99: Mixing Business with Podcasts with Ryan Estes of Kitcaster

Wherever entrepreneurs are in their journey, podcasts can take them further, whether as a guest or a host.

Ryan Estes, co-founder of Kitcaster, joins Tim Bornholdt of The Jed Mahonis Group to chat about why podcasting is the Trojan horse of marketing for startups, how audience quality over quantity results in conversions, and why everyone should sit down with a couple friends, grab a bottle of wine, and start a podcast.

In this episode, you will learn:

• Why podcasts feel familiar
• How to quantify the value of hosting your own show
• How to enhance listenership of a show
• Tips for getting ranked on Apple Podcasts
• How depth over breadth translates in podcasting
• Why you should, um, keep the fillers
• Where to start with starting a podcast and why everyone should do it
• Which “junk food” podcasts Ryan and Tim find therapeutic

This episode is brought to you by The Jed Mahonis Group, where we make sense of mobile app development with our non-technical approach to building custom mobile software solutions. Learn more at https://jmg.mn.

Recorded October 26, 2021 | Edited by Jordan Daoust | Produced by Jenny Karkowski

Show Links

Kitcaster.com | https://kitcaster.com/

JMG Pricing Page | https://jmg.mn/pricing

Connect with Tim Bornholdt on LinkedIn | https://www.linkedin.com/in/timbornholdt/

Chat with The Jed Mahonis Group about your app | https://jmg.mn

Rate and review the show on Apple Podcasts | https://constantvariables.co/review

Episode Transcript:

Tim Bornholdt 0:00
This episode is brought to you by The Jed Mahonis Group. We build best in class iOS, Android, and web apps. We do this by integrating with teams that lack mobile expertise. And we work together to deliver creative mobile solutions that solve real business problems. To learn more about us and to see our pricing, which is something we're very transparent about, visit JMG.mn.

A small request before we get into this week's episode, and you'll learn more about it in this episode, we're trying something new with ratings and reviews. We know these asks are annoying, but they're very valuable to us. So as a thank you for taking time to rate and review us on Apple podcasts we will give you and or your company a shout out on a future episode. Leave a rating and review on Apple podcasts, get free advertising. It's that simple. Even simpler, you can go to constantvariables.co/review and we will take you right there.

Welcome to Constant Variables, a podcast where we take a non technical look at building and growing digital products. I'm Tim Bornholdt. Let's get nerdy.

Today, we are chatting with Ryan Estes, founder of Kitcaster, a podcasting agency whose mission is to put the world's top startup founders on the world's top podcasts to help them share their stories with a wider audience. Ryan joins the show to talk about how entrepreneurs can use podcasting to grow their revenue, the traits of a good podcast host, how to Increase listenership and when you should and shouldn't host your own show. So without further ado, here is my interview with Ryan Estes.

Ryan, welcome to the show.

Ryan Estes 1:56
Thank you so much for having me. Appreciate it.

Tim Bornholdt 1:58
So I want to jump right in with the million dollar question of how did you get into podcasting? And what's your story like, how did you end up going from where you are, where you were to now founding Kitcaster?

Ryan Estes 2:11
Yeah, you know, I got into podcasting a long time ago. I was originally introduced to podcasting through this expat Korean Zen monk named Henry Grunberg. I found this guy on Twitter. At the time, I was kind of at war with all these Buddhists on Twitter. That's a story for another time. There's no war like war with Buddhists, trust me.

Tim Bornholdt 2:37
Yeah, no joke.

Ryan Estes 2:38
But I got to talking with him, and kind of found a kindred spirit. And he released this series of essays called field of weeds, which was about him returning from Korea monastery, and working construction He'd take the bus to the job site, and they're brilliant. I'm sure they're still out there, field of weeds, definitely check them out if you're interested in that kind of thing, very esoteric and interesting. Anyway, he had published these as podcasts. And so I'd heard podcasts and whatever, I think this was probably, boy, this might have been iPhone one era, iPhone two era, technologically, 12 years ago, or whatever that was. So I started listening there. And then kind of found, this is when you would have to download podcasts to your phone or your iPod. So you'd kind of do your search on your laptop through iTunes, find podcasts and then download it manually.

And so you know, through kind of fiddling around looking for his podcasts and downloading them, I was like, wow, there's podcasts on everything. And kind of discovered podcasting through that and just started downloading a bunch of stuff. And I found it to be early on this, like, amazing salve for my lonely soul. I had kind of a two hour commute each way and ripped through my music pretty quick. And then found myself really kind of attracted to podcast, mostly because of its kind of, I don't know, charming amateurism, you know. There's a density to books on tape, or to audio books, that is like, Man, I kind of want to, I like podcast because you kind of fade in fade out. Not your listeners, of course, I'm sure they're very attentive.

Tim Bornholdt 4:18
They're all out.

Ryan Estes 4:20
They're totally out. It's just playing while they're asleep. So I kind of found podcasts that way and it's stuck.

Tim Bornholdt 4:27
I think you're right, like, I've never really thought of it that way. But having podcasting the amateur side of things be more approachable, maybe is the right word. Just whenever you listen to something, you know, not to rag on NPR or Gimlet or any like very highly produced, you know, talk program, where you really do have to pay attention and it's just kind of stressful sometimes, and it's almost like a chore. I think that the podcasts that I love the most are when it's just this, where it's just a couple of people talking about a topic that I'm interested in, and you're not always fully engaged, you know. There's times where you can kind of weave in and out, but for the most part, you're kind of as they talk about something, your mind maybe will wander to something on the similar topic, and then you get brought back into the conversation and it's low pressure.

