In this episode, Zach Dando from Denver, Colorado, shares his career journey, spanning from the excitement of professional baseball to coaching 350 games, turning pro in golf, ranching, and now creating music that’s garnered over 500k streams on Spotify.
Ever wondered what it’s like to pursue your childhood dream of becoming an MiLB pitcher for the Houston Astros, only to find that it's just one chapter in a much grander story?
In this episode, Zach Dando from Denver, Colorado, shares his incredible career journey, spanning from the excitement of professional baseball to coaching 350 games, turning pro in golf, ranching, and now creating music that’s garnered over 500k streams on Spotify. Zach opens up about the highs and lows of each transition, the challenges he’s faced, and the valuable lessons he’s learned. He highlights the importance of seeking support from those closest to him, particularly his beautiful wife Gabi, and the profound fulfillment he finds in helping others and making a positive impact. Join me to discover how perseverance, self-reflection, and a strong support network have shaped Zach’s career.
Episode Takeaways
Connect with Zach
Jenny Dempsey (00:00.014)
You'll never fail if you don't quit. Just keep going. And that's all I can say before we go is you're the only one, you get to decide when it's time to quit. You get to decide when it's time to be done. just, whenever that goes, if anybody's out there listening, just know that that's you are the one that's in charge, not the world, not someone else. Welcome to The Career Flipper, a weekly podcast featuring career change stories from people all around the world.
from all walks of life about how they get from point A to point B and all the twists and turns in between. I'm Jenny Dempsey, your career flipping host. After more than a decade working in customer service and experience leadership at tech startups, as well as teaching to you to me customer service training courses, speaking at business conferences and running a global customer service mentorship program, I found myself laid off in 2022 from my stable corporate job. And despite my years of experience, I couldn't find a new job.
and I really started to question my worth. What am I supposed to do now?
A friend then gave me an old junkie table. I saw potential. I binged YouTube, TikTok, and Instagram videos to learn how to fix it up and found joy in giving something unwanted a brand new chance at life, which really resonated with me after getting laid off and feeling unwanted myself. This led me to start my furniture makeover and restoration business, San Diego Furniture Flipper, where I rescue and restore good furniture to keep it out of the landfill. Alongside that, I host this show, Speak It
events, do customer service consulting, and offer one -on -one career change coaching sessions. Despite all this wonderful stuff though, I was feeling alone and kind of delusional about my new path. I mean, who really goes from the corporate tech stable world to cupboard and paint and sawdust in their garage wondering if they're going to be able to sell their piece of furniture on Facebook marketplace. So I started to reach out to a few people that I knew who've also done some career changes and hearing their stories motivated me.
Jenny Dempsey (02:03.236)
And it made me realize that it's okay to change direction at any point in life. And I realized there are way more people out there who flipped their careers more than I've ever imagined. And that's why I started this podcast. It came to me in a dream to share these incredible stories and offer support to anyone considering having already been through or currently going through a career flip.
I hope each episode brings you something that you can take away and use in your own life. New episodes drop every Thursday and I've got some bonus episodes once a month sprinkled in on Tuesdays just like this one that you're about to dive into. I like to call these bonus episodes cocoon episodes because they capture our guests right in the midst of their career metamorphosis. There's so much we can learn from their experiences. The highs, the lows, and everything in between to feel a little less alone on our own.
So let me ask you a question. Have you ever chased and achieved a childhood dream only to discover it's just one chapter in the bigger story of your life? In today's episode, you'll meet Zach Dando from Denver, Colorado. He shares his career journey from the thrill of professional baseball to coaching 350 games, turning pro in golf, ranching with horses, and now making music that's racked up over 500 ,000 streams on Spotify.
Zach talks about the highs and lows of each transition, the hurdles he's overcome, and the lessons he's learned along the way. He also opens up about the crucial support he's received from his wonderful, beautiful wife, Gabby, and the deep satisfaction he gets from helping others. Let's get into the episode now. Hello, Zach. It's awesome to have you here on the Career Flipper. Thanks for making the time. Yeah, how we doing? Thanks for having me. I appreciate it. Awesome. Yeah. Tell everyone.
Yeah, my name is Zach Dando. Right now I live out in Elizabeth, Colorado. Currently I am a ranch hand from my wife and working on my music career. know, it feels awesome just being here to, you know, just share some of that stuff with you. And I know I got a lot of twists and turns on this particular episode. So I'm excited to just be here. But yeah, we're out in Colorado holding it down right now, you know.
Jenny Dempsey (04:19.691)
work all day in the morning and then just get right to the career at noon.
Jenny Dempsey (04:33.518)
amazing.
is your wife is exceptional and does amazing work you can tell
Jenny Dempsey (04:45.326)
functioning for those those beautiful creatures. you know, let's get into it. Zach, tell about your career flips. Tell us the stories that led you through your journey. Yeah, my goodness. So I guess I'll probably go back to just right around high school. You know, I was playing baseball just like everybody else. I was, you know, put my whole life into it. So I was lucky enough to let her as a freshman and played four years of varsity baseball, won a couple of state championships, had a lot of success. And because of that, I was able to play baseball in college.
and went to a junior college and didn't have the money to go to a big, big time D one. So I had to take a downgrade and went to community college route, went down to central Arizona. So you can imagine how warm that was. It right in between Phoenix and Tucson. So in the middle of nowhere, if anyone's familiar with that spot. But then that's just when I got to work, you know, I was on scholarship for, for baseball and we happened to be one of the best teams in the country. I was able to be, you know, the lead pitcher on that team and
We, jeez, we were able to go all the way to the national championship game, which actually is randomly back here in Colorado, which is crazy for the whole United States. So I was able to be the number one pitcher on the number one team. And unfortunately we lost in the national championship game on a walk off home run in the 10th. So it was awesome. mean, I wasn't, you know, I didn't get up the home run, you know, but.
