Welcome to another episode of PodJunction Podcast, in today’s episode, we present our full conversation with veteran of the advertising industry, Skip Wilson. In conversation with host Sadaf Beynon Skip shares his journey from starting as a copywriter at 16 to building the iHeart podcast network and eventually leading Draft Media Partners. Skip provides many valuable insights, discussing how to launch and scale you podcast. 

Main Takeaways:

1. Consistency is Crucial: Maintaining a regular posting schedule is essential for building and retaining an audience. Even if your recording times vary, ensure that new episodes are consistently available to listeners. This consistency helps in establishing reliability and trust with your audience.
2. Leverage Guests for Promotion: Having high-quality guests on your podcast can significantly boost your reach. Skip emphasises that guests often promote their appearance on your show to their followers, driving organic growth and attracting new listeners. It is good strategy to select guests who are engaging and have a relevant following to maximise this benefit.
3. Focus on Storytelling and Character Consistency: Good storytelling is a vital component of a successful podcast. Whether your podcast is conversational or more structured, maintaining consistent themes and character roles helps in creating a compelling and engaging experience for listeners. This consistency in character and content keeps the audience invested in your podcast.

If you enjoy this episode of Podjunction and want to dive deeper into the world of podcasting, don't miss out on our future episodes! Subscribe now on your favourite podcast platform and start transforming your business with the power of podcasting today!

Skip Wilson | How to Grow a Successful Podcast

Sadaf Beynon: Welcome to Pod Junction Podcast, a show for podcasters who want to use their podcast to grow their business. I'm your host, Sadaf Beynon, and today I'm joined by Skip Wilson, a standout in the advertising world and host of the advertising podcast. With a career spanning decades, skip has been at the forefront of digital media innovation.

And now leads Draft Media partners. Welcome to the show, skip. It's a pleasure to have you with us.

Skip Wilson: Yeah, thank you. It's an honor to be here.

Sadaf Beynon: Oh, thanks so much. Skip, you've had a remarkable journey in advertising, starting as a copywriter at 16. What inspired you to start the advertising podcast?

So, I mean, the main reason I started the podcast on, you know, being fully transparent was, um, to, because for marketing purposes, for purely self serving purposes, now that said we wanted to make a show that was actually beneficial and actually offered some, um, some insights and benefits to, to the listener, of course.

And, but the, the main reason was because that was our, I, I came from. You know, before, before draft, I was the vice president of digital media at iHeartMedia, and we built out one of the main things we built out, um, in my division was the iHeart podcast network. And just seeing the power of podcasting, both Large podcasts as well as small podcasts and the power and impact it can have on businesses.

Sadaf Beynon: So how does your podcast then compliment the work that you're doing at Draft Media?

Skip Wilson: Yeah. So one of the rules I have for starting a podcast venture is Um, because we, we're actually about to launch another one too, but one of my main rules is if there's zero listeners or a million listeners, there needs to be, it needs to be structured in a way to where there's benefit to the company, because that's something that a lot of folks don't realize is everyone of course thinks, Oh, you know, you know, if I start a podcast, then I need, you know, 10, 000 downloads a month or something like that in order to make it worth it.

You really don't need any, you don't need any listeners at all. Um, one of the, one of the main things that I look at is one, creating a reservoir of knowledge so that if we bring someone into our ecosystem, we can send them a link to things so that they can listen and become a part of our culture and understand the reason why we structure things the way we do and those types of things.

And then also with the advertising podcast in particular, the, that was really a lead generation like play, like our main goal with that podcast was to invite people onto the podcast that we otherwise wouldn't be able to have conversations with.

Skip Wilson: I mean, it was, it's just a lot easier to say, you know, the, the way our business is structured, the way Draft Media Partners is structured is a little different than a traditional like ad agency. We mostly work behind the scenes of other ad agencies and marketers and media companies.

And so like it's a fractional CMO. We're their team that they outsource things to if it's a, if it's a midsize ad agency, then usually there's, you know, they may do like AdWords themselves, but they anything else, they're going to want to sub it out to someone else. And then that's where we come in. Um, so those folks are all very busy people that don't normally have, you know, like a lot of time to just sit down and chit chat.

