Keep The Curiosity Coming – Mike Malatesta – Creating The Greatest Show – Episode # 052

by | Sep 12, 2023 | Creating The Greatest Show, Interviewing Authors, Podcast Framework, Podcast Guest Experience

This special guest is a serial entrepreneur and seasoned podcaster who has been featured in Forbes, Inc., Entrepreneur, and many more. Mike Malatesta is the creator and Host of How’d It Happen, Author of Owner Shift, and Dream Exit Expert. Mike joins Host Casey Cheshire for a takeaway-packed discussion on the importance of satisfying your own curiosity through your podcast, common guest introduction mistakes to avoid, and if you have an obligation to read every guest’s book.

Watch Mike Malatesta on Creating The Greatest Show!


  • If you’re interviewing a guest who makes frequent podcast appearances, they likely have a prepared narrative that they tell on every show. It’s up to you as the host to develop questions that get them to open up and share what lies beneath their pod facade.
  • When you’ve sparked the guest’s curiosity about themselves, guests will get more comfortable venturing beyond their tired talk track, to the point where they stop thinking about the podcast because they’re focused on the great conversation you’re having.
  • New podcasters may find it frightening to start an interview without a long list of prepared questions, however as they gain experience, many find that they only need a jumping-off point and can successfully navigate the conversation from there.
  • Whether or not you hold prep calls with your guests prior to recording with them, it’s still important to have a process for getting your guests the right information they need to crush their interview ahead of time. 
  • If you decide not to utilize a prep call with your guests, you still need to start building rapport with your guests. For example, Mike uses the first 20 minutes of the remote podcast recording call to start getting to know his guests and ensure their comfort.
  • Avoid sending subtle signals to your guests that you don’t care about them. Two common ways this can happen are by asking the guest to introduce themselves or by reading the guest’s bio verbatim. Show you care by putting some effort in and making their introduction a unique experience for them.
  • As a host, you need to make sure you’ll actually be interested in the guests you invite and the questions you ask. If you’re bored by your guests or the topic you’re discussing with them, the quality of the episode will drop drastically. If you don’t care about the guest or the topic, why should your audience care about the guest, the topic, or your podcast?

READ MORE: What Question To Ask First On Your Podcast

Quote of the Show

“I’m trying to get my guests to be curious about themselves.”

– Mike Malatesta

Connect with Mike

Clips from the Episode

Ways to Tune In

Episode Transcript


Casey Cheshire: what a cool convo we’re going to have. We’re going to be talking podcasting, going to be talking about all sorts of things here. I’m excited. I dunno what’s going on. I’ve got notebooks, I’ve got pens, I’ve got three ice coffees 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, [00:01:00] helping fellow entrepreneurs exit in that dreamlike 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. And what is his show, because that’s what we’re here to talk about, the show. He’s the creator and host of How Did It Happen, which now has over 440 episodes. As of a few days, who knows? That number’s probably doubled by now.

Author of Ownership and dream Exit expert. Mike. Mal Testa. Welcome to show, sir.

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

Casey Cheshire: I did. I like

Mike Malatesta: started. Now that’s enthusiasm.

Casey Cheshire: It’s what? What was that? That just happened? That was me running into

Mike Malatesta: all the caffeine from those iced

Casey Cheshire: yeah, exactly right. Crazy man. So I’m glad you’re here. We get to geek out about this thing. We both love for the next bit of time here. So I want to start the show. The way we start every show by [00:02:00] asking you this question Mike, pull back the curtain for us on your show and share your most important strategy for a great interview podcast.

Mike Malatesta: Yeah, sure. So like you said, my show’s called How It Happened, and I do two things on that show. once a week I have conversations with really successful people from all walks of life, and 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.

And two is get to the point of why it matters to you if you’re listening. And 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 and on Free Thinking Friday, it’s just me and I do a solo episode That’s you, 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, that I think was cool and that I think the people listening [00:03:00] to me will also. I think is cool as well. So that’s the show. But I’m going to focus on the conversations I have with successful people for the answer to this question. And 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 o other professionals, they show up wanting to control the narrative around their conversation. And they’re pretty good at it. And 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. So it’s really an organic sort of, oh, and then, when the head [00:04:00] goes like til tilts a little bit like that, then I feel like we’ve broken some new ground and I really like to get to that new ground where the guest is curious about themselves.

