Anne Dowling, Ridge Street Wine and Breckenridge Cheese & Chocolate
Anne Dowling, Ridge Street Wine and Breckenridge Cheese & Chocolate

For Anne Dowling, a former member of the U.S. Ski Team, successful entrepreneurship means having the flexibility to live a life she loves. In the mornings, she carves Colorado powder and in the afternoons tends to her wine and cheese shop, Ridge Street Wine/ Breckenridge Cheese & Chocolate.

Read related article: Deciding There is Nothing Wrong With a Lifestyle Business

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ANNE DOWLING (AD): You buy a bottle of wine, you buy a little cheese, a little chocolate, you’re good to go, you don’t even need a real dinner. (laughing)

NARRATOR: (as music plays lightly in background) Welcome to The Story Exchange, featuring the stories and strategies of entrepreneurial women around the world. I’m Colleen DeBaise, host of The Story Exchange podcast, and we’ll be joined later by our co-founder, Sue Williams.
Entrepreneurship. The word alone -- to many people -- conjures up images of a startup in Silicon Valley, where the guys wear hoodies, the women are invisible, the investors are the bald guys in suits, and everyone is working 24/7 trying to make as much money as possible.
But it doesn’t have to be that way. Today, we’re going to introduce you to Anne Dowling, a former competitive skier, who runs a pair of lifestyle businesses in scenic Breckenridge, Colorado.

SOT: ...Do you guys wanna have some wine and cheese today, or…?
-- Absolutely.
-- Okay. We have a Chenin blanc right now that’s flying out the door because people love it.
-- Cheers, cheers.

NARRATOR: Anne started Ridge Street Wine in 2000 and Breckenridge Cheese and Chocolate a few years later.

AD: We’re busy enough and we have a, a really nice clientele. We open at noon and so we can ski in the morning. We can go on a hike in the morning, you know. We wanna enjoy this town, too.

NARRATOR: Now, Anne’s wine shop and her cheese and chocolate store -- combined -- make about $400,000 a year in annual revenue. So, they’re never going to be listed on the New York State Exchange. And it’s quite unlikely that Anne will ever be a billionaire (at least, not as a small business owner). But she’s perfectly OK with that. For her, entrepreneurship means being able to provide for her family -- she has an 8-year-old son -- while having the freedom to do the things she loves.
We headed to the mountain paradise of Breckenridge to talk with Anne. If you go to our website,, you can watch a video we produced, telling Anne’s complete story. Today, we’re going to share snippets of that conversation. If you’re more interested in flexibility than an 80-hour workweek, this is a story for you.

*Musical Interlude*

AD: I started competing when I was five years old, and then I focused on moguls and I made the US Ski Team and traveled with the team for six years.

NARRATOR: Anne grew up in Cape Elizabeth, Maine, but her skiing often brought her to Colorado’s powdery slopes.

AD: We always had a World Cup competition in Breckenridge. And I decided that I wanted to move to Breckenridge.

NARRATOR: In the late 1990s, after an illustrious career on the ski circuit, Anne decided to retire. After her last event in Lake Tahoe, she took a trip to Napa Valley.

AD: I just fell in love with the green, and the flowers, and, you know, and I just fell in love with the lifestyle of wine. And I just started reading everything I could about wine.

NARRATOR: She needed a job, and landed one as a sales rep for a wine distributor.

AD: The learning curve was just exponential. You really had to know what was in the wine, you know, what the grape varieties were, what the winemaking techniques were, who the winemakers were.

NARRATOR: After three years of selling wine, Anne decided to leave her job to spend the winter skiing in the French Alps. A wine shop in her favorite resort town of Chamonix caught her eye.

AD: There were just stacks and stacks of wine. No beer, no booze, and I was like, “Oh my gosh, Breckenridge could use something like this.”

NARRATOR: The idea stayed in the back of her mind when she returned home. Then, as fate would have it, she blew out her knee.

AD: So I had time to sit down and write a business plan. That happened in March and I believe I opened my shop in September of 2000.

NARRATOR: Anne needed about $50,000-dollars to open Ridge Street Wine, so she borrowed against her home, which she had bought with prize money she won while skiing. Within a year, she was making a small profit.

SOT: How are you guys?

AD: To me it was a way of connecting with the community. I wanna be that person that people come to for their wine every night and I wanna hear their story. I wanna hear what they did that day.

*Musical Interude*

NARRATOR: We’ve been sharing the story of Anne Dowling, an entrepreneur who has made lifestyle a priority as she runs her businesses.
I’m being joined now, as I often am, by Sue Williams, our resident filmmaker, who had the hard task of interviewing Anne in Breckenridge over wine, cheese and chocolate for our video profile.

SUE: Well, someone has to do it! All in the name of research….

NARRATOR: By the way, if you’ve never checked out our site, please do so -- it’s We’re a nonprofit media company and we produce articles and videos about women business owners. Welcome, Sue.

