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

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.

Resources

• Ogilvy on Advertising | David Ogilvy's advertising classic, cited for the rule that you cannot bore people into buying.
• Breakthrough Advertising | Eugene Schwartz's 1966 copywriting classic on tapping desire that already exists.
• You Can't Teach a Kid to Ride a Bike at a Seminar | David H. Sandler's sales book behind Joe's "pain selling" reference.
• Genius Network | Attend the Next Genius Network Event.
• I Love Marketing | Subscribe and Join the Next Live I Love Marketing Podcast.