Prioritizing Guests Over Questions – Jeff Pedowitz – Creating The Greatest Show – Episode # 053

by | Sep 26, 2023 | Creating The Greatest Show, Hosting a Podcast, Podcast Guest Experience

Today, we have a distinguished guest with us, Jeff Pedowitz, who is not only a serial entrepreneur but also a prominent figure in the fields of marketing and sales. He holds the prestigious title of a Forbes best-selling author for his book “F The Funnel,” and he has recently released his latest work, “AI Revenue Architect.” In addition to his writing achievements, Jeff is a seasoned podcaster, serving as the Host of the CMO Insights Podcast, which boasts over 170 episodes and is currently in its eighth season. Jeff joins Casey Cheshire for an engaging discussion about the significance of conducting genuine conversations, prioritizing the comfort of your guest to showcase them in the most favorable way, and mastering the art of riffing while recording a podcast.

Watch Jeff Pedowitz on Creating The Greatest Show!


  • Focus on natural, engaging conversations in podcasting, prioritizing the person over a structured list of questions, and letting the dialogue flow organically to create captivating audio content.
  • It is important to prioritize the guests in a podcast, relieving oneself from self-imposed pressure, and allowing authentic interactions to take the spotlight.
  • Furthermore, prioritize the comfort and natural rapport with the person being interviewed in a podcast, as this leads to a better podcast experience for both the guest and the audience.
  • A podcast should be a natural conversation, and while audience size matters, the primary focus should be on delivering good interviews and content. Mistakes are part of the journey, but quality content keeps the show going strong.
  • The goal of podcasting is to bring out the natural and authentic personality of each guest, allowing them to be themselves rather than forcing a scripted or artificial persona, even while maintaining a degree of professionalism.
  • The responsibility for a good podcast interview lies with the interviewer, not the guest. If the interview goes well, it’s a result of effective hosting, and if it doesn’t, the blame should be on the interviewer, not the guest.
  • Successfully riffing in a podcast interview is about being fully engaged in the conversation and actively listening to the guest, rather than being preoccupied with what to ask next. It’s essential to keep the focus on the guest and not make it about the interviewer.
  • During podcast interviews, unexpected moments or anecdotes from guests can suddenly make the conversation come alive and become interesting, prompting the interviewer to dig deeper and make the rest of the interview strong and engaging.

Quote of the Show

“I started by giving myself permission to not have to be perfect and to just be myself.”

– Jeff Pedowitz

Clips from the Episode


Ways to Tune In

Episode Transcript


Casey Cheshire: All right. Here we go. Here we go. I’m excited and I’ve had some cold brew. So this is going to be a fun show. I can’t wait to introduce you to our guest today. He is someone I’ve followed for a long time in the marketing world, and it’s such a pleasure to sit down with him today on a Friday. And if it’s not a Friday, when you’re listening, I hope this is just one moment for you or maybe it’s just a little piece of a Friday for you.

This is going to be such a great conversation. Who’s your guest, Casey? [00:01:00] Stop talking. Who is he? Serial entrepreneur, marketing and sales thought leader and actual leader. He’s an author two books. One bestselling on Forbes is the book F the Funnel. And if that gives you a sense of where we’re going, I don’t know what else does, but his new book is coming out, probably out soon.

If not already out when this episode airs, AI Revenue Architect. Check that one out. We’ll talk a bit more about that later. And he is a seasoned podcaster, host of CMO Insights, over 170 plus episodes. He’s into season eight plus. He’s been doing this a while. I can’t wait to roll up the sleeves and chat podcasting with him.

President and CEO of the Pedowitz Group, Jeff Pedowitz. Welcome, sir.

Jeff Pedowitz: Thank you, Casey. So exciting to be on your program, man. And I know we’ve been jamming on so many other things over the years, but it’s great to finally get to be a guest on your program.

Casey Cheshire: Absolutely, man. We were joking just a moment ago how this isn’t a marketing podcast too. We got two marketing nerds in the room, but we get to talk about something [00:02:00] else we’re passionate about, which is podcasting. So I love for you, man, just pull back the curtain for me on your show and share your most important strategy for a great interview podcast.

Jeff Pedowitz: Yeah, the irony is when I first started podcasting I ended up being someone who I’m not, because I was so stressed about I had to be over prepared, I had to have a highly structured set of questions, I had to know my guests meticulously. I was thinking constantly about my body language, my voice, whether or not I’m looking at the camera, it just felt uncomfortable.

So I got through my first couple of seasons okay, and there’s just some good guests and the interviews were okay. But as I started to really reflect on it, It was just very dry and very stilted. And while I do prepare a lot, that’s not actually how I normally talk and engage with people. I have conversations.

I ask questions. I really are more focused on what they’re saying and then I react to what they’re saying. So starting in season three, [00:03:00] I became less concerned about how many questions I could ask within the 20 minute or 30 minute time period. And I focused more on the person. And I really came in with just one to two things that I really wanted to know about them.

