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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

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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39:39

Collabs

Underdog Ecom Podcast ·

2025/07/01

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 fellow ecom founders! Your support helps us keep it real.💬 Join the Conversation:• Jack on X:

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28:31

Email Marketing

Underdog Ecom Podcast ·

2025/06/23

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 platform and share it with fellow ecom founders! Your support helps us keep it real.💬 Join the

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31:58

Cliffs and Cashflow

Underdog Ecom Podcast ·

2025/06/11

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 and YouTube for ecommerce.📢 Enjoyed the episode?Thanks for listening! Leave a review on your

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26:30

Bid Caps in Meta Ads?

Underdog Ecom Podcast ·

2025/06/04

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?Thanks for listening! Leave a review on your favorite podcast platform and share it with fellow ecom

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44:02

Shipping: In-House vs 3PL

Underdog Ecom Podcast ·

2025/05/28

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 review on your favorite podcast platform and share it with fellow ecom founders! Your support helps us

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33:58

Profit First

Underdog Ecom Podcast ·

2025/05/20

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 episode?Thanks for listening! Leave a review on your favorite podcast platform and share it with

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28:03

Product Product Product

Underdog Ecom Podcast ·

2025/05/06

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 listening! Leave a review on your favorite podcast platform and share it with fellow ecom founders

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49:44

Meta Ads Deep Dive

Underdog Ecom Podcast ·

2025/04/28

In 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 it with fellow ecom founders! Your support helps us keep it real.💬 Join the Conversation: •

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34:56

Climbing the Sourcing Ladder

Underdog Ecom Podcast ·

2025/04/22

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 your favorite podcast platform and share it with fellow ecom founders! Your support helps us keep

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27 results

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