Sadaf Beynon: Yeah, totally. Okay. So do you have any, do you have any stories of people that you've had on the show that have then turned out to be great clients?

Skip Wilson: Yeah, you know, we, we do it in a very soft sell way. We, we're very much a, if you build it from a business standpoint, now this isn't necessarily a podcast, uh, so much question, but if your business is structured in my way, in my opinion, sort of the right way, and then you have a very compelling product that really almost sort of sells itself.

So I would say actually, I mean, pretty much not a hundred percent of the time, but almost a hundred percent of the time. When we sort of in natural conversation, we'll go through and I can mention something like, you know, our simulator tool that we built or the platform that we built or something like that.

That's like the first question. It's like, Oh, you know, draft meeting partners, what do you guys do? And so that's just an instant invitation for your elevator pitch. And so as long as you have that message crafted to that, uh, to that individual or audience, you're So that's, that can be really compelling.

Skip Wilson: So with, so we, like I mentioned, we're about to start another podcast, um, called the Advertising Singularity shameless plug, although it doesn't exist yet, but, um, called the Advertising Singularity where that, that show is really all about talking about, About like the future of advertising technology and the things that are being built right now, because, you know, there was over a thousand marketing SaaS.

Products that came to market in just the past 30 days. So it's a kind of, uh, I feel like the phrase is overused all the time that, you know, we're in a time of change or, you know, or those types of things, or there's a, we're in an unprecedented time, but we truly are in the marketing world. I mean, there's so many markets just popping up constantly.

So for that one, there's really two monetization strategies. One is it creates what I call a like a binge bank for people that are in our pipeline. So one of the, you know, in business, especially service businesses or business to business businesses, Companies only do business with people that they know, like, and trust.

And they understand what you mean. You know, like we have some internal phrases like, you know, only no, no failure, only feedback. And, um, the, you know, if I mentioned things like our simulator tool and those types of things. Yeah. That means nothing unless someone's already in our world, right? And a podcast is a nice way to bring them into our world without us having to actually spend hours with them, right?

We spent hours creating content once and then they're getting to, to enjoy it. Um, but with that one too, because there is no guests, listeners will. It's another one where if there's only 10 or 15 listeners, but those 10 or 15 listeners are in our pipeline, there's benefit to us. But that is one where eventually we would want to scale it up to try to tell the story of our company and things more.

So there would be a little bit more of a monetization strategy.

Skip Wilson: That's a great question.

Cause actually, no, it should. And I mean, or, you know, in theory it should, right. Um, but in, but because of the way we wanted that, we actually structured it to where it has benefit for our guests. Um, because remember like with that podcast, like it's all about whoever our guest is. And so what we wanted to do was create a podcast that has incredible value to whoever that guest is.

So they might listen to it, but a lot of it is like advertising basics and those types of things that they probably would not get a ton out of unless they're new to the advertising world. Um, but a small business owner would get incredible value. And the small business owner is the target audience for a small to mid sized agency or a fractional CMO.

So we created something that is a benefit to our target audience, which is the guest. Not necessarily the target audience of the podcast.

Sadaf Beynon: Right. Gotcha. Okay. So, um,

Skip Wilson: When you have, um, when you have high quality guests on that have a bit of a following themselves, that itself is a sort of marketing strategy because most, you know, most folks who are a part of a podcast instantly want to tell the world, right?

Like you want to say, Hey, listen to this, check this out. They're going to want to promote that themselves. And so what's nice about that is that you don't have to, like, we don't have to do a lot of promotion to get, you know. Several hundred downloads just organically, right? And then a certain percentage of those folks will, that they're promoting to, will like the podcast and will begin to follow it themselves.

You know, a few hundred bucks on Spotify or a few hundred bucks on YouTube would go, can go a long way. For a

Sadaf Beynon: podcast. Yeah. That's interesting. Cause you're able to then leverage your expertise. Aren't you?

Skip Wilson: Yeah. Right. Exactly. And cause you can target, I mean, even, uh, even the self serve side. I mean, even, you know, anybody listening to this can also just do this, can do this themselves as well.

And you know, it's not like it takes thousands of dollars to see a return. Obviously, the more you put into it, the more you get out of it, the quicker you get out of it, all of those things. But, um, you know, it can truly work for any budget.