Casey Cheshire: Wow. So it, that’s like an a, like the aha moment king at that point. You’re creating these little these moments, but then it can’t be easy. I it’s almost like the folks that are in control to your point, and are good at it. It’s almost like it requires what vulnerability.

It requires a lot of different things that people probably don’t come prepared to bear their souls on your show, or do they?

Mike Malatesta: Yeah. So I think there are some that, some people are in the business of bearing their souls, so it’s, so

some people, yeah 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 W when you get them to be curious about themselves, you [00:05:00] 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 squad cast or a Zoom or on a podcast at all. And I’m not suggesting I get there with everybody ’cause I don’t.

But man, when you do. Yeah, that’s where the like some people would call that’s the real gold. And then, that’s where you have a great podcast and the person when you’re done is like, man, that I just never thought I would be talking about, whatever it was today.

And but they’re happy they did.

Casey Cheshire: What is it about those unscripted moments that are so magical? Why? Why do you pursue the, it is a bit, it’s not just rhetorical, but like what is about those moments that. Is magic to listen to and then also magic to be a host of[00:06:00]

Mike Malatesta: To me, they reflect the reality of life as a human being. 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, right? So what normally happens is, I run into you, Casey hey, I’m Mike.

What do you do? Where you live? Where you from? Where’d you grow up? And they 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, it wouldn’t make sense to logically. Follow a list of questions , getting answers, you’re getting feedback, you’re getting direction from the person you’re talking to.

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 you, to hear that answer they give. And, great. Thanks Mike. Your next question is this, you [00:07:00] just, in, you, 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 is probably dumb, 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 roll the dice, talk to me about that. Have you always been like this, or did you evolve into it?

Mike Malatesta: Yeah, I evolved into it, I think and I put myself back in my, 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 the, I’m going to hit a brick wall with this person at 15 minutes in and I am on an hour show and I’m not going to know where to go.

So there’s, there was always that fear. So I would have a list of [00:08:00] prepared questions when I first started, not. With the intent of asking all of those questions, but with the it was like preventative measure of if we get stuck and we have no, I got nothing, I’m going to go and I’m going to ask him one of these questions to try to get it restarted.

And then I discovered over time that I never asked any of those questions. Ne I never asked any of those questions. Then I began to two things. So I began to abandon that. But also, I also learned one thing that if I’m, 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 [00:09:00] have notes in front of me that I’ve made on 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. And connect the two of them in what hopefully seems like an organic, natural way. So that’s that’s been my evolution and I don’t write any questions out any longer.

Casey Cheshire: Do you have a couple go-tos? That you go to, or nothing completely unscripted. Have you gone completely.

Mike Malatesta: I’m, 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 [00:10:00] get asked a bunch, how do you want me to answer that?

Mike Malatesta: And I I. I always say the best answer is the one that you want to select to answer that. Now you could say what if the person goes off on some wild ride? That makes no sense. That’s a risk. But I found that in, 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 scripting the podcast. And then I’ve taken to this more recently, but at the end, and I think I’ve 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 th and I like doing he does that, and I liked that. It often brought up something that I hadn’t thought [00:11:00] about, which is, but his, value to leave with the listener. And and it’s a simple question. They, and they can say, Nope, 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 I didn’t connect that dot, or I totally missed that part, or whatever. And it’s makes a good ending, I think.

Casey Cheshire: And a lot, some guests will, I’ve been on shows where I had a point and it’s gosh, darn, I’m going to make that point. You almost like a politician, right? Where they’re like, they ask you one question, you’re like, cool, let me finish my point over here, and then I’ll get to your question.

