00:00:00 - Casey Helmick
We basically had to work two jobs when we were selling our businesses. You know, you keep it going, because if you don't, it loses all its value and then also selling it and compiling numbers. And what I will say is, you can google things. You'll need to sell your business. Why not do all of those things today? Your business will be better for them anyways.

00:00:28 - Dana Kadwell
Welcome to Hustle and gather a podcast. The everyday entrepreneur to take the leap. I'm Dana.

00:00:33 - Courtney Hopper
And I'm Courtney.

00:00:34 - Dana Kadwell
And we are two sisters who have started multiple businesses together. And, yes, it is as messy as you think, because we know that starting a business isn't easy.

00:00:41 - Courtney Hopper
I mean, we've done it four times. And on this show, we talk about the ups and downs of the hustle and the reward at the end of the journey.

00:00:47 - Dana Kadwell
And this season, we're talking all about the messy middle.

00:00:50 - Courtney Hopper
You know, when you have to decide to either grow or scale your business, maybe even take a step back.

00:00:55 - Dana Kadwell
And today we're talking with Casey Helmick about how to know when it's time to sell your business. Casey is an expert in the podcasting space. He works alongside top voices of culture, bringing clarity and vision to their communication. Casey founded the Raleigh podcast company, which was successfully acquired, followed by the Converge podcast network, which also saw a successful acquisition. Currently, he serves as the president of Terra Firma, a division of the Austin based content capital. Casey, welcome to the show.

00:01:20 - Casey Helmick
Thanks for having me. You guys are good at that. It's like your sisters or something.

00:01:23 - Courtney Hopper
Yeah, we are sisters or something.

00:01:24 - Dana Kadwell
Yeah.

00:01:25 - Courtney Hopper
Sometimes it's just the something.

00:01:27 - Dana Kadwell
Yes. There's always lots of bouncing back from one another.

00:01:29 - Casey Helmick
Well, you made everything sound so awesome, but sometimes it's not. So I'm excited to chat with you.

00:01:33 - Dana Kadwell
Yeah.

00:01:34 - Courtney Hopper
Oh, yeah. Oh, yeah.

00:01:35 - Dana Kadwell
We've been in the middle multiple times. I think that's also one of the interesting parts about being in the messy middle, is sometimes you can get out of it, but then you get right back into it with other things.

00:01:43 - Casey Helmick
Yeah, we're crazy. We like the mud, don't we, entrepreneurs?

00:01:46 - Dana Kadwell
So I think that's true.

00:01:47 - Casey Helmick
Yeah.

00:01:47 - Courtney Hopper
I think there is something wrong with us. That is true. I haven't put my finger on it, but there is something.

00:01:53 - Dana Kadwell
Yeah. Some amount of, like, self loathing or.

00:01:55 - Courtney Hopper
Yeah. You know, it's almost like sadist or masochistic. You know what I mean? Is what it feels like. Yeah.

00:02:00 - Casey Helmick
I feel like I'm with my people, so.

00:02:02 - Courtney Hopper
Yeah. Welcome. Yeah.

00:02:04 - Dana Kadwell
Okay, well, why don't you start us and tell us a little bit about just how you got to where you are.

00:02:08 - Casey Helmick
Yeah. Yeah. It's actually kind of a different story. I keep waiting to run into somebody who's done the same path as me, but I was actually in nonprofit fundraising for a long time, and as a lot of people do, I got burnt out after I have a little bit of a baby face. But I spent a decent amount of time doing that, and it was great until it wasn't. And I had about three or four months where I was trying to figure out what to do next. And I had done some, dabbled in some podcasting at the tail end of that with a couple of the organizations I worked with. And I thought, well, maybe I'll give this a shot. This seems new and fresh and like something people want to do. Little did I know it was already 15 years old at that point. I've never really listened to a podcast before. I think we do that sometimes. We put our blinders on. Yeah. I decided I'd give myself about three months and try to build a little podcast network, which is the converge network. You talked about that. We just sold. That went well. And I started getting phone calls to make other shows, and I thought, well, let's follow this train and see where it goes. So that's how I ended up there. The converge network was literally me calling friends and saying, you're awesome on the Internet. You don't have a podcast. Can I make one for you? And let's see if we can make you some money with advertisers and take a shot on me. And some about six friends did, and we built a network out of it. And happy to share the story about the full story of how that ended up selling a few months ago, but that's sort of how I got into it.

00:03:38 - Courtney Hopper
Okay, nice.

00:03:39 - Dana Kadwell
And then, so what made you. Did you. Because you had two different companies. You had one and then sold it.

00:03:44 - Casey Helmick
So we started the network first because we didn't know we were going to start a production company. We just, let's make a network. Let's. I have these friends. We didn't even know what a network meant. We didn't even call it a network at the beginning. It was just six podcasters that we thought, maybe if you're too small to make this work on your own, maybe if we pool all you together, we can talk a sponsor into spending money with us, which that worked and worked and worked and worked. So that was what started it. And then other people in sort of adjacent content types, I guess word just started passing around that the podcasts were good and started calling and saying, can you make me a podcast? I might not want to be in your network, but I want my own show, and I'm willing to pay you to do that because you've shown that you can do that. So then we looked down, I think it was maybe two months into the project, and I thought, gosh, I'm making more money producing shows than running this network. So it all was kind of one company at that point, and with the same talent I would use to make the shows for the network, we just rolled over and started producing shows, and that grew right in the middle of COVID which was actually a really good time to start podcasting, because everybody was podcasting at that point. And I had a good friend of mine that I started talking to who's based in Austin, and she's in the book publishing industry, and she started sending me all these authors that were bored sitting at home. They didn't have anything to do. So maybe I should do a podcast. I said, I think you should. I think you should pay me to help you do that. And we looked down three or four months later, and it was like, gosh, half of your business is my business. Half of my business is your business. Maybe we should do this together. It seems like a lot of people who write books want to make podcasts and vice versa. So you'll see. I think you'll see a trend. For me, it's just sort of like, I'm not the most creative person in the world. You just look down what's next? When I was in nonprofit world, we started doing some podcasts for nonprofits while I was still in that industry. That's neat. Let's follow that train. And then you do some podcast stuff and look up, and it's like, well, people will pay you to produce shows. That's neat. Let's follow that train. You just keep kind of taking one step at a time. I don't. Sometimes I think I look at entrepreneurial friends I have around, even around town here, and they get so caught up, and, like, I have to dream up the perfect ten year plan for where we're going to go. It's like, maybe I'm just not smart enough to think that way. But anyways, that's sort of how we got to the network. And then production and then content capital is the company that we sort of merged everything together under that's based in Austin. I still live here in Raleigh, and we help people turn their content into capital. It's pretty simple concept. But one that we find a lot of companies aren't willing to truly help with. There's a lot of people that will help make your show, maybe some people that'll help try to grow it, grow the audience, but very few companies will actually kind of pony up and say, like, no, we're going to focus on how this could turn into a sponsorship or maybe you write a book one day and sell it to your audience or whatever the technique may be. So that's just sort of one step at a time. I might have gone a little quick there, but that's how we ended up from nonprofit to what we're doing now.

