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What do you do when you’re doing well… but still feel stuck on the hamster wheel?
In this episode of the podcast, we break down one of the most common (and least talked-about) problems among ambitious operators, founders, and marketers: being constantly busy, financially “okay,” yet unable to make the leap to the next phase of freedom.
The conversation starts with a real listener question — someone working full-time at an agency while trying to build their own brand on the side — and expands into a deep, honest discussion about agency life, risk, ambition, burnout, financial freedom, and the emotional weight of building something meaningful.
We talk about why:
• Agency work is one of the most emotionally draining business models
• Being “busy” is often a sign of misaligned goals, not lack of discipline
• You should feel overwhelmed in certain seasons — and why that’s normal
• Financial freedom and time freedom are not the same thing
• Fear of “losing it all” never fully goes away (and why that’s not a bad thing)
Later in the episode, we shift into a highly tactical discussion around DTC vs retail, cannibalization, and scaling consumer brands the right way — especially for food and beverage companies.
If you’re:
• Working a full-time job while building something on the side
• Running an agency and feeling trapped by client work
• Scaling a DTC brand and considering retail
• Or struggling with the mental load that comes with success
This episode will feel uncomfortably familiar — in a good way.
⸻
TOPICS COVERED
• Agency life vs brand ownership
• When (and when not) to quit your job
• Low overhead as a strategic advantage
• Staying in “the suck” in your 20s
• Financial freedom vs time freedom
• Why fear can be a feature, not a flaw
• Retail cannibalization and blended CAC
• Using DTC to support retail growth
• How great brands actually scale
⸻
WHO THIS EPISODE IS FOR
Founders, operators, marketers, agency owners, and anyone trying to build leverage without burning out — especially if you’re ambitious, capable, and still feel behind.
The Most Valuable Marketing Conversation You’ll Watch in 2026
Thursday, December 18, 2025 • Duration 01:39:49
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In this episode, we bring together four experienced operators, founders, and marketers to answer one deceptively simple question:
What’s the most important marketing advice that actually works today?
No fluff. No theory. Just tactical, real-world insights you can apply immediately—whether you’re launching your first product, scaling a DTC brand, or trying to cut through a louder, more crowded market than ever before.
We cover everything from conversion-rate wins and offer testing, to brand positioning, community-driven growth, and content that doesn’t feel like ads. You’ll hear firsthand lessons from building and scaling consumer brands across e-commerce, CPG, retail, and performance marketing—plus how AI and changing buyer behavior are reshaping the playbook in real time.
What you’ll learn in this episode:
• Why dollar-off offers often outperform percentage discounts (and how to test it properly)
• The real reason most marketing advice fails to convert
• How to think about your second product—and when not to
• Why focusing on one growth channel beats spreading yourself thin
• How brands like Dad Gang built momentum by keeping things painfully simple
• Why community, channels, tools for long-term brand growth
• How to create content that puts the customer at the center, not the product
• What founders are noticing about Google Ads, search decline, and AI disruption
• Why storytelling and real-world community experiences are becoming the most powerful form of marketing
This episode is especially valuable if you:
• Run or are starting a DTC or consumer brand
• Feel overwhelmed by tools, tactics, and “growth hacks”
• Want to build a brand people actually care about—not just click on
• Are trying to adapt to AI-driven changes in search, ads, and discovery
If you’re tired of vague advice and want clear thinking from people actually doing the work, this one’s for you.
I'm Skeptical of the Kim Kardashian x Nike Collab | The Checkout Ep. 06
Wednesday, April 9, 2025 • Duration 01:21:03
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.
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Follow Our Hosts
Nick Shackelford
Twitter/X: https://x.com/iamshackelford
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Zoe Kahn
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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 john@coyle-enterprises.com
Adult Sandboxes & How To Sell More Stuff | The Checkout Ep. 5
Wednesday, April 2, 2025 • Duration 01:11:18
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:
Coffee shops with RC cars (yes, really)
Building marketing channels you own
Retail distribution hacks, from state fairs to local shops
Why marketing isn’t just “make another TikTok”
The rise of "social shows" and customer-based content
Product innovation vs. positioning tricks
Why the best marketers spend time thinking, not just executing
💼 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 First You Have to Be Weird | The Checkout Episode 04
Thursday, March 27, 2025 • Duration 01:23:51
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
-------
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
You Can make Money Or Get Rich, But Not Both | The Checkout Ep. 03
Episode 3
Wednesday, March 19, 2025 • Duration 01:10:50
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: john@coyle-enterprises.com
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
How To Get Celebrities To Use Your Product | The Checkout Ep. 02
Wednesday, March 12, 2025 • Duration 01:11:57
In this episode of The Checkout, we dive into a wild challenge—getting LeBron James to wear a DadGang hat! 🧢💥 Host [Your Name] is joined by DadGang co-founder Bart to brainstorm how to pull off this viral stunt. From designing the perfect hat to leveraging social media for maximum hype, we break down what makes challenge content work and why it could be a game-changer for brands.
