143: How to Prepare for Your Big Break Before it Surprises You: Interview with Jill & Kate

Stop me if you’ve heard this story before. An aspiring musician moves to Nashville with nothing but a dream and her guitar. She plays in dive bars to whoever will listen in hopes of being discovered and becoming a big star. We all know how the sad story usually ends. Or do we?

143: How to Prepare for Your Big Break Before it Surprises You: Interview with Jill & Kate

Imagine for a moment that you are a musician playing on a small stage at an open mic night at a Chinese restaurant. You’ve got a little medley of songs in your repertoire which includes a tune by Kelly Clarkson (the original American Idol).

Now, imagine Kelly Clarkson is actually sitting in the audience and she absolutely loves your sound so much that she invites you to sing backup vocals during her upcoming Daytona 500 performance. You go from singing in front of 50 people to over 250,000 people.

Seems like a fairytale, right? Well, that’s exactly what happened to this week’s guests on The Portfolio Life.

Listen in as Jill & Kate and I talk about their crazy story of accidentally playing at a biker bar, touring for 6 years with Kelly Clarkson, and the origin off their amazing duo.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

In this episode, Jill & Kate and I discuss:

  • What it’s like to co-write music
  • Deconstructing what it means to make it as an artist
  • Which episode of Friends captures how they discovered they should be a duo
  • Why sharing the load of creativity is a blessing
  • How they piggybacked on Kelly’s tour to play for their own fans
  • Reaching a pivot point and how they decided to walk away
  • Navigating personal and professional turbulence the first year on their own
  • The value of persistence
  • How talented artists come and go and attitude alone


  • Have a good attitude. Be humble and willing to serve.
  • Put in the work so you’re ready when your big break comes.
  • Be prepared to lose things.
  • Surround yourself with good people.
  • If you have a good attitude and you’re a good hang, if you can be low maintenance and low drama, it will take you far.

Don’t be afraid to suck. Because you will.


Tweet This


If you suddenly got a big break, would you be ready? How are you preparing to get noticed? Share in the comments.

Click here to download a free PDF of the complete interview transcript or scroll down to read it below.


If you think that you’re out of opportunities, you’re never out of opportunities. It’s just, I think, you can get a little bit worn down. Because if you’re doing it right, I think there will be a lot of almost’s and maybe’s, and there will be a lot of rejections. —Kate


[0:00:27.0] JG: Welcome to the Portfolio Life. I’m Jeff Goins, and this is a show that helps you pursue work that matters, make a difference with your art, and discover your true voice. I’m your host, and I want to help you find, develop, and live out your own creative calling so that you, too, can live a Portfolio Life.

Let’s get started.


[0:00:45.2] JG: Alright, Jill, Kate. Say hello.

[0:00:49.3] Jill: Hello.

[0:00:50.2] Kate: Hello, how’s it going?

[0:00:51.3] JG: Yeah, good to have you guys on the show.

[0:00:52.7] Jill: Thanks.

[0:00:52.9] Kate: Thanks.

[0:00:53.7] JG: I don’t have an official welcome. I say that every time, and it’s a little embarrassing.

[0:00:58.3] Jill: I think that was perfect, I think it works.

[0:01:00.5] Kate: #officialwelcome.

[0:01:01.6] JG: Alright, good times. I just want you to tell your story. We met through a mutual friend, Whitney English, a while ago. We’re both Nashvillians. I feel like after you live here, because nobody’s from here, or not very many. People aren’t from here, they’re all transplants. I feel like after you live here like seven, eight, nine years, you get to call yourself a native.

[0:01:24.8] Jill: I think so, yeah. I think seven could be the magic number.

[0:01:27.5] Kate: I like that. Let’s all start spreading that and be like, “Oh, have you been here seven years? You’re a native, you didn’t know that?” Great. They do call it a 10-year town, but it could be some other number, I don’t know.

[0:01:40.0] JG: How did you guys start playing music together?

[0:01:42.6] Jill: Yeah, we met in college, a semester abroad program, which was not abroad. It was on Martha’s Vineyard, which we’re going to call abroad for right now.

[0:01:50.3] Kate: You have to take a ferry together.

[0:01:53.3] Jill: Yeah, it’s over the seas. I, Jill, went to Gordon College in Massachusetts, and Kate was going to Biola University in LA, and we both met at this semester abroad program for music. It was called Contemporary Music Center. You study song writing, production, music industry stuff. It’s not a classical school, more just like kind of contemporary.

[0:02:15.0] Kate: It’s like a little mock music industry for three and a half months.

[0:02:18.2] JG: Cool.

[0:02:18.1] Jill: Yeah, we were randomly put as roommates there and didn’t know each other. We were assigned a co-writing assignment, and so we worked together on that, and our voices just blended and our style blended, so we formed a duo after that. That’s sort of how we got started.

[0:02:39.8] JG: How do you know? I thought I was a musician until I moved to Nashville. I had played guitar for like, eight years, and I toured with a band for a whole year, and I thought I like knew stuff, and then I moved here and I had waiters who were just schooling me and I was like, “Okay, I’m a total beginner.”

I’ve never co-written. That’s definitely a thing, lots of people do that in Nashville. Musicians get together and co-write songs and they become mega hits or not. How do you know when something is like, “I found my soulmate. I found this person who compliments my voice or my style so well.”

How did you guys both know that? Because I think that’s interesting.

