Kyle Cooke on Saving Loverboy & Finding Financial Freedom

0:00This isn't the first time I felt completely misunderstood on national television. I understood you, brother. Done right, business, entrepreneurship, it'll not only bring you mental wealth, but it'll bring you joy. What's up, everybody? This is Rich Kleiman, and welcome to Mental Wealth, brought to you by Boardroom and Ally Bank. Today, we are here with entrepreneur, reality star, DJ, Kyle Cooke, and my co-host, head of money wellness at Ally Bank, Jack Howard. Welcome, guys. Thank you, thank you. Pleasure to be here. So you can't just say mental wealth for a guest and not define it. And only one person that I know can define it.

0:38So, Jack, please, will you give us an understanding of what mental wealth is? Yeah, what did I get myself into? So, Kyle, what you're getting yourself into is more than a bank account. It's more than numbers. It's more than your business. It's your relationship with money and how that relationship really fuels the joy that you have with money or not for your life today, tomorrow, and someday. So we're going to be vulnerable and we're going to talk about money. I'm ready for it. I do watch the show. I started watching like three, four years ago. I'm proud of that. I'm proud of that. You know, I think reality television used to be like the guilty pleasure.

1:13Now people are like, eh, it's just a pleasure. Yeah, I own it. I own it. It was clear to me, like amidst all the things that happen on reality TV, you have this like entrepreneurial gene. I can see it. Like it's the way your mind works. And that means things go well. That means things go badly. Where did that whole part of you come from? Pretty much early on, I had an interesting relationship with money just because I didn't have an allowance. My parents didn't really just go buy me random gifts and things. I pretty much had to work for everything. So that's starting with magic shows where I charged an admission, lemonade stands.

1:52So I was always hustling. I had landscape. I actually helped build a lake house one summer. And, you know, so it was very much like, you know, you only can spend what you earn, but you only can save what you earn, too. Entrepreneurship was, again, part of the hustle. And so, funny enough, when this casting call came about with Summer House, I looked at it as, like, an entrepreneurial endeavor because I could see it as a platform. It traces back to, you know, being an entrepreneur at a very early age. I ran a painting company. I sold knives. I mean, I did it all, including like, hey, if you can find a way to do something that you love and you're passionate about, like DJing.

2:32You know, so I just like to have multiple irons in the fire. So I'm very impressed by magic shows. We got to, we got to, come on now. Like to charge people for a magic show is amazing. You know, you got to do what you got to do. You got to do, right. But what fueled that? So when you think back to the magic shows and you said you sewed knives and all that, why? Why were you doing that? You know, my grandparents were very influential in my life. You know, I like to think my mom's dad is probably one of my biggest role models. I mean, he was incredibly self-made. His sisters helped, you know, work odd jobs to pool their money together so he could be the first person to go to college.

3:08He became a doctor. His work ethic and his drive. And he was frugal, too. But he was just playing. He played a big. He was a big influence. You know, so when I was a kid, you know, during these magic era, my magic era, I think that's kind of what sparked a lot of it. You know, my parents, it was very, you know, I'm from Manchester, New Hampshire. Even like, you know, the comfortable middle income households are nothing fancy, you know, three bedroom houses. And, you know, I grew up thinking like, yeah, if you had a two car garage, which we did not, like you're rich. And I was like, how do I get that two car garage?

3:46Yeah. So I think I just, I don't know, I think I was inspired very early on by just how my grandparents operated, how my parents operated. They were never flashy, never foolish with money. She asked my mom a question on the way up here, and she's like, you know, your dad and I have never had a single argument over money in 47 years. And I saw that firsthand. So when we talk about mental wealth, I want to always make that connection of the things that you learned growing up are impacting you and your business now, your entrepreneurship now, your relationship with money now. So as you think about your business now, we know you have Loverboy, you're, you know, with the reality TV, all of that.

4:28The things you learn from your grandparents, from your parents, how is that showing up now? And what did you learn? They would invest in what matters. When I think about my business, I mean, possibly, you know, looking back to a detriment, like when we were one of the fastest growing alcohol brands, I probably should have been over investing. But instead, I was just like, like, we're doing all this without having to spend the typical marketing budgets and go hire the sales team. But ultimately, the competition really heated up. Like we were innovators and kind of trendsetters within this kind of fourth category, better for you canned alcohol industry.

5:10When I dove into beverage alcohol, I kind of had to just be like a sponge and learn as fast as possible. It was during COVID. There was challenges that no one had experienced. I mean, there was a can shortage in 2020. So the U.S. was like 10 billion aluminum cans short of demand. so I just had to learn by doing at an like necessity but you know look I did go to business school I went to Babson it's the number one school for entrepreneurship but it's funny like we're almost taught there that like don't chase the venture capital like carrot on a stick type things you're ultimately you're like celebrating giving away your company and so I almost had this ingrained in my head.