The other thing that we've done to, to help promote that podcast is, um, the apply to be a guest. That's the only ad that we've ever put towards that budget and it's targeted at specific companies. It's targeted, it's a, you know, usually we'll use something like LinkedIn. Um, as a matter of fact, I think we might've only used LinkedIn, but we could have used LinkedIn and programmatic display and, and a few other tactics.

Targeted specific companies saying apply to be a guest. So

Sadaf Beynon: how did you do that? Sorry, can you like spell that out a bit more? What was the process for that?

So, um, if it's business owners, for example. Then, okay, but there's, I don't know of any B2B company that works with all business owners. So, small to mid sized, you know, businesses, uh, or, you know, is it company size that's the difference? Is it what industry they're in that's the difference? And you want to try to whittle it down.

Like for us, it was a very specific niche. So we actually did job title targeting, um, on LinkedIn. Um, because we're looking for people with specific job titles, but, um, depending on, you know, so you want to get as specific on who you're trying to reach as possible, then you figure out where are those folks, which for us is LinkedIn, um, for, you know, for, you know, someone listening.

and business owners aren't trying to get a promotion.

Mm-Hmm. .

Skip Wilson: So, um, the, so that's not the platform I would choose.

Mm-Hmm. .

Skip Wilson: And so, um, where, who's your audience? You figure out where are they?

Yeah.

Skip Wilson: And then you figure out, okay, what am I, what's the one thing I'm trying to get them to do? Now you can't, in other words, you can't run an ad saying, listen to my podcast and.

And then it, then you wanna think about the environment of where they are when they're trying to do the thing. So that's why I mentioned if you're trying to get listeners, YouTube is great. Spotify is great, because if I'm listening to podcasts on Spotify, I'm a podcast listener already. So for me to switch from one path of cast to another,

mm-hmm ,

Skip Wilson: incredibly easy.

YouTube, um, is I think already the second largest podcast network or podcast platform and it's going to continue to grow. Um, and so if I'm on YouTube, it's very simple for me to, instead of whatever, instead of watching a cat play piano, I can switch over and watch, you know, and listen to this podcast about this topic that I'm interested in.

Sadaf Beynon: Yeah, that's cool. So

Skip Wilson: So you should always, so SEO, um, there's a difference between with SEO and SEM. SEO is organic growth. Um, the analogy I always use is diet and exercise.

Okay.

Skip Wilson: SEO is diet and exercise. It takes. Okay. A long time to get results, but then once you get those results, as long as you keep up the good habits, it stays. And even if you stop the good habits for a little bit, you know, you can go on vacation without gaining all your weight back. Right. Um, you can, and those types of things, but if you're gone, but if you.

So that's SEO. SEM is all about paid ads, and it's more like a light switch. It's more like the, the stuff that Eddie Murphy drinks in The Nutty Professor. I don't know if you remember that movie or saw that movie. It's more like that. You can instantly become skinny, but then the minute it stops, you're instantly not skinny anymore, right?

And that's, that's more what paid ads are. And the advantage, of course, is that, you know, you could have a million listeners tomorrow. It just might cost you several thousand dollars to make that happen. Um, and so for some folks, you know, it just depends on whether, what your time horizon is like, if, and, and SEO should always be a part of your strategy because it's free and it's really just about doing good business.

then

Skip Wilson: that means you probably have just done like a poor execution job. If your SEM, uh, SEM on the other hand, isn't the best choice for everyone, you know, if, if a podcast is like your side hustle or totally tangential to your business or something you're kind of just doing as a hobby.

Then it's not worth the investment unless you've just got, I mean, I mean, there's some folks that'll drop like Yeah, unless you've got yacht money, right? Yeah. Unless you can drop like 30 grand in ads and just don't care.

Mm-Hmm. . Um,

Skip Wilson: but, but with that said too, it's not like it takes a ton of money. It you can a few hundred bucks a month or a hundred bucks or so a month if you're doing it yourself.

Sadaf Beynon: Yeah.

Skip Wilson: Can be beneficial.

Skip Wilson: So I think it was Steven Spielberg that was asked, like, if he had advice for someone who wanted to be a director.