[0:03:23.1] Jill: Yeah, that is funny. I mean, part of it is just like, we sort of think it’s like a divine thing that happened. That’s part of our take, and then we’re big Friends fans, like the TV show.

[0:03:35.2] JG: Part — one part God, is that what you’re telling me, another part Ross and Rachel?

[0:03:39.6] Jill: Totally. More like Joey because when we tell this story that when Joey finds his identical hand man in Vegas, that’s how it was when we found our identical voice twin.

[0:03:51.9] Kate: I think it was just something too, like when we perform, we write this song, and it was the first song we’d ever written together. It was not that great, looking back. We’re like, “Wow, we’ve come a long way.” It was one of those things where when we performed it, people were kind of taken aback. They were kind of like, “Wait, you guys aren’t related? Why does it sound like your voices go together in that type of sibling harmony?”

It was easy enough, like it clicked enough that we were like, why not? At least for the semester, let’s keep working as a duo. Our professors were like, “Yeah, you guys don’t have to be solo artists. You can turn in,” we had to turn in like three masters and stuff like that. We just — every one of them was like a Jill and Kate product, instead of just a Jill Pickering

[0:04:33.1] Jill: I think, too, we were young enough to go, “Yeah, we could totally do this.” That helps a lot, you know?

[0:04:39.8] JG: There is a naiveté to it?

[0:04:40.6] Jill: Yeah, there is, for sure.

[0:04:41.3] Kate: Absolutely.

[0:04:43.6] JG: You guys are in a room, writing a song together, I don’t mean to like — I want to deconstruct this. You play the last C chord or something, and then like you look at each other and you go, “This feels good.” I mean, how did you acknowledge that this was — this worked?

[0:05:02.1] Kate: That’s a good question, I don’t think people have asked us in this detail. It’s kind of fun to think back. I don’t think we actually knew until people told us.

[0:05:10.6] Jill: Yeah, I think you’re right.

[0:05:13.0] Kate: Yeah, when we performed, like we thought like, “Hey, we wrote a cool catchy song. We got homework done,” but then when we performed it, I think people were so — wait a minute, you guys are on to something. At that time, you know, this was 13 years ago, there were a lot of trios, there were a lot of solo artists, but there weren’t a lot of duos.

There were a few, but not anything that was just like — you know, it’s all Beyoncé, or the Dixie Chicks, or like Britney Spears or Madonna. Solo artists, and we just were kind of like, “Yeah, a duo thing. That might be interesting. Why not? Yeah.”

[0:05:48.1] JG: That’s cool. You guys play this song, what was the song called?

[0:05:54.0] Jill: Stained.

[0:05:55.3] Kate: Stained, like, so dark of us.

[0:05:56.9] JG: Without the E?

[0:05:57.7] Jill: A pop acoustic duo. Not with a band thing, but like, you know, we were in our very dark days. I’m just kidding.

[0:06:06.8] JG: Lots of eye shadow or something?

[0:06:08.2] Kate: Yeah, we had another one right then called She Said.

[0:06:13.3] Jill: I think that was the big one that we wrote.

[0:06:15.8] Kate: Yeah, I think it was called Stained.

[0:06:16.9] JG: You wrote this song, it wasn’t that good, you obviously don’t play it anymore, apparently.

[0:06:22.5] Kate: Nope.

[0:06:25.1] JG: Burned that bridge.

[0:06:25.2] Jill: Most songs are not that good, which I think a songwriter should admit. I think you’re lucky if you get a good one out of 50 or a hundred, I think. That’s become normal for us. We’re used to writing really crappy songs, and every once in a while, you might get a decent one.

[0:06:39.9] JG: You wrote this crappy song, and you performed it as part of this assignment, and then people dug it and they came up to you and said this is like this is the next big thing? What did they say?

[0:06:55.9] Jill: I think they just said like things like, “We have never heard people harmonize like that, that are strangers,” basically. That was mostly what people pinpointed in us is our harmonies.

[0:07:08.0] Kate: I think there was that hey, there isn’t this happening a lot in the pop music world. The Indigo Girls, they were obviously like, laying the groundwork. Kind of a different genre than we — they’re way more folk than kind of we were going, but it just — it kind of seems like there is maybe an opportunity for a duo. I think that along with people going, “Wow, we’ve never heard that before.”

[0:07:36.1] Jill: I think it was appealing to work with someone else. I think creatively, if you find someone who you can work with, whatever that means, an editor or whatever it is, a producer. I think it’s easier or for me. I’m not — this is Jill, and I’m not super-driven in business, and like at all. Like an artist. I think to have someone to do it with was really appealing to me.

[0:08:05.5] Kate: To share the workload, to share — once we left, our professors were like, “Try and play 10 gigs this summer,” and we were like, “Okay.” I mean, we were so just green and just willing to do anything, playing anywhere, and so…

[0:08:22.9] Jill: When you have a few people, it’s easier to do something together, you know? It was a little less intimidating, because it felt like if we were going to fail, at least you were failing with another person in the boat with you than just like, all on your own, and yeah.

[0:08:37.5] JG: you guys play this song. People told you they never heard anything like that. I don’t know, if you had an opportunity like, you could be like the heavy metal version of Indigo Girls. I’m just going to proceed with this interview under the assumption that you guys were a Staind cover band.

[0:08:57.6] Kate: I like it.

[0:08:58.1] JG: It’s Been a While, like that was our big break is what I’m trying to say is. They played acoustic songs. Power chords, it’s all about the power chords.

[0:09:08.6] Jill: It is about the power chords.

[0:09:11.8] JG: The assignment, after that, you guys just kept writing songs together, because nobody said you had to do this solo thing, and then after that semester was over, was it an assignment or was it just a recommendation like go play 10 gigs?

[0:09:25.6] Kate: It definitely wasn’t an assignment. The semester is over, and so everyone goes back to their respective schools. We did a spring semester, so we had a summer in between. Our two professors at the time, Warren Pettit, Tom Willet, they were like, we just asked, “We really want to do this, what should we do next?”

There’s so many things that you could do, and we had a year left of college, and they were just like, “Play. Try and get experience under your belt. Do whatever you can to just be on the stage, whether you’re getting paid or not. Just get out there.” We were like, “Okay, let’s do it, let’s go.”

We played — that summer was hysterical, because we played like open mics where you get to play like two songs, and you’re there for like six hours sitting through everyone else’s set, and then one time it was actually our 10th show that we were really trying to play. We’re like, “Let’s do it,” we had to look up in the paper, because there was like not — I don’t know, gigs weren’t listed online.

We looked up in a paper and saw that there was an open mic at this place called Uncle Buck’s Rock and Roll Grill. It was somewhere outside Chicago. We went, there was like no windows on the place, it was actually a front door that was just placed at the entrance. We walk in, there’s all bikers in leather, like that’s it, and we were like, “Hi, two blond girls, we’re here for your open mic.”

They made us, when we got up to do our songs, they made us wear a hat that said “fresh meat,” because they had a butchery in the back and they said, “No, we make all of our first timers wear this trucker hat that says fresh meat on it.”

[0:11:12.4] JG: That’s hilarious.

[0:11:14.1] Kate: Anyway, we just played and tried to get as much experience under our belts.

[0:11:21.0] JG: Okay, you did this for how long before it became like, the professional thing? Are you guys still in college at this point?

[0:11:32.6] Jill: We had one more year to finish. We thought about — we got this tiny little bit of interest in us from a manager in Nashville, and we were like, we kind of got big heads about it, but we were like, “Maybe we could do it, maybe we could” — we were like, “Maybe we won’t go back to finish school,” because we had our senior year, and my dad was like, “No, that’s not an option,” which I’m super thankful for. My parents, thankfully, helped me pay for college, and they were like, “You’re going to finish.”

[0:12:03.1] Kate: It was good, because it kind of gave us one more year to be going to school which you know, we were kind of like, let’s just get this done, but also it let us continue writing. We were writing songs for our first record that we were going to record post school. It kind of was like a nice in between before launching full time into this is what we’re chasing after.

[0:12:23.9] Jill: Yeah. We finished senior year, Kate transferred to Gordon, and we played shows all through our senior year, and wrote all the time, and so I guess it was professional once we — I guess left college, and we worked in kitchens and nannied, and stuff like that.

[0:12:44.9] JG: Cool. Okay, then what happened after you graduated?

[0:12:49.5] Jill: We went back to the music program. They had a program called Artisan Residence for alumni. You could work in the kitchen, and live and do whatever you wanted, using all the facilities, so you had full access to their recording equipment, their studio, their rehearsal space. We went back and we recorded our album, our very first one called East Coast Bound, and we pretty much did that all of ourselves.

We would just hit the record button, we would track for each other one at a time, and brought players in there and did all of that, and so by the end of the semester, we worked in the kitchen, we were Sous chefs.

[0:13:27.1] Jill: Barely.

[0:13:27.5] Kate: Barely. Yeah, we did that, recorded our first album.

[0:13:31.2] Jill: Yeah, we toured a little bit like on our own and then we decided we would move to LA, which was kind of a ballsy decision of us. We just felt like that’s where we felt like we wanted to go.

We moved to LA with very little money, I don’t even know how much, and this was like a year I guess or so after we graduated from college. Maybe two. Yeah, moved to LA and didn’t have a place to live, didn’t have jobs.

[0:13:56.0] Kate: We did have a place to live, until it fell through. We drove from New Hampshire, from Jill’s house, to — we were driving to LA. Literally, all across the country, and in Chicago, we stopped, because that’s where my parents were living, and we got a call there that the apartment that we’re going to be renting or whatever, it fell through. We were like, “Great, we have one day before we arrive, or two days before we arrive in LA, and we don’t have anywhere to live.”

[0:14:18.5] JG: Wow.

[0:14:19.7] Jill: Yeah.

[0:14:20.8] JG: What did you do when you got to LA?

[0:14:24.0] Jill: We had an old friend, or not that old, but a friend that lived there, and she had a condo and had like an extra room. She was like, “You can rent out this extra room from me,” so we shared that room. I mean, we kind of had to take whatever we could get. We shared that room, and the bathroom. It was in west Hollywood. It was actually a nice little place. It was just a little cramped, but good. We started just booking shows and we started getting…

[0:14:49.2] Kate: Odd jobs?

[0:14:52.1] Jill: Yeah, odd jobs.

[0:14:55.1] JG: Did you start playing shows in LA? How did that go?

[0:14:59.0] Kate: We pitched our Staind cover band, and people really got on board.

[0:15:03.4] Jill: LA loves Stained.

[0:15:04.3] JG: Okay, alright, If somebody’s listening to this, they’re going to go, “Oh my gosh, this is for real. I’m going to go check them out.”

[0:15:11.4] Kate: We’re not a Staind cover band!

[0:15:14.6] Jill: We knew some people out there, and we did a lot of cold calling as well, and we finally booked a show for, I think it was in October, it might have been November. It was like two months into us living there, and this is like the part of the story that kind of gets crazy, and people are like, “What?” We did this little show at this place called Genghis Cohen, and…

[0:15:34.8] Kate: Which is half Chinese restaurant, half music venue. Like you literally like, walk in, it’s like fried rice to the left, live music to the right. It’s hysterical.

[0:15:42.3] JG: I wish we had one of those in Nashville.

[0:15:44.1] Jill: Yeah, they should. That was our first show in LA, and Kelly Clarkson ended up coming to that show with some of her friends. I mean, we had been affiliated, we heard our manager, our old manager had worked in her management firm, so we had met her in a meet and greet once, but we didn’t really know her.

She heard we were playing and came to the show. That was like kind of like, “Oh my gosh!” We kind of were freaking out. We actually did a cover of one of her songs in a medley, and we found out she was in the audience, and I was like, “We’re not doing her song tonight, if she’s here,” and Kate was like, “No, we’re absolutely doing it.” We had this huge fight backstage…

[0:16:28.5] Kate: It was not huge. It was not a fight.

[0:16:29.7] Jill: It was just a disagreement. I was like, “We’re not covering her song when she’s in the audience.” I was so embarrassed.

[0:16:35.3] Kate: My thing was like, I knew that that medley went over well with our audiences, and I was like, “No, we just need to stick to the plan, I don’t want to change it.”

[0:16:42.1] Jill: So Kate was right on that one, because we sang that, and like a week or two later, we saw her somewhere and she was like, “Hey, when you guys sang my song the other night, I was like, ‘Wow, they sound like kind of like my background vocals.’ Would you guys want to sing backgrounds for me on this show I have coming up?”

We were like, “Yeah!” Our dream was like, it would be awesome if maybe we could open for her one time or something like that. When she asked us to sing backup, we were like, it just came out of nowhere. We weren’t backup singers, you know?

[0:17:15.2] Kate: We never thought about singing backup. We never — most people I think had that kind of somewhere in their heads. We did not. It was like, “Yes, absolutely, we want to do that.” Pause. “Do we know how to do it?” It was like, “Yes, we’ll do it,” and then we left and we were like, “Do we know how? What does that look like? We’ll figure it out. Yes.”

[0:17:35.2] Jill: That was sort of, that was our first show we played in LA.

[0:17:39.0] JG: That was your first show?

[0:17:39.9] Jill: That was our first show.

[0:17:40.6] JG: Kelly Clarkson was there?

[0:17:41.7] Jill: Yes. You know, that sort of — yeah, what do you do with that? When people ask us, “So I want to be a backup singer,” and they’re like, “How would you recommend doing it?” I’m like, “I have no idea.”

[0:17:55.9] JG: Well it’s easy. You just play one show in LA and you’re set.

[0:17:58.2] Jill: Yeah, just move to LA and just play a show, and it’s like — it’s sometimes hard to tell kind of our story in that way, because it’s so that sort of dream thing. The one in a million chance. We recognize that and are super appreciative of that, not that — even that being said, though, we had put in time and work and all of that stuff. It was our first show in LA.

[0:18:25.2] Kate: I think it’s just, I mean, it is kind of, everyone gets into this business or gets their break or something in a very different way. There is no cookie cutter formula. For us, we had no idea it would be playing a show in LA, and then that we would be backup singers, and at that one show, it was for the Daytona 500, we went from playing in like coffee shops to like 30 to 50 people, maybe a hundred…

[0:18:50.1] Jill: If you were lucky.

[0:18:50.9] Kate: Yeah. I think the biggest crowd we’d ever played for was like a hundred people, to our first show with Kelly, there was 250,000 people.

[0:18:59.5] JG: This is at Daytona?

[0:19:00.4] Kate: Yeah, Daytona 500. That just — the whole, I mean, everything about it was just like eye opening, mind blowing, just what is happening. That one show turned into six years of touring with her. One show turned into a tour, and then another tour, and then another tour, and…

[0:19:21.3] JG: Let’s break that down. You guys play this show in LA, Kelly’s there, you play her song, you sing it better than she does.

[0:19:29.2] Jill: I don’t know about that.

[0:19:31.9] JG: Then what happens after that? They approach you and say, “Would you be interested in singing backup?” Help me understand how that exchange went?

[0:19:38.4] Kate: Yeah, we saw her after — on the actual night of the show, she was super complimentary, loved it, you know, that was it. We were just pumped that she came and that she liked it. Two weeks later, we were at a friend’s comedy show, or like a mutual friend’s comedy show that we didn’t even know she was going to be there, but she was, and then after the show — it’s funny, Jill and I weren’t standing together, which is odd, because we’re together a lot, but she found us each individually and just said, “Hey, I have this one show coming up,” I think this was in December of 2006, and it was — she was like, “I have this one off show coming up in February, would you be interested in singing backup?”

We were kind of like, I was by myself, and I was like, “Yeah, that would be awesome!” And apparently, Jill’s response was the same. It wasn’t like her people asked us, Kelly asked us, standing in I don’t know, it was like a bar, a restaurant connected to this comedy bar. After that, that was in December. In January, like we had three weeks of rehearsals, it was three songs.

