Regine T. Rousseau, CEO of Shall We Wine, on the future of wine entrepreneurship
In the first episode of our series on Innovation In Wine, we sit down with founder & CEO at wine consultancy, Shall We Wine, Regine T. Rousseau.

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The wine market is unpredictable—beholden to the whims of demanding consumers, supply chain challenges, regional regulations, and trends that threaten to upend established norms. In the middle of it all are the wine professionals who teach, grow, sell, and innovate in the space. In this new series on Innovation In Wine, we’ll speak with four experts at the top of their fields. Our first guest is none other than Regine T. Rousseau, founder & CEO at Shall We Wine, CWO event speaker, and WSET Level III Sommelier.
In this insightful episode of the CWO.digital podcast, Todd sits down with Regine to discuss her journey into wine, from her roots in marketing and storytelling, to her fascination with how AI may drive the industry forward.
Insights you can look forward to in this episode include:
[01:49] Why adaptability is your greatest strength as an entrepreneur
[03:29] The unique challenges of marketing wine
[05:30] How to make small, digestible steps in your wine knowledge journey
[08:34] The innovations of marketing to new consumers
[11:34] Wine trends and AI’s influence on wine
[15:58] The digital future of wine entrepreneurship
[19:35] The implications of tariffs for the alcohol industry
[20:50] Reading and advice for curious wine lovers
Todd: Welcome to CWO.digital, where we’re talking about innovation in wine. Today’s guest is Regine T. Rousseau, CWO wine expert and CEO of leading wine and spirits marketing consultancy, Shall We Wine.
Among her many accolades, Regine holds an International Masters Sommelier’s Guild Level 2, as well as nominations for Wine Educator of the Year. She’s appeared in Forbes, The New Yorker, and the Chicago Tribune in recognition of her tremendous work across the wine industry, and what Regine doesn’t know about wine is not worth knowing.
So, I’m extremely excited to say, Regine, welcome to CWO. Digital!
Thank you so much for joining us on the show. It’s such a pleasure to have you here. I was hoping we could start by getting to know you a little bit better. Would you mind telling our listeners how you came to choose your career?
Regine: Thank you for having me! I love this question because I love going back and remembering where I was vs. where I am now.
In terms of my career, marketing and sales storytelling has always been the foundation. Wine became this natural extension for me because I was introduced to wine as a vehicle for communication; as a tool to bring people together. So my love for storytelling was just this natural progression to starting Shall We Wine.
Todd: The more and more I speak to wine experts like yourself, the more storytelling seems to be what shines through. Whether it’s from the people making the wine or the land where it’s grown, or anything to do with how it’s marketed; it’s all about storytelling.
What has been your biggest lesson since diving into your career?
Regine: Wow. The biggest lesson I would have to say is that adaptability is everything. When you’re an entrepreneur, you have to be flexible. You have to be able to adapt to changing times.
During COVID I had to completely shift my business, because prior to COVID, everything that I did was in person. I quickly pivoted to virtual events and leveraging my experience doing television and digital marketing to relaunch or reintroduce the business on a different platform.
So yes, you really have to be adaptable.
Todd: That’s a really good lesson for anybody in life. I’m super curious to know, are there any unique challenges to wine marketing compared to other types of marketing?
Regine: Yes, because wine is so highly regulated. I think that makes it difficult, because the way that you can market wine in one region is very different from another. So regulations and compliance can be a hindrance.
Wine marketing is also difficult because we have to demystify wine. Earlier today I met with a photographer and I asked her if she is a wine drinker. She said, “I’m trying”. I was so confused by that! You know, it’s just a drink. You drink it if you like it. We had this conversation about how she felt like in order for her just to say, “I do love wine,” she has to come with knowledge, as opposed to just a curiosity. So I think demystifying wine makes it difficult to market.
The last part that makes it difficult is that the market is saturated. There’s a lot of competition, and a lot of really good wines. I think that makes it difficult for the consumer to make a decision.