It still felt just like as big a loss as any I'd felt in my life. And it was so bittersweet because two days later, the draft happened. So I wasn't sure where I was going to go to school if I wanted to go, but I got the call from the Astros and they said, do you want to come play professional baseball? And I said, yeah, absolutely. So from that season, I just went right into, I went down to Florida pretty much to check in in the spring training facility.
And yeah, just started my baseball career pretty much immediately two days after the national championship. not much time to reflect or come down from that and had to go right back into it. And that's just when I wasn't quite sure what it looked like to be a professional baseball player. it took me a couple of months to get used to the grind. And in college you play a few times a week here and there. And I mean, it seems like a lot when you're a college athlete, but nothing compared to what the grind is.
Jenny Dempsey (07:04.106)
I'm at that level. you know, after I after that year, I just came home and I was like, Whoa, I had a whole off season, which I've never had before, you know, so no more school, no more anything. So once November came around, it was really just, you know, learn how to work like a professional. And that was really the toughest part because, you know, I always started thinking that it was just about effort, right? Like,
I just wanted to lift and wanted to work out and everything was so intense. so, luckily I was young enough to do it like that at the time. I wasn't getting tired or anything. But those are the things that you learn throughout the course of your career is how to make those adjustments to where everybody when they start a new job is always so excited about the task at hand. So you want to show who you can be and you want to show what kind of teammate or what kind of leader you are on the team, whatever your team may be.
really just was grinding for the sake of grinding. the good news is, is I was prepared because of that, right? A little bit burnt out, but wasn't really able to focus on the specialization that was required for what my job was going to be as a specific relief pitcher. So my whole career, I was a starting pitcher, which means you throw 200 pitches, not that many, 100 pitches a game all the time every fifth day.
You get in a good routine. And when I got drafted, they wanted me as a relief pitcher. So that was a huge adjustment going from, I have five days to prepare for my start to every other night. I could be up at any given time, regardless of the situation, you know, who are depending on who's batting. So it was really a big, a big adjustment in my routines. You know, all of my routines had to now go from all week to prep to
every single day had to be a little bit of prep for the next outing and so on and so forth. you know, having to make that adjustment as a youngster was really tough for me. But, you know, I was able to do it just because of the natural programming that the Astros provided for us. So, you know, so I was able to I was able to make an impact in certain ways that I wasn't, you know, basically, if you throw less pitches, you're going to get to play more. So as opposed to, you know, you want to throw all game all day, all the time. Now it was.
Jenny Dempsey (09:14.168)
How can I get in the game more often? How can I get in there when my team needs me every second day, every third day, every day sometimes if they needed you? So it was just, you know, really a lot of adjusting in a very, very, very talented system. And, you know, and then I met our mutual friend, Joe Musgrove, and he really just helped push me and we helped push each other to this place that was like,
We're going to do this focus, we're going to do this right, and we're going to work our tails off no matter what. At the time we weren't getting the call up, that's when you go to the next level in baseball. I think there was five levels in front of us and we were just working every day trying to get called up and nothing was happening. But we pretty much just hypnotized ourselves into competing against each other and making that work out okay. And just going along that daily grind with each other and working back and forth was what really kind of helped push me.
push me through. you know, and then just like anything else, I played three or four years with the Astros and then that one day comes where, you know, you get let go. So at the time it was really tough because Gabby was seven months pregnant in spring training and we lost all of our insurance and we were in a different hospital because we had MLB insurance and you know, we had, we had great hookups and we're excited to have the baby. And then we got home and
We had to go right on to Medicare, Medicaid, whatever one it is. think Medicaid. And now our insurance was nothing and we had to find a new hospital and life was hitting us fast. And at the time I was only 23. it was really, I don't know, it just felt like such a pinpoint of a time that it was just like so magnified. Everything seemed to quote unquote, go to crap.
And, you know, that was the time that I really had to make the decision, OK, what am I going to do now? You know, who am I without baseball? And, you know, it felt like after my whole putting my whole entire life and, you know, all the relationships and all the times you've played catch with your dad and, you know, like all those emotions now, it felt like a breakup. It felt like my heart was ripped out because it was so much more than a job. was.
Jenny Dempsey (11:25.406)
You know, it's like, wow, one day I'm playing baseball, feeling great. The next day, nobody wants me anymore. I can't even feel the wind on my face. You know, I was just so numb for probably, bless Gabby's heart for probably four or five months. You know, it was just, I didn't care what I ate. I didn't care about anything. It was just, now we have a baby, time to get, time to get everything right. Time to be a dad, time to figure this out. And you know, we didn't have baseball as our main source of income. So it was just a total.
you know, what are we going to do? And we sat down and looked at each other. If it wasn't for my incredible wife, my amazing teammate, the leader of our family as well, you know, she looked right at me and she was like, well, you can either coach. I can go back to work. I can do Pilates. I'm a horse person. can, you know, and that was when it was like, okay, let's, let's figure this out. Wow. Okay. So it sounds like it was really tied to your identity and then not having that job anymore and really asking the question of like,
Who am I without that? Plus having another life to care for and you and Gabby are just figuring it out super quick because you have to. A baby is on the way. It sounds like such a pivotal moment in your life. So from there, what do you do next? Yeah. I mean, I'll never forget, you know, just sitting there. I remember one time, you know, were brand new parents too. Like we had no idea what we were doing. We had kids first out of all of our friend group.
