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What It’s Like To Be A CEO

“What is it like being a CEO?” I’ve heard so many people ask this very question. 

“Is it a hard job?” “Is it lonely?”

The simple answer is yes. It’s really hard and lonely at times. 

I’ve been a first-time tech CEO since January 2018 and can explain what my personal experience has been like so far. 

Everyone’s experience is different and unique to them—but this is my story. 

When I embarked on this journey, I naturally thought it would be a lot easier than it’s been (as we all do). I had run a company before and I knew about recruiting, but oh I was so wrong. I realized what got me here, might not get me there. Yes, the experiences I’ve had will help, but every company, every industry, and every team is different. 

Let’s just say in the last two years, I’ve learned more about myself than in my whole life. You’re probably wondering, why? 

Running a company with so many new things that I simply overlooked as “easy” was actually difficult and overwhelming. I’ve learned so much about myself by admitting what I don’t know and it’s given me the space and the opportunity to overcome my weaknesses and be a better person. What I saw and experienced as a salesperson (recruiter) operating in the finance industry was very different from running and operating a tech firm with different functions. It’s ultimately a much more complex business with tens of millions of dollars invested by some of the largest VCs in the world. 

I’ve written about hiring, culture, the mission, and more, but at the end of the day, I’m accountable to the company. The better I show up, the clearer the vision I have, the simpler the strategy, the more successful the company will be. 

I’ve gone through so much over the years, but what I realized through those experiences is that I’ve suffered from depression and loneliness as a CEO. I found it very hard to deal with, and no matter what I thought I was doing, it wasn’t working. I knew I had to get help, as I was committed to being the best CEO I could possibly be. Making sure that we could accomplish our mission of making the world more equitable is truly all I really care about. 

With the help of Thuy Sindell, my executive coach, I learned as much as I could about myself. I did a deep dive into my enneagram to understand how and why I show up differently (being an 8 has its challenges for sure). In addition to that, I’ve worked on my own happiness and general well-being. This was clearly something I had never prioritized before. But what I’ve learned is that if you don’t take care of yourself you’ll never be able to take care of anyone else. There’s a reason why flight attendants tell you to put your oxygen mask on first in an emergency situation. 

Why is it hard? 

At the end of the day, the buck stops with me. As CEO, you have to think about everything in the business. If you fail, everyone fails. To be clear, I’ve failed so many times. It wasn’t until I was at rock bottom and questioning if I could do the job that things started to change. It’s been a real journey that I’m still on today. 

I’m sure you’ve heard before, being a CEO is a lonely job. It can be at times, but what I believe is most important, is the team you surround yourself with. The key is finding people who have the same level of ownership, dedication, and authenticity as you. But let’s be honest, that is easier said than done. It takes a lot of time and it’s hard to find. 

As difficult as it is, you have to really focus on the things that matter. With the right people, you can do anything but you have to set them up for success. I found myself being more distracting than productive, by being very reactive rather than taking the time to digest, plan, and prioritize.

So what I’ve realized is being a CEO isn’t rocket science. It’s about focusing on the things that matter most. I’m really grateful for the team that I’ve got today. Without them, I wouldn’t have the space and time to focus on myself and concentrate on the more strategic things for the business. 

The 5 keys to success

  1. Have a consistent & clear mission, vision, and strategy 

  2. Prioritization is really important, only have a few metrics that matter at the company level  

  3. Make sure you have leaders & mentors you can trust and rely on who are strong in areas you’re weak

  4. Delegate and empower your team, playing more of the coach role

  5. Focus on being an incredible communicator, this means learning how to simplify things and reinforce them

TL;DR: Before you take on this massive responsibility of leading a company as CEO, take the time to reflect on what it would mean to be one and what it will require from you. As exciting as it may seem from the outside, it's still a job, one that can get lonely at times, and would require you to adapt and change as your business grows.

Thank you to all our ex-employees, current employees, board members, investors, mentors, advisors, coaches, and our customers. I've learned things from all of you and I’m very grateful for your commitment to this journey. 

— Ben Herman, CEO

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