.

They didn't have the communication for everybody to know what everybody was working on. And that's something you really need when you're in that 30 plus employee zone is these skills to be able to communicate and collaborate and get alignment so that everybody knows the projects that everyone's working on and what business areas might need a little bit of your time. And then I also think that IT and marketing should only ever schedule 60% of their work week

to allow for the rest of the company to screw things up and keep saying to marketing, hey, can you just make this prettier? Hey, can you just tie this in? We end up needing an IT of the same way. We end up needing more of their time. So if they're fully scheduled, they're not going to be able to handle any of that additional work. Yeah, I love that. It's funny. We're actually thinking now this year we might build two teams.

for marketing tech, right? Because we've seen this where, especially because we have all these, we do a lot of celebrity partnerships now, my own brands, you know, doing a million a month or so, probably go to two million a month soon this year. So it's like, I kind of want like the team that work on the pre-built projects and the maintenance, and then you have this like more quick moving team that can be, hey, this celebrity is going to speak at a blah, blah, blah event, and we want an opt-in funnel for tomorrow, right? Because that's

we're constantly battling this zigzag so it's uh it's just yeah it's interesting you say that because i i really do see that true especially it depends how bad you are as an entrepreneur right i think that dictates it because we're usually at least me i'm pretty innovative and creative and

It's not necessarily bad. It can also be how fast your growth is. There's something called fast growth and then you're experiencing what's more hyper growth. Fast growth tends to be 25 to 50% a year. Hyper growth tends to be 100% more. We did six consecutive years of 100% growth. So you can't even blame the company. When the company is changing that quickly, it's just hard to actually be able to plan or be that strategic.

So what happens in product development and in software, there's a group that builds the current version. So let's say they're building version 14 of the iPhone or version 15, whatever we're on. There's another team that's working on version 16.

And when version 15 launches, most of those people go to start working on version 17. Some of the people stay and work on the bugs on version 15 while the version 16 team does the rollout. So they leapfrog over each other and they kind of leave a few behind to work on their work. And I think we need to bring some of that into the rest of the business areas in hypergrowth.

Yeah, I think I'm going to probably test it this year. So I'll see how it goes and maybe hit you up for some feedback. But what about, I would love to know now, we talked about earlier,

most entrepreneurs, they're so focused on socials and marketing, not the people team part. So I would love just, you know, we've talked about people a lot, but also ops and systems, right? Like what are some of the biggest just general tips to as we come towards the end of today, that if you're a young guy, like you could have taught me 10 years ago, the first big one is if you don't have an assistant,

you are one. For anyone out there in that 1 to 10 to 20 employee zone, if you don't have an executive assistant, you're working on all these minimum wage jobs that drive you crazy and you suck at. If I owned your company and found out I was paying you $100,000 or $200,000 a year as a five-person company and you're doing $20 an hour tasks, I'd lose my shit. You really have to get a lot of the admin off

And that frees you up to be strategic, to work on your team, to work on alignment, to grow people and to work on parts of the business that really fuel you and you're really good at. So that would be a key starting point. The second would probably be to really focus on growing the skill sets of people, because as your company scales, the skills of your people have to scale. It's why I called my course, Invest in Your Leaders. You have to find your emerging leaders and invest in their skill sets

so that as the company continues to grow, they can continue to actually give great results. Because if the company is two times bigger, their skills have to be two times better.

Yeah, I love that. What about for a lot of the beginners, operations and systems? Most of them don't know what that is, don't know how to do it. And then they don't hire a COO or a head of ops or whatever, right, for a long time. So how does an entrepreneur, you know, people join my mastermind for marketing, but half what we talk about is hiring ops systems, you know, HR, legal, all these random things. How do they start to learn and figure that stuff out?

Start in the earliest stages of hiring people who are really good at managing projects, really good at time management, and really good at integrations with automation like Zapier, right? Or that they're really good at actually leveraging the tech stack to be able to automate processes. You need to find people that are kind of the jack of all trades, master of none, but they're good at getting shit done. That's early stage operations. That's what will really help your company scale.

Great. And then last question. Well, second but last question. We've talked a lot about teams, operations, systems, but you've had an amazing career, amazing journey. You now have an amazing life as a nomad as well. What are some life lessons for people that are trying to balance this entrepreneurial thing, business thing and money thing? And also looking at your life, how you've built that freedom as well.

I think the big one is none of this shit actually matters. It's just what we do to make money and if we don't have fun along the way, at the end of the day, we do die. So that's the first one. And I was very unlucky. I didn't experience death until I was 35. So I was three years older than you when my mom died and she was the first person I ever knew who passed away.

