Creating The Greatest Show

[00:00:00]

Casey Cheshire: You hit the button and you may not go back the other way. It's like the airport, when you're exiting that, that door, you can't go back the other way. I've hit the button. And now we're going, and I can't wait to introduce you all to my guest today. He's a badass, a marketing leader, a thought leader, a seasoned podcaster.

He's one of those very special podcasters who have hit the 100 episode milestone and then just kept on going, I didn't even look back [00:01:00] away. He goes, he's the co-host of the zero to 5 million podcast, 120 plus episodes to his name. The marketing team lead at Vanillas Soft. Ollie Whitfield, welcome to show sir.

Ollie Whitfield: Do you wanna be my PR agent? I like that. That was great.

Casey Cheshire: I'll be a hype man, dude. I'll get that big boombox and be like, Ollie is in town,

Ollie Whitfield: Yeah. I'll take it. Yeah. When do you wanna start?

Casey Cheshire: Next week and is it remote? Is this remote? Can I, do I have to go to the UK or can I do it from

Ollie Whitfield: I wouldn't want to put you on any airplanes. You can do it wherever you want.

Casey Cheshire: Okay, if you gave me an excuse to come out there, that'd be fun.

Ollie Whitfield: Don't think I can afford your airfares. You've gotta produce and then I'll reimburse.

Casey Cheshire: You'd have to fly me like FedEx or Amazon Prime right to, to get

Ollie Whitfield: Yeah,

Casey Cheshire: me out there.

Ollie Whitfield: fifth class delivery. Maybe. I can scratch that, but we'll see.

Casey Cheshire: Or I'll just get a rowboat and start. I'll just start. You'll see you in a couple months. Dude I'm excited. You have been podcasting like crazy. You've got a bunch of episodes on your belt. You are not new to this thing. You got the mic, you got the sound, you got the camera, you got the [00:02:00] lights, you got it.

All the experience. So Ollie, pull back the curtain for us on your show and share your most important strategy for a great interview podcast.

Ollie Whitfield: I had to shock you into silence with this one. You ready?

Casey Cheshire: Yeah,

Ollie Whitfield: no rules.

Casey Cheshire: no rules.

Ollie Whitfield: Zero. There are no rules. The only rules are that there are no rules and that's our golden thing. If I want to upload 3 episodes a week, cool, no problem. If I want to do an hour episode, a 10 minute episode, and then a 2 minute episode, cool, no problem.

We can do that. Whatever happens goes pro, provided we're not doing something stupid. We want one upload 22 episodes in a day. That's Little bit much we've got a little bit of an eye towards the performance and those things, but no rules. If I want to have a solo episode, which I'm gonna do tomorrow morning, fine.

If I want to have just a debate with my co-host, cool. If we want to have 2 guests on in a row, if we want to have 10 in a row, we want to talk about different topics. Sometimes we swear a little bit, it's whatever. It's it's us doing our thing, and if we're enjoying it, [00:03:00] you might be more likely to enjoy it.

And if we come up with something that's a bit more interesting that we are gonna have a good time with and can put a bit more energy into than everyone's seen and heard of plenty of podcasts where it's I love what you said there, Casey, that was such an interesting point. Read next question on the script.

Eh, that ain't me. I don't want to do that. And and you won't want to listen to that for too long. So we have a good time by that. we try and throw out some rules out of the window.

Casey Cheshire: Yeah, and one of the rules I like to break is doing exactly what my guest has said not to do. Great. A great answer, Ollie. Our next question number

Ollie Whitfield: expecting better of you.

Casey Cheshire: Man, I hate that. I hate that. But talk to me about where this comes from. What's the origin of this? It's really a myth you're smashing here around podcasting.

The idea that you have to, follow the rules and where do the rules even come from?

Ollie Whitfield: I dunno where they come from. I think it's, maybe rules is the wrong word, but I feel rebellious when I say it. It's the rules, but I think it just comes from here's what corporates have [00:04:00] done. Everyone copies each other. I. I find e even a webinar to see the CMO sit there for 60 minutes and talk through a slide deck page by page.

Unbelievably boring for me. I produced probably in the thousands of webinars. I used to work at an agency, so you have several clients. couple of months, it quickly racks up. Podcasts emphasized the same. You get really numb to it really fast, like really fast. So I've just, I've had a steeper learning curve as it were, or exposure to that.

So you end up disliking it and you end up rebelling from it a bit farther than you would if you weren't. I think spending a lot of my time there, I've just found I I don't like when people ask me monotonous questions or it doesn't really sound like they're that bothered about what I said.

That does not feel very fun. So when, I'm doing it, I think. How do I not do that? And that means if it's gonna be a 15 minute interview, yeah we'll not book you for 20 minutes and take 40. 'cause obviously that doesn't work. But I might go away from the script. Worst that can happen. And our guests or internally, we're always aware of this.

Everything is quality controlled. If you [00:05:00] didn't like anything at all, it isn't gonna make it. So there's, it's completely safe to do whatever. And if we scrap an episode, so be it. That's fine. Or if we want to redo it, that's fine too. I, just think it's personal taste. That's what I'm like.

I I think that's why I enjoy doing it. That's why I learn from it. And that's why probably other people who are listening to it may also learn. because you if you know everything, what's the point? And if you're not learning something you're not particularly gonna ask good questions, are you?

You're not gonna go down rabbit holes. So that's what we try and do.

Casey Cheshire: You mentioned the boring webinars. I remember being a young marketer signing onto a new company many moons ago, and sitting there in a conference room with the other marketing person, the. The architect, somebody else, and just watching as somebody just reads the script for an hour. And I don't know how I stayed sane.

I don't know how anyone stayed on that webinar, but [00:06:00] man, have we come a long way, like life's too short and people aren't gonna sit through that. They're checking their email. Maybe they're passively listening to it. But I, same thing with podcasts, man. And then if you lose interest, Man, it's hard to keep an audience interested if you're not even interested and you're the one doing it.

