Ep373: Ryan Estes – You Should Always Honor Your Relationships

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Quick take

BIO: Ryan Estes is an American Buddhist entrepreneur and the founder of Kitcaster, a podcast booking agency. He is an expert in leveraging podcasts for meaning and profitability.

STORY: Ryan and his wife co-run a marketing agency. Ryan’s wife came up with a fantastic product idea that she shared with Ryan. He agreed that it was a great idea; he took it over and executed it the same way he would implement a client’s vision. One problem, though; he never consulted his wife, whom the idea belonged to. Feeling sidelined, Ryan’s wife lost interest in the product causing a rift between the couple. In the end, they had to let go of the project for the sake of their marriage.

LEARNING: Honor your relationships even in business. Your business partner is your most valuable asset, cherish and protect them.


“If you have a business partner, somebody that complements you and you have the perfect rhythm, cherish and protect that relationship.”

Ryan Estes


Guest profile

Ryan Estes is an American Buddhist entrepreneur. As the founder of Kitcaster, a podcast booking agency, he facilitates thousands of extraordinary conversations. Ryan is an expert in leveraging podcasts for meaning and profitability.

Kitcaster serves more than 150 agency clients and is gearing up for its first software product in 2021.

Worst investment ever

Over the past 10 years, Ryan has been the owner-operator of Talklaunch, a media marketing agency he runs with his wife. The agency does social media content, paid media, organic search, website creation, and more.

Taking over his wife’s fantastic product idea

Ryan’s wife had this great idea for a skincare company, specifically, a natural deodorant company, and she was excited about it. She came up with this fantastic formula that worked well.

Ryan took over this entire idea and put it through the wringer the same way he would do with a client. He rebranded the idea, built the website, put everything together, and launched the company, all without consulting his wife.

Wife loses interest

Even though the company was having middling successes and Ryan was planning to expand a line, his wife continually became less interested in the business. Ryan couldn’t figure out why she was not engaged in this company, yet it was building traction.

Unbeknownst to Ryan, his wife had hoped that this idea would become a collaborative project for the both of them. Something that you would work on together and bond as a couple. However, Ryan never bothered to find out what were his wife’s expectations from the business. So when he took it over and alienated her, she lost all the interest she had.

Choosing to save his marriage

The business was starting to cause a rift between Ryan and his wife. Once Ryan realized his mistake, he apologized to his wife, and together they decided to let go of the project and focus on something else for the sake of their marriage.

Lessons learned

Draw a line between business and your marriage

When you go into business with your partner, be sure to draw a line between your marriage and your business. Articulate in a conversation all the ways your business relationship could go wrong. Evaluate how your business relationship can affect your marriage and find ways to protect that relationship because no amount of money is worth ruining your relationship.

Always remember that your spouse is your most valuable asset

There are so many parallels between a marriage and a business relationship, and therefore, differences will arise, and ideas will differ. But, the value of somebody who understands you and is vital to you from a business side is more important than any revenue outcome. If you have a business partner who complements you, cherish and protect them.

Andrew’s takeaways

Honor your relationships even in business

When it comes to doing business, honor your partner’s ideas and thoughts. Do not drag your relationship through whatever your next idea is; discuss it with them first.

You and your spouse will have differing expectations

You and your spouse will probably want different things from a business partnership. So if you do not clarify your expectations, your partnership will be a train wreck.

Actionable advice

Discuss parameters and rules before getting into a business with your partner. Talk about worst-case scenarios such as how you will handle the company if you break up, who gets the final say when one of you wants to make a decision and the other doesn’t. Make sure that you have an exit strategy in place in case things go a certain way.

No. 1 goal for the next 12 months

Ryan’s number one goal for the next 12 months is to grow Kitcaster into an absolute behemoth. He, therefore, wants to stretch it out to about a $2.5 million runway.

Parting words


“Thanks for letting me tell the story.”

