The Draft Mentality: How Skip Wilson Forecasts Advertising Success Before You Spend a Dime

Jeffro (00:01.572)
What if you could forecast whether your advertising campaign was going to work before you ever spent a dollar on it? Sounds too good to be true, right? Well, today’s guest built his entire business around making that possible. Skip Wilson is the founder of Draft Advertising, an advertising execution company that works with CMOs, internal marketing teams, and agencies to plan, execute, and optimize paid media campaigns, everything from digital to traditional media to direct mail and here’s a fun fact about Skip. He got his start in advertising at 16 years old as a copywriter. And I’ll let him tell you the real reason why. but from there, he built his own web design business, worked on CNN’s iReport team, helped out the digital division at Clear Channel Radio, and spent over a decade as vice president of digital media at iHeartMedia. Today, draft advertising serves over 100 clients across four locations, and they’ve twice been recognized as at the innovation in business Mar Tech Awards, including Best Marketing Software Developer.

So today we’re gonna dig into how to get real results from advertising. We know it works, right? How to actually forecast success before you spend a dime and what Skip calls the draft mentality. So if you’ve ever thrown money in ads and just hope for the best, this conversation is going to change how you think about every dollar you spend. Skip, welcome to Digital Dominance.

Skip (01:16.342)
Thank you for having me.

Jeffro (01:18.048)
Absolutely. And I think we should start with that origin story. You know, you got into copywriting at sixteen trying to impress a girl, right? So tell us that story and and how that, you know, spun out into your career.

Skip (01:25.614)
It’s it’s right.

Skip (01:29.942)
So I told her that I was a writer and then we started dating and so then I was like, well ’cause I admit that more is like an aspirational thing more so than more so than an actual thing. But once we started actually dating then I like, Okay, well I gotta make good at on this. So I looked up what writing jobs there were around me and started hitting literally cold door knocking ad agencies and it’s actually pretty easy, honestly, w to to get some stringer work. So I’d get paid like thirty bucks an ad, you know. Not enough to make a living, but enough to at least get my foot in the door.

Jeffro (01:33.648)
Yeah.

Jeffro (01:59.055)
Nice. But I I like that you you aligned your statement with your real life, right? To make sure you stayed in integrity, right? So good for you.

Skip (02:05.897)
Right. Yeah, right, exactly. It’s only it’s just like right after that, actually in that same like little s run, I was asked, Hey, can you design websites? And I said no because I didn’t know how to do them. but but I was right as WordPress was like launching and becoming a thing and they were like, Well, it pays five grand. And I was like, Okay, well yeah, I can do that. And so it’s only not true if you don’t follow through. I feel like if you follow through with it, it’s okay, right?

Jeffro (02:28.206)
I can figure that out.

Yeah. That’s true. Well, I mean, obviously starting there, you’ve had an incredible career arc from CNN Clear Channel, iHeartMedia. What what did all of those experiences kind of teach you about advertising specifically that you couldn’t have learned anywhere else?

Skip (02:49.483)
definitely I think learning that it is a art or like it is a science. It’s not just an art. Like it is an art form and I and I love advertising and I love marketing in general, but it is very much like an objective passfail type of tool. And it should be like kind of a repeatable system. I would say that that’s something that I wouldn’t have come to like on my own, but it’s definitely the way I feel like it should be.

Jeffro (03:16.76)
Ha are there tools inside those larger companies that maybe smaller companies don’t have access to, or how how is that done?

Skip (03:23.339)
Yeah, no. So yeah, absolutely. especially I mean, especially from like post search days onward. so I’m so old that when I was starting, like most when you people talk about advertising for the most part, they were talking about radio, TV, like you know, direct mail, those types of things. But right as search was launching and then eventually social the ability to track stuff made everyone in the traditional media side start to panic. We were like, okay, we gotta come up with some way to track our stuff too. And they develop good ways. Like anybody that says like advertising’s not trackable, that’s just not true. It’s just some may sometimes not trackable if you’re not spending enough or taking the time to set those things up properly. And so yeah, I mean the ability to get down to especially household level like attribution, that exists on almost every type of media now.