Ryan Estes 5:15
Absolutely. And it feels familiar, you know, if people are just talking, it seems like you're in a group of people, and there's a side conversation happening, and you're eating the appetizers listening to them. You know, it's familial, whereas, like, if you're talking about, yeah, like kind of journalism or, you know, 60 minutes or something, and Leslie stall, and, you know, those are very unnatural ways to communicate. I mean the talking sounds weird. There's always an agenda. There's some gotcha moments, but generally, podcasting seems to be more endearing, and like people are trying to meet in the middle, you know, so I really like that, you know. I do like the density of, you know, audio books. I love audio books. I like, you know, even further density, if you're talking about like religious scriptures, and poetry and stuff like that. I like that too. But like, for just kind of general consumption for your traffic jam, you know, I found like, finding comedy podcasts and music podcasts just to be great to kind of like space out to. So I guess it filled this, like, interesting hole of, you know, kind of alleviating the drudgery of, you know, stuff I had to do whether it was traffic, or it was folding laundry or doing the dishes. I didn't necessarily have to bring weight to it with something I really wanted to study. Rather, I could just kind of enjoy what's going on.

Tim Bornholdt 6:37
Oh, yeah. And how did having that experience with podcasting, how did that feed into going out and starting your own business within the world of podcasting?

Ryan Estes 6:46
You bet. So I did it so early in around that time, I was launching what would become, you know, Denver's first social media marketing agency. It was called Talk Launch. And I had kind of, you know, came up doing building websites and doing MySpace campaigns for local music bands. I was a musician at the time, although it pains me to say was a musician. And at the time, you know, folks, were just kind of doing freelance stuff to help bands market and promote themselves online. You know, this is probably about the time Instagram was born. Facebook had kind of, uh, basically shut down MySpace. And it was like, you know what, I think there's an opportunity here. This is before Facebook business manager, and any advertising opportunities on any social media platforms. And so I started an agency that did just that.

So at that time, you know, I also started my first podcast, which was really a way for me to transition out of my career in music, if you could call it a career, successfully, and kind of work towards what I was going to do next. You know, at the time, I had two small children. And the music industry was not necessarily the fulcrum of commerce, on a local level. So I had to make some new decisions. So I started this podcast, and that really helped me kind of get a footing on a new direction, where I could hang out with my friends and talk trash and just have a good time, which kind of took the place of rehearsing music for me, socially, and then work on this agency.

So that first podcast kind of gave way, I started another show called The Denver Business Podcast, where I interviewed founders of business and entrepreneurs locally, which I immediately found was a great Trojan horse to creating business for my marketing agency. And then, you know, went on to produce, you know, maybe a half a dozen different podcasts for different people, was always kind of active in podcasting, in one way or the other for the last 12 years. Three years ago, I was kind of having breakfast with a colleague, Brandy Whalen, our co founder. And she had a PR agency, and she would send me her PR clients to be interviewed on the podcast. And she and I just clicked, you know, we had a good friendly relationship. And she was kind of like, let's do something together, you know, a project. I was like, Okay, what do you want to do? And she's like, something in podcasting. So we kicked around a couple ideas. And out of that this idea for a podcast booking agency was born. I think what kind of drew us to it is both of us come from kind of startup background. I had just come off kind of a failed SaaS product and was, you know, looking for something new. So when we were thinking about this agency, you know, it was really a matter of how do we scale a business like this, you know, and it was really clear from the get go that the way we do it is kind of, you know, putting butts in seats, creating a business culture and hiring people. You know, having a run regular business has always seemed a little bit novel coming from startup SaaS land. And so I think that appealed to both of us.

So we kind of launched the the company officially September 2019. And since then, you know what we're about two years after that, and we got a team about I think, 18 of us, and we're growing pretty well. So, you know, podcasting has always been an absolute passion of mine. I love it. I'm an evangelist and pretty corny about it, tell you the honest truth. So I feel like I have the dream job this is I have so much fun of learning from our founders and our clients, which are just dynamic and amazing. And also just being involved in podcasting in some capacity and give it back to that way.

Tim Bornholdt 10:45
I know of a handful of different podcasting booking companies kind of like yours that go out and actually help people get on podcast. But I think one thing that I've seen that kind of differentiates Kitcaster from others is not only do you get those appearances booked, but you can also measure conversions and make it so that you can, podcasting is notoriously difficult to understand, you know, any kind of analytics and metrics. So, I'd love to hear you talk about how you're able to help people kind of quantify the value of being on podcasting.

Ryan Estes 11:18
You know, actually, I'm always trying to learn. I mean, one thing about podcasting is there is no central database for numbers. We can have some ballpark values have of, you know, size of an audience. For example, maybe one misconception that folks have going on a podcast as a guest, is you might think that the more audience that listen to it, the more conversions you'll have. And largely, we found that to be false. You know, so we spend a lot of time on the beginning to figure out what the outcomes of the campaign really are like, what do they want out of these podcasts? Everybody wants prospects, for sure. But some folks want fundraising. A lot of people are using podcasting right now for recruiting, you know. There's a great shortage of talent. People are looking at it for personal branding, you know, brand exposure, so we spend the time to really figure out what they want. And then we qualify the audience that's going to give them those conversions. And then we look for the podcast that has that audience. So dependent on the client, it's totally variable of like, what's best for them. Some clients, yeah, you know, want a really big audience. Abroad reaching kind of common person, audience is what's best for them. And we have programs for that. But a lot of times what it is, is we're looking for a very niche audience. And we really kind of go above and beyond to qualify the podcast that speak to that audience.

Tim Bornholdt 12:53
It's nice that you say that, because I've, there's so many, there's so many ways to get your message out there. And I think people approach podcasting with kind of that blanket approach of trying to get on the biggest show as possible. And, you know, to some extent, your Squarespaces and your other advertisers, it might make sense to have a campaign that you're on all the podcasts, and you become known as the MailChimp of whatever. But I think as far as being a guest goes, you don't, no one really in this space has millions and millions of listeners, like I think most people that I know that have podcasts, if you get, if you average, you know, even like getting 1000 downloads in the first week of your episode, like you're doing pretty good. And even like if you have 1000 people that are tuning in every week or every other week to hear your message, like, you know, if you can get on a show where somebody has that kind of micro credibility and you have a product or a service that can, that you want to reach those exact people. It's like that can be lightning in a bottle that one single appearance could lead to lots of opportunity for you.

