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PODCAST

Underdog Ecom Podcast

Jack Oswald & David Lindahl

🚀 Welcome to the Underdog Ecom Podcast—the raw, unfiltered podcast for ecommerce founders actually in the trenches. Tired of the same 9-figure guru success stories? We’re talking real highs, lows, and struggles of running an underdog ecommerce brand—from cash flow crunches to ad meltdowns and everything in between. 🔥 What You’ll Get: - Honest conversations about building a brand without venture capital. - What’s working (and what’s not) in DTC, Amazon, and wholesale. - The latest industry shifts

business marketing

All Episodes

33:54

Our Ecom Origin Stories

Underdog Ecom Podcast ·

2025/04/14

From pro tennis tours to Pacific Northwest pop-ups—Jack and David share how they stumbled into the world of e-commerce and built their brands from scratch. In this episode, they dive into the unexpected twists, early mistakes, and the wins that shaped their journeys, all while keeping it real about what it actually takes to build something from nothing.📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite podcast platform and share it with fellow ecom founders! Your

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38:38

All About Wholesale-B2B

Underdog Ecom Podcast ·

2025/04/03

In this episode, Jack picks David’s brain on all things B2B and wholesale—from getting stocked in REI and airport gift shops to building a Shopify-powered wholesale channel from scratch. They dive into tools like Faire, SparkLayer, and Trunk, discuss margins, outreach tactics, and what makes wholesale a viable (and sometimes brutal) growth lever for DTC brands. Plus, a quick detour into how new AI tools are shaking up creative workflows and initial ecom community reactions. 📢 Enjoyed the

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34:47

Mystery Boxes & Kickstarters

Underdog Ecom Podcast ·

2025/03/27

In this one, David breaks down how he pulled off a mystery box sale to move excess inventory—VA hacks, ops chaos, and way better ROAS than expected. Jack’s deep in stockouts throughout a sale, wrestling with whether to open up pre-orders… We get into the real trade-offs of crowdfunding, cash flow pressure, and why sometimes it’s better to just wait—even when customers are begging to buy.📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite podcast platform and share

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35:13

More Fixed Costs

Underdog Ecom Podcast ·

2025/03/20

In this episode, we open up about the very real challenges of juggling fixed costs — from surprise fulfillment bills and tariff headaches to stacking revenue-based loans. We discuss how we’re purging unnecessary apps, negotiating SaaS pricing, and finding creative ways to turn fixed costs into opportunities. If you’re navigating tight margins and trying to stretch every dollar, this one’s for you.📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite podcast platform

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41:59

How We Use AI

Underdog Ecom Podcast ·

2025/03/14

This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.This week, we (David & Jack) are getting real about the challenges we’re facing right now in our businesses—along with some cool experiments we’ve tried (fundraiser, anyone?). Plus, we’re sharing practical insights on AI from the perspective of two underdog operators.If you're a team

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63:49

The Great App Purge

Underdog Ecom Podcast ·

2025/03/05

This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.In true Underdog Ecom style, we’re diving deep into the Shopify apps we’re paying for—what’s worth it, what’s not, and how much we’re actually spending. No app shilling here—just two operators figuring out how to cut the bloat and grow more profitably.If you’re looking to trim unnecessary

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11:25

Underdog Ecom Podcast Introduction

Underdog Ecom Podcast ·

2025/03/05

This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.In this first episode, we (Jack & David) introduce ourselves, why we started this podcast, and what you can expect. Spoiler: We’re keeping it raw, unfiltered, and packed with actual insights—not just success stories.If you’re tired of the “get rich quick” ecom content and want to hear

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