So we didn't really have a support system. So it was, I'll never forget one day I was just, it was like minus four degrees. think Zeke was three months old and Gabby had to run to the store and somehow we were like out of milk. Like we were out of like, she was breastfeeding and like somehow there was no milk around for like probably three hours. And I just remember being like, everything was gonna be okay. But at the time I was just this pathetic creature, a dad.
you know, a baby needs a mom. And I was just a dad without milk. And my son was just like, I could do, I could use anything but you right now. And I just remember there sitting thinking, being like, I have nothing anymore. have nothing to give on this athletic, strong, healthy guy. And I am just worthless in this moment. And I just remember that was the time that it was just like hit me the hardest. And it was, Godly. I just felt like I had worked at least hard enough to at least,
Jenny Dempsey (13:49.934)
provide something, you know what I mean? There's nothing worse than when you don't have anything in the account whatsoever and you start to slip into that mind of, you know, I'm a very spiritual person. Sometimes after payday when all the money's gone and everything's you're like, is this really what the creator I'm worth to the creator, you know, minus $20 after, you know, it's like, and those are the things that start to slip into your head. And, you know, luckily for me, I had such a good partner and Gabby is my best friend, you know, and she was just like, it's just temporary.
You know, like all of this is temporary. Let's put our heads down. You're going to be totally fine. And from then I just dove into coaching. I knew that that was my easiest way out of the whole quote unquote, you know, and, if anybody's ever coached out there, I was coaching high school. I was like varsity pitching coach. There's just not much money in that. You know, you are just doing it for the future opportunities. But, but my, you know, my, my love was restored when I was able to work with kids.
Right? Like it's not the money, it's not the bills, it's not all that stuff taken care of. It's like, you know, for me, I was, I was so grateful to be a positive, even though I was going through it, I was able to be a positive influence in these kids' life. And being a younger guy that had success in the baseball world, I had a natural little swagger about me on the baseball field. So, you know, I was naturally able to connect with these kids. And that was just what the first thing I ever thought of.
that was about somebody else doing something. Baseball was always about me doing something and me trying to do this and me having success or me giving up a home run or me striking someone out. Where this was like the first time that I felt something from an outward person, someone else was receiving something from me. I could see them grow. The information that I gave them, the stuff that they worked their butts off of that I knew.
it was really coming full circle to like, wow, maybe I don't matter that much. You know, my whole life as a baseball player, you know, like you said, my identity was just me. And now that I had this newfound love for coaching and helping kids get to these hurdles or, know, even getting to college, you know, that's pretty special when a kid lists you as a reference and you get a call from a college about a kid that you can't wait to tell them how awesome of a kid they are. You know, so those were the things that really snapped me out of it. And
Jenny Dempsey (16:10.904)
You know, I would say that one was a segue, right? That was probably a career segue, not necessarily a flip upside down because I was so comfortable in the field already. But, you know, after a while, it's like I did have to feed my family and the opportunities that I was hoping for, especially in the certain school district that I was in, weren't coming up. You know, they weren't, they just weren't presenting themselves. I felt like I was doing all the right stuff and felt like I should have got the call and I wasn't able to. So as a family in Colorado, rent was going crazy.
crazy. So we had to adjust. And, and one day Gabby was, you know, looking at the computer and she's like, I found an Olympic horse training facility. And she's like, it could possibly be living. And I'm like, well, we definitely need to look at that and go through all the stuff. And, you know, and that was how I initially got to the point where I'm like, okay, so we took that job for Gabby. She career flipped. She went from a Pilates instructor back to her first love of horses and
was able to get that job and we lived on property in this tiny little place that had no lighting, no anything. It was a pretty nasty little spot, but we had everything that we needed. It was the first time that we were able to get our head above water as a couple, as a team financially. And it was just so rewarding to go from my wife supporting me in minor league baseball.
traveling behind the bus, taking care of Zeke when I wasn't home, going to all these games, know, doing all this stuff too. Now I can be that person. So for a year, everything flipped and Gabby was the total 100 % provider. You know, all of our income came from her and what she was doing with the horses and training them and whatnot. And so I was a stay at home mom for that year, essentially. And it was amazing, you know, and I cooked every night and I had to learn how to cook and
had to watch all the YouTube videos of what meals are easy to make in 30 minutes that are still good and take him to school and get all this, know, cause this was about kindergarten, I guess he was in. So, you know, we were really just at a time where it was like, we finally had some stability and it wasn't from me whatsoever. So that was such a eye opening, humbling, but it was so cool to reciprocate all the love that my wife gave me when I was playing minor league ball.
Jenny Dempsey (18:30.104)
to be able to be that person for her, you know, to just, my job was take care of everything, make sure that it's good, do the dishes, make it to where she can wake up, go to work, provide for us and come home. you know, that's really, again, once everything kind of changed for me, it was definitely tough at times to be like, man, you're, you know, I feel, I'm not gonna say smart, but I felt educated enough too, and strong enough and healthy enough to be this big provider and it just wasn't happening.