And I had maybe two questions. That’s it. And then from there. I just really based every single podcast around the individual. Now in the back of my head, maybe based upon the time period, cause we’ve been doing this now for a good seven years. So as things come up in the market, whether it was the pandemic or the great resignation or the war in town, things like that, sure, that might creep its way into the conversation.

But I really try to think about the person and make the conversations natural. So for me, then I think the key to having a good podcast. is to really make it about the conversation, particularly since most podcasts don’t have the video. They’re really about the audio, and so you start thinking about what makes good radio.

It’s really that entertainment dynamic, that the conversation, the words, the description has got to come alive because you can’t see it.[00:04:00] The conversation has to be natural and free flowing and has to be interesting. But rather than put all that pressure on myself as the interviewer, trying to come up with the perfect question to ask, I just tried to make it more natural and approach it more about how I would normally approach a sales situation or really just anybody that I would meet at a cocktail party.

Casey Cheshire: I hear you on the pressure. Man, I used to get so stressed. I would actually jump on a trampoline before a podcast just to get all psyched up. It’s going to be okay. And, but yeah, that pressure to make it natural and interesting, man. Don’t we all that sort of imposter syndrome rears its ugly head.

It’s man, how am I going to entertain all these people? How do you release that pressure valve?

Jeff Pedowitz: I guess I started by giving myself permission. To not have to be perfect and to just be myself. If you, people that really know me, it’s really not about me. It’s about the team. It’s about winning and doing good work for my clients. So what I really want people to get from my [00:05:00] podcast is I want them to listen to the guests.

It’s not about me. It’s about them. So to me, it’s just, what can I do to make this person shine? And that takes a lot of pressure off itself because then I’m not worrying about myself. I’m not trying to worry am I sitting up straight? do I have the right smile? Is my shirt pressed?

Like I just, that’s to me what creates the pressure, it’s a, but I generally, because I do love being around people. I love going to trade shows. I love going on sales calls. I love talking to people all day long and get energized by them. For me, that’s the perfect pressure release because I could talk to people all day long, so, don’t stick me in a research lab, without people with no windows, that would be the death of me, that’s not how I am, I got to be with people.

Casey Cheshire: I hear you on the people thing, man. Just, it makes me come alive too. And I love connecting, right? And I thought of like for the new company, the RY is just human connection. I just, I love this aspect of podcasting. In, in the fact you give yourself [00:06:00] permission to not be perfect. It’s just about connecting who, you know, who cares what, who cares what the audience thinks or how it just, if you’re not perfect, what happens, right?

I guess that’s the question.

Jeff Pedowitz: I, I’m not thinking really so much about the audience, I’m thinking about the person I’m interviewing.

Casey Cheshire: Yeah,

Jeff Pedowitz: Are they comfortable? Is it a natural conversation? Look, many of my guests I’ve known for years. It’s easy, we have common rapport, we’ve gone to bars together, we’ve been on done things together, so it’s easy to have a commonality, but then there’s plenty of guests that the very first time I’m meeting them is when they’re on a program, and so I only really have just a couple minutes before the podcast starts to build some familiarity to create some warmth.

Without it making it artificial. So again my goal is really zeroing in on that person. And how can I make this person comfortable so they can be the best version of themselves? Because if they, if I can do that for them, then the audience will get a good podcast.

Casey Cheshire: right. Because [00:07:00] they’re able to be their best self. It’s interesting that you mentioned that at the very beginning, the idea of just not being yourself because you had all these things you’re thinking about. And as you mentioned, I’m thinking the guest probably has that same problem and they’re taking your lead.

So if you’re stressed and you’re not yourself, they’re not, they’re stressed too. And they’re not themselves either. And then you have this sort of fake conversation that nobody loves.

Jeff Pedowitz: Yeah, look, it’s, not an exam, right? It’s not it’s supposed to be natural. It’s supposed to be a conversation. And yeah, look, we’d all love to be Joe Rogan in terms of. Having that massive audience and everything, but I it’s so hard. I, it’s, that’s such an abstract thing to think about the audience.

I don’t know who’s listening when they’re listening, how they’re engaging. And the podcast is on so many different platforms and places. I just really want to make sure the interview is good and I want to make sure the content is good. If the content’s good, then, people will appreciate it. At least I hope they will.

I suppose we wouldn’t be on season eight if we weren’t doing something right along the way, but of course we, like anything else. We’ve made our share of [00:08:00] mistakes too.

Casey Cheshire: Oh yeah. Tons of learning lessons all over the place. What’s fun about this show is that it’s meta. You’re right. Cause we’re talking about podcasting on a podcast and then we can talk about what you just talked about in the context of what we’re doing now. So my question is, how are you feeling?

Are you feeling comfortable right now?

Jeff Pedowitz: Oh, I feel very comfortable.

