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My Weekly Marketing
Join conversations about marketing, business, and life-in-between with marketing strategist Janice Hostager and a variety of world-class entrepreneurs! We will fill you with step-by-step training, marketing strategy, and life experiences from where life and business intersect. We'd love to have you join the fun!
My Weekly Marketing
How to Run Ads Without Burning Money with Skip Wilson
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In this episode, I sit down with Skip Wilson of Draft Advertising to talk about why clicks don’t always turn into customers. We break ads down to what actually matters: a specific offer for a specific audience that leads to a specific action. Instead of starting with platforms or trendy tactics, we focus on choosing the action first and building everything around that.
We also explore why vague offers like “free consultations” often fall flat and how smaller, clearer entry points can lift conversions. Skip shares practical insight on when Google Search makes sense, when Meta performs better, and how to use AI tools thoughtfully without losing control of your message. If you want your ads to feel more intentional and measurable, this conversation will help you rethink your approach.
I'm Janice Hostager. After three decades in the marketing business and many years of being an entrepreneur, I've learned a thing or two about marketing. Join me as we talk about marketing, small business, and life in between. Welcome to My Weekly Marketing. Have you ever run ads and thought, okay, well people are clicking, but nothing's happening. Or maybe you've been thinking about running ads, but something in your gut says, I'm not ready and this all seems complicated. Well, today we're getting very practical. I'm talking with Skip Wilson from Draft Advertising, and we're breaking down what business should actually prepare on paper before running ads, how to avoid wasting money on ads that were doomed from the start, and how to turn advertising into something measurable, intentional, and way less stressful than it sometimes is. If ads have ever felt confusing, expensive, or disappointing, well, this episode will save you money and frustration, my friend. So let's get into it. Hey Skip, welcome to My Weekly Marketing.
Skip WilsonThank you. Thank you for having me.
Janice HostagerBefore we get like tactical today, why do you think that people really hesitate with spending m money on ads? I mean, what's the big misconception that business owners have about running paid ads?
Skip WilsonYeah, I think they think that they must have some huge budget, or because they think of advertising as like a black box that they're going to put money in and never see anything out of. Or they go in guns blazing and they and those are the ones that don't see anything out of out of it. So they go in full bore and without direction. So I'd say usually folks fall in one one category or the other.
Janice HostagerLike either too much or not enough, basically.
Skip WilsonRight, exactly. They think either advertising is the solution to everything in their business, which it's usually not, or they think it's an absolute evil that's just sort of an annoying necessity, which it's also not. So yeah, it's yeah, they either undervalue it or overvalue it.
Janice HostagerSo in your experience, what usually like breaks first when ads don't work? So is it the platform or the creative or the strategy?
Message–Audience Mismatch
Skip WilsonUsually so it's it's most important that the creative and the audience match. Like if you think I always think of advertising in terms of a specific message to a specific audience to get them to do something specific. And so one of those two pieces is off. Either you're talking to the wrong people or you're saying the wrong thing. Nine times out of ten, you're just you're saying the you're it's usually the message. Yeah, exactly. Or it's not you know actually designed to get them to take the proper action. In other words, it's you know, we we'll have sometimes uh an advertiser that's like, you know, all we're getting is people that we can't finance, for example. And then I look at their message and it's all about how they'll approve anyone and there's no down payments and things. And I'm like, well, your message is designed for the folks that you can't find. Like it, you know, it's so it's it's some sort of audience message mismatch.
Janice HostagerRight, right. So it sounds like maybe strategy is kind of missing a little bit too. Like if they're if they're jumping into with the wrong message. I don't know. I always think it starts with strategy, but absolutely.
Skip WilsonYeah. I mean, it really if because you and you don't know what to say until you think through what am I trying to get them to do and who am I talking to.
Janice HostagerRight, right. Yeah. But that can all be complex. I mean, it's hard to put yourself in the shoes of your ideal customer sometimes. Really hear things the way that they hear them.
Skip WilsonYeah. And for business owners that are far removed, you know, most I'd say nine times out of ten, we come from the world of our customers for the most part. And so a lot for a lot of industries, you do know how to speak your target customer's language. But if you are in a situation where you're a business owner that's in a different space than the people that you're you know solving problems for, then you shouldn't be really nothing should go live or you shouldn't be doing any advertising without someone in that group taking a look at it. I actually know somebody who designed female athletic wear, but he's an older guy. If you've got a young female athletic wear company and you're an older guy, you need someone, you know, you've nothing should go live from your perspective. It should always be reviewed from someone in your target audience perspective.
