Lindsay Cates
Senior Manager, Communications and Strategy, U.S. Chamber of Commerce


August 30, 2022


TJ and Hadley Douglas, owners of The Urban Grape wine store in Boston, were the winners of the U.S. Chamber’s annual Dream Big Small Business of the Year Award in 2021 and received a $25,000 cash prize.   

As CO— by U.S. Chamber of Commerce prepares to announce the finalists for the 2022 awards next month, we caught up with TJ and Hadley on a recent visit to U.S. Chamber headquarters to hear more about what's changed in their lives since the win and how they used the prize money.  

One recent milestone: TJ and Hadley joined the U.S. Chamber's Small Business Council, a policy committee that assists in creating strategies on legislative, regulatory, and international initiatives to support small businesses around the country.  

The following has been edited and condensed for clarity. 

Q. Congratulations again on your Dream Big win - $25,000 is a huge prize! Tell us how you have used the money.  

TJ: It has been amazing. We were able to put the money toward creating a new company called Progressive Wine Company. It's a Massachusetts company, but we're buying grapes and working with a winemaker near the Russian River in Sonoma, California. In the wine we’re creating, we’re simplifying what people are feeling and tasting so that wine is accessible to all. We're also donating $1 for every bottle sold and for every piece of merchandise sold to a Foundation we're creating to support BIPOC students in pursuing the wine industry. 

Hadley: Check it out at @ProgressiveWineCo on Instagram and online.I loved starting Urban Grape, but this was the most fun project I've worked on. 

Q. What did winning Small Business of the Year mean to you? 

TJ: It was validation that Hadley and I run a tight business and all the work that we've done for the last 12 years has really paid off. It lit that fire of entrepreneurship and turned that flame up a little bit. 

Hadley: It inspired us to dig even further into our business and think about expanding, other opportunities, and how to grow our business. It gave us a lot of confidence. It was not only great to have the recognition externally, but internally we realized that we can take that next step in our business.  

Q. We’re getting ready to announce our Dream Big 2022 finalists. What is your advice to those new finalists—or any small business looking to grow?  

TJ: Going through the process really makes you take a deep dive into your own business. It makes you see your business in a different light, encourages you to stay on your path, and reinforces your mission of why you created your business.  

Hadley: The Dream Big programreally shows the whole country what you're doing. I think the U.S. Chamber is working so hard to find businesses and promote businesses that are looking at business in a different way and bringing new solutions to the table. Often, we aren't the businesses always getting the first access to funding, and to have the U.S. Chamber show this type of support is important. 

Look for the finalists for the 2022 Dream Big Awards to be announced in early September on CO— ’s website:

About the authors

Lindsay Cates

Lindsay Cates

Lindsay is a senior manager on the communications and strategy team. She previously worked as a writer and editor at U.S. News and World Report.

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