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Rising Stars: Meet Riki Olson of Twin Cities/Twin Ports

Today we’d like to introduce you to Riki Olson.

Hi Riki, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Absolutely! My journey in music has been a winding one, shaped by many influences and experiences. I was actually born in Sweden and moved all over the United States growing up. I didn’t start playing live until we landed in Chicago, where at about 13 years old, I joined the Hix Bros All Stars, a blues, rock, and jazz touring band that really jump-started my love for performing. Later, I found myself in LA working as an audio engineer apprentice at a music studio and playing in various groups, including a grunge-punk band called Hobart W Fink and an R&B soul band called Skyler Reed Project. All that experience on the road and in the studio has given me a ton of insight into how to shape a band’s sound and live presence—skills I now bring to Squid City Slingers.

Sydney (Squid) started playing fiddle when she was just 5 years old, and Chris has been playing guitar since he was 7. We all ended up in Mankato, MN, playing in different groups. Chris and I actually met through the music program at Minnesota State University and formed a progressive alt-rock band called The Only. One night at Moonshiners in Mankato, we played a show alongside Organ Child (featuring Sydney on fiddle), and everything just clicked.

After COVID-19, both of our bands fell apart, but instead of giving up, we decided to merge our talents and start fresh. With Sydney’s experience and passion for bluegrass, folk, and jazz at the helm, we launched Squid City Slingers—a high-energy trio blending bluegrass, folk, country, and jazz. Our mix of heartfelt originals and handpicked covers delivers foot-stomping energy, rich harmonies, and a unique sound that resonates with audiences across the Midwest.

Based in Minnesota, we’ve built a strong following in the Twin Cities and Twin Ports, playing renowned venues like Bent Paddle, Earth Rider, Broken Clock, Gunflint Tavern, and Mankato Brewery. We’ve also hit some major milestones, like headlining Bluegrass on the Black Festival and SquidFest, playing the MN Musician Showcase at Mall of America, and even opening for one of North Dakota’s biggest folk groups, MoonCats, who have been instrumental in helping us break into the ND scene. This year, we’re expanding into Wisconsin, Iowa, and North Dakota, with shows at Rhythm of the River Bluegrass Festival, Bayfield Apple Fest, Copper Trail Brewing Oletober Fest, Rock Bend Folk Festival, Kota Ray Dam Music Festival, and River Falls’ Bluegrass Bourbon & Brews Festival.

Beyond festivals, we also play private events and weddings, and we’ve got a packed 2025 schedule already lined up. We’re incredibly excited about our upcoming EP, “Harbors & Highways,” recorded at Library Recording Studio in Minneapolis and set to drop in Summer 2025. Our first two singles, “Feed My Fire” and “Like A Dog,” are already out and getting a great response.

On the personal side, Sydney and I are officially moving to Duluth this July, while Chris is staying in the Twin Cities. This move will actually help us logistically, letting us stay with each other when we’re playing in either area and making it easier to tour. All of these experiences—touring, recording, and building a band from the ground up—have taught me a lot about the music business and what it takes to create a successful act, and I’m proud to bring all of that to Squid City Slingers

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It definitely hasn’t been a smooth road, but I think those bumps along the way have taught us a lot. Like any band, we’ve faced plenty of challenges: keeping a group together, balancing work and personal lives, and dealing with the financial realities of trying to build a business in the music industry. COVID-19 was a huge disruption too—it completely derailed both of our previous bands, and there was a lot of uncertainty about whether we’d even have opportunities to play live music again.

When we formed Squid City Slingers, it wasn’t easy to get our name out there. We had to start from scratch—booking our own shows, handling promotion, managing our own finances—and that’s a lot of hats to wear as independent musicians, but we’ve found ways to make it work.

We’ve also had to navigate the business side of music—setting up an LLC, handling taxes, learning how to work with independent contractors, and figuring out all the paperwork that comes with running a legitimate business. It’s a ton of work, but it’s also incredibly rewarding to see the progress we’ve made together.

Through it all, our passion for the music—and for sharing it with people—has kept us going. Those tough times have taught us how to be more resourceful, to trust each other, and to keep moving forward, no matter what.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
Our work with Squid City Slingers is all about sharing our love of music with the world through high-energy live performances, rich harmonies, and a dynamic mix of styles. We’re a trio that blends bluegrass, folk, country, and jazz, and I think that genre-bending approach is one of the things that really sets us apart. We pride ourselves on creating an experience that feels both authentic and exciting—whether we’re playing a packed brewery or a big festival stage.

We specialize in heartfelt originals alongside handpicked covers that we put our own spin on, always aiming for that foot-stomping energy and connection with the audience. We’re known for our driving stand-up bass, fiery fiddle solos, and flat-picking guitar—each of us brings years of experience to the table, and I think that shows in our sound.

One thing I’m especially proud of is how we’ve built our following from the ground up. We’ve gone from playing local gigs to headlining festivals like Bluegrass on the Black and SquidFest, and we’ve been featured on WTIP North Shore Radio, Pioneer 90.1 radio, Mankato Free Press articles, and a KEYC News Kato Living TV appearance. That growth means a lot to us—it shows that people connect with what we’re doing.

What sets us apart, though, is our genuine love for the music and the joy we bring to every performance. Sydney’s fiddle playing drives the trio with passion and precision, Chris’s guitar work brings depth and groove, and my background in audio engineering and years of live touring experience help us create a polished, dynamic sound. We’ve each lived in different places and played in different bands, and all those influences come together in Squid City Slingers. At the end of the day, we’re not just another folk band—we’re a group that brings together all those musical threads to create something that’s truly our own.

Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
Absolutely! We’ve had a lot of help getting Squid City Slingers off the ground, and I’m so grateful for the people who’ve supported us along the way. One of the first people who comes to mind is Professor Steve Dalager from Duluth, MN. He plays bass in a local group called Climes music. Not only did he offer us a place to stay when we were getting our feet wet up there, but he also woke up early to cook us breakfast multiple times—those mornings turned into meaningful conversations and bonding over music and shared interests that really helped shape our direction.

Another key supporter has been Adam Hildebrandt, the banjo player for Bark Point. Adam has been a guiding force when it comes to our marketing strategies and getting connected with new venues. His insights and connections have helped us expand our reach significantly.

Tim Leutgeb, the banjo player for Black River Revue and guitarist for Tres Osos, has been instrumental in helping us grow in the northern Midwest. He’s helped us navigate the Duluth music scene and beyond, opening doors we might not have found on our own.

The booking agent for MoonCats, Scott Balliet, has also played a big role, helping us land some of our biggest shows in North Dakota and introducing us to that music scene. We’re also grateful to Aleksander Glauvitz, the owner of Coffee Break Entertainment, for his support in the Twin Cities. His efforts have helped us land some great gigs and connect with a broader audience.

It really does take a village, and these folks have been invaluable to our journey. We wouldn’t be where we are today without their kindness, generosity, and guidance

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