Janice HostagerOh, so
Founder Backgrounds And Perspective Gaps
Janice Hostagertrue. So what's your story? Was there a point in your career where you realized that ads were something that you really wanted to focus on?
Skip WilsonYeah, I definitely, you know, I think everyone sort of back like dummies their way into it. The ads industry, you know, I don't know that anyone wakes up and goes, you know, you know what I really love is ads. For for me, it was I wanted to be a writer. And the only writing jobs around where I lived were at ad agencies, or at least that I could get. And I was 16 years old. And so I started doing some freelance copywriting work for a few different ad agencies. And then that was right as WordPress was becoming a thing and everyone was getting a website. And so they asked, can you do web design? And because I needed money, I said sure. And so that's sort of how I got got into the industry, and then it just, you know, kept on going from there.
Janice HostagerYeah, yeah. I think you're right. Although I would say that I started in advertising as well, and I was like super hyped. I wanted to be like, you know Ogilvy, you know, somebody. So I have met a lot of people that, you know, even on I was on the art direction side. So I did meet a lot of people though that kind of felt like, well, you know, I was gonna be an artist, but yeah, I'm doing this instead. But I love, I think, I think the thing that fascinated me about advertising is that it's kind of where creativity meets psychology, meets strategy. And that like the three kind of come together and produce results that are tractable and tangible.
Skip WilsonSo I always wanted to, for me, I was always like, I'm a journalist. I'm just doing this right now, but I'm really a journalist. And then I actually got I worked as a journalist for about six months right after college. And yeah, it was one of my first jobs was I was actually paid to write about traveling to Argentina by and it was a sponsored piece from a company. And I'm like, oh well, this is just an ad. And so that's that was when it finally started to click on me, you know, click with me that wait, advertising actually is, you know, this beautiful thing that I kind of thought, you know, you really can change people's lives, you can make companies better, you can change, you know, it I I ended up falling in love with the industry, but it was for I would say the first, I don't know, even after that point, honestly, for the first decade of my career, I would always be like, yeah, I'm just doing this right now.
Janice HostagerAnd it's like so what would you say would be like the minimum amount of clarity that somebody needs around their offer before starting to run an ad? So let's say that you know, I have a a new thing that I'm selling, let's say I'm uh an accountant and I'm trying to get some clients for tax services. Uh how much clarity would they need to have figured out before they they put pen to paper, so to speak?
Skip WilsonWhen you think of advertising, you're thinking about people that are cold, meaning that they don't know like who you are and and they may not even know like what you do now in accounting, they they're well aware with what accounting is. But the first step is to sort of put yourself in the mind of your customer and think, where's that first touch point? Like for an accountant, probably that first touch point for if they're trying to get, let's say they're trying to get like B2B accounts, like they're trying to like they're a B2B accountant or a business accountant. Probably that first touch point is gonna be like tax preparation. You know, that that's gonna that's the that's the thing that's things like bookkeeping, payroll, and all those things, those affect most businesses. But the thing that affects uh everybody is taxes. So, you know, for the one that so all right, well then tax prep is probably the foot in the door. That's the thing that has the most broad appeal. And the and then you think, all right, well, what's somebody who's what's that first pain point? And you know, something like uh, you know, I are your just QuickBooks, you know, QuickBooks for a young entrepreneur can be can be very overwhelming. You know, it's still I'm not entirely sure. I think I'm using it like like 10% of what it can do, which is all I want. I don't want to know more about QuickBooks. I'm done at 10%. But you know, that's so doing something like a, you know, mm sync your, you know, make sure your QuickBooks is properly, you know, synced up. That type of offer is something that you know is going to appeal to most businesses, you know, virtually every business, and it's a very easy touch point. Doing something like that compared to running just a free consultation or free tax prep or some that type of conversation, nobody woke up this morning going, oh, I really want accounting. There is somebody who woke up this morning going, man, I really wish I could just pull a profit and loss report in QuickBooks and that'd be accurate. You know, so you've got to sort of think through like what's the thing that someone actually wants right now that I could offer that's a very low ask of them. You know, it taking a 30-minute sit-down. The reason I'm harping so much on free consultation is because free consultation is like one of my it doesn't convert very well. It usually gets really bad leads. The free consultation I'm uh should almost never be the
Defining The First Touch Point
Skip Wilsoncall to action, because that's a big ask. Like it's hard to get, you know, 30 minutes to an hour of someone's time for, especially if you're business to business. There's nothing more valuable to a business owner than an hour of their time. And so that's actually a huge ask. Whereas having them fill out a form and then you go, yep, it's correct, it's connected. Now that I've helped you with that, let's talk more about your your other needs. That's much that's much easier. So first step is to think, what's that first touch point? Is it a phone call? Is it, you know, what what is that first touch point?