Ryan Estes


Read full transcript

Andrew Stotz 00:01
Hello fellow risk takers and welcome to my worst investment ever stories of loss to keep you winning in our community. We know that to win in investing, you must take risk but to win big, you've got to reduce it. If you're not already a member of our community, please go to my worst investment ever.com right now to join and receive the following five free benefits, the risk reduction checklists, my weekly investment research email to help you increase investment returns a 25% discount on all a starts Academy courses, instant access to the Facebook community to get to know guests and fellow listeners. And finally, my curated list of the Top 10 podcast episodes. Fellow risk takers This is your worst podcast host Andrew Stotz from a standards Academy, and I'm here with featured guest, Ryan Estes, Ryan, are you ready to rock?

Let's do it.

Andrew Stotz 01:04
I'm going to tell the audience a little bit about you. And first of all, Ryan Estes is an American Buddhist entrepreneur. As the founder of caster, a podcast booking agency. He facilitates 1000s of extraordinary conversations. Kid catchers serves more than 150 agency clients and is gearing up for its first software product this year. Ryan is an expert in leveraging podcasts for meaning and profitability. Ryan, take a minute and fill in for the tidbits about your life.

Ryan Estes 01:43
Thanks so much, Andrew. On top of that, I'm a husband. I'm a father, and I'm a martial artist. I'm also an avid outdoorsman, and a lover of podcasts. I'm so happy to be here.

Andrew Stotz 01:58
That's amazing. And what martial art? Are you an expert in?

Ryan Estes 02:03
Well, I wouldn't say martial art or an expert.

Andrew Stotz 02:06
Yeah, so are you good at?

Ryan Estes 02:08
So I trained capital letter, and I also train Brazilian jujitsu. So I'm a purple belt in Brazilian jujitsu. And, you know, I've had some time off through the pandemic, to really, I think we organize my attention into jujitsu. So I'm really excited to go back to it. Hmm.

Andrew Stotz 02:32
And what is it you like about it?

Ryan Estes 02:35
It seems so violent. Yeah, absolutely. No, it's the violence that I like, you know, I think that violence gets painted a negative picture, and rightfully so. But, but violence is a part of our life. And I think having a positive experience with violence is really good. You know, I think it shows you how fragile we all are, and allows you to discover, I think empathy for people around you. I also really enjoy the violent embrace of other men and women, you know, in a platonic sense. So I feel like it might tap into maybe my primate brain a little bit to just roll around with a really, you know, jujitsu is unique in the sense that it's a grappling sport. And as such, you can kind of give it 100%, you can know you can go as hard as you possibly can, the other person can as well. And you have a relatively safe environment to do that. So I think I enjoy the touch of other people, even though it is violence. And I also like to explore, you know, my own violent tendencies in a very positive and productive way.

Andrew Stotz 04:06
so fascinating. I never thought about it that way, then, you know, I go back to the school yard where we had, you know, fights when we were kids, and then, you know, this is something, there's something cathartic when you've had a fight with somebody. And it's all of a sudden it's gone, you know, the anger or the frustration or whatever. That's pretty fascinating. You know, there's another angle about this, that makes me think I live in a culture here in Thailand, where confrontation is simply not allowed. It is frowned upon. It is not you know, you will not hear people yelling. You won't even people hear people honking horns. People do not confront each other. They live in a more, let's say, harmonious way of living together. However, that doesn't mean that they don't have violence and that doesn't mean that they don't have that true disagreement, it just means they're not allowed to settle it through that confrontation. And the result of that is that it comes out in different ways. I mean, first of all, when violence does come out, it's just very brutal. But the second part is that it gets re channeled into fiefdoms in power. And rather than duking it out, let's say in the, in the management team meeting between two sides, they'll never confront. And instead, they'll go and build their fiefdom of people, their followers, and then you get these factions within companies and within society that will never ever resolve the issue. And that is such a fascinating dynamic. And now, you've kind of reminded me of the cathartic nature of confrontation, whether that's physical or mental and emotional, that there's some value there. It's a different, you know, different way of thinking here, but you remind me about that.