So some guests will just do that. But I love the idea that some won’t, some will just go with you wherever you’re going 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

Mike Malatesta: Yeah, and it makes it makes it not like an interview. It makes it, to me, it like takes a little bit of the, hopefully the interview thing is gone by the end, but if it’s not, it’s like here’s an opportunity for you to,[00:12:00] help me out here with something that is important to you. And I’m not talking about promoting their website or their core 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 me and to everyone listening,

Casey Cheshire: Yeah. This is a good topic too, because if you, and you said you don’t do the prep, right? No prep calls,

Mike Malatesta: it’s rare. It’s rare.

Casey Cheshire: You just get on the show. Let’s go.

Mike Malatesta: Oh no. So our process is very detailed. So when, once we book, so we sense everyone an invitation. And in that invitation it describes exactly how this is going to go. The time, the type of equipment we would love you to have. How the, how I’m going to ask the start. It’s an unscripted podcast.

I’m going to start with how’d it happen for you? And so it’s very [00:13:00] detailed that way. But I don’t usually get on the phone with or zoom with people beforehand. I.

Casey Cheshire: Yeah. Okay. And 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, the thing that I have to. The challenge I have to deal with on a prep call is making sure you don’t just run away and say the whole show on the prep when we’re not recording.

Mike Malatesta: Yeah, that and that’s one of the, that’s one of the, and I think I, I think I. When I heard you with Dave Will, that was one of the things he said. ’cause you guys were debating Prep Call, not Prep call. And he was I think you both had good points because he was 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. And that made a lot of sense to me too. So I’m not I’m rethinking it but. I don’t know which way I’ll do it, but I But you’re, the prep call makes sense to me if if it’s got a tight agenda and you’re not [00:14:00] going to open up the whole story.

Casey Cheshire: Totally. And 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. An organized prep call can be great. So that it’s the second time I’m seeing you we’re chatting today, that kind of thing, as opposed to, 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. Did a show without a prep call recently. It was a, it was really interesting. It was a childhood hero. It was a marketer who had been decades championing ss e o and how to market. Rand Fishkin, really cool guy.

No prep, right? Which you tend to get with the more busy slash. Famous. 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 [00:15:00] have to deal with on my show, warming him up.

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. So we had to have that initial dialogue, which might be tied into that 20 minutes You mentioned that initial 20 minutes where you’re feeling each other out.

Casey Cheshire: tell me more about your 20 minutes.

What do you do in that 20 minutes to make? To make it to the 20? You can get to the hour.

Mike Malatesta: I wish I could tell you. I just try to get there,

Casey Cheshire: survival.

Mike Malatesta: what, yeah, what I’ve learned is that patience is really valuable. For instance, I would be nervous. When I started, I’d ask, I’d be like what if I asked the, how’d it happen question? And they give me a two word answer. What am I going to do with that?

Fortunately, that’s hasn’t happened. Maybe I’ve gotten one sentence from a couple of people, but I, so I used to be nervous about that [00:16:00] because I was thinking how do I move on from here? But now I’m just patient with it, so I know that whatever they say, Is going to lead to 3, 4, 5 questions. Of course, I don’t know what they are, but I know it’s going to lead to that Casey, and then by that time we’re off and I don’t fear that 20 minute thing anymore.

So like that saying, you slow down to speed up. That’s what. That’s 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 going to be whatever they say, man, it’s going to be like, let’s follow that.

And so it just hasn’t been an issue for me for a long

Casey Cheshire: And it sounds like you’re also. Once you deal with something once as a host then it’s not as a sur much as a surprise the second time. So to [00:17:00] get that one sentence answer can be scary. Once you go through it, you’re like I dealt with it. I’m sure you asked some kind of follow up, but I do wonder about those short answers.

What’s your take? Why? Why do people sometimes give short answers?

Mike Malatesta: I think there’s a. There’s a humility angle to it. People who aren’t naturally comfortable talking about themselves maybe they haven’t been on very many podcasts and they’re not naturally inclined to talk about themselves. They’re used to going through life in a humble way and a humble way is.

Say as little as I can about myself, but be polite. So I think that probably has something to do about it. And or I, 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’s because it’s a complete choice.

You [00:18:00] 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 questions because they’re part of the network. And if you don’t answer the questions, you get fined.

Casey Cheshire: How’d you catch that game? Winning touchdown.

