Creating the Greatest Show (418.5)

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Get ready to discover the secret behind engaging, curiosity-filled interviews as Mike shares the stage with the brilliant Casey Cheshire on his podcast, Creating the Greatest Show.  This enthralling conversation is sure to equip you with the right strategies to navigate interviews, ensuring you create memorable moments with your guests. This episode promises to take you behind the scenes of Mike’s own show, How Did It Happen, guiding you through the art of making your guest curious about themselves. It’s all about the right balance between patience, humility, and well-crafted questions.

Together, Casey and Mike delve into the first essential 20 minutes of an interview. They confront the initial barriers, including guests’ reluctance to appear boastful and the challenge of formulating engaging questions. The aim here is to stimulate enlightening conversations that captivate both the listener and the guest. This discussion also sheds light on the art of building rapport and stimulating curiosity, transforming a simple chat into an unforgettable exploration.

Lastly, Mike and Casey grapple with the tricky equilibrium of satisfying their curiosity versus the listeners’. Passion and commitment to the topics are vital for creating engaging content that resonates with your audience. They delve into the importance of committing to your podcast rather than testing the waters with a few episodes. Mike also stresses the importance of patience and humility in formulating profound, intriguing questions – it’s not just about engaging the conversation but also about making it significant for our guests and listeners. So, buckle up for an exciting journey of discovery in the world of podcast hosting.


Key highlights:

  • Strategies for Great Interview Podcasts
  • Navigating an Interview’s First 20 Minutes
  • Podcast Etiquette
  • The Role of Curiosity in Hosting
  • The Importance of Engaging the Listener

Connect with Casey Cheshire:


Check out the video version of this episode below:

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Episode transcript below:

0:00:00 – Mike Malatesta

Hey everybody, on this episode I am reposting an episode that I was a guest on, a podcast I was guest on called Creating the Greatest Show. 


It’s hosted by Casey Cheshire, and on his show he talks to podcasters about what it takes to make a great podcast, and ultimately, that comes down to what it takes to have great conversations with people that lead to great takeaways for the people who are listening, and so I was very, very proud and pleased to be a guest on his show, and I thought you would enjoy it as well. Here are a few things that we talk about. We talk about breaking away from prepared narrative, and this applies whether you’re a podcaster or just a conversationalist, for that matter. So breaking away from the prepared narrative, building rapport with your guests, the art of crafting, engaging questions, and I think the number one thing that was most interesting to me and hopefully will be for you in this episode is this whole notion of making the person you’re talking to or speaking with get curious about themselves as a result of a question you asked them. So I hope you enjoy this episode, and here it is. 


0:01:15 – Casey Cheshire

What a cool con we’re going to have. We’re going to be talking podcasting, we’re going to be talking about all sorts of things here. I’m excited. I don’t know what’s going on. I’ve got notebooks, I’ve got pens, I’ve got iced coffee surrounding me right now. I can’t wait to introduce our guest today. He’s an absolute badass. What can I say? Serial entrepreneur, successful entrepreneur, seasoned podcast host, he has actually pivoted multiple careers and, after being successful with his companies, he’s now really focused on the dream exit, helping fellow entrepreneurs exit in that dream like way, not in the opposite, not in the nightmare way. He’s been featured in things like Forbes, the entrepreneur magazine, all sorts of places. What is his show? That’s what we’re here to talk about the show he’s a creator and host of how Did it Happen, which now has over 440 episodes as of a few days. Who knows, that number is probably doubled by now. Author of ownership and a dream exit expert, mike Malatesta. Welcome to the show, sir. 


0:02:16 – Mike Malatesta

Casey, thank you so much for having me on. Thank you for the help that you’ve given me and a couple of conversations that we have. Thank you for being so excited that you bumped your mic. 


0:02:25 – Casey Cheshire

I did. I didn’t even start it. That’s enthusiasm. Everyone listening is like what was that? That just happened. 


0:02:30 – Mike Malatesta

That was me running into my mic. That’s all the caffeine from those iced coffees, yeah exactly right, crazy man, I’m glad you’re here. 


0:02:38 – Casey Cheshire

We get to geek out about this thing we both love. For the next bit of time here, I want to start the show the way we start every show by asking you this question, mike, pull back the curtain for us on your show and share your most important strategy for great interview podcasts. 


0:02:54 – Mike Malatesta

Yeah, sure, like you said, my show is called how Did it Happen? I do two things on that show. Once a week I have conversations with really successful people from all walks of life. I have two intentions with those conversations. One is to get to the root of how it happened, how their success happened and however they want to define their success in. Two is get to the point of why it matters to you. If you’re listening, then on the other show that I do, the other episode I do so I do two a week is what I call Free Thinking Friday. On Free Thinking Friday, it’s just me. I do a solo episode that’s like 10 minutes long or so about something that has interested me in the last week, something that I’ve been made aware of, something that I’ve read, something that I think was cool and that I think the people listening to me will also think is cool as well. That’s the show. I’m going to focus on, the conversations I have with successful people. 


For the answer to this question that is that what I’m really trying to do, casey, is I’m trying to get my guests to be curious about themselves. I find that a lot of people who’ve been on podcasts especially people who’ve been on podcasts or a lot of podcasts, like executives and other professionals. They show up kind of wanting to control the narrative around their conversation. They’re pretty good at it. I prefer to try to figure out a way to get them to actually think about something about themselves that they weren’t thinking they would have to think about and they weren’t, maybe weren’t prepared to talk about. But not, I’m not trying to, it’s not a gotcha, I’m not a gotcha type person. It’s really an organic sort of oh Then kind of when the head goes like tilts, a little bit like that, then I feel like we’ve sort of broken some new ground. I really like to get to that new ground where the guests is curious about themselves. 


0:05:02 – Casey Cheshire

Wow, that’s like the aha moment, king, at that point You’re creating these little, these moments, but that can’t be easy, right? It’s almost like the folks that are in control to your point and are good at it, that it’s almost like they requires what Vulnerability. They require a lot of different things that people probably don’t come prepared to bear their souls on your show, or do that. 


