If you're not #1 in your category… your only hope might be to get really, really weird.

In this episode of The Checkout, John, Zoe, and Bart (with Shack out this week) dive deep into what it takes to stand out in a saturated market. From Charleston Chew to Dr. Pepper, sliding mitts to Dad Gang hats, we break down the strategies behind products that win by being different—not bigger.

We talk:

- Why weird wins when you're not the category leader

- How packaging and product design can disrupt legacy spaces

- Tootsie Roll, Liquid Death, canned vegetables, and the “X for Y” framework

- What NIL (Name, Image, and Likeness) deals mean for brands

- Why influencer trust is collapsing—and what that means for marketers

- Plus: The underrated brilliance of skit creators like Veronica is Cool

If you’re building a product, a brand, or just love seeing how weird stuff wins, this one’s for you.

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💼 Sponsors of This Episode:

Marpipe – The multivariate testing platform built for performance creatives. Discover your best ad combinations faster and scale what works.

👉 https://www.marpipe.com

Heatmap.com – See what your visitors do on your site—where they click, scroll, and drop off. Heatmaps, session replays, and powerful insights to optimize conversion.

👉 https://www.heatmap.com

Chapters:

00:00 – Intro & what this show is about

01:30 – Why weird brands win

08:00 – Product and packaging that stand out

18:00 – Niching down vs. going mass

27:00 – The “X for Y” framework

35:00 – Distribution strategy matters

45:00 – NIL deals and underrated influencers

55:00 – Do people still trust influencers?

1:05:00 – How brands should work with creators

1:15:00 – Wrap up & final thoughts

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Follow our hosts:

Nick Shackelford

Twitter/X: https://x.com/iamshackelford

LinkedIn: https://www.linkedin.com/in/nickshackelford/

Instagram: https://www.instagram.com/iamnickshackelford/

Zoe Kahn

Instagram: https://www.instagram.com/_zoekahn_/

LinkedIn: https://www.linkedin.com/in/zoe-kahn-5b61aa129/

Twitter/X: https://x.com/_zoekahn_

YouTube: @ZoeKahn

Bart Szaniewski

Instagram: https://www.instagram.com/theszef/

LinkedIn: https://www.linkedin.com/in/bart-szaniewski-374b1141/

Twitter/X: https://x.com/TheSzef

John Coyle

YouTube: @johnjhcoyle

Twitter/X: https://x.com/johnjhcoyle

Instagram: https://www.instagram.com/johnjhcoyle/

LinkedIn: https://www.linkedin.com/in/john-coyle-1bb231120/

📩 Business inquiries: john@coyle-enterprises.com