Paul D’Arcy | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Paul D’Arcy


Austin-based Indeed allows job seekers to search millions of jobs on the web or mobile in over 60 countries and 28 languages. More than 200 million people each month search for jobs, post resumes, and research companies on Indeed. D’Arcy has also worked for Dell and Apple and holds an MBA from Harvard University.

The Mistake:

Becoming a CEO before being ready to lead.

I was very lucky in my early career to have the opportunity to start a company when I was 28. I quit a great job at Trilogy and created an Internet company that created services for professional photographers.

I had previously worked as a photojournalist and loved photography. I saw this as an amazing chance to do something that was personally important. Everything started well with the company: I raised venture capital from a great firm and found some strong people to help me with product development and get the business running.

But with big endeavors comes the opportunity to make big mistakes, and I made some really big mistakes as a first-time CEO. I really didn’t understand fully my job.

My vision for the company wasn’t clear. I didn’t create clear purpose in the work the team performed. The goals and milestones that were critical for the company were only in my head. And because I didn’t communicate them clearly to the team, we didn’t hit them.

The other thing is I didn’t lean enough on the amazing community around me in Austin. There were so many people who would have supported me with ideas, assistance and mentorship. As such, in the end, the business wasn’t successful.

The quickest way to learn and get help is by asking questions.

The Lesson:

I learned three important lessons from these first experiences as a CEO.

First, I learned about the importance of leadership. I learned how essential it is to build the right team, to create a business with a purpose that matters to people, and to set goals that provide a path to success for the team and the company. I learned how important it is for everyone on the team to know what success looks like for them individually and for the company as a whole.

Second, I learned the importance of asking lots of questions. In that first company, I made too many decisions by myself with too little help. The quickest way to learn and get help is by asking questions. I believe that if I’d asked the right questions of potential customers, employees and investors – then things may well have turned out very differently. 

The third lesson I learned is that it’s better to fail small than to fail big. Because I had taken a venture capital investment, the stakes were really high. Everything we did was a bet on the company. If we didn’t hit our goals, we would have to shut down. It was a really big bet – and it turned out to be one of my bigger failures in my career.

Today I focus with my team on testing as many things as possible on a small scale and scaling the things that we can prove will be successful. Together with my team we fail every day with these tests but each of these failures teaches us important lessons. And when we do find something that works, we invest in it and go big.


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Pictured is Paul D’Arcy | Photo courtesy of Indeed.

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