The Checkout

Modern Commerce Media
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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. 5D AGO

    8-Figure Founders Share EXACTLY What They Would Do If They Had to Restart Tomorrow [Bad Audio - Sorry]

    Sorry for the bad audio, we considered not publishing, but ultimately decided the episode was value packed so we went ahead and published it. Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... What would successful founders actually do if they lost everything tomorrow? In this episode, a room full of 7- and 8-figure business owners breaks down — honestly and tactically — how they would rebuild from zero if their money, skills, network, and businesses disappeared overnight. This isn’t theory. It’s real-world thinking from operators who’ve already built and scaled multiple companies. The conversation covers the exact skills worth learning today, how to accelerate success early in your career, and why network, reps, and timing matter more than most people realize. You’ll hear practical frameworks for rebuilding wealth, choosing the right opportunities, and positioning yourself to win — even starting with nothing. ⸻ 🔥 What You’ll Learn In This Episode ✅ The fastest path back to success if you had to start over ✅ Why skill acquisition beats chasing business ideas early on ✅ The role mentorship, jobs, and environment play in accelerating growth ✅ How networking creates opportunities when everything else fails ✅ The smartest next move after selling a business (but not retiring) ✅ Why consulting can be the ideal transition after an exit ✅ How AI and emerging technologies create new leverage today ✅ Modern Meta ads strategy if organic growth didn’t exist ✅ Dropshipping, lead generation, and validation-first business models ✅ The mindset shift required to rebuild momentum from zero ⸻ 💡 Key Takeaways • Early careers should focus on skills and reps, not status. • Keeping overhead low gives entrepreneurs more “shots on goal.” • Strong relationships often matter more than tactics when rebuilding. • Consulting and community-driven businesses can create clarity after exits. • Cultural shifts — especially AI — create massive opportunity for those willing to immerse early. The episode also dives into real tactical discussions around SMS marketing changes from Apple’s new messaging filters and how brands can adapt to maintain deliverability and engagement.  ⸻ If you’re an entrepreneur, operator, creator, or aspiring founder trying to figure out your next move — this episode is packed with high-signal advice from people who’ve already done it. 👉 Watch until the end for rapid-fire answers on business models, marketing strategies, and unconventional opportunities founders are quietly exploring today.

    57 min

  2. 5D AGO

    From 10 Ads a Week to 60 | Scaling Creative the Smart Way

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... You’re not out of ideas — you’re out of creative systems. In this episode, we break down one of the biggest bottlenecks holding brands back: scaling creative when the founder is doing everything themselves. From shooting ads, editing videos, and generating ideas to managing production — many founders become the constraint in their own growth. So how do you scale creative output without hiring a massive team or increasing overhead? We sit down to solve this problem in real time and walk through practical strategies to help founders produce more ads, unlock new angles, and build repeatable creative systems. You’ll learn how to turn your community into a content engine, build scalable social content formats, use AI to multiply assets, and increase output without long-term hiring commitments. If you run a brand, manage paid ads, or create content at scale — this episode shows how to increase creative volume without burning out. ⸻ What You’ll Learn ✅ How founders accidentally become the bottleneck in creative production ✅ How to scale ad output without hiring full-time employees ✅ Why community-driven content is an unfair advantage ✅ How to crowdsource ideas and content from customers ✅ The best formats for repeatable social content ✅ Ways to generate 50–60 creative assets per month ✅ How to use AI workflows to multiply static ads into dozens of variations ✅ When to use freelancers vs. full-time hires ✅ How to build ongoing “social show” formats that drive growth ✅ Systems for increasing creative volume before major scaling periods (like Q4) ⸻ Key Topics Covered • Scaling creative with low overhead • Founder-led marketing vs. team-based production • Community-led brand building • Creative ideation frameworks • Format-based content strategy • AI tools and automation workflows • Static ad amplification strategies • Creative testing and volume strategy • Building repeatable content engines ⸻ Who This Episode Is For • DTC founders and operators • Performance marketers and media buyers • Creative strategists and editors • Agencies scaling ad production • Brands preparing to scale paid spend • Anyone producing ads or content at scale ⸻ About the Show This podcast breaks down real growth challenges from operators, founders, and marketers — and solves them live. Each episode focuses on practical strategies for scaling brands, improving marketing systems, and increasing performance through better creative and execution. Subscribe for more conversations on creative strategy, DTC growth, performance marketing, and brand building.

