Work Redux #034: Community Wines

July 9, 2025

Community Wines is a Toronto-based collective that blends a passion for natural wine with a love for music and community. Founded during the early days of the pandemic by friends Matt Stein and Blake Pearson, it began as a grassroots effort to make low-intervention wines more accessible by splitting wholesale cases among friends. Over time, it evolved into a vibrant event series known for its open-air block parties featuring curated wine selections, local food vendors, and live music.

I understand that you both met while Matt was DJing. What was the occasion, and how did that go?

⎯⎯⎯ Matt: We had two friends who were throwing a party at Fizz, which Mikey Apples opened. Now it's a vegan restaurant or something like that, but many moons ago, I think in 2020, it was kind of a Hi-Fi natural wine bar before there were many in the city. We had friends that were hosting a party there. It was just as COVID was coming in. There originally was a title to the party that was ‘XYZ’, but once we found out everything was going to get shut down the following week, they changed the title to ‘Party of the Year’. Blake: Genius marketing. Matt: I was DJing it. Blake was having a lot of fun. He was watching a boxing match on his phone, and he came behind the booth while I was trying to mix records for the second time ever, and he kept trying to convince me to watch this boxing game with him. I kept telling him to bug off because I don't care about boxing. Blake: My excuse is that the bar was right beside the booth. So I was ordering wine, having a good time, nudging him over. I wasn't harassing him like a groupie behind the booth. Matt: I felt harassed. But yeah, his charm came through. We ended up chatting. And we just started talking about natural wine. I think that bar was one of the first places in the city that really had a strong offering, and Blake and I were super into it at the time. We kind of became fast friends, and the seeds of Community Wines started.

So Matt, you were already into music and DJing, but Blake, were you more into wine, or did those things happen simultaneously?

⎯⎯⎯ Blake: I think the reason we got along so well is because we both were into them equally. Music is such a big part of our lives, and we bond a lot over it. But at that time, we were both getting into natural wine and really excited about it. It was a perfect blend of the two. Matt: When I first moved to Toronto, I didn't know a ton of people. I would just hang out at the record store, Invisible City, and a lot of the stuff I like and got into was because of Gary and Invisible City. Blake comes from the music side at a totally different angle. Like, super into rock and hardcore and stuff like that. But we both have a strong shared appreciation for music, especially live music and parties.

It was bad timing that you two met at the eve of the pandemic when really there were no parties. People weren't going out anymore. So, did that shift to Community Wines happen naturally? If everyone's inside doing their own thing, drinking wine makes a lot of sense.

⎯⎯⎯ Matt: Totally. I mean, everything's a bubble, right? Like, natural wine is still very present. It's a growing category, whatever, but I feel like during COVID was like the peak natural wine bubble. Exactly, like you said, people were home. They weren't spending money going out to the bars. They had a little bit more disposable income— Blake: They were making sourdough. Matt: Exactly. Blake: We were drinking wine. Matt: The original orientation was not parties at all. It was actually just like, you could go to a super nice restaurant and get a great bottle of natural wine, but it's going to cost you $120 because there's a restaurant markup on it. There were fewer bottle shops at that time in the city, and a lot of them were still fairly expensive. The little secret is you can just go to the wholesaler or the importer and buy directly from them, but those guys are like big fish. So they don't sell bottles. They only sell cases. So Blake and I had the idea to be like, we could just buy the case and then sell them to our friends on a per-bottle basis and create a little markup. Terrible business, but I have fond memories of people coming to do pickups wearing masks. I think that personal approach, for lack of a better word, kind of seeded the original community and allowed us to get a following before we started with the parties.

That's a great segue into the parties themselves. There's been quite a few now, but I guess the first one was at East Room.

⎯⎯⎯ Blake: That's right. That's where it all started. I actually remember seeing the parking lot at an evening event on Carroll St. We were having drinks, and we pretty much harassed them that night to let us have that parking lot to do a party. They had no idea who we were, but they somehow committed on the spot, and that kind of sparked the whole thing. One of the problems that we faced a lot with Community Wines is that there's not that much outdoor space in Toronto to throw parties because everything gets built on. There's condos being put up nonstop. There are some abandoned industrial areas, but you gotta go pretty far, and people don't wanna trek. So it's not the same as New York, for example, where they have so many spaces to do this. So anyway, we saw that one at East Room and we were like, this is gold, and it kind of kicked it off.

Did you feel like you're getting in over your head in a certain way?