0:05:30 – Mike Malatesta

So I think there are some that some people are in the business of bearing their souls. 


So some people are quite ready for that. The vast majority aren’t. Not that they’re unwilling, they just aren’t because they haven’t been, they haven’t had to. So I like to think of it as, when you get them to be curious about themselves, you end up going off in a different direction, perhaps with the conversation, and they don’t even know any longer or feel any longer like they’re on a squadcast or a Zoom or on a podcast at a hall. And I’m not suggesting I get there with everybody because I don’t. But man, when you do, that’s where the like some people will call that, that’s the real goal and that’s where you have a great podcast and the person when you’re done is like I just never thought I would be talking about whatever it was today, but they’re happy they did. 


0:06:45 – Casey Cheshire

So what is it about those unscripted moments that are so magical? Why do you pursue the? I mean, it’s not just rhetorical, but like what is about those moments that is magic to listen to and also magic to be a host of. 


0:07:05 – Mike Malatesta

Well, to me they reflect the reality of life as a human being. I mean, how many people do you run into somewhere and you start? You open up a book and you start asking them a list of questions? That usually never happens. So what normally happens is I run into you, casey, hey, hey, I’m Mike. What do you do? Where do you live? Where are you from? Where’d you grow up? And the answers to those questions lead to another question and I have no idea what that question is going to be. And even if I had the questions in mind, I still wouldn’t make sense to logically follow a list of questions. When you’re getting answers, you’re getting feedback, you’re getting direction from the person you’re talking to. 


0:07:54 – Casey Cheshire

I definitely find that tends to be like a new host thing. Right, you have a list of 30 questions and you’re just going to attack that list and the worst sin of all, at least with question asking, is to hear that answer they give. And great thanks, Mike. Your next question is this Maybe the gold was passing you by. They just mentioned something really interesting and you just let it slip by to ask another question, which would probably be dumb and probably not even a good question, but instead there was something right in front of you. So it seems to be an experienced host thing where somehow you’re able to let go of the reins, to sort of roll the dice. Talk to me about that. Have you always been like this or did you evolve into it? 


0:08:42 – Mike Malatesta

Yeah, I evolved into it, I think, and I put myself back in the shoes of, say, the first 50 or so episodes that I did. There were two things that were always on my mind. One is I’m going to hit a brick wall with this person at 15 minutes in and I’m on an hour show and I’m not going to know where to go. So there was always that fear. So I would have a list of prepared questions when I first started, not with the intent of asking all of those questions, but with the preventative measure of like, if we get stuck and we have got nothing, I’m going to go and I’m going to ask them one of these questions to try to get it restarted. And then I discovered over time that I never asked any of those questions. I never asked any of those questions. So then I began to well, two things. So I began to abandon that. 


But I also learned one thing that if I get 20 minutes into an hour conversation with somebody, it’s going the hour or more. There’s just no question about it. It was always the first 20 minutes that I was the most nervous about. So once I got my feet under me a little bit and got a little confident, I was able to get rid of the questions. So now what I do, I still have notes in front of me that I’ve made and the research that I’ve done on the person, and I just have those there because I know that there will come a point where something that they say I’ll be able to reference this and connect the two of them in what hopefully seems like an organic, natural way. So that’s been my evolution and I don’t write any questions any longer. 


0:10:57 – Casey Cheshire

Do you have like a couple of go-tos? I mean, do you go to or like nothing completely unscripted? Have you gone completely? 


0:11:05 – Mike Malatesta

Yeah, I’m completely unscripted, except for two things. One, the beginning of my show I ask everyone how it happened for them and I ask that question very. The way I ask that question is very intentional because I don’t have conversations with them about the answer to that question prior to, and the reason I don’t is I get asked a bunch how do you want me to answer that? And I always say the best answer is the one that you want to select to answer that. Now you could say well, what if the person goes off on some wild ride? That makes no sense. That’s a risk. 


But I found that, at least in my experience, very few people do that. They have a story that they want to tell and I don’t want to put any thoughts about what that story is into them, because then I am kind of scripting them the podcast and then I’ve taken to this more recently. But at the end and I think I’ve sort of copied this from Tim Ferriss I asked them If there’s anything that I haven’t asked them or that they would like me to ask before we end the show, and I and I like doing like he. He does that and I liked that it often brought up something that I hadn’t thought about, which is but his, you know, value to leave with the listener, and so, and it’s a simple question, they and they can eat. They can say no, I think we got it all and I’m like great. 


Okay and then, if they want to, it’s just that one thing that you know, like I didn’t connect that dot or I totally missed that part, or whatever, and it’s Makes a good ending. Yeah, I think it a lot. 


0:12:58 – Casey Cheshire

I mean some guess will. I’ve been on shows where I had a point. It’s like gosh darn, I’m gonna make that point. You almost like a politician right where they’re like they ask you one question. 


0:13:08 – Mike Malatesta

Oh yeah cool. 


0:13:08 – Casey Cheshire

Let me finish my point over here, and then I’ll get to your question. So some guys will just do that. But I love the idea that some won’t. Some will just go with you wherever you’re going and and asking them it’s almost like a little bit of a clearing Session. At the end just say are we good at anything left unsaid? You don’t want to leave it like that. That’s a cool question. 


0:13:26 – Mike Malatesta

Yeah, and it makes it. It makes it Not like an interview. It makes it to me it like takes a little bit of the Well. Hopefully the interview thing is gone by the end, but if it’s not, it’s like here’s an opportunity for you to, you know, help me out here with something that is important to you, and I’m not talking about promoting their website or their. 


Course or anything. I’m really not trying to get at that. I’m trying to get at some Lesson story, advice, whatever that could be helpful to to me and to everyone listening. 


0:14:03 – Casey Cheshire

Yeah, you know, this is a good Topic too, because if you and you said, you don’t do the prep, right, no prep Call it’s it’s rare emails you just like get on the show. Let’s go. 


