Selling Boring, Confusing, or Depressing: How to Make Marketing Fun I Love Marketing Live Series with Joe Polish and Dean Jackson - I Love Marketing Episode #477
10 Jul 2026 · 9 min
Joe Polish and Dean Jackson explain how to market boring or confusing products by focusing on benefits over features and using storytelling. They cite David Ogilvy's rule that you can't bore people into buying, then share examples like the "SlickFeet 50 Barefoot Success System" and a weight-loss pebble that turned mundane offerings into memorable experiences through humor and ritual.
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Welcome to I Love Marketing. You've been listening to the I Love Marketing podcast. We took a batch of questions from the I Love Marketing live event and distributed them as individual podcast episodes. And so we're having a lot of fun with that. The next question we're going to ask is, how do you use fun to sell something that people think is confusing, boring, and depressing? Patrick Sokolov, I'm sure I pronounced that wrong.
Boy, I mean, part of that is the delivery of it and the framing of it. And there's a lot of, you know, David Ogilvy, who wrote Ogilvy on Advertising, one of the smartest marketers that ever lived. I'd highly encourage people to read his book. I think it's written in the '80s, right, Dean? Ogilvy on Advertising. And he said you cannot bore people into buying. So there's a lot of people that have very exciting things. But then if you read, you know, Gene Schwartz, Breakthrough Advertising, I mean, you have to evoke a desire that is already there. No matter, you know, it's not, you can't create someone to desire something they have no interest in or, but everyone has a bit of a pilot light that just needs to be turned up. So it's often not what you say, it's how you say it. And that's the whole point of, you know, marketing now. Dean, I almost think this is important to reiterate what the whole purpose of I Love Marketing was created for in the first place. If one of the biggest obstacles people have with being effective at marketing is they underestimate the importance of it, and there's a lot of different perspectives that people have of what marketing is. And if you think of marketing, and many people do, most people actually do, that you're doing something to somebody versus for them, you're going to have a completely different interaction with it. So if you're like, well, I got something that's really boring and you believe that, then you've already sold yourself on the fact that this is going to be hard to sell. You have that again, kind of goes back to what I said earlier. You have to really believe in what it is that you are selling and how there's a benefit to it. And if it's, if it's really boring, but it really works, or it really helps. What is the, you know, pain selling? Uh, you know, David Sandler's original book, uh, You Can't Teach a Kid How to Ride a Bike at a Seminar, uh, is really about pain selling, uh, not just, uh, features and benefits. You know, a feature is what a product or service, uh, is or what it does. A benefit is what it does for the person who's buying it. So even if you think it's boring, what does it do for the person that's actually buying it. And that's what's fun. That's what's enjoyable. When you're selling travel, you're selling the destination. You're not selling the travel. The travel sucks. You're going to go to TSA, you're going to have delayed flights. You're going to, their motto in the airline industry is, we're not happy till you're not happy. You're going to deal with a bunch of bullshit. But if you show up in Hawaii and you see the beautiful beach and you have all this thing and you're gonna have, you know, whatever, a wonderful time with your family or with your loved one or whatever. You sell the destination, you don't sell the travel. No one cares about, well, maybe they care, they don't want to hear about the labor pains, they wanna see the baby. So you gotta, you know, that's where you kind of gotta go at. Those are my thoughts, Dean. So.
Well, by far the most fun that I've ever had in a marketing situation is something that I did with my friend Lane Bowers. And Lane Bowers was a former world champion barefoot water skier, and he had the best training DVD program that was on the market for teaching people how to barefoot water ski, and he was selling it for $59. And we did this super fun project where we were thinking, how can we make it like magic for people to learn how to barefoot. Well, they really think there's some easy way. So we created this product that we called SlickFeet 50. And the idea was, was this magic lotion that you put on the bottom of your feet that could magically make you a better barefoot water skier. And we packaged it as the SlickFeet 50 Barefoot Success System. And the system included that you buy the SlickFeed 50. And we had, we just had so much fun creating the order of things that would happen. You order your SlickFeed 50 and then the UPS man's going to deliver your SlickFeed 50. And then the instructions are to apply a thin layer of SlickFeed 50 on your, on your the bottom surface of your feet, then it's important that you keep your feet fully elevated for 2 hours and then watch the 2-hour instructional DVD that comes with your SlickFeet 50 and then get 8 hours of sleep and you wake up and you're a better barefoot water skier. So we focused on instead of selling the DVD, we sold the SlickFeet 50 for $59 and the DVD was included. But the mechanism that we used to introduce the idea is we sent an email to people and the subject line was confession. And then with the email was, hey Joe Polish, I wanted you to hear this from me before it comes out in Water Ski Magazine and then click here. It was a link and it was like a press release that said, You know, world champion barefooter Lane Dog Bowers swears under oath that Slick V50 does not contain illegal performance enhancers and should be legal for use in international competition. And then we told the story that as, as an Olympic international competitor, I've been tested more than any other person in my sport and have never been never been on the other side of using performance enhancers, but how am I able to ski better than anybody else? And we went through and told the whole thing, and it was just so much fun in writing it. And it was always done with such tongue in cheek that we laughed because sometimes people would come and One of the kids was asking Lane, "Well, this can't be. This isn't real, is it?" Everybody's kind of like, "Santa's not real, is he? This is not really doing anything." A doctor was saying him that, "I'm a doctor. There's no scientific proof behind this actually doing anything." But the system is that you're applying it and you're watching the DVD and guaranteed you're going to be a better water skier after watching the DVD. So it's this, the whole system that makes the difference. We laughed. I've never, I mean, just laughing and laughing, creating this. John Benson and I sat at a Genius Network meeting and we laughed till we were almost peeing with coming up with this idea of a weight loss pebble. That you keep in your pocket and every time you go to eat, you take this pebble and then follow John's diet system. I mean, it was just so funny. You ritualize the compliance of what you're actually supposed to be doing, you know, but making it appear like there's some magic because you've got this pebble.
You've been listening to a live recording of the I Love Marketing Podcast. More questions from this live episode will be presented in future episodes of I Love Marketing. And if you want to attend an I Love Marketing event, definitely head out to ilovemarketing.com to get more information there.
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