Jack Oswald & David Lindahl
Underdog Ecom Podcast
🚀 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 - No fluff, no filters—just real talk from founders figuring it out in real-time.💡 Whether you’re st...
Author
Jack Oswald & David Lindahl
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
Collabs 01.07.2025 39:39
This week, we dive deep into the power of collabs—brand, creator, and retail—and how they can drive growth without relying solely on paid ads. From custom merch drops to brand partnerships, they unpack their own wins, misses, and lessons learned trying to make collabs actually work. 📢 Enjoyed the episode? Thanks for listening! Leave a review on your favorite podcast platform and share it with fel...
Email Marketing 23.06.2025 28:31
Jack and David pull back the curtain on how they actually use email marketing inside their brands—what's working, what's not, and all the stuff they’ve stopped wasting time on. From flows and pop-ups to why copy matters more than design, it’s a real convo about figuring email out without overcomplicating it. 📢 Enjoyed the episode? Thanks for listening! Leave a review on your favorite podcast plat...
Cliffs and Cashflow 11.06.2025 31:58
In this episode, Jack and David dive into the financial ups and downs of running an ecom brand — from battling cash flow crunches and navigating debt traps to rethinking channel dependencies like wholesale. David shares his candid story of turning things around with a strategic line of credit, while both hosts explore emerging traffic sources and the real potential (and pitfalls) of TikTok Shop an...
Bid Caps in Meta Ads? 04.06.2025 26:30
In this episode, we dive into our recent experiments with Facebook bid caps—what’s working, what’s not, and all the frustrating in-betweens. From campaign structures to profitability tradeoffs and whether small brands like ours can really thrive with cost-controlled ad strategies, we break down what it’s really like trying to make Meta ads work when every dollar counts. 📢 Enjoyed the episode? Tha...
Shipping: In-House vs 3PL 28.05.2025 44:02
In Episode 12, Jack and David dive deep into the gritty reality of shipping—comparing in-house fulfillment vs. 3PLs. They unpack their personal setups, the hidden costs, control trade-offs, horror stories, and why neither path is as simple as it seems. Whether you're taping boxes in your garage or ready to outsource, this convo hits home. 📢 Enjoyed the episode? Thanks for listening! Leave a revie...
Profit First 20.05.2025 33:58
In this episode, we dive into the "Profit First" mindset; what it is, why it’s hard to implement in the unpredictable cash-hungry world of ecom, and how it’s helped us along the way. From frozen Amex cards to tax surprises, we explore how to manage cash flow when inventory eats your capital, and what it takes to build a business that funds itself - without chasing vanity revenue. 📢 Enjoyed the ep...
Product Product Product 06.05.2025 28:03
In this episode, we unpack why product—not just ads—is at the heart of everything. From launch cadence and customer feedback to staying on-brand (or not), we share what’s been working, what hasn’t, and how we’re both thinking about product development heading into the next stage of our brands. A practical, honest chat from two founders still figuring it out. 📢 Enjoyed the episode? Thanks for list...
Meta Ads Deep Dive 28.04.2025 49:44
I​​n Episode 9 (wow, how did we get here already!), we’re getting real about Meta ads: the good, the bad, and the painfully expensive. We talk through what’s working (finally), what’s not, and all the messy lessons we’ve learned running our own ad accounts without big budgets or fancy agencies. 📢 Enjoyed the episode? Thanks for listening! Leave a review on your favorite podcast platform and share...
Climbing the Sourcing Ladder 22.04.2025 34:56
In this episode, Jack and David go deep on the real behind-the-scenes of product design, sourcing, and packaging—when you don’t have a big team or massive budgets. From hiring designers to leveraging suppliers, and from poly mailers to box regrets, this one’s packed with practical tips for scrappy founders figuring it out as they go. 📢 Enjoyed the episode? Thanks for listening! Leave a review on...
Our Ecom Origin Stories 14.04.2025 33:54
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...
All About Wholesale-B2B 03.04.2025 38:38
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...
Mystery Boxes & Kickstarters 27.03.2025 34:47
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. 📢 Enjoye...
More Fixed Costs 20.03.2025 35:13
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....
How We Use AI 14.03.2025 41:59
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 s...
The Great App Purge 05.03.2025 1:03:49
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...
Underdog Ecom Podcast Introduction 05.03.2025 11:25
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 insight...
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