0:14:17 – Mike Malatesta

Oh no. So our, our process is very detailed. So when, once we, once we book, so we sense everyone an invitation and in that invitation it describes Exactly how this is gonna go, you know the time, the type of equipment we would love you to have, how, the how. I’m gonna ask that start. It’s an unscripted podcast. I’m gonna start with how did happen for you and so it’s. It’s very detailed that way. But but I don’t usually get on the phone with With or a zoom with people beforehand. 


0:14:54 – Casey Cheshire

Yeah, okay and so, but you do, you are giving them information, but to your point. You don’t want to script their answers, you don’t want to Manipulate them. And also, I mean the thing that I have to, the challenge I have to deal with on a prep call, it’s making sure you don’t just a runaway and say the whole show on the prep when we’re not recording. 


0:15:13 – Mike Malatesta

Well, yeah, yeah, right, right and that’s one of the, that’s one of the, and I think I, I think when I heard you at Dave will, that was one of the things he said, because you guys were debating Prep call, not prep call, and he was sort of like I Think you both had good points because he was sort of like I don’t want to do what you just said, I don’t want to hear the stuff that I want to come out on the podcast. But your point was I Want to get started right, yeah, and that made a lot of sense to me too. So I’m, I’m not, I’m, I’m rethinking it, but I don’t know which way I’ll do it. But but you’re, you’re, the prep call makes sense to me if, if, if it’s got a tight agenda and you’re not going to open up the whole story. 


0:15:59 – Casey Cheshire

Totally, and you’ve you’ve mentioned this word a couple times, it’s one of my favorite words intention, and I think, for me in particular, my intention around the podcast is to create a relationship, and so, with that, having a little more time on a Unorganized prep call can be great, you know. So that it’s the second time I’m seeing you were chatting today that kind of thing, as opposed to you know, cold, stranger, let’s go. And someone like Dave Probably all of us we could probably warm someone up. In fact, I actually just did a. I did a show without a prep call recently. It was a, it was really. It was a childhood hero. It was a marketer who had been in decades championing SEO and and and how to market ran fish can. Really cool guy. 


No prep right, which you tend to get with the more busy slash Famous. You know, some people just don’t want to do them and I normally say no. If they don’t want to do a prep, I don’t want to interview them Because it’s like my rules, cool. But I said yes to him and I had to deal with which I don’t normally have to deal with on my show Warming him up, you know. So I did a little stuff before we hit record and then even on the show he’s not sure who I am just yet right. So we had to have that initial dialogue, you know, which might be tied into that 20 minutes. You mentioned that initial 20 minutes where you’re kind of feeling each other out. 


0:17:20 – Mike Malatesta

Right right. 


0:17:22 – Casey Cheshire

Tell me more about your 20 minutes it. What do you do in that 20 minutes to make, to make it to the 20, so you know you can get to the hour. 


0:17:30 – Mike Malatesta

I wish I could tell you I just try to get there. Survival yeah, what I’ve learned is that patience is Really valuable. Like, for instance, I would be nervous when I started. I doubt you know I’d be like, well, what if I asked the how did happen? Question and they give me a two-word answer what am I gonna do with that? Fortunately that’s Hasn’t happened. 


Maybe I’ve gotten one sentence from a couple of people, but that so I used to be nervous about that because I was thinking, well, how do I move on from from here? But now I’m just patient with it. So I Know that whatever they say Is gonna lead to three, four, five questions. Of course I don’t know what they are, but I know it’s gonna lead to that, casey, and then by that time we’re off in and I don’t fear that 20 minute thing anymore. So sort of like that saying you slow down to speed up, yeah, that’s kind of what. That’s kind of what I think it is. I’ve just been. I’m not nervous about somebody Knocking me off my game with their answer to that first question, like I was before. I’m just like okay, this is gonna be whatever they say. Man, it’s gonna be like let’s follow that, yeah and so so it just hasn’t been an issue for me. That’s cool. 


0:19:01 – Casey Cheshire

It sounds like you’re also, and once you deal with something once as a host right, then it’s not as a much as a surprise the second time, so to get that one sentence answer Can be scary. Once you go through you’re like well, I dealt with it. You know. I’m sure you asked some kind of follow-up, but I do wonder about those short answers. What’s your take? Why do people sometimes give short answers? 


0:19:28 – Mike Malatesta

Well, I think there’s a there’s a humility angle to it. People who are aren’t Naturally comfortable talking about themselves. Maybe they haven’t been on very many podcasts and they’re not naturally, you know, inclined to talk about themselves. They they’re used to going through life in a humble way and the humble way is Say as little as I can about myself, but be polite, you know. So, right, I think that probably has something to do about it. Or, you know, I haven’t had the. I’m sure there’s the I Don’t want to be here type person who I Haven’t had that, and I think that’s one good thing about podcasts. Is it because it’s a complete choice? 


Yeah, you don’t have to be anywhere. It’s not like someone coming up after a game and sticking a microphone in your face and you have to answer the question because they’re part of that part of the network and if you don’t answer the question, you get fine too. 


0:20:31 – Casey Cheshire

Yeah, how’d you catch that game-winning touchdown? Yeah, how did you feel when you threw that? Yeah, let me, let me know when, when you? Yeah, exactly. 


0:20:41 – Mike Malatesta

What did you guys talk about in the locker room? To get psyched up for the second quarter. Oh okay, yeah, well, let me tell you everything I said. Uh, they all. Yeah, it’s yeah. Anyway, I’m surprised that I and I know I’m going off on a tangent- yeah, that’s what we do, I’m surprised that, uh, that those positions still exist and that anyone cares. 


Right, because I get as a as a fan. I don’t get any. I get zero value out of that. In fact, I get less than zero because I can see that the coach or the player or whomever is like oh my god, and just Me. I’m like it’s no fun for them. It’s not fun for them. Why do I do it? 


0:21:23 – Casey Cheshire

Yeah, you’re like what are you talking about? Stop asking them questions. Let them just celebrate and hold the hold the cup up, hold the trophy. You know, bask in the moment, crazy, you know, it’s really interesting. You brought up that point because my theory going into this conversation when I asked the question was that sometimes people don’t answer because, you know, I’m not sure what I’m going to do with this conversation when I ask the question was that sometimes people don’t answer because they’re either not excited about the question or they don’t know anything about the question, so passion and expertise are not present. So it’s just like I’m nothing to really say here. But first question how did it go or how did it happen? These are things that a founder should have. So I would imagine it’s probably more the humility side with a lot of people you’re talking to versus you know, because sometimes you can ask people questions that are just duds. Have you had that? 


