5 Pros and Cons of Being CEO of Your Company

And yet, the role is a double-edged sword. If your company is a big public company, you can possibly be looking at $10, $20, $30M+ a year. Or very easily get fired. If it’s one of the handful of $1B unicorns coming out of Silicon Valley, then this time around it’s likely more money than you ever dreamed of. But for most CEOs, the truth is not in the extremes.
It’s in the middle.

So before you decide to be the CEO of the company you want to create, here are a few Pros and Cons to consider first:

1. Pro: You decide the strategy and what’s important. When you are CEO you are ultimately responsible for the strategy: What to build? How to get to market? Where to focus? You get to put your ideas into action and test if they work. Then, when they do succeed, the sense of satisfaction is unbeatable. If you are the technical founder, and command the respect of those people around you, you also won’t have to hear much disagreement. People are following you because they believe in your vision and your strategy.

Con: You’ll work harder than you have ever worked in your life. It’s true not all CEOs are working on overdrive but when you’re trying to get a
company off the ground, there are always more mission critical things you need to do that require more hours than there are in the actual day. Look forward to the necessary red-eye flight you need to take to close a deal. The time pressure will seem worse than your college finals did and prepare for this pace to go on for years. Keeping physically fit with exercise will become a requirement just to survive the exhausting workload.

2. Pro: It’s an ego trip. It’s hard to be CEO unless you have a serious ego. Not that you have to be a jerk, but exuding confidence will ensure that people can look to you to lead them. In that sense, then yes, it’s an ego trip. Which means that, if you are already seriously thinking of becoming the CEO of your startup, then you probably have that necessary ego to both embrace and enjoy it.

Con: You’ll be lonelier than you’ve ever been in your life. That cliche “the buck stops with you” is absolutely true when you are CEO. There is no one to turn to if you have to make a hard decision. Your board is there to give you advice, but they are not going to tell you what to do. Your team is there to provide counsel and debate with you but in the end, they’ll look to you to make the difficult decisions. And there’s no one you can talk to. It’s unfair to burden your friends and family with these work related stresses. It’s you and the wall (or in my case the dog) talking it out sometimes.

3. Pro: You get to hire your team. When you are CEO you get to hand pick your team. You choose the structure of the organization, and hand pick the key people you want to build the company with. You choose the skills, the personality, the experience–and they will seem to become as close to you as your family. Building teams is a wonderful experience–and the best trait of a successful company comes down to the talent.

Con: You’re the one who has to let people go. It’s hard to consistently hire great talent which means sometimes you’ll make mistakes. You’ll hire a VP of Sales who looks and sounds good, but can’t build out a team themselves (think of Yahoo’s spectacular failure recently hiring and then firing of Henrique de Castro). There may also be a time when you may really like an employee but who struggles to consistently perform. When you are the CEO there is no ducking the responsibility of firing the people who have to go, and striving to do it with respect and kindness is an art form.

4. Pro: Customers rely on you to solve their problems. Most great ideas come from trying to solve a problem for someone. In the enterprise world, you’re most likely solving a business problem for another company. You could be putting a critical process in the cloud, so it’s more cost effective, or automating a solution for a time consuming technology problem. It’s a rewarding feeling to know you helped customer’s solve problems and improve their overall business–and of course make money for both of you in the end.

Con: Customers can jerk you around. A former CEO of a software company with $1B in revenue once told me he quit, in the end, because of some of his customers. They’d hold deals until the last day of the quarter, and then force him to drive the price down to get the deal done. After 10 years of building his company and providing solutions for countless customers, he was overwhelmed with the lack of respect his customer’s gave to his business. As you’ll find, this is not always the case and there will be times you are providing value to your customer but professional patience and just ‘sucking it up’ will still be required.

5. Pro: You set the culture for your company. And this many especially appeal to you if you are sick of the Silicon Valley bro culture. Many people spend 8-10 hours a day at work. And all this time should be joyful. Why work for a company, if the culture is not enjoyable? So as CEO, one of the most important responsibilities you have is to set the right culture of the company with the actions you do every day and not just what you say. Great CEOs, like Reed Hastings of Netflix, make this the centerpiece of their leadership. They focus on the areas they believe create a successful company and a positive environment to work, which in turn assists in better recruitment, and increasing their impact with the community.

Con: It’s your company. Well, is that a pro, or a con? You’ll find it depends on the day. Some days you’re so proud of the solutions your team provides that you could burst. But this will not be every day, definitely not every day.

So, if you want to be the CEO of your company then brace yourself. It’s a wonderful experience, and can be a thrilling ride, but it’s a roller coaster with many ups and downs. Maybe write down why you want it before you start, so that on the dark days you can remind yourself why you are doing it. Me? It was about creating a great culture.