Thanks to its bountiful landscape and complex viticulture regions, California is the country’s leading producer of wine. That’s why Skyside has planted its seeds across the state, from Napa to the Inland Valleys, so that consumers can enjoy the full spectrum of styles, flavors, and textures that California has to offer.

On this special episode of the “VinePair Podcast,” host Zach Geballe is joined by Skyside’s winemaker, Anne Dempsey. The two discuss how Dempsey got her start in the industry, the process that goes into creating each vintage of Skyside wines, and how Skyside ensures each of its vineyard partners adheres to sustainable practices.

Tune in, and learn more about Skyside at

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Zach Geballe: From Seattle, Washington I’m Zach Geballe, and this is a “VinePair Podcast” special episode. Today I have the pleasure of speaking with Anne Dempsey, who is the winemaker at Skyside. Anne, thank you so much for your time.

Anne Dempsey: Absolutely. It’s so great to be here with you.

Z: So let’s start with a little bit of your background. I know you’re a California native, or at least a longtime California resident. But how did you get into the wine industry and then make your way to Skyside?

A: Yeah, my entry into the wine industry was a slow, long trajectory. I was born and raised in Northern California, and I’m the granddaughter of Italian immigrants, and my grandfather was actually a winemaker. How this looked in my family, so I grew up in the suburbs nowhere near wine country. But I was raised in this environment where mealtime was almost a ceremony, and it was something that no matter what, we stopped and we were just present and talked about our days and talked about the food and wine at the table. That was my upbringing. I always loved science and the outdoors, so when I went to college I said, “How can I do something that weaves all these things together?” I took an introduction to winemaking class at UC Davis, and it was automatic. All of a sudden it was like art, science, and history — all these different attributes of what we all know and love about wine. And it just clicked and it made sense, and I literally jumped in and never looked back.

Z: Very cool. Then what brought you to this Skyside?

A: Yeah, I joined Skyside for a specific reason. Beforehand, I had worked in Napa and Sonoma, I’ve worked in New Zealand and South Africa. What I kept coming back to with wine is I spent a lot of time learning about quality, different AVAs in different areas. What speaks to me with wine is how it really forms a sense of community where, when I think about wine, I think about enjoying it with my friends or family and over a meal, and that is something that was really true to Skyside. So I love that about it. Additionally, I really liked working with AVAs like the North Coast and larger AVAs to really play with cooler- and warmer-climate fruit and things like that. So that’s what brought me to Skyside.

Z: Gotcha. So there’s something as a winemaker about being able to have, as you would describe it, a broader palette to work with when you are working with some of these slightly larger areas. As you said, warmer and cooler spots within it that you’re getting a broader input than someone working with a single vineyard or even a smaller sub-AVA might. Does that ring true?

A: Exactly. But I had to learn it on a smaller scale to really understand it because I’m the type of person where I have to touch the vines, see it, and feel the wind. So I spent a long time with estate vineyards and a smaller AVA. Once I really understood how Mother Nature shifts and the kinds of adaptations you need to make with just experiencing harvest and making wine, that’s when all of a sudden it got really exciting to expand out and to really think about picking this particular flavor profile of a warm climate, so I’m going to choose to work with some Lake County Cab. But I’d also like the structure and the coolness and the floral aromatics of the cooler climate. So I’m going to pick this vineyard in Mendocino, and that’s how I think about it with Skyside.

Z: Let’s talk a little bit about Skyside. Maybe you can walk us through its origins, and then how you and the team see it today.

A: Yeah, absolutely. It started really organically as a small offering. It was something that we wanted to play with, using different vineyards and thinking about ways to create balanced wines that were different from what they were making under the broader portfolio. And it hit very clearly and very quickly. It was a wine that resonated with a lot of people, and it quickly expanded year after year. And so in 2017, Skyside officially became its own brand, which is when I came on board. What we’re trying to do is really identify and create balanced wines that really showcase the vineyard characteristics. Wines that go great with food, and really find unique vineyards. Since July, I’ve driven 10,000 miles just to go visit vineyards and find these great fruit sources. There are phenomenal vineyards all over the place. So it’s really exploration and trying to bring home something that people feel really confident in sharing with their friends and taking them with them to barbecues and enjoying on Friendsgiving, things like that.

