We recently talked to Glitter Guide founder Taylor Sterling about the pits and peaks of putting on a large-scale conference. We really opened up about the challenges but also the huge highs of hosting Flea Style Summit.
Read the article in full here and we hope you’ll join us for this incredible day jam-packed with meals, empowering panels, educational workshops, a Sugarfina candy station, Blushington beauty bar, shop small retail area and more! Taylor Sterling is also pre-recording an interview with us to run during Summit’s Office Style Workshop, which Glitter Guide is co-hosting. Learn more about Summit’s plans, perks and tickets here!
Brittany Cobb is no stranger to hard work. After years working tirelessly in journalism, she decided she wanted to have more time and freedom to raise her family and do things she was truly passionate about. Fast forward nine years and she’s now running the very successful Flea Style Summit.
Have you ever wondered what goes into running a conference? We sure have! We sat down with Brittany to ask her about all the details—from the inspiration, how she gets sponsors and how she juggles everything while raising two kids!
And, be sure to check out Brittany’s fabulous home tour, which is sure to provide some decorating inspiration!
TELL US A LITTLE ABOUT YOU AND WHAT YOU DO?
My name is Brittany Cobb and I’m a 34-year-old mother of two. I was born and raised in Southern California and moved to Dallas at 18 to attend Southern Methodist University. I graduated with a journalism degree and spent most of my 2os penning articles for publications like The Dallas Morning News, Forbes and Lucky. I spent a year in New York City as a freelancer before moving back to Dallas to take on the DailyCandy city editor role.
In 2009, I started a little side project called The Dallas Flea and filled it with cool creative people I met through my journalism career. A week before my first market, I was laid off from DailyCandy and decided that day that the journalism world was facing tough financial times and I needed to figure out my next career move. I had always loved interior design and started fluffing my friends’ spaces. Those little jobs turned into big jobs and within a couple years I had a full-fledged design firm called Cobb Interiors. I was decorating homes for everyone from Hollywood starlet, Kate Levering, to Dallas Cowboys owner, Jerry Jones. My little flea market was still a side hustle and kind of dying in the wings because I had little time to foster it.
In 2015—after getting married and having two children—I made the tough decision to give up my booming design business to go back to the little passion project that made my heart so happy. I wanted to raise my kids on my terms and my design jobs were just too demanding. I changed the The Dallas Flea’s name to Flea Style, and today, we have huge curated pop-up markets in Dallas and Houston, a cool conference for creatives, artisan workshops at our Dallas headquarters and an online shop offering handmade, vintage and one-of-a-kind wares that we collect at flea markets and collaborate on with our vendors. In a nutshell, we’re a hub for makers and shakers that want to shop small, find unique lifestyle items and learn ways to start a creative business or grow their current passion project.
WHERE DID THE INSPIRATION FOR THE FLEA STYLE SUMMIT COME ABOUT?
I grew up in an entrepreneurial family and saw the hard work and special sauce it takes to make a business successful. As our shows grew and I got to know our vendors better, I learned about their struggles in the small business world and wanted to help. Sometimes, people need real advice and education. Other times, they just need a little lift and inspiration. I wanted to create something that bridged those worlds and sprinkled in lots of fun, too. We call Flea Style Summit “a cool conference for creatives.” The backbone is based on education and hard facts from creative influencers that have walked the walk, but we cushion the serious stuff with engaging activities, a Sugarfina candy bar, margaritas and retail therapy from our amazing vendors. I really believe we strike the perfect balance of informative and fun!
WHAT ARE YOUR TOP THREE GOALS FOR THE SUMMIT? WHAT WOULD YOU CONSIDER A SUCCESS?
We aim to inspire, empower and educate first and foremost. If you leave feeling those three things, we’ve achieved our goal. We hope people network and make lifelong business connections and friendships, too. We’ve had several dozen people start companies post-Summit from the information and inspiration they received. I tear up when I hear those stories.
HOW DO YOU PLAN FOR SUCH A COMPLICATED EVENT? HOW LONG DOES IT TAKE TO PLAN?
