22 Questions With Chicago-Born Country Singer Songwriter Dustin Olson

We’re not in Kansas anymore.

If you’re in Nashville long enough to survive the cringy karaoke covers of “Wagon Wheel,” the stumbling boot-loving tourists, chances are your Martin’s BBQ hushpuppies were served to you by an aspiring musician.

It’s the classic tale that we love to hate: the strawberry blonde girl-next-door barista who hums just quietly enough to be subtle, but loud enough to prove to passersby that she’s got pipes. Or the coy man-bun type wearing retro glasses (the world may never know if they’re prescription) that slings you your next round of drinks. We love to hate the cliché of it all, because underneath the personable waiter that’s struggling to make ends meet in pursuit of their “big break,” we just hope for stability in their lives (all of our lives, really).

But who doesn’t love a good underdog success story? 

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When it comes to bootstrapping your way into the artist life and working with your God-given talents, country rocker Dustin Olson shares his homegrown story in each track he curates. From farming alongside his dad and brothers in the Dixieland of the Midwest, to graduating with a Master’s degree in corporate banking (and owning a muscle car business to boot), it only made sense for Olson to follow his passions – and the yellow brick road – all the way to Music City.

Thanks to his faith, patience, and expansive knowledge of business, the Chicago native meets all the needs of an authentic country artist: a genuine soul with a story to tell about life, love, and belief.

We stole a moment of Olson’s time to get the lowdown on the best Chicago eateries, all things business, and naturally, his music. 

What’s the most recent song you listened to? On the way here, it was “Way Maker,” actually. It’s a Christian song.

Describe yourself in three words: Hardworking, and hardworking (laughs). Fun, and I try to be outgoing.

Favorite thing about Chicago suburbia, besides family? Chicago food is pretty good, like Portillo’s Italian Beef. There are times where I will go get Portilllo’s beef and fries before I go see my family (laughs). And Chicago pizza. They finally have a Gino’s East in Nashville, which is amazing! So food, for sure. Definitely not the weather. You gotta go to a place that’s on the north side called Chicago Pizza and Oven Grinder. It’s like a Stromboli-calzone kind of situation – pot pie, but pizza. 

You’ve done business in corporate banking and owned your own muscle car shop. Have either/both careers helped you in unexpected ways as an artist in Nashville? Oh yeah! Between that and college jobs at Best Buy, the sales side of [banking]…For this tour, I sat down and sent 2,900 emails, and cold calls, and Facebook messages. And even on the “No’s,” I’d still respond and say “Do you know anyone that might?” Then owning my own company helped with time-management, even though I kind of suck at that (laughs). And with the social media, marketing, and selling yourself – that’s the business/training side of it. So much of this industry is all business and marketing; it’s 90% that, and 10% the show.

What’s something most people don’t know about you? (Ponders.) I don’t know, I bare it all.  I try to be pretty real with everything. I just had an argument with someone about – I posted on Instagram that I got this jacket for $14 at Goodwill in Wisconsin, and they were like, “No you need to act expensive.” And I was like, “Why?” This isn’t LA, this is country music, this is rock and roll, we should be as real as it gets. Why should I go on [Instagram] and pretend this is a $400 coat?

…Oh! Friends and family know, but I don’t drink anymore. It helps me stay focused, and [drinking] wastes money. I work too hard for it.

What’s been inspiring your music lately? If you listen to my first record, it’s very country. And now it’s very pop-rock and almost pop-punk. And I think deep down, that’s what I’ve always wanted to do. Like, in the last song “What Makes Me Want You,” all I listened to was Taking Back Sunday for days. And we went into the studio and produced it, and someone was like, “Oh, look. You just made Blink-182 but with twang.” But I was like, that’s awesome! I love that.

If you could record a duet with any current artist, it’d be: I would take somebody like – it could be anybody, right? It would be cool to do it with someone, well like my heroes…so, Eric Church or Bruce Springsteen, or Kip Moore. Those guys are very much me. Or even up-and-coming artists like Tucker Beathard. I love his stuff because it’s very rock.

Least favorite question to get asked in an interview? Apologies, in advance, if I’ve asked those. I really don’t have one. I love that you’re doing it like – I get bored when it’s the same old, “What’s your hometown?” Did you not read the bio? It’s like, this is already known. I think where it’s an obvious question, well everyone’s heard that. I love it when it’s more outside-the-box thinking. So, you’re killing it. (laughs.)

Would you rather co-write with Johnny Cash or grab drinks (alcohol optional) with Elvis Presley? I would probably have a drink, if I could drink, with Elvis Presley. Either way, that’s a tough one because that’s all my dad listens to. I went back [home] last weekend and he had Elvis playing. So, Elvis; he’s like the man. To hang with Elvis would be cool, but that’s such a tough question because I love Johnny too. A co-write with Johnny-that’s legendary. Is he gonna cut it? (laughs.)

What do you do to wind down after a show? My show ritual has changed quite a bit. To get ready for a show, I used to do some shots of whisky. And now I listen to worship music and just pray, then chill and go into my show. Afterwards, I try to talk to people and just try to make friends with the audience. A lot of times, on the road solo, I’ll just drive in silence and reflect on the show. Then, pray about it again, like Thanks that this is my life. But on the road too, I go back to the hotel and either read or watch TV, so I’ve been burning through books lately. No blue screens!