And at the same time, you know, the universe, the creator, whatever you believe was going, this is the lesson that you need to learn in this time now. And for me, I was able to hear that, you know, and really hone in on it just go, you know, I'm just going to give this up and say, put myself aside and just be that person. And that was the first time that we really were stable and able to confidently look at each other and go, things are OK now, you know. So, you know, and then
And then a couple years passed of doing that and I was working at a golf course, just opening in the morning, just doing simple tasks so I could get back home, drop my son off, go work at a golf course for a few hours. were really cool and come back. And through that, I got free golf. So I started picking up golf as a hobby. And of course, within like 10 rounds, I was like, dang, I think I'm pretty good.
And I remember, I remember like on my 10th or 12th round, I broke 80 and that's like a big number for golfers. It's not, you know, when you play a bunch of golf, it's not that big a deal, but it's like the telltale sign that you're like, you're a good golfer. And I'll never forget it because I was just hitting, hitting the ball so well. And I randomly broke 80 and I looked in the mirror before I went to work and I was like, I think I'm going to go home and tell my wife that I'm going to really try to pursue this professionally.
And I was like on the way home, I was like looking at myself in the rear view mirror, like, you know, because the one thing I knew about myself was going to go all in. You know what I mean? And we already had all this stability time. There was this amount of time that we created in our schedule that I was able to play golf and, you know, do this. And she looked at me and she was like, my gosh, you are crazy. And she's like, but as long as everything's good and, you know, it goes, I'll fully support you. And I know that you can, you know.
Jenny Dempsey (20:49.742)
do it. So I just put my head down and played golf for a year and a half and really was just working my butt off because there's like a way to go pro on golf. have to go to school for X amount of time and get a certification. And you also have to pass a player ability test, which proves that not only do know the information, but you can apply it and teach it and redo it. And so I told Gabby in 2017 or 20, I think it was 2018 that I was like, give me one year. I don't want to waste time.
And I'm just going to put my head down and play more golf and work my butt off than anybody. And I was able to do that and pass the test to go pro on golf and was actually hoping that the golf course that I worked at was going to recognize that as something of special. You would think that, you know, you know, with my background and just being a guy that never asked for help from anybody and was able to, you know, basically pass half of the tests to go pro. I was hoping that they would help me out with the school part and they were just like, no. So.
I put all this time and energy into it and I wasn't able to get that aid that I needed. so because of that, I went back into coaching. And then, so my heart was broken a little bit again, but not as much as baseball. It definitely wasn't like, you know, the rug sweep down from underneath me. It was just more like, dang, did I really just waste a year of time? You know, and, but it was, it was such a high because I passed the test and I was, you know, in everybody else's eyes, it was so cool and so fresh and so new.
And then in my heart, still wasn't able to get the opportunities that I needed to get to that next level. so that, so that forced me to go back into coaching. And then once again, it was so cool because all the time in golf, I was focused on myself again. You know, I was just so focused on Zach getting better, Zach getting better. And I learned so much about myself that that's how my brain works, that I feel that I'm, you know, I feel better when I get better. And, and that,
once again, was still an empty feeling at the end of the day. When I went back to coaching, it still brought it back to those around you, you know, I want to see someone else do better. I want to see someone else do this. And it was always this constant ego check. And once I got into coaching, it just went away. It felt like, you know, quote, ego death, whatever they say, you know, it's like,
Jenny Dempsey (23:12.212)
That's what felt like was happening and it set me free in so many ways after that because I would never was going to define myself again by the outcome. I was only going to define myself by the process. And once I made that decision, everything else became acceptable. I wasn't so much of a victim of the outcome because of what I was doing daily and I was able to make my heart not be vulnerable to outward
actions, I guess, you know, so and then and then one day my buddy was like, you know, we when I was on the road in baseball, all we would do is music, you know, we would just joke and freestyle and rap and poke fun at each other. And one of the guys that I that I played with my roommate back in back in Greenville and Tennessee for the Astros minor leagues, they he called me and he was like, hey,
Are you still doing music, rap? Do you know anybody? He's like, I'm starting a record label. And I was wondering if you'd want to come out to LA and help me put on a show and help me basically bring up these rappers. And I was like, yeah, sure. So I went out there and I helped them. And while I was out there, he's like, I know you got some rap. Let me hear it. So I rapped for him and everything. And he pulled me aside after the whole.
weekend was over, I was just running coffees, doing whatever they needed the whole week, you know, being an assistant. And he pulled me off the side and he's like, Hey, bro, I loved your music. you, would you want to like, I would like to manage you. And I was like, man, that is incredible, dude. I was like, yeah, for sure. And so we said, let's go out to the farm and try to put together a project. So we come out to the farm and we're working our butts off and
making music and it happened time wise that the coaching job that I was doing, we needed an assistant coach. So my manager became the assistant coach with me. So then we teamed up as manager for music to, I was the manager on the baseball field and he was my assistant coach. We took these kids all around the country. played at LSU, we played out in Atlanta. I went from not knowing anything about what was gonna happen to.
