6 CEOs Reveal What It Really Feels Like to be The CEO of a Startup

6 CEOs Reveal What It Really Feels Like to be The CEO of a Startup


How does one become a chief executive officer (CEO) of a startup and do a good at it? Technically, most startup founders end up filing the chief executive slot, but typically people who have distinguished themselves in some manner and have strong leadership characteristics end up getting the job.

Being the CEO of a startup is one of the most challenging roles out there. Your job is to build a product customers love; recruit a team; find funding from customers, partners, or investors; and lead your team to build a great company that can stand the test of time. These are the experiences of some CEO’s.

1. Jason M. Lemkin, Co-founder/CEO EchoSign

People will actually care what you think in a way you’ve never experienced before.  Even if you are just a CEO of a 10 person company, your customers will care, even if they are 10,000x bigger than you are.  Your team will care.  The CEO matters to whomever the product impacts.

You will think about stepping down at some point, no matter if you never admit it.  There’s a reason Elon Musk didn’t start off as CEO of Tesla, nor did Marc Benioff start off as CEO of Salesforce, even though they wrote the first checks.  Dude, it’s hard.  Don’t tell anyone when you have these thoughts.  Except maybe your one closest advisor.

2. Paul DeJoe, Founder & CEO at Ecquire

Very tough to sleep most nights of the week. Weekends don’t mean anything to you anymore. Closing a round of financing is not a relief. It means more people are depending on you to turn their investment into twenty times what they gave you.

It’s very difficult to “turn it off.” But at the same time, television, movies, and vacations become so boring to you when your company’s future might be sitting in your inbox or in the results of a new A/B test you decide to run.

You feel guilty when you’re doing something you like doing outside of the company. Only through years of wrestling with this internal fight do you recognize how the word “balance” is an art that is just as important as any other skill set you could ever hope to have.

3. Josh Abramson, Previously Co-founder/CEO Connected Ventures (CollegeHumor.com, BustedTees.com, Vimeo.com), Currently CEO BustedTees.com

I think the most interesting thing about running a start-up you’re passionate about is that it doesn’t feel like work.  My co-founders and I lived and worked together in the same apartment for nearly 6 years, so we were basically working 24/7 as we’d constantly be talking biz even if we were out at a party.

I didn’t take a proper vacation for a few years, and when I finally did I made a point not to bring my laptop so I could unwind a bit… then I quickly realized that this was actually much more stressful for me than spending a normal day in the office.

4. Lee Johnson, Founder. CEO of FlightOffice

I miss the process of coding, of solving engineering problems and the lack of responsibility. but, in exchange I get to control my destiny and drive my vision. I get to create something grand and see it through all stages of the process, ultimately being in control of what road we are going to travel on. I wouldn’t trade that for anything.

I never imagined how much being a CEO of a startup would utterly transform me as a person. I’m the founder of my company (and held the title of CEO), but for the first 2 to 3 years that’s all I was. In the past year I grew into a CEO and that was one of the most difficult yet most rewarding transitions I have experienced in my life.

The life of a CEO should be about communicating and connecting with people as part of the process of successfully executing on a vision.

5. Deena Varshavskaya, Founder and CEO of Wanelo.com

It’s incredibly fun. You’re passionate about a problem and an opportunity and you don’t need any reasons to pursue it other than intrinsic enjoyment of building something you love. You’re usually up to some great challenge, but, guess what? – you’ve chosen to have these challenges because if you didn’t have them, you’d be bored to death on a daily basis.

Your startup is your territory for endless personal growth. You get to push your comfort zone literally every day and that is an incredible opportunity. The challenges you overcome, the things you learn about yourself, the value you create, the people you get to know give you a sense of freedom, play and empowerment.

6. Darren Wang, Founder, CEO of owlting.com, obook.com

Since day 1, you will start feel pressure since you bet all your money in the company’s account.  The best way to describe my status is my sleep, before I started the company, I always have 85-95% satisfactory sleeping.  After the company registered and start burning money, the satisfactory index drops to 40%-50%.  You always think about anything related to jobs even in the dream.

This topic originally appeared on Quora.