The Checkout

Modern Commerce Media
  • 0.0 (0)
  • MARKETING
  • UPDATED WEEKLY

If you could start a company with anybody in the world, you would want it to be with the co-hosts of The Checkout.

  1. JAN 16

    The New Way to Run Meta Ads in 2026

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... Meta ads are still working, but most brands are making them way harder than they need to be. In this episode of The Checkout Podcast, we go pure tactical on Meta Ads: what’s working right now, how to test creatives without blowing up your account, and why most people obsess over “structure” when the real game is decision-making and creative systems. We break down the real fork in the road that every brand and media buyer has to choose: Do you dedicate spend to every creative test? OR Do you drop new creatives into proven campaigns and let Meta pick winners? Whether you’re running Advantage+, scaling a brand past 7-figures, or stuck in the cycle of constantly tweaking things out of paranoia, this episode will give you a clearer framework to make decisions with confidence. ⸻ What You’ll Learn In This Episode • Meta ads in 2026: what’s actually changing and what’s not • The two testing philosophies that control everything in your ad account • When testing everything will tank performance (and when it helps you scale) • Why most brands are overcomplicating campaign structure • How to know if your tactics are outdated without ruining what already works • How to find winning ad angles faster than ever (even if you feel stuck) • The 50/30/20 creative framework (internally proven → outside inspired → outside-the-box) • How top brands stay consistent while still finding new winners

    1h 21m

  2. JAN 8

    What Actually Fuels Most Founders (And Why Most Quit)

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... Why Most Founders Fail — And How to Avoid the Same Mistakes In this episode, we break down why the vast majority of founders and small businesses fail—and more importantly, how to avoid becoming another statistic. John Coyle (VP of Marketing at Royo Bread), Nick Shackelford (Partner at Brez) and Bart (Co-Founder of Dad Gang) answer real questions submitted by listeners and share hard-earned lessons from building, scaling, and surviving multiple businesses across e-commerce, agencies, SaaS, and brand building . This is not surface-level motivation. It’s a deep, honest conversation about choosing the right business, building leverage, avoiding burnout, selecting co-founders, and understanding what actually fuels long-term success. ⸻ Topics Covered in This Episode How do you choose the right business to start? We break down why most people fail before they even begin—often by choosing ideas without skills, leverage, or real-world exposure. The group explains why working for the right company or starting a “boring” business can be the smartest move early on. Why most founders burn out (even after they “win”) Burnout doesn’t always come from losing—it often comes after success. The hosts share personal burnout stories, including moments where they physically couldn’t bring themselves to work, even after major financial wins. The real role of passion vs. skill Passion alone isn’t enough. This episode explains how to pair what you care about with what you’re actually good at—and how ignoring that balance leads to frustration and failure. Solo founder vs. co-founder: what actually works We dive deep into: • When you should start solo • When a co-founder becomes necessary • Why complementary skills matter more than equal skills • How poor alignment destroys otherwise great businesses How to find the right co-founder From moral alignment and trust to lane separation and incentives, this episode outlines what healthy partnerships actually look like—and why most people rush into the wrong ones. Why you shouldn’t try to learn everything at once Trying to master fulfillment and sales and marketing at the same time is one of the fastest paths to failure. The conversation breaks down how to simplify early and build leverage instead. Founder motivation & infinite fuel sources One of the most powerful parts of the episode: the idea that burnout happens when you’re running on the wrong fuel. Learn how to identify what truly motivates you—and how to design your work around it. Female founders in male-dominated industries We tackle a tough but important question: are female founders losing deals because of gender bias? And if so, how can that be turned into a strategic advantage rather than a disadvantage? ⸻ Who This Episode Is For • First-time founders trying to choose the right business • Agency owners stuck at six figures and feeling maxed out • Solo founders debating whether to bring on a partner • Entrepreneurs dealing with burnout, loss of motivation, or stagnation • Anyone trying to build a business that supports life—not consumes it ⸻ 🎧 Why You Should Watch the Full Episode This conversation is raw, unscripted, and grounded in real operator experience—not theory. If you’re serious about building something that lasts, this episode will help you: • Avoid common early-stage traps • Make better long-term decisions • Understand yourself as a founder • Build businesses that align with your values and energy

    1h 11m

  3. JAN 2

    Overstaffed, Underprofitable: How Founders Should Think About Hiring

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... Growing fast should feel like winning. So why do so many founders end up more stressed, less profitable, and questioning their own decisions as revenue climbs? In this episode, we break down one of the most uncomfortable but critical questions founders face as they scale: Are you actually building a better business — or just hiring your way into chaos? The conversation starts with a real founder scenario: • Revenue is up 200% year over year • The company used to be profitable • Now it’s losing money • The team’s solution? Hire more people From there, we unpack what’s really happening beneath the surface. This episode covers: • The hidden danger of overhiring during growth • Why “we need more people” is often a symptom, not a solution • How to tell if a role is actually contributing to revenue or profit • The difference between scaling output vs scaling overhead • When losing money can make sense — and when it absolutely doesn’t • Why chasing top-line growth can quietly destroy founder clarity and decision-making • The mental and financial cost of “speedrunning” to $100M • How experienced operators think about stress, risk, and sustainability • Practical frameworks for hiring lean without stalling growth You’ll also hear candid takes on: • The myth that bigger teams automatically mean better execution • Why many brands hit a wall around certain revenue milestones • How to think about hiring when you’re not a multi-time operator • The difference between scaling with confidence vs scaling in survival mode This is not a hype episode. It’s a reality check for founders who are growing fast and wondering if the pressure they feel is normal—or a warning sign. If you’re a founder, operator, or growth lead asking yourself: • “Should I slow down?” • “Did I overhire?” • “Am I building something sustainable—or just expensive?” This episode will help you think more clearly about what comes next.

    1h 11m

  4. 12/25/2025

    Why Founders Are Afraid to Stop Working

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... 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.

    1h 24m

  5. 12/18/2025

    The Most Valuable Marketing Conversation You’ll Watch in 2026

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... 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.

    1h 40m

  6. 12/11/2025

    $1M vs $100M Business Problems: How To Properly Scale

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/post-purchase-checklist 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.

    1h 18m

  7. 12/02/2025

    How To Sell to 9 Figure Brands

    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. --- 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

    1h 22m

  8. 05/28/2025

    Are Entrepreneurs More ADHD?

    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

    1h 18m
See All (19)

About

If you could start a company with anybody in the world, you would want it to be with the co-hosts of The Checkout.

Information

  • Creator
    Modern Commerce Media
  • Years Active
    2025 - 2026
  • Episodes
    19
  • Rating
    Explicit