00:06:55 - Dana Kadwell
So timeline wise, like, so you started the network and then what was the timeline?

00:07:00 - Casey Helmick
So that was 2018, and then January 2021, we emerged it all together into content capital. So it was pretty quick.

00:07:09 - Dana Kadwell
Yeah, that was pretty quick.

00:07:10 - Casey Helmick
But the network ran for kind of independently for, well, I guess until a few months ago when we sold it, which we can get into in a little bit. But when we sold that network, it was, it had been all independent since then. So that would have been from 2018 to first part of 2024. Okay, I'm not good at math.

00:07:29 - Dana Kadwell
So five years, six years.

00:07:31 - Casey Helmick
Six years.

00:07:31 - Courtney Hopper
Six years, yeah. Wow. Okay.

00:07:33 - Dana Kadwell
Did you like being a CEO or an owner or.

00:07:37 - Casey Helmick
I wanted to like it.

00:07:38 - Dana Kadwell
Yeah.

00:07:39 - Courtney Hopper
Yeah, sure.

00:07:39 - Casey Helmick
And then payroll would hit every two weeks.

00:07:41 - Dana Kadwell
Yeah.

00:07:42 - Casey Helmick
Part of the merging everything together is. Our business partner in Austin had sold multiple companies. He's a really brilliant businessman and comes from kind of a CFO background. And so we thought, gosh, if we could have somebody to do the blocking and tackling of running a business, and we could be the salespeople and the talent developers and the podcast developers. That's what we like. So it's been good. We've been doing that together since January 2020. So this is our, I dug my hole here third year, three and a half years in, and it's been great. He, he's really picked up on the parts of being CEO that he told me in the early days when we were talking about merging. I don't know if anybody here is sports people, but there's a, there's a season of when you're in youth sports. For most sports, I'll just use baseball because that's what I grew up playing, playing. And you sort of have to decide, am I going to be a pitcher or a hitter? Like, you have to pick your specialty. And we were talking about that as I was sharing my struggle of being CEO, which sounds funny because it was just such a small company at that point. And he said, I think you're at the stage where you sort of, you can't do all that. You got to be a pitcher, you got to be a hitter. You got to sort of pick what your specialty is going to be. And since then, we've grown, we've doubled in size every year. And I think a lot of it is because being CEO is a great idea until you look down two or three months in and you're exhausted from doing the six tasks that you're not great at or that don't bring you life. And I think what that means is that I'm an entrepreneur, which sometimes we confuse those two things. Right?

00:09:20 - Dana Kadwell
Yeah, no, I think that's totally true. I think very few entrepreneurs are great CEO's.

00:09:26 - Casey Helmick
They can be. I think you can be initially because they're still that big. Like the zero to one problem. I can bring something from it doesn't exist to it exists, but there's a point when it exists and it's going to keep existing, and that's when I'm.

00:09:40 - Courtney Hopper
Out and you're like, oh, fine.

00:09:41 - Casey Helmick
And we're definitely there. Yeah, we're definitely there at the stage where it's like, okay, this will keep going. If I knock on wood. I was walking here to get, if I get hit by a bus tomorrow, it'll keep going. Okay, that's probably the litmus test of I shouldn't be the full CEO of this anymore. Somebody can probably optimize this. And then on the flip, I looked at this guy who's brilliant, who's helping us put this company together, and I kept waiting for him. He'll probably see this at some point and call me and say, why'd you say that? But it's true. Kept waiting for him to be the visionary of our company. Like, create the new, what's the next? And that's not him either. Yeah. Like, to expect that because he was kind of at the highest point of the company. He's acting as CEO and doing a great job at that. Where's the vision? But he's a CFO. He's like, how do we take the next step and keep making money doing this and growing it? So I would look over the first few months of this new merged together company and think, okay, when are you going to tell me what? And it was never going to come. And I looked over at him at one point, I thought, I've got a big idea. Can I share it with you? I think we should be doing this. And he's like, okay, here's all the ten things we need to do to fix it. I'm like, this feels backwards still, but that's because I'm the entrepreneur and a vision person, and he's the practical, like, run the business, operate it person, and that's okay. Just kind of. Kind of find your seat on the bus.

00:11:01 - Dana Kadwell
Right, right. Yeah. I love that. I think that's so true. It's one of those things that is really hard, I think, as a small business entrepreneur, to recognize that you aren't actually what's best for your company. There's. I don't know if it's pride. I don't know if it's a fear. I don't really know. But it. And it really is when you finally realize that, like, my. My job and what I'm really good at is creating something, you know, making it exist. Right. It is that visionary, but it isn't. A lot of times, it's not the day to day. It's not the going through the motions of how to run a business.

00:11:38 - Casey Helmick
And it feels like that's a fail. Like, to admit that it's, like, hope I don't put that on a podcast someday. But, like, I. It took me a while to get over that. It may be pride. I'm not sure. I think it's because I thought the peak, whatever we call that the CEO or whatever that role is, was supposed to be able to handle. Like, you pick up jobs along that journey. Right. You start. When I started, I was talent acquisition for the network. Then I was the ad salesperson. Then I was the producer for the shows. And you keep adding all those things to your toolkit, and then you look down. I did. And I was CEO of this company, and then I also was still producer, ad salesperson. Right. And so to get to that point and to give anything up was so counter to the process I took to get there. It's like, if I give anything up, won't it wreck the momentum we have? Because what got me here was to add all these things to my toolkit.