0:22:22 – Mike Malatesta

Have you ever recall any, of course, like the one I just asked you Like I, yeah speaking of recency, so I had this hasn’t come out yet, but I had this guy on my podcast named Cal Fussman and Cal’s a he’s a like lead writer for Esquire Magazine. 


He’s a big deal and we were having a great conversation and we got into and he’s about 65 or so, but I know he’s he’s, you know, into challenging himself physically as well, even though when you look at him you probably wouldn’t make that connection right away. And I just, and his whole thing is about the big questions, like he’s known as the big question person. So we had been talking about big questions sort of like this, and I asked him well, I was like, you know, you’re doing the Spartan races and you’re doing this other, these other types of things I can’t remember exactly what the events were and I’m like, does that help you as you’re going through the process of training for that or actually competing? Does that ever help you with the formulation of you know your big questions like stuff you wouldn’t think about? And he’s like, well, that’s usually happens in the shower and I was like, okay, that’s telling me that wasn’t that great of a question. 


0:23:49 – Casey Cheshire



0:23:50 – Mike Malatesta

So I thought I was going somewhere with it, but yeah, I didn’t think that was that great of a question. I don’t feel that way too often, but I wonder, now that you say that, how often do the people who are listening to my podcast go? Well, that wasn’t a great question. It may probably happen more times than I think. 


0:24:10 – Casey Cheshire

Yeah, right, because it goes to the earlier idea of the scripting versus non-scripting. At least, if you script it, maybe it looked good on paper. You know, maybe it fell flat during the conversation, but at least it sounded good when writing. But when making up a question like we’re riffing, we’re going off in these, we’re exploring together, sometimes you have those things. 


0:24:33 – Mike Malatesta

Yeah, and you know that’s you just made me think. If you have scripted questions, your natural tendency is and you don’t have patience, your natural tendency is to get to that question and you might, it might be the greatest question. You just ask it at the wrong time Because, rather than listening for when that’s an appropriate question to ask, you force the question because it’s such a great question. 


0:25:03 – Casey Cheshire

Right, and yeah, you force it early. Talk to me about the timelines then. Are there certain questions you don’t like to ask early on? Do you tend to ask certain ones at certain times, you know? Talk to me about that. 


0:25:24 – Mike Malatesta

Yeah, I really don’t. I really don’t know what questions I’m going to ask, Casey, besides that first one. Like I said, I know there are topics or things that I want to weave in at some point when it’s right, but I try to just let that happen, and there’s lots of times when, at the end, I haven’t gotten to a bunch of stuff that I thought I might get to, and it just because it just didn’t happen. 


0:25:55 – Casey Cheshire

You know that’s Does that make sense? Yeah, that totally makes sense. By the way, I would argue that was a good example of like an unclear I wouldn’t call it a dead question, but I would say like an unclear question. And I’ve often found podcasters will sort of figure it out and they’ll just make a great answer, like yours was just now, whereas that untrained person who is just literally going to take you literally and if I’m like, have you ever felt that they’d be like yes or no, right it? Just, if you give them a boolean question, I’m just going to answer it and wait for you to fill in the gaps versus a podcaster. I don’t know, there’s something to that. 


0:26:35 – Mike Malatesta

Well, again, like I mentioned, I mean when you come on to a podcast, you’ve made a choice to come on the podcast, so if that means that you’re going to answer a question with one word and make me feel like I just asked you a bad question, then I don’t know that you really showed up for the right reason. 


0:26:52 – Casey Cheshire

True, true, especially if it’s you’re trying to have a conversation. It’s not. It’s not CNN, we’re not debating, we’re not, you know, scourging each other. This is just, you know, it’s just two people having a convo about things they love. So you only, your only scripted question is your first one, and you know it’s interesting. My other show I used to ask a couple of different miles. Even now I have a couple of milestones I’ll tend to hit. But but that’s interesting because from my perspective, I oftentimes see people asking personal questions or sensitive questions too soon. Right, going right. Hey, what was your biggest failure? Hey, just met. You Don’t know if you can trust me, right. 


0:27:38 – Mike Malatesta

Right, what’s your? 


0:27:38 – Casey Cheshire

biggest failure, bro. It’s like I actually once had one person ask me on a podcast you’re so nice, but your first question was like, you know? So, like, who are you? What makes you you, you know? And so, because it was early in the process, I gave her the you know the, the polished answer, which is well, I’m a technical communicator, and blah, blah, blah. But you know people that ask me that toward the end of the show they’re getting the fact that I was a magician and I like karate, you know, like. So it’s almost like when you can warm them up and it sounds like, you know, maybe that’s something you’re doing just naturally, because it’s not scripted. You’re just sort of evolving the questions. 


0:28:17 – Mike Malatesta

Yeah, I mean that’s. I definitely want to get to who you are, so but I’ll, but I never. I never ask it that way because when I to me that question, for example, for for probably 90 plus percent of the people that come on a podcast, that’s I don’t want to say it’s an offensive question, but that’s not a question that you’ve earned the right to ask me. 


0:28:44 – Casey Cheshire



0:28:45 – Mike Malatesta

When we’re just getting started and once you do like I’ve had that asked of me and all kinds of questions, you know on these types of podcasts that I’ve been on, that you met, you sort of referenced there, and I as soon as like to me. When I get asked something like that, I’m just like, okay, lazy. Or when it’s like, oh hey, mike, why don’t you introduce yourself to everybody? Oh, lazy, you know there’s a lot of, and I’m not saying I’m right about that. That’s just how it feels to me as a guest or a listener. So I can. We talk about that for a second. 