Mike Malatesta: yeah. How did you feel when you threw

Casey Cheshire: Yeah, let me know when, yeah,

Mike Malatesta: What did you guys talk about in the locker room to get psyched up for the second quarter. Oh, okay. Yeah. Let me tell you everything I said. They all, yeah, it’s, yeah. Anyway, I’m surprised that I, and I know I’m going off on a

Casey Cheshire: Yeah. That’s what we

Mike Malatesta: I’m surprised that that those positions still exist and that anyone caress.

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

Casey Cheshire: and you’re like, what are you talking about? Stop asking them questions. Let them just celebrate and hold the [00:19:00] cup up. Hold the trophy, bask in the moment. It’s crazy. 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. They’re not, they’re either not excited about the question or they don’t know anything about the question, right? So like passion and expertise are not present. So it’s just I am nothing to really say here, but for question, like, how did it go? And or how did it happen? And these are things that a founder.

It should have. So I would imagine it’s pro probably more the humility side with a lot of people you’re talking to versus, because I sometimes you can ask people questions that are just duds. Have you had that, have you ever you recall

Mike Malatesta: of course

Casey Cheshire: the one I just asked

Mike Malatesta: like I, yeah. Speaking of recency I so I had, this hasn’t come out yet, but I had this guy on my [00:20:00] 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, 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, like this, and I. I asked him hey, I was like, you’re doing these Spartan races and you’re doing this other, these other types of thing.

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, your big questions, like stuff you wouldn’t think about? And he’s That’s usually happens in the shower.

And I was like, okay, that’s telling me that wasn’t that great of a [00:21:00] question. 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?

That wasn’t a great question. It may probably happen more times than I think.

Casey Cheshire: Yeah. Because, and that goes to that earlier idea of the scripting versus nons scripting. At least if you script it. Maybe it looked good on paper, maybe it fell flat during the conversation, but at least it sounded good when writing. But when making up a que like, we’re riffing. We’re going off in these, we’re exploring together.

Sometimes you have those things.

Mike Malatesta: Yeah. And, that, that’s, you just made me think I, if you have scripted questions, your natural tendency is, and you don’t have patience, your natural tendency is to be, is to get to that question, and you might, it might be the greatest question, you just ask it at [00:22:00] 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.

Casey Cheshire: right. And yeah you force it early. What, tell, 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? Talk to me about that. It.

Mike Malatesta: Yeah, I really don’t. I really don’t know what. Questions I’m going to ask Casey. Besides that first one, I said, I know I, I know there are topics or things that I want to weave in at some point when it’s right, but I 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.

Casey Cheshire: That’s, yeah, that totally makes sense. By the way, I would argue that was a good example of an [00:23:00] unclear, I wouldn’t call it a dead question, but I would say like an unclear question. And I’ve often found podcasters will figure it out and they’ll just make a great answer like yours was just now.

Whereas that untrained person who was just literally going to take you literally. And if I’m like, have you ever felt that they’d be like yes or no? It just if you them a boo in question, they’re 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.

Mike Malatesta: Again, like I mentioned, when you come onto 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

Mike Malatesta: Yeah.

Casey Cheshire: Especially if it’s you’re trying to have a conversation. It’s not c n n. We’re not debating, we’re not, surging each other. This is [00:24:00] just, it’s just two people having a convo about things they love. So you only, your only scripted question is your first one. And it’s interesting, my other show I used to ask a couple different mile.

I, even now I have a couple 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.

And they’re like, what’s your biggest failure, bro? And it’s I actually once had one person ask me on a podcast, she was so nice. But your first question was like, so who are you? What makes you? And so because it was early in the process, I gave her the, the polished answer, which is I’m a technical communicator and blah, blah, blah.

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. So it’s almost like when you can warm them up and it sounds like, maybe that’s something you’re doing just naturally [00:25:00] because it’s not scripted.

You’re just evolving the question.

Mike Malatesta: Yeah, that’s a, I definitely want to get to who you are but I’ll ne but I never ask it that way because when I. To me that question, for example 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 when we’re.