Casey Cheshire: Cool. Cool. And then tied to that was the idea of if your guest is feeling comfortable, everyone’s a little bit more natural. What does natural mean to you?

Jeff Pedowitz: It doesn’t come off stilted, forced, scripted, like someone’s reading from a teleprompter and you can tell that it’s not them.

Casey Cheshire: Yeah.

Jeff Pedowitz: Look, every guest is different. Everyone has their own personalities. But I do look at it as part of my job as a podcaster. It’s to draw out the natural personality of the person that’s there.

It’s okay if not everyone’s funny. It’s not okay if everyone is completely articulate. It’s okay if some people use profanity. I just want [00:09:00] them to be them. I don’t want them… How would they be if we were just hanging out at a bar? How would they be if we were just riffing on a ball game? That’s who I want them to be on the podcast.

Because I think that’s the most authentic version of themselves. Sure, look, we are… It’s a CMO Insights podcast. There’s a degree of professionalism about it. Yes. But at the same time, that doesn’t mean that they have to force themselves to be something that they’re not.

Casey Cheshire: Have you ever had anyone that came on inside show and was like a little bit scripted or maybe too scripted?

Jeff Pedowitz: It’s not so much about the scripted, but the choices of environment, especially in the first couple of years, like I’ve had some people in their bathroom in front of a shower curtain and yeah, and that’s when we were doing a lot of video and I’m like. Really, dude? Just like no one else? I’d sooner could you at least get it with Starbucks or something?

Casey Cheshire: Totally. I had a guy in a closet one time and you could tell it was a closet because he had a shirt hanging right next to him. And I was like, Hey man, just take that shirt [00:10:00] down and it looks like you’re in a sound booth,

Jeff Pedowitz: one of my favorites, just because I couldn’t stop laughing, is the guy had a pretty big office, and his desk is at one end, and he’s facing the camera, and His admin kept, was doing stuff in the back. She kept walking in and walking out, but she’d keep pausing and she’d stop and she’d look at the camera and, she’s about 10 feet behind him and he was oblivious to it, cause he’s focused on his own neighbor and I’m just starting, I’m like laughing cause she’s just, it’s like in the frame, out of the frame, in the frame.

Casey Cheshire: It’s like you could turn that into either like a drinking game, right? That can be distracting too for the host is when silly things happen. One of the things like that for me that happened is we had a, and it wasn’t my show, but one of the shows that we work with had a guest. Who was filming in her bedroom, and her husband came out of the shower naked and walked across the screen, stopped halfway, looked at the camera, and then backed up slowly into the bathroom and closed the door.

Everyone had a laugh. They had to [00:11:00] pause. The awkward moment was when the host, or the the guest introduced, Are the host to her husband Hey, so and this is my husband. So and and they’re like, Hey, we just had a moment together.

Jeff Pedowitz: That’s happened to me a couple of times too, because I thought it was just audio,

I didn’t realize it was video. I’m sitting there thinking, okay, but just now you’re being interviewed. Why would you have your shower scheduled in the middle of the afternoon, five minutes before this thing? I’m like, a little bit more planning,

Casey Cheshire: wait you had guests show

Jeff Pedowitz: I had guests show up. Inappropriate. So those, of course, we had to just make audio only.

Casey Cheshire: They didn’t figure it out and throw a sweatshirt on in the process.

Jeff Pedowitz: No, we had to stop, pause, and then they went, put something on, but it was just, it was funny so yeah, I think I, I gave up trying to figure out what people think sometimes, just people think different things, so

I just go

with it.

Casey Cheshire: On that note of being natural, that’s a little too natural,

Jeff Pedowitz: That, that is definitely a little [00:12:00] bit too natural,

Casey Cheshire: No birthday suit guests.

Jeff Pedowitz: no birthday, although that might drive up ratings, you never know, but we

might be getting it wrong,

Casey Cheshire: that’s how Rogan got it done.

Jeff Pedowitz: that, that is maybe how Joe did it, I,

I don’t know, I’ll have to go back

Casey Cheshire: podcast,

Jeff Pedowitz: That’s right. We could rename it the Naked Podcast Series.

That should get some attention.

Casey Cheshire: everyone would be disappointed when they show up and everyone’s clothed, but

Jeff Pedowitz: I don’t know. We’ll have to do the haze over it. Like how that show on TV, Naked and Afraid or whatever.

Casey Cheshire: just blur everything so good. Okay. So how we got on this was talking about natural and comfortable and the scripted. But then the idea, we morphed into the concept of content, and is the content good.

And we’ve let ourselves have permission. I love that phrase you gave permission to not be perfect. And then that content, I’ve often felt that, if I’m interested in the content, Then I just hope and by proxy that my, my audience is too. Do you take that approach or how intentional do you get about the output of that content?[00:13:00]

Jeff Pedowitz: we’ll have to do and whatever the guest wanted to talk about or whatever the macro theme is, do we cover it in sufficient detail then. But it’s, I think it’s like anything else, right? You know how you have conversations with people sometimes and it just clicks and then other times you’re like looking for the exit Oh my God, I can’t wait to get out of here.