Ryan Estes 13:59
Absolutely, you know, I mean, I guess I'm using war metaphors. But I would much rather have 300 Spartans than a million of the Persian army, you know what I mean? So it's like, if you're looking for conversions, niche podcasts are people that are providing solutions for their show. And that's the reason people are seeking them out. You know, that's the place to go. Now, I mean, in our onboarding form, we say, you know, what are some podcasts you'd like to go on aside from Rogan, Tim Ferriss and How I Built This. We understand that everyone wants to go on those shows. But those shows don't take inbound leads, for one, but also like, those are just, those are entertainment shows. People are going to those shows to tune out of the solutions they need. You know, I want to hear stories about DMT and hunting too. So that's why I go to Rogan. But if I'm looking for a solution for a problem I have then I'm going to go find a different podcast that's going to be offering up solutions consistently. And that's where you're gonna get those conversions

Tim Bornholdt 15:03
100% Agreed. Now with our podcast we've always recorded remotely and virtually so everything within the global pandemic and having to work from home has actually made it a lot easier for us to book guests because it kind of forced people to become comfortable with like broadcasting from within their own houses. So I'm curious to hear from your perspective, how did the pandemic impact you at Kitcaster?

Ryan Estes 15:28
Oh, man, you mean aside from sheer terror?

Tim Bornholdt 15:32
Yeah, you know, just besides that.

Ryan Estes 15:34
So, okay. So, you know, we launched September 2019. At the time, I was kind of validating different products, and my wife was largely running our agency, which, you know, from 12 years ago, was still doing really well. And we were planning, transitioning as she was changing careers, and I was going to move towards Kitcaster, so I kind of, you know, bookmarked March 2020 as the time that I would convert, you know, over to Kitcaster full time, which meant kind of shutting down the agency. But you know, February 2020, comes around, I'm like, Man, this is some nice revenue from this agency that's kind of been operating for a long time. We had, you know, great clients, you know, that we'd had for many, many years. And so it's kind of like, yeah, maybe I can do both.

But, you know, COVID did solve that problem for us. We were at the time, pretty heavily leveraged in food and beverage and hospitality with the agency. And so, we, you know, we lost, I think, you know, maybe a couple dozen clients in one day, you know, so it's like, Oh, well, I guess the agency is over. What's up with this Kitcaster thing? So both Brandi and I, you know, she also was still working her PR firm, kind of turned our attention full time to get Kitcaster and was like, hey, you know, I think this is going to work, because for the reasons you just outlined, that, like, largely, a lot of these podcasts are recorded remote. But also, you know, our kind of ideal clients, which are SaaS founders, these are folks, you know, particularly venture backed SaaS founders, these are folks that have sales and marketing team. They've got fulfillment team, they got product team, you know. If they're not sharing, you know, a roof, you know, what's really left for them to do, you know, when everyone's at home, and kind of working remote. And podcasting really became a thing that they could do to show leadership, to talk about how their company is adapting to the challenges, to find out how other companies are adapting to challenges. So we kind of had this suspicion that like podcasting is going to be a good bridge for them to get to wherever the heck we were going. And so, you know, we kind of aggressively went after it and saw just kind of explosive growth. There was a market there where we thought it would be, which was very satisfying. And, you know, kind of also, I think, provided on an emotional level, a way for us to come to terms, just like talking to each other like, Are you okay? Where are you? You're in Toronto? What's it like there? Terrible? Yes. It's bad here. I mean, there was there was kind of a lot of nursing going on. I mean, I still remember my first zoom call with clients where they're like, literally in their jammies with their comforter pulled up to their chin. You know, they're showing up to work like that. I was like, okay, okay. That's how we're gonna do it. Okay. I'm good with this. So yeah, so that's kind of you know, how that whole thing transpired, I suppose all the way through whenever it was July, when we made way for the, you know, political upheaval, and the massive protests all over Denver, which gave way of course, to the massive upheaval and insanity of the election. It's a weird time to have a young business.

Tim Bornholdt 18:59
And you're talking to somebody that is from Minneapolis, so it's not like we had anything to do with any of that unrest or any of that.

Ryan Estes 19:07
I've heard there was fires.

Tim Bornholdt 19:09
A couple.

Ryan Estes 19:10
Yeah. So yeah, you know, it was pretty, pretty squarely, you know, as it was for everybody. But, you know, I think that as a team, we came together. It became really important to us to be out in the open about some of these emotional things of like, you know, everyone's got stress, anxiety, addictions and depression going on, like, How are we gonna manage this? And largely, I think the team really pulled together and were able to deliver at a very high level.

Tim Bornholdt 19:40
It certainly seems like it. I mean, I think there's nothing like a shared tragedy or a shared stressor to bring a team together and give something to rally behind. So I think that's what a lot of teams are striving for, is that kind of common goal and objective to get, you know, accomplished. So it's satisfying to hear that the pandemic, you know, in a lot of ways, it's one of the, you always have to preface it with, we're obviously talking about a pandemic, and social unrest, and like some terrible things that are happening in our world. But at the same time, you know, that's kind of the American dream, in a lot of ways is, when you see injustice, or when you see something that's not right, you have this entrepreneurial capability to jump together and band together and solve at least a problem in one way and kind of help push things back onto a track that you see as the right way to move forward.

Ryan Estes 20:35
100%. It's good to be in America. You know, waving the flag right now, it's pretty incredible, you know, to be able to just move at the pace that we can move.