Just getting started and once you do, like I’ve had that asked of me and all kinds of questions, on these types of podcasts that I’ve been on that you met you referenced there. And I, as soon as to me, when I get asked something like that, I’m just like, okay. Lazy. Or when it’s oh, hey Mike, why don’t you introduce yourself to everybody?

Okay. Lazy. And there’s a lot of, and I. I’m not saying I’m right about that’s just how it feels to me as a guest or a listener. So I

Casey Cheshire: Can we talk about that

Mike Malatesta: I would,

Casey Cheshire: [00:26:00] I, ’cause 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’s, 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, if you can pull off the interview and make it look like maybe you don’t actually know who they are.

You almost a C N N. Yeah. No, I didn’t read your book. I’m just going to literally ask you four questions that anybody could have asked you. It just, it transmits the wrong sig.

Mike Malatesta: 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? We’d like to have these things and when I’m on shows, I get, I give them, the what, the bio, what they need, the bio, the, and and I’m not looking for someone to, like with my bio, I’m not, I don’t care if they read the bio, word for word.

In fact, I’d [00:27:00] rather they didn’t. What I’d rather they do is talk about who I am in a way that makes sense to them. And then I can fill in the rest. I’m on your show for an hour here or whatever. So I can fill in the rest, but I just don’t like that, like I said it, to me, it says lazy. And it just, to me, it’s not a great way to,

Casey Cheshire: Yeah.

Mike Malatesta: start.


Casey Cheshire: To be fair, if you’re listening to this, and that’s the method you do, I understand you may not know or not be aware of that, that you might be sending subtle signals, to your guest by doing that. So maybe 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 guest means to you. Far outstrips trying to ever read a bio of someone, right? We’re not here to read their biography, their 30 volume text.

Mike Malatesta: Yeah. Yeah. So I just find that it’s a subtle [00:28:00] 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 make it like my own. I try to make it my own. And oftentimes, It there’s a question to them in the bio in the reading of the bio, which I hardly anyone does that. But I think they like it.

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

Mike Malatesta: Yeah, so they might have I am a [00:29:00] certified, nutraceutical blah blah something, right? And I’m like I know. I don’t know what that is. So rather than just reading. What they wrote. Casey is a certified nutraceutical whatever, X-ray. 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 breakup in the bio that. In the reading of the bio that brings the guest in right away, but in a way where they’re helpful to me as opposed to me trying to be, know everything about them.

Or I’ll say and, or they’ll have some designation. I’ll be like, had to, it had to feel cool when you were profiled in Entrepreneur Magazine. And I’ll just say that it’s not like a question to them. I’ll just be like, eh, that had 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.

Casey Cheshire: That’s really cool. That’s a really cool tip. That’s like a power [00:30:00] tip there. The idea. Of building in it’s almost a rhetorical or just it’s and are you actually asking that question or are you just like mentioning oh, that was, that would be really cool. The fact

Mike Malatesta: De

​Yeah, it depends. Or like that same one. I might read that, they were featured as whatever in Entrepreneur Magazine. I’d be like, how’d that feel?

Casey Cheshire: Yeah.

Mike Malatesta: So sometimes it’s just a comment on it and sometimes it’s a just a small little question that I’ll, I just think it, I don’t know, feels like it works to me.

Casey Cheshire: Yeah, so it’s something about it, it’s like a, it’s like a little micro signal that says, As I, I’m interested in you and I know just something more about you than meets the eye. E doesn’t necessarily have to be reading the book. A friend of mine, Ethan, he will read all of your books and he’ll outline them and he’ll bring up quotes and everything and he’s the master of preparation.

But something as little as. As [00:31:00] remembering the fact that you’re in Wisconsin, which is where my sister-in-law is and I went to a concert there, just something that kind of gets brought up. But even better if it’s about their accomplishment.

Mike Malatesta: 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 because I want the that’s why I reached out to them, really. And I know what they’re trying to accomplish.