Which is great. It’s just it’s kind of a walled garden. Sometimes you have to have a big budget to get there. But I mean, that’s that’s part of not to get already into talking about draft, but I that’s part of what like what our whole thing was was that I didn’t realize that that was exclusive because I’d only really worked with major companies at that point. I didn’t realize that that was something that wasn’t available to everyone until sort of finding that out the hard way, if you will.

Jeffro (04:41.188)
Yeah. So I mean, you were a in a VP role at a major media company. What made you decide to leave and start draft advertising?

Skip (04:49.473)
So we launched as a SAS. Like our original idea was, okay, we’ve got the and this was in 2021, late 2020, early 2021. like I was I kept getting this question of like, hey, if we give you a million dollars, what can we expect in return? And I knew that the answer was findable because we know like what a landing page should convert at, and we know what the cost to get someone from not knowing who you are to that landing page is. So I’m like, these are knowable things that shouldn’t be a I don’t know type of thing. So essentially we built this planning software that would be like, okay, if you’re a roofer in Des Moines, here’s what the CPM is in your market, here’s what the cost per click is in your market, here’s what your media mix should be to get the number of leads you you want. The idea was let’s sell this planning software as a SaaS to agencies. And then and I was so like committed to that vision that I was like, you know what? I’m doing it. We’re going out. I built my own like little division inside iHeart, which did well, but you know, there’s something when you build like a team that grew up grew up to be like a $22 million division and then you’re like, but my pay’s the same. you know, for after 12 years of doing that, you’re like, I think I’m gonna do it this time and here’s you know, and do it you know, under my own company. But that SAS model failed because that’s when I realized, you guys don’t have access to we would be handing these like, you know, 10 and 15 person ad agencies or sometimes even smaller ad agencies a plan.

that it’s like, okay, you guys execute this and then they would be like, this is great, but we don’t have access to any of this stuff. So that’s what made us sort of realize, that’s the better idea. Took us about eight months of trying to sell it as a SAS to to to do that, to make the jump to that.

Jeffro (06:31.886)
And sometimes that’s what it takes to figure it out, right? tell us a little more about the name and the philosophy behind the draft mentality. Like what does that mean and why did you build your whole company around that concept?

Skip (06:34.827)
Yeah.

Skip (06:44.937)
So I have sort of this saying that is kind of a dumb saying, but I like it. that like zombies always win. Like if you think of like a movie, like any movie where there’s zombies in it, the zombies always win. Like you know what the ending of the movie is before you go into it. And even though they’re not the smartest or the best, they just are kind of relentlessly pursuing this single goal. And they kind of I mean, just by sheer force and relentless pursuit of one thing, they get there. And I kind of take that mentality into everything.

Jeffro (06:52.93)
Ha ha.

Skip (07:14.091)
Where it falls into ad campaigns in particular is once you know like what an average campaign is. So for that roofer and Des Moines, what is a good cost per lead and customer acquisition cost for my company if it just performs average? Then it becomes simply pass fail. Like is my campaign meeting that or not? And if it’s not, then you just all you have to do is look under the hood and break it into its pieces and figure out like, okay, is the click through rate not where it should be, or are they not spending the time on site that they should be, or is my landing page not converting? Or it becomes very easy to diagnose. And so that idea of pass fail, like a lot of times I’ll hear, we’ve tried paid media and it didn’t work. We’ll try we tried insert thing and it didn’t work. But that’s too broad. Like it should work. You know, if you’re getting a specific message to a specific audience to get them to do something, then the only way that doesn’t work is if they

No one cares about that message. And so and if that’s the case, just tweak the message. So it that’s w draft mentality comes from the idea that nothing when you launch is perfect. But if you know what it should be, or like if you have a very clear vision of here’s what this number should be, then it just becomes just sort of that zombie relentless pursuit of tweaking things until it gets to that number, and then you go next one download.

Jeffro (08:36.238)
Right. So it’s like your first draft of a paper, you know it’s not gonna be the best, but you got it done. You can revise from there rather than waiting th for it to be perfect, which it never will be, you start with something and iterate, right? so I I mean th this is the part we really want to dig into, right? So how do you actually forecast whether an advertising campaign is going to work before any money is spent? I mean, you’ve you’ve mentioned we know past data. Is that what you’re talking about? We just look at

Skip (08:46.478)
Exactly.

