Several years ago, Anna Brockway made a small move that soon became a very big move. She and her family had just bought a new house, and Brockway had designer furniture that didn’t fit in the new space. Plus, she was looking to buy some good pieces that would work in the new setting. She found eBay too big and uncurated. Craigslist was scary and full of junk. 1stdibs was “snooty and intimidating.”

Brockway wished someone would start a ‘curated Craigslist with a style editor, a delivery van, and a cash register.’

Brockway, who was head of worldwide marketing at Levi Strauss at the time, dreamed aloud to her husband that she wished someone would start a “curated Craigslist with a style editor, a delivery van, and a cash register.” The response from her tech-entrepreneur husband? “Congratulations! You just started a company!”

Her fun and welcoming site, Chairish, has revolutionized how furniture is marketed and sold and has made it easier for ecologically minded design lovers to recycle and reuse great pieces. Since Chairish began, it has kept 734,148 (and counting) gently loved items in circulation—85 percent of inventory is vintage. Chairish was named Newsweek’s “Best Online Shop” of 2021 and won the USA Today Reader’s Choice Award for “Best Place to Shop Online for Furniture and Home Decor.”

Here’s how Brockway made the big leap and keeps on innovating.

What in your background prepared you for your role at a furniture and design website?

I love fashion. It’s full of crazy design lovers to whom I very much relate, but I’ve always been a compulsive redecorator, constantly transforming and reimagining my home (and few friend’s places too!). Truly, I’m a home design addict. I love my job, because it 100 percent brings my personal passion and my profession together.

Everything I do is a work in progress. I take nothing for granted. Ever.

Were you worried about making the leap into digital sales, going up against some big guns like eBay? What words of wisdom got you through the startup phase?

The scariest part for me was getting over my “don’t show anyone the site ‘till it’s perfect” mindset, ingrained from years in the fashion world’s high production value culture. My mantra shifted to, “Let’s try it!” Why spend precious time and money perfecting an idea or business model that’s likely to morph a lot as you get market feedback? I took to heart Reed Hoffman’s famous quote, “If you aren’t embarrassed by the first version of your product, you launched too late.” I took a deep breath, hit “send,” and let the site out there. Scary.

What were the biggest obstacles you faced in getting Chairish started?

Chairish doesn’t just offer products for sale; it also provides ideas on how to put a room together.

Marketplaces are hard to develop because job one is to attract sellers to fill your shop with tasty inventory. But great sellers want to sell on sites that have lots of buyers. And buyers want to be where there’s lots of lovely inventory. So, it’s a bit of a Catch 22. Which comes first? The seller or the buyer? As a founder, you are standing in the middle of that seesaw with sellers on one side and buyers on the other. You are always balancing between the two. It’s dizzying.

When did you know Chairish was going to be a success?

Everything I do is a work in progress. I take nothing for granted. Ever.

What are the toughest projects you’re working on now?

Visualization is the big gorilla. Chairish was first in our industry to leverage augmented reality technology, enabling a shopper to see what an item will look like in a space before before buying it. AR has been a huge needle mover because this “try before you buy” capability begins to take the scary guesswork out of making important furniture decisions. AR technology is advancing quickly, and we’re just getting started.

Where do you see Chairish going? Adding more than furniture?

For sale on Chairish: an abstract painting by Louisa Chase, one of Anna Brockway’s favorites

Contemporary art has been a major initiative for us. We have loads of really fantastic, practicing artists listing with us. Even better, we now are partnering with our best-selling artists to offer prints of their work because we simply couldn’t keep their originals in stock. The most rewarding part of Chairish for me is when talented people get to quit their day jobs and make their passion into a career. It happens a lot. It happened to me!

How would you characterize your own design style?

Surprisingly, my own home is pretty spare. I buy and sell a lot so my space changes all the time, but I like to have a few things that are really interesting and stand out against a lot of negative space. Like a lot of creative people in visual industries, home is respite for me from the visual cacophony of my job.

Like a lot of creative people in visual industries, home is respite for me from the visual cacophony of my job.

Do you ever buy things before they go on the site for sale? If so, what’s one of the favorite pieces you’ve gotten off Chairish?

Every day we publish more than 2,000 newly added items to Chairish, so believe me, the temptation is real! My favorite piece right now is a humongous pale pink Louisa Chase abstract painting, now happily presiding over my oval dining room.

What’s your favorite room in your house and why?

I love my kitchen/family room, because it’s our family headquarters. The space is full of kids, laughter, and clear sunlight, thanks to views out to the San Francisco Bay. It overlooks our garden, which is exploding in pink and white blossoms right now. Nothing is better than sinking into one of twin sofas (purchased on Chairish of course!) that we re-covered in a soft, cloudy blue mohair. It’s like cuddling up on teddy bear. Total heaven.

A version of this story was originally published in April 2018.