Jenny Dempsey (25:28.142)
making music on the road with my manager next to me at all times and taking care of 15 kids one summer. So it was just everything. It was like a math. It was like you put my whole life story in a blender and it was all occurring at one time. So it was just so cool to be on that journey and now to eventually fade out of coaching and get back into solely music. But as you've been out here,
We work the farm in the morning and then music comes second. So it's just been so full circle to have all that stuff go on. So now it's, you know, kind of after a while of, you know, grinding and, you do start to see the path. The path does start to reveal itself. And, you know, once you're able to go along that path confidently with your team, that's when themes, you know, my team being my wife, you know, my team being my, you know, my managers and help like that for music.
you're able to just, you know, kind of, kind of get everything focused back down to where you want to be. And that's just kind of how life goes, right? Life goes up and down like a roller coaster. And now it's like the older I get, the more I strive to just have it be a little tiny bump in the road as opposed to an emotional roller coaster. So I know that's a lot, but that's kind of, you know, the gist of the last, would say eight years of my life. So. I love how you put that, like all the ups and downs of life get thrown into this.
eventually it all blends together into something that makes some sense, right? A lot of people that I chat with feel like they're just picking up little breadcrumbs of experience and I mean myself included really like wondering how it's all going to add up. But then at some point, you know, like you described, it all just clicks into place and
about relying on others or having them rely on you. That's such a tricky thing and it stood out to me. It really puts our egos to the test, right? It's hard to ask for help and it's hard to trust someone sometimes with important things, especially when you are getting vulnerable and it's someone you care about deeply because you care about their feelings about you and I can totally picture it. You're driving, you're thinking about how to bring up this tough topic.
Jenny Dempsey (27:47.032)
to Gabby, I think it's natural to feel a bit uneasy and let your ego hold you back sometimes. So just kind of thinking through this, Zach, can you share a bit about a time when you had to ask Gabby for something big or when they had to lean on you, how did you push past that initial hesitation and kind of build that trust you needed to make it work? What really helped you get to the point where asking for help or relying
on someone felt like the right move. Can you talk about that? Yeah, I think there's a couple of factors that went into that. For me, is you're exactly right. think I, looking back, I wish I would have asked for help a lot more. I wish I would have been vulnerable enough to go, hey, even though, even going back to minor league baseball, I wish I would have had the courage to present myself to my boss as opposed to blindly working and said, hey,
what do you guys need me to work on so that I can get to this next step faster? And I think that is such a hard place to get to because you don't want to seem like you need help. know, like just because you're not, you they could put you on the fast track if you're just like you said, if that ego, if you can put your ego aside a little bit and say, hey, maybe I don't know what I'm doing, even though I'm athletic and strong and feel like I'm working my butt off, maybe it's not in the right direction. So
I think that had happened a few times, five or six times probably on a life scale. Like I said, just having my son and being like, dang, holy cow. And so I think that when I was going home to ask my wife about that exact moment, it was more like, I know she's gonna approve of it. Am I willing to do what it takes to make it happen?
And once again, I didn't ask for any help even in golf. Who would have known what had happened if I would have just put it all on me and thought, if I can give lessons for 100 bucks an hour, then everything will work out and it'll all be good. so I think even that was a testimony of like, yeah, maybe you're good with your wife. Like maybe you don't have to put those guards down for your wife because you guys are on the same page and you've gone through so much already.
Jenny Dempsey (30:14.388)
I wish I would have set a lot more feelers out. I wish I would have asked a lot more people to help me along the journey or collab more or help on that end where I always just, my default for so long was just putting my head down and doing the work myself. And all of that is great if you know exactly what you're doing. And I've never necessarily could pinpoint exactly what I was doing. So I think
The stuff that I learned from it was all the relationships that I made on the golf course. My producer now that I go and take all my music to is a golf head. And now I met him playing golf on the golf course. And now we can have business meetings on the golf course. And then we meet other people. We've so much golf with so many people. And you just go, wow. I would have never thought that because I never thought I was even going to make music until two years ago.
that when I met my producer as just a friend playing golf, that I would be in his studio a year and a half later, doing the stuff that means the most to me right now. So I think those are the things that life teaches you so much when you are in those shelled moments. And I say shelled because it's hardened, right? You just put your head down and you don't really know what to do, but you're not gonna make excuses because that doesn't help. So I think by being in that hardened shell,
phase, I also met some of the most important relationships in my life now. know, so such a double edged sword, putting your head down and going to work not looking and also being vulnerable to go. Well, it doesn't matter if I'm going the wrong way or not in the right direction. Doesn't you know, it's just spinning gears to spin gears is going to eventually be you're going to burn out, you know, so I think that was what was kind of the aha moment was, okay, I know this is going to be good with my wife, but
I wish I would have reached out and had more outlets to bounce ideas off of, to go how to get through pass instead of Zach's going to play golf, he's going to work his butt off. Once he passes the test, hopefully the company invests in him. That's just not what happened. It's nothing personal. everybody at work loved me. they were just like, no, we don't see that in our future. I'm like, okay, now what?
Jenny Dempsey (32:39.584)
So, so that's what's cool. You know, and then that's kind of that, that, that conversation was, you know, and Gabby also was able to go, yeah, but you did it. She's like, yeah, but you literally looked me in the face a year and a half ago and said, I'm going to go pro and golf. And you did what you said you were going to do, you know, so that in that hardened phase, I still also proved to the most important person on my team that I'm at least going to do what I said I'm going to do. And so this weird way.
I did accomplish a huge goal, but it doesn't mean that it was the path I was supposed to be on. Yeah, that's some really great self -reflection right there. And I think it really helps you see things from, you know, a broader point of view, like your whole team's view. It's not like, or, you know, it's like you're doing your own show sometimes, but you also know that you have a whole support network backing you up. And I know a lot of people I talk to, a lot of people I know,
myself, you know, it's scary to ask for help, even just a simple question because you don't want to seem weak or inexperienced or get rejected or get laughed at, you know, whatever it is. And it gets messy when we let that fear of what others might think hold us back. And honestly, if you just reach out for help, can actually strengthen relationships and show that you trust others. you know, and I've also found that
Asking for help not only gets you the support you need, but also gives that other person a chance to shine and share their knowledge. And it makes them feel like they're contributing and making a difference. And it's just good all around. I mean, I know I love it when someone asks me for help. I feel valued and connected. So yeah, does that resonate at all too? Well, and I think it's so nice now being in, I was never in the arts industry. Now that I'm in the art industry.
people are so much more willing to collaborate. Art is so, at least in my experience, I know in your furniture flipping that it's gotta be somewhat similar. I'm sure you have a nice community that you can share stuff with that doesn't put it down, that wants to see you grow, that loves to see you. So I think for me, that has been so refreshing from, I'm as competitive as they get, don't get me wrong, I love competition, but I never understood what it actually meant.