Janice HostagerGotcha. Gotcha. So uh, you know, is that kind of the question that you think everybody should ask before even starting to add? Would be just like, or is there another question that they should ask? Not that I'm leading you here, but like maybe like go ahead.
Skip WilsonYeah, no, your your first your the first thing you should know is like what your actual offer is. Like what's the thing you're trying to get more people to do? You know, the that specific message to a specific audience to get them to do something specific. You need to know what that something specific is before those before knowing who you're talking to and what to say. And so, yeah, your your first step really needs to be knowing what do I want more of? If you're a roofing company, do you want more phone calls? Do you want more form fills? Do you want, you know, do you want more of those things? Because that impacts everything else.
Janice HostagerOkay, well that's that's interesting because uh, you know, I kind of start out with like who is my ideal customer. Um, but you're right, you know, sometimes we can back ourselves into a corner that way by saying, you know, I know my customer needs, they need this, this, and this, but you don't really want to do that. You know, and like you and and I have found myself doing that just from time to time. It's like there everybody's looking for this, everybody's asking me for this. And it's not something I really want to do, you know. Right.
Skip WilsonYeah.
Janice HostagerSo that's a good point.
Skip WilsonExactly. You know, there are things that one of the things that we almost offered, just with my just with my own company, was like a deep dive into ad account auditing, basically going in and saying, hey, we'll, you know, we'll clean up your ad accounts or get things structured correctly. But then when I actually asked my team, she was like, no, that's the part that I hate doing. And so I was about to go to market with something that is appealing to my, to my target audience, like that's what they need help with, but it's more of what we the kind of work that we don't really want to do. And so yeah, you you want to start off with what your what your dream is first. Like what's in an ideal world, what do I actually want more of? That should be the starting point.
Janice HostagerOh, yeah, good, good point. So what's the clearest sign that somebody's about to waste money on some ads? Are there some red flags that you see that
Offers That Convert Versus Free Consultations
Janice Hostagerpeople are or maybe you see this like out and about that other people are doing?
Skip WilsonMost advert I think most of the time when advertising's truly wasted, it's because they've started with picking a platform. For example, like, oh, I'm B2B, so I need to be on LinkedIn. Well, when you start with the platform, you're almost doing it in the exact wrong order. Instead of going, what do I want more of, then who does that thing, and then what do I say to get them to do that thing? They're going, oh, LinkedIn is where businesses are, so let me do something for LinkedIn. And then what ends up happening is self-serve platforms like LinkedIn or like Meta or like Aldi's do make it very easy now to set up your own campaigns. They don't make it easy to set up necessarily good campaigns, but they do make it easy to go from not having something live to having something live. So once you pick, oh, I'm a business-to-business place, so let me put something on LinkedIn, they'll then use the sort of self-generating headlines and those types of things, and in an hour have something live, and it's just most likely not going to perform very well because you know, you're you've taken a guess without really doing the research that LinkedIn's even where you should be. And then you're kind of doing whatever it's recommending is the audience, and then you're sort of letting it dictate what the message is, and it just never it never works well. It's kind of like the old saying that you never want to do, you know, most people are unhappy, in debt, and and overweight, at least in America. So you never want to do what most people do because most people are, you know, out of shape, unhappy and in debt. It's true in advertising, too. Th those advertising models are trained off of average campaigns. Well, average campaigns break even, so yeah, which is not what you want from a campaign. So if you so you never just want to go with off-the-shelf stuff.
Janice HostagerRight, right. I found that particularly true with Google Ads because I have seen a lot of clients lose their shirts on Google Ads. Just not it's but by following what Google tells you to do. Um so I think and and I haven't run LinkedIn ads personally, so I don't I don't know if they are the same.
Skip WilsonIt's just as true. It's true. It's true for all platforms. You know, if you were if and it's not like nefarious, you know, in other words, Google when Google's making those recommendations, it doesn't know what your like target is or what you're really trying to do. What it sees is that, hey, you could get more clicks if you broaden your keywords. You know, so it'll always tell you some version of add keywords, increase your budget, you know, or open your audience, increase your budget, which is always true. I mean, it's almost the same as like, you know, if someone asked, it's like asking, you know, your dentist, like, hey, is there anything else I could do? The answer, you know, for my for my oral health. The answer is always yes. There's always more stuff you could do, right? And so Google's always going to be like, hey, you could reach more people by adding in these things or doing this thing. It's not that Google's evil or like trying to waste your money or anything like that. It's that, no, it's going, hey, you want clicks? I can get you a ton of clicks by adding in, you know, something that's totally not relevant to your business.