Ollie Whitfield: Yeah, I've never done in-person speaking I will at some point, but for that, you need changes in your pitch, your pace. It's, I slow down there 'cause I'm trying to emphasize it. But you need those things. You need techniques, you need stage presence, walk around, hand gestures, all those things. But the podcast, you have none of that.

Only the tone and pace of your voice and the pitch, that type of thing. So if I'm interested and I go, oh my God, just made such a like really good point there. That's funny that you said that because I had this story that's so much like that you won't believe it. I sped up, I got more excited. You could tell.

And you will probably pay more attention as a listener. So there's that side of

Casey Cheshire: I did. I was all excited.

Ollie Whitfield: Hopefully

Casey Cheshire: you were just making it

Ollie Whitfield: I was making it up. I do that quite a lot when I have to talk about [00:07:00] my work. But, it's one of those things if especially a webinar too, most people don't actually watch it. They have it like buried beneath another tab most of the time, or on the second screen.

So if a new guest comes on, you pay more attention, your ears prick up. Or if something, someone says, you know what, I totally disagree. And they leave a pause. You're like, oh, tension. I'm listening. I've paid attention. So the, it's that we try and organically create that by having a bit of a laugh at it.

Casey Cheshire: It is more natural too. That way it, that's how we actually talk like it when you transcribe how we actually talk. We do say likes every so often. We do have ums. We do pause and think about our thoughts, mid thought, but. Somehow we're able to parse that and we enjoy that. And it's so much better than saying, Ollie, thank you for being on the show.

Here is my canned response and then something. What about that is just so much? No one wants to hear that, right? What about that? Organic, natural, [00:08:00] flawed, imperfect, varying pitches Do. Why do pe, why do we like that so much? Do you think?

Ollie Whitfield: I think podcasts that I really like, I feel like I'm their mate a little bit.

I'm not, I've never met them. That's really sad. A whimsical, but. I feel like if you've listened to them, you've spent time with them. It's like being in the pub and chatting to your mates a little bit. Even if it's business stuff, it's like having happy hour a little bit. So I think when you are, you get to one of the co-hosts and you think they're funny or you think that one's a bit, more like you, you can tell by how they talk.

You really can't get that by the corporate. If it's a hiring interview, you, there's no personality. It's just gotta be. So Casey, tell me about your experience. And then I have to let you do the talking. If I sound like that, like you, you will never get to know me and no one ever wants to take their interviewer for a beer.

So it, you have to do the opposite.

Casey Cheshire: To the opposite. Now it's so cool to say don't break the rules, but I did catch one of the things you said in there, [00:09:00] which is, okay, now don't be stupid. Don't. Take the cool idea and then just run it off a cliff. So how do we know we're being stupid? How do we know we're taking it too far?

Ollie Whitfield: Oh, you asked the difficult questions. Why did I come on this show? I think you just have to realize what's my own bandwidth telling me about this? If I wanted to do 25 episodes in the next week, I probably can't actually do it. So there's that level. How far in keeping or away from what we already do is what I'm thinking about.

So we do normally 20 minute episodes once a week, something like that. Most of the time it's a guest interview, not always. And it's normally about something to do with business growth, hyen sales. If I was to pivot really far and go into accounting in a deep way, probably just alienates the audience probably.

I think that I'd call further than across the line than I'd want to go different if I said 'cause we're talking to founders so different if it's the [00:10:00] Founder's Guide to Accounting so you don't blow up your business. Maybe, but not too far. So as long as I can. If I why? If I did a three year old test, then it's all right.

If I can't draw the line reasonably after three why's, then it's probably a little bit too far. It's the why is the deep crash course of accounting relative to us? Because they're founders. 'cause they could buy from us. I'm getting to two. Whys not three? So the three Why test is my thing.

Casey Cheshire: Okay, cool. Here let's let miss test that. I broke a rule in honor of you without realizing it. Last podcast recording I did from my marketing pod and something about the guest and I, we were riffing, we're having a good time, and we started the show with some A S M R, right? We just started whispering it to the mics.

You started scratching on a can and we just had a good time because we just did, and it was silly. And it, so doing the y test. What would you ask yourself that is that okay to do?

Ollie Whitfield: [00:11:00] So why did you do it? 'cause it was fun and silly. Why was it fun and silly? Because you were vibing with the person. Why were you doing that to make a good episode? I found that fairly easy to do. I'm saying that's good.

Casey Cheshire: Cool. Dude, I like this. I feel like you are the magic eight ball of podcasting and I would encourage everyone to reach out to you on LinkedIn and just ask if. If you should violate a rule, ask Ollie, send him a message. Say, I'm thinking of doing this, thinking of doing a Chinese water torture, magic trick, live on the pod.

Should I do it? What would

Ollie Whitfield: liable for you getting fired, just saying disclaimer.

Casey Cheshire: But I, but that now, I guess that's one of the things in there too, is, what kind of a culture, what kind of a brand is the company you work at? Especially if you're doing a corporate podcast, how far can you push that? I've seen people dress in cow costumes and push it as far as their leadership can handle.

Ollie Whitfield: Yeah, I don't dress [00:12:00] up. I normally look something like this. I'm in comfy wear. My comfy, we don't have the most outlandish. Brand ever. We're not, wearing city clothing or stuff like that, but we're a little bit like the family next door, nice people type thing. That's the vibe we go for.

So it would be weird if I showed up in like a cowboy outfit for my next podcast. That would be, what the hell. But if I wanted to blow up the format a little bit, if I wanted to just riff on a personal story, if I wanted to throw away the script and say, you know what, we just started talking about this thing.

No one's talked about that before. Let's just talk about it. That's totally fine. And if you're in that type of company that is corporate, that's probably all you need. You don't need to go the extra eight miles. Going one or two inches is probably further than a lot of people have gone.

If you're in a really corporate type of place. So if you're in some global enterprise, crazy large company and it's edited to death, yes, it'll probably still be edited to death. But your different approach, one episode every now and then. He's not gonna kill anybody. And if you really get [00:13:00] vetoed, then unlucky, but you know that's on them.

