#Girlboss Week: Maddy Grayson

To recap, for the next 4 days, we are taking a page (literally) out of Sophia Amoruso's bestselling book, #Girlboss, and featuring 7 lovely powerhouses who also happen to be Boobypack Angels.

We hope they'll inspire you to take some chances and fight the good fight. In Sophia's words: “While you’re reading this, I have three pieces of advice that I want you to remember: Don’t ever grow up. Don’t become a bore. Don’t ever let the Man get to you. Okay? Cool. Then let’s do this.”

#GIRLBOSS for life.

Introducing #Girlboss Maddy Grayson: 

When Maddy couldn't find her favorite classic American brands in one place, she didn't just resign herself to J.Crew and call it a day. She, along with cofounders September and Jocelyn, decided to raise nearly half a million bucks and launch an ecommerce store called Tuckernuck– a one stop shop for all things preppy and chic. And when she couldn't find the right pre-wedding outfit for herself and her maids, Maddy didn't just resign herself to her hubby's shirt or a floral robe. NO she did not! She ordered custom Bridal Boobypack Tankinis! (She's the one in white below) That's what we like to call a "go-getter," a "do-er," quite simply a #BOSS. With an eye for fashion and a mind for business Maddy Grayson is one to watch. 

1. What do you do? What is your typical day like? 

I'm one of the 3 founders of Tuckernuck, an e-commerce site that aggregates and sells product from 150+ unique brands. I wear a lot of hats, but my main roles are Buying and Content Production.

A typical day varies based on the time of year. The production side requires me to be in the studio or on location with our creative director, photography team and models (aka our friends) when we are creating lifestyle e-catalogs. When I'm not running around like a mad woman, I'm buried in spreadsheets, vendor line sheets for future season buys or on the phone with potential new brands to add to our assortment. That’s my favorite part of the job–working with small businesses.

2. Can you tell me a bit about your company? How many work there, have there been any recent milestones, what are the near/far term goals etc.?

Tuckernuck is the one-stop online shop for men and women who love classic American style. From up-and-coming brands to iconic labels like Barbour and Saint James, we style 150+ brands together in one aspirational yet approachable online space. We actually just launched our 23rd lifestyle e-catalog! 

I work with a small, scrappy team of 8 full-time, smart, driven, no bullshit ladies and two incredible gents who keep things in perspective. Two of my closest friends from Penn, my sister, and my high school Lacrosse teammate are whom I get to spend my 12 - 14 hour days with, so I'm definitely lucky. 

Recent milestones...We moved all of our inventory to a warehouse in South Carolina so fulfillment is handled by a team down there. We launched our first collection of vintage items in our "Tuckernuck Bazaar"– selling out of 1980s NFL Sweaters almost instantly. Our main focus though, with our exciting organic growth the past 24 months, is finalizing our investor deck for a strategic fund raise in the coming months. We’re also planning to open our flagship store in an industrial space in Georgetown in the near future! 

3. What's the biggest difference between your current job and your last job?

I was lucky enough to have worked for a fairly young company before this. It was an ideal starting off point because while the founders taught me a lot about the retail and manufacturing industry, they also gave me a lot of space. I had the opportunity to explore what I was really interested in with few boundaries from day 1. Now I spend a lot more time worrying about big picture direction and everyone's happiness, company culture etc. along with the nitty gritty details. It's more emotionally exhausting. I feel a lot more weight on my shoulders, but it's amazing to be building something that matters and is my own. 

4. What keeps you motivated?

My team and our vision. E-commerce clearly is in its infancy. I think there's so much to be said about branding a retail company online in a truly authentic way. We are scrappy, analytical and hard working, but we also never forget to laugh and we don't take ourselves too seriously. I think this is carried through in our photography, copy and overall message. Using friends as models, shooting lifestyle catalogs at family friends' houses, telling the stories of the founders of the small businesses we sell and represent… We're ready to take on lifeless J.Crew and overly pretentious Ralph Lauren! May we always give our customers new discoveries and inspiration to get out and do things. 

5. If you could have dinner with one famous person (dead or alive) who would it be and why?

It's a tough call between Katharine Graham and Martha Stewart. I've read both their books multiple times and think they’re both amazing female leaders. Martha was clearly ruthless and persevered with a brand, a way of life, that makes me feel warm and fuzzy. What an idealistic, picture perfect existence she still portrays. I love how she started as a caterer ("An Uncatered Affair") and ended up with a multi-million dollar enterprise.

Katharine Graham inherited her family's paper the Washington Post. She was the one in charge during Watergate and it’s incredible how under her command, the Washington Post rose to New York Times level authority.

Both women showed a ton of grit fighting for their success, which I respect tremendously. 

6. Who are your role models?

My Mom and my Dad. My Mom somehow managed to work full time as a bad ass Real Estate developer (usually the only woman), raise 4 kids (never miss one of our games), and make dinner for us every night without a single complaint. She loves what she does and she always says there's nothing we can't do. My Dad is the hungry entrepreneur, always pushing the limits, taking risks and never giving up. He started a company in Washington and ran it for 20 years. His level head and fair attitude created a really fun work culture with loyal employees who stayed along for the whole ride. Both of them have been sounding boards for us as we endure this crazy roller coaster called scaling a startup. They help us keep things in perspective and are a major source of encouragement.

 7. If you had to pick one quote/phrase to live by, what would it be?

"There is no substitute for hard work."

 8. What are your top three personal/professional highlights or achievements from 2014?

  • Getting featured on the cover of Matchbook Magazine in February
  • Getting MARRIED in June on Nantucket
  • Moving our inventory to a warehouse to South Carolina (But honestly, every time we launch a catalog I feel like I finished a term paper and feel a huge sense of accomplishment!)


If you want to shop Maddy's look above, email info@boobypack.com for a custom mockup. If you want to buy Sophia's book, go here. #GIRLBOSS for life.

Christina Conrad
Christina Conrad


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