Tim Bornholdt 20:47
Agreed, you know. We've talked a bit about the value for entrepreneurs being guests on podcast. I'd like to shift a little bit about talking about the value of entrepreneurs having their own podcast. I know that you've mentioned your podcast, and it's actually ranked pretty consistently in the top 100 iTunes podcasts list, which, you know, to some people might seem like a vanity metric, but being ranked and the whole rate and review the show disclaimer that people have already heard once before, when starting this episode, and they're going to hear again, at the end, you know, that stuff actually really does help drive listeners to your show. So I'm curious if an entrepreneur has a show, what tips do you have for them, from the perspective of getting more people in the door to listen to their podcast?

Ryan Estes 21:32
You know, I think the one thing is, I would just encourage them to not do it for that reason, first. You know, if you're chasing numbers, you're always gonna be disappointed. And that's a terrible thing for your podcast. You know, it's like you said, Get 1000 listeners, man that's amazing, you know. But if you're looking at somebody else's got 2000, you're like, I wish I had that. It's just your kind of chasing your tail, you know, so one, be happy with where you're at.

Now, two, there's a lot of different ways that you can enhance the listenership for your show. The first one is to launch your show. If you didn't tell everybody that loves you that basically your relationship hinges on the fact that you get a rating or a review for this podcast, then you didn't really launch the show. So there are some fantastic services and service providers that will help you do a launch. If you're a year and a half in and you're like, I never launched my show. Actually, I just started recording and told a couple people. There's still time, you know, to launch the show or relaunch it, you know. Alap some new cover art on your podcast, call it a relaunch, but spend some time to do it.

You might not find a lot of material looking for launching podcasts. But you'll find a ton of material on how to launch crowdfunding campaigns. And the idea is exactly the same. You know, which is to say, like, how many people are going to buy your product? Or in this case, rate and review your show, you know. Like, I don't know, 200. It's like, No, no, how many people will really do it. 30, you know, and so you work all your contacts for weeks building up to a pre launch, you know. If you've got a good email list, you build up that pre launch anticipation, and then you get them to converge on one day and time where you get all of those ratings and reviews dropping on one particular thing. That's what triggers Apple podcasts algorithm, that puts you into the featured or the also heard as or puts you in that top 10 ranking. And that's where you find, you know, random people jumping on board for the podcast. So, you know, definitely if you're got a podcast and you're come to terms and you're happy with your listenership but you also want to grow, do some Google searching about how to launch crowdfunding campaigns because it's exactly the same way you would relaunch your podcast.

Tim Bornholdt 23:54
Yeah, I think I've been doing my show now, we're almost to 100 episodes now.

Ryan Estes 24:00
That's amazing.

Tim Bornholdt 24:00
Thank you. I think so too. And I think like, it's so hard. I think everyone's their own harshest critic, but I feel particularly harsh on myself and I feel like I get done recording an episode and I'm like, oh, man, I should have said this, I should have done that. I didn't do this. And then I go back and listen to an episode from a year ago and I'm like, I don't even remember like, Who's that guy that's hosting the show. Like the questions that I came up with, the content is actually like really good and valuable. And it's like I think you know, I've always been of the mindset of you know, you can just go out and shake enough hands and you'll drop enough attention but you know, if you want to get critical mass, you know, that whole system you know, knowing how to get, I don't want to say game the system but just knowing how to optimize for the algorithm and dropping all those reviews all at the same time or in the event of like Kickstarter is to get everybody to donate money right on day one and have a huge start to it, is like you know, most crowdfunding campaigns, all the money either comes in on the first day or the last day. And so you really need to make your money right out of the gate, or else you're going to just flounder in that kind of, you got a $10 in, you know, bid here and a $10 bid there. It's like, if you get a rating and review here or there, you know, it's not like it's nothing, obviously, it's better than nothing. But if you can condense all of that into one concentrated attack, that's going to be the thing that pushes your needle and gets you into the some of those lists that more people will find you organically.

Ryan Estes 25:24
That's so true. That's so true. You know, and like, as much as it you know, you said vanity metrics, and unfortunately, we're kind of vain people. People will look and they're like, Well, how many ratings and reviews does it have? It's like, well, I mean, it's in the top 20 categorically, if it's podcast, so what you have to do is just make sure that your ratings and reviews, it is important, unfortunately, is kind of also onpoint with the quality that you're putting out there. You know, it's not the only important thing. But if you can get 30 people to really do it for you, it makes a gigantic difference.

Tim Bornholdt 26:09
What do you think about you know, other ways of increasing listenership? You know, I think a common way is to keep going after bigger and bigger names with audience like, you know, people that have big audiences attached to them so they can promote your show to their people. Are there any other tricks and tips that you could deploy in order, if you already have a show, and you've launched and you're in a decent position, but you just want to continue to keep fueling the system? Are there any other kind of, you know, secrets or things that you've seen that have worked successfully for others?

Ryan Estes 26:39
You bet. I mean, celebrities definitely do help, you know. Celebrity guests are great. But obviously, those are kind of difficult to secure. You know, celebrities are going to expect compensation for going on for interviews, for sure. So will athletes. So I found people have success tangentially to celebrities, which be maybe their spouse or partner, you know, or dig up some IMDB about an actor who maybe doesn't have the accolades that they want. Show interest in people that are tangentially connected to people that cast a long shadow, and be interested in them and what they're doing as opposed to their relationship to whatever star power there is. Again, it's kind of unfortunate that this vanity stuff is really what drives people. But you know, it's like game the system a little bit, you know. They listen to a couple of podcasts with you with a name or association to a name that they're comfortable with. And then they're like, I like this show, I like this host, I like what this person is doing. That's a good way to get people in the door, you know.

So as far as like, this kind of goes against my general principles of marketing, which would be kind of like starting at the bull's eye and making a spiral outside, you know. So crowdfunding is great with that, because you start with the people you know and love that will definitely do it. And then you get them to do a rating and review. And then you ask those people to ask the people that they love on this specific date to give a rating or review and those people and so on. So you're moving from familiarity to like, kind of strangers as you move out, which is, again, part of just a launch strategy. But when you're past that, you know, finding people tangential to celebrities and interviewing them with earnest and curiosity inwhat they're up to, is a great way to kind of harness some of the star power that might draw kind of additional audiences.