Jeffro (09:03.918)
what other companies have done and then projected onto, you know, what we’re trying to do.

Skip (09:08.479)
That’s essentially the big secret. Yeah. Like you can do you should always have always you should always start off by thinking, okay, what’s the thing I’m trying to get a person to do? Is it phone calls, is it form fills, is it whatever? Like what is the entry point for a person into my company? Then you just try to figure out, okay, who is my ideal customer? And then it becomes as simple as what do I need to say to that ideal customer to get them to do that specific thing. Once you’ve got that ironed out, then it just becomes the simple math of like, okay, what are those stages? Sometimes it’s asking for like a you know the appointment. Like if you’re in a more emergency services side, like plumbing, roofing, those types of things, you can just straight up ask for the appointment. If you’re in more like custom home or remodel or those types of things, then you know you’re probably not going to be able to say, get a quote today and have that work. You’re gonna need some sort of journey for them. So once you know who you’re talking to and what you’re trying to get them to do,

Break it up into those stages and then okay, this stage, cold audience. I’m trying to get them to do this specific thing. Then next stage. All right. Once the people that do that specific thing, how likely are they to convert it the next? And each one of those steps is an I mean, especially in the AI world, it’s a search away or a conversation away to figure out like what a good rate of people entering that side and leaving that side is. And then now you’ve got your scorecard. So you can literally do it on like a cocktail napkin most of the time.

Jeffro (10:39.152)
Do you ever look at the ad libraries on Facebook and Google to see what other people have done and go based on that to figure out a starting point for your draft?

Skip (10:51.614)
Definitely for the messaging piece, yes. the once you know like so once you’re sort of past like, okay, this is an acceptable customer acquisition cost. Like okay, it’s gonna be whatever it is, fifty bucks a lead and a $150 customer acquisition cost, something like that. Once you get past the math part of a part of it, then yeah, that’s the next exploration. It’s like, okay, what messaging is working in the market? And then and I think Facebook ads library, Google’s transparency.

Those two tools, yeah, are like an endless wealth of figuring out what’s working. I always sort by like what’s run the longest, because usually the longest running creative is kind of the the money maker. Because what you don’t want to do is like copy what, you know, if they just launched an ad two weeks ago, they don’t know whether that ad’s working or not either. So no point in c Yeah, exactly. So don’t copy that one yet. You want to find like what’s been running for about six months and or longer. And that’s

Jeffro (11:30.928)
Mm-hmm.

Jeffro (11:38.832)
They’re still testing, yeah.

Skip (11:48.313)
Then like, okay, how does that apply to my target audience?

Jeffro (11:52.796)
So for someone who’s already launched a campaign and they’re just hoping for the best, how can they treat that like their first draft and then edit it to make it better?

Skip (12:03.276)
So the you want to think of it in terms of stage. Like for almost every campaign it follows a stage of cold audience to get them to do something specific and then lead and then lead nurturing. Like that’s kind of the like almost every campaign that’s that’s the steps. And so if you sort of layer lay those out, you wanna look, okay, if you’ve got let’s say that you’ve got a a cost per lead of like five hundred bucks and you know that that’s not tenable because you’re that’s how much profit you make maybe on your average job.

Then the first thing that you would want to do is figure out, okay, is my click-through rate and my cost per click above average or below average? If it’s at average or below, then that’s fine. Move to the next thing, which the next thing to look at is time on site, which that is the metric that I think people ignore the most. But time on site, if it’s under 15 seconds, you probably have a lot of like bots and fake traffic on your site. And so if they’re spending four and five seconds on your site,

That’s not because your landing page stinks or because of you know, bad copy or anything else. It’s because it’s probably not real human beings. So, but if they’re spending longer than 15 seconds and you know, especially if they’re spending 30 seconds or or more, then you’re getting real people to click your ad. So your ad itself is doing its job. Then it becomes dialing in that landing page and getting that conversion.