On the other hand, it just because someone has written a book, I don’t, 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 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 you, if they wrote a book and you haven’t read it, then I think you should [00:32:00] say, I haven’t read it. And not pretend to have. Read it or pretend we’re going to dive deep into the book. So tell me what chapter one’s 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’s you may have heard of. He’s got. Podcast called James Outer Show. And he reads a lot of books for 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 you’ll know more than most people who are going to talk to them about that book will ever 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 [00:33:00] something. but then I wonder too like Tim Ferriss will say, I don’t read any, 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 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 this, 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. ’cause I got my own stuff to do. But you’re still going to have a great conversation with me.

Casey Cheshire: That’s interesting. I

Mike Malatesta: do you do?

Casey Cheshire: 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 I’ll know [00:34:00] everything. And why would I ask you? Because I already know everything that you. 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, too much. ’cause 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.

But like I’m generally asking ’cause 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

Mike Malatesta: Yeah. Except that, except maybe that the people who are listening to your podcast haven’t read the book. So while the answer may not be surprising to you, it may be surprising to them. So I think there’s. Like I said, I go I’ve I read a bunch of them, but I don’t read all of them.

I do feel like I’m better prepared when I’ve read the [00:35:00] book

Casey Cheshire: Oh, a hundred percent. Yeah.

Mike Malatesta: And not just about the book itself, but about them. There’s a lot more usually in the book about them than their bio suggests,

Casey Cheshire: spent some more time with them. My excuse is that I want to be inspired to read the book after this conversation. It could be lazy. I don’t know. Something I’m, something I’ve been toying with. Yeah.

Mike Malatesta: I don’t think it’s lazy. I don’t, that’s that, I don’t think it’s lazy. You’re asking somebody that’s a lot of work, 4, 5, 6 hours to read a book.

Casey Cheshire: sure. Especially if you, what if you don’t like it though? What if you

Mike Malatesta: not nothing.

Casey Cheshire: Have you ever had that? Have you,

Mike Malatesta: Sure, of course. I shouldn’t say don’t. There’ve been there have definitely been some where I haven’t enjoyed them as much as others, let’s put it that way.

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 I want to read it. That’s not what I’m. Looking for generally, [00:36:00] 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, I need to dig into that.

Casey Cheshire: It’s definitely a different dynamic if you’re requesting of them to be

Mike Malatesta: yes,

Casey Cheshire: you know them just pitching you and you’re like, cool, let’s give this a whirl. There’s definitely a difference there,

Mike Malatesta: I, yes, for sure.

Casey Cheshire: and I almo it almost works better when you ask them to be on, right? Because they’re, you’re invested interest, you’re excited. At least like when Rand came on my show, he doesn’t know who I am, but but I. 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. At least half of it. I’m a fan and he eventually becomes a fan. It’s a cool dynamic to it.

Mike Malatesta: So how did you get him?

Casey Cheshire: How did I just reached out? [00:37:00] I said,

Mike Malatesta: He did okay,

Casey Cheshire: It wa wasn’t any real magic to it. Maybe, maybe he’s famous in a select marketing community, but yeah, just really, but a really cool guy.

Mike Malatesta: Yeah. He is

Casey Cheshire: Yeah, just really cool guy reached out and also he is doing a new thing now, so he’s got, he’s got a new SAS app. He is, he’s doing things and so of course he could, he could use the attention and the promotion as well. So there’s a benefit to him to be on. But yeah,

Mike Malatesta: Okay. Yeah, his name’s really familiar to me. He just recently had a company that he sold, I think

Casey Cheshire: Yeah. He founded the SS e o Moz company, or at least with. His, with his family, he created the Moz, m

o z. It’s pretty cool. But now he’s doing the the next phase. So it was just a cool convo and we got to a lot of stuff. But now that we’re geeking out on, on, on like how much we love it, I’m just curious, is there one particular aspect you love the most about being a home?[00:38:00]

Mike Malatesta: I love to have my own curiosity satisfied, so I want people to get curious about themselves when we’re talking, but I. I just get a lot of energy out of my own curiosity being peaked and satisfied. 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 I know I, my curiosity wasn’t satisfied at all with that person.