Not you. You, if you're just gonna do the same thing over and over call, but after a while people have had their fix.

Casey Cheshire: Yeah the novelty. Can it really attract people? Question Magic eight. Ball podcasting. Should you shotgun a Red Bull? By the way, do you have that in the uk? Do you have shotgunning, shotgun, a beer

Ollie Whitfield: That's basically chugging a beer. Stick

Casey Cheshire: Yeah, but it's different though because you like punch a hole in the side of it

Ollie Whitfield: Oh, okay.

Casey Cheshire: quickly you drink the beer.

Ollie Whitfield: Some people, not me, they're able to open their mouth wide enough to pour it straight down, so you don't even do anything that's, I can't do

Casey Cheshire: Yeah. That's crazy. Now, should you do that to a Red Bull before doing a podcast interview?

Ollie Whitfield: Each Toro probably not if you're diabetic. I don't, I'm, I find this fun and exciting anyway, so I'm good. I've literally got a half a pint of water, so you know, I'm all right. But if you need a bit of sugar and stuff, you go for it.

Casey Cheshire: They do have sugar free, just so we're fair.[00:14:00] But yeah, it's funny, I actually did, one time before a presentation on a stage, I drank a little bit of Red Bull to gimme some energy, but I drank too much Red Bull and then I was just like super speed talker on the stage. And by the time I was done, people like, what did I just listen to?

Ollie Whitfield: Yeah, you're a blur

Casey Cheshire: even stop to take a breath. Not recommended. Not recommended. And, dude, like this is all fun and honestly I could keep asking you questions for an hour and that would probably be another show. I think what's cool about this is I heard you say this too, if you're enjoying it as we, as the host and guests are enjoying it, then you will too.

The audience will too. The listener will too. And there's something about you enjoying it that transfers to everyone else, or can, talk to me about that. Is that something on the forefront of your mind? Make sure you stay in the zone where you're having a good time.

Ollie Whitfield: That's more than not episode planning. I enjoy the media side of my job anyway. I find it quite fun, but not very many people think about it really. How many [00:15:00] people get paid to have a chat? I. That's recorded, like not many. So we have to, call it a good day when it's a good day, so I take that as a, I'm quite lucky to do that.

Very happy to keep doing it. So then it's just a case of if I have to talk about something really monotonous, so at least try and make it a bit fun. 'cause then it stimulates my brain and then I'm awake to it if I have to deliver a PowerPoint for quite a long period of time. I actually find that quite nerve wracking.

I find it, I'm sweaty, I forget to breathe. I do all of the speaker things when you're on stage and you freeze. I do that 'cause I don't like it. 'cause it's not fun in my immature way of doing it. I, it's, you have to find a little bit of a balance and now I can do that. It's, I don't, I didn't like it at first, but you get better.

But I think that's our episode planning. So for instance, tomorrow, I'm I looked at the first cold email I sent for us when I joined here about two and a half years ago. And then I'm looking at the most recent one I sent. And I'm gonna egg on my face a little bit. I'm gonna say, you know what?

This is pretty crap. And I liked what I was doing [00:16:00] there, but that's shocking, bro. What was I doing? And then I'll look at my most recent one and I'll say, dude, you haven't got it any better. You need to have a real look in yourself in the mirror. And that's a good laugh, that's a bit of fun.

And I can poke jokes on myself. It's almost like writing your own comedy. You know what kinda. Angles you're gonna take, you know what kind of rabbit holes you might go down. With that, it's quite easy. Or in school, I always used to have when we'd have a debate, I'd take the hard side of it.

I don't know why. I am just weird like that. I enjoyed having a debate and I quite often win. So when we have a debate with my co-host, I let him pick and sometimes I win. We don't always have a jury, but, I like to, it, it challenges me. So there's a little bit of that anywhere I can. Extract some motivation, extract a little bit of inspiration outta myself just through the concept of the episode itself.

That's all I need. And then I start,

Casey Cheshire: Yeah, debates. Let's talk about that for a little bit, because I remember being, this ties right into the fun thing too. I was on the marketing pod and I was chatting with this person. [00:17:00] We weren't vibing. I wasn't feeling it. It's probably me, but I was just not interested. We're having the same marketing conversation.

That I've had a few times. When you get a lot of episodes, you start Groundhog Day, you start talking about similar things and I'm, so I was mentally almost checked out and then they brought up something that they felt really strongly about around forms and marketing forms and they're like, get rid of all of them.

And I tend to like to keep those 'cause I like that stuff. You just gotta do it the right way. And so I was like, oh wait. There is something we disagree on. And it was exciting. I woke up, from just listening to the drone of a podcast. Not that they were bad per se, but I just, it shook me out of my, my, snooze.

And I actually was excited and we had a good conversation and we chit chitchatted and it woke me up. But I don't often disagree with my guests, like I would love to disagree with you on something, but I would imagine we probably agree on almost everything.

Ollie Whitfield: I'll find a way, [00:18:00] trust me.

Casey Cheshire: Do And do you like look for ways to debate beforehand

Your prep?

Ollie Whitfield: so it's a difficult balance. So I remember many years ago there was, I won't name the names to. Be a douche bag. But there was a a super cringe really cringe thing that people in our industry did. They did a pretend boxing match. They made like a whole contrived PR thing about having a big spat, a big disagreement publicly.

It wasn't you before you think of going there. And they made it into a webinar and they had someone host it and it was, they really played on, this is like a boxing match in the blue corner, in the red corner and all that. And. How it transpired. Excellent tactic. Really cringey and corny, but excellent tactic.

Everyone paid attention. God knows how many people went to it, but they ended up just backing off and agreeing with each other a bit in the show. It was, it became super obvious that they'd really made a thing of it. So that turns me off. I'm not here to get you in and then just, Controversy gone.[00:19:00]

We don't have to have a shouting match, but I think I just take the angle of, here's two contrarian points of view. Where do we land? And and one person's gotta take one so long as it's related to our industry. For the most part, the big one for us, it's usually cold calling is dead, is it or not?