0:29:22 – Casey Cheshire

Yeah, because I agree the whole introduce yourself thing, man doesn’t it? It’s like you asking someone to introduce themselves is not giving them. I don’t think it’s giving them the gift you think it is. You’re actually in my mind, you’re telegraphing that you didn’t care enough to figure out how to do an introduction to introduce. You don’t know Like if you can pull off the interview and make it look like maybe you don’t actually know who they are. You’re almost like a CNN. Yeah, no, I didn’t read your book. I’m just going to literally ask you four questions that anybody could have asked you. You know it. Just it transmits the wrong signals. 


0:29:59 – Mike Malatesta

Well, especially when almost everybody provides you with some sort of bio about them. That’s part of our process. Do you have a bio? Do you have a picture? You know we’d like to have these things and when I’m on shows I get, I give them, you know, the what they need, the bio theme, and so and I’m not looking for someone to like with my bio, I’m not. I don’t care if they read the bio, you know, word for word. In fact I’d rather they didn’t. What I’d rather they do is is talk about who I am in a way that makes sense to them, and then I can fill in the rest. I mean, I’m on your show for an hour or whatever, so I can fill in the rest, but I just don’t like that. 


0:30:42 – Casey Cheshire

Like I said, it to me it says lazy and it just to me it’s not a great way to to start and, to be fair, you know, if you’re listening to this and that’s the method you do, I understand you may not know or not be aware that you might be sending subtle signals, you know, to your guest by doing that. So maybe you just maybe today’s the day you start doing a little intro instead, just anything that, and I like how you said that, mike, about putting it in your own words, right, what that, what that guest means to you, far outstrips trying to ever read a bio of someone right, and to read their biography, you know their 30 volume text. 


0:31:27 – Mike Malatesta

Yeah, yeah, so I, I. I just find that it’s a subtle way to honor your guests by being able to say something nice about them. To get started, and what I typically do, as I mentioned, a lot of people provide the bio, I take portions of the bio and that those are the ones that I’m going to talk about, and then, as I’m doing it the introduction I ask them questions about something in the bio, or I interject about some organization that they’re head of that I’ve never heard of, and so I just kind of make it like my own. I try to make it my own, and oftentimes there’s a question to them in the bio, in the reading of the bio, which hardly anyone does that, but I think they like it. 


0:32:28 – Casey Cheshire

Wait, tell me more about that. There’s a, there’s a question to them reading the bio what? What does that mean? 


0:32:35 – Mike Malatesta

Yeah. So they might have like I am a certified nutraceutical, blah, blah, something right, and I’m like I don’t know what that is. So rather than just reading what they wrote you know, casey is a certified nutraceutical, whatever actually I go, I’ll say Casey is a certified nutraceutical. And they’d be like what does that mean? Never heard of that, what does that mean? And then they’ll tell me and it’s just like a little break up in the in the bio, that in the reading of the bio, that brings the guests in right away, but in a, in a way where they’re helpful to me as opposed to me trying to be know everything about them. Yeah, or I’ll say or they’ll have some designation. I’ll be like had to feel cool when you were profiled in Entrepreneur Magazine and I’ll just say it’s not like a question to them. I’ll just be like that ought to be cool. So I just try to add something along the way of the bio to give. So it’s not just reading a bio. 


0:33:39 – Casey Cheshire

That’s really cool. That’s a really cool tip. It’s like a power tip there. The idea of building in it’s almost rhetorical or just it’s like you know you’re actually asking that question or you just kind of like mentioning like, oh, that would be really cool the fact you got, you know you’re performing. Yeah, it depends. 


0:33:57 – Mike Malatesta

Depends, or like that same one. I might read that you know they were featured as whatever in Entrepreneur Magazine. I’d be like, how’d that feel? Yeah, so sometimes it’s just a comment on it and sometimes it’s just a small little question that I just think it I don’t know feels like it works to me. 


0:34:19 – Casey Cheshire

Yeah, it’s something about. It’s like a little micro signal that says I’m interested in you, right, and I know just something more about you than meets the eye. 


It doesn’t necessarily have to be reading the book from my Ethan. He will read all of your books and he’ll, he’ll outline them and he’ll bring up quotes and everything. He’s the master of preparation. But something as little as remembering the fact that you’re in Wisconsin, which is where my sister-in-law is, and I went to a concert there, you know just something that kind of gets brought up, but even better if it’s about their accomplishment. 


0:34:59 – Mike Malatesta

So I’m glad you brought up the book thing, because one thing I do if I reach out to somebody because I’ve heard them on a podcast or something and they are promoting a book, I will get the book and I will read that book. Cool, because I want like that’s why I reached out to them really and I know what they’re trying to accomplish. But on the other hand, just because someone has written a book, you know I’m not necessarily going to read the book. Every book that a guest that say came to me through a channel or something wrote I like I prefer. I think you have much better conversation with somebody if you’ve done something with their material, if you’re going to ask them about it. If they wrote a book and you haven’t read it, then I think you should say I haven’t read it and not pretend you have read it or pretend we’re going to dive deep into the book. So tell me what chapter one is all about, and then that’s your question, and then you sit back and wish and this is another pro tip. 


I got this from James Altucher, who you may have heard of. He’s got a podcast called James Altucher Show and he reads a lot of books. You can tell he’s read a lot of the books, that and he’s got some really big names that come on that expect you to have read the book. But his pro tip was, if you don’t have time to read the book, just read the beginning, the introduction, first chapter and the end. And if you don’t have time to do that, just read the end and he’s like you’ll know more than most people who are going to talk to them about that book. They’ll know because they haven’t touched it at all and you’ll be able to have a meaningful conversation about the book, maybe not an in-depth conversation, but a meaningful conversation about the book where again you’ve honored them by doing something. 


But then I wonder too, like Tim Ferriss will say, I don’t read anybody’s books, it’s just I don’t do it. And the people who come on his show often have books. So he pretty much he doesn’t fake it, doesn’t try to, but he just kind of stays away from the book unless they bring up something in the book and then he just feeds off of that, which I think is fine as well. But I haven’t reached the point where I feel I have that type of audience and the type of command that he has where he can just say I’m just not going to read books because I got my own stuff to do, but you’re still going to have a great conversation with me. 


