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3 Entrepreneurs on Their First Big Mistake Essay

Entrepreneurs look back on the blooper they thought would kill their company.

Sandy Chilewich

Founder and creative director,

“Back in 2000, when I was just starting, I emailed a buyer at Bloomingdale’s, pitching my place mats. And I don’t know if placemats just wasn’t in my computer’s dictionary, but each time I typed that, it changed to placentas. I didn’t notice and sent it. So I wrote this buyer a lengthy about how great my placentas were, and how many colors my placentas came in, and how durable my placentas are. I sounded like a madwoman. I never heard back from that buyer, but Bloomingdale’s is now one of our biggest customers.”


Jason Horvath

Cofounder,

“After 10 years of growing slowly and deliberately, in 2013 we got a $500,000 investment in and did some marketing, and the following year we sold $10 million. Then we lost . We decided to launch an interior design department as well as a jewelry line — a total vanity project — and hired more than 50 additional employees. Sure, we had sold $10 million, but then we spent $10 million, and we entered the next year with very little cash. Growth flatlined — we lost $1.5 million in six months. We had to pull back, lay off some great employees and shut down projects. But now we know what we’re good at and how to manage growth.”


Nathan Bond

Cofounder and CEO,

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“My wife, Anna, and I launched our stationery company in 2009, just in time for the holidays. We had no background in this space and had never worked with a printer. We thought we could send them a file and the product would arrive in perfect shape. But what came back was totally unusable. Even after multiple production attempts, our cards came back with ink smears all over them. We had to make it work, though, so we erased the errors by hand for hours — sitting in a room, in a cloud of eraser shavings! We learned a lot, including how naïve we were.”

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