Or cold email versus cold calling or LinkedIn or not. There's some yes or no, black and white type things There. There's plenty of them. And the beauty of it is no one's right, because the answer is actually it works for someone, it works in a different way for you, or you're doing it the wrong way.

So there isn't an ultimate outcome and there's lots of different ways you can explore that. And I enjoy the mental game of chess as if to say, you took this angle mistake. I've gone round the back and got you there. So my co-host enjoys getting beaten up by me like that. But yeah you have to try and think of a way to make it Not too corny.

'cause that's when people get turned off. You can have the, is calling is called calling dead debate. Sure. Everybody's heard it. You need to have another way now to do [00:20:00] that. It's like saying forms or no forms. Everybody's heard it and it's really nuanced. So what about no forms or forms? If you're a small business, that's very different and then you probably have a better argument.

But yeah, I I try to find just. How can I make this nuanced but appeal to enough people that it's gonna get a little spicy?

Casey Cheshire: That's interesting. So gi give it a little bit of a flare so it's not so broad, but it's quite narrow. I think I remember hearing that similar kind of thing just to. Talk marketing and sales. I remember hearing a debate in a panel, which was like, where should the S D R team live? Should they live with marketing or should they live with sales?

And that, broadly speaking was too broad of a topic, but if they gave it more parameters, it'd be easier to tell where that might live. And that ended up having a good conversation. One of the things I got from you just now was that it doesn't, you don't need to have a drag out. Black or white, this answer or [00:21:00] that answer to have a debate.

You could just have an approach or have a different angle than your guest. So I would love to, to ask you this question, 'cause you mentioned doing a 20 minute show. Do you do all of your shows, do they tend to be in the shorter length? Do you ever do any long ones? What do you prefer?

Ollie Whitfield: Most of them end up being about 20 minutes or so. 15, sometimes 10, if it's a, if it's a shorter one. But yeah, around that normally the cap off would be half hour. 'cause most people live in half hour blocks in their calendar. So most of the time it's that.

Casey Cheshire: Got it. It, now, have you ever done the long ones? Do you just prefer the shorter ones or why do you end up doing the shorter ones?

Ollie Whitfield: Stylistically. We like to cover a lot of different topics and I've done hour ones. I've managed plenty of shows that were every week or an hour. Not that podcast tours ever give you very good stats, I have to say. It's not like you can look at the average listening and say, Now everybody dropped off at this time, so you don't really have that.

But I would imagine, and I hear anecdotally [00:22:00] sometimes, yeah, I got through most of it on my run at the gym, that type of stuff. And then the next week's one came up, so I listened to that. So I'm not too worried about, can I get you to consume 45 plus minutes? Cool. I think I find it less intimidating.

Personally. I listen to several podcasts. It helps me sleep. So I have quite a few. I have Joe Rogan 'cause it's three hours. And then I know for sure I can, even, if it takes me an hour to get to sleep, no problem. But if I've got 20 minutes before my next call and I want to listen to something while I work, it's not like I'm halfway through it and context switching.

So we we try and do that. It's a business one. I respect. People are commuting, maybe listening to it on their lunch break, listening to it, in the office listening to it, something like that. But yeah, they're not, they're, hopefully they're not laying l to their wife or husband listening to us.

I hope.

Casey Cheshire: No, and it's the reason I bring it up is I don't think it's necessarily debate between the two of us. There are some great benefits of the short quick ones. One of which if you do five minute episodes, you get a hell of a lot more [00:23:00] listens. Yeah, look, I have, a thousand listens and you only have 300.

Yeah. But mine took, 12 times as long to get through. But I guess those are vanity metrics in the end. If we had only talked for 20 minutes, we would've been done 20 minutes ago. And I just think of the good conversation and where this has been and I think I'm into it for, learning and connection and relationship and that kind of thing.

So my goals are even beyond just the content wins. Yeah, I don't know. I just, it's one of those things where I don't feel like the short pods are bad, I just, I prefer the longer ones.

Ollie Whitfield: It is a good it's a good debate. Maybe we should have that, but,

Casey Cheshire: All right. Let's do it.

Ollie Whitfield: okay, let's do it. I think shorter ones they're more digestible just because they're shorter. You can get through it quicker, obviously, less amount of time. I think people get less intimidated by it, but obviously it does depend on the goal.

For me, in my org, in my context, in our team bandwidth from those things, the goals, the things that we're trying to achieve we need to get things out. We [00:24:00] need to establish the presence. We need to grow the brand a little bit. We're it's for order close our sort of secondary product line and it's got a lesser audience.

It's less established than the bigger company in Oof. So if it was the other day around, probably an hour, most likely an hour 'cause of the listenership. But if we want to grow, we need to get at bats. We need different people to get their audience. We need different topics to get the ss e o juice and that way around.

So I know that you may have a different context there to back that up, but for me, in that situation, that's the play.

Casey Cheshire: Yeah, and this even brings to mind like the idea of, what's the context or narrowing down the topic. 'cause you're right, like depending on the goal of the podcast, you may have a completely different length. For me, I think about Rogan and I, three hours long and I now I consider like a Rogan, a unit of length of time, oh, that, that podcast is a half rogan.

Or we're a third Rogan in this show. And, but what's interesting is we've all had those experiences of listening. To an entire three hour episode. Not all at [00:25:00] once usually, over the course of several days. And it's almost like we're either listening to a couple minutes and we don't like the guest or man, we are tuned in to that crazy archeologist to that.

I will say when who is it? The when Lex Friedman, when Lex interviewed a an evolutionary biologist, that was a great sleep medication for me. 'cause that was intense. But when it's not that, when it's someone who has an interesting story to tell. I think there's one particular time where Joe actually broke his three hour thing.

Like he could be talking to. The lead singer of Aerosmith, he could be talking to whoever and come through hour three. He's thanks brother, I'll catch you later. And boom, bumper music. And he's out, like he's not going over three. But I'm pretty sure when he talked to Jewel, he went to four and they just kept going.