0:37:50 – Casey Cheshire

You know what? 


do you, do I didn’t know that about Tim, because I, for the most part, tend to subscribe to that sentiment. My rationale has been I don’t want to read the book because then I’ll know everything. And why would I ask you? Because I already know everything that you just stated. And also I think part of this is too. I also don’t want to ask leading questions that I know the answer to too much. I mean too much, because I know I ask you a question at the very beginning of this show leading question. I have a general sense of where you’re going to go with it and I’m excited to hear, but I don’t want to ask you a question and that I know the answer to, which is probably attorneys do that right, like I’m generally asking because I’m curious. So I really do want to know the answer. If I’ve already read your book, I have to find other questions to be curious about. So I don’t know. 


0:38:50 – Mike Malatesta

Yeah, except that, except maybe that the people who are listening to your podcast haven’t read the book Right? So while the answer may not be surprising to you, it may be surprising to them. So I think there’s. You know, like I said, I go, I read a bunch of books, A bunch of them, but I don’t read all of them. I do feel like I’m better prepared when I read the book. 


0:39:15 – Casey Cheshire

Oh, 100% yeah. 


0:39:17 – Mike Malatesta

And, and not just about the book itself, but about them. 


0:39:21 – Casey Cheshire



0:39:22 – Mike Malatesta

A lot more usually in the book about them than their bio suggests Spend some more time with them. 


0:39:28 – Casey Cheshire

You know, my excuse is that I want to be inspired to read the book after this conversation. It could be lazy. I mean something I’ve been toying with. 


0:39:42 – Mike Malatesta

I don’t think it’s lazy. Yeah, I don’t, that I don’t think is lazy. I mean you’re asking somebody that’s a lot of work for five, six hours to read a book. 


0:39:50 – Casey Cheshire

Sure, especially if you don’t like it, though, right yeah, who do? 


0:39:54 – Mike Malatesta

you don’t like the book. Have you ever had that? Sure, of course. 


0:40:02 – Casey Cheshire

Well, I should say don’t like. I mean, there’s been. 


0:40:08 – Mike Malatesta

There definitely been somewhere. I haven’t enjoyed them as much as others let’s put it that way. But but I’m not looking. I just want to be clear. I’m not looking for people to come on my podcast because they have a book and and I want to read it. That’s not what I’m looking for. Generally, like I said, if I hear about something and I reach out to them, compliment them on their book and ask them to be on my show, then I feel like I need to dig into that. 


0:40:36 – Casey Cheshire

It’s definitely a different dynamic If you’re requesting of them to be on versus you know them just pitching you and you’re like, cool, let’s give this a whirl. There’s definitely a difference there. 


0:40:49 – Mike Malatesta

Yes, for sure. 


0:40:52 – Casey Cheshire

And I almost. It almost works better when you ask them to be on right, because you’ve invested interest. You’re excited at least, like when Rand came on my show. He doesn’t know who I am, but but I but he has the benefit of a host who already likes him. Right, I already like the guy. I’ve listened to him for two decades. So this is not going to be a tough interview. This is going to be a fun one. Yeah, at least at least half of it. You know I’m a fan and he eventually becomes a fan. It’s cool dynamic to it. So how did you get him? And I just just reached out, said hey, he did, okay, um, it wasn’t any real magic to it. Maybe you know, maybe he’s famous in a select marketing community, but yeah, just really but really cool guy. 


0:41:45 – Mike Malatesta

I mean he’s okay. 


0:41:46 – Casey Cheshire

Yeah, it’s really cool. Guy reached out and also he’s doing a new thing now. So he’s, he’s got, you know, he’s got a new SaaS app. He’s he’s doing things and so of course he could, you know, he could use the attention and the promotion as well, so there’s a benefit to him, uh, to be on. 


0:42:00 – Mike Malatesta

But yeah, just just ask him. Yeah, His name is really familiar to me. 


0:42:04 – Casey Cheshire

He just recently had a company that he sold, I think, Um yeah, he founded the SEO Moz company or, at least with his, with his family, created the. 


0:42:14 – Mike Malatesta

Moz, moz. 


0:42:16 – Casey Cheshire

It’s pretty cool, but now now he’s doing like the next phase, so it was just a cool combo. We we got to a lot of stuff, um. But now that we’re geeking out on on like how much we love it, I’m just curious is there one particular aspect you love the most about being a host? 


0:42:38 – Mike Malatesta

I love to have my own curiosity satisfied, so I want people to get curious about themselves. When, when we’re talking, but I, I just get a lot of energy out of my own, create uh curiosity being uh peaked and satisfied. Yeah, um, when I’m talking to someone and it’s and it’s evidently it’s easy to do, casey, because there’s hardly any that I walk away from where I’m like, oh, I know my curiosity wasn’t satisfied at all with that person, that that really happens. Um, so I think, as for me, as a, as a host, that’s like number one, um, I, you know, I always, I’m, I’m always trying to do work that I think is important. I’m always trying to do it as best as I can on that day. 


0:43:33 – Casey Cheshire



0:43:34 – Mike Malatesta

And I, geez, I always hope that someone else will like it, um, and get it. I think that’s the thing that if there’s anything that if there’s anything that I’m, I feel like I’ve still massively in search of, is how do I get more people to give my show, uh, a chance? 


0:44:02 – Casey Cheshire



0:44:04 – Mike Malatesta

Um and it’s just. I’m sure that that’s probably what most podcasters are Are saying to themselves is how, like, if you think you have, you’re doing good work and it’s um and it’s got a broader potential appeal than what you’re seeing in your numbers or whatever, how do you break through um and get it, get people to give you a chance? 


0:44:31 – Casey Cheshire

And and this kind of brings up that challenge of D in your intentions. Who’s more important, your own curiosity or the listeners curiosity? 


0:44:44 – Mike Malatesta

Yeah, well, um, so what do you think? The answer to that is Uh, I was. 


0:44:50 – Casey Cheshire

I wanted to know your answer before I I I you know, okay, so my answer is clear. 


