Career Code: This Wildly Successful Entrepreneur's Tips Will Inspire You

Written by Gabrielle Savoie

There's nothing quite like the thrill of coming across a vintage treasure when thrift-store shopping, but who has the time—or, more importantly, the eye!—to sift through antique shops and flea markets? Anna Brockway, that’s who. This brilliant ingénue thought of bringing the joy of vintage décor shopping online, and in just three years turned an entire industry on its head. 

With a background in art history, the fearless and savvy Columbia University graduate kicked off her career in the world of fashion advertising, working her way up the ranks of Levi’s,where she ultimately became vice president of marketing before the lightbulb watershed moment hit. 

With a natural discerning eye, Brockway honed her skills as a vintage décor shopper throughout her years as a wife and mother. She launched Chairish with her husband, Greg Brockway (whom you know as the serial entrepreneur and co-founder of TripIt and Hotwire). Her goal: fusing the rush of shopping for gently used vintage items, with the ease of online shopping. It’s safe to say that she’s succeeded. 

The vintage décor powerhouse has been a recurring guest on NBC’s Today Show, and has amassed over 75,000 followers on Chairish's Instagram. Ready to get inspired and take some notes to pursue your own workplace dreams? Scroll to follow Anna Brockway’s invaluable tips for success.

In civilian terms, how would you describe your job?

"It’s my job to make Chairish chic, famous, addictive and beloved. I would also describe my job as an extraordinary amount of fun in the same way that running a summer camp for manic Broadway players is fun."

What part of your job would people find more surprising?

"I spend a lot of time studying data. Most people are surprised that I, the art history major, am good at this!"  

What did you wear to your first job interview?

"My first job interview ever? A watermelon-pink suit. It was the ’90s, so let’s just leave my hair out of it. Terrible flashbacks happening. Right. Now."

Who would you like to have a 30-minute meeting with?

I’d meet with Katharine Graham, the late publisher of The Washington Post who led the paper through its disruptive coverage of Watergate, ultimately resulting in Nixon’s resignation. Katharine reinvented herself from a wealthy, educated wife into a world-class business leader who was absolutely fearless in taking on the big boys. She was the first female Fortune 500 CEO. Hello, badass!"

What are your go-to resources for keeping up to date on your industry?

"My best resource is always my network of friends and colleagues. To learn home décor trends, I spend lots of time at fleas peering into the carts of others! For technology information, I dive into Andreesen Horowitz’s A16Z newsletter, and I love Adam Lashinsky’s tech reporting for Fortune."

What is the one thing in your career that you've regretted?

"I regret it every time I don’t follow my instincts. I’ve made this mistake in hiring, and it’s just a big disaster all around."

What are the five top qualities you look for when hiring?

"Hustle: If I gave this person a big new challenge with minimal instruction, would she be able to figure it out? 

"A sharp eye: Does she have great taste? It matters 100% in my business. 

"Curiosity: Is this gal eager to learn? Is she okay saying, "Don’t know, let me find out"? 

"Directness: Is this person afraid of me? Will she level with me? 

"Humor: Can she laugh out loud? An appreciation for the ridiculous goes a long way." 

What do you wear to work to feel powerful?

"Well, I am pretty short, so tall heels are definitely part of my power pose equation! Add massive vintage earrings, narrow trousers, my Art Deco bracelet from my husband, and I’m off to the races. Plus, I’ve always regretted a print."

How would your assistant describe you?

"Always on, a little profane, but quite maternal."

What do you do when you're feeling uninspired?

"Pop on flats, sunglasses, and my old camel coat, and go for a long walk through a new neighborhood. Shopping ensues. I also find writing thank-you notes dissipates any funk."

What's the best way to quit a job?

"Gratefully. Even in the most unhappy situations, it’s likely you learned something. So I recommend giving fair warning, thanking everyone for the opportunity, and always keeping in touch. I never speak ill of my exes."

What is your go-to lunch?

"My native habitat is the lunch counter at Cotogna, tucking into a chopped salad. I also make a mean avocado toast on sourdough with Maldon sea salt and red pepper flake sprinkles."

What are the most common mistakes entry-level employees make?

  "For both, I think it’s not allowing ourselves to be curious. The pacing of business is so fast, now that folks just dive into executing their to-do list ASAP without much thoughtfulness. We often miss the important, subtle clues that ultimately can determine if all our work is successful or not. Why? Senior leaders are afraid to appear devoid of having all the answers, and beginners don’t want to seem inexperienced or lost. Everyone is afraid of being behind. Fear drives bad decision-making, so my advice is to slow down a bit, get humble, and really think it through. Lastly, on an operational note, simply turn up to work on time. Lateness is sloppy." 

Who do you love to follow on Instagram?

"@derekblasberg: Is there anyone having more fun? And how is he not exhausted? 

"@thejealouscurator: She never fails to inspire with fabulous (and affordable) art. 

"@tome____: I don’t have a sweet tooth, but this bakery’s exquisite photography could change all that. 

 "@lindaandwinks: Dear Lord, hear my prayer: May I look this good when my hair is white. 

"@chairishco: Because it’s pictures of all my favorite spaces!" 

What are your morning and evening rituals?

"I wake up very early, at 4:45 a.m., so I have time alone. I meditate, exercise, make coffee, and pick my favorite items for our homepage all before the house wakes up. It’s a centering time for me before ‘working mom at a startup’ insanity kicks in. At night, after family dinner, flashcards, and four or five unsuccessful attempts to tuck the kids into bed, I take a hot bath, occasionally accompanied with a sip of whiskey. Then into bed with a good biography. I have a no-work-one-hour-before-bedtime rule so I can separate from the day." 

What's the best advice you've ever received? 

"Big wedding, small wedding—you still gotta call the florist." — Nana RitaI think her point was, no matter what you do, it’s going to be a lot of time and treasure, so why not make it great? It’s stayed with me. I loved her so!" 

What are you working on right now that you're most excited about?

"We are working on launching a new type of shopping event! It’s based on the rip-roaring success of our beloved Instagram Sales, where we sell fabulous finds from the world’s greatest antique and flea markets live on our Instagram account. These shopping events developed a rabid cult of vintage-obsessed shoppers, and we are looking to make them even bigger on Chairish itself. Stay tuned!"