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Skip Wilson
American baseball coach
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Sep 15, 2026
How to Build a Smarter Paid Advertising System With Skip Wilson
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Skip WilsonGUEST
And like every industry, AI, of course, is like, is, you know, a major factor in it.

Skip WilsonGUEST
One of the things that for ads specifically, like paid media placement specifically, is The need for creative variation, it used to be you were A-B testing or you'd have two or three different headlines or two or three different images.

Skip WilsonGUEST
Now you really need to have more like 50 to 60 headlines or 50 to 60 different images because otherwise you're just going to get outpaced by your competitors because your competitors probably have that many different variations of ads running.

Skip WilsonGUEST
Similarly, it used to be that if... that it was pretty simple with medium to small budgets.

Skip WilsonGUEST
Like you begin with search, then you layer on top social, and then you layer on like brand elements and those things.

Adi KlevitHOST
Who do you recommend using paid ads? What kind of businesses? Who does it work well for? Who doesn't?
The Draft Mentality: How Skip Wilson Forecasts Advertising Success Before You Spend a Dime
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7:16JeffroHOST
Like, what does that mean? And why did you build your whole company around that concept?

Skip WilsonGUEST
Like if you think of like a movie, like any movie where there's zombies in it, zombies always win.

Skip WilsonGUEST
And even though they're not the smartest or the best, they just are kind of relentlessly pursuing this single goal.

Skip WilsonGUEST
And they kind of I mean, just by sheer force and relentless pursuit of one thing, they get there.
16 MINS LATER
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23:17JeffroHOST
Do you trust Cloud or Gemini to create and run campaigns for you at this stage, or is it more of a helper?
The Advertising "Black Box" Myth: Why Your Ads Aren't Working (with Skip Wilson)
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3:22Sam MorrisHOST
I would love to know what's changed from when you started at 16 to what it looks like today.

Skip WilsonGUEST
Well, when I first started, I got into it because I thought of myself as a writer, right? And so I was like, oh, I want to be a writer and be creative and all of those different things.

Skip WilsonGUEST
Now, one thing that's changed is I know that I'm terrible at creative and that's not my strength.

Skip WilsonGUEST
Still enjoyed some, but the big part of it, I mean, I got into web design right after that.

Skip WilsonGUEST
Like most businesses were like, why do we really need a website? Is this really going to be here? Then, of course, social media came around and everyone was like, you know, you either had businesses that thought, well, social media is going to completely change our business and they were going all in on it.
21 MINS LATER
EP 306 - Future-Proofing Your Marketing Career
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Skip WilsonGUEST
In the beginning for me, I mean, marketing very much was a I saw it as mostly a means to make money.

Skip WilsonGUEST
And then eventually I realized how important, I mean, I think that the difference between a company that's doing, that's thriving and growing and a difference and a company that's shrinking and dying really is, is marketing.

Skip WilsonGUEST
I think, you know, it's, I would say arguably more important and maybe I'm biased, but I think it's more important in a lot of ways than even like product and service and those other things.
5 MINS LATER
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12:32speaker_2UNKNOWN
you know chat searches right now and it's I mean I get a ton of them
How to Win at Google Ads When the Machine Is Making All the Decisions | Skip Wilson
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Skip WilsonGUEST
[laughs] Yeah, the not so ni- like, you know, you might not be a family-friendly pizza place.

Skip WilsonGUEST
Like, uh, the, um, the, uh, the, the part that is particularly hard is, um, it, it, it kind of forces you to, everyone to have more or less the same campaign, 'cause you're forced to sort of pick what category you're in.

Carl WillisHOST
And so the way we structure our advertising, uh, we have to think a little differently about what it is we're gonna answer in that ad and the way we're gonna talk to that consumer.
228. Targeting Isn't Enough: An Overlooked Driver of Rising Customer Acquisition Costs
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Sonia ThompsonHOST
The question is not, Did we include a person from this community in the campaign? The question is, what signals are we giving this customer that tell them they belong here and that this offer was designed with their reality in mind? And that question gets even more practical when you look at how customers decide whether something is actually a fit.

Skip WilsonGUEST
One of the biggest purchasing decisions is how much of a fit is this thing for me? And like you said, it could that could be relating to do I have the time to invest in this? Is this for somebody in my stage of my career or do I need to know what I'm doing a little bit more? Do they have my thing that I'm always looking at? I can't just walk into any clothing store.

Skip WilsonGUEST
I need to know beforehand, like, are they going to have plus sizes or not plus sizes? You know, those types of things.

Skip WilsonGUEST
You're always trying to filter out how much do I fit this? And so that should absolutely always be in the creative.
10 MINS LATER

Sonia ThompsonHOST
Audience strategy may live with media, messaging may sit with brand, creative may come from an internal studio or an agency, landing pages may be owned by web or demand gen, and every team can be doing the work they were asked to do while the customer still experiences a journey that feels disconnected.
July 7, 2026 – Media Ad Wholesalers Skip Wilson and Leader With A Heart Lorenzo Payman
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Skip WilsonGUEST
But the biggest thing, I mean, the biggest thing was just listening to the market.
7 MINS LATER
From Copywriter to CEO-Skip Wilson’s Incredible Journey
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Skip WilsonGUEST
Yes, which is one of the most frustrating things to hear because you know that, well, that means that we can't do anything, right? Like someone's like, oh, we do all things.

Skip WilsonGUEST
Anybody with teeth that live within a two-hour radius, that's our customer, right? Because you get those types of answers sometimes.

Skip WilsonGUEST
And, but one of the things that helps bring that down is just a realization of usually, usually if someone gives that kind of answer, I'll appeal to the money side of it is I'll go, well, okay.

Skip WilsonGUEST
So if, unless you've got enough money to reach, it takes anywhere from a five to 10 frequency, meaning you got to reach the same household five to 10 times in a either we can reach either you've got enough money for me to put an ad five to ten times in front of every person with teeth in this area which you probably don't um or we're gonna have to get more specific than that and then and usually i mean usually uh we're working in an industry almost always where we've had some direct experience before so um the that's the that's the one benefit is that uh myself and even most of my team that's getting less and less true now, but for the most part, me and most of my team have over a decade of experience, each, each one of us.
8 MINS LATER

Darren MitchellHOST
And I know you don't necessarily work directly with the customer, but how much science goes into really understanding that particular customer's business and what sort of science is behind everything so it becomes a little bit more predictable?
From Guesswork to Growth: Data-Driven Advertising That Works
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Skip WilsonGUEST
I've found that business owners typically think in terms of either platforms or creative.

Skip WilsonGUEST
And if they think more in platforms, then they'll say things like, oh, I've tried meta and it didn't work.
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11:45Paul SweeneyHOST
It's a common problem across business in general, but I think specifically small business think that they are limited by budget and really looking for that – instant success or that big success without having to commit to the process what i really like about your work and and it's quite exciting and there's a bit of a numbers nerd coming out in me here uh getting excited but this whole idea or this concept of forecasting advertising success before you spend your money now can you just expand on what do we actually mean by that