Jeffro (13:24.825)
Right. There’s different conversions, right? There’s the add conversion, which is the click, and then there’s the actual conversion that the owner cares about, which is do they make the phone call? Do they fill out the form? Yeah. So do you when you’re doing your analytics and track, are you just using Google Analytics? Do you have another third party one that’s more flexible? What do you like?

Skip (13:32.076)
The actual le Exactly.

Skip (13:42.945)
I d Google Analytics is fine. I do think that they have intentionally made time on site like very difficult to find. my fa my favorite free one is Microsoft Clarity. Like Microsoft Clarity is free. It very much like a like a hot jar or or those types of things where it does the actual like user interaction, like user recordings and cursor movements, and it makes time on site front and center. So

Jeffro (13:51.153)
Okay.

Jeffro (13:55.505)
Interesting.

Skip (14:09.292)
Microsoft Clarity is my favorite free tool for for conversion rate optimization.

Jeffro (14:14.917)
Have you noticed any like performance hits with using the heat map tools or anything?

Skip (14:20.99)
Yes. like I said, one of the biggest things nowadays is trying to figure out, like if you’re getting decent traffic to a site but it’s not converting, is trying to figure out if they’re real human beings or not. ‘Cause I’ve seen a lot of people put a lot of like, okay, we need to tweak the copy on this or we need to tra change this, but it’s not real human beings. So there’s, you know, no point. You still got an ad problem, not a landing page problem. that is unfortunately in today’s world a massive a massive thing to to consider.

Jeffro (14:39.377)
Mm-hmm.

Skip (14:51.028)
but then yeah, the and I would like to say that it should always be like, you know, large image or video or headline, but unfortunately it kind of depends on your market and specifically like, you know, if you’re a plumber, I don’t really care how beautiful your work is or anything else, right? Like I just need to know that you’re available today. if you are a but if you are a plumber that focuses more on like remodels and or tankless water heaters or those types of things.

Then you are going to want nice imagery and very clear call to action type headlines. The things that are the same is you want to keep the top, the top of your page for lazy folks. So the top of your page for the people that just immediately want to take action. So clear headline, you know, hey person, you probably need this thing and here’s why. Click here to do this thing. Like that part pretty much always stays the same. And then the rest of the page is for the people that like to research.

Jeffro (15:35.921)
Mm-hmm.

Skip (15:48.591)
So I do like long copy. Like a lot of times you’ll hear like, you know, it needs to be short. No. Headlines should be short. Rest of the page you can it can be as long as you want.

Jeffro (15:54.331)
Yeah, yeah. If you’ve got

Jeffro (15:59.952)
Yeah, if you’ve got the right p person on the page, then you can keep speaking to them and sell them overcome objections or whatever. So by the time they get to the bottom, it’s an easy sell once they schedule that meeting. So I I mean there’s so many ways we can talk about this, right? but I’m curious, what’s one of the biggest mistakes you see even sophisticated marketing professionals making with their paid media?

Skip (16:11.352)
Exactly.

Skip (16:24.408)
So not having the proper grasp on attribution, I would say, is one of the biggest mistakes that even major advertisers have. Cause usually they’re either using no system at all, like no real tracking metrics at all, or they’re using something that’s like baked in their CP CRM. Like if they’re using HubSpot, they’re using that, which is fine, but it’s only going to count last click. So in other words, if someone sees your ad on Hulu and then

Googles you and comes to your page because of the Google ad, it’ll give credit to the Google ad, even though that household was reached. So there’s a ton of places to get household level attribution, but that is that is something that if you’ve got less than a $2,000 ad budget, it’s not worth paying for because it’s probably going to be like five hundred bucks a month. But if you have much more than that, it’s definitely something that should be the next layer is focusing in on like.

Jeffro (17:10.385)
Right. Okay.

Skip (17:21.13)
whole household attribution. Because only then do you get like a real picture of what the sales funnel is.

Jeffro (17:26.811)
That makes sense. So for someone, let’s say a service business owner, they already either have their internal marketing team or they’re working with an agency. How do they know if they need better campaign execution and optimization versus just accepting what is happening right now?