Jenny Dempsey (35:05.922)
to collaborate. I thought that collaborating was throwing an alley oop and someone else throws it down and the team scores two points. You know, it's like, no, it's like you said, both energies have something to bring to the table. And when those energies combine with each other and start firing ideas off of each other, you understand that you're accepted in that space. There's just something about that organic growth that happens in that moment that I haven't experienced in sports as opposed to now.
I don't know, don't know. intellectual property, guess you'd call it. Whatever ideas are that you bounce off of each other are just so, so much more rewarding on this end of the spectrum. That's all I can say, you know? yeah, absolutely. When I reach out to a fellow furniture flipper on Instagram and I'm asking them, like, what paint did you use? It's not just about getting the info. They'll share not only what paint they use, but also...
you know, how they applied it, what brush they used, tips and tricks they picked up, and maybe even a bit about their dog and something funny that happened on that day. I don't know, it's the human touch that builds real community. And it's amazing, you know, how simple this is, but how powerful these interactions can really turn into meaningful connections and collaborations, especially in the art world where there are so many brilliant ideas and...
talented people to connect with and speaking of art, I heard you got some music coming out soon. So, so exciting. Can you share a bit about the project and what you've been working on? Yeah, absolutely. You know, about a year, maybe two years ago now, just at two years, I had a buddy that hit me up and was like, hey, do you want to come jam? And you know, he's a heck of a guitar player and I knew that he was writing songs and
and him and his brother's names Ethan Davis and his brother Heath Davis. And they just hit me up and they're like, do you want to make some songs? And I was like, yeah, that would be cool. I'm into music right now. Like I'm having a blast. Let's get together and write. And we get together and write and all of a sudden we're like, man, this is better than average. We're like, this actually came out a lot better than we thought that it was going to be.
Jenny Dempsey (37:23.598)
Once again, I'm like after leaving the house with these guys after I think we played music for, I don't know, like 10 hours and we didn't have anything written, nothing done. And we came out of there with three songs for ideas. And it was just like, looked in the rear view and I went, am I going to go tell my wife that I'm going to be a music guy now? Sure enough I did. And, know, honestly, just those, those two guys in my life, you know, now I have this team of people around me that is just so.
involved in every aspect of the musical process from writing to making the music to promoting it to dropping it to talking to pitching to Spotify to doing all this. And we are all so immersed in this right now. And it's so cool because they're real estate guys. do, the biggest part of this whole thing was how are we going to make a living and still do this? And I think if you want to be a career flipper,
You need to, you know, if you don't know exactly what you're flipping to, have the job offer on the table with everything, the bells and whistles that you like. You have to understand that, you know, this stuff doesn't happen overnight. You know, it's like we had to look at each other and go, okay, what are the next steps that we can take to becoming more professional at this? And eventually you go, my gosh, I need to just take care of this, my life, my bills, my son, his schedule, my wife's schedule, all of these things that every
every father, every human has, to, now I'll do whatever it takes to get that. That's where I feel like my mindset of just putting my head down does work well. That's where it's like, whatever we gotta do to make this happen, now I'm in it for, I think just like you, right? I'm willing to work as hard as I can so that I can make this my career. I want to make this my career. And honestly,
The day that I can stop doing all this, well, I'll never stop because I love helping my wife out on the farm. But the day that you wake up and you go, I'm a full -time musician is the one that we're all waiting for. And until then, it's it's still my career. You know what I mean? Just because it hasn't changed my life financially doesn't mean that I'm taking it any less serious. It's just, what am I willing to do in this lane so that I can focus on this lane now? And I think that's such a healthy place to be because your brain needs that little bit of sacrifice also.
Jenny Dempsey (39:46.19)
It's not supposed to be this rise to the top. That's not how it works. There's valid plays and peaks. Once again, it's like the roller coaster. And I think having to really put your head down and get your priorities, one, locked in, two, organized, three, executed. I think that's what truly sets you free to be able to do that new career. And for me, that's just when I met those two guys that were willing to do the same thing, I love being on a team and it just went together like gears in a clock.
I find that visualizing my day, like down to the tiniest details, like what am I having for breakfast, you know, really helps me stay focused when I, you know, can picture myself living that life, living in those shoes and seeing what my day looks like. It's really motivating and it's like if I can clearly see where I want to be heading and how I'm gonna do it, like I already kind of have it.
like I'm already living it, which sounds kind of wacky, but like, I'm just way more willing to make the sacrifices to get there when I can picture it in my head. You know, it's like having a clear roadmap. makes, I don't know, it makes the whole journey kind of feel more doable and it keeps me on track. Where do think that comes from? Like, where do you think that like, you know, for me, mine was so competitive. Mine was just driven off of this guy over here might be working out. So I'm going to try to work out harder. Like in you, where would you say that that, that originates that feeling? you're flipping this.
