Interview: JACK

Not the easiest artist to Google, or get a direct hit when searching on streaming platforms, JACK’s Vampire Weekend-ish, smart and witty indie pop is a buried treasure. Jack Osborn started performing with touring bands before he had a driver’s license and moved to Omaha, Nebraska a few years ago to have more access to recording resources and creative types that he felt a kinship to.

Having just turned 24, Osborn’s wrapping up his most successful year to date – from performing across the country (most of June as support for The Blue Stones; opening for Des Rocs in Nebraska; a trip to NYC to play the Mercury Lounge) to posting both music and non-music (comedy, interviews, skits) content across platforms like Instagram and TikTok to filming a number of music videos to releasing the debut JACK full-length album, Sad Songs in C Major.

With an overwhelming ambition and a drive to succeed – and the musical chops to back it up – the future should be bright for the young musician and Osborn’s got plenty of plans for his future. But, before we get to that, I was interested in going back to the beginning and discovering where the drive to create music came from.

How did this all get started?

JACK: Being around instruments growing up happened because I grew up in skate parks. My dad owned three different skate parks and if you’ve ever been around one, for some reason, there’s always kind of a drum set set up in the corner and somebody’s bringing in a guitar. Music and skate culture have always gone together.

So I grew up skating in the park and playing instruments with the guys hanging out after the park closed. That’s where I first got my hands on a guitar. Growing up, music teachers recognized that I had a talent and an act for it. One of my music teachers got me into our city’s orchestra when I was 10 or 11, which was super cool. I got to tour with the orchestra, I went up and sang one song every night. That was my first intro to being on stage.

I really became a musician when I started touring. At the end of eighth grade, I started touring behind a singer who had been on The Voice doing like grinding gigs, like four- or five-hour bar gigs where we played mostly covers, slipping originals in here and there. That’s where I really became a real musician because I was forced into practice, which, when I was 14, I wasn’t going to be disciplined enough to practice that much on my own. So that was really cool.

Along the way, I also I took lessons from Ron Emory, who’s the guitar player for TSOL, the Southern Cal punk rock band. His mom happens to be from Sioux City, Iowa, where I grew up, so he moved back there to take care of her and ended up just living down the street from me. He taught me a really valuable lesson early on that it doesn’t matter how much you know, as far as theory and everything, at the end of the day, you just need to write good songs. He has a signature Fender model, and he couldn’t tell you scales. He can’t tell you the name of a note he’s playing. He’s doing it all just by feel and whether it sounds good. That’s carried with me a lot. He says that you don’t need any tools other than the guitar, piano you have, and you can write a full song right there.

How we got there to here is basically that the pandemic happened, so I couldn’t tour with the bands that I had been consistently doing the grind with. I was stuck in my home and that’s the birthplace of my project now.

Going back to the band you were touring with, you were a band member, not the front person?

JACK: I was always playing guitar or bass and then being the second singer. Lots of times, when you’re doing those long gigs, if your singer has a sick night, they need somebody you can step in and do an hour or two to take some of the load off of them.

It’s funny because that whole time I wanted to be a good singer and I wanted to be more involved in these bands. I wanted to write with them, and I was so eager but there was a lot of pushback. It was one of those situations where they didn’t really want to write with everyone else and the manager of the band at the time actually would oftentimes take me to the side and tell me, “You’re a good singer, but you’ll never be a front man,” and “You need to just focus on supporting our singer and supporting what we’ve got going on.” And he’d always tell me, “Don’t let your ego get in the way of a good thing.”

So, honestly, to this day, and it sounds petty or whatever, but I still think of when we were in Minneapolis on this tour in June, I had somebody come up and, for five minutes, they were a singer and they were praising me, just giving me a list of things that they were impressed by my stuff and, to this day, as they’re saying they’re saying this to me, I’m like, “Fuck that guy who kept telling me I couldn’t be a front man.”

When people comment on my singing, that still hits that same spot internally where I’m like, “Thank you so much. That truly means the world because for a long time, my young self was unsure if I really could be a front man or not.”

That’s crazy to me that anyone would think you don’t have the voice – or confidence – to be a front man. When you’re writing songs, is there a process? Do you start with the music and then write lyrics? Do you hear a word or phrase in your head and use that to start writing lyrics and then add music?