Janice HostagerRight. They're just not good clicks. Yeah.
Skip WilsonYeah, exactly.
Janice HostagerYeah. Although, you know, they are in business to make money. So I always keep that in the back of my mind too.
Skip WilsonSo what it's never going to recommend cutting your budget or narrowing your, you know, it's never going to be like, hey, you know what you should do is pause this campaign. You know, it's a very self-serving model for sure. You know, I mean, as it should be. If I, you know, if I'm designing the model for
Red Flags: Platform-First Thinking
Skip WilsonGoogle, I'm going to be doing it with Google in mind, right? I mean, that's whoever built that system, they had they had that, but that's why you shouldn't just go, you know, full bore. That's like go walking onto a car lot and being like, hey, which car should I buy? It's, you know, they're gonna they're gonna keep working you up as high as your budget can go.
Janice HostagerYeah, yeah. So I'm gonna assume that most people right now are turning to AI to do a lot of their writing. I know I have, and I know I've had some very mixed results from it. You know, I I will say, what's a good headline for this? And they'll give me like five different options. And none of them will resonate, I don't think. And and then fight back with with AI. So what what are your feelings about that? What what are your thoughts about AI and have you do you have clients that use that? Or do you use it yourself? You probably do.
Skip WilsonI do, yeah. The I absolutely do, especially if I'm stuck. I mean, there are, you know, there are times where I'm like, I don't know how. I don't write a lot of ads anymore, which is kind of funny because that's how I got into the industry. But now I do very little copywriting unless I'm particularly moved or something. We've got a we've got a team that's much better at that than I am. I use it mostly now to reply to emails. So and but there I definitely do it when I'm like, I don't know how to even reply to this person. Yeah. Then I cheat and I use ChatGPT. But to your point, it does when I have used it for campaigns. I've noticed that it does a better job than like if you're a solopreneur or let's say you know you're a roofing company or an accountant that has no clue what you're doing, I do think that ChatGPT will probably do a better job than than that person at writing the ads. One of the things that I would recommend doing is asking for way more suggestions. You know, if you need five headlines, ask for twenty. And if you get, you know, and out of twenty, there will be like eight or nine passable ones. I do think it's because I do think it's better than than a lot of folks that don't know what they're doing will come up with. What I actually recommend is starting, like I will like is starting yourself, you know, like if you are a roofer accountant or whatever, write out your version of it and then have ChatGPT clean it up and make it better usually produces better results. But it it doesn't compare to having like actual professionals pool like real campaigns yet. I mean, I I think that someday it might. I I have also learned tricks like you mentioned David Ogilvy. I will actually ask Chat GPT something like, you know, what would David, you know, can you take these headlines and make them like David Ogilvy worthy? And it will actually do a decent job of of some of that. So telling it to write in a particular voice can be helpful sometimes.
Don’t Trust Default Platform Settings
Janice HostagerRight. Yeah. Yeah. Well, even I know I've given it writing samples of my own. Yeah. Um and it does okay. I wouldn't say I always have to clean it up, which is to be expected. And good, because it does some things I think have I have no idea where it came from. But also I found that the more information you give it, the better off your results are gonna be. So you're really pony in that audience, what their problems are, how they're feeling at that moment, where what the platform is, all the things. The more information it has, the better it does. But just curious, yeah, because people are gonna use it
Skip WilsonAnd Google now has Google now has, I don't know if you've played around with this yet, but you can toggle on the Gemini feature and the AI expansion, which is helpful and cool. It does basically to headlines what what they do in like broad matching keywords, where it'll take your headlines and then it'll just sort of make up new ones to match the search, which can be effective. Like we've had some results with some good results with it. We have also had it take a, it was a pest control company. And it it made it, it added 20, you know, available 24-7, which is actually not true for this company. And worked that headline in. And it's doing that because it knows, hey, pest control, this is a headline that works well in pest control, but which is great, but it's not quite smart enough yet to go, oh wait, but this company's not available 24-7. And so we've had interesting instances like that happen before as well. So I like the Google AI expansion in theory, but it you have to watch the campaigns.
Janice HostagerYeah, I I don't think I'd let it do it its own on its own. But you know, I would say like for a Google ad, I think it especially for a search ad, I think that would be particularly helpful because you you try to do a lot in a very short number of characters, you know, trying to get a keyword in there and you're trying to get something, and it has to be within this, you know, limited amount of space. So interesting, yeah. So how can someone pressure test their message before putting money behind it?
