Podcast Summary: Reinventing How We Shop for Design with Anna Brockway of Chairish

Podcast Information:

• Title: Talk Shop with Ariel Okin: A Fenimore Lane Production
• Host: Ariel Okin
• Guest: Anna Brockway, Co-founder and President of Chairish
• Release Date: August 6, 2025

1. Introduction to Chairish and Anna Brockway

In this episode of Talk Shop, host Ariel Okin welcomes Anna Brockway, the co-founder and president of Chairish, an esteemed online platform renowned for its curated selection of vintage, antique, contemporary, and made-to-order home furnishings, art, and jewelry. Founded in 2013 alongside her husband, Chairish has grown to serve over 40,000 vetted design professionals and boasts a collection of nearly 1.2 million items. Anna's background in art history and extensive experience in the fashion industry, including a decade at Levi Strauss and Company, have been pivotal in shaping Chairish's unique vision.

"We don't like to do the same thing twice. Like, we like to mix it up." — Anna Brockway [00:00]

2. Defining Chairish’s Unique Style

Ariel opens the conversation by asking Anna to describe her style in three words. Anna describes Chairish as open-hearted, adventurous, and delightful, emphasizing the platform's diverse range of offerings from high-end rare finds to whimsical, eclectic pieces. This blend creates a welcoming and non-intimidating shopping experience akin to browsing with a stylish friend.

"Open-hearted is probably the one that sounds the funniest, but it's a really important part of the Cherish brand." — Anna Brockway [02:49]

3. Anna's Journey to Founding Chairish

Anna shares her journey from growing up in a design-oriented family, with her father working at Baker Furniture and Michael Taylor Designs, to studying art history at Columbia University. Her decade-long tenure at Levi Strauss & Co., where she held the position of VP of Worldwide Marketing, provided her with invaluable insights into brand building, vintage appreciation, and the importance of sustainability in fashion.

"Nothing is better than an old pair of Levi's. Right." — Anna Brockway [08:45]

4. Transitioning from Fashion to Vintage Design

The narrative transitions to Anna's personal life, where raising four children led her to embrace vintage shopping as a practical and stylish solution for furnishing multiple moving homes. Inspired by her husband's success in the tech industry, specifically his role in founding Hotwire, Anna conceived the idea of Chairish as a marketplace where individuals could buy and sell beautiful, pre-loved items with ease.

"We started it together in our dining room." — Anna Brockway [11:47]

5. Overcoming Early Challenges in the Business

Anna discusses the initial challenges Chairish faced, particularly with logistics and shipping. Early models involved storing items until sold, which proved unsustainable due to high shipping costs. Through strategic conversations and a focus on technological solutions, Chairish pivoted to a model where items remain with sellers until purchased, significantly reducing overhead and shipping complexities.

"Shipping something once is expensive enough. Shipping it twice... that's just too much." — Anna Brockway [19:33]

6. Building a Robust Business Model

Chairish's success is attributed to its dual focus on curation and technology. Anna highlights the importance of collaborating with interior designers, who are primary customers, ensuring that Cherish meets their needs by delivering exceptional quality and reliability. The team, including her husband Greg and CTO Andy Denmark, has been instrumental in developing the platform's technical infrastructure.

"You have the creative side of the business and the tastemaking side of the business." — Anna Brockway [15:42]

7. Growth, Recognition, and Market Trends

Over the past decade, Chairish has garnered significant recognition, including being named one of the best entrepreneurial companies in America by Entrepreneur magazine and the top "can't live without decorating app" by Architectural Digest. Anna delves into current market trends, such as the resurgence of Art Deco, the enduring popularity of wicker, and the increasing interest in Swedish flat weave rugs and mid-century art. Chairish's expansion into European markets through acquisitions has enhanced its inventory and global reach.

"A lot of art deco interest. I mean, unsurprisingly." — Anna Brockway [29:14]

8. Expanding Product Lines and Future Projects

Anna reveals exciting developments at Chairish, including the launch of estate jewelry, bags, and enhanced communication features that facilitate better interactions between buyers and sellers. Collaborations with celebrities and high-profile clients, along with participation in antique shows like the Parma Antique Show in Italy, are set to further elevate Chairish's presence in the design world.

"We're working on so many interesting things." — Anna Brockway [27:13]

9. Personal Insights and Inspiration

The conversation turns personal as Anna shares her favorite places to shop, drawing inspiration from renowned stores like Pieta Terra and experiences from prestigious events. Her favorite design book is a new release on Rosario Candela, reflecting her deep appreciation for architectural history and its impact on interior design.

"Favorite design book... Rosario Candela." — Anna Brockway [46:18]

10. Rapid Fire Round

To conclude, Ariel and Anna engage in a fun rapid-fire segment, revealing Anna's personal preferences:

• Favorite Food: Grandfather's chicken piccata ([43:27])
• Favorite Drink: Ranch water ([43:51])
• Favorite Film: Rushmore by Wes Anderson ([43:54])
• Favorite City: New York ([44:39])
• Tea or Coffee: Coffee with a splash of milk ([44:55])
• Favorite Weekend Activity: Visiting the San Francisco Flower Mart with her father ([45:46])

11. Final Words and Advice

Anna offers heartfelt advice to aspiring interior designers and shoppers: embrace flexibility, enjoy the process, and don't fear change. She emphasizes the importance of experimentation in defining personal style and the benefits of platforms like Chairish that facilitate easy transitions between different design choices.

"Don't take it too seriously... be willing to be experimental and try some things." — Anna Brockway [49:55]

Conclusion

This episode of Talk Shop offers an insightful look into Anna Brockway's journey with Chairish, highlighting the platform's commitment to curated vintage finds, innovative business models, and responsive customer service tailored to interior designers. Anna's blend of creative passion and strategic thinking underscores Chairish's position as a leader in the online design marketplace.

Notable Quotes:

• "We don't like to do the same thing twice. Like, we like to mix it up." — Anna Brockway [00:00]
• "Open-hearted is probably the one that sounds the funniest, but it's a really important part of the Cherish brand." — Anna Brockway [02:49]
• "Nothing is better than an old pair of Levi's. Right." — Anna Brockway [08:45]
• "We started it together in our dining room." — Anna Brockway [11:47]
• "Shipping something once is expensive enough. Shipping it twice... that's just too much." — Anna Brockway [19:33]
• "You have the creative side of the business and the tastemaking side of the business." — Anna Brockway [15:42]
• "A lot of art deco interest. I mean, unsurprisingly." — Anna Brockway [29:14]
• "We're working on so many interesting things." — Anna Brockway [27:13]
• "Favorite design book... Rosario Candela." — Anna Brockway [46:18]
• "Don't take it too seriously... be willing to be experimental and try some things." — Anna Brockway [49:55]