10 years as CEO has taught me every owner struggles with this.

Managing the leadership challenges that come with being a CEO can be surprisingly lonely.

In this solo episode, John Wilson reflects on the last decade of leading Wilson Companies from a team of seven employees to more than 220. He shares the lessons that only come with experience, including imposter syndrome, difficult decisions, the weight of responsibility, and why leadership often feels different than people expect.

If you're leading a growing company or stepping into a leadership role, this episode offers an honest look at what it really takes to grow as a CEO.

In this episode:

•  Why you never really feel ready to be a CEO 
•  How leadership challenges change as your business grows 
•  The hidden cost of difficult decisions 
•  Why success often feels different than expected 
•  How to avoid becoming the bottleneck 
•  Why your business can only grow as fast as you do 

Watch this episode early on the John Wilson YouTube channel:
https://www.youtube.com/@JohnWilsonOAO

More Ways To Connect with O&O

• John's Podcast YouTube Channel
• Owned and Operated Newsletter 
• John's Long Form Channel 

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John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

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Transcript

SPEAKER_00 0:00

I'm completing my 10th year as the CEO of our business, and here is a list of things that nobody ever prepares you for. My whole career, I always assumed that people a few steps ahead of me knew so much more than me, and they had it all figured out and they knew the steps. And the more people I talk to, the more I realize that everyone has imposter syndrome, and we're all just figuring out the next step after our last one. We kind of have a plan, we're really comfortable in ambiguity, but no one's got like the know it all. We're all just figuring it out. So, number one, the things that people don't tell you is you don't really feel like a CEO at first. I started feeling like a real air quotes CEO when we were crossing the 20 million mark. And I started feeling that way because some of the decisions that I was making felt like the decisions that would need to move the business forward. But I didn't just like wake up feeling like this magical CEO one day. I still don't today. And many days I feel like I'm the wrong person for the job, despite the fact that I have tended to make the right decision for the business. And then when you look backwards at what you did, it was like, holy crap, okay, I don't give myself enough credit. Now I understand imposter syndrome. The second thing that no one tells you about being a CEO is the problems get less obvious and they don't get easier. You don't have enough information, and you should kind of make a decision on this pretty quick. And those decisions can have impacts anywhere from $10,000 to $10 million, depending on how we think about that issue. And are we approaching it with a framework or asking the right people? If it's an acquisition, a new market, we're actively hiring a CFO. All of these conversations were things that I spent hours and hours and hours ruminating and asking questions and talking to people who are CFOs, who who hired CFOs or who fired CFOs and trying to understand what are all the blind spots that I have for this kind of complicated problem. So that way I can make the most informed decision in a high-risk, very gray area. The best way to prepare yourself for problems getting grayer and more ambiguous is building a network of people around you that you can call when you just don't know the answer, which upcoming hint is almost every day. Section three: the thing that nobody tells you about being a CEO is that you carry the weight even when nobody sees it. If you run a small business, you know the pressure of everyone looking at you for the answer. You end up carrying the weight whether or not you want to. And it's hard to take vacations, it's hard to sleep for some people. A lot of people get into owning their own business because uh they think the money looks really cool from the outside and they think it sounds fun to be your own boss until you realize that you're not your own boss. And every person that uh works for you, you work for them, and you have the pressure of everything that you should have the pressure from, uh, from that responsibility. The fourth thing that nobody tells you about is you have to disappoint people. Leadership means that you have to pick the right choice, not necessarily the easy choice or the choice that makes the most people happy. Over my 10 years, we've gone through several rounds of layoffs, we've gone through branch shutdowns, we've gone through some really hard shit that was not popular and was not wanted or liked. And it was my job, it was my responsibility to deliver that news and come up with a strategy to mitigate the damage when it was causing damage. You're gonna disappoint people on this path, and your job is to do it respectfully and attempt to mitigate the damage as much as you are capable of doing. The fifth thing that no one ever tells you about is that the loneliness is real, but it's not always dramatic. It is challenging to go through the pressure and the decisions that you have to make that are unpopular or popular or whatever, and not feel alone. The way to mitigate that, which will not totally solve it, is a group of peers that you can talk to that are there with you. A lot of people have business partners for that reason, so they don't feel like they're going it alone, but it is a very real problem and it is a very real amount of pressure. So most business owners that I know, despite having friends and relationships and everything else in the world, always describe themselves as lonely. The sixth thing that nobody tells you about is that you become the bottleneck before you realize it. It's clear from the outside that the person holding the business back is the owner. It's so easy to become your own bottleneck, and it's so easy for every decision to come to you. It's so easy for that to happen because trusting people is really hard. And trusting people to make decisions the way that you would make them is really hard. And it takes grit and vigor and real risk-taking personality to go find someone that can make good decisions in your stead and hire them to come in and make good decisions for your stead. This is one of the most complicated parts of your business is hiring people that you trust to make quality decisions while you are not there. It's complicated, it's hard, and you can become the bottleneck before you realize it. The seventh thing that no one tells you about being CFO is success does not feel the way that you think it does. So it's hard to feel like you made it because every time that you clock a win, the goalpost naturally moves. It used to be my life's greatest obsession to hit $10 million of revenue. And I just couldn't imagine for those first seven years of my career being an eight-figure business. It drove me unlike almost anything's ever driven me in my life. The moment we hit it, I was like, okay, now what? Now I guess 20, 30, or 100. Like now what? And the goalpost moves because it's just the next step, despite it being a success. Section eight, you have to stay human while becoming better at the job. When you scale beyond 150 people, it gets more and more complicated to keep the human as a part of the organization. It's hard to connect in those fleeting moments that you have someone, and it gets harder for people to not feel like a number because of the lack of connection inside the organization. This is an area that I'm not especially strong at, and it's an area that I've been working on for some time. I don't think that I'm an expert at it. I think that I have a lot of people that I admire that do an incredible job at connecting their team and being like real leaders for the people inside the organization. And for me, this is an area of weakness that uh I'm continuing to work on. The company can only grow as fast as you personally grow. You can only carry what you can hold. And if you aren't training yourself to hold more and grow yourself personally and grow stronger and better at your craft, you will fail at some point in the process. You will stop growing. The business in any aspect is going to be capped by the leader, and that leader's ability to grow personally and mentally to be able to handle all of the challenges that we've talked about so far. The tenth thing that no one ever tells you about being a CEO is sometimes there is just no good decision. A book that I've read a lot is called The Hard Thing About Hard Things. And it describes this founder going through a really challenging moment in their business, and the only way through it was through it. There wasn't a magical path or a door open that would suddenly make any decision a good decision. And sometimes that's what that's like. There is no good decisions, only bad options. And you just have to pick the least of the worst. My final thought, closing this out, is that you can only lead as your authentic self. I tried to be someone that I wasn't because I read books that told me this is how you're supposed to lead your company, and that's just not who I am at my core. I do have to continue to improve, I do have to continue to get better, but I can only be who I am, and I can only bring my authentic self to me and my team every single day. And when I started leaning more and more into just like this is who I am, this is how I'm going to lead, and I'm just gonna be like a nerdy random dude. The business started compounding faster and the team started gelling better because I was just who I was. If you're on the path of being a CEO, I wish you luck. I wish you, I hope you share your comments below for anything that you've gone through or that resonates from the video that we shared today. And I would love it if you liked and subbed.