So I think I’ve had some podcast interviews over the years. I’m like, is it 15 minutes yet? And I’m trying to get it to go. And I’m like, yeah, this is just, I, and then others. 30 minutes flies by, you’re like, I could speak to this person for four more hours, just this person’s amazing.

I spoke with this guy Martin, he was the executive chef at the White House through, for three different administrations. And Martin Mangiello, and that was one of my favorite podcasts. I, he was so fascinating, and the stories, I could have, Done an eight hour podcast with him,[00:14:00] and he was funny and he’s just telling me all the marketing lessons he learned by, by, by being a chef.

And it was really quite fascinating. So yeah, I think really having, good contents, good content, you just do, like I just the interviews clicking and it’s working and it’s lively and it’s jumping. And then other times you feel like. Could you give me more than a one word answer?

Okay, I’m trying to get you to elaborate here. It’s just come on. Work with me a bit.

Casey Cheshire: Yeah, I’ve definitely encountered that and it can be super frustrating to have guests with just one word open. And I have a theory around that, that that it’s cause I’m always trying to improve even if the guest sucks, then it may be, there’s something I could have done better.

Like a prep call or something like that in my theory is that. If they’re doing this one word opens or answers, they may just be out of that zone where they’re not either talking about a passion of theirs or an expertise. They just don’t know, right? So they, nothing to share. But man, if you can find that thing that they love and they start talking about [00:15:00] skydiving, they just come alive.

Jeff Pedowitz: And I think you keyed on something there. It is our job as the interviewer to make a good interview. It’s not the job of the guest. I do take responsibility. If it was a bad interview, it’s me. I didn’t ask the right question. I didn’t probe on the right angle. I didn’t set the person up well for success.

I need to do better. I never blame the guest. It’s never the guest. It’s me. So I either ran the interview well, and it was a good program, or I screwed it up, and it was not. It’s not a good program. And look I’ve had a couple of bad ones over the years. You do a couple hundred of these or whatever, however many we’ve done, I don’t even know anymore, but I just, yeah, there’s been a couple of deaths along the way.

Casey Cheshire: totally. Do you ever not put one out?

Jeff Pedowitz: We have never not put one out.

Casey Cheshire: Okay. I’ve done that once and it was this sketchy ss e o guy that came from a podcast broker.

Jeff Pedowitz: We have had some where the audio was really challenging and the internet kept dropping. So maybe it was a 20 minute session. I, we had to edit down to, 11 minutes or something. [00:16:00] It was a little shorter. But and so it’s a little clipped at parts because of how I but yeah. No, we’ve always put ’em out.

Casey Cheshire: That’s cool. Do you do preps in it before your show?

Jeff Pedowitz: Sometimes usually if it’s someone I don’t know, or sometimes like PR people bring guests to, to, to me or other people bring a guests to me. When that’s the case, and I didn’t really have a chance to reach out to him directly myself, I just like to have at least a first 30 minute prep session. I’ve been doing that, I’d say I’ve been doing that a little bit more over the last couple seasons.

Casey Cheshire: Yeah. And we prepped for this, it was great. And I appreciate you doing that because some people say no to preps, right? But man, do I love that? Just so that when I go to talk to someone, it’s not really the first time and we’ve just got a little bit of familiarity. Just a little, even just a little bit, maybe a lot if we had a chance to chit chat beforehand.

How does your prep call any particular key elements to it? I don’t know if there’s anything that you do that I don’t from your experience with that.

Jeff Pedowitz: I approach my prep call very [00:17:00] similar to how you did. It’s hi, how are you? Tell me about yourself. What’s important to you? What would you like to talk about? Here are some things to expect. Here’s a couple of things I’d like to ask you. Is there anything that’s really passionate that you want to make sure that I cover?

And then I also explain to them, I’m like, listen, I’m not going to have a whole set of questions. I’m going to come in with maybe two or three. That’s it. And the rest, I’m just going to listen and I’m going to riff off of you. So then there are really no surprises.

Casey Cheshire: Do you have any strategies for riffing? Because I feel like that’s an, it’s a cool advanced move to be able to do that and it’s scary for a lot of new hosts to think that they can do that because what happens if you don’t have a question at the ready?

Jeff Pedowitz: I think that’s why you have to have at least a couple that you could fall back on just in case. And then I also have other standby questions for example I’ll, I like to ask a lot of my guests to reflect on their career go back to your early version of yourself coming out of college, what advice would you give them, some things, that’s why I have a couple of go to questions I can pull up [00:18:00] that I like, but, with riffing, I think the key to it is being in the conversation, how do How do you know when to joke with your friends or like how to pivot? And like I said, in a business that you do just cause it’s natural. So I, but I think if you’re not engaged, if you’re not really connecting with the guests and you’re thinking about what you want to ask next, you’re not actively, you’re not really actively listening, you’re partially listening, but then you’re really.