[0:20:44.8] Jill: We got a call from her tour manager and her music director…

[0:20:46.8] Kate: They were like, “This is what we’re going to pay you, this is how rehearsals work. Do you guys have in ears? This is giving all of your travel information, this is when we’re flying, this is the schedule once we get to Florida,” all that stuff, and we’re just kind of like wow.

I, at the time, was a personal assistant to a man in LA, and I was already planning in December, I was planning on quitting my job January first anyway, because this gentleman was not very nice to me and would yell at me all the time. I was like, “That’s great, I’ll just quit, do this Kelly gig, and then get a new job afterwards.”

Did you quit your job? What was your?

[0:21:29.3] Jill: I did, yeah. I got someone to replace me for the time being, which he ended up a permanent replacement. We didn’t know if it was going to be — it was sort of like an audition in a way I think. That first show.

[0:21:42.9] Kate: Her musical director is like pretty much in charge of the band, and he normally does like auditions and stuff. I think it was a little… he was a little taken aback when she just hired us. He’s kind of like, “Who are these girls?” I think those three weeks of rehearsals before the Daytona 500 were our kind of permanent audition, and it was terrifying. I look back at those three weeks and man, we worked so hard because it was just — I mean, we’re learning all these new songs, we’re learning what it’s like to be a backup singer, and just how much work goes into it and yeah, it was crazy.

[0:22:20.1] JG: Wow. You see her in the show, she asked you to come tour with her, well, just do this one show, which happened to be Daytona, and then afterwards, they just want to continue doing that. How many shows in between that LA, the first show in LA and Daytona did you play?

[0:22:40.3] Jill: I think we had one or two more.

[0:22:42.5] JG: Not many?

[0:22:42.9] Jill: No.

[0:22:44.1] Kate: I mean, also because we didn’t have time. Beginning of December or something first couple of weeks of December is when she asked and rehearsal started, I want to say the first week of January, second week of January maybe, and then it was three weeks of rehearsals, and then Daytona 500 is like early February?

[0:23:00.5] Jill: I remember having at least one other show in LA, but I think probably too, before Christmas.

[0:23:06.3] JG: How long had you been playing together at this point as a duo?

[0:23:11.1] Jill: Three…

[0:23:11.1] Kate: Four years, almost four. Yeah.

[0:23:13.5] JG: Were you guys freaking out?

[0:23:16.7] Jill: Yeah.

[0:23:16.6] Kate: Yeah.

[0:23:19.8] Jill: We had no chill.

[0:23:22.3] JG: You’re like, “I got this. 250,000 people. I kind of assumed I’d be playing Daytona anyway, so happy to do it for you, Kelly.”

[0:23:28.9] Kate: Right.

[0:23:30.1] Jill: Yeah. We were thrown into it for sure.

[0:23:31.5] Kate: The best — a funny story about that is that most events like that that are on such a big scale, that are filmed, that have to be exactly clocked correctly, there’s all sorts of different moving parts, because we were performing out on the track area, and so it was like they had to bring audience members in.

There were people packed around the stage, but get them out really fast before the race started. On most of these types of events, as we’ve since learned, they do a pretty detailed dress rehearsal run through the day before. Well, Kelly hadn’t flown in yet, and they were like, “Okay, we need somebody to do a stand in. We need somebody to be Kelly’s stand in.”

They were like, “Jill, you, come on.” Again, we were so new to all of this. They bring in like fans and we do the whole thing, and Kelly was coming up in like a truss elevator type thing, her little box was like rising. The whole production starts, and the fans were like screaming. They’re so excited, and like, up pops Jill, and she’s having to sing like all of Kelly’s parts, and she nailed it. Then people were like, chanting “Jill” at the end. It was hysterical.

[0:24:45.7] Jill: I don’t remember that, but — I remember that happening, but the chanting I don’t remember.

[0:24:49.4] Kate: People were so…

[0:24:52.4] Jill: I was reluctant.

Click here to download a free PDF of the complete interview transcript or scroll down to continue reading it below.

[0:24:54.1] JG: You two are with Kelly for six years, and was it like — you finished the first tour and they said, “Do you want to do another tour?” What was that like?

[0:25:02.8] Jill: I can’t remember if it was just assumed at that point, I don’t remember.

[0:25:06.1] Kate: Well, I feel like it’s never… I remember that was always a little nervous, because there was never any guarantee that you would automatically be called for the next tour. So I think there was a little bit of trepidation of like, “I hope I get asked for the next tour,” but it would work in record cycles. So our first album that we toured with her was her My December record, and we started with promo, and it’s flying back and forth between New York, LA, doing all of the talk shows, morning shows, and the UK and Australia, actually. We did all of those, and then you do a tour for the record, and if the record is successful, sometimes there will be a couple of tours. So it’s generally through each record cycle.

[0:25:51.9] Jill: Yeah, and the good thing is we always knew. We were never really even — and I don’t want to say this, but we didn’t want to be backup singers, in that we weren’t pursuing that. So we were at this time still pursuing our own music, recording albums, putting up videos, like the whole entire time, and Kelly knew that, too. That was our main goal the whole time. So while we were busy with her, we still were building this other thing that we had started before that.