Skip WilsonOne of the easiest things is to take it to people that are outside of your industry and just be like, hey, could give this a read. Does this make sense? Ideally, they're in your target audience, but I mean, even if it's just having somebody at a coffee shop, you know, just have the barista read your read your stuff and be like and give feedback. I can be incredibly helpful because especially if you are an operate like the owner operator writing your own ads, you're probably going to be using jargon and things that don't really mean anything to anyone else. We have a lot like we have a lot of gym and healthcare clients, and one of the things they love running, and we've got most of them to stop doing it, is like, you know, no join fee. Or no origination fee, those types of things. Well, join fee and origination fee, that's kind of an inside - like we can all guess what that probably means, but that's a lot less compelling than zero dollars down or something like that, or first month free. First month free, everybody knows exactly what that means. No join fee, it's like, well, I still have no clue how much it's going to cost me to come into this gym, right? And so some of those terms things that you just don't want the audience. It's not very compelling if the audience doesn't actually know what it means. And so have somebody outside of your industry read it. I will say that's also a good use of ChatGPT too. I mean, I do think that if you're not using and I I use ChatGPT generically, any, whether it's Claude or Gemini, any AI tool, I do think it's actually a good idea to get the ChatGPT's advice of like, hey, what do you think of these before before running lot? If not, you're just you're not using the tools that you can in today's world. So take advantage of them.
Janice HostagerAbsolutely. Yeah. One of the things that I found really helpful is that, you know, early on when I started using ChatGPT and loved everything I did. Like, oh, you're doing a great job. You know? So I started getting suspicious about this. And so then I, you know, I had to tell it. It's like everything I write, I want you to be, you know, my toughest critic here. I want you to, you know, bring up anything that you think is not good. And it will do that. It's it still holds back a little bit, I think. But that is a good thing to, I think you have to tell it that to do that, because it will not just be tough on you, you know, it will just affirm you, which is part of its popularity, I think. But yeah.
Skip WilsonRight. Yeah. No, it does. It it definitely does have like, you know, the family member effect of like, oh, what that's so wonderful and so great. So yeah. That's that's actually a lot of times where I will use specifically the what would David Ogilvy say of these headlines? What would David Ogilvy say of this? Because yeah, I mean, he was famously a fairly staunch critic of things. So yeah, then it'll give very st strict feedback.
Janice HostagerYeah, right. I like that. I might use that one too.
Skip WilsonYeah.
Janice HostagerUm how about how does somebody actually determine
Pressure Testing Your Message
Janice Hostagerwhere they should be spending their ad money? Do you like your audience first? Or what do you think?
Skip WilsonYeah, once you've decided your audience and you know what you're trying to get them to do, once you know those two pieces, then picking the platform is relatively easy. I mean, depending on your ad budget, you're going to be limited likely to you know, mm-hmm the easiest and best place for most places most businesses to start is online, is some form of online advertising. Now, if you are in a particularly great location or you have something geo-based, then something like signage and those types of things can come earlier. But for most people, you're going to be thinking of an online platform. And so if you know that your target audience is fairly broad, say that you're a roofing company and you just want well, hold off on roofing companies. Let's say that you are an accountant and you and you just want tax prep for the general population, then I would I would recommend something like Meta or Facebook and Instagram together. You know, that's a good place to start because you don't need a lot of targeting. And you know, you're usually just trying to get them to like give you their contact information so you can reach out to them. And Meta is probably the best place to do that. If you are something like a roofing company where you have a where it's mostly needs-based, like nobody is wondering, like, gee, should I, you know, you know, there are some times where you're like in that space of like, you know, should I get a metal roof or something like that? But for the most time, you either need a roof or you don't need a roof. So if you're in that type of business, I would always start with search because you know, you want to reach people in the moment. And so you know, you're gonna be starting most of the time with Google. Those two platforms, Meta and Google, those are the best places I think to really begin for most businesses. I get asked questions like tick about TikTok and LinkedIn if it's B2B. I get asked questions about those platforms a lot. They're great platforms, but TikTok doesn't have a great targeting right now. I think eventually it will. And then there's other platforms like Amazon ads and direct mail broadcast, those things that are that are great, just usually you have a they require a decent size budget or using a company like us, uh shameless plug, that uh where you can where you don't need a large budget, but where you to gain access to those things. So those things you probably have an established thing.
Janice HostagerSo I love doing podcasts, but one of the few things that I don't love so much about podcasting is that sometimes tech fails. And that was unfortunately the case with my last few minutes with Skip. And it's too bad because he had more really good things to share. Regardless, if you'd like to learn more about Skip, you can find him at draftadvertising.com. I'll put the link in the show notes as well. For more information about anything we talked about today, visit myweeklymarketing.com forward slash one four seven. Thank you so much for joining me today. I'll see you next time. Bye for now.