He just kept talking because she just has this most bizarre story and crazy story whether you like her music or not. Just, it's so interesting to hear. And if people can go to four, why [00:26:00] not go to one?

Ollie Whitfield: True. How many Joe Rogans are there though? Just one.

Casey Cheshire: It's true.

Ollie Whitfield: There's a balance there. I think it, and it depends what role you play in someone's life. I think Joe Rogan in my life, to pick the example up he's my sleep therapist a little bit and he's my dead space background noise a little bit. And he probably plays a 10% of my day, which is quite a lot actually, if you think about it.

Casey Cheshire: Yeah.

Ollie Whitfield: What my podcast is playing in someone's day is something more like a 1% of their week. And we cool with that 'cause we know that they may be it's a business as well. It's a little different to Joey. He's lifestyle and all that. Beyond that, we know that work is eight hours of their day, which is a third of their day.

And then beyond that, listening to growth stuff and learning stuff is probably a fraction of what it should be of their time. So then if you narrow it down I don't think I need a three hours to try and fill all of that. And even if I did three hours, who the hell am I? Like they, they probably don't care if I did 10 hours or one to be fair.

So [00:27:00] I think it's what piece of your life, of their life are you trying to be from that woods. But if you're a really big deal, like if you're a super duper stage speaker, circuit speaking book author, guru guy, then maybe. But maybe you are but me and Sean we're not quite that.

Casey Cheshire: But it does, the differentiating between is this. Background noise. I think sometimes the benefit of a longer pod is you just hear these people talking and you just want to be in the room with them, and it just, it's, they're vibing. You're vibing, it's Elon, doing what he's doing, talking to Joe, blowing his mind or someone else about ancient civilizations or whatever the topic is that fascinates you, to be a fly on that wall in that room, the longer it goes.

The better because you just wanna be in that room. But I also hear what you're saying because. You maybe aren't listening to everything. Whereas when I think about listening to a book on audible, especially if you get that speed bumped up a little bit, I have a recent, book I've been listening [00:28:00] to.

Man, if I check out mentally for 30 seconds, we're in a different galaxy, literally. So I need to go back that thing up, hit back 30, or even start the chapter over again because I'm lost because I wasn't paying attention. Now that's fiction, but even like a non-fiction, it's all jammed in there.

You really gotta have it in your like, active window, right? You have to be thinking about it. So it sounds to me like the shorter span is that highly, I don't wanna say produced, but highly thoughtful. 20 minutes, let's give you value in a short period of time and let's get you outta here.

Ollie Whitfield: If you're trying to say more valuable, then I think I won the debate, but. What your play for a longer one is you're going for like media saturation is the thing. It's okay if you miss it. J Joe Rogan's three hours a day. Who the hell is listening to all of that every day? Like literally no one get a job if you are like, or well done to you if you've got that attention span.

Seriously. I don't do it. I pick and choose what I listen to and it lasts me a long time anyways. But yes, it's dispensable because you're not worried about it 'cause you know it's good stuff and they'll be in good stuff again. [00:29:00] If it's lightning in a bottle, once in a while you pay attention to it more.

So I, I think there's a little bit of both, but it's easier for us with our skill, with our presence to say, here's something really good in a short burst you'll be looking forward to this next week than to like mass produce and overwhelm. We don't have the bandwidth for the people or the planning perfectly honest to do that.

So maybe we could, to go upscale, we could go to an L like you said, I don't know if that achieves the mass saturation type thing, but. It's a step toward

Casey Cheshire: Cool term, I'll definitely have to really think about the mass saturation point. I would say a killing blow in this debate, if you will. Such a friendly debate. Imagine if all battles were like sir, I do think X, Y,

Ollie Whitfield: excellent point.

Casey Cheshire: but what if you stuffed. The first 20 minutes of an hour long podcast with the kind of format that would deliver the same kind of value a 20 minute podcast would do.

But then if you like it, you can stick around for the rest of it like a particular show like this one or my marketing pod [00:30:00] where we have that big leading question. We get some value out right away. If you wanna check out. Cool. If you want to hang out and have Ollie and Casey just geeking out, debating random shit and having a good time, do that too.

Best of both worlds, but you get options.

Ollie Whitfield: I've been on a show who did that. He did. Now I forget if it was the first half was a podcast or a webinar and the other half was the other, I

Casey Cheshire: Oh, wow. Webinars. So you took it hardcore?

Ollie Whitfield: Yeah it was cool. It was a LinkedIn Live thing, and then it went offline to whatever media it then became I don't remember but that was cool.

I don't know how much the audience trade off was there. And again, fit for his business model. I think he was a consultant trainer. So if you're looking for like the, Instagram to Patreon subscription thing. That's the similar equation. So yeah, it depends on the business model for our type of thing.

And it's not the auto closed podcast 'cause no one likes brands, but it's top of funnel. It's just what can we reuse this for and who can we get to see us for the first time? 'cause we're [00:31:00] talking about other stuff than blogs on how to write an email. So for that it's different. But yeah, I totally see what you mean.

Casey Cheshire: same here man. I did a a co-host type podcast the other day. Just for fun, is me another guy, and. We went for 20 minutes or half an hour or so. 'cause just us, we didn't have a guest, didn't have anyone else adding anything to the conversation and we were completely unscripted. So right about 20 minutes it made sense to call it a day.

Wrap it up and get to the next one. Keep it tight. Because I think to your point, whether you go short or long, you wanna still be able to pack that knowledge in there. And as soon as either one of them is starting to drone on and tread water and drowned, it's probably time to call it a day.

Ollie Whitfield: One night I listened to the, they're two YouTubers and they're, they talk a lot about the creative space. They're Tim Ferriss on their last one, so he's been doing so many podcasts. It's unreal. They just asked him, so how do you like do this? You're, he's doing it with a-listers as well.

He's had, Schwartzenegger and God knows who else, how do [00:32:00] you get them? And they're used to media, like super used to it and quite resistant 'cause they know how bad it is. So he is like unbelievably prepped. You wouldn't even believe it. He's listen to the last 50 media appearances they did, listed all of the same questions to see trends.