Okay.

Skip Wilson: And, um, you know, when they were younger and starting out and his main advice was watch movies. You know, just be an avid movie watcher. That's sort of step one. And I think the same thing is true with podcasts. If you're somebody who doesn't know what a podcast is, you know, like sometimes we'll get, um, the, I have a good friend of ours actually, um, just, just down the street from us, um, is, uh, that's what they do is they build like content strategies for folks.

And, um, one of the things he jokes about all the time is there'll be some CEO or something in there that has never listened to a podcast. Has no interest in podcasts, but is just being told they should have a podcast. That podcast is doomed to fail from the start, right? Because that person's not going to know what makes a good one.

Um, you know, if you're a marketer, then you should be listening to anything and everything that has Gary Vee on it or something like that. Like you should just be like absorbing all of that stuff because it'll do a couple of different things. One, it'll, it'll highlight best practices, you know, like there's a reason that whether it's a small podcast or a massive podcast.

It always ends with please leave a comment, like, subscribe, and those types of things. So it'll allude to best practices. You'll also pick up on things that you like and things you don't like. You'll be like, Ooh, that's cool. I like how they had specific segments and I like that. I want to do that. Or I like how that's conversational.

The only ones that exist are ones that are made by ad technologies. So those, those of course all had a vested interest. So it can also help you figure out where there's a hole in the market. Yeah.

Sadaf Beynon: Yeah. Yeah. That's cool. No, that's great advice. I, I particularly like what you said about being an avid consumer of podcasts in order to learn it better.

I think that's, that is just so true. Understanding how it's done and like, and kind of taking ownership as well, isn't it? Of, of your own podcast when you're doing it, because you can see how other people are doing it. What's the right fit for you?

Skip Wilson: Exactly. Yeah, because there really is no wrong or right way.

Yeah. It's more, you Which is, you should try to pick the one that's more appropriate to you, because if you don't have time to do a well edited and produced podcast. Then you're only going to do it for probably five or six weeks before you start getting frustrated with it and just stop

Sadaf Beynon: if

Skip Wilson: you're, and then, uh, so in that case, do conversational.

Um, but if you're somebody who is not very verbose or doesn't like talking very much, then maybe lean more towards edited and produced.

Sadaf Beynon: Yeah. How do you do yours?

Skip Wilson: Um, the, the advertising podcast is very, because we are talking to marketing people and for the most part, marketing people are definitely more on the verbose side.

I could see eventually doing a very well produced, polished podcast because I just enjoy doing it.

Um,

Skip Wilson: but right now I'm struggling to get through my inbox each day. So right now is not the time for that, but eventually I can see doing that.

Sadaf Beynon: Yeah. I guess holding those two things together is, um, it's quite the task.

Skip Wilson: Exactly.

Sadaf Beynon: Yeah.

I would always, consistency I think is more important than what you choose.

Sadaf Beynon: Yeah. Yeah. That's great. That's really true. How do you, um, select and invite guests onto your show? Cause I know you talk to marketers, but how do you decide on which ones you want on your show?

Skip Wilson: We, we really try to look for folks that have had, like if they have somewhat of a presence already.

Okay.

And so that's the other thing. Um, and then of course the third benefit is. More of the selfish benefit, which is that then when they promote it out to their following, it's got a little bit more of a, um, it's just reaching more people. So that's, that's how we select it. I will say that I don't think there's, it's another one of those things, right?

I don't think there's a right or wrong. Answer in general, but the advice I would give is think, who does my audience, who does the audience of the podcast want to listen to? So, you know, for the advertising podcast, it is small business owners.

Who

Skip Wilson: do they want to listen to? They want to listen to experts in marketing that know how to, how small businesses should market.

Like that's probably going to be somebody who has more advice. Yeah. Yeah.

Sadaf Beynon: Yeah. Um, let's, uh, question about your audience. How do you, um, get feedback from them? How do you know what they like, what they don't like? What they want more of, what they don't like for you to be talking about or doing.

Skip Wilson: So there are, there's a number of reputation tools and, uh, listening tools.