Ryan Estes 06:07
Yeah, I've got a couple of takes on that, you know, that's, you know, I have to take your word for it, because I haven't been to Thailand, but I also know that they have one of the most extraordinary martial arts disciplines in the world, and muy Thai, that is ripe with ritual, and music, and ceremony, and in all of these things, and one thing that I'm really interested in, in martial arts is the ability to evict kind of a evict evoke, no, because a better word, evoke a flow state. And the flow state might be, you know, synonymous of like, when you saw like, Michael Jordan back in the day, and his like tongue came out, he's moving in slow motion, he moves right around somebody. Well, in a way, martial arts, particularly competitive martial arts, is kind of a technology to evoke flow state. And when done correctly with opponents, then they both enter kind of a state of group flow. And there, there's a dance, you know, they call boxing, the sweet science, you know, so through this incredibly violent act that has real repercussions, especially in my tie, like you can get really hurt doing that. But it creates a certain experience, that kind of transcends, it's just a, it's an altered conscious state, you know, and so there's, there's a pursuit of that. And then the other side of it is, you know, we all have this fight, flight or freeze mechanism, that is innate in our biology. And you really don't know which one of the three, you're going to get when you come under stress. And there's a great quote that I think comes from the Marine Corps that says, you know, you don't, you don't rise to the challenge, you fall to the level of your training. And so and so by training, you know, this, this mechanism, where you put yourself in a position of fight, flight, or freeze over and over and over and over and over and over and over and over and over again. It gives you maybe a little bit better barometer of how you might, you know, operate when you're really under that kind of stress, you know, so, yep, as kind of a risk aversion tactic. It's not a bad idea, you know, to put yourself out there in practice and see what you can do.

Andrew Stotz 08:43
Well, speaking of fight, flight, or freeze, many of the people I invite to come on this show, they are in flight mode, they run away, the second one, and they do so with a with a with a parting message, usually, some of them freeze and don't know what to do, so they don't reply. And finally, a small, rare group decide they're going to fight, and they're going to tell the story of their worst investment ever. And now it is your time to tell us that story. And since no one ever goes into that story, thinking it will be tell us a bit about the circumstances leading up to it then tell us your story.