He's got rid of them. 'cause they just zone out as soon as they hear the same. So tell me about the latest movie. 'cause they're like, oh, again, he's list, he's listing out. Like what what common stories do they have? Like home run hitters basically, when you go on the talk show, what's your funny story?

He's listing out them so that if if I join and you sense I'm a little bit nervous, I'm a bit uneasy. I'm not really forthcoming. It's not flowing. You can slip in that and you can say, here's an easy at battle, let's get started on the right foot in here. So he takes it to the N degree. Most people don't, but but if you're gonna go that distance, you gotta be prepared for that.

'cause there, there's nothing worse than knowing, you know what we do a podcast, it's usually an hour. I don't want to put out a 25 minute episode 'cause that's gonna look weird, [00:33:00] but this is so boring. Like you've had before, we've all had it. And I've been to episodes for that before.

But I think you have to come in extra prepped and for that, I think it makes you a better host actually as well. If you can do that. Props, do you deserve it? If you can keep the energy high for that longer period of time, that's more skill. For me I alternate with my co-host. That's just to keep it interesting rather than just one voice.

But, for 20 minutes, 30 minutes, it's not that difficult. It keeps, it really lofi for us. If I'm having the worst day ever, I can still roll into a podcast and doing a right job, whereas it's a bit more of a real conscious thought to be 60 minutes.

Casey Cheshire: That's a lot of prep. That's interesting to hear that. Do you know who those guys that were interviewing Tim,

Ollie Whitfield: Yeah. It's called the Colin and Samir show. They YouTubers, they care a lot about the sort of creator space. They talk about a lot a lot about YouTube and. How it all works and how they're becoming business people rather than just people with a camera. And they talk to [00:34:00] all of the big people on that space, but also Tim Ferriss, they like podcasting, their newsletter, all these things.

Casey Cheshire: We will definitely link to that in the show. It's interesting, Tim sometimes is the kind of guy that. I will intentionally depart from some of the things he does. To each their own, right? We were talking about no rules in the beginning. But even just sometimes he will do those rapid fire questions and I've caught him pivoting to the next one as opposed to following up on that thing, what's your favorite, do you have that book? Have you, you gotten that book? Tula Titans.

Ollie Whitfield: I haven't read any of his stuff. To be honest. I've not consumed too much of it either. I just know of him and he's at the top of the charts all the time, so best of luck to him.

Casey Cheshire: Tool of Titans is really fascinating. It literally is the width of an I of an iPhone, right? It's like really thick. It's like a tome, and every two pages is a different podcast. Guest that he spoke to on his pod and he has the benefit of asking them all the same question. Now it sounds like he's asking them a bunch of [00:35:00] curated questions, but he also asked some of them the same ones what's that one purchase you can't live without?

Which is really fascinating to hear and see all different people's things. The problem with this book though, is I end up coming out with 20 to-dos across. 15 pages and I gotta try this tea, I gotta buy that. I gotta do this. It's fascinating. It's not a book you read from cover to cover, but the amount of takeaways you can have from just asking the same question of all these rock stars.

And it's fascinating, but sometimes he does just cut off the question and go right to the next one, and I wish you would dive a little deeper into it.

Ollie Whitfield: Yeah, it's a known when they do that. Maybe he's pressed for retired, maybe they've gotta go. But it's just good content planning. We've done that a few times. We've had eBooks where we've just transcribed 20 podcasts and we've got 20 experts. So it's the 20 experts ebook. It's the same thing. It's just repurposing and on that scale, when you've got Arnie and then.

God knows. Whatever a-list though. Yeah it sells books quite easily, doesn't it? It's Wouldn't you wanna know his morning routine? Yeah, I would.[00:36:00] And you've got 10 questions like that, that are clicky worthy. Yeah, for sure.

Casey Cheshire: It'd be funny to have a spoof of that. Here's 20 people you don't know and hear their morning routines

Ollie Whitfield: Yeah. Yeah. Here's Ollie's morning routine. There. It doesn't exist. Move on. Next question.

Casey Cheshire: wakes up, looks at clock

Ollie Whitfield: Yeah, dose is over.

Casey Cheshire: to get to work. Yeah. You mentioned this. Maybe Tim was rushing to, to hit the clock. Talk to me about time management. 'cause oftentimes I see podcasters when they first start, it's all about questions and follow up. But eventually they got a good knack for that. And then it just becomes about not running out of time or figuring out where to ask those key questions because that heart stops coming, whether it's 20 minutes or an hour.

And you gotta get those questions in if you can.

Ollie Whitfield: That's just pure skill. The interviewer has to know how to do that. You can only learn that by doing it and messing out up a few times. Unfortunately, just like speaking [00:37:00] training, you can only do your first stage speaking gig and you can sweat bricks and look like you're nervous because you are, you have to do it.

The only one thing that you can do, I think, is you can set the stage beforehand. So before we get on here, if you want to say to me, look I've got 10 really important things I want to go through. It's gonna be quite a lot. So I want to get depth, but let's, can we refrain from five or 10 minute stories because it's really gonna squeeze us.

So occasionally I've had that on webinars where someone wants to really riff and go into something quite in a long tail way. That's okay. I have to be able to give them rope for that. But within reason that, it's your show, so you're telling them how to do it and how to be a good guest on it so that they can get the maximum benefit from it, from looking really good on it.

So there's a little bit of both there. I think you just, you have to. I try and divide it up and be a little bit conservative if I've got a webinar. 'cause that's, it's more like an hour to, to equate to your time. I know. Roughly 15 minutes per big topic is about, okay. Maybe [00:38:00] four topics, about 10 minutes and then we've got some wiggle room.

Leave some space for intro, outro and some chat in the middle. That's all right. If I know. We started at, two 19. It's now 2 39 and we've only got on topic one. I know I'm behind. So there's just a little bit of mental. Make it small, make it easy for yourself to keep log off. You don't have to look at the spreadsheet and say, oh, I've only asked one question and you know this and that.

