My Biggest Failure as a CEO




Failure is a requirement for learning and growth.

In all honesty, we should talk about failure more often, embrace failure (even if we’re competitive) and let our team members fail way more often.

In an attempt to embrace failure on my own, I’m going to share one of my most recent failures, what I’ve learned from it, and what I hope you can learn from it.

So here goes.

This failure of mine took place over a year period, as my company was transitioning from a lean startup to a successful small business.

My Most Recent Failure

In 2015, I co-founded and became the CEO of a software development startup. For the first year, I worked within the frightening reality (as anyone who has started a company knows) that we could go under at any given moment. We didn’t have cash, a pipeline, or a proven track record of success.

During this time, we were in lean, mean startup mode.

I was selling, managing client relationships, networking, strategizing growth, and helping with operations. I, along with my partner, had total control over our business, and because of our diligence (and honestly, some luck), we eventually found success.

Finally, we grew out of the tumultuous startup period and became a small, yet thriving business.

The only problem? Me. I still acted as if we were on the verge of collapse. Allan and I remained in control of multiple departments, even as they grew beyond our ability to properly manage them.

I had a reoccurring thought in the back of my mind: what if we go out of business? Admittedly this is an unhealthy thought, but it’s the not-so-glamorous truth.

I held onto this thought even as we became cashflow positive, experienced sustainable growth, and hired talented individuals.

For over a year, I performed my duties in a defensive, reactive, transactional way that ultimately did not benefit our business.

As a scaleup CEO, I was not playing to win. I was playing to lose.

Staying in this mindset was a failure on my part. Because I didn’t focus on growth, delegate to new team members, or stop obsessing over finances, it cost our company many opportunities.

What I Learned From This Failure

In retrospect, it’s easy to name what I should have done in this situation.

As the company started to grow, I should have spent more time on strategy, what markets to expand into, and how. I should have focused on developing our team members so we could pass on responsibility and scale our organization.

While pondering these “should haves,” I learned a few things, namely how to be more intentional about my work and how I contribute to our business.

What You Can Learn From This Failure

If you’re a startup founder or CEO, I hope you can read this story and avoid some of the pitfalls I fell into.

The truth of the matter is startup founders and scaleup CEOs do share a lot in common, but there are many important changes that need to happen while transitioning from one to the other.

Many of the work habits and defense mechanisms that serve you well in a startup do not serve you well in a scaleup business. Being able to transform your mindset and shed certain responsibilities can help you realize your full potential much quicker than staying stuck in your ways.

Final Thoughts

What my failure mostly comes down to was opportunity cost.

If I would have made time to focus on strategic things, where might the company be today? What kind of impact could new hires have made?

Perhaps we would be further along in achieving company goals. Perhaps not. But it does make me wonder.

I am a firm believer in it, it’s never “too late” and luckily, my company is heavily focused on these scaleup and small business initiatives now. But it was hard to shake it off and grow up.