Hard Work Isn't Everything in Entrepreneurship | Cameron Herold (Podcast 302)

The role of the CEO is to make the CEO look good, right? It's to shine the spotlight on the CEO, to make them iconic. And then behind the scenes, the CEO's job is to shine the spotlight on the CEO, to say things like, hey, they have to be the hard. I need them to roll out the tough decisions. So you're constantly making each other look good. Today, I'm excited to share a special conversation I had with the host of Entrepreneurs on Fire, John Lee Dumas. Together, we delved into the essence of the entrepreneurial journey, emphasizing the need to truly savor each moment, embrace laughter, and prioritize those who mean the most to us. After all, isn't our work just a way to pay the bills? During our chat, we explored the role of the second in command, highlighting the importance of complementing the entrepreneur's strengths and weaknesses. I also shared my perspective on the significance of truly understanding and committing to your company's core values and the necessity of ensuring that your CEO is as passionate about these values as you are. In this episode, you'll get insights on my belief that success isn't just about hard work, but more about working smart. The harmonious relationship between a CEO and CEO, which I like to think of as the yin and yang of a business. The trio of motivations that often inspire an entrepreneur to kickstart their venture. My personal tips on selecting the ideal COO for your organization. Wow. One thing that I guess most people would disagree with that I think is important to be successful, it's that you don't actually have to work hard to be successful, that you have to work smart. And I know that we probably know that to be true, but I actually really mean it. We've all seen the fly trying to work really hard to get out the window, and it keeps kind of banging its head on the window. I was never the smartest kid in the school. In fact, I was a very, very average. I got kind of mid-60s, I think. I had a 2.3 GPA. So the harder I worked, the. The. The worse my grades always. So I realized very early on I didn't have to work hard. I had to figure out the cheat sheets. I had to find the shortcuts, I'd find the TA that could help me. I had to find the kids that helped me figure it out. I had to pay people to do some assignments. And I began this kind of learning that it was about being the finding the shortcuts, finding the easier path. So my R and D stands for rip off and duplicate I find the companies that have done a great job with a lot of really great things, and I just do what they're doing because for me, momentum creates momentum, not perfection. And not being the smartest person in the room and not working hard, well.

Whatever you're doing is working. I just want to know, first off, why do we want our second in command to have any power whatsoever?

Well, really, at the end of the day, they're almost our yin and yang, right? As the entrepreneur, as the CEO of a company, we need someone who can leverage us, who can take a lot of the stuff off our plate that's serving us, that is draining us of energy that maybe we're not great at so that we can spend more time working in our unique ability. We need that kind of MVP and partner to really help us make our dreams happen. I think it was Thomas Edison who said, vision without execution is hallucination. And many of these were both one. And your entire tribe is the entrepreneurs. We have all these amazing ideas, but we don't necessarily have the skills or the time or the bandwidth or the money even to put all that stuff in place. So the second command can help us get that stuff done, can help us get to our vision faster, and they can also free up our time to give us a life, right at the end of the day, we only start a company for one of three reasons. To give us money to give us time, or to put our flag in the ground, or put a stake in the ground to say that we did it, if we, if we've done it, if we're feeling good, that we're feeling proud, that we've built a business and we've got enough cash coming in, well, then getting that second in command can actually give you a bunch of free time back so that you can actually engage in everything else that's important in life.

I've interviewed over 30, 800 successful entrepreneurs now, and I can tell you by far the reason most people became an entrepreneur was because they wanted freedom. Not because they wanted to be chained to a desk or chained to a computer or chained to whatever new job or prison they're going to create. They wanted time, freedom, location, freedom. Cameron, what is a COO and what is their point of existence? Work wise?