Usually I'm the one asking the questions. Okay, I mean honestly, I am not competitive at all. I really shy away from competition. I think my drive comes from something deeper. I've seen a lot of people throughout my life really give up on their dreams, give up on themselves because they didn't believe they were worth it. Growing up,
I had a lot of people around me that had the you're not good enough mentality and I don't know, it stuck with me and so, and kind of became part of my core belief. So, you know, it's been a long journey to work through these feelings, lots of therapy, lots of, you know, support and realize that I actually am good enough. And sometimes I look back and think about all the things I sacrificed just to fit into what I thought.
Jenny Dempsey (42:12.386)
you know, I thought I should be. And it's heartbreaking. It's heartbreaking to remember, like for example, I gave up on music. I used to play and sing because I don't know, I didn't believe in myself. I was doing paid gigs in Philly and I just walked away from something I loved because I didn't think I was good enough. And I made a promise to myself over, you know, the past several years, I can't give up on myself again. I've seen what happens when you do.
And it's painful to think about the talented people from my past who gave up on themselves and what they could have done. And I want to push forward, not just for me, but honor their legacy in a way. And it's about showing that you can keep going. You can find success. It's going to be hard sometimes, but you can keep doing it. And some days are definitely tougher than others.
These old insecurities, you know, sneak back in and I'm questioning everything. I'm sobbing on the couch. There's times when I think, am I really good enough today? And I'm sure it's annoying for people around me, but then I remind myself that I can't go back to that place of burnout and self -doubt again. I've learned from that. I've had jobs where I felt like I was selling my soul and I'm determined to not go back to that either. And you know, what I'm doing now, like this has to work.
You know, I'm fully committed to making it happen. I'm curious what it's all gonna look like and it's a journey and I'm all in. Well, that just resonates so much with me because like I said, I mean, when I was 24 years old in the best shape of my whole entire life, throwing the hardest, I felt amazing. And someone looked right at me and was just like, you're not good enough. You know, see you later, go home. And it was just like, you know, I wasn't, you know, it one of those things where it just came out of nowhere. And you're absolutely right. That fueled me.
for so long that fueled me, that fueled my, I don't wanna say fueled, it hardened my heart. You know what I mean? Like it hardened my heart and definitely took a toll on me mentally and put me in a place that, you know, I've always told myself I was a very, very happy person, but if depression was going on, it was then, you know what I mean? And like probably went undiagnosed and what, but I was, know, and now everything is so much more.
Jenny Dempsey (44:31.352)
geared toward how I'm gonna feel about this in the future. Like, the work that I'm putting in today, I know is gonna make me feel, it's not a trophy, but a sense of accomplishment tomorrow. It's not gonna manifest in this physical form of like, here's your new Maserati. It's gonna manifest in the form of, you went to work every single day, now this is why it's paying off the way it is, and it's consistent, and it's real, and I can draw on those. It's not this.
the stimulated fake feeling. It's like, no, now I can look and see where I've been. And that's now I know where I'm going as opposed to, you know, being inspired by the future as opposed to being fueled by my past, you know, or my past failures. It's just so, so much more real and so much more day to day acceptable to me, you know, like my soul can accept the way that things are going now because
of the steps that I simplified took, on new challenges, you know, had to trial and error, but we're able to, we're able to get to that path. Like we said, that path will eventually reveal itself. And I think that's so refreshing that you just kind of shared the same type of feeling, you know, looking back at that person, I felt the same way. It's like, God, Lee, look at that pathetic person over there. I feel sorry for them. I wish I could give them a hug. I wish I could give younger me a big old hug and be like, dude, we got this. Don't worry. You know? So that was really cool to hear and such a cool, such a cool answer, you know?
Well, I appreciate you asking, you know, it's good stuff and it's our story and I don't know, for me it just comes down to, you know, things that I've learned and there were sad times and there were happy times mixed in and all the things from the past and, you know, now to focus on the present and, you the future and I'm just, really grateful that I had the motivation to keep going despite it all and
learn from it and I mean how many people go through this or are in it like right now and maybe I don't know haven't learned it yet or just it's really hard and so I just I applaud both of us you know for continuing to move forward and pave the path that is a little bit harder because like I guess I kind of picture it you know sometimes like
Jenny Dempsey (46:50.754)
There's one path. There's two in front of you. One path is super pretty. know, it's all the beautiful trees. It's well manicured and sidewalk that's already paved and there's flowers and garden beds and everything just looks so pretty and it's already done for you. And then there's this other path. You look the other way and it has, you know, broken fences and all the weeds and rocks and you know, you're going to have to go in there with your machete and clean it up. And that's.
one that we're choosing, you know? The one, that's the one because we get to go in there and we get to grab that shovel and we get to clean it up and pave it and make it look however we want and it's back -breaking work. It's sweaty, it's gross, but it's so rewarding. And a lot of the things that you've said throughout our talk, like it makes me think of this, you know?
And actually, okay, this is another question for you, Zach, kind of along these lines, you know, as we're paving this path, some of the things that you mentioned earlier, especially, you know, when you were coaching, how that feeling of making an impact on someone else's life impacted you? And I'm curious, are you still feeling that with music? Like, are you able to show this creative side and create from, or create in your own way?
you know, and putting things out there and music making an impact on people. And do you feel that that kind of came full circle? Is there something else there about that? I'm just curious if you're open to sharing a bit about it. absolutely. Well, and if you remember when you were out here, I played my first song for you and it was rap. I mean, it's rap rap, you know, and I would say that that was me trying again to just get into the industry any way possible, just by saying I can rap, I can do whatever. Like this is I'll do it.
