Chairish’s Anna Brockway discusses trends, ‘the return to pretty’ and how to launch an online business

Anna Brockway is the co-founder of Chairish, the online marketplace for vintage and antique furniture. Chairish is a venture-backed company that has raised $60 million since its inception nine years ago. The company grew 80% in the first half of 2021, 40% in the second half, and is continuing to accelerate in 2022. Brockway spoke with Home Accents Today about how the business has evolved, what’s next for the brand, and what on her trend radar.

Tell me about the early days of Chairish. How has the business evolved?

I come from the fashion industry. I worked in advertising and later at Levi’s, for a very long time. My husband is a tech guy, he was co-founder of Hotwire and TripIt. We had these two crazy professional careers happening and had a lot of kids in our lives really fast (four kids in two and a half years) and ended up moving three times in two years. Moving is a pain, but for me it was fun because it was like a new decorating assignment. But as I went from thinking about the process of decorating to actually decorating, I saw a huge disconnect. Anything I saw in stores or online was really flat and boring and kind of unfriendly. I ended up shopping vintage. I found I could get one-of-a-kind pieces with incredible style and enormous value. The cherry on top was the sustainability component. It became increasingly clear that there was no place that had a beautifully curated collection of the best things at reasonable prices open to people like me, a non-designer.  I was no longer working at Levi’s, Gregg had sold TripIt. He was drumming his fingers on the table, wondering what to do. I said, “You should start an online vintage marketplace,” and he said, “No, you should.” So we started Chairish at our dining room nine years ago. It’s been a really fun experience building it.

What did you learn about working with your spouse during the process?

My husband and I are both respectful of each other’s professional and intellectual capabilities. I think that is why we are a good match and fell in love in the first place. But before working together, I called my friend Kevin Hartz. He and his then girlfriend and now wife, Julia Hartz, started Eventbrite together. They worked together so beautifully. I consulted with them to learn their tricks to working together. They stressed the importance of working shoulder to shoulder and in parallel, but not to overlap in areas of accountability and responsibility. I think that was the best advice anyone could give me.

Gregg and I have totally different but complementary backgrounds. At Chairish, I focus on the supply and the demand — all the inventory and all the shoppers and how the brand is presented. Gregg is responsible for engineering and product development, all the logistics, customer service and shipping, and all the analytics. So we definitely work together but we don’t work on top of each other. We stay in our own swim lanes, so to speak.

What lessons from your previous marketing role at Levi’s have helped you in this job?

It was a fantastic experience, and I had the opportunity to try a lot of different things. It sparked my love affair with all things vintage. One of the strengths of the Levi’s brand is the way customers love them, and how valuable it is to people to feel a sense of uniqueness and individuality in how they present themselves. Every generation, every youth moment, every fashion moment, has taken this basic product and reinvented it to make it their own and create their own personal take on it. What I took away from that is how important it is to create a brand with such great wingspan that it leaves space for buyers and shoppers to take the product and use it to tell their individual story. That’s how we think about Chairish. We bring this massive assortment of really beautiful things that range from simple wicker pieces to casegoods and Art Deco and antique pieces. I think this is extremely uncommon at most retail. We endeavor to have this really diverse library and to open that up as a pantry of ingredients, if you will, to let designers to rumble around for what they’re looking for, using us as part of their creative process.

How has the recent acquisition of Pamono changed the way you do business?

We purchased Pamono in August 2021 and brought all its inventory onto Chairish. The combined entity makes us the largest pure-play vintage site, I think, in the world. We believe strongly that our customers and their customers comprise a design-loving community that is essentially global. Many of things on our site originated in Europe. We’ve brought it all in one place so design lovers have everything in one easy to shop location. Europe has exceptional product. To be able to bring that to our customers is especially fantastic.

Your company is primarily female-led, which is rare in technology. Tell me about your recruiting and team development strategy.

The company is 70% women, and our executive team is 82% women. It’s rare in technology. Only 2% of venture funding goes to women-backed companies, to give you an idea of how unprogressive it is in the tech world. The fact is, we work in a category where 80% of our buyers are women. Women tend to be the purchasers and decision makers. It helps to have a woman co-founder. That’s an important part of the story as well.

That said, there is a ton we’ve done. Our company has just under 200 people, and we’ve made a great effort to make it extremely family friendly. When we plan our corporate events, we think about school schedules. We think about how to set up our benefits package to support parents. We have been very supportive of working from home. I think that is something we have in our DNA because we are a husband-and-wife team with a family.

The other thing we’ve worked hard on is diversity and inclusion. Forty percent of our employees are non-white, which in home furnishings is quite rare. That is something we focused on, made a point of in the recruiting process, and tried to address at the root. When you look at who is graduating from design programs, it is very non-diverse. So we started a scholarship program to bring diversity into education.

How would you describe your management style and how has it evolved over the years?