So one way to do it. Um, and of course the free version of it is just to constantly be looking at those things, but constantly be inviting feedback and then reading and paying attention to the feedback. People will tell you what they like and don't like also early on, you know, when you have say less than a hundred listeners or so, you're probably not going to get many comments, likes and those types of things.

So instead. You're just paying attention to the date, the data, like what's the retention rate like, what it, you know, are, am I losing people five minutes in, if so, I either need to make it a lot shorter or make it a lot better. Right. And so just paying attention to data, both the qualitative and the quantitative feedback that you get.

Skip Wilson: I mean, definitely in my, definitely in my iHeart days, um, the draft one. You know, the draft podcast just hasn't, that has essentially like not enough scale to really get good feedback other than the qualitative stuff.

Um, and again, that's by this, that's sort of not by design, but we didn't design it to do otherwise. So

of

Skip Wilson: course it's not going to just grow big on its own. Um, but definitely in the iHeartDays, I mean, that's, that's a huge part of what we're constantly doing. What we were constantly doing was trying to figure out.

If you're not getting any listens at all. Then you're probably picking poor topics or you're doing something bad with titling. Um, maybe on YouTube, it's something like thumbnail or something like that, but you know, it's probably a titling and topic issue. If you're getting starts, but not a lot of retention, um, or it's just not, or it's just not growing, um, then it may be more of a quality issue.

So then you need to look at, okay, what can I do to take this show to the next level? But one of the biggest mistakes I see is. Someone will have a podcast with small, with low listeners and not really growing, not really doing anything. And then they'll just keep making the content better. But the reality is, is that you could have the most well produced, greatest podcast in the world.

Sadaf Beynon: So is there a way to appear? Um, higher up on Spotify.

Skip Wilson: There's the, yeah, there's, I dunno, there's, I dunno know

Sadaf Beynon: how to word that question. Sorry.

Skip Wilson: Yeah, no, that's, that's great. Yeah, no, the, there's, I mean yes is the short answer. There's two ways. I mean, you either, you either pay to get there through ads or you earn your spot there through, through, through organic growth.

Okay. Um, and that, and that's, and, and that's really, that's how to do it. Hmm. Um, so I would have, I would be intentional about if it, if it's the organic. Growth, um, strategy, be intentional about, you know, which again, like I said, everyone should have an organic growth strategy because why not be intentional about your topics, be intentional about guests.

If it's paid media plan, then, you know, it's just, it's, it's, it's. It's the same principles, but I would almost pick like, if you're just looking for pure listeners, one of the greatest things I would do, especially if you have a small budget, is figure out like which of my episodes add the most organic listens, stay over the past 30 days or whatever.

Um, unless it's an evergreen show, in which case any, any timeframe is fine. Um, you just don't want to be talking about like Christmas and like, you know, and then it's a June podcast or something, but, um, pick which, which show had the best listens organically and then promote that one. If you're not sure which one to pick, that's the one that your audience is saying, we like this one the best.

Sadaf Beynon: Yeah.

And. Yeah, there doesn't really seem to be a correlation between how I feel on that and what the end result is. There are plenty of times where I've been like, well, I messed that one up and then we'll land like a huge piece of business or it'll be great or I'll get a lot of feedback. And there's plenty of times where I'm like, Hey, that was fantastic, that was great.

And then I just net, it's just crickets and nothing ever happens. Yeah, exactly. And so, so yeah, there's, it, how we feel doesn't matter because we're, we have a very different, you know, experience than anyone listening would. And so I think it's almost impossible to guess how, like for yourself, which one's the best one.

Skip Wilson: I mean, the biggest challenge is, uh, you know, you, you, I would, especially for someone starting out, the biggest, the biggest challenge is overcoming that like sense of that you're just doing, creating content that's going out into the void. That's this big hurdle. I'd say that everyone's going to have to overcome at some point, but just remember that everyone did that, right?

Like everyone had to start out with that point of you're creating content. It's just sort of dying on the vine, and that's okay, because that doesn't mean that that's always going to be that way, and those types of things. I would say that's the biggest, the biggest challenge, um, for the advertising podcast in particular, we, we ran into a, uh, a scalability issue.