0:44:57 – Mike Malatesta

If it’s, if it’s, if it doesn’t satisfy my curiosity, I shouldn’t be doing it, and so I can’t put the listener in front of me. When it comes to podcasts, I have to get something out of it before I can hope to have a chance for the listener to get something out of it. 


0:45:17 – Casey Cheshire

But isn’t it tempting then to make the listener the priority? Right Now, my answer is more like yours, because I couldn’t sit through this thing. Like, for instance, other than Rand, who is a reformed SEO specialist in the marketing community, I can’t stand to talk to anyone about that specialty on my marketing podcast. I’m just not going to do it, I just can’t do it. I dislike that industry. And other than a childhood hero you’re not going to—it’s funny, I was like 20—but other than a hero of mine, I don’t really want to talk to anyone. We didn’t talk as a CEO either, so it was like I just don’t want to do it, I just can’t do it. So there’s certain things that just don’t—that’s just—that’s anti-curiosity for me, but I’ve always felt that if I’m interested, then wouldn’t everyone else be too, which may or may not be true, you know. 


0:46:16 – Mike Malatesta

Well, you think about any type of production, right yeah, like a movie or television or a stand-up show or whatever. You’re always interested in whether the audience is going to accept what you’re doing. But you’re always best when you’ve accepted what you’re doing and you’re putting it out there and you’re hoping that it resonates with the audience. But if it doesn’t resonate with you, you just feel like there’s no way I can connect, not for long that I can connect to an audience with something I’m not sold on. 


But I really feel like you have to be sold on what you’re doing. And by sold on what you’re doing, I don’t mean you can’t improve, you can’t get tips, you can’t continue to get better. I mean it is a continuing, continuous improvement process. But if you’re not sold on the core of what you’re doing, well, you’ll be probably like most, most podcasters that end up doing 10 episodes or 20 episodes, and that’s that they’re not sold on what they’re doing, they’re trying something. So there’s a difference, right, there’s a difference between commitment and trying. 


0:47:32 – Casey Cheshire

I feel, like, I’m committed to yeah, it creates such a low energy when you’re not interested. So I do feel like it’s kind of like a table stakes that if you’re not interested, then who else is going to be. I’m not interested in making one of my I’m chasing your number, I think something like 300 episodes on the marketing pod and a bunch of this one. One of those episodes I did check out mentally and check my email and my Slack and everything else under the sun, because the guy was just so boring and I hated it. I’m not saying this is the right thing to do, but I’m confessing to you, mike, that I did this because I just wasn’t interested and instead of trying to take like an active role in interrupting him and maybe asking something different or some other question, I sort of just let it ride. You know, let him do his monologue and then I’m just going to not be there and it just. This is not good as people could imagine. It does not make the episode doesn’t get better when you do that. 


0:48:33 – Mike Malatesta

Yeah, it’s. What do they say that suboptimal yeah? 


0:48:37 – Casey Cheshire

That is less than ideal. Quite suboptimal. 


0:48:41 – Mike Malatesta

You might as well just you know hit the disconnect call. We got this experiment on this one, guys. 


0:48:49 – Casey Cheshire

I lost my internet. 


0:48:51 – Mike Malatesta

Yeah, I’ll give back to you when we can reschedule. 


0:48:55 – Casey Cheshire

So we got to stay engaged. But then I think it is that it’s like a hierarchy of needs. Right, we need to be engaged, we’re engaged, but then it’s doing those things, thinking about, you know, when I was sharing with Dave about time to value of your pod and other things you can do to maybe display the conversation in a certain way that that helps the people out that are listening, doing certain things that you may may not want to do. 


That can help the listener figure out what you’re talking. I don’t know, it’s just it’s like we do need to consider who’s listening at some point in the process. 


0:49:30 – Mike Malatesta

Yeah, Well, of course, I just kept so. Considering who’s listening is a different thing than who are you. You know, who do you need to satisfy first Totally? I’m always considering who’s listening. I learned this technique from a guy named David Senra who does a podcast called Founders oh cool, which is, which is a really good podcast, but it’s solo podcast and he talks about books that he read, biographies and autobiographies. He’s a guy super passionate, but one of the things that he does all the time and I do this now is he addresses his audience as you. So he’ll say, and you and me know that. You know from which whoever’s book that you know history doesn’t repeat itself. Human nature does, for example. That’s something he says all the time. So he’s always saying you or you and me, to try to keep, you know, the audience connected with him. Right, and I’ve stolen that and I use that now because I think it’s very powerful and very few people do it. 


0:50:46 – Casey Cheshire

I love that, I love that tip, the idea of dressing as you, and I haven’t heard a pro of that. But I have heard the negative, which is when you, when you talk about the people listening, you can oh, oh, my listeners, or yeah, my, my, my audience in ways that make people feel gross to be listening, right Like you, can sort of degrade your audience and lump them into a crowd. Oh, you, you, you people listening, you know, but it’s like no, you, I’m talking directly to you and just the two ears listening to this right now. That’s powerful, yeah. 


0:51:27 – Mike Malatesta

And I I I’m glad you brought that up, because this is totally different what he does. 


0:51:33 – Casey Cheshire

He’s not like. 


0:51:34 – Mike Malatesta

He’s not like those people who go you just heard a bomb drop here. Folks. You got to remember that you know, or whatever they. You know they sound like a radio DJ. His is just like. He just connects with you, you and me. He’s like you and me both and he’s not, you know, telling you what you should. He’s just like hey Casey, remember you knew and me were, whatever. That’s what he’s doing and I think it’s a really powerful, subtle way to connect with people that they don’t feel gross at all. 


0:52:02 – Casey Cheshire

They’re like oh yeah, we were, we were reading this book together or talking about, you know, henry Ford together, and yeah, it’s a cool technique, man, because you know I’ve listened to enough Joe Brogan episodes that I feel like I know the guy pretty well. I don’t know the guy at all, right, but I feel like I’ve listened to him so many times that you know, I know you and you don’t know me. But it’d be even worse that effect would be even worse or greater in this case If he was doing that on the show, like if he was talking to me personally by saying you know, like you’re describing men. That sounds like a recipe for a really cool you know, creating a relationship with your listeners, not just, you know, like a casual commercial one. 