I have an organization called the COO alliance and I run a podcast called the Second In Command Podcast. And the reason for me calling my newest book the Second In Command, what I called it was you could have a second in command that might be an operations manager or maybe a director of Ops or a VP of Operations. Maybe it's a president or a general manager or a coo. The higher the title usually denotes more responsibility, more autonomy in the role that they're in and a higher level of strategy that they can bring into the business and usually a higher level of wisdom and experience of having been there. Sadly, over the last 20 years, many, many entrepreneurial companies have given out titles that are far too big, far too early. And they end up putting these titles on people that they call them a COO, but they're paying them 120 grand a year. That's at best a director of operations. And what happens is these employees of yours end up going out and they do salary searches on Indeed and Glassdoor, or they just go out and Google like, what should a COO make? Oh, a coo should make 350 grand a year. Why am I being paid 120? Well, because you're not really a COO. So the question I guess is really, what's a second in command? The second in command has to be really good at the stuff that the entrepreneur sucks at. The second in command has to really love to work on the areas that drain the CEO or drain the entrepreneur of energy. And that's the real counterbalance in the yin and yang. So it's very different of the COO role versus other C level or heads of business areas where you could take the head of marketing for most companies and they could be the head of marketing for another company, or you could take the head of finance, whether it's a cfo, VP of finance, and they could probably be the head of finance for most companies. The reason the COO role or the second in command is so different is we have to be the balance for everything that the entrepreneur is not good at. So I would have been a horrible COO for most of our members of the COO alliance, most of their companies, because I wouldn't be a great balance for their CEO. And then the last part of this is I think a second command is there for a reason or a season, but not necessarily the lifetime. And it's because as a company continues to scale, at some point it usually outstrips the skill level of that second in command. So I was a great COO for 1,800, got junk from 2 million to 100 million. But I would have been horrible from the 100 million to the billion mark. Just as their current COO, Eric Church, who's been there from about the 100 million to the 450 million mark, he would have been horrible in the first six years because he didn't have the right skill set for what was needed in the earlier stages. So there's a whole bunch of unique parts that make up this COO or second in command role.

So there's a lot that I love about this. I mean, one thing I think is really powerful for you is to look at Cameron. I mean, he could do pretty much anything at this stage in his career, but. But he chose to niche down and to focus on the second in command on the coo. I mean, he wrote a book about it, the Second in Command podcast about it, same name. And this is what successful entrepreneurs do. They discover a niche, they become the best at solving problems that exist in that niche, and then they just keep talking about it over and over again. So let's keep talking about it now, Cameron, because I want to know, how does Fire Nation know if they are in need of a coo?

Yeah, so what you start bumping up into anybody listening. If you feel a little bit overwhelmed in the day to day, that might mean you need a second in command. If you feel like you don't have enough time to work on the core projects, that might mean you need one. If you actually realize that you're too busy working in the business and you don't have time to grow your people either, to grow their skills, to mentor them, to coach them, to grow their confidence. If you're really just pushing to get stuff done, but you're not there growing and supporting your direct reports, that's usually a great indication that you might need a CEO as well. But before you go and hire the second in command, the first key role that you really need to make sure you have is an executive assistant. Right? It's that old line that if you don't have an executive assistant, you are one. First thing we need to do is get all the admin off of our plates to free up our time. But then if you really are bumping into those key points I pointed out, it's usually a great indication that that second in command can come and help you. Another kind of reason that you might need one is in a turnaround situation, maybe you're just acquiring a company and you're going through a large inflection point, or maybe you realize that you just have a team of people that you don't necessarily have the skill set to oversee and that can actually be a good point to bring in a second command as well.

Feeling overwhelmed, lacking time working in the business instead of on the Business I know a lot of people complain about. To me, this could be a reason why you need a coo. And if this quote doesn't strike your core, I don't know what will. If you don't have an executive assistant, you are one. I mean, think about that. Think about those words, Cameron. And obviously you've convinced me. I've had an executive assistant for years. I've had a CEO for a long time, but I want to be convinced as well. How can they find the right coo?

Yeah. So the way that you find them is first by understanding who you are. Right. So it's truly, truly understanding yourself as a leader. What areas of the business do you fire you up? Right. What areas do you get energized on when you work? What areas of the business drain you? What parts of your role or parts of the business do you have really good domain expertise that you love to work on and that you're really, really good at. And what areas of the business do you kind of suck at? And you start to divide and conquer up these roles a little bit. When you've divided them, you can start to see what that other person's going to be doing. So that's the starting point, is what are you going to do and what are they going to do? Secondly is to really understand and commit to your company's core values. Because you need to hire a second in command who comes in and will absolutely obsess over the same core values that you do in your organization. You don't want somebody who aspires to them, but someone who already lives those core values. And then third is you're looking for someone whose behavioral traits really match yours as the CEO. And you're not looking for someone with the same DNA as you. Right. You're not looking for someone with the same personality profile. Rather you're looking for someone whose behavioral traits complement yours. So if you're a very kind of scattered, big picture, super entrepreneurial, make it up on the fly CEO, you might want a CEO who is more detail oriented, more process oriented. If you're a CEO who's very technology minded, like a Tobias Luque from Shopify, who's very tech and it, you might want a COO who's very outward facing, very culture, biz, dev, PR and marketing, like Harley Finkelstein, the CEO at Shopify is. So it just really depends. It's first starting, what do I look like? Who am I as the CEO? And that shows me what I'm then out there looking for as that Second in command. The next thing that I try to do is write a job description that really massively polarizes anyone reading it so that half of the people that read the job description are like, there's no way I would want to work for you. Great. And then the other half are like, wow, this sounds like my total dream job. It sounds super challenging. This is exactly what I'm up for. And you can attract those people in like a magnet. And then it's all about sharing those job postings with search firms. Their best second in commands are never out looking for a job. They're not on industry job boards. They're not, you know, on Indeed or Glassdoor. They're not, you know, they're not even noticing jobs being posted on social media. You kind of need to get a couple of really good search firms engaged and you go and poach them. Just like a sports team has recruiters that are always trying to recruit people away from a hockey team. Nobody's out there looking where they're going to move to the hockey team or football team or baseball team.

