Gabriel Weinberg | Crain's

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

Gabriel Weinberg


DuckDuckGo is an online search engine that does not collect or share users' personal information.

The Mistake:

My first startup was an educational software product, which would eventually be sold to schools. I hired the wrong people; I mean, I hired all of my friends out of college. Typical bad mistake. I should say that some friends are fine to hire, but just because they’re your friend doesn’t make them a good hire.

We never got to more than six people, so all five people I hired were friends, and every single hire was wrong. They were all wrong for different reasons, but one that I particularly remember is a super nice guy who would definitely make a good employee in general. He moved up right out of Duke as an economics major, and I trusted him to be our finance person. Side note: a startup doesn’t need a finance person. So that’s a wrong hire right out of the gate.

But startups were also just not his career path; he ended up being an administrator and he’s now the dean of students at a private high school. I moved him to Boston, completely out of his environment, and I don’t think it ever clicked. Shortly after, the company went under. And I feel really bad about that. He then joined Teach for America for a year and moved back to Atlanta, but when [the company] died, he was in Boston with nothing really to do.

We hire from our community of users, who share our mission.

The Lesson:

I started DuckDuckGo kind of by myself for the first few years, and when we started getting real traction, I realized my mistake from before and decided that I needed to get other people involved. So I went out to raise a Series A round of financing, and through a lot of luck, was able to partner up with a really great investment firm: Union Square Ventures out of New York.

That really changed things. Just being part of the right community, and having access to people, and more readily taking advice and things like that. I set up a CEO peer mentoring group where I live that’s quite valuable, and I’ve encouraged our employees to do the same.

Our hiring process is now the opposite of my initial hiring process. We are a mission-driven company and we hire from our community of users, who share our mission. We contact them first to see if they’re a good fit, and as a result, they can come from anywhere in the world. We have a team of people who are really dedicated to what we’re working on — they weren’t just opportunistically looking for a job in the location we happen to be in. So that has turned out really well and I would definitely do it again.

Follow Gabriel Weinberg on Twitter at @yegg.