Stress and Leadership – My Experience as a Startup CEO and Some Steps to Cope

I got involved with my first start-up in my mid-20s. I was hired as the first “business” hire, where most others were on the engineering side except for me and the CEO. I was hungry for the challenge to prove myself and dove headfirst into the start-up life.

Resources were thin at this early stage, so I worked my ass off booking all the meetings at our first trade show, writing website copy, confirming meetings with potential clients, and preparing sales handouts. Ultimately we had a great show, which led to deals with studios and TV networks. We achieved enough early milestones to raise capital and hired more people to help execute on ever-larger goals. Fast forward four years, we sold the company for over $100 million, and I became addicted to the journey of start-up highs and lows. But that early time still stands apart as a self-inflicted high-stress environment that many start-up employees and founders go through.

Next, I started my own company as a first-time founder/CEO. The pressure was higher, but I was young with no family pressures and a lean personal burn rate. I could share the burdens with a co-founder in the early days. As the company grew, I felt the brunt of that pressure as the Founder/CEO. Sometimes it was so bad that after dealing with a stressful situation, customer issue, or even an investor, I would go to a bar and ask for a tall glass of vodka on the rocks and chug it to take the edge off. Not a healthy coping strategy, but it got me through a couple of challenging moments. There have been other times where the pressure drove me into periods where I didn’t sleep, and it felt like the world was crashing down around me with no way out.

From my own experience and hearing similar stories from friends, I know that many people are going through this struggle right now and don’t recognize that it’s not okay. Mental health stigma has thankfully come into focus in recent times, but it is still a huge problem. Back then, it was not something you talked about. The stress and constant anxiety that kept you up in the start-up world was part of the ethos. Start-up “grind” and “grit” are what VCs wanted, and many still do. The profile is a young, hungry tech graduate willing to code all night. It wasn’t a job. The company was your life.

Making it worse, as a founder or start-up employee, you are constantly seeing articles and news updates of the big raises and newest acquisitions. You are always reading about company highlights and the most recent overnight success story. These stories don’t cover the grit and hard times in between, the challenges you overcome, or how you put your shoulder into it to get through a huge challenge and still manage to keep going. This struggle is where you live for the first few years of your company, and that anxiety will always be present.

During this time, company leaders struggle to cope. The constant pressure of when will we raise the next round? What happens if we hit the “wall” and run out of money without a backup plan? Will the employees who bet on us be left without jobs, and their families be in financial trouble? What about the early investors who put their money in to support the idea? The anxiety can take your energy away and send you into thought spirals that can easily throw anyone into a state of high anxiety or even depression.

When all the world feels like it’s coming down on you and you struggle to deal with the stress and anxiety of starting something new, I would recommend a few ideas from my experience that could help you cope better: