From Rock Band to Real Estate: The Mindset That Changed Everything

What does a rock band have to do with real estate success? Everything.

In this episode of the We Attitude Podcast, David sits down with Jeremy Barrett to break down a journey that most agents would never expect—from playing in bands across the country to building a real estate business and leading at a high level.

But this isn’t just a story…

This is about discipline, repetition, teamwork, and the truth most people avoid:
 You don’t succeed alone.

If you’re a real estate agent, entrepreneur, or someone chasing growth, this conversation will challenge how you think about practice, consistency, and what it actually takes to win long-term.

In this episode, you’ll learn:

• Why practicing hundreds of times is the real path to mastery
• The mindset shift from “me” to “we” that changes everything
• How failure, uncertainty, and risk shape long-term success
• Why top producers need systems, not just hustle
• How Jeremy went from musician to server to entrepreneur to team leader

Key takeaway:
 You can go fast alone…
 But if you want to go far, you go with others.

If this hit you, comment “WE” below and let us know what stood out.

0:00 – The “We Attitude” That Changes Everything
 0:47 – Meet Jeremy Barrett (From Music to Real Estate)
 1:42 – The Motorcycle Trip That Started It All
 2:56 – Joining a Band (And Learning to Bet on Yourself)
 4:51 – Life on the Road & Early Success
 6:09 – Playing Shows, Day Jobs, and the Grind
 7:33 – Why Practice Matters More Than Talent
 9:16 – 1,000 Reps for One Song (The Discipline Nobody Sees)
 10:50 – From Music to Marriage to St. Louis
 11:08 – Lessons That Still Drive Success Today
 12:30 – The Power of Team & Shared Struggle
 14:38 – Discovering Real Estate (The Turning Point)
 16:26 – Early Wins & Building Momentum
 17:24 – Burnout, Growth, and Finding Systems
 18:10 – The Leadership Shift That Changed Everything
 20:24 – Pushing Your Limits & Growing Others
 21:00 – Balancing Family, Business, and Growth
 22:36 – Translating Music & Service Into Real Estate Success
 24:17 – Why Musicians (and Athletes) Win in Business
 26:20 – Final Thoughts: The Power of “We”

Transcript

SPEAKER_01 0:06

Alright, welcome back to the Wii podcast. We're excited to have you. Uh we're actually like almost pros now. We're about six or seven episodes into it. And I was told that I can't use the fact that we're newer to it. So I want to make sure that uh my guest is aware that now I I'm like Joe Rogan. I'm I'm fucking coming out for you, man. Just hang tight. We're gonna be there uh sometime in the next 50 years. So anyway, um I'm excited. Uh Jeremy, uh I'm excited to spend time with you. Um so just tell us a little bit about yourself, like how you how like just before we get deep into just just say, you know, uh how we know each other, what do you do, like what who you are to us, and all this stuff. Love it, love it.

SPEAKER_00 0:47

Um Jeremy Barrett. Um I'm the team leader of Barrett Group. I've had the privilege of being the team leader of uh Keller Williams West Market Center under your leadership. And um now we I run a small team here. Uh it's myself, my wife, um, I've got a marketing director, Amanda Starts, on the team. I've got she's got an assistant as well, and I've got two other referral agents that are on the team. I'm really the only one in production right now.

SPEAKER_01 1:13

Cool. Yeah, awesome, awesome. So uh we've known each other for a bit, and I think a lot of people uh may not fully know Jeremy, I guess, maybe to the extent I had the ability to to to to experience it. And one of the cool things we have in common is neither of us went to high school in St. Louis and and we're still able to make a living here. So that that says a lot. Yeah, right. It's it's a it's a it's a unique thing uh as far as St. Louis is concerned. So if you're not from St. Louis, you can't understand this joke, but for those of you who are from here, you get it.

SPEAKER_00 1:42

Yeah, we never asked the question of where you went to high school in my small town of Jackson, Michigan, because it was it we're gonna be. Because no one cared. No.

SPEAKER_01 1:50

So so all right, so let's talk about this. So so how did you get to St. Louis? Like what, like how did you get here? And and wow, and and when did you get here?

SPEAKER_00 1:59

Okay, so originally I got here. Um you know, my journey goes back, you know, like like you just said, we didn't go to college. Yeah, you know, this was something right out of high school, tried some community college, um, wasn't really my wasn't right fit, yeah, if if you will. So um dad about a semester in, and then um, yeah, I told my mom that uh and dad that I was uh riding my motorcycle to Alaska to find to find what to find what I wanted to do. You're gonna ride your motorcycle? I'm gonna put a backpack on the back, ride my motorcycle to Alaska. Um didn't really do much research. I was thinking about getting a job. Do you know how tall it was there? It was the middle of summer. I was like 50, I think. So that I mean, I'm thinking there's so many places you can ride a motorcycle. I I get it, but you know, I wanted to go up through Canada. It was great. So got there, ran out of money, didn't I went to Anchorage, 4,000 miles, ran out of money, didn't find any work whatsoever, came back home and joined the band.

SPEAKER_01 2:56

Okay. So my parents, my parents are thrilled. Awesome. So, right, the the whole theme, if you will, of our conversations we've had so far in the podcast is about kind of having a we attitude, right? Sure, I think that the world turns in a kind of weird way right now where everybody's got an idea and an opinion, and everybody wants to do it their way or themselves. Right. And and I just it's something I'll ever buy into. I don't believe in this. I think no one can achieve the level of success they want or fulfill their potential by themselves. I think everybody needs help, needs a coach, needs a mentor, needs a team, needs support. Um, so joining a band, like how like you've been playing for a while, like what what's your musical history that got you into that?

SPEAKER_00 3:37

My musical history was I I did play saxophone in high school. Okay. Well, actually starting in like fourth grade. Okay. And so when I came back, my buddies from high school, they had formed a band, uh, great friends. We we connected through music, laughter, just experiences. They had formed a band and they needed a bass player. So I was like, you know what? I'll teach myself how to play bass. I can, I can, I can I can I can do this. Okay. So it's always it's always been okay, you know. They they had they had a need. So I was like, and I want to be part of it, want to be part of that team, part of that band. So I told myself how to play. Wow. So we we started, we started off. Uh, I remember we played an open mic in Ypsilanti, Michigan. It's about between Ann Arbor and in Detroit. And um we we did well. They it's kind of like a movie. They pulled us in. The the owner of the place pulled us in. It's like, hey, I want you to open up for this this other band that's been doing successful, that just had a national band that they opened up for. So we're like, oh man, we're hitting big time. I mean, yeah, I mean, they weren't gonna pay us anything really. Sure. But it was it was the first time together, like that we had we had rehearsed together, we had gone through it, and we went out there, put it out there, and you know, somebody liked us, and we actually started playing after that, dude, like just college towns and stuff.

SPEAKER_01 4:51

So nice. That's awesome. So, did you stay there in Michigan for a while, or did you guys hit the road? I mean, I'm thinking you guys get a van and start funny.

SPEAKER_00 5:02

You should say that. Yes, we did have a Ford Cataline 150 band. It was provided, it was provided by our lead singers. Uh no, we we got a van. Um, and yeah, we we start we started just doing that like the college little tours and open and stuff like that. So we stayed there for a while. Uh eventually that band did dissolve. The lead singer went down to Nashville. Yeah, and then I followed him down there about six months later. Okay, and we we started a new band. Okay. It's kind of a different. So we were in Nashville for a little bit, and um, we found some friends down there that got together, and then later on, we went from Nashville to Chicago. Okay. So now we're in Chicago for about 10 years. That's where we had a bit of our success. Um, one of the original members from our the band that originally started, because these are all high school friends, too. Sure. That we still kind of we still have a tech's group right now that fires off every single day with these guys. So it's awesome. But um, so we get to Chicago and that's when we started having a little bit more success. Okay. We we started getting into the circuit. We're we're all playing originals, we're able to um at this point kind of work our way up, start playing bigger shows and stuff. So it was just it was a lot, it was a lot of fun, a lot of work, a lot of fun.

SPEAKER_01 6:09

Yeah, so good. That they should go together. So so what's uh bigger shows? What that what is what does that mean?

SPEAKER_00 6:16

So here's the thing we all had day jobs, yeah. Okay, and so when we started, when we started playing, you know, we're able to get bringing four or five hundred people to some of these clubs down there, and then you know, were asked to to play on a little bit larger scale. We started getting a touch of local radio time and stuff. I don't know. I mean, we just we really never hit the big, it was a really weird time in the music industry. We were booking through MySpace, you know, and like it was just like this evolution. iTunes was just coming out, you know, and so it was this weird evolution. And so we were kind of caught up in that. But yeah, it was rehearsal during the week, go out on the weekends. We all had day jobs at that point. I was um waiting table to find dining restaurants, and so it was really that. I mean, that was my team. Yeah, that was I mean, that was our group, our team.

SPEAKER_01 7:04

So uh yeah, that's that's we're so so you mentioned uh and you know it is because we've worked together, but like you've mentioned you guys were rehearsing all this stuff. I'm right. I'm a huge believer in taking raps and practice and all this stuff. So um I'm sure from a music perspective, that's even more critical. Like you can swing a listing appointment here and there. I'm thinking like getting on stage and and just just running without any kind of consistent practice behind it is probably a little harder.

SPEAKER_00 7:33

Well, yes. And I mean, I I go on a listing appointment by myself. Yeah, at times, sometimes Kelly, she's on the team's. Sure. Yet as a band, so we we know each other. I I you know I I can I can tell if somebody gets just a slightly sour note wherever on stage, too. So that was that was the one thing that I mean, we rehearsed and rehearsed and rehearsed. I mean, it was all it was during the week, it was on the weekends when we were playing. We were coming up with our original music, so we were coming up with our parts, our pieces, making sure they fit. And and I'm telling you, so when we're on stage, you can't hide that. You know, I mean you can't hide messing up, you can't, so it's and we obviously we did, but in the middle of a three and a half, four minute song, you gotta be able to pull it back together in the moment and make it make it look like hey, nothing happened. Right. Yeah, so it yeah, it was it was definitely rehearsal practice, time on task. So nice.

SPEAKER_01 8:29

So, how much practice goes into um into your average week before I guess Saturday night Saturday?

SPEAKER_00 8:39

You know, you know, early on, depending on where we were with the song, you know, if if it was a newer song that we were just coming up with, working on parts and doing all that, it'll give it a significant amount of time before it even hit stage to test it out, you know. So, you know, time-wise, I mean, especially if we're going in the studio, and you gotta figure out where we go in the studio, we played that song uh, I would say at least a thousand times. Wow. You know, like like in its entirety, for sure. At least, you know, six, seven hundred to a thousand times. Crazy in different in different ways. And while we're in the studio, depending on how it went, we were end up, we were making changes then, and and still it was just it was we had to have that bass.

SPEAKER_01 9:16

Yeah. So, and that's where I get three minutes on.

SPEAKER_00 9:20

Yeah, for sure. Yep.

SPEAKER_01 9:21

So so you said you guys did this for you, you were you you ran into the that circle for about 10 years. Did I hear that? Actually, no, that was so that was from when I was about 19.

SPEAKER_00 9:32

No, because I'm older than you. Uh that was from about 19 years. Yes, you are. It's that that that'd be no, don't add it. 19 till about 33-ish, 34-ish. Okay. So that that's that's what that's what we did for that many years. And then um that's when I met my wife, Kelly. Okay. Um, at that point, um, she she's from the St. Louis area. Okay. You know, I'm originally from Michigan. Yeah. We're in Chicago. And so you can get as far as getting here, this this is around 2012-ish. Or no, actually a little before about 2012 is when I started real estate. I met Kelly in 2008-ish. Okay. Uh 2008. And so at this point, we had um we had met and still playing in the band. She she had a great job pharmaceutical sales. I was in a band. She transferred to uh Chicago from St. Louis. I said, give me three years, it turned into six. Yeah. And so and so um I wasn't I was a great negotiator already back then. Um but no, it didn't so after that um we were decided, we we got we got married, had kids, yeah. We had two kids, we decided we it's either in Michigan or St. Louis. So at that time, that's when we decided to come back to St.

unknown 10:50

Louis.

SPEAKER_01 10:51

Gotcha. So before like so before we get into that part, tell me what are three or four things that you still carry today that that your your musical career life has taught you? That you're still you're still using it.

SPEAKER_00 11:08

Um it's hard, and no matter what, you never give up. You know, that that was one thing. We we still we still we'll still play. You know, and and that and that's I think I always knew that whatever I pursued, that I was gonna give as much as I could and hundred percent, you know, kind of hundred percent into that.

SPEAKER_01 11:26

Yeah.

SPEAKER_00 11:27

That taught me that I I wasn't I wasn't a solo, I wasn't gonna go out there and just play with my bass on the corner of the street, you know what I'm saying? So I think that that taught me uh a different form of having to communicate with each other. I mean, they're they're they got to the point where we could communicate, it was like unwritten, like like unlike non-verbal type things that we had to communicate with with each other. So the communication was unreal. The friendships, my I mean, like I said, to this day.

SPEAKER_01 11:55

Yeah.

SPEAKER_00 11:55

I mean, they they're they're my they're my tribe. They're you know, so just that camaraderie. Um it taught me that to be resilient as well.

SPEAKER_01 12:04

Yeah.

SPEAKER_00 12:05

And yeah, and I think that those those things, all of those things, really.

SPEAKER_01 12:09

Sure. And and and it's I I believe it when you say these are your uh your that's your family and your friend. I mean, you spent a thousand hours practicing something without any kind of certain outcome from it, but but you have a group of people that is committed to spend that much time together without a clear outcome.

SPEAKER_00 12:30

Like you you can't help but have a very different bond with well, not not to mention that we've talked about this too. When you travel on the road with some we we were traveling on the road, we were at hotels, we were playing shows with no people, we were playing shows with packed people, we were having experiences together. Um, and don't get me wrong, it wasn't all sunshine and rainbows and and all that. Sure. But uh it but the the great outweighed the very few. We we got along really well. Yeah, I'm not gonna lie. Yeah. So it was it was an amazing experience. So how did you find real estate? How do we go from I like finding real? I like I like that. It's not to make people really they they kind of find it or so. I think real estate kind of found me. Yeah. Um it was after my wife and I had purchased our first home. Okay. We purchased our first home, we had an experience that we we bought a foreclosure. Okay. Um, did some we did we got 402 or 403k loan. That was the rent FHA renovation loan, so we could put some 20% equity into it afterwards, refined it, um sorry, um refinance it, yeah, um, do all the renovations and stuff. I'll be honest with you, our our friend was our realtor, did great, it was amazing. Um, I saw his paycheck, I was like, wait a second. Um what do I need to do that? Yeah, I'll be honest. Sure. It's like what a great experience. And I was like, what do I need to do that? Because at the time, you know, I've been waiting tables on waiting tables, serving tables, playing in a band. There was a brief period where I actually started a catering company. I love food and music. So I started a catering company for four years because I was catering to pharmaceuticals. Oh, yeah. Because Kelly was up there doing pharmaceuticals, doing lunches and stuff. So I was looking for a way because at that point the band was I won't say dissolving, but it was just like, you know, hey, we're we're probably at our people were moving on. People are moving on, yeah, for sure. And and so that was the time where it's like, okay, what am I gonna do? Yeah. And you know, I it was Gavin was Gavin was born, roast born after, you know, and so it's it was like what what what's next? You know, because I I wanted to step up and do something, and that looked like it would be something that I enjoy. Yeah, and I could duplicate and go from there.

SPEAKER_01 14:38

Cool. All right. So what year did you get into real estate?

SPEAKER_00 14:41

Did you start here in St. Louis? No, actually, I it was while we're in Chicago still. Okay. Uh got my feet wet for about nine months there. Yeah. Um so that was right around 2012. Oh, okay. 2012. My and so yeah, I was with a boutique real estate company up there briefly. Yeah. Um funny thing is they hand me a they hand me a uh a millionaire real estate agent book and say, this is what you need to know here. Like I I was kind of confused. I actually didn't even open the book at that time. I was like kind of confused saying, okay, I I'm with this brokerage, and yet, yet, okay, they hand me that. But um, so I started, yeah, that 2012 I started there. Okay. Yep.

SPEAKER_01 15:20

All right. So and then you moved here 2013. 2013. Yeah. Right. Which St. Charles was up and running then. So did you start there? Yeah, okay.

SPEAKER_00 15:30

Um, yeah, well, actually, no, no, no, I wasn't at KW when I started. I started um a brief brief synt um at another company over in uh town and country. Okay. And I was there for about 18 months. Okay. Uh, this is the first time I was able to go full-time. Okay. And so that was, you know, at that at first, I was I was talking with Kelly and I was like, can you imagine if I just made a few thousand bucks a month? Yeah. Doing real estate, this this would be this would be sweet. This would be awesome. Yeah. So it was October of 2013 when I got my license. I didn't really start because we were renovating another house in Webster Groves at the time. Um but it was like January or December of 2013 when I really started like going after it. Yeah. And so within the first two months, I was able to close or get six under contract, closed uh um by February. I had six clothes, I had six closed. Um, I was working this lead system to where my bread and butter was just working online leads.

SPEAKER_01 16:26

Yeah.

SPEAKER_00 16:27

And converting a completely different animal these days, yeah. I was able to convert a pretty high level. Yeah. And so yeah, that's where that's where it all started. So I was there for about 18 months. Nice.

SPEAKER_01 16:36

All right. And then how'd you find KW?

SPEAKER_00 16:38

Why'd you go there? So um after about after about seven or eight months, I was getting busy. I did, I mean busy by sure. Just whatever you knew I didn't know. Yeah, for 13, 14 hours a day, just didn't have any systems, didn't have any, yeah, didn't have any procedures, nothing. It was just me going out just as much as I possibly could. So um I'd been receiving a few texts and calls and everything like that from John Sprague at the time, and we finally met and sat down. And at that point, I I'd gone to our managers and said, Hey, I'm I I need to grow. I need I need to figure something out here. I I can't do 14 I don't want to miss anything with my kids. And I'm working 12, 14 hours a day.

SPEAKER_01 17:24

Yeah.

SPEAKER_00 17:25

And I need to continue to grow. I want my cut. I in the service industry though, when I was waiting tables as far as fine dining, I experienced such an awesome, amazing, um uh like just a great experience in customer service and how to really pamper and take care of people. And I wanted to include that into my business with customer care and customer service. Sure. So I didn't have a solution. And so I went to our manager at the time and said, well, we maybe we can get you somebody that can do some paperwork, but he's like, it's not really paperwork's great, but I want to create an experience. So met with John, showed me the Red Book and actually opened it this time. So um showed me some systems, models, levels, and it's like, oh my gosh, that's exactly what exactly what I was looking for. Yeah, like 100%.

SPEAKER_01 18:10

Cool. So you've been with us what like uh third 12, 13 years, I guess, right? Yeah. So so you've experienced uh you've been on the leadership side of things, you always you're successful agents. So just as a whole, like how how do you view like the value of leadership and how did that show up in your journey and and what role did that play for you? Wow, great question.

SPEAKER_00 18:33

Um so you know, after after a couple years being in here, it was the I I did get the opportunity of being a team leader, and and also as far as lead how leadership goes, it's it's trying to try to think out about this. So the amount that I've learned just from you know, believe it, a leading team at the market center, yeah. It's it's it's priceless. It's it's it's it's taught me more about myself, um, how to go with others, because that's that's the key.

SPEAKER_01 19:07

Yeah.

SPEAKER_00 19:08

Because we all know, yeah, you can go fast or loan, but if you want to go long, go with others. And that's I think that's that's helped out, especially with my longevity in the business, yeah, and consistency in the business. So I don't know if that really answers your question or not, but I mean it's there's no right or wrong.

SPEAKER_01 19:23

No, I I get it. I get it. I I just think it I I just think leadership or experiences impacts people to journey differently. Right. I was just curious to see what how it impacted you as well.

SPEAKER_00 19:33

Well, well, here's here's the thing. So and honestly, it like I I never knew what I I knew I could do, yeah, but I never knew what my ability was. Okay. And until until what I've what I've learned being with this organization, and not in in in you know, with our organization that we had. I've learned so much and being able been able to push my lid and push push my comfort zone, and and then in in turn being able to do that and help others to do the same thing. So that that to me, it's had such an amazing impact on on my family, my business, my community, agents around. You know, I've I've I've and it's all it's all based upon that leadership, and it really is uh teaching me how to think in a different way, in turn be able to do the same thing.

SPEAKER_01 20:24

So that's um what's what's the future for you? What are you what are you looking for? What's on your what's on your to-do list over the next three to five years for for your your your your your group, and and you're kind of in the thick of it with the kids? I know you're you're such a sophomore now, I think.

SPEAKER_00 20:40

No, he's he's he's still for he's freshman. Freshman, okay. Yeah, freshman. He I can't believe he's all he's almost all the way through his yeah, you know, uh freshman year.

SPEAKER_01 20:48

So you're getting into the I mean he's an athlete, you have athletes in the family, like you're you're busy every night, every weekend. So what's the next three to five years for your group and business and all that looks like?

SPEAKER_00 21:00

Yeah, no, um, yeah, Gabin's super busy with football. Rose is amazingly in basketball, Rose is amazingly busy with basketball and and soccer. She's amazing, and and Ruby's discovered dance, so that's that's great. Um yeah, we're we're busy, we're in a thing. You know, and I would say that in 2025 I did a bit of nesting, you know, moving and nesting and everything to accommodate this, yet still had my my second best year in real estate by by literally about $8,000 of GCI compared to 2021. That's awesome. So the future for me, it's continue to grow. Yeah, grow myself, grow grow. Um I'm I'm really leaning into um now that we've got our our systems, everything's everything's up and running. We're we're good now. I'd like to I'd like to find some of those uh uh agents that are aligned or uh people that are aligned with you know cultural fits with the team that wanna focus on you know build building their wealth. through either flipping or holding and and also just just generating um just j generating more profit for themselves through sales of real estate. So I'm I'm looking I'm looking to grow the team for sure. And I think that's something that of any year that we've done this that this is this is a time that we we definitely have the tools, the value and everything to be able to do so. So next three to five years, you know it continue it's really just continuing to grow. You know I'd I'd like to help help build whoever's on the team a portfolio of investment properties and and have those opportunities for them too.

SPEAKER_01 22:36

That's awesome. So so if you combine the journey of being a musician being in the band your experiences through customer service uh as a as a server and all this stuff how much of that has translated into your real estate business today?

SPEAKER_00 22:53

Oh significant significant yeah especially especially like the the attention to you take you take the service aspect of it the attention to detail that that and that was a team in itself too I mean that that that was not just me fate front facing that that this was I had people behind me to um from from start to finish. I mean that was more that was I was actually considering going into the real estate I'm sorry into the restaurant business prior to real estate however this that opportunity presented itself beforehand. So but that that's a that's a team from the front of the house back of the house and that it just everything that is that's translated it tremendously into real estate because it is front of the house back of the house and and and everybody has to ever everybody has to work together seamlessly timely to be able to get something to that table get somebody to the table to the closing table to the closing table. Yeah that's right so so so I mean that right there in itself the band the band was really it's just it's being able to communicate to practice to work to to and same thing with restaurant too that all that all shows up in in real estate all of it shows up because as as a team I'm responsible for everything but I'm not responsible to do everything. And so you know so so and and everybody has their lane that they stay in and if we need to cross over we can at times yet it's just it's just a a a well little machine.

SPEAKER_01 24:17

Get on your plate right right yeah right it's awesome well I I love the conversation I I I I remember the first time I heard your your journey as a musician I I I never anticipated that and I'm jealous I uh I uh I suck at music and uh I I got kicked out of most of my music classes because I because I was I wasn't good so then I started disrupting everybody because I didn't want to practice and then I get kicked out and then so the second I was able to pick a different like you know when it became an option kind of like yeah I'm like I'm out I and uh I just never had the patience to do it but I think uh I think it's it's amazing when you talk to musician it's amazing the amount of uh uh you can't deny the work ethic of a musician because the amount of practice that is required to be able to to get on stage at whatever level just you know I mean even to even younger kids like you whether it's high school or you get to college but just to be able to get in front and and people wanting to to listen to you is requires a huge amount of practice and and I think I think that translates for everything it it becomes kind of a behavior like it becomes part of who that person is and when you find that out as as a business owner now like I bet you know I I have a a weak spot a soft spot for athletes to come and join my work as I know how hard it is and I I bet if you find younger agents that have a passive music and knowing what it takes to do it you would probably be that much more attractive to them because of the understanding you have of their journey and I think um so anyway so I I just think it's it's really cool right everybody wants to be a rock star and you get to do it. So for a brief moment yes yes that's awesome well I appreciate your time man I'm grateful to to be on your team I'm grateful that that I get to to work with you and uh I'm I'm glad you stopped by and we got to chat today.

SPEAKER_00 26:20

Well thank you and thanks for everything you do as well.

SPEAKER_01 26:22

Thank you brother