Meet Sydney “Squid” Wojszynski

We caught up with the brilliant and insightful Sydney “Squid” Wojszynski a few weeks ago and have shared our conversation below.

Sydney “Squid”, we’re thrilled to have you sharing your thoughts and lessons with our community. So, for folks who are at a stage in their life or career where they are trying to be more resilient, can you share where you get your resilience from?

I think a lot of my resilience comes from how I grew up. I’m the second oldest in a family with five kids, and we moved around quite a bit trying to make things work in rural southern Minnesota. Both of my parents worked, and money was often tight, so everyone had to pitch in. A lot of times, that meant I had to step into a “second mom” role—helping with meals, household chores, and making sure my younger siblings were taken care of.

That kind of responsibility at a young age teaches you grit pretty quickly. You learn how to adapt, how to make do with less, and how to take care of yourself and the people around you. There wasn’t a lot of room for quitting or feeling sorry for yourself—you just did what needed to be done.

Through all of that, music was always the constant. It was the thing that brought our family together when everything else felt uncertain. Playing music wasn’t just an activity—it was comfort, connection, and stability. I think that’s why I still lean on it so heavily today. It reminds me where I come from and why I keep going, even when things get hard.

That upbringing shaped not just how I play music, but how I live. It taught me resilience, humility, and the value of showing up—for your family, your community, and the people you love.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I’m Sydney “Squid” Wojszynski, and I’m the fiddle player in Squid City Slingers—a high-energy trio blending bluegrass, folk, country, and gypsy jazz. Music has been part of my life basically forever: I started on violin when I was five, and I grew up in a family where music wasn’t just a hobby, it was how we bonded. My grandpa used to play for nursing homes and would have the grandkids accompany him on whatever instruments we could manage. That’s where I learned how powerful live music can be—how it can connect people instantly, even in the simplest settings.

Professionally, my main focus right now is building Squid City Slingers into a band that can travel, grow, and keep creating music that feels honest. What’s most exciting to me is that we don’t live in one genre. We’ll hit a driving bluegrass groove, then slip into a jazzier swing feel, then land on something more folksy and emotional—and it still feels like us. I love the storytelling part of it, and I love the energy exchange with an audience when you can tell they’re really in it with you.

Right now, we’ve got a lot of music in the making. We recently recorded an EP with MN Songwriter Sanctuary, and it’s currently being mixed and mastered—so we’re in that exciting phase where the songs are really starting to come to life. On top of that, we’re planning to head to Boulder, Colorado this winter to record a full-length album, which feels like a huge next step for us.

We’ve also had some really meaningful milestones lately—like our recent performance on PBS Backroads—and we’ve been expanding our reach beyond Minnesota into surrounding states while continuing to play festivals, breweries, weddings, community events, and corporate gigs. It’s been amazing to see our music connecting in so many different spaces.

At the end of the day, we’re just trying to keep writing, keep growing, and keep putting on live shows that feel joyful and real—because that’s what got me into music in the first place.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

A lot of it comes down to grit—just showing up anyway. I learned pretty early that you don’t always get to wait until you feel ready or inspired. If you want something to grow, you have to keep putting time into it, even when it’s messy or you’re tired. The people who last aren’t always the most naturally talented, they’re the ones who stay consistent. For anyone early on, I’d say build routine over motivation. Do the small work over and over and let it stack up.

The second thing is listening—like really listening. The best music happens when nobody’s trying to be the main character the whole time. In a band, it’s all about paying attention, locking in, leaving space, and reacting to each other in real time. That’s what makes it feel alive. If you want to get better at that, record your rehearsals and listen back honestly. Play simpler than you think you need to. Try to serve the song instead of your ego.

And the third thing is learning how to take it seriously without killing the joy. I love the art side, obviously—but the practical stuff matters a lot too. Riki handles most of the business side for us—booking, emails, logistics, all the behind-the-scenes things that keep the wheels turning. And honestly, that’s been huge for our growth. Now we’re also starting to work with promoters and booking agents, which feels like a big step, because it’s going to give us even more space to focus on what we do best: writing songs, tightening the live show, and making the music as good as it can be. It’s not the glamorous part, but learning how to build a team around you is what makes it possible to keep doing the part you love.

What is the number one obstacle or challenge you are currently facing and what are you doing to try to resolve or overcome this challenge?

Right now, the biggest obstacle is finding a consistent extra player who’s willing to actually commit and travel with us. The core trio is solid—me, Riki, and Chris are locked in—but finding a really strong mandolin or banjo player who can rehearse, tour, and record with us has been an ongoing struggle. We’ve had some awesome sit-ins who can jump in here and there, and we’re grateful for them, but having someone who’s truly “in it” with us full-time feels like the missing piece for the next step.

In the meantime we’ve just been making it work. Riki’s been learning mandolin and Chris has been learning banjo so we can still get the sounds we want in the studio when we need to. And we’ve also had a lot of help from people in our scene—huge shoutout to Adam Hildebrandt for recording banjo on both Harbors & Highways and our MN Songwriter Sanctuary EP. That support has mattered a lot.

The other challenge is just pushing into that next level as an emerging band. We’ve made huge strides lately, and it finally feels like we have the building blocks: more content, stronger connections, booking agents and promoters, and big appearances like NPR’s Great American Folk Show and PBS’s Backroads. We already have festivals booked for 2026, including Sioux River Folk Festival in South Dakota, and we’re starting to expand into Wyoming and Colorado, plus we’ll be headlining Custer Beacon’s Winter Festival. It feels like things keep opening up, and we’re just trying to stay ready for it and keep saying yes when the right opportunities show up.

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