At a live I Love Marketing event, Joe Polish and Dean Jackson answer the question every marketer eventually runs into: how do you sell something people find confusing, boring, or depressing?
Joe and Dean answer with a swing through David Ogilvy, Gene Schwartz, and David Sandler, and one of the strangest, funniest product launches.
Here's a glance at what you'll learn from Joe and Dean in this episode:
- Why Joe Polish says you cannot bore people into buying, straight from a rule David Ogilvy wrote decades ago that still holds up today.
- The exact moment you sabotage a "boring" product, according to Joe, and why believing it's boring is the real problem.
- Why nobody buys the flight, the hotel, or the TSA line: the destination versus travel distinction that reframes any hard to sell offer.
- Inside Slick Feet 50, the $59 lotion that never claimed to do anything, and how Dean and world champion barefoot skier Lane Bowers turned it into one of his most fun launches ever.
- The "confession" email disguised as a leaked Water Ski Magazine press release, and why customers asking "is this even real?" was exactly the point.
Show Notes
The Question: Selling Something Boring, Confusing, or Depressing
- Joe and Dean demonstrate how to use fun to sell a product or service that people assume is confusing, boring, or depressing.
- Joe frames the answer around delivery and framing before anything else.
You Cannot Bore People Into Buying
- Joe cites David Ogilvy's Ogilvy on Advertising and Ogilvy's rule that boring people never sells.
- Even genuinely exciting products fail if the delivery is flat.
Desire Already Has to Exist
- Joe brings in Gene Schwartz's Breakthrough Advertising and the idea that marketing cannot manufacture desire from nothing.
- Every person already has "a pilot light" of interest that marketing has to turn up, not create from scratch.
- It is less about what you say and more about how you say it.
Marketing With People, Not At Them
- The founding purpose of I Love Marketing: most people underestimate how important marketing actually is.
- Framing marketing as something you do "at" someone instead of "for" them changes the entire interaction.
The Trap of Believing Your Own Product Is Boring
- Joe says if you believe your product is boring, you have already talked yourself into a harder sale.
- You have to actually believe there is a real benefit before you can sell one.
Pain Selling: Features vs. Benefits
- Joe references David Sandler's book on pain selling, noting that a feature is what a product does and a benefit is what it does for the buyer.
- Even a "boring" product can be sold hard if you focus on what it actually does for the person buying it.
Sell the Destination, Not the Travel
- Joe compares selling to booking a trip: nobody wants the delayed flights or the TSA line, they want the beach in Hawaii.
- The lesson applies to any offer: sell what the buyer arrives at, not the process of getting there.
- People do want to hear about the "labor pains," but only because they want to see the baby.
The Slick Feet 50 Origin Story
- Dean's favorite marketing memory involves his friend Lane Bowers, a former world champion barefoot water skier, and his $59 training DVD.
- They created "Slick Feet 50," a fictional magic lotion for the bottom of your feet, packaged as the "Slick Feet 50 Barefoot Success System."
- The system layered up a full ritual: apply the lotion, elevate your feet for two hours, watch the two hour instructional DVD, sleep eight hours, and wake up a better skier.
The Confession Email
- The launch email had the subject line "Confession" and read like a personal heads up before a Water Ski Magazine story broke.
- The linked "press release" had Lane Bowers swearing under oath that Slick Feet 50 contained no illegal performance enhancers and should be legal for international competition.
Tongue-in-Cheek Marketing That People Question (and Love)
- Kids and even a doctor asked Lane and Dean if Slick Feet 50 was "real," comparing it to finding out Santa isn't real.
- Dean says the product was always sold with a wink, and the skepticism itself became part of the fun.
Ritualizing Compliance With a Wink
- Dean and John Benson later laughed almost to tears designing a "weight loss pebble" you keep in your pocket and touch before every meal, paired with John's actual diet system.
- The idea was never that the pebble did anything on its own. It was a way to ritualize following the real system underneath it.
Why Fun and Curiosity Sell Better Than "Serious" Marketing
- Across every example, the common thread is a system wrapped in enough curiosity and humor that people want to follow it.
- It is not the product that has to change, it is how it gets framed and delivered.
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