The Checkout

Modern Commerce Media

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. HACE 5 DÍAS

    He Built DigitalMarketer. Here's How He'd Scale Any E-Commerce Brand — Ryan Deiss

    Book a call with John: https://www.thedivenewsletter.com/squeeze-page1712742970440 Wondering why you're more buried in work than you were a year and a million dollars ago? You hired helpers. Not operators. Ryan Deiss founded DigitalMarketer.com, trained 120,000 marketers, and now runs 17 companies doing $250M+ a year. In this episode, he walks through how he'd actually scale any brand from $1M to $30M+ — from the hire that unlocks scale to the three engines that power e-commerce businesses. Topics discussed: 00:00 - Introduction 00:48 - Does EOS work in e-commerce? 08:13 - The worst stage of any business 09:09 - 3 engines every e-com brand runs on 21:42 - Mapping your business for scale 26:01 - Scaling without losing time with your family 36:00 - Why founders never feel like they’re making enough 40:50 - Identity shifts as you scale 48:17 - The first role to hand off (and one you shouldn’t) 57:23 - How to hire for an undefined role 01:01:54 - What to focus on at each stage of growth 01:10:37 - Should you scale, sell, or raise at $30M? 01:17:44 - Do lead magnets work in e-commerce? Learn more about our sponsors: https://www.attentive.com/ https://fuego.io/ https://www.socialsnowball.io/ https://redo.com/ 🔗 CONNECT WITH RYAN DEISS: Instagram @ryandeiss YouTube @ryandeissofficial X @ryandeiss Website : https://scalable.co/ LinkedIn:https://www.linkedin.com/in/ryandeiss/ Free Book Get Scalable: https://www.getscalable.com/ 🔗 CONNECT WITH JOHN: https://www.linkedin.com/in/john-coyle-1bb231120/ https://www.tiktok.com/@johnjhcoyle 🔗 CONNECT WITH BART : https://szaniewski.com/ https://www.instagram.com/theszef/ https://www.linkedin.com/in/bart-szaniewski-374b1141/

    1 h 30 min
  2. 30 ABR

    How E-Commerce Brands Can Crush UGC in 2026 — Josh Suggs

    Book a call with John: https://www.thedivenewsletter.com/squeeze-page1712742970440 Most of the e-commerce industry has written UGC off in 2026. Here’s why you shouldn’t. In this episode, StreetTalk founder Josh Suggs breaks down the one content format outperforming everything else in e-commerce ad accounts: street interviews. He shares where it fits in your media mix at every budget level, why the brands trying to do this in-house keep failing, and his formula that converts customers in just 40 seconds. If you're running paid ads in 2026 and haven't tested this yet, you're leaving revenue on the table. Topics discussed: 00:00 - Introduction 01:17 - StreetTalk’s origin story 07:53 - How they scaled so fast 17:41 - The early hustle 21:21 - Leveraging your way to success 27:09 - The business move that failed 33:02 - How Expo West changed the business 34:16 - The street interview formula 38:12 - Why street interviews convert so well 39:55 - Making money as a StreetTalker 42:18 - Why street interviews belong in your ad account 43:29 - How to allocate a $5–$10K content budget 47:42 - Why brands struggle to replicate this in-house 50:28 - Street interview concepts for real products 59:45 - Creating a show around your brand Learn more about our sponsors: https://www.attentive.com/ https://fuego.io/ https://www.socialsnowball.io/ https://redo.com/ 🔗 CONNECT WITH JOSH SUGGS: https://www.streettalk.com/ https://x.com/joshsuggss https://www.instagram.com/joshsuggss/ https://www.instagram.com/streettalk/ 🔗 CONNECT WITH JOHN: https://www.linkedin.com/in/john-coyle-1bb231120/ https://www.tiktok.com/@johnjhcoyle 🔗 CONNECT WITH BART : https://szaniewski.com/ https://www.instagram.com/theszef/ https://www.linkedin.com/in/bart-szaniewski-374b1141/