Planning a conference has so many layers. It takes us about six months because we have so many other balls in the air at one time with our shows, online shop, blog, etc. It starts with courting panelists and curating a mix of people that have a wide range of stories and advice. I personally talk or meet with everyone to ensure that our mix is diverse, relatable and inspiring. From there, there are thousands of tasks from securing a venue, setting a budget, selling tickets, designing the website, interviewing panelists for the blog, creating menus, setting up the retail shop, ordering rentals, buying swag…the list is seriously a small novel!
WHAT ARE THE BIGGEST CHALLENGES WHEN ORGANIZING A CONFERENCE?
There are lots of challenges, but the hardest is probably creating the panel and then organizing their schedules, flights, Q&As and itineraries. I place a huge emphasis on creating a panel mix that will mingle well together so that the comfort level translates on stage. There is a lot of strategy and hair-pulling that goes into making that magic.
WHAT IS YOUR FAVORITE PART OF THE CONFERENCE?
I love that people don’t want to leave once it’s over! Last Summit, I sat down for an hour with nearly a quarter of the crowd after happy hour with a mic to answer more questions. People are sponges at this event and it gives me goosebumps to think of all the things they will do afterward with the information and inspiration they receive from our panelists, workshop mentors and fellow attendees. The energy, excitement and big eyes I witness that day reminds me of why we put in all the hard work to make the event happen.
WHAT WOULD YOU RECOMMEND TO SOMEONE TRYING TO DO LARGE-STYLE CONFERENCES?
First of all, you have to love this industry. When you’re in the business of educating and inspiring, guests can feel it immediately if you miss the mark and don’t organize the event with heart. From there, I would say to make sure you have the time it takes to pull it off and some serious multitasking skills because there are so many details involved ranging from audio/visual meetings and meal tastings to space planning. You also need a following to fill seats with guests. In a nutshell, it really takes someone that is engaging, authentic, a big-picture thinker and extremely detail-oriented.
YOU HAVE TWO KIDS. HOW DO YOU JUGGLE ALL THIS WORK?
I’ve learned over time that organized chaos is my comfort zone. When I’m busy and juggle a lot, I actually thrive, excel and do my best work. So I guess I’m saying that it’s a bit in my bones. But I also have help: I have a great team in place and a nanny to assist with childcare. I learned I had to strike a work/life/wife balance, and for me, it was creating strict work hours so I can get a lot done during “office time.” Once I’m home, I’m able to be mom and wife and focus on my family instead of catching up on work stuff—most of the time! It’s not a perfect balance—I don’t believe there is such a thing—but I’ve found one that works for me and doesn’t leave me with tons of mom guilt.
WHAT’S THE BEST STRATEGY FOR GETTING SPONSORS FOR EVENTS?
Know your audience and try to work with companies that fit your mission, idea and demographic. Approach them with a beautiful deck offering a good mix of images, facts and figures, as well as a proposal (whether a firm one or a loose idea initially) that benefits their brand as much as yours. I’m really big on meeting with people versus just shooting over an email whenever possible to connect and relay the message better.
HOW DO YOU COPE WITH SPEAKER’S ANXIETY FOR SPEAKING AT YOUR CONFERENCE?
I am very lucky that I don’t have that problem. I wouldn’t host a conference if I did. I also strive to create a very casual, Q&A-style format so that there really aren’t nerves on stage—it’s intended to feel more like a fireside chat or old pals getting together to exchange stories and even laughs. Our panelists have been known to drink margaritas or wine on stage (me too!)!
WHAT ARE YOUR TOP FIVE APPS FOR STAYING ORGANIZED?
Dropbox is our work bible; it holds everything from our logo deck to photo shoot images and panelist contracts. I live by my Google calendar and documents (I use the documents tool for our company “task calendar” that I update daily). I don’t really have any other apps for organization, but do live on my PayPal, Shopify, Eventbrite and Venmo apps for other Flea Style operations stuff.
FIVE THINGS YOU COULDN’T LIVE WITHOUT DURING THE WEEK? WEEKEND?
My iPhone, laptop, iced latte habit, giant vintage Marni leather tote bag and ChapStick get me through the work week. Pretty much the same goes for the weekend, but I can finally exchange my messy bag for my messy kids!
Flea Style Summit is Saturday, Sept. 23 from 9 a.m. to 5 p.m. in Dallas. The cool conference for creatives inspires and empowers 200 attendees to take their brands and life goals to the next level through informative panels and mentorship.