[0:26:22.0] JG: And did working with her bring visibility to the brand of Jill and Kate?

[0:26:27.8] Kate: Yeah, it definitely did.

[0:26:28.7] Jill: Yeah.

[0:26:29.5] JG: Because I mean, you’re a backup singer, and so I could see how that might not happen.

[0:26:32.9] Jill: Yeah, I don’t think in some camps it might happen, and in some it might not. Kelly, her fans are really loyal, and she spoke highly of us on her social media, in her interviews or whatever, and so that was really helpful. If she likes I don’t know…

[0:26:51.2] Kate: Chocolate ice cream.

[0:26:52.3] Jill: Chocolate ice cream, her fans like chocolate ice cream. So having her support definitely gave us some visibility there.

[0:26:59.6] Kate: And we would book shows, like if her schedule, if her touring schedule is show day, off day, show day, off day, if we were in cities that we knew we had fans, we would try and book a show on the evening of our off day. So we would a lot of times do New York, Boston, Chicago, LA, Nashville, that type of thing, and it was great. She was supportive, our show in Chicago, she sold merch for us.

[0:27:25.1] JG: Wow, that’s cool.

[0:27:27.0] Kate: It was our most successful merch night ever, because everybody’s like, “Heck yeah, I will buy your t-shirt! I don’t even care who you are, but Kelly is going to sell it to me, yep!” So yeah, it was definitely — I don’t think that’s the norm in every camp. Some don’t allow their band members to pursue their own thing. So Kelly was never like them.

[0:27:45.9] JG: So you were playing some shows while you were touring with her when you had off days.

[0:27:51.8] Kate: Yeah.

[0:27:51.8] JG: Yeah, okay cool. How much?

[0:27:55.1] Jill: It depended. I mean, we would do the major cities mostly. So if she’s on a 30-day tour, we might do five of our own shows on that tour kind of a thing. Maybe more, but we also did Stageit shows, which is like an online concert platform, so we would do shows.

[0:28:11.8] Kate: It didn’t really make sense for us to play, if we were in Pocatello, Idaho, to be like, “Hey…” especially at that point, social media was just getting started. We were just starting to blog. I think we did our first blog in 2008, at the end or something. I feel like all of that was slowly building.

[0:28:33.1] Jill: And it was really exhausting to sing her set every night and have another show. So we worked it in, and we did recording, a couple of the guys in the band produced some stuff for us. When we were off the road, we’d work on albums and stuff.

[0:28:47.9] JG: Somebody from Pocatello right now is a little bit miffed.

[0:28:50.6] Jill: They’re super miffed.

[0:28:51.8] Kate: Pocatello, Idaho is my go to city. When I name cities, it’s always Pocatello, Idaho. I thought I made it up, but it’s not. It’s a real place.

[0:28:59.7] JG: Yeah. So you don’t tour with Kelly anymore, you’re doing your own thing, you were doing it for a while. Tell me about how that ended, and how you transitioned into this third phase of your career.

[0:29:14.8] Jill: Yeah, the last year that we toured with her, we were gone like 300 days out of the year. It was just an insane tour schedule, and I mean super fun, but just we were never home. We were working on recording our own first album that we really felt that it was a product of us living in Nashville, learning and absorbing everything that we had here.

Anyway, it was our first album that we really were pouring into, and we were having to record in 24-hour spans when we were home. Just getting home, dropping off our stuff, going into the studio anytime we could, and we just realized, if we were really going to try and do anything with our own music, we couldn’t keep being out on the road and being gone so much.

Also, for the last two and a half years that we sang with her, I, Kate was her personal assistant, started doing assisting stuff for Kelly. So on top of just singing her show, doing our Jill and Kate stuff, I was also her personal assistant, which just meant another realm of being available 24/7, having to do extra flights and stuff with her.

Even when we weren’t touring, I would have to travel with her if she had any meetings or anything like that, and again, it was all so fun. We just realized that we can’t keep up with this anymore.

[0:30:37.8] Jill: And after it was eight or nine years of us doing Jill and Kate stuff, and we’re like if we keep doing this Kelly stuff full time, we don’t do Jill and Kate stuff full-time. The reality of it was it was getting about 20% of our time, I would say.

[0:30:54.0] Kate: Yeah.

[0:30:55.0] JG: So when was that?

[0:30:56.0] Kate: That was — 2012 was our last show with her. The end of 2012.

[0:31:00.0] JG: And then what happened after that?

[0:31:02.1] Kate: Well, we had a lot that happened after that. We had a manager in place that was a friend of ours, Will Grey, and he was going to take us that first year and try to get us a bigger manager, and some bigger deals and stuff like that, and 10 days after our last show with Kelly, he was diagnosed with cancer at 33. He passed away eight or nine months later in July. So that first year, personally and professionally, was a huge like, “Whoa, what is happening in life?”

We had this new album that came out in September, and then we finished with Kelly in October, and we were pushing this whole thing, and it went to a full stop to help take care of Will and be in LA with him, and also professionally, he obviously couldn’t keep managing us, really. So we were just floating like, “What are we doing right now?” It was a hard realization for us, because he had known us since the day that we met each other.

That Alumni and Residence program that we went back and did, he was that when we were students. So he has known us since the beginning, and he actually helped coordinate in some form or fashion every single album that we had released, and so he was our everything. Our go to. He was just brilliant, and so when he got sick and couldn’t do anything anymore, we obviously didn’t want him to, but on a professional sense, we were like, “We don’t know how to do anything.” We knew how to do some stuff, but really, we were like, “We don’t really know how to do a whole lot of anything.”