Tim Bornholdt 28:32
Yeah, I think keeping your core audience in mind is helpful for that too. But for me, what's been at least helping move the needle from my front has been looking for people that I'm interested in. And I think a lot of times, we don't get approached with a whole lot of requests for people to have them come on our show. But like, I think a lot of times you can find the, like, if you have a genuine interest in a guest and you reach out to them, and they've you know, they're like a, everyone's a micro celebrity these days, you know, everyone's got like 1000 followers on LinkedIn, or Twitter or whatever. So it's, you know, you can find people that have those kind of smaller audiences and just kind of work your way up to get bigger, bigger and bigger people. It's like, you know, if you listen to Tim Ferriss's early podcast, it's not like he was immediately interviewing, like Arnold Schwarzenegger, and, you know, just big name people. It's like he started and kind of worked his way into it as well. You can do the same thing. Like don't try to go after getting Barack Obama on your podcast right out of the gate. It's probably not going to happen until you've like gone through a much more, a much different, you basically have go through the process and become the kind of level of podcaster where you can attract huge clients like are huge interview guests like that.

Ryan Estes 29:47
Which would be Mark Marin, that was a benchmark day for podcasting when he interviewed Obama. Or Tony Bourdain, he interviewed Obama. It's not impossible.

Tim Bornholdt 30:00
Absolutely not.

Ryan Estes 30:01
But yeah, no, I like what you're saying, though, you know, as, as opposed to going for like breadth of like people that have lots and lots of followers like go for depth, which is if you are really into something, find somebody an expert on that. So you guys can take a really deep dive. Because people love hearing other people nerd out on stuff that they love too, you know?

Tim Bornholdt 30:23
Yeah, absolutely. And that's the thing is the big thing, the big secret, the big trick with podcasting is, you really have to know that it's an authentic game, like people can sniff it out if you're being inauthentic. And if your podcast is just like, welcome to entrepreneurs, duh, duh, duh and you're in like, clearly, it's just a big ad for whatever you're selling, people are gonna tune out immediately. You gotta actually want to do this. And podcasting is not easy. I mean, you could probably speak to that, of like, how much prep work goes into talking to somebody. And how, like, how many interviews you have to have before you're comfortable with just meeting someone for the first time and jumping into a conversation with them.

Ryan Estes 31:05
Yeah, I agree. There's a lot of trust involved, you know. Someone comes on your show, and they're gonna be a little bit nervous, you know, and it really does become on the host to kind of comfort them, at least, like, guide them through a conversation well, you know, which can be tough, especially if they're not giving you a lot to work with, you know. One or two questions or answers to questions, I definitely had that many a time. You ask someone a questionable and they're like, yes.

Tim Bornholdt 31:33
That might, that might be an interesting, like, topic of discussion, too. I mean, you've been on a lot of podcasts, and just by the nature of your work, I'm sure you've interacted with all kinds of hosts and shows and stuff. Are there any, like key indicators or key areas that you've seen, like, oh, yeah, this is gonna be a good person, like for my client to go on their podcast, or, like, if you get someone like the other way around, like, I want to start a podcast, are there like, kind of key indicators, where it's like, yeah, you'd be a really good podcast host versus maybe you should be a blogger.

Ryan Estes 32:04
Yeah, I think it's just people that talk, you know. Us talkers, podcast was just like our natural fit, you know, cuz we're gonna, we're gonna just deliver ear beatings to everyone we find anyway. So this gives us opportunity to do it. And I think people that also just, I don't know, there's kind of a twinkle in your eye for some folks, you know. That's a hard one to communicate to people asking for tips on how they can give their best performance. But really, it's like, Be playful. You know, and I think those people are naturally drawn to podcasting. It' might be an inherent trait, though. I don't know, if you're trying to work on being playful in conversation, if that's an area that you can improve on? I'm sure it is. I'm sure it is.

Tim Bornholdt 32:51
Yeah, I mean, so my wife and I have been through the pandemic, getting really into RuPaul's Drag Race. And I mean, drag queens are like, it's just a whole phenomenal like industry of entertainment that I was not experienced with, you know, besides just like, Oh, it's a guy in a dress, you know, but it's like, so, so much more than that. And when you've watched 13 seasons of the show, and you see the progression of not only you know, the first season two people are wearing looks where it's like they're wearing jeans and a T shirt, and it's like, come on, you know, like versus now where it's like everyone who goes on has like immaculately designed dresses. And you look at the personalities of people in season 1 versus season 13, you can tell the kind of people that are make for good drag queens, and frankly, I think what I've experienced, which applies to podcasting, as you alluded to this too, is do they make you feel comfortable? I think I've listened to enough podcasts where you almost kind of go in with like, you want to listen to the content and you want to absorb what's going on, but you're just not confident that you're going to be carried along this path and feel comfortable with who's guiding you along that journey. And when I'm looking, when I'm talking with people about them starting podcast, it's like I can tell right away if there's going to be like if the person is going to make a good host is if I feel comfortable just in a normal conversation with them that we can just you know, riff and just kind of bounce ideas off each other and let the conversation flow organically. And people that are really like type a you have to stick to the script you have to do it. It's like you know, maybe you can make an NPR style podcast but the the kind of podcasts that we're talking about with like this interview kind of back and forth banter, you do really have to just be good at being relaxed and comfortable and being confident enough to carry someone on a journey to get their message out as well as get what you want out the door as well.

Ryan Estes 34:42
Yeah, totally and do some prep work. I mean, there's some good journalistic questions that if you've been spacing out and you're in a pinch, you can always ask those such as like, Hmm, tell me more about that. If I ever asked that, that meant I was like thinking about my laundry or something and totally didn't hear what the person was saying, you know.