We also discuss:
How challenge-based content can drive organic and paid marketing success
The balance between hype and inventory planning in eCommerce
The art of making content that works for both entertainment & advertising
A deep dive into neurodivergence in entrepreneurship (surprise self-discovery moment!)
The wild world of brand projections and why most companies get them totally wrong
This episode is packed with insights, laughs, and some hard truths about growing a brand. Don't forget to like, comment, and subscribe if you love these convos! 🔥💡
⚡ 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: john@coyle-enterprises.com
Chapters:
0:00 - Intro: The LeBron Hat Challenge
2:22 - S/O Marpipe
4:01 - The viral content formula for brands
7:22 - A real lawyer tells us if this is legal
10:46 - How I'd do it
15:29 - S/O Heatmap
16:45 - Sneaky ads
22:44 - What do you do when your numbers aren't hitting
31:53 - When is it the agency's fault?
37:22 - We love Marpipe
39:07 - Customer centric projections
51:47 - We love Heatmap
53:18 - Logistics and customer service vs marketing
59:50 - Neurospicy announcement
1:11:20 - Bye now
Why Are All These Famous Men Starting Alcohol Brands? | The Checkout Ep. 01
Episode 1
Wednesday, March 5, 2025 • Duration 01:24:10
Why do so many famous men have alcohol brands?
Welcome back to The Checkout Podcast, where we break down the latest in eCommerce, brand building, and digital culture—with a little chaos along the way. In this episode, we get into:
💥 Why every famous guy has an alcohol brand (The Rock, Ryan Reynolds, Kevin Hart—what’s the deal?)
💥 The rise of cannabis beverages and new mind-altering brands
💥 AI in eCommerce—will it replace human jobs or just make brands more efficient?
💥 The fraud problem nobody talks about: chargebacks, scams, and fake refunds
💥 Agency drama: When should agencies take credit for a brand's success?
📢 Featuring:
🚀 Zoe Kahn - CEO of The Inevitable Agency, early team member at Ghost & Chomps
👕 Bart Szaniewski - Co-founder of Dad Gang, eCommerce veteran
⚡ Nick Shackelford - Partner and Head of Retention at Brez and a serial entrepreneur
🎤 John Coyle - Typical white guy who talks a lot and thinks others MUST want to hear his opinions.
⚡ 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: 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/
📩 Business inquiries: john@coyle-enterprises.com
Chapters:
00:00 - Welcome to The Checkout Podcast 🎙️
02:15 - Meet the crew: Who’s on today’s episode?
05:45 - Why do all famous men have an alcohol brand?
10:20 - Alcohol, cannabis, and mind-altering brands: What’s next?
14:50 - The LTV advantage of vice brands vs. other categories
18:35 - Why female celebrities lean toward beauty & wellness brands
22:10 - The psychology behind celebrity brand loyalty
27:05 - Can non-celebrities still win in alcohol & beauty?
30:45 - The cannabis beverage boom & market opportunity
36:00 - eCommerce fraud: The problem nobody talks about
41:30 - Chargebacks, customer scams, and fraud prevention tools
45:15 - AI-powered agents in customer service: Game changer or overhyped?
50:55 - The future of AI in marketing & media buying
55:40 - The Vessi agency drama: When should agencies claim credit?
01:02:15 - Do agencies really help brands scale, or just take credit?
01:08:45 - AI’s impact on eCommerce jobs—will it replace humans?
01:15:30 - When AI starts making purchase decisions for consumers
01:21:55 - Could AI change how we buy everything online?
01:28:20 - Final thoughts & wrap-up
$1M vs $100M Business Problems: How To Properly Scale
Thursday, December 11, 2025 • Duration 01:18:20
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Description:
In this episode, John Coyle, Nick Shackelford, and Bart Sinofsky play a game: guessing whether an entrepreneur is running a $1 million or $100 million business based solely on the questions they ask.
The trio dives deep into the specific challenges faced at different stages of growth. They discuss how to curate a "content diet" that actually moves the needle, the myth of juggling multiple businesses successfully, and the "T-shaped" focus required to scale. They also break down how to identify winning products, sharing the origin story of Dad Gang and how to spot "tailwinds" in your own brand.