⎯⎯⎯ Matt: I feel like everyone who is an entrepreneur and starts a business ends up realizing very quickly that no one has any idea what they're doing, and you kind of just gotta put it into the universe and then figure it out. I had done some charity events like bar nights and stuff in university, but never any logistical planning, AV, bar setup, nothing. It was uncharted territory for us.

Did that give you the green light? Like, you're not just doing pickups for natural wine to masked patrons, you now have something to build on.

⎯⎯⎯ Blake: Yeah, I think so. I look back, and during the actual moment, I was just really enjoying the party and trying to get more people in because there were so many restrictions with COVID. All I could think about was, how do we move more of these people in the door, and how do we get it going? Looking back the next day, it was like, oh shit, that was a lot of fun. It was the blend of the two things we love so much: music and wine. I just thought, why don't we take this even further now? I guess it was always in our minds, and we always shot the shit about it, but that kind of sealed the deal.

Can you describe not only what the parties look like, but what your mission is when you are putting one on?

⎯⎯⎯ Matt: It's always been inspired by that open-air, European, Mr. Sunday party feel. Like Blake said, the infrastructure in the city sucks so much, and the city is so hard on people, that something that feels authentic is pretty difficult unless it's in a real club setting. The idea has always just been to find unique spaces where you wouldn't think it makes sense to throw a party and convert that into a space where people are really excited to come together. I feel like our pillars have always been, well, a) the music obviously. We spend way more money than we have to on very legit sound systems, and we try to bring in music which is fairly accessible and fun for everyone, but also heady and into record culture if people appreciate that. And b) is the bar, which Blake can speak to, because he's spent a lot of time working on that. Blake: For the bar, we like to bring in drinks we wanna drink, from the wine to the beer, while also making sure that the wine is curated enough that you wanna drink it outside and not feel too pretentious about it. We want something that's juicy and weird, you can drink out of a plastic cup. Matt: And we’ve tried to make food a bigger thing for us, too. Almost every party we try and pair with a really cool local business. We have Lambo’s coming up for one of our parties. With East Room, we've had Forno Cultura. Rosie's Burgers. Mac’s Pizza. You name it. We've worked with a lot of really great people in the city. I feel like our parties have always been a meeting place for people. Everyone comes out and sees each other, which is awesome. We do do some winter stuff, but it has definitely been this open-air summer feel that we've cultivated.

You’re kind of an intersection of a lot of other entrepreneurs and businesses, and doing so in an unpretentious, community-driven way. Was this intentional, or was it because of your personalities that you wanted to reach out and connect people?

⎯⎯⎯ Blake: I think we just love working with people that we genuinely fuck with; somewhere where we'd spend our money if we weren't partnering with them. I have a lot of love for Toronto, and I know a lot of people love to hate on Toronto, so I'm trying to bring it back. We see other cities doing cool stuff, and we want to bring it to Toronto, because Toronto deserves these fun outdoor parties too. Matt: Blake and I are both sales-y guys. A lot of our job is connecting people and is very relationship-focused. I don't think it's something we're conscious of, but I think that's our strong suit: meeting a lot of people, finding our tribe, and making connections. To use the Community Wines platform to do that is super cool, and we do it in a more cultural context, rather than a business context, like our day jobs. Blake: Every collaboration is genuine and thoughtful. We actually want it to be something that we truly like. We're not just gonna take it from a monetary standpoint by any means. Matt: Up until maybe this year, this has not been a profitable venture. It's been a labour of love. This is the first year where we can at least access the scale where we can start making some money, even dipping our toe into some sponsorship stuff. It was important for us to just build a really strong community, wear our hearts on our sleeves, and feel as authentic as possible. It's tough, man. To turn a parking lot into a music festival costs around 30K of fixed costs. Though a lot of people think we're killing it, we just get by on most of these parties. Now we’re afforded the opportunity to make it a business, which is awesome, but it's definitely been a labour of love so far.

Let's switch over and talk about your mix. Since these mixes are typically music to work to, did you follow that guideline, or did you just want to jam? 

⎯⎯⎯ Matt: We definitely tried to pick music that is good to listen to while working. I feel like people often use these platforms to go ham. so they can send it to other people who plug themselves. Which, you know what, if you want to make a living through DJing, you do what you've got to do. I support it. But we definitely tried to select music that was a little bit chill-er, good for lounging, hanging out, and doing work. The mix is more on the rock and jazz tip. It starts with AOR and folk stuff, and since Blake is a huge Deadhead, we worked some of that into it, which was super cool.  Blake: Some people might not say it's work music, but I say you can listen to The Dead every hour of the day.  Matt: I think we have 16 minutes of one live Grateful Dead track.