Skip (17:41.838)
Well, so the f first number that you should ask, especially if you’ve got a team managing for you, is what’s my customer acquisition cost? Because at the end of the day, that’s the one metric that matters. Like, are you getting at least a three X row as? some businesses are more some businesses can be even more than that. But it should be at least a three times whatever you’re spending to get them in the door. Your net profit should be, you know, three times. Three times that. so and if you don’t get a clear answer on that, then that’s your red flag number one.

Like if you get, you know, hey, what’s our customer acquisition cost? And they Well, our cost per lead is this, then that’s already you know something’s off, right? It’s like, well, that’s not the question I ask. And so knowing what that number is i is is is good. If it’s a three X, you see if you can get it to four or five X. if it’s you know, unknown or less than three X, then you’re below average by definition. So let’s

Jeffro (18:17.627)
No, no.

Skip (18:39.439)
You know, tweak that campaign until you can get it above average.

Jeffro (18:43.129)
It and and yeah, and I think that it’s important to point out that this is an iterative process, which is again why the name, the draft mentality makes sense, right? It’s never gonna be perfect, and even when you get it performing at a certain level, it won’t stay there forever because markets change, people’s mindset changes, you know, whatever’s out there, new stuff gets released. So you kind of have to always be innovating and monitoring it to try new stuff and keep it working.

Skip (18:49.796)
Yeah.

Skip (18:56.718)
Yes.

Skip (19:09.035)
Exactly. Yeah, there’s no such thing as having a campaign that’s just done because like you there’s competitors moving into the market, there’s new platforms moving in, people are like customers are moving in and out of the market, people’s habits change, chat bots and forums were great two years ago. Now the phone’s back and you know, so it it’s like even the top level recommendations of like, Hey, no one’s gonna call you, they don’t like talking to you. Well, that’s true a few years ago. This year people love talking to people and they want your phone number, so who knows? yeah, right. Exactly. So yeah, this year it’s it’s all about phone calls. That may change next year. We don’t who knows what it’ll be next year.

Jeffro (19:38.287)
Yeah. They’re tired of the robots.

Jeffro (19:48.918)
Yeah, and I’m also curious because technology keeps changing, AI is growing rapidly. obviously you’ve built marketing software in the past, so this is I expect something you still rely on. how has AI changed how you plan and execute, optimize campaigns over the past couple of years? And what do you see happening going forward?

Skip (20:09.496)
well, one th one thing it’s done for us is greatly shortened. Like it used to take us, like even in our planning software, it would take us about thirty or forty-five minutes, or it’d take the user about thirty or forty-five minutes to actually go from answering the questions to getting the plan. Now it’s more or less instant. That’s one nice one big nice change. just made our internal processes a lot faster. but the other thing that is is been a big help is that you can now like aggregate data better than ever before. So having like your ad logs combined, you know, and comparing that to a system that identifies household level data, that is something that I mentioned before it’s about five hundred bucks a month now. It was that would have been two or three grand a month minimum, even just a couple of years ago. And the only reason it’s cheaper is cause now you just have to pay for the data because you can spend an afternoon on Replit or you or make or whatever your whatever your you know, software maker of choices and code out something that basically compares ad logs to house data and then there you go. You’ve got a nice attribution model that is better than what most people use. So that’s definitely one thing that’s changed.

Jeffro (21:19.985)
Okay. and it’s interesting, you know, hearing you talk about that, it obviously at this point comes naturally to you. But for someone listening, and wants to take advantage of AI to help them in this area, how do they know what they don’t know? How do they talk to Claude to help them through this process?

Skip (21:39.184)
So once you get w the average information for your market, so once you find out like, hey, what should a convert what should a landing page be converting at in my industry? Which that’s just a Google search away. Once you get that information and you do that for each phase, so like what’s a good cost per click on Google for my industry? You know, you sort of ask those series of questions to get that hard data, then it’s it takes no time to set up a custom cloud agent or a gym and gym and I or

you a custom GPT with your specific industry metrics and then upload your upload your information even if you’re just using you know crappy Google Analytics or just the reporting just from the platforms. export those things, upload it in there, and then ask it, hey, identify where it’s breaking down right now. And it’ll do a decent job point pinpointing, you know, hey, here’s here’s the part that’s off. You’re paying five times the CPM of what’s or cost per click you’re paying five times the cost per click of what your what your market is or whatever.