    1 h 9 min
  3. 23 ABR

    What $100M E-Commerce Brands Know That The Others Don’t — Nik Sharma

    Book a call with John: https://www.thedivenewsletter.com/squeeze-page1712742970440 Stuck between $2M and $30M and asking yourself, "What are the big brands doing that I'm not?" Nik Sharma worked with $100M brands like True Classic, Jolie and Eight Sleep, and he knows why most brands stall before they ever get close. In this episode, he breaks down exactly what the brands that speed-run to $100M do differently and the moves you can make to get unstuck. Topics discussed: 00:00 - Introduction 00:29 - What makes a brand reach $100M in e-commerce 04:15 - Eight Sleep case study: how they got so big 07:58 - Why second-time founders hit $100M faster 12:17 - Budgeting for marketing you can’t track 22:09 - Top vs. bottom of funnel marketing: what most brands get wrong 24:19 - Creating effective advertorials 29:04 - Why some successful brands stall before $100M 43:04 - Five marketing channels that work in e-commerce 46:15 - How to leverage AI without getting distracted 58:53 - Shiny object syndrome and your role as founder 01:01:19 - How to start a new brand with $50,000 01:09:24 - The one factor that differentiates $100M brands 01:13:31 - What most founders don’t know about scaling Learn more about our sponsors: https://www.attentive.com/ https://fuego.io/ https://www.socialsnowball.io/ https://redo.com/ 🔗 CONNECT WITH NIK SHARMA: https://www.nik.co/ https://www.linkedin.com/in/mrniksharma/ https://x.com/mrsharma 🔗 CONNECT WITH JOHN: https://www.linkedin.com/in/john-coyle-1bb231120/ https://www.tiktok.com/@johnjhcoyle 🔗 CONNECT WITH BART : https://szaniewski.com/ https://www.instagram.com/theszef/ https://www.linkedin.com/in/bart-szaniewski-374b1141/

    1 h 28 min
  4. 16 ABR

    How to Build a Personal Brand That Actually Sells Product (For E-Commerce Founders) — Kev Michael

    Book a call with John: https://www.thedivenewsletter.com/squeeze-page1712742970440 You're not an influencer. You're not famous. You started a business to sell a product. So how does a personal brand actually help you? In this episode, podcast growth expert Kev Michael breaks down exactly how a personal brand drives sales without turning you into a full-time content creator. You'll learn the #1 mistake e-commerce founders make when building a personal brand, the content that outperforms almost all other ads, and the paid strategy most brands are still wasting money on. Stay for the live workshop of real e-commerce brands to see step-by-step how to build show concepts from scratch no matter what you sell. Topics discussed: 00:00 - Introduction 01:44 - What most founders get wrong about “personal brand” 07:22 - Can you build a YouTube channel or podcast with a small team? 08:13 - The paid ad strategy that actually works 13:20 - The ROI of podcasting and finding your show's premise 18:45 - How to build your from scratch (a real-time case study) 31:39 - How to stand apart from other channels33:30 - Why it's hard for some brands to find their audience 42:35 - Workshopping the DadGang podcast 51:51 - Do you need to publish weekly? 59:41 - The 3 waves of podcasting ROI 01:02:42 - When to give up or change your strategy Learn more about our sponsors: https://www.attentive.com/ https://fuego.io/ https://www.socialsnowball.io/ https://redo.com/ 🔗 CONNECT WITH JOHN: https://www.linkedin.com/in/john-coyle-1bb231120/ https://www.tiktok.com/@johnjhcoyle 🔗 CONNECT WITH BART : https://szaniewski.com/ https://www.instagram.com/theszef/ https://www.linkedin.com/in/bart-szaniewski-374b1141/

    1 h 10 min
  5. 20 FEB

    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
  6. 20 FEB

    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
  7. 5 FEB

    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

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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.