And I wish that I'd been much younger to have appreciated how fragile life is to realize that it isn't just about work. That's number one. The second is to remember that every single person that works for us or with us as a supplier, an employee, a full-time contractor, whatever,

They're all struggling with something today. Every single one of them with a personal issue, a health issue, a medical issue, a money issue, a family issue. Everybody is struggling with this human condition. And if we can show up as a leader, really giving a shit about our people, as much as we care about our business and our brand and revenue and our goals and our metrics, if we actually care about them more than anybody else cares about them, they'll go through brick walls for us to build a company.

Sure. And I love that. And yeah, we actually kind of brought in a, you know, as much of a system, not to systematize it, but time to reflect and support on that, because I think we get so caught up in the

work, work, go, go, go, right? So we do as much as we can to dive into the individual. Like when we do our quarterly retreats, we don't just do goal setting for the company and all the revenues and stuff and ideas. We actually have a section on their life. What's their goal? What's their, you know, it's the little things like that. And I work well when I have structure. Like if I just say I'm going to do it, I get lost in the day to day. So we have weekly and biweekly structure for building those things out in the company because, yeah, it's easy.

It's easy to get caught up and forget about that, right? Especially because as an entrepreneur, I mean, you just like get on with it. But then you realize not everyone can do that. Well, let me give you the last one. Your wife's name is Amanda, right? Yeah. How often do you tell Amanda that you love her? Once a quarter? Once every couple of weeks? Yeah, yeah. I mean, less, more than once a quarter. Yeah, probably. It's probably multiple times a day.

Yeah, maybe once a day because I'm out all day, but at night, yeah. Over text messages, over email, at night. We tell our spouse we love them so frequently. As entrepreneurs, most entrepreneurs suck.

at showing that level of appreciation for our employees. And what happens is we keep showing our employees another goal, another project, more growth, where we're screwing up, fix this, fix that, move faster, grow this. And we think, oh, they know I love them. But if we ever said, oh, Amanda knows I love her, I'll tell her next quarter that I appreciate her. Dude, she'd be gone at that first argument that we have.

It's because we keep putting all those deposits and love bombing our spouse that we can work through the hard times. As entrepreneurs, we need to love bomb our employees with gratitude, with praise, with thanks, with celebrating the core values, with truly appreciating everything so that we can load them up with more and more and more of the growth. And one of the best examples I ever saw, and I'll leave with this, is one of the CEOs of Starbucks, his name was Howard Behar.

Howard would spend two hours every single Friday handwriting thank you notes to stores and employees every Friday. That was 5% of his normal work week. And this is the CEO of one of the biggest companies. But I was being mentored by the COO at Starbucks for a year and a half. And I got to meet Howard and watch the system. And I recognized how powerful it is when they just actually give a shit and say thank you. Yeah.

Yeah, I read that. I think that was in one of the books, right? And I actually started that myself. My old assistant in Tampa is there now, so I got out of it. But every Friday I would write it, not to all the shops or anything like that, but to just a few of the rock stars for that week and tell them why they were a rock star and what they'd done. And so I love little things like that because for me, I have to systematize it like that or I get too lost in the day to day. So

Yeah, that's awesome. So last question then.

I think, like I said at the start, what's fascinating to me is no one really teaches this. There's a million Facebook ad experts, social media gurus, webinars, blah, blah, blah. But you're the really only person I know in this industry that has the programs, the support, the team, the whole mastermind. So can you just for a minute before we wrap up, where do people find you and what are you doing there for people listening that are getting into those bigger team numbers and need this help?

Yeah, a couple places. So I launched a course called invest in your leaders, and they should all definitely check that out. It's all the 12 core leadership skills that any manager, director, anybody emerging to manage people should be going through. And it's really priced effectively. The second is I started a mastermind community called the op spot. And it's an online mastermind community for anybody that works in operations roles.

And then third is the COO Alliance and that's an exclusive community for second in commands. You need to do at least 5 million or greater in revenue just to qualify. So that's a great community. They can find everything on CameronHerald.com. Yeah, the first one I actually, I think it was a year or two ago I messaged you about it, but I had my two of my heads of ops go through it and I think I actually need to send some new people back for it. Super beneficial and it's, you know, anyone listening,

It's like my marketing course where it's like a curriculum university style and, you know, better than an MBA. I think this will be better than anything you could take on the systems art people side. So love that. And it's an easy way that people can start kind of diving in and learning a lot. So Cameron, super appreciate you being on and, uh,

I appreciate your kind of mentorship guidance and experience that you're sharing here. It's super powerful. And as everyone listening, as you grow and get into more and more of these problems, you'll realize how powerful it is. Just hopefully you'll apply it ahead of time instead of like most of the stupid entrepreneurs that make all the mistakes and then go, oh, damn it, we should have listened the first time. I'm very guilty of that. So guys, thank you. Cameron, thank you. Awesome to see you again. Keep living the red life, everyone. I'll see you soon. Take care.

Bye.