[0:32:39.6] Jill: Yeah, so we were losing our friend in a personal way, and then our career was spinning, because we haven’t adjusted to what that looked like. The first year was tumultuous, I would say, and just getting our feet on the ground and going, “Okay, what are we doing again as Jill and Kate?”

[0:33:01.7] Kate: It was a whole lot of trying stuff, stuff that we had never had the time to do before. We went to the UK and played, we went twice and played shows and did a little tour over there, and that’s something that we had been wanting to do for years, because we toured over there so much with Kelly that we had a pretty loyal fan base over there. So we got to tour the UK, we did a house show tour. We did several of them here in the US, where fans would throw a show in their backyard or in their living room, and we would show up and play for an hour in their living room.

Just stuff that we’d never really had the time to do. We just tried everything to see what was going to stick, to see what worked, to see what we liked, what we didn’t like. It was just a whole new arena for us.

[0:33:49.4] JG: Wow, so tell me about how things are going now. What’s the past season been like? What are you excited about? What are you struggling with? That sort of thing.

[0:34:01.4] Jill: Yeah, right now it’s up and down, I guess, for us. We have a really supportive fan base. It’s small, but it’s really loyal. I don’t know, it’s such a weird time for us. We’ve done some other backup singing that came at us just to pay bills, and we were trying to tour, but it’s hard to tour. It’s a different industry. Money is the thorn in our side a lot of times, because we could do a really great tour in the UK, but it costs so much to get over there, we can’t make it financially. We can’t make it a success.

So I don’t know, right now it’s an interesting time. We’re trying to figure out what being an independent artist, 13 years in, with this totally new layout of what being that means. I don’t know, we’re trying to figure out what that looks like every day. Sometimes it’s great, and sometimes it’s really crappy.

[0:35:02.0] Kate: Yeah, and I think that there’s not a whole lot of consistency to it. We’re constantly trying to not reinvent, but just trying to come up with things that are going to work, that are going make money and not kill our souls. That are going to let people connect with our music, and us still get paid for it. With streaming services and stuff like that, it’s hard to make a sale, a transaction based off of something that somebody could get for free.

[0:35:29.6] Jill: Yeah, I hate hearing myself say that money is the reason we aren’t doing stuff, but it’s the reality of it.

[0:35:35.6] Kate: And it’s the business side of the brand Jill and Kate, and I think it’s hard, because I think something that I’ve been thinking about a lot is the almost’s and the maybe’s. I feel like there are so many opportunities. If you think that you are out of opportunities, you’re never out of opportunities. I think you can get a little bit worn down, because if you are doing it right, I think there will be a lot of almost and maybes, and there will be a lot of rejections.

We just heard Hoda Kotb speak, she’s the Today Show fourth hour news anchor, and she was talking about how she got rejected 27 times in the span of 10 days, just driving around from news station to news station, and they would watch part of her tape and just be like, “You’re not good enough. Go try somewhere else.” She was like, “I was used to hearing that. I just kept trying,” and on like a last-ditch effort somewhere in Mississippi, some guy watched her whole 30 minute tape and said, “I like what I see,” and she got the job.

[0:36:38.2] Jill: I think it’s that persistence, that’s where we are right now in our career. The persistence. Some days we have it and some days we don’t, to be honest.

[0:36:48.8] Kate: I think it’s hard, because we feel like we have the material. We feel like we have everything in our arsenal and our tool box that we’ve been collecting. We’ve collected tools from watching how Kelly runs her camp, all the things we’ve learned over the past 13 years, and we feel like we’re ready for some next step or a different platform, but it’s a lot of almosts and maybes until the right one hits. I don’t know if we’ve hit our next right one yet, but it’s knocking on a lot of doors.

[0:37:22.8] Jill: Yeah.

[0:37:23.7] JG: So let’s deconstruct what it means to make it as a musician. You guys are being very humble. The reality is you’re making it, and maybe that will be a different story next week. That’s the nature of the business that you’re in, and we all get that, but you have made it for 13 years. You’ve done the thing that is a dream or a side gig for so many people, and you’ve done it. So yeah, and I get that.

We all want to get to the next level, and that’s cool, but I think there’s lots of people listening who are going, “But how do I get there?” So I’d love to wrap up with a few practical things. I want to begin with a question of your break, like getting the big break. You’ve been very transparent, and, “Look, we didn’t know Kelly was going to be there. We didn’t orchestrate this, and we don’t know how you do that.” How important is a break like that, and you guys had been playing music for three or four years before that, so it was lucky, but what kind of work goes into that sort of thing, whether it’s before or after?

I mean, there was something that Kelly saw and heard at that show that you played in LA, and at Daytona that led to the six years of working together. So obviously, luck was a part of it, but the other part was you guys were apparently good enough and filled the need that she had. What’s your advice for somebody that’s, “Yeah, I’m just looking for my break”?

[0:38:58.6] Kate: Gosh, I think a couple of things. I think one, yes, finding someone who will champion you is super important. Somebody who recognizes your talent and your gifts. I think that that is super important. I think whether it’s somebody, it can be a spectrum from a friend who’s just super encouraging, that sees something in you that pushes you to go forward, or on the other side of the spectrum, a celebrity or somebody with a ton of influence that can be like, “Hey, I believe in you. I see something in you. I want to bring you along,” or like, “I’m going to connect you with these five people, because I see it for you.”

