Today we talk about ADHD in entrepreneurship and other neurospicyness. We also discuss everything we learned in season one of The Checkout.

Zoe and John close out Season 1 with a chaotic, thoughtful, and very human conversation on where eCom is headed, what it takes to build a resonant brand today, and why everyone on the internet is a little bit NeuroSpicy.

This Episode:

In our final episode of the season, it’s just Zoe and John—and somehow they cover everything:

What brands got right (and wrong) about the tariff panic

When to prep for disaster vs. stay the course

How founders use luck, instinct, and hindsight to survive

Talking to your customers (for real, on the phone)

The new blueprint for brands: act like a creator, feel like a friend

Rethinking influencer deals and creator monetization

ADHD, medication, and creativity

The Jackie origin story

Why John talks so damn much

Season reflections + what's coming next

→ Drop a comment: What made The Checkout feel different from every other eCom podcast? We’re reading them all—and building Season 2 around what you say.

Sponsors:

Marpipe – https://www.marpipe.com/

Heatmap.com – https://www.heatmap.com/

Chapters:

00:00 – Intro & why it's just John and Zoe

05:00 – Big takeaways from the year in eCom

11:00 – Preparing vs. reacting: smart founder strategy

18:00 – Tariff fallout and brand-level decision-making

25:00 – Customer calls, brand resonance, and content as connection

33:00 – Brands acting like creators & building vibe-based community

41:00 – Influencer monetization & new deal structures

49:00 – Listener comments, ADHD, and creative trade-offs

1:04:00 – Jackie lore, internal ops, and life structure

1:12:00 – Season reflections, muskrat jokes & what’s next

Follow Our Hosts:

John Coyle

YouTube: https://www.youtube.com/@johnjhcoyle

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

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

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

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/zoekahn/

Bart Szaniewski

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

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

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

A 145% tariff isn’t just a price hike—it’s a slow-motion business killer.

This Hidden E-commerce Giant Makes BILLIONS In Plain Sight

John recently got fired from his job. We reflect on whose fault it was, plus tell stories about losing jobs.

Today we're chatting layoffs, copywriting breakthroughs, and why the top 10% of spenders might be your only real customers.

We kick things off with a brutally honest conversation about getting fired—how it feels, what it means, and why it might actually be your fault. Then Bart drops a VC-backed horror story, and Nate Lagos (VP Marketing @ Original Grain) helps us reframe the whole conversation. From there, we dive into copywriting tactics, Meta ad strategy, channel fatigue, and why it might be time to stop building brands for everyone.

In this episode:

The guilt spiral of getting let go—and the reality check you might need

Why shame and blame don’t help (but taking responsibility does)

The underrated power of your personal network and digital footprint

How Nate’s team uses website copy to test Meta ads more effectively

Why most brands chasing shiny new channels are wasting time

The case for building brands specifically for the top 10% of earners

Scarcity, storytelling, and the psychology of premium pricing

Deep cuts from brands like Kith, Supreme, Represent, and Carved

💬 Comment below:

What’s the best (or worst) thing that happened to you after getting fired?

📣 Sponsors:

https://www.marpipe.com

https://www.heatmap.com

⏱ Chapters:

00:00 – Getting fired: is it ever not your fault?

08:30 – Bart’s horror story VC layoff

18:45 – Blame, shame, and bouncing back

26:30 – The real reason your network matters

34:30 – Why Meta still works (and how to make it work harder)

43:00 – Why most brands should not chase new channels

59:14 – Selling to the top 10%: product, perception, price

01:10:50 – Examples from Kith, Supreme, Represent & more

01:20:55 – Grand Ole Opry collab + closing thoughts

🎙 Follow Our Hosts:

Nick Shackelford

https://x.com/iamshackelford

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

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

Zoe Kahn

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

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

https://x.com/_zoekahn_

https://www.youtube.com/@ZoeKahn

Bart Szaniewski

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

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

https://x.com/TheSzef

John Coyle

https://www.youtube.com/@johnjhcoyle

https://x.com/johnjhcoyle

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

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

Nate Lagos

https://x.com/natelagos

https://www.linkedin.com/in/natelagos/

https://open.spotify.com/show/5nULM2GckoiJp7rri3kYt1?si=91ca1f50a35d4656

Today on the checkout we're talking about Post Malone reaching out to work with one of co-hosts brands and the secret "guy behind the guy" who has build Post Malone's empire into an Empire. We also talk about:

How to do -celebrity and influencer collabs

How to build product and personal brand identity.