Z: Well, and that actually raises a really interesting question that I would love your thoughts on. We’ve talked to lots and lots of winemakers on the podcast over the years, and it’s always interesting to do so. I think that winemakers like you who have this, a specific approach to winemaking where you’re looking at blending as being a critical component in what you do. I’m always fascinated with winemakers who really do that. I mean, all winemakers blend to some extent, but I think some would lean into it more than others or talk about it more. So what is your blending process like? How do you take these raw inputs, this unassembled wine, and put it together?

A: Blending is something that takes years because it starts with an idea. For example, right now I’m thinking about what I want the 2022 vintage to look like, and it doesn’t exist yet. The vines are there, they’re doing their thing, but I can’t touch it. I can’t feel it. So it starts with this idea of coupling cooler- and warmer-climate vineyards together to build structure and characteristics and layers and then comes into play in reality, in the cellar. I’m starting to think about it the second I have grapes to taste. Because of the idea that what you form and what Mother Nature presents you with sometimes are two different things. So I have the general goal in mind, and then I figure out how to take each of these small components and bring them together to make the wine that I’m trying to make.

Z: I see.

A: So it’s really years, and then when it comes to it, it’s tasting monthly. Let’s say I have 10 lots on the table and eight of them make perfect sense for the vision. And then two of them, I need to work with them to get them in line. That’s how it’s working. Then the final blending of “OK this is it” happens about four months in advance of bottling, and then I try to bring a group of people together around the table to taste. That way there are multiple palates and it’s not just one person. I think it helps capture different people’s likes. What will happen is we go back and forth with 20 percent of this and 30 percent of that and add it all up. And there’s always this moment with blending where it just clicks where everybody’s like, “Yes, that’s the one.” And that’s what we try to search for.

Z: Very cool. And I’m wondering, you talked about how it’s important to you that the wines be versatile and that they pair well with food, and I certainly understand that. Is it challenging in blending or conceiving of these wines? I would imagine that there’s a significant percentage of people who drink Skyside wines who drink them in the way that Americans drink lots of wines. They drink them at 3 o’clock on a Saturday afternoon, they drink them at 10 p.m. on a Tuesday night watching TV. You can’t dictate to your customers too much what they do with your wine nor would you want to. So you have to create a wine that fits all those use cases and more. Is that challenging, or does that come naturally?

A: Yeah, it’s both of those things. Yes, it’s challenging. It’s important to really understand who is drinking the wine and what they want from it. There is somebody who will buy it and save it for 10 years, there’s somebody who will buy it and drink it that night. I have to think about that, and I want to think about that because I know myself, I like wines that really give me something to think about that helps me enjoy my food. But every time I smell and taste, I’m getting a little bit of something new out of it, and that’s what I like in wine. So I try to really bring that together. So it can be challenging, yes. But I’m thinking about it from the very beginning. So I make sure that when blending, there are components in there that will help it age. There are components in there that will help it shine right from the get-go. And that kind of helps the wine evolve over time and meet different people’s needs.

Z: Absolutely. So let’s talk a little bit about some of the specific wines that you guys make. Starting on the white side with the Chardonnay. Chardonnay in California can be hard to generalize because there’s a lot of different approaches. If you were to consider the ideal Skyside Chardonnay, what are people experiencing with that one?

A: I want to showcase Chardonnay, and I want to share a piece of what I see from the vineyard on through. I want the Chardonnay to be something where you can really taste the characteristics of the vineyard. You’re seeing florals, fruit characteristics, citrus, and stone fruit. But I also want to use oak as a nuance. So it’s another layer. So if you imagine the tapas of wine, where what’s fun about tapas is you get to play with lots of flavors. That’s what I try to do with the wine. So it’s more acid-driven. I only put a portion through malolactic fermentation because I like really bright, citrus acid-driven wines. But it’s elegant and soft and really something that you can easily enjoy with lots of different food.

Z: As far as red blends, this is a category that I find to be really fascinating, in part because it’s so open to interpretation. What people are expecting, what a winemaker thinks a red blend should taste like. For people who maybe haven’t tried it before, what should they expect going into the Skyside red blend?