JACK: Every song’s a little bit different. There’s kind of a process. There’s a first go through that I think is really important. Anytime I get an idea that I feel pretty good about, I try to always write four or five verses and then two or three choruses. Way too many. And then I’ll leave it for a while and come back and pick my favorite verses, pick my favorite chorus, kind of assemble it. Then I’ll leave it for a little while, send it off to my buddy, Rick Carson, who’s my producer. We do everything together. He’ll call out the lines or words that he hates and then we’ll do another revision. When we come into the studio and we start doing vocal takes, there might be a couple last minute “Hey, this word needs to be changed or you’re saying this one’s plural and it’s not. That doesn’t make sense with the sentence.” It’s just fine-tuning things. But the biggest thing is we have so much trust to where I can send him a song and he can be like, “It’s not it, just move on, save yourself the time and move on,” which is really, really nice, because you can find yourself trying to make something work that is just never going to work. There’s nothing there, so that feedback is really helpful.

What type of recording resources do you have at your disposal?

JACK: I record at Make Believe Studio here in Omaha with Rick Carson and Rick is incredible. I cannot speak highly enough of this dude. He engineered some of the A Day to Remember records. He engineered for Terrace Martin and a bunch of other people. He worked with David Bendeth on a bunch of records. He has a beautiful, beautiful studio here in Omaha that you’d just never know it was here. He’s actually from Detroit, but he built it in Omaha because he wanted to be in a central location. Here you can get ten times the size of a room that you could get in LA or Nashville. It’s a really, really cool spot and I was just lucky to get hooked up with him when I was 18 or 19. I just cold called the studio and got a tour. I didn’t have any money, but I just wanted to take the tour and I ended up just kicking it and hanging out for a few hours that day and talking with everybody and we became really good friends. Ultimately, it led to us wanting to make music together.

You grew up in Sioux City. How did you end up in Omaha?

JACK: I graduated high school here early and I just graduated early because I wanted to tour more. I was always the youngest in the bands I was in and school was getting in the way of touring. I moved to Omaha because it’s the closest big city to me and is only a couple hours away. I knew nobody. I moved here with one friend. I just went out to shows, tried to meet people, went to open mics, just anywhere I could go to meet other arts people. It was a little harder when I was younger, because I couldn’t get into a lot of venues but luckily, after about a year here, I met the studio guys. That’s been my spot ever since.

Even moderately successful artists are having trouble making money these days. It’s got to be tough for an artist just starting out like yourself. Is this a moneymaking thing for you yet? Is that the dream or is it something you’ll do for a few years before finding something that is a more reliable income stream?

JACK: It’s definitely the dream to make all my money off of it. I make money right now. I teach lessons privately because I play all the different band instruments. I also teach some writing lessons and things like that so that really helps. As far as going out on the road, you never make money because you’re always putting the money back into the account because you’ve got to front the next tour. At the end of the day, if you come home from tour breaking even and everybody’s able to keep the jobs that they had before they left and go out again in another couple months, that’s a huge win.

We haven’t had a huge streaming win yet and, right now, I’ve been really focused on doing shows for exposure and to gain fans, real fans. Those are very different from money-making shows. If you’re going to make money, you need to be playing four-to-five hours in the back of a bar or at an event like a wedding. And you’re not really there to gain fans, you know, you’re there to be in the background. It’s a hole that I’ve slipped into myself, where you can make really good money. There are guys that make their whole income doing weddings and doing long gigs. But I wanted to make sure that we’re just doing 30-to-45 minutes sets, hitting it really hard and then going out there and talking to every single fan, trying to build that one-to-one connection. That way, instead of coming back to that city every time and playing a 5-hour show to new people who still don’t know you, you’re coming back to play another 45 minutes and hopefully the next time you’re there, you have 20 people who met you last time and shook your hand and are more like your friends than anything else.

Your name is Jack and what you’re doing is released under the name JACK. Do you consider what you’re doing a band or are you a solo artist who is responsible for writing and recording all the studio stuff and then getting some friends to play shows with you to play the stuff that you can’t in a live setting?

JACK: When we started recording the record, the only consistent person has been a drummer who’s actually never played with me live, but he’s my buddy from growing up, Max Miller. He’s actually the drummer right now for the country star Bailey Zimmerman, who’s like a big country dude. Max came up to record just because he wanted to be involved and when we were recording, we just assembled the band that day. If I want a keyboard player who sounds like this and is really good at that vibe, then we have a couple homies we’ll call. One of the coolest things about recording was the little things you get out of the people who just happened to be in the room. Like. on “Best Friend,” the coolest guitar part of the whole song was made by a guitar tech buddy of ours who was just in the room that day and he wrote it while I was singing the lyrics. He’s like, “Hey, I’ve got this part” and we threw it on there. Max put a couple guitar parts on the record and I played drums on “Big Brain.” It was very open and loose, whoever can do it right I don’t care where it comes from. I don’t need my hands on every single thing.