Which is like an eighth of it. 

⎯⎯⎯ Matt: I had to cut it at a certain point. But yeah, it's honestly really nice because I’m usually playing DJ music like house, balearic, and boogie, so it was nice to pull stuff that was more on the rock and jazz side of the world.  Blake: I don't DJ, but music's such a big part of both of our lives, and I had so much fun putting it into the world in this different way that maybe now I gotta step behind the booth with Matt at one of our parties.  Matt: Totally. We put this Jim Morrison song that I didn't actually know, but Blake knew called ‘Ghost Song’, which was off the posthumous album that they made, and if you're in Blake's world, you know that song, but in my world, no one really knows that song. But when I heard it, I was like, this is so heady and awesome. I think that song kind of encapsulates the spirit of the mix pretty well. 

There's often a certain methodology to putting together a mix, whether that’s research-based or intuitive, but do you think the kind of sampling and tasting you do when putting together a mix is similar to when you’re tasting and curating wines?

⎯⎯⎯ Matt: I think it is in some ways. With wine, you don't really know what you're getting into until you try it, which has some parallels to music. One thing Blake and I try to do, depending on the vibe and setting, is curate the wine to match the party. So, for example, our Bather party, the swimwear brand, is like a garden party, so everything is fun and cold and summery on the wine side. Similarly, the selectors and DJs we picked that are playing that party would tell you that a similar spirit goes into how they think about choosing music. We did a party at Cafeteria a couple of months ago during the winter, and, again, we had more interesting and complex wines. Not everything was as cold. They were darker and deeper reds. The music of that party was also selected in a similar fashion. So I think there are some interesting parallels there. I feel like in a mix, it's important to start somewhere and end somewhere. And I would say when Blake and I are going out drinking wine, you don't start with the heaviest red. You start with something light, accessible, and easygoing, and after many different glasses or bottles, you slowly get to that endpoint. I think in a mix, similarly, you have an idea of where you start and where you want to end, and everything in between is the art of it all. However, I would say the DJing, mixing, and choosing of music is probably more difficult than the consumption of wine.

Let’s talk a little bit about what you have planned for the summer.

⎯⎯⎯ Blake: We actually just dropped tickets for our first “festival” with Standard Time. It's going to be a bigger production, bigger capacity, some really fun artists like Vegyn, Fcukers, Jack J., Andre Zimmer, Raff Reza, Cal, Milch, Loukeman. It's under the Bentway, and it's going to be like a proper festival experience. Matt: We're letting it rip this summer. There's basically a party like every four weeks, including our block party with East Room in August. Blake: And then we dropped a wine. We made our own wine. It’s available at all of our parties. Really excited about it. It's a chilled Gamay. It's a really good, juicy crusher for a day party.

How did you work that out, and how do you go about planning your summer events?

⎯⎯⎯ Blake: We try to plan ahead as much as possible. This winter, we did a full mapping exercise, if you will, on how we're going to play our summer out. I think we're just really fortunate, too, where we've organically grown year over year so much and every time we do a party, we grow with that, from programming to drinks to restaurants, whatever's involved in that.  Matt: We’ve been very reactive for the last four years, and this year we were trying to be proactive. We rented out a boardroom this winter and spent a full day planning out the year. It was incredibly unnecessary, but a lot of fun. And we actually got pretty organized, which was good. We haven't spent a dollar on marketing, so it's been awesome just to see things grow organically. It’s an interesting thought experiment to think what it would look like if we did this full-time, or if we had some money to play with. Maybe it would look like shit because, you know, as soon as you try and juice every dollar out of something, it's not cool anymore, or maybe we could make it 10 times better. So I think we're going to navigate that over the next couple of years and really focus on just doing right by our community, giving them really cool experiences and keeping the original thesis and values of the party intact.

Work Redux is a collection of mixes made to be listened to while working. We work closely with local and international DJs to assemble thoughtful music that will carry members throughout their day and introduce them to new sounds. –East Room is a shared workspace company providing design-forward office solutions, authentic programming and a diverse community to established companies and enterprising freelancers. We explore art, design, music, and entrepreneurship. Visit our News & Stories page to read more.