5:54It's like, hey, if I don't need venture, don't raise it. But now I know that you raise money and during good times, you can ride out the bad. So I think that there was certain learning lessons. I mean, it's probably a whole other interview where it's like everything I've learned in one of the hardest consumer industries ever, which is alcohol. So life is good and bad. The business is good and bad, right? That's life. Yes. So when you think about where you are in the business right now, how are things going? I started staffing up and brought on some senior leadership and kind of took my eye off the ball in terms of like what we were spending on.

6:33And we got over our skis, you know, so it was almost like I started to invest in the team almost too late as things started to slip, as our distributors started to pay attention to bigger brands. you know that that led to us making some costly financial decisions the business was probably at its peak in 2022 so it's been challenging where we're at today i went from 30 employees to three three yeah um we are finally self-sustainable once again but have really had to pull back on our ability to support a nationwide distributor network and now we're just focusing on certain states and markets and just trying to position ourselves for the right strategic that sees, all right, we've already scaled in the consumer eye.

7:20That's the hardest part. And just trying to like find the right partner to kind of take us back to where we were and then some. Do you think that this, like I've read and I think people just kind of gossip about the idea that this scandal helped your business and it would make sense. And by the way, would have no problem with that because that's the gift and the curse of going on reality tv is that accurate i mean look if if anything as i was heading into divorce before all this craziness you know it was almost like people were like boycotting the brand just because like i'm the guy in the breakup as all this popularity and virality and desire to support the brand came about in the spring this industry is way too slow to react.

8:10But I was like, you know what? I mean, this is one way to support the brand is to run this kind of, this merch opportunity under the Loverboy umbrella. Going from 30 employees to three. Yeah. You got divorced. You... Still in that process. Okay, well, that process. You're in that process. I'm feeling stressed when you talk about it, right? And I think the piece about money and mental wealth is that oftentimes we just look at the numbers and we think about how we grow the business, but not looking at money holistically. How is it impacting your well-being? So when you think of your mental and physical health, when you think of your relationships, when you think of you as a person and the stress that you're carrying, what is your relationship with money like right now when you look at it through that lens?

8:58You know, when things are challenging, but you're on the up and up, it's exciting. You're like, hold on for the ride. And, you know, it's a thrill. That was basically 2019 through 2022. So it's certainly been an interesting journey sharing the good, the bad, and the ugly across every single aspect of my life. But in a weird way, it's freeing. Yeah. And again, that's just who I am. I am just like honest and transparent. And, you know, what you see is what you get. With a lot of people, when they don't do what you just did of being vulnerable and being transparent, then you have shame. And then the shame just makes you spiral even more.

9:42So kudos for you on that, of being transparent. And you probably helped people that watch the show who may be having financial struggles. You were an example for them of having grit and having resiliency. I don't know, good example. Well, there is some grit and resilience. Yeah, yeah, but you're still working at it, right? You didn't give up. So the other side of that is the resiliency to keep going to create a life where money brings you joy, where money is a tool to create the life that you want. So now that you're at this place with the business and really understanding how stressful it has been as you think to the future, what's next?

10:20What's next with money? What's next with the business? I mean, I mean, to the grit and resilience part, I mean, like that's a must if you have any entrepreneurial ambition whatsoever. And you were doing magic shows. Yes. Right. So I always tell people that have an entrepreneurial ambition, if you're not willing to like moonlight your idea and get it to a point where it actually might be a viable business. Like don't even consider quitting your job. don't consider giving up your revenue or you know how you currently pay your bills and and you know take into account your cost of living if you like if you're not willing to work into the night into the wee hours of the morning to try to get a start uh you know a startup or a business of yours like up off the ground then like you're not going to have what it takes down the road you know i'm starting to realize i need to find ways to you know generate wealth to kind of, you know, again, from a mental wealth perspective, I think of what it might unlock is freedom, flexibility, peace of mind.

11:23You know, I don't feel like I have that right now. Yes, I'm committed to Loverboy, but when I DJ, I have Loverboy at most of the venues. I'm trying to spread the awareness that way on the road, during the weekends in what would be my spare time. But I'm also getting paid. Yeah. And, you know, so from a brand partnership, a DJ and a TV show perspective, there are I'm kind of practicing what I preach, always have multiple revenue streams. As someone who managed DJs for a large portion of my career, you're all on a reality show. So everybody's there trying to be somewhat entrepreneurial. Yeah. That clearly didn't deter you.