I just try and break it up by time and say, loosely, we're about on track. We're a bit ahead, we're a bit slow. And then you can go from there and if you want, the best thing to do is be ahead. 'cause you can always ask a follow up.

Casey Cheshire: Can always ask a follow up in it. It only takes you running out of time. And sometimes your guest will have time, which is cool, and oftentimes they won't have time. And I definitely have run into that. Zone where you're riffing, the guest is on fire, and then they send you that message on Zoom or squad cast or whatever platform, and they're like, I have a hard stop in five minutes.

You're like, oh God quick. And [00:39:00] maybe, maybe your close is gonna be a couple minutes. And they're in the middle of a story and, oh God. So I think, to your point, pure skill learning the hard way. But I guess the good news is if you're experiencing that as a host, You're probably transitioning from that beginner phase to more advanced phase where you're thinking about the clock now and managing that which is fascinating.

And so I even think about the kind of questions that, how much time do I have left, right? And what kind of cool questions can we fit in there? And I have the next one for you, which is this, like that pause. That was a good pause. Shake it up a little bit. Everything's awesome in podcasting, but.

What's your biggest challenge right now? What? What's the thing? Everything's rosy except for this with podcasting for you?

Ollie Whitfield: The analytics are still pretty dire, I think at least the tools that I use, and I don't think I know anyone who's really happy with that. That, that's just a bit of an annoyance. But the main problem, which links to that, is I think it's very [00:40:00] hard for the most part to actually gain listenership your your tos, your Instagram reels, your YouTube shorts, your whatevers.

For the most part I would imagine, and it's hard to notice, but just broad strokes, if you, whatever viral, YouTube, short you post, it's unlikely to produce you that many new listeners who actually bother to, oh, I've gotta click to type and search and do effort to do this. I think that's really hard.

And it's you can't blame people. Joe Rogan experience on YouTube, the clips thing, 10 minute clips. They're like multimillion view clips, like all the time, or the YouTube shorts the whatever that he will post, they get super viral and obviously it will when you're as big a presence as he is.

But for the average company or person, people who are trying to do this, that's just completely unrealistic. So to do that, yes, it's a good practice. Yes. It's following the right trend and if you keep at it, it might become something, but it just isn't gonna. Get you 10 new listeners this week, or even 10 or even five, or [00:41:00] even two maybe.

So that's the tricky thing. And even if they post it on their LinkedIn, even if, 'cause that really isn't a guarantee. And even if your creative's good enough, they still may not bother to do it. They still may have a marketing team running their LinkedIn profile who don't want to post external things because they're busy.

Then you're really relying on who can I like, get to post about this and. Like, how can I get them to even bother opening the podcast app? Because when you're on your desktop like we are right now I don't really listen to things like that. I can play Spotify out loud, but that's it. I don't do Apple Podcast out loud because why on my laptop.

So it's tricky to get people to cross the bridge from where they are and where they see it to going onto it. And no one really knows in YouTube it's a very well established algorithm. In LinkedIn, it's a very well established algorithm, same as Facebook. It's not really the case with a podcasting platform.

No one really knows how do I get up in the Apple podcast charts or how do I get up in Spotify? I couldn't tell you and I don't know anyone that does. So how do [00:42:00] you do that? And I think a lot of people, besides if you're a big figure, besides if you're a big brand, besides if you get big speakers, it's probably the only way that everyone goes to.

It's really tough. And I think a lot of

people are slower than they think.

Casey Cheshire: to your point, Joe was asked or someone was asked, how do you. Make a successful podcast. Step one, be famous. Step two, start a podcast. So to your point, yeah, like it's not like listeners growing trees. And as you were talking, I opened up Spotify and I typed the zero to 5 million podcast.

There you are. Made sure follow is on there. Ring the bell.

Ollie Whitfield: When I saw our Spotify followers, I was like, shit, that's way more than I thought. 'cause our stats indicate different stuff. It's really inconsistent. It's so annoying.

Casey Cheshire: Different platforms. Then you throw YouTube gives you more analytics, but it's separate from all the listens and do you aggregate or whatnot? Yeah. Analytics is still analytics and listeners. I hear you on that as a way to gain and a [00:43:00] real challenge still

Ollie Whitfield: why isn't subscribers an a valid metric? They must know that you've clicked subscribe. It's bloody obvious but I dunno if I've ever seen that on anybody's podcast.

Casey Cheshire: Yeah. Why not? That's weird. I would wanna see that. I've seen that on some apps and it, but not the biggies, the ones that I really wanna see it on. It's weird. I have a bit of a hypothetical question for you now, let's say, I may or may not have a time machine, and we go into the future and we get a chance to check out your podcast 50 episodes from now.

Let's say it's weekly and you got those episodes, you might break the rules, and so 50 might be a couple weeks from now, but let's say 50 episodes from now. What do you want your pod to look like? Do you want it to change any? Do you want it? What does it look like? What does it sound like?

Ollie Whitfield: Yeah. So we're probably rules being broken six months, a year away, roughly. So it could be end of 2023. [00:44:00] Wow. That's weird to say. I think it will be slightly different. Same core tenants at play, but I. I would like to be a bit more smart about how we repurpose things. So our episode planning could be a little bit more intricate rather than just oh, we need a guest.

Let's get a guest. Cool. Done. We can do that. But when we have a debate, when we have a separate topic, how and why and what else is that supporting? So for instance we've done we've done webinars where we've parity family feud. Great fun. Bloody difficult to organize, but really good fun

Casey Cheshire: You pared? What?

Ollie Whitfield: family.

Feuded the TV show. I was Steve Harvey, so

Casey Cheshire: yeah. That's

Ollie Whitfield: my, it was my team versus ard, unfortunately for ard, they lost on the last question. They played it perfect. They just didn't steal the round. So they're the won. But brilliant fun and we've managed to make three episodes of the podcast out of it.

Not editing and clipping, but more to because I think that sort of always sounds a bit awkward. It. I'm not here for the ad. I'm here for the [00:45:00] content, which has a natural ad in it. And my natural ad is we're talking about there's three rounds. We talked about round one question as its own separate content, and then we had an ad for go watch the webinar 'cause native.

