CEO Regine T. Rousseau on Making Wine Her Work

Regine T Rousseau of Shall We Wine / Photo by Alisha Sommer

It was a study abroad program in France that sparked Regine T. Rousseau’s lifelong love affair with wine. Today, the Chicago entrepreneur will be the first to tell you that if you love what you do, it’s not really work.

The founder of Shall We Wine, Rousseau, 46, has grown her Chicago-headquartered company into a nationwide network of specialists that help importers and distributors host in-store tastings at their retail accounts.

Shall We Wine also plans wine and spirits focused corporate events and offers pop-up wine and cooking parties at local restaurants, galleries and other venues.

“I made wine my career by accident,” says Rousseau.

Raised in Haiti, Rousseau came to Chicago in her teen years to go to college. But it was that year abroad living with a French family who owned a wine shop that helped her find her calling.

“It was a really beautiful home, not luxurious, but comfortable and spacious and they lived in the forest and had glass walls and I thought ‘Oh my goodness. I’ve just walked into my future,’ ” she recalls.

The table was set for dinner with bottles of Bordeaux and Rousseau says the father of her host family “introduced each one… Even though I didn’t know anything about the wines, I fell in love with the culture of wine.”

And today that is what she sells—the wine lifestyle.

It’s all about the wine lifestyle

After graduating from Knox College, Rousseau worked in sales, not just for the wine industry, but pharmaceuticals and consulting services as well.

Along the way, she maintained an interest in wine, but was stumped when it came to “how to monetize it, how to create a business around it.”

Between 1997–1998 Rousseau launched Shall We Wine, but then took a break while she wrote a wine column and did private events.

But by 2013, she had figured it out. “I wanted to travel, write, expose people to wine, and I wanted to sell and I wanted to manage people, because I found out along the way I was really good at that and enjoyed it,” says Rousseau.

Building her business 

When the company she was with downsized, Rousseau decided it was time to jump into the wine industry with both feet.

She earned a Level Two certification at the International Sommelier Guild and, after giving up her luxury apartment and paying off her car and debts, rented a small apartment in the historic Bronzeville neighborhood on Chicago’s South Side. This is where Rousseau reinvested in Shall We Wine.

She calls it a demo company “working with clients to help them sell bottles of wine at the store level.”

“I like to write, so I’m going to do online reviews and am going to blog,” says Rousseau. “And I wrote a book [Searching for Cloves and Lilies: The Wine Edition (CreateSpace Independent Publishing, 2018)]… This year we’ve done one trip to Oregon and more wine trips are planned. I’m building a company that’s all about a wine lifestyle.”

The Day-to-Day

Rousseau’s wine lifestyle includes 20–40 wine tastings on weekends and private events on weeknights depending on the season.

“For example, Hampton University was hosting their black alumni chapter. We were hired to do the food and wine. I work with a chef and he made wonderful food, I just talk about the wine,” she says.

There are always lots of conference calls for Rousseau. “I’m either selling programs or setting up corporate events.”

With a wry smile, she adds, “My hot, sexy Friday night will be spent doing invoices.”

Rousseau has a part-time team of three employees and more than 200 contractors nationwide who can execute demonstrations and tastings for both wine and spirits. However, she is expanding and looking for more.

“There’s a link on our website or they can send an email to hr@shallwewine.com.”

Published on July 2, 2019
Topics: A Day In The Life
About the Author
Leslie Gevirtz
Contributing Editor, Business

An award-winning journalist, Gevirtz spent more than 20 years covering disasters—natural, political, and financial—before becoming Reuters’ wine correspondent; a beat that guaranteed her colleagues were always glad to see her.



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