0:52:47 – Mike Malatesta

Yeah, I think it’s something worth trying for people that are listening. I think it’s something worth trying to see how it feels for you. 


0:52:54 – Casey Cheshire

Well, you know what? You just dropped a bomb there. That’s what you did just now. 


0:53:00 – Mike Malatesta

Were you folks listening to that? Yeah, you got to write that. 


0:53:03 – Casey Cheshire

Yeah. Well, my audience was listening to that, and well, you know, I have one final question for you. Okay, is there anything I haven’t asked? 


0:53:16 – Mike Malatesta

Yeah, is there anything you haven’t asked what? 


0:53:24 – Casey Cheshire

Anything. I haven’t asked you. Is there anything? 


0:53:26 – Mike Malatesta

What? Yeah, you haven’t asked me what’s the one big takeaway that I’ve had from listening to your podcast, and I’ve listened to maybe five episodes so far. Oh cool, I’m going to tell you one of the biggest takeaways that I have had, and it was with your most recent podcast guest, the one that dropped. I don’t remember his name and I didn’t really. 


0:53:47 – Casey Cheshire

Was it this one about the podcasting, or was it the marketing one? 


0:53:51 – Mike Malatesta

It was about podcasting and I was listening to it and I was walking and I was kind of not completely engaged with his story. But at the end he said something. He started talking about some tools that he uses and he brought up this tool called Opus AI that essentially you download your video and it creates clips for you for social media. And I mean it creates you know, I Tried it right away yeah, and it creates wonderful YouTube shorts or social media posts with the transcription. It’s smart enough to know how to put it together most of the time. 


And I walked away from your episode like one of my major. So I have a producer. She takes my show and she edits it and she makes edits, the video, edits the audio, yeah, makes me one social media clip and and you know I pay X amount a month for that right. And I’m like, well, how do I get more social media clips? That’s what I want. I want more, more, more, more. Well, it costs more, more, more, yeah. So I was like, well, I don’t want to pay more. 


So then I’m listening to you and this guy on your podcast, you and here talking about tools, and he mentions this tool, but say I am right away. I’m like that’s what I’ve been looking for, boom. And Not only is it free if you just want to sort of mess around with it, but the pro version is 220 or 288 dollars a year, so every single. So what can I do to honor my guests we were talking about that before not just one social media clip that I’ll send you. I’m gonna send you and post one every day about our episode for a week. You know, um hello man. 


That was so. Thank you for having that gentleman on and asking him that question, which you could have not asked him. And and I and I think anyone who is listening and anyone who’s listening to this that is a podcaster or does anything on social media with video, and one of your challenges is how do I take this video that I have and actually make it digestible for shorts or social media clips? And then you combine that with chat, gpt, the pro version of that to make your Posts for you and incorporate the video and all of a sudden you’ve gone from something that was very expensive and out of your hands If you weren’t technical technical to something that any podcaster Can do. So tremendous value. There you go, boom. 


0:56:37 – Casey Cheshire

There it is, shout out to Nolan, by the way, that was, that was the episode we’re listening to you were listening to Nolan. 


0:56:44 – Mike Malatesta

Thank you, no, mccoy good dude. Man. 


0:56:48 – Casey Cheshire

Mike, what do you think? We just blasted through a time warp. 


0:56:51 – Mike Malatesta

Here we an hour later plus we made it, made it, we made it. Man, you’re good, good, you’re a good guide, thank, you. 


0:56:59 – Casey Cheshire

I appreciate it, man. Where can people reach out? They want to connect? You know some social apps or some Websites and URLs, and also throughout the name of the show too, so we can link to that. 


0:57:10 – Mike Malatesta

Yeah, so the show is. How did happen, and my name is Mike Malatesta m a l a T e s t a. Mike Malatesta comm. You can get everything about me there, so it’s centralized one spot. Connect with me, access the podcast there. Information about my book. Is there information about the dream exit that we talked about at the beginning, which is a program that I have to help entrepreneurs with revenue between five and a hundred million prepare for the dream exit that they deserve but often don’t get? So, yeah, everything’s there, mike Malatesta comm love it, love. 


0:57:53 – Casey Cheshire

We’re gonna have to hang out and Swap copies of our books so we can read, read each other’s books. That that is gonna go in my goodreads list, sir. Okay, great, it’s great, haven’t you here, mike? Thank you so much for coming on here Schooling me on things, having a good conversation about things, talking about intention, about how did it happen, why does it matter all these things the scripting, the control of the narrative man I just had such a great time. I appreciate you. 


0:58:20 – Mike Malatesta

Yeah, thank you so much for having me on. It’s been great. 


0:58:22 – Casey Cheshire

All right and everyone listening. If you learn something, I freaking know you did, cuz I literally have two pages of notes over here front and back then share it with someone else and be a thought leader to one person, nine people, three thousand people, whatever with that, mike. Thanks again, dude, and yeah, exciting stuff. I can’t wait to check out your next episode. 


0:58:40 – Mike Malatesta

Hey everybody, thanks for listening to the show and before you go, I just have three requests for you. One if you like what I’m doing, please consider subscribing or following the podcast on whatever podcast platform you prefer. If you’re really into it, leave me a review, write something nice about me, give me five stars or whatever you feel is most appropriate. Number two I’ve got a book. It’s called owner shift how getting selfish got me unstuck. It’s an Amazon bestseller and I’d love for you to read it or Listen to it on audible or wherever else Barnes and Noble, amazon you can get it everywhere if you’re looking for inspiration that will help you unlock your greatness and potential. Order or download it today so that you can have your very own copy and if you get it, please let me know what you think. 


Number three my newsletter. I do a newsletter every Thursday and I talk about things that are interesting to me and or I Give more information about the podcast and podcast guests that I’ve had and the experiences that I’ve had with them. You can sign up for the podcast today at my website, which is my name, mike Malatesta calm. You do that right now. Put in your email address and you’ll get the very next issue. The newsletter is short, thoughtful and designed to inspire, activate and maximize the greatness in you. 

Alexi Cortopassi

Alexi Cortopassi

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