Jeffrey Raider | Crain's

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

Jeffrey Raider


Harry's sells razors and grooming supplies online directly to customers. Before starting Harry's, Raider helped found Warby Parker, a company known for its selection of stylish and affordable eyewear.

The Mistake:

At the beginning of Warby Parker, we launched the brand and were completely overwhelmed with demand. There were four of us founders, and one of our classmates' wives worked with us to answer phones for 10 hours a week while we were in class. We had more customer experience calls than we imagined. Instead of trying to get help, I took it on myself to answer every call. I was still in business school and found myself on spring break in Colombia working 20 hours a day entering orders and trying to answer customer emails. Then I hit a breaking point, so we stopped and wrote our first Warby Parker job listing for Craigslist and found our first customer service rep, which completely changed my life in the company.

I think about that a lot at Harry’s, too. When we started Harry’s, we began it with Andy and I in a small office, just the two of us, trying to build the company ourselves. And at some point, again, we got overwhelmed, and I had to learn the lesson once more. We just stopped for three months and hired a team of eight new people to help us get to launch. There’s no way we could’ve done that if we hadn’t figured out how to delegate.

At the time when you feel the most strained ... that is the time when you should get help.

The Lesson:

I can’t do it all myself. At the time when you feel the most strained, like you have to do the most by yourself, that is the time when you should get help. For me, it’s almost a feeling of personal pain and stress, and things start to slip through the cracks. We missed opportunities because we weren't able to focus on them. Those are the times where we needed to pause, figure out how we’re going to be successful, and find help.

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