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Boston Bosses: Hadley Douglas, Co-Owner of The Urban Grape

4 min read

Balanced Hustle is launching a monthly panel series for bad-ass entrepreneurial woman who want to connect and meet like-minded people. We’re digging deeper than traditional networking events and connecting a strong community of Boston women. Each week, we will be featuring Boston Bosses in the community and asking the hard questions and getting insights that will help you succeed.


Hadley Douglas, along with her husband TJ, is the owner of The Urban Grape, a ground-breaking and wildly popular wine store in Boston. The store concept is simple, but revolutionary – Drink Progressively. Their system of sorting wine by its body, instead of by varietal or region, brings ease and an unexpected surprise to customers. The Urban Grape has won numerous accolades as Boston’s Best Wine store from both Boston magazine and The Improper Bostonian, as well as being named Best Wine Store in the Northeast by Vinepair, and a Top 100 Wine Retail Stores in America by Beverage Dynamics. Hadley’s background is in marketing, events, and philanthropic management. If TJ’s job is to sell what’s in the store, Hadley’s is to sell the store itself. The official voice of The Urban Grape, Hadley translates “wine speak” to UG’s customers in a clear, fun, and vibrant way. Additionally, Hadley is the author of Drink Progressively, UG’s successful wine education and food pairing book. Together, TJ and Hadley are the parents of two wonderful boys, Noah and Jason, who were each selling Pinot Noir on the playground by the age of three. When they’re not drinking and selling wine, they can be found hiking, skiing, and beaching it with their sons, and the family dog Zeus – an Instagram sensation in his own right.

How many years have you been in business?

Ten.

What is the problem you’re solving?

The wine world has a serious problem – it’s considered expensive, intimidating, and exclusive. We’ve got one mission at The Urban Grape – to make wine more accessible, and FUN, for our customers. We’re bringing you the best in beverage, but also meeting you where you are on your wine journey, not expecting you to keep up with ours. Everyone with an interest in wine can Drink Progressively!

Who’s your customer?

The Urban Grape has a diverse and thoughtful clientele that ranges from wine neophytes to seasoned collectors. We’re able to meet all of our customers’ needs – no matter their age, background, or spending level – where they are on their beverage journey in order to ensure a thoughtful and personalized customer experience for everyone. If you love interesting wine, beer, or spirits, you’re our customer.

Why are you different?

Our way of thinking about and selling wine – by the body of the wine instead of by varietal or region – is the most revolutionary thing about our store. But that new way of looking at the industry permeates everything we do. The Urban Grape is so much more than a wine store – we’re your event planner, your corporate beverage caterer, your cellar manager, your gift giver, and your wine teacher all rolled up into one. Concierge-style hospitality is in our blood.

What is your biggest challenge and how did you overcome it?

The challenges of running a small business are too endless to list. But, my biggest internal struggle is that I was raised by a stay-at-home mom, and cherished my constant access to her. It’s hard for me to allow myself to be a different kind of woman, and more importably mother, without all of the guilt that comes with not being as accessible. I put too much pressure on myself to kill it in meetings all day long and then come home and put a home cooked meal on the table, oversee homework, remember every friends’ name, etc. My entire staff laughs every day when my last words as I run out of the store are “I’M LATE FOR SCHOOL PICK UP!” (Again.)

What is the best piece of business advice you’ve ever received?

Keep it simple. Trust your advisors. Hire a good bookkeeper. Listen to your gut. Don’t avoid the tough conversations. You’re only as good as your weakest member. They’re business cliché’s for a reason – they’re the truth. But the single best piece of advice I’ve received has been to make sure you take space from your business regularly. You can’t be a creative leader if you’re burnt out. And entrepreneurial burnout is very real, and very hard.

What advice would you give to an inspiring entrepreneur?

I see a lot of women who are scared to ask for what they want in business. I’m always telling women who work with me or who are my mentees to believe in themselves and their products and to directly ask for business. We are allowed to engage, we are allowed to speak highly of ourselves, we are allowed to believe we are the best, we are allowed to believe that we provide the best service or product. If you don’t have the confidence for that on day one, there’s nothing wrong with a little fake it ’til you make it.


Interested in hearing more from Hadley? Hadley will be speaking on a panel at our first Balanced Hustle Kick-Off Event on March 9th. Get your tickets here.

About The Author

The WELL Team

The WELL Team

The WELL Team is dedicated to 360-degree view of wellness for the modern woman, with coverage of clean beauty, mindful living, fitness, recipes and more.

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