The offers by Amazon and OF to buy TikTok

Getting professionally catfished

AI ad hype die down

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Chat GPT Prompt for Your Personal Action Figure:

Step 1. Enter a Text Prompt for Your AI Action Figure

Use a template provided, such as:

"Create an image of an action figure in packaging labeled '[Your Label]'. Use the attached photo as a reference for the face. [He/She] is [Height] tall and dressed in [Outfit Description], and holding [Item, e.g., Coffee Mug]. The cardboard section should be [Color]. Include an 'Accessories' section with items like [List Accessories]. Make the design visually appealing and reflective of a [Describe Industry]. Do not include the character image on packaging." This ensures detailed, industry-specific results.

Step 2. Upload a Reference Image for Your AI Action Figure

Upload a clear photo, as ChatGPT uses facial recognition for accuracy.

---

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: https://www.youtube.com/@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: https://www.youtube.com/@johnjhcoyle

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

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

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

For business inquiries reach out to [email protected]

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00:00 Post Malone + Intro

03:59 The Guy Behind Post Malone

08:40 How To Do Celebrity Collabs

16:45 Product Identity

28:57 Personal Action Figures

32:52 Amazon (or OF) to Buy TikTok?

41:09 Professional catfishing

48:56 AI ad hype die down

1:03:38 All of our action figures

Kim Kardashian is teaming up with Nike with her brand, Skims. We give our takes on this, plus Poppy’s influencer vending machine backlash. From marketing moves to funding philosophies, we’re breaking down what works, what’s overhyped, and what smaller brands can learn from the biggest names in the game.

- Kim Kardashian partners with Nike — genius move or gimmick?

- Why Nike needed this… and why Skims might not have

- What made Poppy’s influencer stunt controversial?

- Was Olipop’s response petty or perfect?

- The rise of Diet Coke as a (maybe satirical?) fitness brand

- Bart’s insane 740-pound marlin fishing story (yep, really)

- Should physical product brands ever raise money?

- The trap of reporting to investors—and when raising might make sense

👇 Subscribe & drop a comment

Think we’re wrong about raising money? Make the bull case in the comments.

Check Out Our Sponsors

Marpipe – The only AI ad platform that actually makes sense for creative teams: https://www.marpipe.com

Heatmap.com – Your site’s silent sales coach. Instantly see what’s working (and what isn’t): https://www.heatmap.com

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: https://www.youtube.com/@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: https://www.youtube.com/@johnjhcoyle

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

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

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

Chapters

00:00 – Whatup - let's talk Kim Kardashian x Skims

10:00 – Nike x Skims: who really wins

30:00 – Poppy’s PR stunt & influencer backlash

50:00 – Coke goes prebiotic & Diet Coke gets weird

1:10:00 – Fishing stories & big flexes

1:20:00 – Raising money: smart move or trap?

For business inquiries reach out to [email protected]

If you're not selling something to people while they’re out living life… what are you even doing?

In this episode of The Checkout, John, Zoe, and Bart dive into how brands can break out of the DTC echo chamber and actually stand out—through physical experiences, creative retail, and lo-fi entertainment. From coffee shops with sandboxes to vending machines in front yards, we explore all the ways brands can drive sales outside of Meta ads.

We talk:

💼 Sponsors of This Episode:

Marpipe – Multivariate ad testing made simple. Automate creative testing and scale what works. https://www.marpipe.com

Heatmap.com – Know exactly where users click, scroll, and drop off. Visual analytics that help you optimize conversion. https://www.heatmap.com

⏱️ Chapters:

00:00 – Intro: Coffee shops, sandboxes, and dad RC culture

05:00 – Building brands through experiential retail

12:30 – Creative ways to get into physical retail

20:00 – Innovation vs. repositioning in DTC

35:30 – Social shows and customer-based content

45:00 – Marketing ideas that come from thinking

55:00 – When vacation = better ideation

1:10:00 – Wrap-up: Lazy marketing vs. original thinking

👀 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: https://www.youtube.com/@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: https://www.youtube.com/@johnjhcoyle

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

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

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

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: [email protected]

Today we're talking about how some businesses can make you a lot of money while others can make you rich, but almost none of them will get you both.

⚡ Subscribe for more eCommerce insights, brand breakdowns, and unfiltered takes!

📢 Follow us on social media:

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: [email protected]

Chapters

00:00:00 You can get rich or make money

00:30 Long term business vs money grab

00:10:09 Guest Appearance from the Fidget Spinner King

00:20:00 When to go full-time in your business

00:28:20 Product expansion

00:54:00 Hard working belts

01:07:40 Products as Marketing

01:10:49 Bye