Monica Enand | Crain's Portland

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

Monica Enand


Software firm Zapproved offers a cloud-based service that helps corporate legal teams streamline the e-discovery process and better manage data.

The Mistake:

About 10 years ago I decided I was interested in starting my own company, and I thought I needed to know everything about startups. I’d begun my career at Intel and then worked for IBM, so I’d worked mostly in big companies. I had managed large engineering projects, and I knew how to build products. But I didn’t know anything about how to raise money, how to make the right case to investors, how small companies sell to big companies when they don’t have a brand name or an established relationship. I didn’t know how to hire and build a team from scratch.

I really became focused on being perfect. So instead of just diving in, I worked for another startup where the founding team had been in place for a few years. They were just getting their product launched. I worked as part of the team, and through that exercise I realized: It wasn’t that I needed to be perfect, or that I needed to know everything. Because none of those people were perfect. None of them knew everything. But they were willing to be brave. They were willing to take risks. They were willing to say they didn’t know, and they were willing to listen and get help.

I worked for that company for two full years, watching the executive team make mistakes and learn along the way. And I realized I didn’t know why I thought I could not do it. I always thought they knew everything beforehand. But they didn’t.

No one knows everything the first time.

The Lesson:

When I realized that the people who are out there and learning at the fastest rate are not perfect, they are just brave, my trajectory of learning and exposure really accelerated. I became able to take in information and figure things out faster than I had before.

No one knows everything the first time. You have to figure it out. You can’t wait until you know everything. If you wait, it takes too long, and you don’t learn fast enough. Once you decide, OK, whatever I don’t know, I’m going to have to learn along the way, everything accelerates. You suddenly can get things done at a pace and a scale that you never could imagine before.

You have to constantly monitor yourself. Once you dive off the deep end and say you’re going to do something, unless you are willing to accept failure, you have to find people who are willing to teach you. You use all of your resources to get there as fast as you can. You’re constantly reminding yourself that you can learn these things in the beginning. Then it just becomes second nature. You start to believe that you have this superpower of learning anything you need to learn.

Once you believe that, then you’re golden. People who have crazy trajectories in their career, they just get to the point that they believe in themselves. They can learn anything. And because they believe that, they can do it. 

Follow Zapproved on Twitter. 

Pictured: Monica Enand | Photo courtesy of Zapproved.

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