Underdog Ecom Podcast

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.

💬 Join the Conversation:
 • Jack on X: @jackinprogress

 • David on X: @austriker27

📩 Got feedback or topic ideas?

 Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:

 Apply here → underdogecom.com

🎧 More from Underdog Ecom:
 Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 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: @austriker27

📩 Got feedback or topic ideas?
 Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
 Apply here → underdogecom.com

🎧 More from Underdog Ecom:
 Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 system that helps—not hinders.

📢 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: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 support helps us keep it real.

💬 Join the Conversation:
 • Jack on X: @jackinprogress
 • David on X: @austriker27

📩 Got feedback or topic ideas?
 Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
 Apply here → underdogecom.com

🎧 More from Underdog Ecom:
 Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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: @jackinprogress

• David on X: @austriker27

📩 Got feedback or topic ideas?

Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:

Apply here → underdogecom.com

🎧 More from Underdog Ecom:

Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 Conversation:
• Jack on X: @jackinprogress
• David on X: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 real.

💬 Join the Conversation:
• Jack on X: @jackinprogress
• David on X: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com

Podcast: https://podcast.underdogecom.com

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 us when we started.

📢 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: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com
Podcast: https://podcast.underdogecom.com

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: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com
Podcast: https://podcast.underdogecom.com

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 support helps us keep it real.

💬 Join the Conversation:
• Jack on X: @jackinprogress
• David on X: @austriker27

📩 Got feedback or topic ideas?
Leave a comment or email us at [email protected]

🌎 Join the Underdog Ecom Community:
Apply here → underdogecom.com

🎧 More from Underdog Ecom:
Website: https://underdogecom.com
Podcast: https://podcast.underdogecom.com