00:12:34 - Dana Kadwell
Yeah.

00:12:35 - Casey Helmick
So maybe talking it through with you guys, it's not. It didn't. Didn't feel prideful at the time. I would have been happy for somebody to come in and run as I was. It felt like if I do this, it will destroy the business because the business is working, because I'm doing all these things. Yeah, I guess now I'll reverse my reverse, which is. Maybe that is pride.

00:12:58 - Courtney Hopper
If it's pride.

00:12:59 - Dana Kadwell
No, I think we're sold a bill of lies. Personally, I remember it was year two of us opening the venue, and my husband had sent me this video, and it was. I think I said this story before, but it's of a man. He developed a razor for bald people, okay, who would like to shave their head, right? And it's like you put it in your fingers and it's curved and it's like this. So you're not using like, a regular razor. It helps it so you have less, like, you know, head rash or, like, cut yourself or whatever. And it's this whole story. And he had hired some people to go out and sell this razor, and when they came back, he had sold the most as the owner, he went in and he had sold the most, and everyone else had barely made what they were supposed to do that day. And the whole premise of the story was that nobody is going to sell your business like you. Nobody's going to love your business like you. Nobody is going to be as dedicated. And I, and that's what we were told for so long. As an entrepreneur, nobody can do what you do. Nobody's going to give the care and the effort and the energy to it other than you. And I believed it for so long. And so I held on to those truths and those values of, like, well, if I don't do this, it's going.

00:14:01 - Casey Helmick
To fall apart, right?

00:14:03 - Dana Kadwell
If I hire someone, they're not going to care enough about it. They're not going to value enough, they're not going to sell it well enough because that's what we're told. Like, that's, like, literally, like class one of entrepreneur. No one's going to sell your business like, you're going to sell your business. And it's just such, I actually think it's a lie. I think it's really did a lot of damage.

00:14:20 - Courtney Hopper
I think that we, like, discount the mental aspect and the fortitude and the talent it takes to create something. Like, to be able to say, like, hey, I have this vision, and here's how I think it can come to fruition. And obviously, you have players along the way. You're like, I need you on my team, and you and my team and you on my team, they're going to make this happen, but we're going to do this, this and this, and then this is going to happen. And then this is going to happen. I think for me, it took me a long time to admit that I really, even though I owned a planning company, and that's like, how we got started. I hated planning. Like, I was the worst on our team. Like, my skills did not align with that particular role. But what I did love was watching my business grow. And, like, in the beginning, I had to love planning to watch my business grow. I was the business. Dana was the business. That's how we were making money. Right. And that was fine, but it became very, very quickly. Like, in a few years, I realized, okay, like, I can bring in somebody else, and I can make a portion of what I'm making on that, and I can focus a little bit more on this. And it took me a long time to come to terms with the fact that, like, yes, I own a planning company, and, yes, I hate planning. Right. But I do love the business. I love hiring people. I love being able to recognize more talented people than I am that are there implementing my vision for my company. Do you know what I'm saying? But I don't think it's necessarily pride, but I think that it's, like, some level of self actualization. Self actualization that you have to come to to realize, yes, oh, I'm just an entrepreneur. Right. And also, I feel like, to your point, like, I really resonated with your, like, hey, this is kind of off and running, and this means I might need to just, like, peace out of some of this. This is exactly how I feel. I'm like, okay, it's off and running. It can do its own thing. It's time to piece out what's the.

00:16:00 - Casey Helmick
Next thing I learned. The goal that I've started to set with stuff that I make now is I want to make it so great that people want to outsell me and want to come in and be a part of it. And that changes the kind of things I make. I was reading a book last night, and it was breaking down these kind of life theories. I don't read books like this very often, but some reason I was reading it last night, and the guy was talking, he had this phrase that said, what hooks your eye multiplies. And what he was trying to say is what you're focused on. We'll just keep making more and more and more of it. And I. As you were talking, it made me think that what my eye was hooked on in those early stages was, like, staying alive.

00:16:44 - Courtney Hopper
Yeah, you have to do that.

00:16:45 - Casey Helmick
Trying to build something that I didn't have to work 80 hours to do every week. You know, it's these basic, like, survival things. And then it shifted to, okay, it's. It's going now. I need to focus on kind of creating new, bolting new things on so that it can continue to grow and thrive and flourish. And I never once had my eye hooked on how can I make something that is so exciting and so clear and concise and easy for people to come off their road and sort of onboard into mine if they want to? Not that I would have to beg somebody to come operate it for me or find a CEO, but that people would see it and think, what do I have to do to earn equity in what you're doing? Or what do I have to do to become a partner or to operate that? That's a whole different level of goal setting that I would have never comprehended. And maybe it took me having a few wins to see, like, I can make something, and I can make something so awesome that people want to come in and be a part of it. Now I don't have to recruit employees as hard. I don't have to find partners or investors or. I just think that's sort of become phase two for me is before I even start the zero to one making process, do I believe that I could do this so well that one day somebody's gonna try to push me out? Not that I'm gonna have to, like, step out on my own, but that somebody's gonna say, you're not the best at this. What if we did this and this and this, and I'll give you that for equity, or I'll buy into the business or it. I see mentors of mine thinking that way now, and, okay, that's a different set of goals I wasn't ready for, but here we go. And it's. I haven't been down that road yet. That's one that I'm starting. The process of walking down is making something that one day somebody would push me out of that. Like, it's okay to admit, you know, everything.

00:18:31 - Dana Kadwell
So it's like, it's almost starting with an exit strategy.

00:18:35 - Casey Helmick
Yeah. Yeah.

00:18:36 - Dana Kadwell
Like, which I think is so important for entrepreneurs in general to have that exit strategy.

00:18:39 - Courtney Hopper
We never did.