12:02And it seems like you've really built a real DJ career for yourself. But it felt like it got boxed into like, that's just an irresponsible move. I mean, this isn't the first time I felt completely misunderstood on national television. I understood you, brother. You know, I realized that I hadn't done anything for myself in what felt like decades. And one thing that I absolutely love is music. And so when I blurted out, I want to be a DJ, it was long before I even had my first gig or knew how to DJ. But I was just like, you know what I would love to do, but I don't have the time is DJ. And then one thing led to another.

12:41A couple months later, my friend who managed a club here was like, dude, why don't you headline Halloween? I'm like, yeah, I just don't know how to do it. And then one thing led to another. So a yearning for passion that then led to something that gave me joy, then all of a sudden is a way to make a good living. And it's been kind of a wild 180. Rich, so I'm going to ask you a question, too, because I find with entrepreneurs or just people who are high achievers, it's like this 24-7 grind. We got to get to it. And you talked about joy and how you carved out space within music. Like, I got to run my business, but I got to create space for my joy also.

13:20So for both of you, Rich, what is your space for joy, like something you just own? and for you as you think about DJing, like how do you hold onto that even more and grow it while still trying to, you know, make the business grow? Yeah. The reason why I was selling toys was because that, I love doing it. Like I love that action. I love being around people. I love conversation. I love learning. I love experiencing. So the more I do in business, there's certain things that I take on. Like right now I'm building a restaurant in Austin. I'm looking at the bagel business space, which I already know is a complete like lotto ticket that I'm risking on this thing.

14:05But that's my like creative expression. And then like my business is my job. But even within my business, I found so much of that joy. So I get to socialize through work. I get to travel through work. So if I'm not doing that, it's just my family. And it's not cliche. It's just that like all the other things that I want and I can get, I get out of my work. And I want to call out for that, Kyle, is that you don't have to wait for joy, right? You can be in the middle of your alone and dealing with that and at the same time find joy in DJing. So when we think of mental wealth, it's definitely finding that balance of even within my work, what do I pull out in my work that brings me joy?

14:44Absolutely. And having that balance. I mean, I think entrepreneurship is my hobby. Yeah. So when you think about, do I need more hobbies? Yes, starting something. In terms of what's next, I'm constantly, the wheels are always turning. I'm always taking meetings, finding ways to just pump the brakes and smell the roses. And it's like, okay, if one aspect of my life is causing stress, what can I do? I work out a lot. Like for my mental wealth, I need like mental health, which ironically, you know, you get a lot from doing physical activities. Time to think. Yes. And so done right, business, entrepreneurship, it'll not only bring you mental wealth, but it'll bring you joy.

15:30The best nine years of my career, I always attribute to a point in my marriage and my life where we doubled down on our family, where we doubled down on each other, and where we both looked at each side of the street and said, what do we have to do to be better? She soared, I soared professionally. Looking back on it, those issues not being dealt with were at times like a black cloud over my entrepreneurial journey. So if I would call home and feel that energy, it impacted me during the day. Now, when you do my mass, when you double down, you aren't working together. No, no, no, no, not at all.

16:14I know that's the wrench you threw into it. I'm just clarifying. Yeah, we didn't work together. I was like, oh, yeah, there's a hope. But when you are, when you're married young and you're building a business and you're out and about and I was in the mix, she was with me, we were working together. You got to meet each other in the middle and meet each other halfway. And I think that like, I definitely prioritize business because I thought, well, hey, we're married. Like I'm committed. what more do I need to prove or show you? And so I think I lost sight that a relationship and marriage needs constant TLC.

16:56As an entrepreneur, there's no clocking in, clocking out. You're an energy. When you're an entrepreneur, it's like you're an energy guy. Yeah, like I can't turn off my brain. Yeah. But yeah. Rich, something you called out, a conversation you and your wife had is, what are we doing? What is the plan? how are we going to succeed with our family and also with money and that's a conversation that most people don't have when you think about loving money you gotta do it you gotta do it's just like go and you think that by working hard it's gonna make her happy and she wants something else did you guys ever have those conversations no okay yeah i mean like yeah i thought it was kind of obvious i was like i've been doing i've been doing startups since 20 and i just figured like now's the time, right, to be a workaholic because I don't have to be a dad.

17:45But I forgot that I also got to be a husband. So, I mean, I don't know if you had those conversations along the way, but I think that's like an absolute must. I thought I was having them because the, like you said, right, you just said, I assume she knew when she met me, I was this way. I did magic shows. Like you knew. I don't think she knew I was a magician. She knew you hustled. She knew you hustled. So like in my mind, I used to be like, you know, this is who I am. Like, this is what I have to do. I don't have any education. I don't have any finance to fall back on. Like it's what I do. But that's, I learned that that's not right.

