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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

46:49

Bundles, Spring Drops & Banned Meta Accounts

Underdog Ecom Podcast ·

2026/04/10

Are you tired of guessing your inventory for seasonal drops or watching your cash flow get tied up in stock? This week, we dive into the highs and lows of our spring collections, and break down how testing strategic bundles and free gifts successfully doubled our ad conversion rates. We also explore how we're using AI like Claude to build custom internal e-com tools, plus share a crucial warning after a random personal Facebook ban locked us completely out of Meta Ads Manager.📢 Enjoyed the

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35:49

The Hidden Costs of Free Returns

Underdog Ecom Podcast ·

2026/03/06

In this episode, we dive into the "hidden underside" of ecommerce: the messy world of returns and reverse logistics. They get real about moving away from "free unlimited returns," the pros and cons of return software like Freight and Redo, and why analyzing return rates at the product level is a game-changer for your bottom line.📢 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

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44:54

AI in E-commerce: Beyond the Hype with Claude

Underdog Ecom Podcast ·

2026/02/26

In this episode, we dive deep into our recent obsession with Claude and how we’re moving beyond the standard AI hype to build actual utility for our e-commerce brands. From automating Klaviyo reporting and analyzing P&Ls to managing local Shopify theme files, we share how we’re using these new tools to act as a "co-founder on steroids" while navigating the thin line between genuine efficiency and productive procrastination.📢 Enjoyed the episode?Thanks for listening! Leave a review on

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34:23

Should You Run Ads or Grow Organically?

Underdog Ecom Podcast ·

2026/02/20

In this episode, we dive into a hot debate of whether to focus on paid ads or organic growth, sharing our personal experiences with the highs and lows of both strategies. We discuss the dangers of ad dependency, the shifting landscape of social algorithms, and why finding a hybrid approach is often the key to building a sustainable e-commerce brand.📢 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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29:57

Selling at In-Person Events

Underdog Ecom Podcast ·

2026/02/13

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

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29:41

How We Use Shopify Flow

Underdog Ecom Podcast ·

2026/01/22

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 .📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite

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28:02

Moving Beyond Survival Mode – Our Resolutions for 2026

Underdog Ecom Podcast ·

2026/01/13

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.📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite podcast platform and share

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36:16

AI Email Platform: Eltie First Take

Underdog Ecom Podcast ·

2026/01/01

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.📢 Enjoyed the

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42:07

Year In Review: Ecom Trends and Challenges

Underdog Ecom Podcast ·

2025/12/20

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.📢 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.💬 Join the Conversation: • Jack

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39:38

BFCM Recap: Record Breaking Month!

Underdog Ecom Podcast ·

2025/12/07

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.📢 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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41:41

First Guest Ever

Underdog Ecom Podcast ·

2025/12/02

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.📢 Enjoyed the episode?Thanks for listening! Leave a review on your favorite podcast

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33:17

Drowning in To-Dos? How Virtual Assistants Are...

Underdog Ecom Podcast ·

2025/11/12

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

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24:06

Survival, Attention Economy…Cactus

Underdog Ecom Podcast ·

2025/10/31

We're in the thick of Q4 chaos—juggling marketing, inventory delays, and algorithms that just don't hit like they used to. In this episode, we get real about burnout, the crumbling attention economy, and why survival might be the most underrated strategy in ecommerce. Plus, Jack introduces a new business philosophy: be the cactus 🌵. Just stay alive.📢 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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49:24

Rebuilding My Meta Ad Account From Scratch

Underdog Ecom Podcast ·

2025/10/16

In this episode, we dive deep into what’s working (and what’s definitely not) in Facebook ads right now, from ASC vs ABO to product-market fit, flash sale testing, and why some campaigns randomly tank. It's a real-time look at rebuilding ad strategy during this tumultuous time of year.📢 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.💬 Join the Conversation: • Jack on X:

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47:19

Q4 Isn’t Just Black Friday: How We’re Actually...

Underdog Ecom Podcast ·

2025/09/17

Q4 is make-or-break for most brands, but it’s not just about Black Friday. In this episode, Jack and David share how they’re approaching Q4 strategy, from high-level planning and product angles to managing cash flow and staying sane during the chaos. If you're an operator in the trenches, this one’s for you.📢 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.💬 Join the

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52:31

Capitalizing on Creativity: Mastering Business...

Underdog Ecom Podcast ·

2025/09/03

In this episode of the Underdog Ecom Podcast, Jack and David dive into how creativity can be a form of capital, especially when you're cash-strapped. From pre-funding tactics and supplier negotiation tips to smart cash conversion cycle hacks, this one's all about doing more with less and making your creativity work like cash.📢 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

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38:26

How would we start over?

Underdog Ecom Podcast ·

2025/08/20

If we could rewind the clock and start our ecom journeys over, what would we actually change? While far from experts, we've both been in the game for several years now, with the battle scars to prove it. In this episode, we dive into what we'd do differently if we could start it all again: from product and marketing choices to financial decisions and team-building lessons. Whether you're just starting out or deep in the grind, this one's packed with the kind of advice we wish someone gave

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38:03

Bid Caps Are Working?

Underdog Ecom Podcast ·

2025/07/31

Jack went all in on bid caps—and in this episode, we break down what’s actually happening inside the ad account. Are they finally working? David and Jack dig into the data, what’s changed, and what this could mean for other scrappy brands testing Meta ads.📢 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.💬 Join the Conversation:• Jack on X: @jackinprogress• David on X:

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25:30

Our Most Valuable Apps!

Underdog Ecom Podcast ·

2025/07/25

In this episode, we break down the apps we can’t live without—the ones that quietly power our stores and would leave us scrambling if they vanished. From managing finances to boosting conversions and staying sane operationally, we’re sharing our real MVPs. If you're feeling app fatigue and wondering what’s actually worth the cost, this one’s for you.📢 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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35:40

Margin Focused Offers

Underdog Ecom Podcast ·

2025/07/16

How do you run a sale that actually boosts your bottom line—and not just your stress levels? This week, we break down the thinking, execution, and outcomes of their latest sales strategies, including tiered discounts, gift card incentives, and how to track what actually worked. Real talk on margins, inventory, and learning by doing.📢 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

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36 results

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