I would say that was the biggest challenge. Um, and so what stinks about that, when you have to take a long break like that is you're essentially starting, starting over again. So I would only do those things if you have no other choice. Keeping something going, going from weekly to biweekly, you know, is better than stopping entirely.

Yeah.

Sadaf Beynon: So what did you do? You stopped, did you say?

Skip Wilson: We did. Um, but the, but you know, now, but that's, uh, that was only because, uh, only because the last thing we needed was more folks. So we need, if you're struggling with orders, uh, then. You need is more orders, .

Yeah.

We've up all those, all those things. But yeah, that's, that's something to think about, especially if you, if it's a business focused podcast or a podcast that you're doing for business reasons, is you just want to almost sort of have the seasonality in mind. Um, for example, if I was an accountant, let's say that we were an accountant.

So be intentional about where it falls into, into, into your, into your podcast. Realm as well, which we did not do a good job of. And that's, and that's why that was our biggest challenge.

Sadaf Beynon: Yeah. Well I guess there's learning from it, right? And that's what's the best thing. Exactly. That comes out challenges.

So, exactly. Um, yeah. So how do you then manage your time and maintain that balance now with draft media and with the podcast?

Skip Wilson: I mean, we've hired, we've, we've hired folks. I mean, that's, you know, that's the, the main way, um, you know, delegation and, uh, and scaling things up. I mean, that's, that's the, that's one way to solve the problem.

Hmm.

Skip Wilson: That's, that's the only way sort of to do it. And, and if that's the case, if you are, you know, like, you know, for us, uh, where we're. Each day it's so fo like changes so wildly based on how many appointments we have that day. Yeah. You know, like my calendar today looks incredibly different than my calendar tomorrow there would be no way I could do a live at Thursday at 2:00 PM podcast, right?

Because I would have no clue whether Tuesday at 2:00 PM on Thursday works. So that means that I either need to pay for a service that I can prerecord and make it seem live. Or, um, not do, just intentionally not do a live one.

Skip Wilson: Exactly, because you want it to go out to the public. You can record it whenever. Nobody really cares about that. Um, but if you, when it goes out to the public, That's what you need to be consistent with constantly. And so that's why I would not choose a live format podcast. So I don't really like the ones that seem live, but aren't, because I think that's disingenuous.

Um, and, uh, although no judgment on anyone that does do that, cause that's, that's fine too. Um, but the, um, but you know, I just, I just don't like that format because I can't say have consistency on the recording side. But there's really no excuse not to have consistency on the posting side. That's just like making, you know, at some point during your week, make sure that you've got something scheduled for next week.

Skip Wilson: The main thing that I think is. Essential is being a good storyteller, being able to talk in things like, uh, you know, consistent themes that even if you have a purely conversational type podcast, you want it to always have a consistent theme. You want each person to sort of play a role or character so that they have, you know, what's called parasocial consistency.

Usually that comes in the form of couching it in a compelling story. So if it's just one person on the podcast. You want to make sure it's got an introduction, three points, and conclusion. If it's, um, just a, um, you know, if it's the conversational one, then like I said, you want to make sure everybody's playing their roles and that it's all got consistent themes so internal consistency as well as consistency with. Yeah.

Sadaf Beynon: I'm going to ask you, and I'm sorry, again, I didn't prep you for this, so I hope you don't mind.

Yeah. All right. So Skip, this is something I ask, um, I like to ask my guests and that is that if, can I see you in 60 seconds tell me why you think podcasts are great for, um, or are a great tool rather for growing your business?

It's true. And podcast is just a current way to get someone to spend a lot of time with your company, whether it's a decision maker or someone in your company to get to know and like the brand. There's just not a better way to drive brand affinity than telling stories. And podcast is just the current way of doing

Sadaf Beynon: that.

Fantastic. Thank you. That was great. Thank you. Well, Skip, it's clear that your podcast has become a cornerstone of your business strategy. And, um, your journey is full of valuable lessons for anyone looking to leverage podcasting for business growth. So thank you so much for sharing your experiences. And insights with us today and for bringing such value to podjunction.

Whether you listen while on the go or in a quiet moment, thank you for letting us know. Remember, every episode is a chance to gain insights and to transform your business with podcasting. So keep on tuning in, keep on learning, and until next time, happy podcasting.