That’s right. Even though I just said it’s our obligation as the interviewer to make sure the interview is good. But it’s still not about us. It’s about the person that we’re interviewing, but if you’re constantly thinking about what you’re going to ask next, then you are making it about you versus the person because you’re too worried about what you’re going to say.

And then in that moment, you can’t riff. Where you can’t riff well because you’re not in it, and like sometimes you get called sometimes like from your wife or your friends, right? Are you listening to me? Are you like watching?

Casey Cheshire: That’s the

Jeff Pedowitz: just saying yes? ​[00:19:00] it’s that

kind of thing.

Casey Cheshire: to me at home, by the way, ever.

Jeff Pedowitz: Yeah never, right? No, I always listen. Of course. Actually, this is really funny. Yeah, the other night I hadn’t made chocolate chip cookies in a while. And so I go to my wife and I’m like, Hey, I’m going to make chocolate chip cookies. And she’s Oh, that’s a great idea. Use the mixer that’s right next to the refrigerator.

I’m like, mixer? There’s a mixer next to her refrigerator? I’m thinking it was in the pantry. She’s yeah, it’s been there, remember I got it for Christmas and we made all the cakes and I’m like, it’s just you make breakfast there every single morning. It is right in front of you.

Literally. I’m like, no, seriously, really? Like, how long has that been there? I never noticed the mixer. She’s you’ve got to be kidding me. It’s literally right here is this thing is huge. And I’m like, I swear I never noticed the camera. So now it’s become a running joke. What else did I not notice?

Yes, it happens. I think you have to pay attention. I think it’s, I don’t think you can successfully riff if you’re not actually in it.

Casey Cheshire: Yeah, it makes you I’m the same [00:20:00] way with the fridge, right? Like, where is the mayo? I it’s like literally right in front of me and I just, I don’t see

Jeff Pedowitz: She’s it’s the second shelf on the left in the basket. Where? And she’s I said the second shelf, not the first shelf, not the third shelf, like the second.

Casey Cheshire: I still can’t find it for the life of me. Please help me find this thing. One of the things I love to do with I like to take notes. Do you take notes when you’re doing the show and you’re asking questions?

Jeff Pedowitz: when I am in sales calls, yes, all the time. I have ever know that. And I take notes prodigiously. When I’m doing interviews now,

Casey Cheshire: Okay. Why?

Jeff Pedowitz: because I know what the interview it’s in the moment. And if I even take a second to write something down, I’m worried I’m going to miss something and I’m not going to be emotionally available. I do it in sales calls because. I have to, to be able to follow up with my team, to think about the proposal, what I want to do next.

I, I have a very good memory, but with the sheer amount of calls I have, there’s no way I can remember every detail of every, call. With the interview, I’m really trying to be present. So now I do [00:21:00] have Open, but it’s with my pre interview notes or whatever I wanted to say.

So I got my bio, the CMO, I’ll have a couple of things that they, he or she said they wanted to cover. And then I’ll have my couple of questions just so sometimes when it gets done, I can reference it really quickly, but I’m not taking notes.

Casey Cheshire: Interesting. That’s, I love this different aspect of, we all might do things generally the same, but we have our differences, so I, I tend to take notes as a way of. paying attention, right? Because sometimes I’m in my mind can wander or maybe it’s my way of focusing on the words and not, so yeah, no right or wrong answer, but it’s just interesting to process that I do write notes, but I will say, I think, I don’t know if it was Peterson, some professor had talked about how you shouldn’t take notes in class, like record it or something, because you can’t, Understand it and write it the same time.

It’s two different parts of your brain. I don’t know if I agree with that, but there’s definitely something there where

Jeff Pedowitz: I think there’s degrees of truth.

Casey Cheshire: what’s that

Jeff Pedowitz: I think there’s degrees of [00:22:00] truth in that. Look, it’s you’re watching TV at night, and you also have your laptop open, and you’re doing some work, or you’re browsing, and you’re half listening and half watching, but you could miss key moments in the scene, or miss key parts of the dialogue that aren’t happening on the show, and then vice versa.

You’re reading an article but you’re missing some key parts of the story that you’re reading or you’re writing because you’re paying attention to the TV. There’s a whole debate around whether or not you could truly multitask and whether or not you could actually be productive. And so there’s a big school of thought that says absolutely not.

You really, it’s a fallacy to think that you can do more than a couple things at a time doing well.

Casey Cheshire: Yeah. I think I prescribed that to the idea that you just. I know I can’t, maybe some people can, but I tend to get super hyper focused on one thing. So I got to make sure that one thing is you that I’m chatting with and not, not email or slack. And sometimes there’s temptation when the show goes.