A: Well, I personally am a huge, huge, huge fan of Merlot, and I love medium-bodied wines. To me, our Skyside red blend is really my ode to Merlot. So I use both cooler and warm climates Merlot as my core. If you imagine yourself cooking a chicken tonight, you use this core of Merlot. Then I use the other blenders as ways to help the Merlot shine. The blenders will shift year to year, but it’s really trying to capture that medium-bodied red wine. There is structure, but it’s in a nice, velvet way. I like wines that are completely dry, that don’t have sugar, and that really showcase what the vineyard gives us.

Z: How are you getting to that velvety texture? Is that through barrel aging? Is that through the ripeness of the fruit? Because I think that that descriptor is something that a lot of people do like in wine, but they may not understand how a wine they like gets there.

A: Yeah, absolutely. It’s a lot of things. It’s picking the varietals that I work with. So for example, a hint of Malbec gives you a nice, really soft texture in your mouth when you just take your first sip. A lot of it comes from how you actually work with the grapes themselves. I like to use a really hands-off, guided approach to pump-over. So it’s helping the grapes to get the flavor and extraction when the skins are in contact with the wine in the tank. And as the winemaker, you get to dictate how much extraction you get from it. So you can get a big, bold wine. You can go really soft and take off the skins early and get something more approachable. I like a little bit longer time on skins because I feel like the wine finds its balance in this really nice place. So it’s fermented through, mostly dry, and still on skins. Then the wine has this tipping point, where all of a sudden, you can see the wine that it’s going to be, where it stops smelling and tasting like a fermentation and it really tastes more like a finished wine. And then I wait a couple of days because that’s right when the mid-palate starts to develop. It’s almost like it’s marinating. That’s what I call it with the cellar team, and they laugh every time. Just having the contact there is really building the wine.

Z: So speaking of texture, tannin, structure and all that. The third wine that you got that you make is a Cabernet Sauvignon. And obviously, people have their own sets of preferences and opinions when it comes to Cabernet Sauvignon, as they do with most things. But for you what defines your style? And again, what can people having a bottle of Skyside expect?

A: Yeah, I think what defines my style is a soft approach that showcases power in an elegant way. Cabernet is a powerful, strong grape. For me, sometimes I think it’s so strong it’s hard to appreciate. I really try to showcase the fruit characteristics and give it a softer style. I think it surprises a lot of people. It’s more fruit-driven and uses oak to help enhance the aromas. But it’s also balanced and in a softer way. So it’s lower on the alcohol spectrum, below 15 percent ABV. A lot of California Cabernets have a lot of alcohol. I think there’s a lot of people out there that shy away a little bit from Cabernet, and this is one that I think can speak to a wider audience.

Z: I believe it’s not out yet, but coming soon is a Pinot Noir. And Pinot Noir is not only a new variety for you through Skyside, but is also coming from a different part of California. Can you talk a little about the Pinot Noir, what people can look for in that, and then what, if anything, is different about working with fruit from the Central Coast as opposed to the North Coast?

A: I’m very excited about this wine. It’s fun to see it finally come out and ready to share with people. We knew we wanted a Pinot Noir, and we were looking at what we wanted to do with that. And our thought at Skyside is that California is an amazing place. There are so many different areas that can grow phenomenal grapes. And so we wanted to take Skyside on the road and explore a new region. We really thought that the Central Coast showcased similar characteristics. There’s the ocean influence, there’s lots of different elevations, there are different soil types, and there’s a way to show complexity and lots of layers like I was talking about before, just in a different way. So that was our goal with this Pinot Noir. So I want it to be something you can see the floral aromatics, the fruit it’s got, it’s nice and soft and silky. It’s got the tannin and structure to hang, but is definitely very approachable from the get-go.

Z: Gotcha. When it comes to a unifying thing about all the wines at Skyside, I know sustainability is also a big part of that. Sustainability is a word that we certainly hear a lot about, understandably and rightly. Maybe first you can talk about for you and for Skyside, what defines sustainability when you’re looking at vineyards and winemaking more broadly?