00:18:40 - Dana Kadwell
And we never did.

00:18:41 - Courtney Hopper
Yeah.

00:18:41 - Dana Kadwell
So. But, yeah, but I like that.

00:18:44 - Courtney Hopper
Let's talk a little bit about that, because I think, obviously, we're talking about time to, like, sell a business. And, like, I'm not gonna lie, and I haven't even said this out loud today. This sounds so appealing to me all the time. Like, all the time.

00:18:53 - Dana Kadwell
I'm like, it's not shocking. She says it all the time. She says, just sell it.

00:18:56 - Courtney Hopper
Just burn it down. Burn it down.

00:18:59 - Dana Kadwell
Is more insurance money.

00:19:00 - Courtney Hopper
Not that we're going to burn it down. We're not going to burn it down and they're not going to pay me enough. But I'm like, what is this worth? And then I start doing the math of even at a reasonable interest rate, what's that in the bank? What kind of capital we have to start the next thing. It is a dangerous game. The life of that looks appealing. Let's talk about that. What are some of those? Maybe you're going to tell me this is one of the key indicators. What are the key indicators that signal it might be time for you to consider exiting your business?

00:19:28 - Casey Helmick
I feel a little under available to answer that question.

00:19:35 - Courtney Hopper
Under available?

00:19:36 - Casey Helmick
Yeah. Well, I've only done this a few times. I know people have done this hundreds of times. I think, gosh, you might want to ask them, but from my early perspective, first of all, your businesses were some whatever, somebody's going to pay for it, right?

00:19:48 - Dana Kadwell
Right.

00:19:48 - Casey Helmick
And you can do all the multiples and excel sheets and. But at the end of the day, it's worth what? And by the way, that may be a good thing. It may be more than what people tell you it's worth. But I think I started that process when we started looking at selling the network. Who would have a stronger, better, faster business if this was part of their world? Because I think that business owners are probably more likely to buy the things we have than I, Joe off the street, who's trying to leave his nine to five. Now, there's always circumstances that can prove me wrong there, but I started the process thinking about what other businesses exist that would want this and that would be stronger and what would it be worth to them. And the trick there is that every business owner is going to think they can do better job than you can. So it's not just worth what it's worth, it's worth what they think it's worth when they plug themselves into it. And so I think that gives you a little bit of extra leverage to be thinking about as far as when to sell. I think the worst time to sell is when you're burnt out and when you're probably, it's I trying to not read too deeply into your mindset, but you know, like, oh, it's been a tough day, let's just get rid of this thing and start over on something new. That's probably I haven't found that's the best time to sell.

00:21:00 - Courtney Hopper
Sure.

00:21:00 - Casey Helmick
We started the process of selling our things when we had a new thing that we were super excited about, and we felt like the old thing was gonna slow us down. But again, that was just one perspective of one company. Our network was great, but it was the only. We looked at the portfolio of things we did and said, this one's not like the others. Everything else we were doing, we were paid more to do. We had to work with far less people to execute it. We were doing far less, like, podcast sponsorship deals than we have in any of our other business. So we just looked at and thought, this is like kind of the not ugly duckling. I guess I could say that now that it's sold, but that's what it was in our portfolio, and we thought, somebody else will find and see more value in this than even we do as the owners of it. And so I don't know if that's helpful perspective if you're looking down and thinking, I have a big dream. And not just that, I need the money from the first thing to make the new dream happen, but I'm already starting putting in process the new dream. That's how much I believe in it for us. We are launching a research division of our company that helps people before they even start writing a book or making things that they can do some market research on what people even want from them. In order to do that, we needed some more capacity on our team, but we had already started building that new company before we ever even thought to sell. And once we got to a certain stage, we thought, gosh, it would be nice to not spend 20 hours a week on this when we think this could be bigger. I think making, again, back to my silly, or that guy's silly example of, like, what hooks your eye multiplies. If you're only thinking about money in the process of selling, if that's what's kind of hooked, you're gonna. I think you're gonna probably fail. Like, there's never enough money, right? And after selling two companies now, like, when you add up the hours it takes to sell a company and the effort and the follow through with it, like, I almost think, did I lose money on this? You know, even if the deal was great, you know, with all the emotional toll that goes into it, we basically had to work two jobs when we were selling our businesses. You know, you keep it going, because if you don't, it loses all its value. And then also selling it and compiling numbers. And what I will say is, the helpful advice I give people who are thinking about this is, clean up your books now. Yeah, it's the number one thing I talked to, I talked to a number of people who are thinking about selling. I said, how are your books? Have you been keeping up with them? Not that there's something nebulous that's going on with them, but like, go ahead and go through the process of having a p and l ready for the last two or three years. Like have it prepared. Because when you get to that place and you find somebody who may want to buy, if you've already done the prep work, not only is it going to be easier on you, but they're going to be like, oh, they have their act together. I can trust this business. I'm ready. So you can google things. You'll need to sell your business. Why not do all of those things today? Your business will be better for them anyways. Like if you have a clean p and l, for instance, you'll know where I'm making and losing money more accurately now than I did before I had that. Some people may listening, may think, well, of course, I already have that. Well, good on you, you're ahead. But most entrepreneurs are busy building, not keeping a clean house.

00:24:12 - Courtney Hopper
Yeah.

00:24:13 - Casey Helmick
And that we had a relatively clean house. But I spent a couple weeks like combing through everything, making sure everything was right, making sure all our vendors were paid, just going through and making sure every duck was in a row. And I was thinking halfway through that process, I should have been doing this. It should have been done. This would not be a stressful process. So almost fake out like, you're going to sell your business this month, if you're listening and go through the process, and that may also help you identify am I ready to sell this or not? Because looking down at the actual numbers and the time you're putting in, you may think this was hard yesterday, but when I'm looking at the numbers, we are making some money doing this, or I really do love these contractors that work for me, and maybe we can build more in this area. So I don't think I answered your question perfectly, but those are some of the things we processed.

00:25:02 - Dana Kadwell
Was there any emotion attached to it.