That rarely happens. So I think as for me as a host, that’s like number one. I, I always I’m always trying to do work that I think is important, and I’m always trying to do it as best as I can on that day. And I, geez, I always hope that someone else will like it and get it. I think that’s the thing that if there’s anything that.

If there’s anything that I [00:39:00] am, I feel like I’ve still massively in search of is how do I get more people to give my show a chance.

Casey Cheshire: Yeah. Yeah.

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

Casey Cheshire: And this kind of brings up that challenge of do in your intentions, who’s more important, your own curiosity or the listener’s curiosity?

Mike Malatesta: Yeah. So what do you think the answer to that is?

Casey Cheshire: I was, I wanted to know your answer before I, I. I,

Mike Malatesta: Okay, [00:40:00] so my answer’s clear. If it’s, if it. 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.

Casey Cheshire: But isn’t it tempting then to make the listener. Are the priority right now, my answer is more like yours because I couldn’t sit through this thing like one for instance, other than Rand, who is a reformed ss e o specialist in the marketing community. I can’t stand to talk to anyone about that specialty on my marketing podcast. Just, 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 was funny. I was like 20, but other than a hero of mine, I don’t really want to talk to [00:41:00] any, and we didn’t talk SEO O either. So it was like, I just don’t want to do, I just can’t do it. So there’s certain things I just don’t, it’s just, that’s anti curiosity for me.

But you’re, I’ve always felt that if I’m interested, then wouldn’t everyone else be too, which may or may not be true,

Mike Malatesta: you think about any type of production, right? It’s whether it’s a movie or television or a standup show or whatever. You’re always interested in whether the audience is going to accept what you’re doing,

Casey Cheshire: Yeah.

Mike Malatesta: But you’re always best when you’ve accepted what you’re doing. 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.

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 [00:42:00] get better. It is a continuing, continuous improvement process, but if you’re not sold on the core of what you’re doing you’ll be like, probably like most to 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 difference, right? There’s difference between commitment and trying. I feel like I’m committed to, yeah.

Casey Cheshire: it creates such a low energy when you’re not interested. So I do feel like it’s kinda like a table stakes, that if you’re not interested, then who else is going to be, I confession to make in one of my let’s see. I’m chasing your number. I think something like 300 episodes on the marketing pod and a bunch of this one.

In one of those episodes I did check out mentally and check my email. Know, and and my slack and everything else in under the sun because the guy was just so boring and I hated it. And 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 [00:43:00] interested.

And instead of trying to take like an active role in interrupting him and maybe asking something different or some other question, I just let it ride. Let him do his monologue and then I’m just going to. Not be there, and it just, it’s just not good. As people could imagine. It does not make the episode doesn’t get better when you do that.

Mike Malatesta: Yeah. It’s, what do they say that suboptimal that is

Casey Cheshire: This is very,

Mike Malatesta: than ideal. Yeah.

Casey Cheshire: It’s,

Mike Malatesta: You might as well just, hit the disconnect call button and I,

Casey Cheshire: we got

Mike Malatesta: it’s a good experiment on this one,

Casey Cheshire: I lost my internet.

Mike Malatesta: we’re going to, yeah, I’ll give back to you when we can reschedule.

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, when I was chatting 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, that [00:44:00] helps the people out that are listening, doing certain things that you may not want to do that.

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

Mike Malatesta: Yeah of course. I just ca so considering who’s listening is a different thing than who are who do you need to satisfy first? I’m always considering who’s listening. I. I learned this technique from a guy named David sra who does a podcast called Founders, which is a really good podcast, but it’s solo podcast.

And he talks about books that he read biographies and autobiographies. Really guy’s 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. From which whoever’s book that, history doesn’t repeat [00:45:00] 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, the audience connected with him. And I’ve stolen that and I use that now because I think it’s very powerful and very few people do it.

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 talk about the people listening, you can oh, my listeners, or

Mike Malatesta: Yeah.

Casey Cheshire: My, my audience in ways that make people feel gross to be listening.

Like you can degrade your audience and lump them into a sort of crowd. Oh you people listening, but it’s no, you, I’m talking directly to you and just the two ears listening to this right now. That’s powerful.