Tim Bornholdt 35:01
Oh god, yeah. Tell me more about that. No, I'm just kidding.

Ryan Estes 35:05
Or kind of what you were saying is like in the shower the next day like, Dang, I didn't even cover the book that they were launching at all. I blew it. So I found who was it a 10% happier podcast host, what's his name? Ah, Dan Harris. Dan. Dan Harris has great closing question, which is like, Is there anything I should have asked you, but didn't? And then if they're like, No, that's about it, you're like, I wash my hands of this. I did a good job.

Tim Bornholdt 35:36
Llet the door open for you. Yeah.

Ryan Estes 35:39
You know, so that's helpful. And part of the thing that we talk about with our clients, because we're really working on the guest side is that, you know, there's gonna be times where great hosts have off interviews, and there's gonna be times, you know, everyone's trying to get better, but you're gonna have podcasts interviews, they got a great show, but they're not great at interviews. And so, you know, be prepared to run the interview, so to speak, you know. I mean, you're very talented at like having conversational style interviews, but not everybody is, you know, so if you're kind of sitting on your heels, like waiting for people to lobby softball questions, man, you could have a really uncomfortable podcast, you know. So kind of, kind of be ready. We do a little bit of preparation for folks. It's an optional kind of service, but you know, we call it story crafting, and we'll help people kind of tee up some of their best material. So in case it gets weird, they can go to where they're most comfortable.

Tim Bornholdt 36:37
Yeah. And it is like, I think, regardless of which way you approach this equation, whether you're a guest or whether you're a host, preparation is really important. And being able to, you know, steer a conversation or know when it's time to pull the ripcord. I mean, I've had a couple of podcasts that we've recorded, I think, there's only been a couple that we haven't actually aired. But those ones it was like you could just tell it was a curiosity, I thought this person would make a good guest. And then for whatever reason, maybe I didn't eat breakfast that morning, or like something was off. And then the chemistry just isn't there. And it is a specific skill set that you have to foster with doing podcasting where it's, you know, I think with other kinds of marketing capabilities that you have with, you know, again, blogging, or social media or email marketing, you know, podcasting really sets itself apart, because you only have one sense that you're able to draw on for people. Like you really have to be good at captivating someone's attention and be able to get a story across and paint that picture with words. And a lot of times you don't, you know, with a blog, you can throw in a chart if you need to illustrate something or you can make a video if you want to have you know, put that on top of podcasting, I guess. But you know what I'm saying like, you got to be able to have that, I guess I lost my train of thought, which is how it always happens on this show. I seem to start ranting and then I just start thinking about laundry and what do you think of that? Tell me more about that.

Ryan Estes 38:06
No, I know exactly what you mean, which is being concise with your words. It's difficult, and it's a real skill to have. You know, if you're a blogger, you throw that copy through Grammarly. You're like, dang, why can't I write? You know, if you ever have your podcasts interviews transcribed, it's very humbling. You know, it's like, wow, I don't even speak in complete sentences. I'm just like you, actually everybody is. You ramble on, there's no commas or periods, there's maybe some dashes, if you were to transcribe it. So learning to speak definitively and create pauses in kind of the way you talk is really important. And it's a very hard skill to do. It also might come off kind of stodgy if you listen to it that way. I mean, there's something about conversation that is kind of a momentum thing, you know, that people are used to and all these filler words that I use that I'm conscious of suddenly, like, you know, and, like, over and over again.

Tim Bornholdt 39:13
Mine's just stammering. I start doing that. And then yeah, you just start going down the road and just you're very aware of all of those things once you start listening back to yourself.

Ryan Estes 39:24
Oh, definitely don't think of it while you're saying it either. That's absolute complete disaster. Which is kind of where we found ourselves now.

Tim Bornholdt 39:33
That's that's okay. I mean, I think it's that just like right now I'm stammering and trying to find my way back into a topic of conversation. And it is hard. It's really hard to be concise. And one thing I was gonna say you were talking about the transcription thing, oh man that's like that and people when they first, I think the the two biggest rookie mistakes is looking back at your transcription the first time and seeing how many times the transcription engine just freaks out and stops, because you stammered on and made no sense. And it's just one long, one incredibly long sentence. But then yeah, the other one is going the opposite route and going in and taking out every um and ugh you know, and making it sound so clean and robotic, it doesn't sound natural. And again, it's the whole authenticity piece, you have to be comfortable with your flaws, however they are and you get better as time goes on. You learn how not to stammer and not to use those fallback filler words. But yeah, it's a big process. And that's one thing I would advise if you're getting into podcasting to keep in mind is, it's really a new craft you have to hone. It's not as easy as just picking up a mic and going, you know. It kind of is, but if you want to be good at it, you have to put in the work.

Ryan Estes 40:49
No, 100%. And also, I think that there's something beautiful about stammering because I do it. And it's trying to find common ground with who you're talking to, especially if they're a stranger. You don't necessarily know if they're gonna agree or disagree with with you. If you're making definitive statements and speaking concisely, then you're basically creating a hill that maybe you might have to die on. You don't know how much that person you're talking to is opposed to that. So you know, you could say, You know what, I really liked the color red. And like, maybe you should stick to that. But most people be like, No, but I mean, I like blue. And purple is good. If you like black. I mean, if you don't like red, that's cool. I'm not saying that. I'm not saying that you don't like red? I'm just saying that sometimes I like, I mean, I don't even know if I like red. I mean.

Tim Bornholdt 41:36
Oh, yeah. Nobody wants to listen to that.