    23 min

  3. FEB 5

    Why Most Brands Panic During Slowdowns (And What to Do Instead)

    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 your brand is growing fast… and then suddenly hits a wall? In this episode, we break down a real-time business speed run where a fast-growing consumer brand faces stalled momentum caused by inventory constraints, pricing issues, and misaligned incentives. Instead of panic decisions—cutting spend, freezing growth, or randomly changing strategies—we walk through exactly how to reset momentum intelligently. You’ll learn: • Why most brands panic during slowdowns (and why that usually makes things worse) • How to think about growth when you’re supply constrained • The right way to pre-sell offers without blowing up trust or margins • How to raise prices without killing demand • Why “cracked offers” can secretly destroy profitability • How to realign teams when growth pauses • The difference between optimizing vs accelerating • How to bottle demand so you can release it later at scale • What to focus on when paid ads aren’t an option • How to create a momentum shift in as little as 20 minutes This conversation is especially valuable for: • E-commerce founders • Brand operators • Growth marketers • Performance marketing teams • Anyone scaling subscription or DTC businesses If you’ve ever felt stuck between wanting to grow and being unable to push harder—this episode gives you a clear mental model for what to do next. Watch until the end for the full breakdown of how to fix a stalled brand without panic.

    25 min

  4. JAN 29

    The Exact Ad Channel Mix for Scaling to $100M+

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... How to Scale to $100M+ Without Breaking Your Brand What actually changes when a brand moves from early traction to serious scale? In this episode, we break down the exact questions brands start asking on the road from $0 to $100M+—the questions that separate brands that plateau from brands that keep compounding. We cover: • The exact ad channel mix we’d run when scaling toward $100M+ • When (and how) to introduce brand spend without killing performance • How to scale without losing your core customers • Why most brands hit a ceiling even when revenue is growing • The real tradeoffs between performance vs brand marketing • How fast-growing companies think about team structure, media, and messaging This isn’t theory or generic marketing advice. These are real conversations happening inside 8- and 9-figure brands as they scale. If you’re a founder, operator, or marketer trying to grow past your current ceiling—this episode will change how you think about growth. 🎯 Perfect for: • Founders scaling past 7 figures • Performance marketers managing large budgets • Operators navigating brand vs performance decisions • Anyone building a long-term, defensible brand Chapters: 00:00 – Why scaling breaks most brands 02:41 – The difference between growing revenue vs growing a brand 06:05 – The exact questions brands start asking past 7 figures 10:12 – The $100M mindset shift most founders miss 14:28 – Performance marketing vs brand marketing (what actually changes) 18:47 – The exact ad channel mix for scaling toward $100M+ 23:36 – When to start spending on brand (and how much is too early) 28:14 – How brands lose their core customers while scaling 32:09 – Scaling without killing trust, loyalty, or positioning 36:18 – Team structure, decision-making, and growth bottlenecks 40:41 – Final advice for founders scaling past their current ceiling 44:12 – Subscribe :)

    46 min

  5. JAN 22

    We Built a $1M Brand in 20 Minutes (Copy and Scale)

    Try Attentive: https://www.attentive.com/ Try Fuego: https://fuego.io/ Download Your Free Checklist: https://www.thedivenewsletter.com/pos... We put 20 minutes on the clock and build a $1M business from scratch for a stranger, live and on the spot. In this episode, the “stranger” is the host, and the product is an all-natural meal bar that combines: • 20g of protein • 100mg of caffeine • Sweetened with honey • Built for busy, high-performance people who want energy and fuel in one snack The problem? The founder tried running Meta ads, but after COGS, they were losing money. So in this episode, we break down exactly how we’d take this product from “friends and family sales” to a scalable brand, using a real plan focused on: • Organic-first growth • Boosting content strategically (not just “running ads”) • Subscription framing without killing conversions • Founder-led content and real-world taste test content • Fixing the offer so the unit economics can actually work If you’re building a consumer brand (especially food or supplements) and wondering how to get out of the “I’m spending money but not scaling” trap, this episode is the blueprint. Subscribe if you’re enjoying these breakdowns, because we’re going to keep bringing more real strategies you can apply immediately.

    23 min

  6. 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

  7. 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

  8. 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
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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
    24
  • Rating
    Explicit