How about hobbies outside of music? That’s really sad, because I don’t know if I do [have any]. (laughs). It’s hard, because Nashville’s expensive; this industry is expensive. So if I’m not playing or working on [music], I’m either driving Lyft/Uber or working at Sprocket Rocket. I’m working a lot. I just started author-writing. So a friend and I are going to go write this afternoon. She writes fiction and I’m writing a devotional for musicians and creative people. I haven’t decided where it’s going yet, but that’s a newer hobby. It used to be drag-racing and sports, but now my life is pretty central to music.

What’s been your proudest moment as a country artist so far? I have to say, Saturday night in Iowa City, was the first time that I was like, “Wow, these people are singing my songs!” Like I’ve had it in my hometown or in Nashville when friends come. But this was like, I had four people come to the show that I knew, and the rest were all random people. The fact that I was able to engage them and get them all to sing back to me was mind-blowing. I was sick all last week and my voice was gone at the start [of the show]. I said, “Hey y’all, I’m gonna give you 90 minutes of everything I’ve got, if you give me everything you’ve got. Let’s get crazy.” But they all sang along the whole time to everything: covers, my songs (they figured them out), and I got them to do call backs. And my performance, I didn’t know where I was, but when I got done I was like “Ah! Who are you?” (laughs.) So that was my happiest, I think. I’ve never walked off the stage and just been like, “Damn. You killed it.” Creatives- we’re so mopey…that’s what we do to ourselves, it’s so bad.

If you could open for any artist – dead or alive – who would it be? Eric Church. All day.

Have any crazy stories from playing around Nashville or tour life? I had one where it was me, Shelby Lee Lowe and his whole band. We were going to Wisconsin, playing in my hometown, and had stopped there. I don’t think the guys had ever been to the north before in the winter. So they’re in the van in T-shirts and shorts, we get to my dad’s house and it was polar vortexing like crazy (probably negative twenty plus thirty mile-an-hour winds), and the drummer gets out of the van, and my dad punched him in the stomach. And he just like, [imitates a deep inhale] jumps back in and is like, “How do you people live like this?” I was like “What were you expecting? It’s like the first or second week in January in Wisconsin.” (laughs.)

I probably shouldn’t say this one…I had one time where a club owner tried to stiff me on a bunch of money, and I brought up this story that Billy Joe Shaver told about Waylon putting dynamite in the back of this bar because he got stiffed. And I was like, “You know, back in the day when someone stiffed them, they’d put dynamite on the bar…lucky I didn’t bring dynamite today.” And the guy got really quiet and he went to the register and came back with more money and I was like, “Are you serious? That worked? I was just telling a story.”

One skill you wish you had? Honestly, I wish I could play lead guitar better. I skipped over the whole like, learn to do this (because I just wanted to play songs and write songs). Now when I’m doing solo stuff or with full-band, it’d be cool to be like “I got this.” Everything else I’ve wanted to do, I’ve just done it. Traveled all over. I wanted a master’s degree, I got it.

When you’re not playing shows or writing, where do you find yourself on the weekends in Music City? Working, for the most part. Sunday, usually at Cross Point [Church]. And everyone from my small group on Sunday nights, we do like family dinner because everyone’s transplants. It’s cool. Otherwise, I don’t go out on the weekends.

If you didn’t have your music, what would you be doing? Probably some kind of 9-to-5. I get tempted all the time by like, “Ooh, stability! Normal paycheck, normal weekends.” But I feel like I’d be in the industry in some aspect, using the six figures worth of pieces of paper I have hanging on my wall so I could pay them off. (laughs.)

Personality tests seem to be gaining more and more popularity lately. Are you a believer in astrological signs, the Meyers-Briggs test, or perhaps the Enneagram? If so, what are your signs and do they feel accurate? (laughs) I love this! I’ve had this discussion just recently with my small group, and they were talking about each other’s Enneagrams and I was like “I don’t know mine, and I refuse to take those tests.” My bachelor’s was Applied Sociology and I almost had a minor in Psychology, so I took so many of those tests and studied them and didn’t believe in them. Because if I know about a four and you think, “This is how I’m going to answer these questions,” you take the test and like, What do you know? You’re a 4! I might just do it for fun, but my friends already told me what I am, so you create [your personality results] for yourself. It’s all very vague; it’s entertainment I guess.

Favorite TV show? The Ranch. I actually really love The Ranch, because that’s my dad and brothers and I. We verbally beat each other up – so badly – and then everything you do is to make your family and dad proud. We grew up in the country and so much stuff they say on that or do, it’s like (laughs) we did that! 

What does your writing process look like? I’ve got a phone full of gibberish. I haven’t really tried to write by myself in a long time. It’s mostly just co-writes, but usually I’ll have half a chorus, maybe, or a whole bunch of hooks and run with that. But if I come up with an idea, I’ll go on Spotify or Apple Music and search. I won’t put out a title that’s already been placed. Nothing else will come up if you search my songs. I don’t like recycling hooks, titles, or even…you’ll see this run where it’s like, “Let’s compare a girl to being addicted to nicotine.” This has been done. Stop.

Have any pre or post-show rituals? I put promo cards on every table before a show, at every venue. I’ll leave a stack there.Definitely the worship music and prayer one – it gets rid of all anxiety. I do like a little bit of quiet, silence. I can just go out clear-headed and just fire away. After shows, I’ll look over video or listen back to see how I did and take mental notes. Like, “Don’t do that again – that was weird. Whatever you just did with your hand,” or “Crushed that one! Keep it in there.” (laughs).

Lastly, tell the folks what Dustin Olson has going on in 2020: So I’ve been in the studio – have to go back in in the next couple weeks, and have another song ready. The plan was at least four more songs this year. Then probably some videos. We’ll see. Mostly some songs, some festivals, and just [have to] keep doing what I’m doing. Playing as much as possible.

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