Jack Oswald
Cohost of Underdog Ecom Podcast
Appears in 40 Episodes
Survival Over Scaling
In Episode 40, we dive into new customer data tools like Outer Signal and debate the real value of headless commerce and AI storefronts for smaller brands. We also ope...
Unscalable Things + Micro Content Creators
In this episode, We dive into the "Hudson Method" of paying micro-creators for high-volume ad creative and debate whether the strategy is a content unlock or a cash-fl...
Train Your AI + Recommerce
In Episode 38, we pull back the curtain on setting up a seamless creator portal using Groundwork and the Big Grow X Big app. We share our exact, no-fluff blueprint for...
Price Testing + E-commerce Trends
In this episode, we dive into the latest Shopify updates, including the rollout of B2B features and native price testing for non-plus merchants. We also share our pers...
Bundles, Spring Drops & Banned Meta Accounts
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 c...
The Hidden Costs of Free Returns
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 unlimit...
AI in E-commerce: Beyond the Hype with Claude
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....
Should You Run Ads or Grow Organically?
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 strategi...
Selling at In-Person Events
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 pay...
How We Use Shopify Flow
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 ou...
Moving Beyond Survival Mode – Our Resolutions for 2026
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...
AI Email Platform: Eltie First Take
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 bran...
Year In Review: Ecom Trends and Challenges
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 actua...
BFCM Recap: Record Breaking Month!
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-u...
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 ...
