In this episode, we dive into the grueling reality of in-person selling, from the logistical nightmares of managing physical inventory to the high-stakes gamble of paying event fees. We share our honest stories about finding success at niche night markets while facing disappointing "busts" at massive events like the State Fair and Wimbledon. Ultimately, we discuss why in-person events are a powerful feedback loop for brand building, even if the high opportunity cost often keeps us focused on the digital side of the business.

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We’re peeling back the curtain on our operations to reveal the 50+ Shopify Flows we use to run our brands on autopilot . From catching high-risk fraud and filtering out bot traffic to deleting expensive pre-order apps, we break down the exact automations saving us time and money . Tune in to hear how we’re hacking the system—and why you might be running “zombie” flows that are secretly slowing down your store .

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Thanks for listening! Leave a review on your favorite podcast platform and share it with fellow ecom founders! Your support helps us keep it real.

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Website: https://underdogecom.com Podcast: https://podcast.underdogecom.com

We’re kicking off 2026 by dissecting the good, the bad, and the ugly of last year, from the reality of prioritizing profitability to our struggles with organic content and wholesale. We also break down our specific resolutions for the year ahead, including strategies for tighter product launch cycles, clearing dead stock through bundling, and managing cash flow without revenue-based loans.

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In this episode, we tackle our first live "SaaS unboxing" to review Eltie, a new AI email platform that promises to build revenue-ready calendars tailored to your brand. We test the tool in real time, exploring its ability to generate HTML emails and product images, while debating whether AI tools can ever truly replace human agencies. Join us as we break down the pros and cons of the platform's Klaviyo integration and decide if it’s worth the investment for small teams.

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As we wrap up the year, we sat down to break down the highs, lows, and hard truths from a chaotic ride in ecom—shifting social platforms, product flops, and what actually moved the needle. Plus: what we’re doubling down on in 2026 and why “newness” might be your biggest growth lever next year.

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We survived Black Friday… and somehow had our best months ever. In this one, we break down what worked, what we totally screwed up (like accidentally turning off pop-ups), and how we pulled off big wins with scrappy offers, mystery boxes, and way too many emails. If you're already dreading next Q4, this one's for you.

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Ecom operator and founder Toby joins Jack and David for our very first guest episode—across three continents, no less. From running a golf brand and a baby brand with his wife to working full-time at a global DTC company, Toby unpacks the chaos of juggling it all. Real talk on scaling with limited time, why ops might be the real superpower, and why Meta spend doesn’t always scale like you think it should.

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We’re deep in Q4 chaos—scrambling for sales, cash-strapped, and trying everything we can to keep things moving. In this episode, we talk about our creative last-ditch fire sale offers, how we’re leaning on virtual assistants to keep our heads above water, and what’s actually been working (and not) as we prep for BFCM. Whether you’re thinking about hiring a VA or already working with one, we break down what tasks are worth outsourcing, what hasn’t worked, and how to build a scrappy support system that helps—not hinders.

📢 Enjoyed the episode?

Thanks for listening! Leave a review on your favorite podcast platform and share it with fellow ecom founders! Your support helps us keep it real.

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🌎 Join the Underdog Ecom Community:
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🎧 More from Underdog Ecom:
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Podcast: https://podcast.underdogecom.com