Heather Jassy | Crain's

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

Heather Jassy


Etsy is an e-commerce platform selling handmade crafts, vintage finds and other items from a community of creative entrepreneurs.

The Mistake:

I have been an entrepreneur for most of my adult life, and the first business that I owned was a struggling independent bookstore. The owners were ready to retire from the bookselling business and they wanted to pass it on to someone young and energetic to keep it open for the community. One of my college professors was friends with them and introduced me to them.

As they talked about it, I just got so excited. They had been doing poetry readings and art exhibits and it was not just a bookstore but a community space. I had worked at a bookstore during college, so to me, owning my own bookstore was my dream. I loved the idea of being able to talk to people about books all day. I had also shopped at this bookstore when I was in college, so the idea that I could own it and keep it open for the community was really exciting for me. It had a lot of things that I really loved, so when the offer was there, I immediately said, “Yes!” without fully knowing what I was getting into.

I was 23 years old and had never managed anyone, and suddenly, I owned a bookstore and had employees. I walked in on the first day and I didn't even know how to turn on the lights. I didn't know that much about business. I've never run a business before, and rather than reaching out to people who could have given me advice, like my grandfather, who is a creditable businessman, I was very headstrong. I wanted to prove to everyone that I could do it all by myself, so it was difficult for me to ask people for help.

I spent the next four years working incredibly hard to grow the business. I burned myself out and ultimately closed the business. I realized things weren't getting easier; they were getting harder, and I hadn't taken a vacation in two years. That's when it became real to me that it was not sustainable. It would have been a very different trajectory if I had been willing to ask for help from people who knew more than me, and ultimately, I think that I made my life a lot more difficult by not doing it that way.

I was 23 years old and had never managed anyone, and suddenly I owned a bookstore...

The Lesson:

In my day-to-day work at Etsy, I always spend a lot of time thinking about how we can support our 1.6 million sellers. I think about how I felt in that situation of being a solo entrepreneur and what I would have needed or what services would have made my life easier. And that's something that constantly informs the work that I do and how I think about what we do for our sellers and how we build community at Etsy.

One of the things that's so incredible about Etsy is that we have this really robust community of entrepreneurs that support one another — so they can be that support that I feel I didn't have as an entrepreneur. Anytime we have a new feature we have our sellers test it for a long period of time and react to their feedback before we launch something. We actually have a program at Etsy where we bring sellers into the office for lunches to meet with employees, and we also have a program called, "Community Connections," where the job of that team is to make sure that everyone at Etsy interacts with sellers. We go on studio tours, so that people who build our products interact with sellers in their studios and watch how they use Etsy, watch how they use the tools and learn from them.

On a personal level, it's also really important for me to have very regular contact with real sellers. I often pick up the phone to call people who are going through something difficult and get feedback from them. I talk to sellers on Twitter. I also do a feature on Etsy called, "Fireside Chat," where sellers submit questions on social media and I do videos that are released on YouTube where I interview different people at Etsy and ask them the questions from sellers.

We also have a program at Etsy called, "Teams," which is pretty incredible. We have 11,000 teams on the Etsy platform. Some of the teams have 1,000 people on them. They are just amazing. They are all over the world, and these teams are just total powerhouses. They support and mentor one another locally, but they also do things like craft fairs and pop-up shops to help market one another's businesses. If I had that when I was an entrepreneur, that would have been so incredible. 

Follow Heather Jassy on Twitter at @hjassy.

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