I’m not good about being introspective about that. I think my team would say that I’m always on. I’m not a hands-off leader. I am in it. I am hopefully very clear with my team about what expectations are. We just got an employee survey back and 99% were clear on what [they had to do]. Mission accomplished!

It’s also just making sure you say thank you a lot. The last two years people have been through the wringer. One of the things that has been important for us is to always make sure to say thank you to people and recognize what is happening to them and being a little more thoughtful and gentle than is often the case in professional environments.

What is the biggest misconception people have about the secondhand luxury market?

One, the size of it. I don’t think people realize how massive the resale market is. Two, the furniture market overall is highly fragmented, with very few well known brands. Three, the move of the furniture category online is still in the early stages, even after the pandemic. A big, highly fragmented market beginning to move online, is a very fertile ecosystem in which to create an online marketplace.

From 2017-2024, the global resale market is expected to triple to reach $130.6 billion. Before the pandemic, apparel was about half the resale market and home furnishings was about 11%. By 2020 , home became the fastest growing category within resale.  It’s really moving quickly. As a point of comparison, between 2021 and 2025, the traditional retail biz is expected to grow 20-24%. Resale is expected to grow 53%. That’s three times faster than traditional retail.

I think the reason it is growing so quickly is there’s a meta customer trend for individuality and uniqueness. That’s not new, but it is increasingly important. People want to present themselves in a way that’s unique. That’s hard to do when the only place to buy is big stores full of gray and beige sectionals.

Resale items are also immediately available. In vintage, there are no supply chain issues. Our median time to delivery is two weeks for furniture, which compares very well to the 8-36 weeks that many contemporary manufacturers are dealing with today.

Chairish is positioned at the high-end of the vintage market pricewise, but compared to high-end retail, it’s an enormous value. [The company encourages buyers to make an offer and negotiates pricing, just the way antique fairs and vintage shops do.]

The last but maybe most important benefit of vintage is the sustainability advantage. There is a two-sided benefit when buying vintage: You’re repurposing a piece and saving it from disposal plus you are avoiding the manufacture of something new and all the environmental impacts that come from that .

Out of good, fast, cheaper and green, you get all four. That helps explains why folks are moving to vintage.

What is the hottest product category on your site right now?

It’s almost always dining chairs. We do [well] with vintage Baker furniture, George Smith, Century Furniture, Ralph Lauren, John Dickinson, Vladimir Kagan, and the modernists like Roche Bobois. We also do really well with B&B Italia.

What’s on your trend radar?

Every Chairish item is tagged with its period, style, materials, brand, everything. We put it into a marketplace environment, and we are very quickly able to track what people are looking at, putting in their cart, telling their friends about. Because we have a wildly diverse catalog, it gives us a very forward customer and a way to look at [trend] events before anyone else. That’s been really fun. We do very timely boards gleaned from all that data.

Butterflies are trending, yes. The other thing is stripes, but not traditional color combos, it’s in really muted colors like lavender and mustard, or a dusty pink and mossy green. We’re seeing a ton of interest in Gustavian –I’ve been advised to called it Swedish – design, with powdery, muted finishes in lovely blue and green. There is huge interest in Swedish flatweave rugs. Tole plants are also doing well for us, along with Bobbin shapes—like the legs on casegoods.

We check what styles people are looking at, and the thing we’ve seen is traditional is doing really well. It something we internally call “the return to pretty.” It’s definitely happening. Rounded modern bulbous pieces in bouclé and millennial pink that were so hot have spread far and wide. It’s often presented in environments that are minimal and blogger chic. It’s beautiful and we still sell plenty, but I think with people being home and nesting, there’s an appreciation for layering with a more maximal approach and how to make it look its best.

What advice would you give to anyone eager to launch a new online [home] business?

A lot of people think they have to have everything figured out and completely perfected before they launch something. That’s natural.  But I think it’s important to do lots of small tests and try things. I think that is the most important advice I can give. Don’t spend a lot of money on something you have no market feedback on. Put something out there and learn and use that feedback. Then you can put the resources in and start to create things. Stay open to being wrong and leave yourself runway to iterate in the build.

When it comes to product, I hear, “I’m going to build this product and sell it on my website.” Building the product is probably the easiest part. Getting eyeballs on it is the hardest. It’s really expensive to get people to a site or a brand. Being part of a larger marketplace can solve a lot of problems. It doesn’t have to be an either/or experience. Create your own brand but participate in a lot of venues to get the word out and help customers know about you.

You have an expanding team, a podcast and a magazine. What’s next?

We’re lucky to work in a category that has so much interest, so much love for it and so much to talk and write about. What else has several TV networks dedicated to it? We’re looking at ways to help people navigate the category. Content is important to think about. We’re also very curious about how to bring Chairish to the physical world. We’ve spent the last nine years as an online brand, but we do see an opportunity to selectively explore the physical world as well. There are lots of models to do this. What you can expect to see from us is a range of small tests, small pop-ups or partnerships, maybe. From there we will make a decision.

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Chairish predicts butterflies will trend this spring

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