South to be just like this, this guest or they’re not really giving me themselves. They’re being [00:23:00] fake. I’m trying to be real. I’m frustrated. And I know that there’s been that tendency to just like zone out. But try to fight that and regain control and shift things up a little bit, break things up to try to get that guest to be more of themselves.

Jeff Pedowitz: Yeah, and again, but that’s our job, I think, as the host is to be able to do that. They don’t always go the way you want to. And I love it the most though, when a guest surprises you, ​

It just out of nowhere, they, a story, an anecdote, something that’s really cool.

They’re like, wow, where did this come from? I missed that. Okay, this is really interesting. Now I want to dig in. Cause you, sometimes you have those interviews where it’s flat for five to seven minutes and you’re like, okay, all right, let’s just get through this. We’ll, let’s record it. And then all of a sudden just.

They said something or the way they responded to a question, they just come [00:24:00] alive. And I love those moments because then it also reminds me like, okay. Dig in now. This is okay. Let’s make the second half of the interview like really good let’s get this person like finish strong forget the first half.

Let’s make this next half really awesome

Casey Cheshire: I’ve definitely felt that myself, even at re engaging myself as a podcaster. And, as a fellow marketer, you’d get this, I was on one of those kind of dry marketing, interviews and I was frustrating, but. But my guest then went there, they said, they, they had a position of, they thought all forms should be removed from websites, and as a marketing automation guy, it’s no, I completely disagree with that.

Anyone saying otherwise is just selling a chat bot. I’m like, oh wait, really you? And and I’ve told them in the past Hey, if you say something up, I’ll respectfully disagree to try to have a dialogue. And that just re engaged me right away. Because it was an opposing view. I don’t always have those.

Cause normally I just agree with everything, but that was one where it was fun [00:25:00] and we got reengaged and went tit for tat and debated each other.

Jeff Pedowitz: Those are fun, too.

Casey Cheshire: Yeah. Have you, how do you handle that? How do you handle disagreeing with your guests? Especially

Jeff Pedowitz: I


Casey Cheshire: at a marketing podcast, you have CMOs and you know how many times those CMOs should be hiring the Pettowitz group to fix their shit.

Jeff Pedowitz: if it’s someone I know I’ll be more casual and I’ll go right at him, like just Two guys going at it in a bar kind of thing over a beer. And but if it’s not someone I really don’t know well, and it’s an arm’s length relationship, I will disagree about being more, it’s something more okay, I respect your point.

I’d like to offer a different point of view. I, I think I would take this angle because.

Jeff Pedowitz: Something more like that versus if I knew you, I would actually say, I’m sorry, I think that’s bullshit, like I, [00:26:00] so I could get a little bit more casual with people I’ve known for a while,

Casey Cheshire: yeah, which

Jeff Pedowitz: I’ve not been afraid to throw around the occasional epithet.

Casey Cheshire: Now you’ll have to tell me offline or I want to go listen to that episode. Cause that just sounds great. Just call, and if you’re friends and you can do that, you wouldn’t want to necessarily do that to someone you don’t know, to your point. And this whole thing’s about connecting and that seems like it’s a disconnect, but when it’s your friends that actually doing that makes you even closer because you’re saying, I care about you enough to tell you when I disagree with you.

Jeff Pedowitz: Yeah, look, it’s also more look for people that really do know me. Look I do curse. I wouldn’t say like there’s no every other word coming outta my mouth or anything. But yeah, I’ll use a few choice words every now and then. That’s just how I talk. I’m from New York.

What is what you get. I’m


Casey Cheshire: Do you swear a lot on your show? Or


Jeff Pedowitz: not a lot.

No, not a lot. But I might use a couple, during the show, I, it’s just how I talk, so I am, but. It still is a professional show. It’s still again [00:27:00] it’s not shot in a bar. It is an interview with marketing executives.

It is for a professional forum. So I, if I’m using it, it’s because I’m probably getting really amped up about something or I really want to use it to make a point. I’m not just saying it to say it. But that’s the part of me where I’m trying to be genuine to who I am at the same time, recognizing there’s a time and place for everything.

Casey Cheshire: Totally. With you on that one, I tell people on the hardcore marketing show, Hey, it’s called the hardcore marketing show. You can swear if you want, if you feel like you swore too many times, we can cut them out, like all good, but be yourself to your point. And it’s surprising. I think even just letting people know that they could, if they wanted to, and they can always undo it later, puts people at ease, but then you’re right.

Most people don’t necessarily do it. I’ve had some people on prep calls, funny like a sales coach on a prep call, just F bomb left and right. Like they’re in the military, just blah, blah, blah, blah, blah. They get on the show recording, not a single word. And I was like, okay, [00:28:00] I see what’s going on here.

Cleaning it up a little bit.