In This Episode, We Cover:
The "Guru" vs. Operator Dilemma We debate how to distinguish between legitimate advice and "gurus" who make money teaching rather than doing. The hosts break down who to follow for specific skills, including recommendations for Alex Hormozi for general business wisdom, Dara Denney for creative strategy, and Nick Theriot for media buying frameworks. They also discuss why 8-figure founders should eventually stop looking for "hacks" and start hiring specialized consultants.
Mastering Focus: Juggling vs. Deep Work Nick Shackelford explains how he manages five publicly visible companies by building infrastructure and having assistants dedicated to specific areas. In contrast, John Coyle introduces the "T-Shaped" focus theory—the idea that you can only have one "main thing" while other opportunities must serve that main goal. We also share a counter-intuitive productivity hack: using scheduled calls to force "deep work" and block out distractions like Slack.
Identifying Winning Products How do you know if you have a winner? Bart shares the Dad Gang origin story, explaining how selling the first 100 hats to friends and family provided the immediate signal needed to double down. The group also discusses the "Smoke Test" method for testing demand and why you must be a genuine consumer of your own market to find product-market fit.
Solving Business Constraints Why asking "Should I be on TikTok Shop?" is usually a sign of pain or lack of traction elsewhere. John explains the "Biggest Constraint" theory—why you must focus all effort on the single biggest problem in the business—and argues that if you think you have "no big problems," you simply haven't added enough zeros to your revenue goals to break the system.
How To Sell to 9 Figure Brands
Tuesday, December 2, 2025 • Duration 01:22:18
Try Attentive: https://www.attentive.com/
Try Fuego: https://fuego.io/
Download Your Free Post Purchase Checklist: https://www.thedivenewsletter.com/post-purchase-checklist
If you’ve ever wondered how to sell to rich people, enterprise accounts, or fast-growing 8 and 9-figure brands, this episode is the most tactical deep dive you’ll find anywhere.
Today, the guys break down — in brutal honesty — exactly how successful founders and marketing leaders WANT to be sold to… and how most people get it embarrassingly wrong.
Featuring:
• Nick Shackelford — Partner at BREZ, operator behind multiple brands sprinting toward 9 figures
• Bart S — Founder of Dad Gang, leading an 8-figure brand growing fast
• John J Coyle — VP of Marketing at Royo Bread Co, another brand approaching 9 figures
Between them, these operators have worked with dozens of top-tier brands, negotiated with SaaS companies, hired agencies, and reviewed thousands of cold pitches. This episode reveals the real buying psychology behind the curtain.
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What You’ll Learn in This Episode
1. How to Sell to 8–9 Figure Brands (Without Cringe Tactics)
2. Why Founders Buy: Maximizing vs. Optimizing Cycles
3. Cold Emails That Actually Work
4. The ONE Way Every 9-Figure Buyer Starts Their Search
5. How to Run Demos That Actually Close
6. Creative Ways SaaS Companies Close Big Accounts
7. Why Building a Personal Brand Lowers Your SaaS Bill
8. BONUS: How to Scale a $1,000/Month Mobile Pet Grooming Service

⸻
This Episode Is For You If…
• You’re an agency, SaaS founder, service provider, or consultant
• You’re trying to sell bigger clients without sounding desperate
• You want to understand how fast-growing brands actually think
• You want to master cold outreach that doesn’t get instantly deleted
• You want to create offers 8- and 9-figure operators actually buy
⸻
Timestamps
00:00 – Selling to rich people & 9-figure companies
01:30 – Maximizing vs. optimizing (and how to tell the difference)
03:20 – What commoditized offers must do differently
05:40 – How large teams think about time, workload, and demos
07:00 – Bart’s rule: “I only buy what my friends recommend”
10:00 – Cold email teardown: good vs. terrible examples
12:50 – Why founders hate vague SaaS positioning
14:50 – The dating analogy: why trust beats all outreach
17:30 – How to network with high-level operators
19:00 – Why personal brands give operational leverage
22:00 – Going upmarket: the REAL path (not what gurus tell you)
23:30 – What happens on demos that lose deals
25:40 – How founders think about switching costs
28:00 – Creative SaaS deal structures you’ve never seen
30:00 – The ONE thing bigger than any SaaS discount
32:00 – Why some brands choose one platform for everything
35:00 – Listener question: scaling a luxury pet grooming business
40:00 – Packaging convenience, service, and premium positioning
41:45 – Referral loops, add-ons, and retention mechanics
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