Ryan Estes 09:24
Absolutely, I would absolutely love to. So over the last 10 years, I've been the owner operator of a media marketing agency called talk launch in tender, and I ran it lot largely with with my wife, and over the years, doing paid media, whether that's like search or social media, organic search, social content, building websites, you know, basically a digital agency. You know, we learned a lot One of the things that we also specialized in was crowdfunding campaigns. And we would help launch brands through Kickstarter, or kind of those kind of campaigns and raise money. And so we really became experts in building a brand, validating the brand, gaining traction and scaling. And so as kind of the business matured, there were certain things that were unsavory about the business. And largely, that would be a client load, you know, and perhaps people can, it can relate to that, that, you know, if you're working with clients, you might find yourself heavily leveraged where you really need that client relationship. But they might be completely out of their mind. On top of that, they might be kind of main, you know, and they might miss treats you but because the relationship is so important to the nature of your business, you're stuck to them. And because I worked with my wife, you know, and we have two children, you know, that conversation, that frustration would spill over the dinner table, you know, of like, these clients that were torturing us. And we knew they were torturing us intentionally, they knew they had that boot on our neck, you know, and there was really little we could do. But because we were, you know, kind of experts in like, trying to figure out products that would be successful and how to launch them, we started out launching products, and to varying degrees of success. And in mostly not success, you know, we went about that. So, my wife was basically managing the day to day operations of the agency, and I was out there validating ideas. And one of the ideas that my wife had was for a skincare company, specifically, a deodorant, a natural deodorant company. And she was really excited. And she came up with this, like, really cool formula, that worked really well. And we used it, you know, and it was like, Okay, well, this is kind of ready to go. And she was excited about launching it. So I'll skip to the end of the story, then backfill, I took over this entire idea. And put it through the wringer in a way that I would do with a client, not knowing that there was emotional content that was wrapped up in this idea that had to do with our marriage, and our family, and our career decision. Everything else that I was blind to at the time, and it ended up being nearly catastrophic. So that's the end of the story. But I'll back up a little bit and just kind of walk through it. So she had a great idea for formulation. And so we said about our validation process, which is, you know, let's find 100 people that are by it. So, you know, I'm big on, you know, one on one interviews, so we put it together, we interviewed people, the idea and direction that she had had for the product wasn't necessarily resonating with them, but they liked the idea of a natural deodorant. We sent out samples based on the feedback. I, I took the idea, I rebranded the idea. without consulting, my wife, the founder company, built the website, put everything together in launch the company. The company was having middling successes, I was looking to expand a line and finding less than less interest from from my wife, you know, she, she at that point was kind of like, I couldn't figure out what what the problem was, and why she wasn't so engaged with this company that that was starting to build traction. At the same time, I was, you know, speaking with some of the founders of native deodorant, which was on a similar trajectory, and I felt like being that it's a perishable product that has real opportunities to scale, particularly with a small team, you know, all I saw was dollar signs. And so I started running at it and the The business kind of came to a head outside of a Whole Foods down here in Denver, where we live, where we were kind of handing out samples and, you know, in the how a wife will do, she kind of let me know, in uncertain terms that, that I had destroyed her dream and ruin this product. Now, when I'm here to help, yeah, I'm here this year to help you the best I get. So, you know, to add a little bit context, you know, our children are an elementary school still, and the pressure from the agency, of course, we have all our responsibilities there. And we're really looking for a way out. So on my side, if I was to rationalize it, it's like, Hey, you know, I have a certain skill set that I can rush this thing to market, I can, I can, I can get us in a position I, you know, I'm thinking about paying for college. And, um, I'm thinking about, like, you know, putting your face on the side of the box, and this and that, but, but I think what was really important to her was that, like, we were gonna have a project that we worked on together, where I had been, you know, where I had been working on these other projects, you know, software and goods and, and services and things. And she'd been, she had been working on the agency and, you know, kind of two ships passing in the night, although, you know, we were shoulder to shoulder You know, there's a certain loneliness that can happen in a marriage, if you're not careful. And it's more acute than something that happens if you're actually by yourself. And I think we were falling into that. And I think for her, it's, she saw it as a creative project, that would be collaborative. And that we could work on together and, and have fun with. And, you know, once I got a little sense of the cash involved, I really ran it with gusto and kind of steamrolled over her, you know, so that was my experience. Now, the ending of the project was basically a conciliation of like, Listen, an apology, if I blew it, you know, I blew the whole thing in this project. I think it has, it has legs, we have customers in but, you know, let's, let's not do this, you know, and so I let it go, you know, and, and maybe, like, a lot of your listeners have listened to a bunch of your podcast episodes, you know, a lot of your worst investments, there's always like, a big grain of wisdom that comes out of that. And one of them was just to, to really honor and respect my marriage, and, and not to be too blinded by my ambition. You know, so.

Andrew Stotz 17:52
So that was, let's, let's review. But before we go through these lessons, which I think that first one about honoring is great. Can you remember, like the worst day between you and your wife? That there was from this whole experience?

Ryan Estes 18:10
Yeah, it really was in front of Whole Foods, US arguing with a tray of deodorant of all the ridiculous things. But the argument was acute enough that it did freeze in my memory that I can I can I know how the shadows looked on the garden box that we were sitting as we arguing, you know, that kind of that kind

Andrew Stotz 18:34
of where you were you at the point where you could see what she was saying over you at a defensive point at that time?

Ryan Estes 18:42
You know, I was definitely at a defensive point. You know, for me, it's always coming back. I'm a fiery person. So in the moment, you know, oftentimes, I find myself trying to win a point. It's not until retrospect, I'm like, oh, boy, I was being an asshole. Like, geez, you know. So, you know, in the moment, you know, it's like, I felt kind of like, irritated and like, because I had my set of my set of goals and priorities, and they're like to be diminished. But sometimes, you know, the bigger picture is more important than, you know.

Andrew Stotz 19:26
Yep. So how would you summarize the lessons that you've learned? You've mentioned the first one was I wrote down which is honor your relationship?