For going out on tour, we kind of built it backwards to where the record was done and then I built the band based on people who I’d want to sit in the car for 20 hours with, people who were real friends of mine and who would make traveling and the whole thing enjoyable. I’ve been in bands before where you don’t talk at the dinner table and you’re silent in the car and it’s not fun. I really wanted to make sure that the crew we go out with is great and the crew I have is awesome. `Right now I’m in the middle of editing a whole documentary to wrap up our last year, just trying to go in and find all the laughs and all those happy moments. And there’s a lot of them.

What were some of your favorite things about 2023?

JACK: I think I’m going to go with opening for The Blue Stones and playing a sold-out show at the Troubadour in LA with them. I’ve dreamed of that since I was 13. That was a pretty fucking cool moment.

How did you land that tour?

JACK: My buddy Tommy Hanlon is a tour and production manager. He’s done just about everything for a bunch of bands like Grandson, Elle King, and Young the Giant. We’ve been everything, like making the album, everything we’re doing is through friends and friends of friends. We made the record with a community of friends. We’re booking all the shows through friends. Me and my buddy Dan, who’s a videographer, we make all the videos and all the content. We’ve worked really hard to keep everything in house and grow this thing ourselves. So yeah, The Blue Stones tour was through a friend of a friend.

Any memorable shows?

JACK: Phoenix, Arizona was the biggest surprise of the tour, the most fun city I’ve ever played. The energy was crazy. There’s something about Phoenix that was really cool.

I’ll also slip in Austin. We were standing out front of the venue and Gary Clark Jr. just walked in front of me. We played Antones, which I’m pretty sure he’s a part owner of, and I didn’t even know it was him. I’m not looking at people like that. The guy next to me, though, was like, “Gary Clark, get over here, take a picture.” He was freaking out. I just went over and, really calmly, I was like, “I have to be honest with you, you single-handedly inspired me to play guitar.” He played my hometown in Sioux City before he really blew up. He played lat an afternoon arts festival at like one o’clock to nobody and I remember being like, “This dude is an unbelievable guitar player.” That was at the time where I was young and all I wanted to do was impress people with the guitar. I just wanted to be bad ass with the guitar. So, I’d listen to his records all the time. I know a bunch of his riffs.

As we were standing there talking, I could tell he was getting annoyed by these people who were kind of fangirling, so I said, “We have a really cool van. I know you’re into cars and stuff. If you come around back, I’d love to show you the van.” I slipped away and him and I walked around the alley and chatted for 20, 30 minutes. We had this really cool van with red sparkle paint and white walls. We took a picture in front of it and introduced him to all the guys. That was a really cool moment.

Do you consider making content for TikTok and Instagram and YouTube to be part of the job of being a musician and promoting your stuff or is it something you’d be doing even if there wasn’t any music to support?

JACK: As a kid, I made videos with my brothers that we thought were fucking funny, but weren’t. Before the record and starting to grow this thing, I was not even on social media. I had actually deleted everything. I’m super anti wasting time on that kind of stuff. I’ve never been a crazy fan person. I’ve always just loved the music, but didn’t even know the singer’s name of my favorite bands. I just listen to the music over and over but never got into the story too much.

But, I think social media is a necessary thing you have to do. I started doing it when we got three or four songs into the record, and we sent it out to see what kind of feedback we’d get. The feedback was really good. We had a bunch of management companies and a couple labels actually make us offers. We’re like, “Oh, that’s cool. That’s exciting.” And then we saw their offers and the offers were an amount of money I didn’t have, but also not like an insurmountable amount of money. We realized that the terms on these deals are going to be so terrible until you can actually bring fans to the table and bring your own little community to them. That’s when I really started getting into creating content. I redownloaded the apps, made my usernames universal, and then started posting every day.

I’d say for anyone out there making music, just start doing it now because it’s probably going to take you a year or two to get comfortable with it and for it to not interfere with your creative side. There’s only so many hours in a day and when you pick up something like that, now you have an hour of shooting and at least a couple hours editing added to your daily schedule and it’s really easy for that to compete and get in the way of your writing time and other creative endeavors.

But now, I’m really thankful we’ve been hard at it because it’s starting to meld to where we just are the content. We’re doing cool things, we’re filming it, and we’re not having to think quite as much. The ideas come more naturally, it’s not as like forced. With December and January being down months for touring, I’ve been a lot more creative and we’ve been making a bunch of music lately.

Have you had anything go viral?

