Dream Jobs: Anna Brockway of Chairish

Dream Jobs: Anna Brockway of Chairish

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Jennifer Hunter
Dec 9, 2014
(Image credit: Charish)

Welcome to Dream Jobs, a new series where we ask some of the coolest, smartest and most creative people working in design today to tell us all about their jobs and just what they did to get there.

Anna Brockway is the Founder and Chief Curator of Chairish, a genius site that makes buying and selling gently-used furniture and decor a snap! She's also got four kids so we're kinda surprised she had the time to answer our questions at all! Lucky for us (and you), she found the time to tell us how she got to where she is today.

When did you know what you wanted to do?

I have always been downright obsessed with home design, but I conceived of Chairish out of personal need. Our family had four kids in 2.5 years, resulting in a chain of house moves (bad!) and as well as re-decorating opportunities (good! or so I thought). My husband and I were getting into spats over both the initial expenditures on furniture and then again at the item’s lack of resale value when it didn’t work in our new space. We had amazing, barely used pieces to sell and no easy way to show them to buyers who would appreciate them. I dreamed aloud, "I wish someone would start a website that makes it easy for design lovers to buy and sell great stuff to one another - like a curated Craigslist with a style editor, a delivery van and a cash register!" And he said, "Congratulations! You just started a company!" That was said in our kitchen less than 2 years ago, and now we're a team of 25 people.

Where did you go to school? What did you study?

I went to Columbia in New York City where I majored in Art History with a focus on Architectural History. I studied with Barry Bergdoll (now the Chief Curator ofArchitecture and Design at the MoMA) along with some other truly impressive thinkers who taught me about architectural history but more importantly, about trusting in my own independent thinking. It was a transformational and emboldening experience for an insecure 17-year-old creative kid from a dinky town where swim meets were everything.

How did you score your current job?

I founded the company, along with three colleagues with deep experience in technology and the home décor industry (my husband is one of them!). Prior to that, I was the head of Worldwide Marketing for Levi Strauss & Co. and most recently a stay at home mom of 4 rascally kids.

What does a typical day look like for you?

5-6:30 a.m is my solo “coffee and curation” time when I review every item submitted to Chairish and determine which pieces we will accept.

6:30-8 a.m is all about the kids - breakfast, backpacks and buses.

8 a.m to 5:30 p.m is spent hashing out messaging and media programs, working closely with our product team to identify site improvements and directing our curatorial teams regarding needed inventory. All of this is underpinned with a deep study of our business analytics. I also try to meet with at least 3 new contacts from both inside and outside the home décor and tech industries every week, so I can learn what I don’t know. And twice a month I leave San Francisco to see what is happening in the real world!

5:30 to 6:15 p.m - I walk home and don’t talk to a single soul.

6:15 to 8:00 p.m is dinner and more family time followed by 1-2 hours of work after the kids’ bedtime.

What’s the coolest thing about your job?

Looking at really beautiful vintage furniture, art, décor, jewelry and accessories all day long. Also, I must say, I love spending time with the folks who sell and buy with us. They are total design maniacs who can spend hours discussing topics like variations in Gustavian finishes and Adrian Pearsall’s use of plywood so I feel amongst kindred spirits.

What’s the worst part of your job?

Expense reports. I mean how is it 2014 and we are still spending time totaling cab receipts? Jeesh.


What advice would you give to someone looking to do what you do?

The best advice I could give is the best advice I received: "If you are not embarrassed by the first version of your product, you've launched too late." - Reid Hoffman

Our first really big decision was deciding when we were ready to open. My experience from the fashion world was to hold off until the site was airbrushed perfect. My co-founders were dead set against waiting. They felt we needed to get the first version of our site up to get some user feedback. This would allow us to answer the first and most important question: Does anyone need or care about this service? I took a deep breath, trusted their advice and we launched with terrible looking visuals and limited inventory. I felt like I did when I got a wedge haircut in 4th grade - totally mortified. But in our first week, people started to buy from us and in week two, we scored our first single sale for $10,000. Quickly we saw that there was a market. Had we waited to launch, we would have wasted resources perfecting something that was only bound to change. Moral of the story: Don't let perfect be the enemy of trying. Or as my handyman Merle says, "Just put some paint on the wall and see what it looks like."

What else should we know about what you do?

From the start, I wanted Chairish to be a cool, full-service, online swap meet for design aficionados. I have an open-minded attitude and am totally turned off by pretension, which is an unfortunate characteristic of some segment of the design world, so it was essential to me that my company feel fun and NOT intimidating.


Check out more at Chairish.

Thank you, Anna!

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