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Underdog Ecom Podcast

Underdog Ecom Podcast

By: Jack Oswald & David Lindahl
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About this listen

 🚀 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 - No fluff, no filters—just real talk from founders figuring it out in real-time. 💡 Whether you’re starting out or scaling past 7 figures, Underdog Ecom is here to share, inspire, and help you grow. Subscribe now and join the conversation! #UnderdogEcom #EcommercePodcast #DTC© Underdog Ecom Economics Marketing Marketing & Sales
Episodes
  • AI in E-commerce: Beyond the Hype with Claude

    AI in E-commerce: Beyond the Hype with Claude
    Feb 26 2026

    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 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 underdogecom@gmail.com


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

    🎧 More from Underdog Ecom:
    Website: https://underdogecom.com
    Podcast: https://podcast.underdogecom.com
    Show More Show Less
    45 mins
  • Should You Run Ads or Grow Organically?

    Should You Run Ads or Grow Organically?
    Feb 20 2026

    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 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 underdogecom@gmail.com

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

    🎧 More from Underdog Ecom:
    Website: https://underdogecom.com
    Podcast: https://podcast.underdogecom.com
    Show More Show Less
    34 mins
  • Selling at In-Person Events

    Selling at In-Person Events
    Feb 13 2026

    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 on the digital side of the business.


    📢 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 underdogecom@gmail.com

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

    🎧 More from Underdog Ecom:
    Website: https://underdogecom.com
    Podcast: https://podcast.underdogecom.com
    Show More Show Less
    30 mins
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