Mike Malatesta: Yeah. And I’m glad you brought that up because this is a totally different what he does. He’s not like you sh he’s not like those people who go, you just [00:46:00] heard a bomb drop here, folks, you got to remember that. Or whatever they, they sound like a radio dj. His is just he just connects with you and me.

He’s you and me both know, he’s not telling you, he’s not, telling you what you should. He’s just Hey, Casey, remember you and me were whatever. That’s what he is doing. And I think it’s a really powerful, subtle way to connect with people that they don’t feel gross at all. They’re like, oh yeah, we were reading this book together.

Or talking about, Henry Ford together and,

Casey Cheshire: it’s a cool technique, man. Because, I’ve listened to enough Joe Rogan 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, 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.

If he was talking to me personally by saying, eh, Know, like you’re describing, man, that sounds like recipe for a really cool, creating a relationship with your listeners, not just, ca like a casual commercial [00:47:00] one.

Mike Malatesta: Yeah, I think it’s something worth trying for people that are listening. I think it’s something worth trying. See how it feels for you.

Casey Cheshire: You know what? You just dropped a bomb there. That’s what you did just now.

Mike Malatesta: Were you folks listening to that? You got to write that. Yeah.

Casey Cheshire: My, my audience was listening to that and I have one final question for you.

Mike Malatesta: Okay.

Casey Cheshire: Is there anything I haven’t asked?

Mike Malatesta: Oh boy. Yeah. Is there anything you haven’t asked? What

Casey Cheshire: Anything I haven’t asked, anything I haven’t asked you? Is there anything.

Mike Malatesta: 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, and 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, and I don’t remember his name, and I didn’t really,

Casey Cheshire: Was it this one the about the podcasting or was it the marketing one?[00:48:00]

Mike Malatesta: it was about podcasting.

And I was listening to it and, I was walking and I was not completely engaged with his story,

Casey Cheshire: Yeah.

Mike Malatesta: 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 it creates, I tried it right away 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, makes me one social media clip.

And I pay X amount a month for that, [00:49:00] right? And I’m like how do I get more social media clips? That’s what I want. I want more. It costs more. So I was like, well, I don’t want to pay more more. So then I’m listening to you and this guy on your podcast and you and here are talking about tools and he mentions this tool open.

Say I, right away I am like that’s what I’ve been looking for. 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 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 going to send you and post one every day about our episode for a week. And 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 [00:50:00] 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 G P T. 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 to something that any podcaster can do. So tremendous value.

There you go.

Casey Cheshire: Boom. There it is. Shout out to Nolan, by the way, that was the episode

Mike Malatesta: Nolan. Okay.

Casey Cheshire: or you were listening to

Mike Malatesta: Nolan, thank you for that.

Casey Cheshire: Good dude. Man. Mike, what do you think? We just blasted through a time warp here. We, an hour later plus

Mike Malatesta: we made it.

Casey Cheshire: made it.

Mike Malatesta: We made it. Man, you’re a good guy. You’re a good guide. Thank you.

Casey Cheshire: I appreciate it, man. Where can people reach out? They want to connect, some social apps or some [00:51:00] websites, some URLs, and also throw out the name of the show too. We can link to that.

Mike Malatesta: Yeah. So the show is, how’d it happen? And my name is Mike Malat Testa, M a l A t E ss t a, Mike malat 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 mal

Casey Cheshire: it. Love it. We’re going to have to hang out and swap copies of our books so we can read each other’s books. That is going to go on. My Good Reads list, sir. It, it’s great having you here, Mike. Thank you so much for coming on here, schooling me on things, having a good conversation about things, [00:52:00] talking about.

Tension 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.

Mike Malatesta: Yeah. Thank you so much for having me on. It’s been great.

Casey Cheshire: All right, and everyone listening, if you learn something and I freaking know you did, ’cause 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, 3000 people, whatever. And with that, Mike, thanks again dude. And yeah, exciting stuff.

I can’t wait to check out your. Next episode.

All right, cool guys, that was it. Another crazy cool episode of creating the Greatest Show. We will see you all next time.


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