Ryan Estes 19:35
to hang out? Yeah. Yeah, absolutely. You know, I think particularly as like, people are working from home. And entrepreneurship becomes more and more available for everybody. And in relationships in marriages, you might have somebody career who catches fire and it makes sense for the other partner to contribute in To work in the relationship, I think it's it's really good idea to keep track of when the day ends. But also to understand clearly like what you're doing, you know, I think the last side of that I think I saw, you know, this is an opportunity to be a next chapter in our life and was kind of intoxicated by the idea itself. Whereas for her was like, a place for us to connect, and the exact opposite happened. So, you know, I think, I think a lesson maybe to take away as people are starting to think about going into business with their partner, I really actually do recommend it, I think there's, there's great ways to do it. But I think that the way to do it successfully is to realize and articulate, you know, in conversation, all the ways it could go bad, you know, yep. Like, how, how could this be catastrophic for our relationship? And, you know, especially with couples, you know, like, you have to protect that relationship. Sure, you got a 10 million business $10 million business idea. Fantastic. But you know, a deep connection in a family is worth so much more than that, you know, so, you know, even itemized the ways that might be catastrophic, and go bad, is probably time well spent. Because you'll see how kind of naturally your outcomes are misaligned. And you can fix it.

Andrew Stotz 21:48
Yep. Well, let me summarize a few things I take away, it reminds me of the story of my business partner, Dale, and I here in Thailand, and we started a coffee business, and it's a factory and Dale has been running it for 25 years, and we're equal shareholders. And, you know, I have my opinions. But the truth is, I'm outside of the business. So I've always, you know, told my opinions, but you know, not to forcefully because I don't know what's happening on the front line that he's dealing with. But also, in the beginning of our business, we said to each other, if this business ever was had the risk of damaging our relationship, we're gonna shut it down. And that was kind of our way of putting our friendship above the business. And by doing that, and agreeing on that, it really allowed us to stay together through that thick and thin. And I think that the words that you said, I think, really great for the listeners out there, honor your relationships, you know, like, you just don't drag your relationship through just whatever your next idea is. You know, instead, think about it and also understand, the other thing I'd take away. So the first thing I took away is, you know, kind of reminded me that story of Dale and myself, the second thing that I think is good for the listeners is the idea of honoring your relationship. And then the third thing is understand, particularly when it comes to our husband and wife, that they both probably want different things out of that experience. And if you haven't clarified that, then it's just a train wreck. Because as a typical man, you know, we're kind of focused on action, and results. Whereas for, I'm not going to say typical woman, because I don't know that, but I know for typical man, but I would say for a woman, or maybe in your wife's case, it's more about the journey and the experience. And if you go at it with action, and outcomes, and somebody else is looking for experience and the journey, yeah, it's a disaster. Those are things that I took away from it, he would add to that.

Ryan Estes 24:02
I feel like that's so wise. And there's so many parallels between a marriage and a business relationship. Part of me, you know, it's, if you have a relationship, let's say your marriage obviously, is very important. You want to protect it, but you have a business relationship with someone, maybe a trusted partner. Obviously, like, differences are going to rise. Ideas are going to differ, but the value of somebody who understands you and is important to you from a business side is incredibly important and possibly more important than any revenue outcome. You know, there's strength in numbers, the idea that you can go it alone or that You know, it, relationships are something to protect, you know, even if there's a loss, you know, because out of that loss, you hopefully you can find something better. You know, if you have a spouse, if you have a partner, if you have a business partner, somebody that complements you, in you found a certain rhythm. Like, that's to be cherished and protected. Yep. That that's something that like, like what you talked about, you know, having having maybe some guidelines, like, Hey, we know that, especially entrepreneurs, we're gonna be firing, we might be manic at times, we might be out of our minds, we might not be able to articulate our ideas, but we just need to work it out, like, Oh, that's okay. But protect the relationship. You know, I think that's, that's really important. And when it pays in the end? Yeah, I

Andrew Stotz 25:57
think it's a huge takeaway. So based upon what you learn from this story, and what you continue to learn, let's think about that young person that's in a relationship right now. And they're stuck at home, or they're trying to create some value together. What one action would you recommend our listeners take to avoid suffering the same fate?