00:25:05 - Casey Helmick
For you with the podcast network? Yes. Cause it was the first thing with everything else. I'm fully over the hump of I'm a creator, I make things, which means I can't hold on to a lot of stuff. A true entrepreneur has to have at least one hand open to build something. And I was holding on to so much at that time. I know now that I'm gonna constantly have to give up things. And I trust that whatever goes on upstairs, like, I'm gonna be able to invent something new tomorrow, and it's gonna be better or worse, but it's gonna be something, and then we'll do the next thing. But the network was a lot of relationship. I mean, that's back to 2018, and it was a lot of people calling and saying, I know you've been doing this with me for five years. What would you think if I sold this? Would you keep. You know, it's tricky with a network because I don't own, like, if you're a part of. If this podcast is part of a network, you still own it.

00:26:04 - Courtney Hopper
Yeah.

00:26:05 - Casey Helmick
So how do you sell a network that you don't own the shows within it? So, really what we sold was we sold the new buyer access to a number of downloads and impressions and relationship, which is why I think that was a little more emotional. Yeah. I'm promising you that I'm gonna make you guys friends, you know, which end.

00:26:26 - Dana Kadwell
Very badly, you know?

00:26:27 - Courtney Hopper
Yeah.

00:26:28 - Casey Helmick
Yeah. So far, so good. But, yes, you're very right.

00:26:31 - Dana Kadwell
Yeah, no, I think that's very true. And sometimes it is hard when it's not tangible things to sell. And I think that's a lot of, like, you know, we've had a lot of conversation. Well, I've had a lot of conversations, which has not gone very far, about selling the planning side of our company. But a lot of that is, yeah, you're selling clients, but you're selling relationships with venues and partners and saying, please continue to have them on your list, even though we're no longer, like, running it or owning it or whatever. It is definitely a very different mindset.

00:27:03 - Casey Helmick
For it, which I think that was a good test for me. With the network sale, which I can't share all the details of. With the network sale, we are still linked with the buyer. We don't work for them. But essentially, what we set up was a referral agreement. We go out and find a new podcasts that we think would fit in the network that I built, and if we do that, then we are compensated for that. And if I had felt like, nope, I'm done, I just want it to be gone, I don't know that I would have sold it. Cause I think I would have felt like I'm selling this out of desperation, which means somewhere along the way, this is not gonna be good. But going through the process with the new buyer, we knew we wanted to be linked with them. They were a good group. We loved our talent that we had in the network, it made sense. And then we also wanted to make money if we were going to be working. So we had to set up that agreement. But I think if you go through the process and you're, you know, sometimes you have to sell because of life circumstance, but if you can keep from being that sort of desperate, I'm done. It may be helpful to go through the process of thinking, what could I still do to make money on this network that I started and believe in? How is there a way for me to still be a part of it? And the buyer was, like, ecstatic. Like, if you want, you know this world better than we do, if you'll keep bringing talent, the network's gonna grow, and we'll make more money. That's a no brainer.

00:28:21 - Courtney Hopper
Yeah.

00:28:22 - Casey Helmick
So that may be a good test to run through, even if it doesn't come to fruition, is would I still want to be a part of this in the new, and what would that look like? And maybe, like, for us, it's been a huge win. We still know all these people who want to be a part of this podcast network, and we're thrilled to connect the dots there and build relationship, and we get paid to do that. It's, like, all the fun part of why we started it in the first place.

00:28:47 - Dana Kadwell
Yeah.

00:28:48 - Courtney Hopper
Nice.

00:28:48 - Dana Kadwell
It's like a win win.

00:28:49 - Casey Helmick
Yeah, for sure.

00:28:51 - Dana Kadwell
Yeah. I think that's super interesting because I think that. I think there are certain businesses where you have to almost sell it and walk away.

00:29:00 - Casey Helmick
Sure.

00:29:01 - Dana Kadwell
And I think probably, and I also think depends on the entrepreneur and the person who owned it. But there's certain parts of it that I think for me personally, like, thinking about, like, my planning company, for example, if we were to sell that, like, I don't know if I could ever be involved in it. Cause I would never agree with how they ran it. Like, I'd always be like, I can't. Like, I don't really. Cause I have very strong feelings about, like, I don't know how the company should be ran in a lot of ways. Like, when this was, like, 2021, we had just gotten back from engage, which was, like, this big conference. I told Courtney, I was, like, the thing I kept hearing over and over again was we had to let C and d go, which is our planning company, and, like, had to let it go. It's not serving us. It's, like, consuming our time. And for me, I loved planning. Like, I actually loved the planning side of it, but, like, I loved it so much that it was all consuming. Right like, it just. I couldn't do anything else. Like, I was very tunnel vision when it came to it. And so, and I, we talked about selling it, and Courtney was just like, no, I don't want to do it. So then I was like, then I washed my hands clean, and she did. I was like, I don't want to go to another event. I don't want to be a part of it. I don't even want to have a conversation. And there's still times, like, I'll hear because we're still business partners and obviously in it, and so there will be some things that is said, and I'm just like, I could just feel, like, my blood boiling. I'm like, I just can't even be involved in this anymore.

00:30:15 - Courtney Hopper
I just need to walk away.

00:30:16 - Dana Kadwell
I'm just walking away. I'm not going to come in. You do your own thing because it's just, you know, and, like, it's tough. It's tough being on the sidelines and watching something that you've built. And when I think about C and D, like, I know we built it together. Like, don't get me wrong, but I felt like it was so much of my soul in that company that I couldn't watch it anymore.

00:30:36 - Casey Helmick
And that's so what I was saying earlier about wanting to build something so great that other people would want to be involved with it. I think that's the challenge I felt selling the network is, have I built something that I really like, or have I built something that other people can see? Oh, my gosh. If we did this and move this and shifted this, and that's a hard place to be when you're selling because people are gonna believe they can shift and adapt things, and that might have not been in alignment with, you know, I'll give you a good example. With this network, there's already been a couple shows added to the network that are incredible shows, but would not have been added if I was overseeing it. Totally. But I'm so excited that things are being added to it and it's growing and thriving and flourishing. I may not agree perfectly with the pick, but I'm thrilled. I have to be okay. Knowing I'm the starter and it's gonna. It's like a plant. Like, it's gonna grow under someone else's, you know, ownership. And maybe I would have put it in this window and gotten it this much, but that's not my job. Like, my job in the world is to start things, not to grow them in that way. And that's not gonna be for everybody. That's for me. So some of the emotion, it's been a healthy process for me because I've, like, wiping my hands clean of it wasn't done out of frustration. It was done out of like, yes, I'm doing my purpose in the world. I made something. People are being helped by it. Let me go make something else so other people can be helped by that.