Ryan Estes 41:37
Everybody's hedging all the time, you know, but it comes from, like, an endearing place. And something that's very, like beautiful about podcasting, I think is that its essence is to, like, join people on common ground. So with all that hedging and like, not creating definitive statements, what you're saying to the person is like, Hey, this is who I am. But I'm also totally cool if you are, if you happen to be the kind of person who's like that. And if you're not, that's cool, too, because I think everything is okay. Not that I think everything is okay, but so you know that I think everything pretty much is all right, you know, so we'll keep stammering like that on and on and on and on. Which can work. You know, for people again, if they're thinking about doing a podcast, do not be the podcast that edits out all the ohms and ahhs. That will kill you. Yeah, rather, what you do is you record a preliminary interview, and then you record another interview, and you let them know the agenda, what they're going to speak to, and what they said before, and make sure that they know what they said, so that they're confident. And then you ask them to walk through the interview slowly, speaking 15% slower than they normally would. And then you get all of the really confident definitive statements that you can cut out and edit to in a blink to oblivion.

Tim Bornholdt 42:56
That's beautifully said. That's the worst part of this job, I think is pulling out those poll quotes of finding something for social media that is clear and concise and makes a lot of sense. Because a lot of times you do get the rambling and you have to kind of, you read the transcript, and it is a lot of dashes, where people are quantifying what they're saying or hedging what they're saying. And yeah, it's a lot easier said than done. And also talking slowly is not something that I've, I feel like I don't talk very fast, but then you get excited. And that's the thing with me and podcasting, I'm just, I just get so excited interviewing people and getting to know about people and it's just so easy to get off on a tangent and start rambling and going super fast. And then whoever's listening to this on 1.75x, all of a sudden, is completely lost and has to rewind to hear what I had said again.

Ryan Estes 43:46
Yeah, it's true. It's true, but I mean, I like that energy. You know, I do like the calm energy too. If you're listening to NPR, you know, but it also seems like NPR is trying to like hypnotize you with their voice. If you listen to Sam Harris, he's definitely trying to hypnotize. He's doing some kind of witchcraft with his voice. You know, yeah. But I love that. I admire people that are virtuoustic with their voice, and speaking intentionally slow and clear is very difficult, you know, so people that go that route, hats off to him. I like your style a little bit better. It's a little more bebop, you know what I mean? It's a little more up and down. Like let's get this energy moving into the conversation. Right? And it works. You know.

Tim Bornholdt 44:33
I mean, for my philosophies people are giving me an hour of their time when they listen to this podcast and I want it to be, if they got nothing out of it, at least it was entertaining and I looked like a buffoon and they got some smiles out of it. You know, that's fine by me.

Ryan Estes 44:46
Yeah, totally. No, I agree.

Tim Bornholdt 44:49
You know, one last kind of, probably should have led with this topic actually. Now that I'm thinking through this, but you know, that's okay. That's what happens when you just jump around without really looking at your script. I think a lot of times, we've been talking about podcasting, the power of podcasting for your business. And, you know, I'm doing this myself. I get to make really meaningful connections with people. I get an hour of uninterrupted time with people, which is, which is insane to ask for in this kind of environment that we're living in. But I'm really curious to hear from your perspective, what are some of the biggest reasons that people should start their shows? And then on the flip side, when do you talk people out of starting their own shows?

Ryan Estes 45:31
Ooh, that's a good question. Maybe I'll start with that one. I would talk everybody into starting their own shows. I would also give them the advice not to judge the show until the 100th episode. And you, my friend, are getting dangerously close to that judgment.

Tim Bornholdt 45:48
I am so excited to judge this show. You have no idea.

Ryan Estes 45:54
I think everybody should start with their friends. You know, there's something magical that happens when you hit record, especially if you have headphones on, you know. The friend you're talking to may be across the table, or maybe on Zoom call, suddenly their voice is in the middle of your brain. And there's no distractions, you know. They're not looking at their phone halfway through your conversation. They're forced to respond to you in time, because if you both care about making a good episode, then your attention is there. And that's a very scarce resource, obviously, attention, especially the ones of the people that you love the most. Those are the people that you tend to take advantage of the most, not in a negative way. But generally, like you can kind of trail off and go look at your phone in the middle of a conversation. So you know, interview your friends, talk about something, figure it out, record five episodes right to the Voice Memo app in your phone, you know. There's a big thing that happens with creative people, which is they kind of get addicted to the idea and addicted to thinking of the idea, and someone might chew on building making a podcast for six weeks, and they're going to spend a couple $1,000 on equipment, and they're going to get the website and this and that, and the logo will look like this. That's all just spinning your wheels, you know. Find five people that you can talk to, and record a conversation with them. If the conversation is good, it's not gonna matter the fidelity of their recording, you know. You can publish that and launch your podcast, just get it done. You know, if you're the kind of person that can't do that, and you really just want to fall in love with the idea again, I mean, maybe I was gonna say that you shouldn't do it. But I don't ever want to be a discouraging force for podcast. I think you should go ahead and do it. I think you're just end up with a lot of dusty podcast equipment.

Tim Bornholdt 47:41
I think that's reasonable. It is something with podcasting, the advice I frequently hear is give yourself, like a 10 episode trial, like just commit, commit to a number that you say, I'm going to do 10 episodes, or 15 or 5, whatever it is, but just commit to a number and see how much you've improved from episode one to episode x. And then make the decision kinda like you said, you can't judge until you've done this 100 times. You know, I remember starting my podcast, we went the route of doing 10 evergreen episodes, that were just me and my business partner, and we were just talking into a microphone. And it was, I thought it was a blast, because I've always wanted to have my own radio show anyway. So having a podcast is like a cheap way of getting into that, you know, fulfilling that childhood dream of mine. And then, you know, we started interviewing guests. And it started with just people we knew. And there is something magic about getting to, like, let somebody else shine for a little bit and help shine somebody else up. So you can, you know, help them promote what they're doing and hear their story. Because I guarantee you when you bring, especially in a business context, if you have a client that you bring on to your podcast, and you start asking them their story, and you start asking them other things, you will learn something new about these people that you've been working with for years. And every time I bring on a client, it's like my favorite time because I get to rebuild that relationship that I got to build with them early on in this whole process of building software. So yeah, I really like that advice of start with bringing on your friends and just hit record and see what happens. I bet it's, I bet you'll actually really get a kick out of it.