Jeff Pedowitz: Yeah, again, I’m I, it’s not like I have to have my mouth flushed out or anything, but but yeah, look I’ve been known to throw them. Look at the title of my first book, right? It’s just, it’s yeah, it’s just who I am. But again, like I said it’s still not about me.

It’s about the guests. If it’s a guest that’s comfortable using that language too, and we’re comfortable with each other, then sure, we could go there, but most of the time, guests don’t use those words, aren’t going to speak like that way. At least they’re not going to do it on a podcast, so I don’t want to be insulting to the guest tonight.

It really is about featuring the guest, not me. So I don’t want the program to remember it. Oh yeah, I remember that show with Bob Jones and where Jeff cursed 90 percent of the time. And that’s an insult to Bob Jones. You know what I mean? That’s not what it’s supposed to be about.

Casey Cheshire: I’ve heard a lot about that too with some people that are trying to be Gary V, right? Who will, as a fellow New Yorker, just drop that stuff whenever he feels like it. But [00:29:00] sometimes, hearing these people, if it’s not you, then it doesn’t sound normal. It doesn’t sound right. He’s being genuine.


Jeff Pedowitz: He is being genuine. And I say it all the time. Like I. Good for him. Love him. He’s awesome, but I can’t be him and I don’t want to be, but yeah, and I can’t be Joe Rogan either. Joe Rogan’s Joe Rogan, Gary Vee’s

Casey Cheshire: And you’ve got good hair. You don’t need to wear a knit cap all the time, yeah.

Jeff Pedowitz: although it might help with my hairline, I don’t know, but yeah, look, it’s being genuine, being authentic. I know there’s a lot of pressure. What does that even mean? It’s just, Be who you are with your friends, be who you are with your kids, be who you are with your spouse, be, just don’t force it.

Don’t try and be something that you’re not, just, and then I think plenty of people love people for who they are, not who they should be, and, we shouldn’t be spending all this time trying to make people into something that they’re not supposed to be.

Casey Cheshire: Yeah. It’s like creating a brand even for like hardcore marketing, I’m not yelling at people on the show. I totally [00:30:00] could, but it just, it’s like we could be hardcore. Let’s be hardcore about the strategies and not the, not going to be Gary Vee Jr.

Jeff Pedowitz: Yes, as tempting as it would be to tell your guests to get their head out of their ass. Might not make for a good interview the rest of the way.

Casey Cheshire: Fuck you, Jeff.

Jeff Pedowitz: Yeah, or it could, I could, I could turn to a street brawl. I don’t know if they could record that, but yeah I think you just gotta, you gotta find the groove.

Casey Cheshire: Yeah, totally. Yeah, I wanted to shift a little bit because you and I loved it. Love this stuff, man. Love the hell out of it. So all that being said, we’ve gushed over podcasting for, good bit of time here. I feel like you’ve rounded the corner, season eight, close to 200 episodes and no end in sight, but that being said what still challenges you or what is the new challenge as you’ve gotten seasoned, you’ve got these episodes.

Are there any challenges or is it all smooth sailing at this point?

Jeff Pedowitz: The actual production part nailed down. It’s pretty easy to do and [00:31:00] my sessions are shorter than some, many others. I know a lot of podcasts go for 30 to 60 minutes. I really try and keep mine between 15 and 20 minutes. And it’s always been intentional, but there’s no right or wrong line.

For me it’s really getting subscribers, how do you promote it? And then some people want to listen to it. And we’re on every. You can think of Spotify and iTunes and I heart radio and all that. And, we probably reach a little over 50, 000 people each week.

How do I turn that into 500, 000 to 5 million to 15 million? How do you make it interesting in a world where there’s so much content, so many podcasts, so many influencers? It’s I think the content’s good. I’m proud of it. I’m proud of the guests that we’ve had. I just, I think the ongoing challenge is how do we get more people to listen?

Casey Cheshire: Yeah. Yeah. And it’s almost like the more you know, it’s a balance, right? It ties back into marketing. The more you try to get people to listen. The [00:32:00] weirder it can get. And then you can potentially sacrifice that normal, authentic you for a you, that’s trying to get likes and clicks.

Jeff Pedowitz: So I’m just going to continue to focus on trying to produce good content and good shows and really hope that it finds its audience, but I think that’s, to me. The biggest overall challenge how do you be relevant? How do you cut through the clutter and get people to listen to something when they have lots of choices?

Let’s face it. How much content can you possibly consume? And now there’s a subscription channel for everything, right? We can have Netflix and Disney Plus and Hulu and Prime, and we still can’t find anything on TV to watch when we have 10, 000 choices. So I think it’s the same thing probably with podcasting.

There’s It’s probably tens of thousands of business podcasts that are out there. So why am I, why now, why you like, I got but that’s the proverbial challenge of marketing too,

Casey Cheshire: yeah.[00:33:00] If I were to ask you related to that your biggest lever to grow your audience so far, what would your take be?