00:32:02 - Dana Kadwell
I love that. I think it's such, such an interesting thing to think through and, like, and I feel like the more in business, the more we have been in business, the more I can get to that point. And I think when you are a seasoned business person, you can recognize that business is what it is. It's seasonal, it's four time. Like, it's not the end all, be all. And so there's definitely things where I'm like, oh, like, we can start this, and maybe we aren't the ones to nurture it and grow it. We're just meant to get it, you know, sprouted essentially, and then hand it off to somebody else. That's really interesting.

00:32:32 - Courtney Hopper
Yeah, I love that.

00:32:34 - Dana Kadwell
I love the visual.

00:32:34 - Casey Helmick
I'm an optimist, too, by the way. So there are still nights when I sit at home and think, oh, why are we doing it that way? Or why that? Or. But here in this setting, I'll say there's a brighter side to it also. Like, you have to take a step back and think, it doesn't matter. There's a lot of other world I can go thrive and flourish and live in, and that thing's going to grow or it's not going to grow. And it was a big thing for us, as we also were very zoomed in on our acquisitions of, we would not sign a non compete. We wanted the ability to go make other things, because I have no idea what the next idea is going to be. And so the buyer for us had to be okay with us existing in the world still. And I think that's important for people to think through. I've heard of a few entrepreneurs who are so anxious to sell, they would have signed anything to sell it away. And we just weren't willing to sell it to somebody that said, you can't do this and this and this and this. Even if it was for a short time, we wanted partners that knew who we were and were excited about the kind of people we were and trusted us not to trample on them and that we would honor that relationship. But I think that if you're an entrepreneur, if you're resonating with the way we're talking and you're listening to this and you're an entrepreneur, don't be so desperate to sell that you're willing to give your future away, because, again, I feel okay with them taking things in different directions if I still have the ability to do what I exist to do. But if they've hurt me in both of those ways, I bet I'd be like, maybe not even here on this podcast. I'd probably be crying in the pain.

00:34:09 - Dana Kadwell
Well, it's interesting. Cause you said early on, like, don't sell. Like, when you're burnt out. And I think almost, too, is, like, not selling when you. When it's murky, like, your future is murky. Like, there's this point when you. I feel like it's like you're in. You're in the messy middle, right? And you're like, okay, like, do. I can see there's some clarity. Like, I can see that this isn't my passion anymore, right? Or this isn't what I feel like I should be doing. Like, I should be doing something else that maybe you don't have a very clear vision of what that is, but you know that, like, you can't shut doors, whereas I feel like a lot of people go through. You know, I've had some friends that have sold businesses and have, like, either shut down businesses, and it has been in this just total burnout desperation, like, and where they can't even see the next step. Like, they can't see their future. So they're like, I don't even care, because I'm, like, so out of it. Like, I don't even. I don't even care. Like, I'm never even gonna be in this industry again. Peace out. Walk away. You know? Which is so damaging, I think.

00:35:08 - Courtney Hopper
See, I feel like I'd wanna sell at the top. I'm like, hey, we're thriving. Like, we're kicking ass and taking names, and we're like, let's exit now. We're gonna get the most money for it, and let's move on to the next thing. I think we should end this with, like, you might be an entrepreneur if it's like, you might be an entrepreneur if the idea of doing what you're doing right now in five years terrifies you. If I'm stuck here in five years, even in a business that I love and that's thriving, that's making money, it's paying my bills, and it's creating my future, I still don't want it to be.

00:35:36 - Casey Helmick
That's the reason we're wacky, because our biggest fear is it worked.

00:35:40 - Dana Kadwell
Yeah. Yeah.

00:35:41 - Courtney Hopper
And you're like, wow, I'm stuck on this treadmill right here, and it's too good to walk away from, but yet I have so many other ideas. But it's, like, kind of figuring out and, like, you know, we've kind of worked around that a little bit. Like, for the Bradford, we have a coo that's in the middle of it and kind of is the one that's in the trenches and doing the things, and we're not completely removed. I hope to be more removed as the year goes on to. But it's like, all right, you know, that's a good, like, kind of middle ground where, you know, I can focus on this and focus on that and focus on this. But I think it's a whole different mindset, honestly. And I thought I was weird for a very long time. Like, I did not feel like there was other people who, like, felt this way. And, like, you're kind of taught growing up in this society, especially, like, eighties and nineties, where you're, like, security and that 30 year job, and you should be doing the same thing. Cause that's what's best for your family, and that's. And that's what you should strive for. So it goes against everything that you're taught. Like, when they ask you when you're ten, what do you want to be when you grow up? And you're like, I guess I'm going to be this. And I think, what a ridiculous question to ask a ten year old. What do you want to be when you grow up and meet people along the way who've had all of these past lives in the same life? And I have so much admiration for them. Wow, way to reinvent yourself 30 times over and just pursue your passion. But it goes against what we're taught. So I think it's kind of, like working out. I think that's one of the struggles with, like, what you're talking about when you're like, hey, let me let go of this aspect of who I am, this aspect of who I am, and this aspect of who I am, even though I'm trying to manage all of those things, it's like you gotta let go of those past iterations to be able to grow into the next one.