Ryan Estes 49:19
Absolutely. Start with a bottle of wine. You know, make it a little sloppy the first couple episodes. Figure out that beats you want to you know, ask them about that 100 bucks they owe you, that you haven't talked about a couple years.

Tim Bornholdt 49:32
Oh, yeah. Right out of the gate with the gotcha journalism. That's exactly how you have a good podcast.

Ryan Estes 49:38
That's how it goes. Yeah. No, I really I think everyone should try it. You know, and the folks that it sticks with it, it'll serve you well.

Tim Bornholdt 49:48
I agree. So last question. Because you know, we can't talk about podcasts without talking about podcasts. We're already meta as it is. So we need to go meta meta. What are some of your favorite podcasts? What are you listening to these days?

Ryan Estes 50:01
Oh, that's a great question. I have been really enjoying music podcasts again. I really like to live qualities podcast. That's a great one. I love quest loves podcasts. He's got a great show. I've been listening to hooked on pop again. That's a good one. And then of course, Song exploder, which is probably the definitive podcast in the genre. That's a good one too. But I've been really enjoying kind of musician, music podcasts and also what's the, not the champs, the drink champs. Every once in a while, I'll put the drink champs on because listening to grown man, just get totally hammered, is kind of entertaining turns out. I've been listening to a lot of 90s rap artists podcasts.

Tim Bornholdt 50:59
Nice. So this might be embarrassing. I'm going to do it too. Can you pull out your phone and tell me like in your podcast client right now what episode of what episode or what podcast is, if you were to hit play would be playing right now?

Ryan Estes 51:12
Okay, it's the healing power of pop by switched on pop. I don't know if you're familiar with that podcast, but it's like,

Tim Bornholdt 51:20
No, I'm not.

Ryan Estes 51:21
It's a ethnomusicologist and a songwriter that interview different folks. Usually they're doing kind of dismantling pop songs, whatever, like glossy pop songs is hot at the moment, which is really interesting to hear their takes. This particular episode is about like anxiety and depression. And it's kind of prevalence in pop culture lyrics right now, particularly like kind of like the very see say, they're not making metaphors. They're like, I'm taking medication for depression. And that's like the first verse. So that's what this episode was about. It was pretty good. It was alright.

Tim Bornholdt 52:01
I wrote it down. I'm gonna have to look into it. What's your podcast player of choice?

Ryan Estes 52:07
I use Apple.

Tim Bornholdt 52:09
Right on.

Ryan Estes 52:09
I use Apple podcasts. Yeah, I've, you know, I've done everything else but I just end up back there for whatever reason even though they kind of disrespect podcasting kind of.

Tim Bornholdt 52:20
Yeah, you know, that's how it goes. I'm an overcast man myself. I just pulled out my phone because I figured, fair is fair. So the episode I was listening to is from The Office deep dive, which is hosted by, I don't know if you ever watched the office, but it's the guy who played Kevin Malone on the office.

Ryan Estes 52:38
Nice. The HR guy?

Tim Bornholdt 52:41
No, the accountant.

Ryan Estes 52:43
Oh Kevin, the bald guy.

Tim Bornholdt 52:45
He did it like as quick series with Spotify, I think it was, and then spun out his own show after doing that thing. And he brings on like producers and all this stuff. And so I'm listening to an episode with him and Ellie Kemper and she played the receptionist Erin, who is in like later seasons and it's just, it's hilarious and it's so like, I feel like a bad podcast consumer because you feel like you should be consuming like business podcasts and self help and getting better and stuff. But lately, I've been so stressed out and overwhelmed with life that just listening to junk, like junk food podcasts, like I listened to like Stone Cold Steve Austin's podcast that I listened to the guys who created workaholics. Their podcast is phenomenal. And it's literally just four dudes sitting around like cussing each other out. They have a soundboard and it's just ridiculous. So you know, sometimes you need the junk food podcast.

Ryan Estes 53:39
It's very therapeutic. You got to put in Bill Burr twice a week while he rants with the entire world because it makes you feel better.

Tim Bornholdt 53:45
Oh, yeah, exactly. Ryan, is there anything, I'm gonna steal this question, if there anything that I should have asked you that I didn't?

Ryan Estes 53:54
And then I let you off the hook. And I'm like, No, you know what, that was great.

Tim Bornholdt 53:57
I love it. How can people get in touch with you and learn more about what you're doing with Kitcaster?

Ryan Estes 54:02
You bet. Best place is kitcaster.com, K I T caster.com. If you're interested in being on podcasts, that's all we do is we book people on podcasts. Largely we work with startup founders, funded startup founders, entrepreneurs with exits and C suite execs. But there's a bunch of resources and information there at the website, and you can definitely get a hold me there if you'd like.

Tim Bornholdt 54:28
I love it. Thank you so much for coming on the show today and talking about podcasting. I think, again, hunch to saying that there's going to be some really great content in here. Who knows? It could just have been an hour of incoherent rambling, but I at least got a lot out of it. So I'm hoping that everybody else did as well. And thank you so much for joining me.

Ryan Estes 54:45
I got a lot out of it too. Thanks so much, Tim.

Tim Bornholdt 54:48
Thanks to Ryan Estes for joining me on today's podcast. You can learn more about Kitcaster at kitcaster.com.

Show notes for this episode can be found at constantvariables.co. You can get in touch with us by emailing Hello@constantvariables.co. I'm @TimBornholdt on Twitter and the show is @CV_podcast. Today's episode was produced by Jenny Karkowski and edited by the razor sharp Jordan Daoust.

As I mentioned at the start of the episode, if you could take two minutes to leave us a rating and review on Apple podcasts, we'll give you a mention in a future episode as a thank you. Visit constantvariables.co/review and we will take you right there.

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