Jack Oswald
Cohost of Underdog Ecom Podcast
Appears in 26 Episodes
First Guest Ever
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 ...
Drowning in To-Dos? How Virtual Assistants Are Keeping Us Afloat
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 ...
Survival, Attention Economy…Cactus
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, ...
Rebuilding My Meta Ad Account From Scratch
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...
Q4 Isn’t Just Black Friday: How We’re Actually Planning for the Biggest Quarter in Ecom
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 p...
Capitalizing on Creativity: Mastering Business Operations
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 ...
How would we start over?
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...
Bid Caps Are Working?
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 ...
Our Most Valuable Apps!
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 fina...
Margin Focused Offers
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 la...
Collabs
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 ...
Email Marketing
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...
Cliffs and Cashflow
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 rethinki...
Bid Caps in Meta Ads?
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 t...
Shipping: In-House vs 3PL
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 cost...
Profit First
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...
Product Product Product
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 wha...
Meta Ads Deep Dive
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 (...
Climbing the Sourcing Ladder
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. Fro...
Our Ecom Origin Stories
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 epi...