A lot of things I love about that. The one thing that I wrote down that I think is a key repeater, be polarizing. You want people to be a yes or an absolute no. Like, that's just right off the bat. Because otherwise you're bringing the wrong person in if it's not one of those two. So think about this. Most entrepreneurs are type A individuals. If you're listening to this, you probably are. I am. Most of you are micromanagers. I have definitely been known to be that in the past. So, Cameron, how do we let go of the reins?

One of the things you want to do is let go, but you don't want to abdicate, right? You don't want to dump it on their plates and walk away and never check in. So one of the first things we need to do with the coo, especially when they come in from the external, right? So you have two types of coos. You have one that's an internal person that you're going to promote that's usually like an MVP or somebody you need to handcuff in the company. Or you have the external person that you're bringing in and they're coming in from the outside and they're coming in over top of a group of people that have already been there. So you need to make sure that you bring them into and get them started in that role, get them up to speed before you dump a lot of the areas onto their plate. You need to integrate them into the company, the culture. They get to know everybody. They spend a couple of months really, really learning the business and the industry and the people, and then you can slowly start to let go. But I like the saying of Inspect what you expect, that as the CEO, you're constantly kind of digging in and looking to see if the work is being done like you need it to be, versus you're just dumping it on their plate and hoping that it gets done.

So, Cameron, Captain Planet is known to say that with our powers combined, we can change the world. How can we work with our COO to optimize their strengths and as well as the overall business that we're running.

Treat it like a business marriage, right? Let's say that you're a husband and wife and you're raising a traditional family. It's really, how does the husband and wife get together to raise the family? Right? How do you divide and conquer on roles and responsibilities? How do you actually tag team and work to raise the kids? How do you have healthy communication in place that you build each other up and be each other's wings? How do you have good times to actually have good debate and argue and fight, but not in front of the children, right? To get some of that stress out in the debate. So it's creating a lot of those same systems are how you're going to get the most out of having a strong second in command. And then it's secondly, realizing the role of the CEO is to make the CEO look good, right? It's to shine the spotlight on the CEO, to make them iconic. And then behind the scenes, the CEO's job is to shine the spotlight on the CEO, to say things like, hey, they have to be the hard ass. I need them to roll out the tough decisions. So you're constantly making each other look good, Right? I remember when my dad would come home, my mom would be like, oh, you're in trouble. Go to your room, wait till your dad gets home. In two hours. I would sit there patiently waiting, knowing my dad was probably going to spank me. And then 30 minutes after the little spanking would happen, my mom would come into my bedroom and I'd be sitting there pissed off. And she'd say, you know, your dad loves you. He needs to be the bad cop. He needs to be able to show you this. So she was always covering for him and he was always covering for her.

Cameron, give us one wrap up. Key takeaway. You want to make sure walks off into the sunset thinking about tonight?

Yeah. This will rattle them. None of this actually matters. This is just what we do to make money. At the end of the day, we're all just walking each other home. So we got to enjoy the journey, have some fun, laugh a little bit, spend time with the people that matter most, because this is just what we do to pay our bills. Find people that already done what you want to do. Never be afraid to ask questions and ask for help when you need it. It's good to ask questions, you know, when you're doing well, you want to continue, but when you're struggling, if. If you could ask those questions and find somebody who has done it, I mean, you're going to be light years ahead. So to have the confidence to ask for help when you need it.