SUE: Great to be here.

NARRATOR: So I think we both were struck by Anne’s quality of life…

SUE: Absolutely. You know, Breckenridge, it -- it’s a real ski town. It’s surrounded by fabulous slopes and you feel it’s the sort of type of place where everyone seems very fit and healthy and very relaxed, and you can tell Anne spends a lot of time on the mountain with her family.

NARRATOR: That said, it hasn’t all been pie in the sky.

SUE: You’re right. There’ve definitely been some challenges, really from the start. Keep in mind, she opened Ridge Street Wine in the year 2000. Let’s listen….

AD: And I had a great first year and I was like, “Okay, I wanna continue doing this,” so I moved down to a house on Main Street and the rent had doubled. And then September 11th happened. And we went in the first year to having, you know, at that location people driving in and loading up their Suburbans and then going to their ski homes, to people not having that… kind of income anymore.

SUE: So Anne started to think about ways she could add revenue streams to her business. She began hosting wine-tasting events at her home. And of course, what goes better with wine than cheese from France…

AD: I would fly in cheeses -- I wouldn’t personally -- but I used a company called And it was really cool to choose the different cheeses and then pair them with the wines. And everyone was like, “Oh my gosh, these cheeses are extraordinary. You need to sell them.” And I was like, “No, we can’t because of liquor law.”

NARRATOR: Now this is where she got pretty clever…

SUE: Yeah, you can’t sell wine and food in the same space, according to Colorado liquor laws, so Anne figured out a “work-around.”

AD: So we had a second door in the shop and that was really all you needed. You needed to have two separate entrances. So we kind of put a little divider and then we bought a cheese case.

NARRATOR: Clever, clever.

SUE: Yeah, and then if there’s anything that goes better with wine than cheese, it’s chocolate -- so she added that, too, and named her second business “Breckenridge Cheese & Chocolate.”

SOT: What are you up to? What are you wanting today?
-- I just need some chocolate. Chocolate on the go, yes, please.
-- Okay. So we have a few different brands . . .

NARRATOR: But the two businesses essentially share the same space….

SUE: Yeah, they do. She moved into a larger space in 2007, which has an upstairs, and that’s when she decided to add a wine bar to the mix….let’s listen to our conversation about that:

AD: So we had to get a new liquor license and we started doing wines by the glass and cheese plates so people could sit down after skiing and have a cheese plate. We could have winemakers come and talk about the wines and the cheeses, and really created a, a space for that.

SUE: Is that one of the most profitable areas?

AD: It is definitely. You know, it’s what people wanna do at the end of the ski day. They’re tired, they wanna put their feet up, they wanna have a little cheese, a little wine, then maybe, you know, carry on.

SOT: Cheers, cheers!

NARRATOR: Oh. That’s what I want to do right now.

SUE: Me too.

NARRATOR: Thanks for joining us, Sue.

SUE: That’s a pleasure.

*Musical Interlude*

AD: We have a great après-ski kind of vibe here. We have live music on Wednesdays and Fridays.

NARRATOR: We’ve been talking with Anne Dowling, who makes entrepreneurship seem like a pretty nice proposition. While we told you about a few of the challenges she’s faced along the way….the bottom line is that she has successfully created a business that supports her family and active lifestyle. In fact, her husband Kenny -- whom she married in 2002 -- wound up joining the business, too.
That actually wasn’t part of the original plan…

AD: With the way the economy went we both kind of decided, “Well, one of us is gonna be a entrepreneur and the other one has to bring home the steady paycheck and have the health insurance.”

NARRATOR: So Kenny found another job -- but came back in 2007 when she expanded.

AD: It was our family business and he didn’t really wanna be working for someone else anymore.

NARRATOR: And while Anne is rather modest, her background as a professional athlete certainly gives her an ambition that many people don’t have.

AD: Competing all my life as a skier I think I learned… a certain drive to be the best. You know, I’m competitive, I guess you would say. So, you know, I wanted to be the best skier. I wanna have the best wine store.

NARRATOR: Anne told us that she’s enjoyed creating a “home base” for skiers, something she always searched for while skiing competitively. And in the future, she might consider expanding further, possibly with ski and winery tours to Europe. But for now, she’s content with the control and flexibility her small shops provide.

AD: There are a couple powder days where I would put on the door, you know… “Out skiing in this gorgeous day. I’ll be back soon.”

NARRATOR: Join us next time to hear more stories about innovative and inspirational women doing the things you’d never dream of. Or….maybe you would. This has been The Story Exchange. If you liked this podcast, please post a review on iTunes. It helps other people find the show. And visit our website at, where you’ll find news, videos and tips for women entrepreneurs. I’m Colleen DeBaise. Sound editing provided by Nusha Balyan. Production coordinator is Michelle Ciotta. Interview recorded by Sam Shinn. Executive producers are Sue Williams and Victoria Wang.