18:22Like that, that actually wasn't accurate. Like that's how my brain was working. I needed to communicate it differently. And, and both people have to take like an inventory on themselves and they go, all right, we're doing this and we're moving forward. But it doesn't always work. And I actually have thought about how successful you may probably be the next five, 10 years because of this. It didn't work in your favor, right? Or in your marriage's favor. But you just went from that to finding out about your friend. The whole world knows. And now it's like, what? You know, I'm in debt. You know, I got divorced.

18:58You know, my friend is a snake. I said it. But at the same But at the same time, I'm free now and I'm going to build clearly. But you have to learn from those things. I really do think life is one long learning lesson. You got to always be learning personally, professionally. I've learned a lot from being on TV, watching myself back. I've learned a lot from kind of putting it all out there. I've learned a lot from kind of putting my neck on the line, taking chances. You know, I do kind of live by there, you know, there's no risk if there's no reward. I've taken many financial risks in my life just from a mental health standpoint.

19:34All right. So I'm going to give you something I want you to do for your next opportunity to date. A money date night. What is a money date night? I don't know. I like it, though. And you can do it, too. Let's do it. So we're going to have a money date night where we pick at least once per month, maybe twice per month. And we're going to talk about money stories because you both talked about your money stories. Do you know your wife's money story? Yeah. Yeah. OK. So these are things you have to know. I hope. Like, so understanding their money story and their beliefs. Because I think it's a great topic of understanding what is your money story?

20:06What are your beliefs? What brings you joy with money? Having those conversations in the beginning of your relationship and throughout. And checking in because the person you were, how long have you been married? Okay. 20 years? 23 years. All right. The person you were 20 years ago is very different than the person you are today. Oh, my God. And same thing for your wife. So although you may start out with a person, what they want and believe in can change, too, because we get to change. So in this money date night, you're checking in like, is this still what we believe in? Do we still have the same values and alignment with these things so that you stay on track?

20:42But it could be fun. I think oftentimes we make money such a heavy topic that people want to run from it. it makes relationships tough when it could be a lighter topic when we address it and make it a part of the joy in your life so money day night i like it i mean i think especially early on in relationship if you think something's going in that direction having those conversations up front you both these shows right you grew up in new hampshire both these shows now in the city that takes place in new york city and the hampton show um what is like being notable in new york and the access in New York been able to do for you?

21:20I mean, yeah, it's, I mean, I'm here today. I mean, look at the people you've already interviewed and the people that I'm sure have lined up. I mean, I feel very, very blessed to be here. From that perspective, in terms of how I like to utilize it, it's incredible. It's absolutely incredible. Like the things that I've been able to do and the doors that it's opened. I mean, I feel incredibly fortunate to keep doing what I'm doing. So aside from the DJing, I want to get back to the things that bring you joy. We know that it's the DJing. We know that we're going to, the business is going to grow.

21:50Yes. Putting that out in the universe. It's manifesting. It's manifesting. What are the other moments or experiences that you want to have as you think about the next 10 years? I realized a couple years ago that I hadn't gone on a vacation in several years. Like nothing. I know it's a little cliche, but I mean, one of the things that when I think about mental wealth is the ability, like I said, to have that flexibility and freedom to invest in the things that matter to you. And I just think that like seeing the world and like experiencing other cultures is something that I've done, but I want to do so much more.

22:21You said experiences and I want to close the loop here and say earlier you mentioned how your parents gave you experiences. So as you think about this relationship with money moving forward, it's so important to understand how those things show up now. And for you, the same thing that brings you joy when you were a kid to now is experiences. And don't lose that. Yeah, my grandmother, instead of passing on like a bigger inheritance, she was like, so my dad's side, she wanted to give our family and my uncle's family an experience. So she took us to a safari. And she took us to the Galapagos Islands.

22:58She took us to a dude ranch. And she, you know, made skiing a reality for us. So like having those experiences, I look back on that. Those are some of the most most memorable times in my life. And that, moving forward, I've got to carve out time for what brings me joy. Your prediction as an entrepreneur for where you think you can still take Loverboy? That's a great question. So we have so much potential. We are doing a lot of work to kind of reposition the brand kind of behind the scenes. My goal is if I find the right partner that understands the platform, the value of my customer base, and the fact that we do still have very differentiated products.

23:39is to once again bring Loverweight not only nationwide, but to some of our biggest fan bases abroad, which is Canada, Australia, and potentially the UK. All right, well, Jack, as always, incredible. Kyle, thank you so much for being open and honest. I foresee great things for you in the future. This is Rich Kleiman, Mental Wealth, Boardroom at Ally Bank. Thank you so much for tuning in and subscribing. We'll see you soon. For those listening in, if you're ready to tackle your mental wealth, you can visit ally.com backslash money roots where you'll find key resources to understand your relationship with money and tools to help you on your mental wealth journey.