Jeffro (22:40.881)
Do you trust Cloud or Gemini to create and run campaigns for you at this stage, or is it more of a a helper?

Skip (22:48.759)
It’s more of a helper. I would not the one of my big pet peeves about like one of the recent Google changes is that Google now alters your headlines and keywords like without asking. Like instead of it being an option, it’s just gonna do it. And I know why they’re doing it. And honestly, their reason is a good one. People are just searching different, you know, instead of saying pizza place near me, you’re now saying, you know, it’s nine PM and I’ve got three small kids and I need a pizza place that’s safe, that type of thing. so It wants to have the flexibility to change headlines. So I like that. But as a marketer, it’s also annoying because I know that we’ve had we had a we had a pest services company call us. this was right after they made that change. So this was back in March of this year. We had a we have a p a pest services client and they called us up and they’re like, you know, what’s this ad that says we’re open 247? And I’m like, wait I don’t think that’s ours. And so we on Slack were like messaging each other, like, is this is this our ad? Whatever. But we looked at the system. We don’t have that headline anywhere, but Google s knows that 24-7 performs well in the pest control space. So it added that headline to to that campaign, which is a problem if you don’t offer 247 service. And so I don’t yet I I love it as a helper.

Jeffro (23:57.266)
Ha ha yikes.

Jeffro (24:07.739)
Wow.

Skip (24:11.779)
But it right now I take all the headlines, keywords, all of those things, all of its recommendations, put it in a spreadsheet, then I look at that spreadsheet and before I go live. It’s it’s not that good of a copywriter yet. And I think I do think eventually that will change, but for right now, I would not trust it to completely launch a campaign.

Jeffro (24:12.388)
Mm-hmm.

Jeffro (24:33.519)
Okay. Take it with a grain of salt. Let it help you. But that that’s crazy. Just you know, twenty-four seven. Like, okay, no. Yeah, just make stuff up.

Skip (24:36.259)
Exactly.

Skip (24:42.605)
Yeah, right. Exactly. It’s it it it but you know in Google Google’s going, Hey, this is a pest services company and and we were part of their like beta test of this thing, but it’s going, Hey, this is a pest services company and people love this headline on pest service ads, so let’s add it across the board. And so it’s like no, not a good idea.

Jeffro (25:03.461)
Well, this has been really practical and helpful, Skip. I think a lot of our listeners have been guilty of the spend in pray approach to advertising and kind of what you’ve walked us through today with the forecasting, the draft mentality, and then optimizing, it’s it’s a really helpful framework to have to think differently about the dollars that you’re putting into your marketing and your ad spend. So for those of listening, whether you’re working with an agency or you have an internal team or you’re doing it all yourself.

These principles are gonna apply regardless of the size of your budget. but like Skip said, you know, you if you don’t have access to something, you know, don’t worry about the high level attribution stuff. If you’re not there yet, totally fine. But you can still benefit from doing it this way. So Skip, for people who want to learn more about draft advertising or connect with you directly, where should they go?

Skip (25:51.277)
Best place is our website, draft advertising dot com or info at draft media partners or draft advertising dot com. Either of those. Same website. Draft Media Partners, Draft Advertising, same website. but info at in front of that. We do build the plans and give you the plans for free. So we still do that. We used to charge that as a SAS, but now we give that away for free in hopes that you do the ads with us. So if nothing else, you can get a free plan.

Jeffro (26:14.285)
Yeah. I mean, guys, that’s a great deal. Especially if you’re gonna try to do AI, do your first one with Skip’s tool. And then if it makes sense, hire him or, you know, try yourself. That’s awesome. Thank you. also guys listening, this is the takeaway, right? You know, before you spend another dollar on advertising, ask yourself, can I actually predict whether this is gonna work by looking at what other people have done? Or am I just hoping? And if you if your honest answer is hoping, might be time to rethink it and spend a little more time, you know putting some thought into this before you put money behind it. So thanks again, Skip. Thank you. Thank you to everybody for listening. Make sure you subscribe to Digital Dominance and take care. We’ll see you next time.