And when we went, when we came and reflected on that and my manager actually came out here to write with me and just helped me put these first, this first EP out. And, you know, I think when he saw the life that we were living out here, he was like, you know, he's like, that's not really who you are. Like mentally that might be who you are. You might be starving inside. You might be, you know, he's like, but physically you're just an awesome dad that
Jenny Dempsey (49:12.534)
is working his butt off to provide this cool farm lifestyle with you and your wife. He's like, why don't you try country? And once he said that, those were all the things. I was just feeding my ego again. It never goes away. You're going to always have the same stuff come up. And the goal is to be more disciplined. More discipline doesn't mean that it doesn't come up. It means that you yield and make the decision that's better for your soul.
I think knowing when I thought about, maybe all those kids that I helped coach probably don't want to hear me talk about all this degrading stuff and, you know, be cooler than I am and maybe not be in the right situation with the right people at the wrong time. And to have that be from someone outside of me who cared about me, knew me, but truly was like able to see the good in me, you know, and to hear that from an outside source to just totally confirm now don't get me wrong.
I had no idea that we were going to transfer into the country lane. That was extremely foreign for me, just being a reggae hip hop guy. But once we were able to put our heads down and do it, it's like that opportunity came. And now I'm so proud of the stuff that we're putting out. We talked a little bit about the outlaw in my story. And the outlaw character that we're creating in this first album is a young guy. He's young me. He's young me that's just gung -ho, ready to go, and doing whatever.
And hopefully throughout his journey, these first songs that I'm writing about him become tales of, whoa, not to do it like this, you know, a reflective type of album to start things. And then we get into, all right, let's see who this guy is. So I think that it was like the ultimate full circle little question that you asked right there, because it just truly feeds. want to show, you know, you never want to lose that fire that you have in your youth, you know, and as we age, as we age every day, you're fighting to keep that flame, that hunger, that drive.
And once again, it becomes less sexy every day to just totally honor that thing. It's no, I have to submit to the discipline that's required to keep this flame alive. I don't need this flame to burn 10 feet high for the next 20 minutes. I need to keep these embers going for the next 10 years because something amazing can happen if we go about this the right way on the right path.
Jenny Dempsey (51:34.144)
You know, and it's, always going to have to check myself. You know, it's like, I was, I was an athlete. I do love me some me. I'm not going to lie. You know, it's like, that's like, that's the, that's the game mode that was put in us. But at the same time, I love me some Zeke. I love me some Gabby. I love me some, I love me some God. I love me some friends, you know, and there's so many other things that are, that are, that are so much more important that are, that you can still honor.
but still go forward, you know, with that daily discipline check, I think so. Well, Zach, I just want to say a huge thank you for being so open and real today on the show. Your transparency is refreshing and I know, I know our listeners don't really appreciate it. So I can't wait for everyone to hear your new song and connect with you. Where can they find you?
How can they reach out? So right now we have, let's see, six songs out on Spotify, on all streaming platforms, wherever you guys listen on, you can just type in Dando. It's Dando, D -A -N -D -O with a period at the end. And we are hoping to get our EP out in September. But right now we're going to release a song called Lonely Crow, which I had a blast writing with Ethan Davis and Heath Davis and my producer, Taylor. They just killed it over at Han Audio.
That's coming out on the 22nd. So we're really excited and we're looking to start doing some shows here and you know, kind of getting it going. So I think this next month and a half is going to be real big for us. So anybody that wants to go stream it and give us a couple streams will be greatly appreciated. Instagram just said Dando Music. I'm pretty sure we're at Dando Music on all platforms, but mostly Instagram for some reason the music world is just...
Ran through Instagram. People don't even email each other in the music world. They just hit you up on Instagram. So anytime on there, we have some stuff on YouTube, but mostly just Instagram. Everybody just feel free to say hi. mean, honestly, like that's the coolest part about doing all this stuff is all the people that you can meet. you know, if anybody, if anybody feels the need to connect and wants to share their story with me, if I can help out in any way, definitely reach out to me on those because this is a whole community. You know what I mean? Like I said, it feels so good when we're all in this together and rooting for each other and liking each other's stuff.
Jenny Dempsey (53:49.164)
and growing that way is always going to be so much more organic. So that's pretty dang cool. I'll tell you what, thank you so much for having me. This is amazing. This is so cool. You do what you do and a lot of good comes from listening to a lot of people talk. You know? Well, thank you, Zach. It was so cool to
I you so much. Just one last little piece that really stuck with me. got some. He's like, you'll never fail if you don't quit. Just keep going. And that's all I can say before we go is you're the only one. You get to decide when it's time to quit. You get to decide when it's time to be done. just whenever that goes, if anybody's out there listening, just know that you are the one that's in charge, not the world, not someone else.
Thanks for tuning in to this bonus episode of The Career Flipper. Be sure to connect with Zach using the links in the show notes.
and check out his song that comes out on Spotify August 22nd, 2024. If you enjoyed this episode, do me a favor and share it with a friend who could use a little boost of inspiration on their career journey. Read and review the show. It just helps a ton. And hitting that subscribe button means you'll get more awesome flipping stories like Zach's every week. Your support helps me connect with more career flippers and future career flippers to be, spreading all the good vibes and motivation we need on this
And if you're looking for a career flipping speaker for your event, want to sponsor the podcast, or just want to drop a line, say hi and share your story, pop over to thecareerflipper .com. I'd love to hear from you. Keep on your path, my friend. What's the best that could happen? Talk to you later this week.