Jeff Pedowitz: Yeah, I think I probably, it’s probably about getting an influencer that has a big enough audience on their own that I can interview. Look I’ve had a chance to interview some amazing people on programs, but generally B2B CMOs were not celebrities, right? They have a

modest following, 10, 000, 20, 000 LinkedIn followers, but not millions,

And they’re not Oprah, right,

And they’re not Simon Sinek and they’re not, so I I think, I don’t know, maybe it takes that, right? To to get introduced to a wider audience.

Casey Cheshire: okay.

Jeff Pedowitz: I don’t know, maybe I’ll have to do a TikTok video or something.

Casey Cheshire: We might have to dance in tutus on TikTok to really get the audiences. I’ll see you there. That said really a final question for you. Cause I’ve just, I love the evolution of this [00:34:00] and we talked past, present. I’d love to just talk a little future with you. If we chat again, let’s say 50 episodes from now 50 of your episodes on your show, CMO Insights.

What do you want your show to look like talking to that future, future you and that future show? Is it the same? Has it evolved? Do you have different guests, different format? What does it look like?

Jeff Pedowitz: Yeah, that’s a really good question. Honestly, I haven’t really thought about it that much, because it’s just one thing of many that I do.

Casey Cheshire: I know. Run a company, family, all the other things.

Jeff Pedowitz: yeah, I don’t know, only going 50. Yeah, I guess I just would want a bigger audience, and people are looking forward to it, that there’s a buzz. People are going to say, Hey, who’s Jeff going to be interviewing this week? Versus… Everyone’s binge watched, they’re all caught up, and now everyone’s in real time.

And they’re looking forward to that next week. That would be cool. And I would feel like, okay, the podcast as a program has reached the next [00:35:00] demarcation point, where people are really looking forward to, okay, who’s going to interview next and who’s going to be on the program.

Casey Cheshire: yeah, a hundred percent. And also that word of mouth, people spreading the word, Hey, he’s about to interview this person. It’s coming up this week. I love it. And they’re getting excited. They can’t wait to get your episode to drop and man, it better drop too, because otherwise you’d be like, where is that episode?

I want to hear, I want to hear.

Jeff Pedowitz: I don’t know, maybe I’ll have I’ll get Michael Strahan to interview me or something.

I like everywhere. I’m like, huh? Does he even sleep? I just he’s over in the UK, he’s at the NFL games, he’s good morning America. The guy’s everywhere.

Casey Cheshire: Maybe it’s not really him. Maybe it’s like an AI bot.

Jeff Pedowitz: Yes, it’s an AI bot, or he has he’s a triplet, really.

Casey Cheshire: Yeah.

Jeff Pedowitz: I am, I’m seriously amazed at these these celebrities and the people that they’re globetrotting. They always look completely refreshed, but they seem to be working at all hours of the night. They’re anywhere and everywhere, and I don’t know, man, by 8 o’clock, I’m good. I’m like, okay, my day is over.

So I sit on the [00:36:00] couch with a glass of wine and watch some TV and go to bed.

Casey Cheshire: Serious. You can only drink so much Red Bull.

Jeff Pedowitz: Yes, it only goes so far.

Casey Cheshire: Exactly. You have to pay that debt one day.

Jeff Pedowitz: Yeah, and then as we get older, man, that debt… You start feeling it.

Casey Cheshire: Man, I’m warding that off as we speak. So on that note, where can people reach out to you? They want to connect you personally on the social side, the pedowitz group, the podcast, throw out some names, some URLs

Jeff Pedowitz: Yeah, I’m on LinkedIn. So LinkedIn slash N slash Jeff Pettawitz. I’m on Twitter. Same thing at Jeff Petowitz, they can find our website, petowitzgroup. com email me, Jeff at petowitzgroup. com. And I’m always responsive, so pretty easy to get to.

Casey Cheshire: Heck yeah. Heck yeah, man. Thank you so much for coming on here. I. I loved talking with you about having authentic [00:37:00] conversations and being yourself and riffing while actively doing it. And it’s really encouraged me to maybe take less notes, but at the same time, really focus on in the here and now learn so much from you.

So I appreciate you coming on here.

Jeff Pedowitz: No problem. Thank you for having me. It’s a pleasure.

Casey Cheshire: Hell yeah. And for those listening, if you learn something. And I know you did, because I literally have two pages of notes front and back over here, then share this with someone else, one person, nine people, 3000 people, 20 million people, whatever. But that’s thought leadership.

Get good information in one other person’s hands, put some comments on LinkedIn, tag Jeff, tag myself. We’ll swoop in. We’ll have a little jungle party and have some fun in the comments. But man, Jeff, thanks again for coming on here.

Jeff Pedowitz: No problem. Thanks, Casey.

Casey Cheshire: All right, everyone. This has been another crazy episode of creating the greatest show.

We will see you all next time.


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