00:37:11 - Casey Helmick
I'll tell you one thing I learned. I just happen to fall into a personality that is very nice to people. I just. I struggle to be. Yeah, pretty aggressive towards people. If you're an entrepreneur, you should be really nice to your competitors because likely that you're going to need them at some point to buy you out, to merge. And I don't think that's talked about quite enough. If you're a true starter and not a continuer or finisher, the people that are going to pick up your baby and carry it into toddler or teenage years are probably going to be the people that you're competing against. And I was just thinking as you guys were talking, that if you're in the burnout stage, you might listen to this and be frustrated. Well, what are my other options? I'm burnt out. The option is to sort of do what I did, like pick up the phone and talk to relationships you have that are in the industry you're in, and start discussions, not necessarily even about a buyout, but have you faced this? What are you, how did you process it? And if you've been kind to people along the way, they'll probably share things with you. And that's really how we merged our companies is me and a friend were talking, and she said, here's some business that would be easy for you. And I had some. And again, we looked down and thought, gosh, we're like basically business partners already, and we didn't even mean to do that. It wasn't intentional, but we had made each other's lives so much easier because she had things that I needed and vice versa. And so if, you know, if you're in a burned out stage, maybe the right next phone call to make is to the person you probably wouldn't have at the top of your list. But it's the planning company down the street that gets the other contracts you don't get. You just started a discussion with them. Most likely they're feeling what you're feeling they're going through. And again, maybe that leads to a discussion of, well, what if we merged, or what if we took things over? What if we bought you out and you went and did your next dream? But if you burn those bridges, you know enough that you can't make that call. That's. That seems pretty silly to me. In a, in an industry we're talking about where my goal is to create things and get them off my plate as quick as possible. Why would I want to shut off people that are succeeding right beside me? Nobody writes that book. Nobody talks about that.

00:39:27 - Courtney Hopper
It's almost like there's some, there's some people that have the vision right and kind of, like, the cojones to make the biggest, the big jumps, and there's other people who have the capital who maybe don't have the vision, and it's like they can see it once you've created it for them and they can fund it. There's never a time that I haven't thought, like, wow, if someone were to infuse a million dollars into whatever situation I'm in, they couldn't make it infinitely better than I could at that time. But they may not have ever had the vision to get it started. So just kind of, like, looking at where you play and, like, kind of staying in that lane to keep yourself fed, but also to create avenues for other people who wouldn't otherwise be creative.

00:40:00 - Casey Helmick
That's right.

00:40:00 - Courtney Hopper
You know?

00:40:01 - Casey Helmick
That's right.

00:40:02 - Dana Kadwell
Yeah. I think, too, like, part of, I think what's so hard and kind of touched on a little bit is just how much when you start something, it becomes a part of who you are. And I was going through, like, a coaching session earlier this year, and I had to write, like, a tagline of, like, who are you? And I haven't heard this tagline. They wanted so much for me to get rid of, like, venue owner or whatever. Like, is that who you are? And I think this is where it gets hard. And going back to your point about, like, kind of being friendly with your competitors is because when you are friendly with your competitor, it's hard for you to look at it as you get defensive of your business. Like, the reason why, you know, you want to, like, say, oh, you're doing this wrong, and I'm doing this right, and you want to try to compare it, and you get offended by this or offended by that, and it's because it's so, so personal, and it's become who you are. And I think that when I finally could let that go, like, really let it go, and I do feel that way, and I think we had many conversations way back when, and I remember I told her, I was like, the problem is, Courtney, this is your identity. This is who you are, and it's not who I am. And there's a difference when you can approach things very differently, and I don't think it is anymore. I think at that point in your life, it was because it was what was keeping her, like, afloat and stable, and so it became everything to her. But, like, and there's a whole different perspective that you can see when you're like, this isn't. This isn't me. This is just.

00:41:30 - Casey Helmick
Yeah, but it's never going to be perfect, because when you're a creator in this way, you have to put a little of yourself into this or it won't work. Yeah, there's a. I tell my son this all the time. He started a couple little businesses. He's nine, and I. He does sports, too, and I sometimes will come home and he's on the upper end of sports. I'll brag on him a little bit, but he's never the best player there. And I'll remind him, you're part of our family. And it seems like the way we're wired, we make things and we use our brain to. That's how we add value to this world. And we may not be the strongest or the fastest or the even the smartest sometimes, but we're able to take something inside of us and bring it to life and keep practicing that. If you want to be the best at something, it seems like for right or wrong, you've sort of inherited that from our family. My dad's an entrepreneur in that way. And it's hard because I watch him pour a little of himself into a little business. He has a little hat business that actually does quite well, and he pours some of himself into it. And then somebody may not like the hat he makes. It's like it is part of you. You took something from inside of you and gave it to the world, and they liked it or they didn't. I think the trick is, again, I may not have this all figured out yet, but it's this mindset of, I want to make it, the whole thing, so great that someone wants to take it from me, someone wants to run it, someone wants to invest in it, someone wants to. I don't want to make something so awesome that I can keep pouring all of me into it, because that feels very counterintuitive to our main journey, which is to make lots of things that can help lots of people. And if you're focused too much in on one thing, I almost feel bad for people, like, you know, somebody that invents, like, Facebook or something, it's like it takes all of them 100 hours a week. They can never do anything else. It feels almost like they're slaved to it. It's like maybe that person was supposed to make it and then just sort of walk away and easy for me to say. They'll lose hundreds of millions of dollars, probably, but, like, maybe the world would be better if that person had made three or four or five or ten other things and not support themselves.

00:43:36 - Courtney Hopper
Yeah.

00:43:37 - Dana Kadwell
Yeah. It just feels very claustrophobic. It feels, like, in it. And I think that's where, as entrepreneurs, I think when you're in that kind of messy middle, you feel very trapped, like, you just don't know. Like, you're kind of stuck in a cage. Like, you don't know which way to go, and you're. And whether your heart's telling you one thing, your mind's telling you another thing, and, like, you're not passionate about it anymore, but you don't know how to move on. Like, it just feels that way, and everyone's felt that way. Just cagey. Like, I call it getting itchy. Like, I get itchy. Like, I just. I can't sit still. Can't move. Like, just paralysis.

00:44:09 - Casey Helmick
When you also don't want to build up a reputation of being flighty, like, that's the person that does it for a little while and then moves on to the next.

00:44:15 - Dana Kadwell
We've seen those because I have actually seen those people.

00:44:17 - Courtney Hopper
I'm like, what is this person doing today?

00:44:19 - Dana Kadwell
We literally just text each other. We'll screenshot. I'm like, what the world?