So a little bit more like that and a little bit more intricate. I could probably, if I sat and thought about it, think of better ways to do that or it's figuring out what are. Not necessarily the ad, but what's the next piece, if you like that enough to wanna see some more rather than another episode what could that be and how, so for that instance, how would, what could I have thought of better in the Family Feud webinar, which could have played into a podcast series in a different way.

It's just easy to take the three rounds and make three episodes, no brainer. But how else could I do that or we did? Dancing With the Stars. We made that into emailing with the Stars. So we did basically the final, there's two sales reps. They write an email each, and then they get judged by the panel.

Same as the dancing show. Pretty easy to just review the emails that the reps wrote. Is that a brilliant podcast? [00:46:00] Not really. It was fine. It was smart to do it, and it got us a little bit of promo for the for the webinar. But how else can I do it? We don't wanna just use the podcast as an ad 'cause no one wants listen to the ad.

So what's the point? But how more naturally, how more cleverly, what else could I make without going out on the limb to make loads more work, to pull it together. I'm trying to describe, I hate talking about YouTubers 'cause no one knows who they are. But Mr. Beast, probably a lot of people know who he is.

He did a video a couple weeks ago and it's something stupid the one Euro, $1 yacht versus the 1 billion yacht. And through the video they go through 10 different yachts of all varying expenses. And he's got a chocolate brand, chocolate bar, it's called Feast Balls. So in the first one, he gives it to the owner to pay for the art.

'cause it's the same value. It's one $1 to buy it. So that's a native ad for the chocolate bar. And you didn't feel weird about it. It wasn't like, And guess what? You can get 10% from athletic greens [00:47:00] because of what the hell that doesn't fit, so no shade. No shade to athletic greens, no shade to them.

But, and then, they go to the half a billion yacht and every bed, every bedroom on it has the chocolate bar, because that's what happens in that chain of of cruise liner. Again, you're seeing his chocolate bar and it makes sense, and they remark about it. They go, what? I didn't know that we sold it into this cruise liner.

What the hell? It is native. So I'm thinking of how in my content can I take that ad, put it in a couple places where it doesn't feel weird.

Casey Cheshire: Yeah, I to, I totally get that, man. My, my man, my son, he's yeah, let me try all the feast balls. He's in on it, the idea. So I see where your brain's going, man, this is this is a future episode. We'll have to come back on this thing and talk at this wizard level because I totally, my brain is expanding.

Now, the idea of not just repurposing, But also almost like that content pillar. If we're gonna have a theme, how can we best efficiently and [00:48:00] effectively create maybe one thing or several things that all I. Play off of each other more naturally, just very naturally. So you just, you find yourself going into one of those YouTube rabbit holes where you start YouTube and three hours later what just happened with my life?

Because you just organically just went down this path and subscribed to three people you never even thought of or watched The super yacht versus the 1 billion super yacht, which I'm looking at right now, which is covered in gold.

Ollie Whitfield: Exactly. Yeah. And it's not in real life, but hey it's YouTube.

Casey Cheshire: It's YouTube and it's podcasting. Dude, you are the man.

I have enjoyed this tremendously. Tell me, where can people connect with you if they also heard this episode and they're like, this guy's the man. Where do they go?

Ollie Whitfield: If they are, I feel sorry for you, but all good. All good. Yeah. This has been good fun. Thanks very much for having me. I'm gonna say the L words. I apologize. I find it so annoying when everybody says this. I say, guys, where can people connect with you? Where can I find you? And they always go, yeah, LinkedIn.

And you're like, [00:49:00] oh God. Gimme something else, please.

Casey Cheshire: that question. Do you ask that at the end? You have to,

Ollie Whitfield: that's what I normally do. And I normally say, where can people find you and ask you a question? So sometimes they say their email and that's it.

Casey Cheshire: Yeah, every now and then people say that. Yeah. And I just think such disrespect saying the email, because if this was Rogan, you'd get like 30,000 emails that were like snarky,

Ollie Whitfield: Yeah.

You just get pared to bits. So yeah, I've. Yeah it's a funny one, but yeah to use the classic L word. Yeah I spend most of my time on LinkedIn. I do Twitter. It's mostly just me looking at football stuff, to be honest. And that's kind of it. And then the podcast, of course, as any podcasters might know, on all of the usual places where you could look, wherever you consume.

And it's a zero to $5 million podcast or all numericals, not words. And yeah, we'd appreciate if you swing by. It's only 15, 20 minutes, so I promise you won't lose three hours of your day. But it's good fun. We like to ask, like if I was asking you, it would be, so how did you start this podcast?[00:50:00]

When did you really mess it up? Why have you done it this way? Key hires, mistakes, change in strategy. What are you gonna do with it in the future? That type of thing. But it's about businesses.

Casey Cheshire: Dude, I love those. Those are great questions. Now we have to start the show over and just ask you those questions.

Ollie Whitfield: Let's do it.

Casey Cheshire: zero to 5 million. Fantastic. Dude, Ollie, thank you so much for coming on here. This has been fun. Clearly we need to get a pint next time we're in the same zip code. Area code, whatever. This is super fun, man.

I definitely wanna have you come back and we'll talk more content in the future and repurposing and that kind of thing. But a big thank you from

Ollie Whitfield: My pleasure, dude. Thanks very much.

Casey Cheshire: Hell yeah. And for those listening, if you learn something and I freaking know you did, because I literally have two pages of notes front and back. Then share this episode with one person, three people, 9,000 people, I don't know, whatever.

But put your thoughts down too. Don't just, click a share button, but write. What, especially on LinkedIn, right? This is what I got outta this tag. Somebody that needs to hear it. Tag a shitty podcast that needs to get love or [00:51:00] tag a good one that needs to get even more love and and put these lessons out there.

Check out Ollie's pod and once again, thank you dude. You're the man. This has been another crazy episode of Creating the Greatest Show. We will see you all next time.

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