Ryan Estes 26:17
You know, I would, I would go into it into a conversation with certain parameters, certain rules, and talk about worst case scenarios, you know, I would say, what does it look like? If we break up into businesses successful? What does it mean? If I want to make a decision and you don't, who gets the final say, have an exit strategy have have a way out that you've pre determined that if things go a certain way, and if you can stomach it be as dark and horrible as things we know, get, you know, you know, if it's, if it's a marriage, like, you don't want to think about divorce, but like, you know, think about like, what, what, what are your intentions? If it's a marriage, if it's a business relationship, you know, hey, if everything goes south, you know, how do we work this out? You know, those are important conversations to have early on, and uncomfortable. So I would suggest that being a veteran of these kind of conversations, you set parameters, and you say, hey, if we need to take a shot, or something, or we need to, like, stop talking about this, it could be a process, you know, because it can really, like evoke some some pretty powerful emotions. And in that doesn't have to be resolved in one conversation. You know, if, particularly if you have big emotions springing up, you know, it's probably best to say, you know, hey, I have some things that are welling up right now. Like, let's pause and come back to this conversation. But again, like, we were talking about jujitsu in like fight, flight, or freeze, you know, like, put yourself in that situation, you know, because you're never gonna be there. No, that's gonna happen. It's gonna happen one day one at one time. So you know, practice, practice it out of respect to your partner, especially out of respect to your partner. If things go south in a negative way that you can, hopefully manage your own self with dignity. You know, so you don't have regret, you know, because things change.

Andrew Stotz 28:38
Well, ladies, gentlemen, you heard it there from running, explore worst case scenarios, and what better place to do it than to go to my worst investment ever.com. And listen to some of the past episodes. In fact, you can search startup, and you'll find many of the stories of people that had failures in startups. So let me ask you, last question. What's your number one goal for the next 12 months?

Ryan Estes 29:05
Next 12 months is to grow kit Castor into an absolute behemoths. So what that looks for, like for me right now is to stretch it out to about a $2.5 million run rate. That's what I'm focused on in the next 12 months

Andrew Stotz 29:20
exciting. And for the listeners out there who are either podcasters themselves or you know, high level CEOs or others that want to get on podcasts. What should they do in relation to kick caster in your business?

Ryan Estes 29:35
Absolutely. You know, if you are interested in podcasting, even in a casual sense, the secret with me is I love to talk about podcasting. So you can go to Kate caster Comm. We have an application there, fill it out. Now if you are a funded startup founder if you are an entrepreneur with x If you are a C suite level executive, these are the people we serve. And we put them on the world's top podcasts, so that you can share your story. You know, you can, you can grow professionally and personally through expressing your story and you can create assets for your brand to grow and thrive. So kid caster.com is the best place to kind of learn more

Andrew Stotz 30:26
beautiful, and we look forward to your exciting growth. Well, listeners, there you have it another story of loss to keep you winning. My number one goal for the next 12 months is to help you my listeners, increase return and reduce risk in your life. To achieve this goal, I've created the free membership group with five free benefits I mentioned earlier, just go to my worst investment ever.com right now, to join. As we conclude, Ryan, I want to thank you again for coming on the show. And on behalf of East Arts Academy, I hereby award you alumni status for turning your worst investment ever into your best teaching moment. Do you have any parting words for the audience?

Ryan Estes 31:11
I just appreciate being on the show so much. This was fantastic. Thanks for Let me tell the story.

Andrew Stotz 31:16
great having you on. And ladies and gentlemen. I'm going to just add a little parting words. Honor your relationships. And that's a wrap on another great story to help us create, grow and most importantly protect our wealth. Fellow risk takers. This is your worst podcast hose Andrew Stotz saying. I'll see you on the upside.


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About the show & host, Andrew Stotz

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it.

Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth.

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