00:44:22 - Casey Helmick
What's going on?

00:44:23 - Dana Kadwell
What person doing right now? I don't understand.

00:44:25 - Courtney Hopper
It makes no sense.

00:44:27 - Dana Kadwell
But then maybe now it's just exactly what you're saying. They're just figuring it out.

00:44:31 - Courtney Hopper
I don't know. But I think getting back to that point, you want to create something that is good enough that somebody else wants to come along and, like, it makes sense to them. They want to join the club, and they want to invest in it or they want to buy it or they want to do it or whatever, you know? So I think there is maybe, like, a litmus test before you can be snarky. Like, not snarky.

00:44:50 - Dana Kadwell
That's just pure snark. Well, I mean, yes, but at the same time, like, there's been many of people, like, we've had conversations about, like, selling businesses, and they'll tell me, like, my business is worth XYz. I'm like, it is. No.

00:45:00 - Courtney Hopper
To who.

00:45:00 - Dana Kadwell
To who in your mind, you have built it up to be this huge thing. And when I think about, like, when I think about our business, like, our exit plan is we own the, like, brick and mortar, right? We'll probably always own the brick and mortar, and we'll always sell the business. But the business itself, yes, it has a lot of revenue. It makes money. But a lot of the value is in the physical building of it, right? It's in the land. It's in landscaping. So there's, like, all of those pieces to it that are super interesting. And, like, you had to kind of think through those things, but that's super appealing.

00:45:33 - Courtney Hopper
I mean, I've thought about it in many ways. Like, what if we did own the space and somebody else leased it from us and just ran the business? You know? Like, how would I feel about that? Yeah, I guess you'd have to put things in place to protect it. But what's going to say is one thing I know we're just kind of rambling at this point. We got to wrap it up. But I was watching this thing. It was first on Instagram, and they were moderately successful, like, four or 500,000 people or whatever. So maybe that's really successful. I don't know. Anyway, like, followers. Followers, people. People who follow them. Okay, got it. Yeah. I don't do social media, and they were talking about their journey, and they're like, you know, all I can say is, if you're a creative entrepreneur, get out there and do it. It's only cringey until people start to like it. And it's true. Like, you get out there, like, well, this is cringey. But then I. Yeah, you start getting people that are getting on board, and they're like, wow, I really, like, I'm picking up what you're putting down, and it gets less and less and less cringey. And I think, like, as an entrepreneur, it's just like, that this is cringey until it's successful.

00:46:29 - Casey Helmick
You know, I had this moment recently that it was about a year ago. I think I've always been a little self conscious around my wife's family, who are like, her mom was a school teacher for 30 years or 40 years. Her dad's been in the same job for a long time. And I thought, I wonder what they think of me, especially, like, I'm taking care of your, you know, your daughter's family.

00:46:51 - Courtney Hopper
They're probably praying for you.

00:46:52 - Casey Helmick
Yeah. You know, probably.

00:46:53 - Dana Kadwell
Yeah.

00:46:54 - Casey Helmick
And maybe a year ago, my father in law was like, you've talked about opening a coffee shop someday. Let me know if you want to do that, because we would want to be a part of that. Like, we believe in you. You know, that was a big moment for me. I don't think I ever want to do business with family in that way. But, like, my goal as a starter, you see that it's working, that it has momentum, that maybe the next idea won't be the best, or maybe it will, but you believe in the vision of where we as a family are headed, where I'm headed, and before that, there's this self conscious that we all carry around of. Does anybody else see what I see? That I'm sort of the igniter to these things and that that needs to exist, that not everybody can just be a part of the bonfire? Somebody has to start it, and that may be my job. And it's not always the most fun. Sometimes it's great. But to have somebody who is much more risk adverse and, like, invested in the health of his family come and say, like, I think you're good at starting things, maybe we should do. It's like, okay, that's helpful. So I think also as entrepreneurs, like, listening to the people around you and hearing those little signals and not missing them, it would have been really easy for me to overlook that and think, I don't know, maybe he just loves coffee or maybe. But it was really, I think, his way of saying, like, you're doing a good job. I didn't see it initially, or I. It's harder for me to see day to day. I don't exactly know how to explain to people what you do all the time, but you're doing something right, and so keep going. It's like, oh, that's pretty big from somebody who doesn't normally hear that.

00:48:27 - Courtney Hopper
But your mother in law approached me yesterday about that same thing. No, I was joking.

00:48:33 - Casey Helmick
She's like, what?

00:48:34 - Dana Kadwell
Well, this has been really helpful. Thank you so much. I have so many things to think through, actually. Yeah, I know, but how can our people connect with you?

00:48:44 - Casey Helmick
Oh, I'm not good at this part.

00:48:45 - Dana Kadwell
Okay.

00:48:46 - Casey Helmick
No, I think our company's website is just contentcapital.com. so if they want to go there.

00:48:50 - Dana Kadwell
And look around, we'll put in the show notes, too.

00:48:52 - Casey Helmick
Yeah, I definitely don't have 300,000 social media. I'm barely on social media.

00:48:56 - Courtney Hopper
So you're still cringy?

00:48:58 - Casey Helmick
Yeah, a little.

00:48:58 - Courtney Hopper
Okay, good. All right.

00:48:59 - Casey Helmick
We work with a lot of people who have that, so I do see the value, but, no, that's probably the easiest way, is just to go to the website and poke around. So, yeah, thanks for having me.

00:49:07 - Dana Kadwell
Yeah, thanks so much for your time today. It's been great.

00:49:16 - Courtney Hopper
To learn more about our hustles. Visit us on the gram at cndevents at thebradfordnc at anthem House and Hustleandgather. And if you're interested in learning more about our speaking training, venue consulting, or our conference coming up, head to our website@hustleandgather.com.

00:49:33 - Dana Kadwell
And if you love us and you love this show, we be more than honored if you left a rating and a review.

00:49:38 - Courtney Hopper
This podcast is a production of Earfluence. I'm Courtney.

00:49:40 - Dana Kadwell
And I'm Dana.

00:49:41 - Courtney Hopper
And we'll talk with you next time on hustle and gather.