Todd: Absolutely. The barrier to entry can feel a little bit intimidating. A lot of these labels are not written in English, for example, and if people don’t speak French or Italian or any other languages, they may not know where to begin.
How do you go about helping people make that leap from simply enjoying wine as a drink to learning more about it? How do you help them bridge that gap?
Regine: The most important thing is that I try to make it accessible and start with curiosity. I like to say follow the bottle. If there’s a bottle that you love, that you’ve enjoyed, then open it. Drink it. Then get curious about it. Flip it over, read the back label, find out where the wine comes from. Read about the region, and then maybe eventually visit the region. These small steps make wine a lot more digestible.
The other thing that I do with my company is a lot of wine pairing events that go beyond food. For example, I do an event called Wine & Art. We take art lovers, and I pair wine with art pieces so that we can have a discussion about the history and style of the wine, before the curator talks about the history of the artwork and the background of the artist.
I also have a book about where I pair wine and poetry. It’s about making connections to wine that maybe don’t seem intuitive. But what it does is bring people over to wine who already have an affinity for art, and for culture.
Todd: That’s such a brilliant idea. As a non-expert, wine to me feels like one of those few things in life that is a mixture of art and science. There’s artistry in how it’s made, but there’s also chemistry there. Do you think there’s any truth in that?
Regine: I think you’re absolutely correct. You know, I’ve interviewed winemakers and asked them, “is it more of an art or more of a science?” Everyone has said it’s both. You have to respect the science, but understanding the science allows your artistic side to shine through.
Todd: That’s where the magic happens, I suppose. But if you don’t have the groundwork of that science right, then it doesn’t matter how creative you are. You’re not going to end up with something that anybody really wants to drink…
Regine: Yeah, absolutely!
Todd: Let’s talk about innovation now. A whole new generation of consumers are just beginning to dip their toe into wine. And they maybe don’t want to drink something that feels old.
Regine: You know, we keep talking about younger consumers, but there are also older generations who may not have been introduced to wine yet. I think that we can use ecommerce tools to drive sales. But in terms of innovation, we can also talk about winemaking techniques like low intervention, no sulphides, biodynamic. These things are not new, they are old. But they are helping the industry.
Todd: People of an older generation mostly just cared about how much a wine cost and whether or not it was supposed to be good. But nowadays I think there is this much more interest in the story surrounding the wine, as we talked about. People want to know how it was made, is it full of chemicals? Was it made by people who are happy, things like that.
Regine: That a great point. We are seeing a different conversation. People are a lot more concerned about sustainability, how the product is made, who’s made it, and whether or not they’re being treated fairly. These are conversations that I didn’t have when I first started in the wine business in the late nineties.
Todd: It does feel like there’s a little bit of a revamp going on with the language and imagery surrounding wine. Do you try and predict these trends before they emerge? Or do you focus more on the current scene?
Regine: I really focus on what’s in front of me. But I’m very interested in what everyone else thinks the trends are. For example, a few years back canned wines were becoming the buzzy thing. I had to be aware of that.
Todd: Of course, it’s so much more important to focus on what’s happening now, and how can you get more involved. That said, I am curious about the future. This is a question I’ve been asking a lot of people lately on this podcast. How do you predict the world of wine will be different ten years from now?
Regine: I had a client send me an AI-generated wine review recently. From my very limited understanding, they pulled together data from various sources, and they aggregated it to create a score based on what this AI tool was able to find online. I think that’s very fascinating. I don’t know if I have a 100% opinion on it yet, but I’m really interested in how AI can help as me as an entrepreneur.
Instead of a consumer going straight to their sommelier or wine shop, I can see them going to ChatGPT creating their own wine list to understand their preferences.
I think that there are some flaws in this now, because wine involves taste, right? But I find it really fascinating, and I do think it can help push the industry forward if these tools are used properly.