I think that that is so huge. Finding someone, or ideally, like a team of people, but someone to champion you or your talent, or whatever it is that you’re pursuing. I think that is important. But secondly, we would say this all the time, there are more talented singers out there. By all means, it’s not like we’re the only ones, and actually, Kelly said this a lot of times. Not in a threatening way to her band, but she would say it about herself, too, like, “We’re all replaceable.”

There are a million people who can play the bass, or the guitar, or even sing, and she would always say it like, “We’re all here for a reason.” In one sense, I think we always say if you have a good attitude and if you’re a good hang, and I think that’s such a Nashville thing to say, but if you can be low maintenance, low drama, it will take you a lot further. Like, somebody with a good attitude, I mean we’ve seen people go and come based on attitude alone.

They’re insanely talented and you’re like, “How could you turn that person away?” or “How could you send that person home based on their talent?” But the reality is, at least for touring musicians, you’re on stage for 60, 90 minutes maybe. You’ve got 23 and a half hours left of the day that you’re going to be hanging in close proximity.

Do you want the person around that’s going to be complaining that everything isn’t right? I just feel like having a good attitude, and that’s so basic, but I think having a good attitude, being humble, being willing to serve.

[0:41:18.3] Jill: And putting in your work, whatever that is, before so that you’re ready when that time comes. I think yeah, it was our first show in LA that she came, but we sang in harmony a hundred percent of the time getting ready for whatever it was.

[0:41:35.0] Kate: Yeah, anytime we were in the car we were singing in harmony. We were annoying.

[0:41:40.2] Jill: Just working on your craft. That seems so elementary, but it’s so true.

[0:41:44.8] Kate: Yeah.

[0:41:45.8] JG: Yeah, that’s something that strikes me, is you guys forged a connection and were working really hard so that when the big break came, you didn’t fall on your face.

[0:41:57.5] Kate: Yeah.

[0:41:57.7] Jill: Yeah, I think it’s just readiness, for sure.
[0:42:00.2] JG: I mean, you performed in front of 250,000 people, that’s crazy. You had that, and you’re admitting that you were as freaked out as I would be, but I assume that if, you know, that happened the day after you guys left that study abroad experience at Martha’s Vineyard, it might not have gone so well.

[0:42:21.2] Kate: Yeah, absolutely.

[0:42:23.0] JG: That’s cool. Parting advice or lessons learned from the past 13 years of playing music professionally?

[0:42:31.8] Kate: Oh, surround yourself with good people.

[0:42:34.8] JG: Be a good hang.

[0:42:35.6] Kate: Yeah, be a good hang.

[0:42:37.6] Jill: Be prepared to lose things. Someone told us this once. Like your favorite sweater when you’re on tour.

[0:42:43.8] JG: Oh, I thought you meant like, soul things, but you’re talking about actual things.

[0:42:47.9] Jill: Oh I’m talking about a wide range, so there’s like that, or there’s friendships you lose when you’re on the road, or like money, or time, or whatever.

[0:42:57.0] Kate: Or a little bit of sanity sometimes.

[0:42:58.4] Jill: Yeah be prepared to lose things, and I don’t mean that to be whomp-whomp, but it’s the reality. It’s a sacrifice, and it’s not the easy choice. It’s not the guaranteed choice like, “Well if I do this, this would happen.” No, you could end up losing it all, but if you really care about it, you’d do it anyway.

[0:43:19.0] Kate: And don’t be afraid to fail or lose.

[0:43:22.0] Jill: Or suck.

[0:43:22.8] Kate: Yeah, don’t be afraid to suck, because you will. There are people than are more talented, there are people that are prettier, thinner, younger, all of those things, but if you can just be sure of yourself and what you bring to the table, and a lot of times, it doesn’t make sense. If I were Hoda, 27 times, you might be thinking like, “Maybe I’m not that good,” but she just knew that this is what she was going to do, and she did it.

[0:43:51.5] Jill: It could be a little crazy. If you’re a little crazy, you’re good.

[0:43:54.0] Kate: Yeah.

[0:43:56.7] JG: Yeah, well I take issue with the idea that somebody is skinnier or prettier than me. That’s probably true…

[0:44:04.6] Kate: Yeah, we weren’t really talking about you.

[0:44:06.0] JG: Other people, other people. Good to know. Guys thanks so much, this was great. Thanks for sharing your story.

[0:44:11.6] Kate: Yeah, thanks Jeff.

[0:44:12.2] Jill: Thanks for taking the time.


[0:44:19.6] JG: Hey guys, thanks for listening to the Portfolio Life. You can find the show notes for this episode and others at goinswriter.com. If you enjoyed the show, you can leave a review at iTunes so more people can find it, and my ego doesn’t die a slow tragic death. I appreciate the time you take to listen to the show. I’d love to connect with you on Twitter. You can find me @jeffgoins. You can also email me at jeff@goinswriter.com with tips, ideas, feedback, compliments on my hair.

Anyway, thanks for listening. I look forward to talking to you in the next episode. Now go build your portfolio.

As songwriters should admit, I think you’re lucky if you get a good one out of 50 or 100. —Jill

Click here to download a free PDF of the complete interview transcript.