A: Yeah, at Skyside sustainability is something that can be really confusing. For us, it’s a very personal decision. You have to ask yourself as somebody who’s using the land and producing wine, “How can I help make sure that all these resources are here for the future?” And that was how we started. So when we looked at the different options that we had available, we realized what we wanted to do is make sure that we only partner with vineyards that are certified sustainable. Because we work in such a wide array of regions and we have everything from elevations of 1,000 feet to valley floors to next to rivers. We have a lot of different types of individual areas that our vineyards are in. So we wanted to create something that we felt each vineyard owner could maximize their particular situation. As of our 2019 vintage, all of our grapes are 100 percent certified sustainable, and we accept a couple of different ones. For example, fish-friendly farming, we accept the organic certification. We accept Lodi rules. All of these certifications have one thing in common: that they ask the vineyard to consciously use inputs to manage them carefully so that you really care for the longevity of your land. We also like the word sustainable because it’s not just land, it’s people. A lot of these certifications really require that you’re taking care of the people that work there, too, and that’s super important.

Z: Yeah, absolutely. I think that’s a really good point. It’s something we try to talk about a lot in the podcast is that element of sustainability that encompasses not just farming, but also how the people and the broader community are treated in the winemaking process. As we move towards the end of the conversation here, I have a couple more questions that I wanted to get to. The first is, we talked a little bit about this idea of crafting a wine that can be broadly appealing in a lot of different circumstances to a lot of different kinds of wine drinkers. You also talked about knowing your consumer. How do you get to know your wine drinkers? What is that process like? Because it might be the case for some wineries and some winemakers that they hear directly from the people who buy their wine. That may be the case for you as well. I’m just curious, how do you get that kind of feedback and information about people who are drinking your wines?

A: I get out there. In our pre-Covid life, I traveled quite a bit to different markets anywhere from New York to Florida to Japan and really talked to people about wines. For me, it’s asking questions. What do you like? What do your customers like if you’re at a restaurant? What are people asking for and paying attention to? And then doing the very humbling thing of presenting your wine in a blind lineup and asking groups of experts, “What does this wine look like and how does it show?” And it’s a constant effort. If you think about it as a winemaker, I’m operating in the future of what people are going to see. So I have to really keep tabs on what’s resonating with the vintage that we have released so that I can make sure to honor that and the vintage that I’m making now.

Z: My last question is, for people who are interested in these wines, what are the best ways to go out and find them?

A: Yes, these wines are available at You can use Drizly, they’re available at Target, and certain grocery stores in your area depending on where you live, but those are good places to start.

Z: It must be pretty cool to walk into Target and be like, that’s my wine. That is not, after all, what most winemakers get.

A: Yeah, I actually really love it. For me, Target is a place where there’s a lot of things you need there, and it’s exciting to see how much good wine there is at Target. Like, there’s a lot of great stuff there.

Z: Yeah, I got to admit, I haven’t done a lot of wine shopping at Target. But I have two kids, so there’s a lot of Target trips in my life, as it turns out.

A: Take a look.

Z: Next time I will, for sure.

A: When I’m there, I may realign the labels.

Z: Yeah, you gotta face those bottles. All right. Well, thank you so much. I really appreciate the time and learning a little more about Skyside, and I look forward to giving the Pinot Noir a try when it comes out and just seeing what you guys do years into the future.

A: Absolutely. And I just wanted to mention one quick thing. From October to December this year, we are participating in supporting the James Beard Foundation’s Open for Good initiative, and this is something we thought was really important at Skyside. Restaurants are a huge part of our business and it’s our community, and we wanted to do something that supports them getting back on their feet after everything they’ve been through. So a portion of the proceeds for purchases of Skyside from October to December of this year will go to this Open for Good initiative.

Z: We’ll make sure to include a link to that in the show description as well. Anne, thank you so much for your time. I really apprectiate it and look forward to chatting with you down the road.

A: All right. Thank you so much.

Thanks so much for listening to the “VinePair Podcast.” If you love this show as much as we love making it, please leave us a rating or review on iTunes, Spotify, Stitcher or wherever it is you get your podcasts. It really helps everyone else discover the show.

Now, for the credits, VinePair is produced and recorded in New York City and Seattle, Washington, by myself and Zach Geballe, who does all the editing and loves to get the credit. Also, I would love to give a special shout-out to my VinePair co-founder, Josh Malin, for helping make all this possible and also to Keith Beavers, VinePair’s tastings director, who is additionally a producer on the show. I also want to, of course, thank every other member of the VinePair team who are instrumental in all of the ideas that go into making the show every week. Thanks so much for listening, and we’ll see you again.

Ed. note: This episode has been edited for length and clarity.