JACK: We’ve had a couple things. I did a cover of “Suicidal Thoughts” by Biggie Smalls. And that opening line is just like made for virality, it’s so in your face. I also was poking the bear a little bit. There’s all these people who were like, “He’s just taking Biggie’s lyrics” and I’m like, “It’s a cover song. I’m not claiming they’re mine.” Then I started tagging those people and being like, “I’m the new Biggie.” They’d be so mad. You could see that it was getting sent to like hundreds of people because people were like sending it to their homes, being like, “Fuck this fucking kid who thinks he’s going to be Biggie.” So that went off a bit.

We’ve had a couple comedy things and funny interviews go off which has been a weird space to be in because I just I want to do music. Anytime I’m doing stuff like that, I’m just trying to rope them in and bring them back to the music.

The album is currently only available on streaming services. You don’t have any physical product and you’re not on Bandcamp so the only money you’re earning from the album is through streaming royalties. Is that the only way you’re making money from your album?

JACK: We did a direct-to-vinyl session when we were in New York last time. Those are limited and they already sold out. Whoever bought them left their name and a special message and we did live takes of whatever song they wanted us to play. That was the first physical thing we’ve done. I want to do vinyl. There were a couple things that were holding us up this year. Number one, our old van, we literally had packed every fucking inch. There was no room for a box of vinyl whatsoever. Now we have a little bit more room so that excuse is gone. We need to get on it, we need to make some. I have a ton of people reach out and ask about it.

What led you to cover the Captain and Tennille’s “Love Will Keep Us Together,” Meredith Brook’s “Bitch” and Biggie Smalls’ “Suicidal Thoughts”?

JACK: With “Bitch,” I thought it was cool singing it from a male perspective because no guy is willing to say, “I’m a bitch.” Every guy wants to be tough, so I feel like that line hits so hard from a dude. It’s saying, “I don’t fucking care. I’m a bitch. I’m a lover. I’m all the things you want me to be.”

I’ve always loved “Suicidal Thoughts.” It’s such a sick story. A lot of people stray away from that song because it’s so vulgar. He literally says, “I know my mom wished she had a fucking abortion” and he talks about sucking his mom’s boobs which nobody wants to hear. The whole preface of the song is that at the beginning, he calls, you hear the phone ring, and Puff Daddy picks up. Biggie’s having a meltdown. He’s having some kind of moment. It’s an honest representation and he’s saying things you truly would in that moment that you normally wouldn’t say otherwise. To me, it’s like a great movie scene. It’s like when a guy grabs a woman by the wrist and it’s uncomfortable and it’s real and raw.

“Love Will Keep Us Together” was a hit in its day and I thought it was cool because it was a cover. I thought it would be cool to cover a cover of a hit song. It was just the vibe. We had our friend Eddie Moore in town that day who’s an amazing jazz piano player from Kansas City and we wanted to make something with him. He’s one of the only people I know that would nail that arrangement and that piano part.

One of the more recent covers we did was “Patches” by Clarence Carter. Chef Porter happened to be in town, and he was making a hip-hop record. We were having a really good time, and we were like, “We should make something together.” It just so happened that on that day, there were a couple of members of a band called Black Swan Theory in the studio. They are an amazing band, amazing players, just unreal. And Mo and Jonathan Brooks, the bass player and the keyboard player, wanted to make something so we settled on “Patches.”

What does 2024 look like for JACK?

JACK: I want to release another record. We’re working on that already. We’re about to announce a new original coming in January.

I want to do some acoustic songs, like acoustic arrangements of songs from the record, maybe in a new key with a couple of new things just to bring people back to our record.

We have a tour in February already set up with a band from Wichita named Social Cinema. They’re a really awesome indie rock band. We’re going all the way down to Louisiana and then slowly working our way up to the Midwest. And then we’re talking to people right now to try to land another big tour in hopefully in April or May June. I want to stay on the road as much as possible.

The biggest thing I we learned this year is fans who meet you at shows and shake your hand or take a picture with you are fifty times the fan of the guy who finds you online and follows you. Those people who meet you in person are so much more engaged. They’re more willing to buy sticker to support you even though they don’t really even want the sticker. They are truly there to be your friend and support you and help you get back to their city. I want to make more of those fans.

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2024 Tour Dates (so far)

2/8 – Lawrence, KS – The Bottleneck
2/9 – Kansas City, MO – Farewell Coffee & Booze
2/10 – Fayetteville, AR – Madison’s Square Garden
2/11 – Denton, TX – Andy’s Bar
2/22 – Lincoln, NE – The Bourbon Theatre
2/23 – Wichita, KS – February Freakshow Fest
2/24 – Omaha, NE – The Slowdown

*All dates with Social Cinema