Todd: It’s a bit of a knotty puzzle to unpick. I’m not sure how I’d feel taking wine recommendations from a machine with no tongue, that has never drunk a glass of wine in its life! But at the same time, no human being can know absolutely everything about wine in order to give a truly all-encompassing recommendation. So it’s going to be really interesting to see what happens next.
Regine: One of the ways that it can help is with learning. This is such a dense subject… I think these tools can be really beneficial in helping organize your thoughts and helping to create a system where you can process all of the information.
Todd: Here’s a bit of an out-there question. If you were organizing a big summit for the whole wine industry to get together, what would you set at the top of the agenda?
Regine: You know, this is pretty selfish, but I would say the future of wine entrepreneurship. I get a lot of calls and questions from people who are interested in the wine space. They might be interested in becoming a distributor or an importer. There are a lot of people who are wine educators and event planners. I would love to talk a little bit more about the future of entrepreneurship. What does that look like in 10 and 20 years? What will our industry need? What kind of businesses have we not even thought of that will serve our industry?
Todd: And what do you think the future of entrepreneurship looks like?
Regine: I think it has to do with virtual reality tastings, and more digital experiences. I don’t imagine we will ever lose the appeal of gathering. But I do think we will see more virtual reality tasting and ways of reaching a wider audience through technology.
Todd: There’s this quite romantic idea that I have about wine tourism. You know, I can’t visit every winery that I want. But it would be wonderful to get a virtual reality tour of some of the world’s most exciting vineyards.
Regine: Absolutely, absolutely. There’s nothing that can replace traveling. I recently travelled to the Lombardy region, and just being there seeing everything, tasting everything… there is nothing more valuable. But also, as you said, not everyone has the time or the resources.
Todd: I think a lot of people would really connect with that. That’s exciting. Okay, we’re nearly running up on time for our call today.
We’ve touched on AI, we’ve touched on marketing and things like that. I’m curious, is there anything going on right now that those of us outside the industry don’t know about? Anything exciting that you and your fellow wine experts are all having heated discussions about?
Regine: Wow. Well you know, I don’t like to leave on a negative note. But there’s a little bit of panic now. We are in a time where we may be looking at tariffs. That’s the conversation that we’re having. We are a resilient industry and people are hopeful. But to be 100 percent honest, we’re concerned about that, especially here in the States.
Todd: Before we part, could you recommend any books or documentaries, that touch on the topics we’ve discussed today?
Regine: One of the books that I love very much is called Big Macs & Burgundy. It’s all about pairing wine with everyday meals. It really helps the consumer find the joy in food and wine pairing. She writes in such a way that it is so pleasant to read, and you want to try all of her pairings. I think that that’s what we need to do; get people excited about the joy of food and wine.
Todd: It’s such a magical thing. That sounds like an excellent book. I will definitely be checking it out and I hope our listeners do too.
One final question for you, Regine, before we go… If you could leave our listeners with one last piece of advice to help them get more out of wine, what would you like to say to them?
Regine: Stay curious. Don’t let wine culture intimidate you. Wine is here for joy. So just enjoy it.
Todd: Thank you so much, Regine. It’s been an excellent conversation.
Regine: Thank you.
I’d like to thank Regine Rousseau again for appearing on the show and thanks to you for listening. As always, you can find more podcasts and articles at CWO.digital, and keep an eye out for more episodes coming soon.
Until then, thanks for listening.
I'm really interested in how AI can help me as an entrepreneur. Instead of going straight to their wine shop, I can see customers going to ChatGPT and creating their own wine list.
– Regine T. Rousseau, Founder & CEO of Shall We Wine
About
the guest
Regine T. Rousseau ,
Founder & CEO, Shall We Wine
Regine T. Rousseau is the founder & CEO of Shall We Wine and holds a WSET level three and an International Master Sommelier’s Guild level II. In 2020, she was a nominee for Wine Educator of the Year at the Wine Enthusiast Wine Star Awards, and has appeared in Forbes, the New Yorker, and the Chicago Tribune.
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