Underdog Ecom Podcast Transistor (https://transistor.fm) https://feeds.transistor.fm/underdog-ecom-podcast 🚀 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 61cc3b20-d172-5a0d-96e1-193505935dab no Jack Oswald David Lindahl Underdog Ecom Podcast Introduction en Fri, 10 Apr 2026 09:58:28 -0700 Fri, 10 Apr 2026 09:59:17 -0700 https://underdogecom.com https://img.transistorcdn.com/X9vDd_qQx2PxpnwPeLm4ILrbcnPTO5xvVuM__bt653U/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9jNTdj/ZWZjYzg5NzAyZGRi/ODQ4MDEwMTI0MTQ4/ZjlkOS5qcGc.jpg Underdog Ecom Podcast https://underdogecom.com episodic 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 - 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 🚀 Welcome to the Underdog Ecom Podcast—the raw, unfiltered podcast for ecommerce founders actually in the trenches. ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur Rainier Watch LLC No No Bundles, Spring Drops & Banned Meta Accounts 36 36 Bundles, Spring Drops & Banned Meta Accounts full d1cc3052-f6ce-44bf-b71a-70b89397d469 https://share.transistor.fm/s/62c0eedd 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 collections, and break down how testing strategic bundles and free gifts successfully doubled our ad conversion rates. We also explore how we're using AI like Claude to build custom internal e-com tools, plus share a crucial warning after a random personal Facebook ban locked us completely out of Meta Ads Manager.


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]]> 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 collections, and break down how testing strategic bundles and free gifts successfully doubled our ad conversion rates. We also explore how we're using AI like Claude to build custom internal e-com tools, plus share a crucial warning after a random personal Facebook ban locked us completely out of Meta Ads Manager.


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]]> Fri, 10 Apr 2026 09:57:38 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2809 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 collections, and break down how testing strategic bundles and free gifts successfully doubled our ad conversion rates. We also explore how we're using AI like Claude to build custom internal e-com tools, plus share a crucial warning after a random personal Facebook ban locked us completely out of Meta Ads Manager.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl The Hidden Costs of Free Returns 35 35 The Hidden Costs of Free Returns full b08517c4-ed58-4413-8a3e-cdf0e3677fd0 https://share.transistor.fm/s/8f6b35b0 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 unlimited returns," the pros and cons of return software like Freight and Redo, and why analyzing return rates at the product level is a game-changer for your bottom line.


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]]> 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 unlimited returns," the pros and cons of return software like Freight and Redo, and why analyzing return rates at the product level is a game-changer for your bottom line.


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]]> Fri, 06 Mar 2026 08:16:04 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2149 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 unlimited returns," the pros and cons of return software like Freight and Redo, and why analyzing return rates at the product level is a game-changer for your bottom line.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl AI in E-commerce: Beyond the Hype with Claude 34 34 AI in E-commerce: Beyond the Hype with Claude full 8030d469-eb3a-4fd7-8426-7e29e04e5123 https://share.transistor.fm/s/64349977 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.


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]]> 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.


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]]> Thu, 26 Feb 2026 09:08:05 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2694 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.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Should You Run Ads or Grow Organically? 33 33 Should You Run Ads or Grow Organically? full f9de03e8-86d0-4e94-96da-597b0b75fd58 https://share.transistor.fm/s/ec14f9df 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.


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]]> 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.


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]]> Fri, 20 Feb 2026 08:14:12 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2063 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.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Selling at In-Person Events 32 32 Selling at In-Person Events full c7afb989-7280-4793-8790-c1ecd71be2e9 https://share.transistor.fm/s/80754dd3 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.


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]]> 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.


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]]> Fri, 13 Feb 2026 11:19:04 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1797 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.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl How We Use Shopify Flow 31 31 How We Use Shopify Flow full 81dc01ff-fd92-40b2-a430-db48b4f04242 https://share.transistor.fm/s/b86bc537 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 out bot traffic to deleting expensive pre-order apps, we break down the exact automations saving us time and money . Tune in to hear how we’re hacking the system—and why you might be running “zombie” flows that are secretly slowing down your store .

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]]> 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 out bot traffic to deleting expensive pre-order apps, we break down the exact automations saving us time and money . Tune in to hear how we’re hacking the system—and why you might be running “zombie” flows that are secretly slowing down your store .

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]]> Thu, 22 Jan 2026 07:34:50 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1781 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 out bot traffic to deleting expensive pre-order apps, we break down the exact automations saving us time and money . Tune in to hear how we’re hacking the system—and why you might be running “zombie” flows that are secretly slowing down your store .

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Moving Beyond Survival Mode – Our Resolutions for 2026 30 30 Moving Beyond Survival Mode – Our Resolutions for 2026 full 42307c50-6465-4400-aadf-c21f522f2624 https://share.transistor.fm/s/2606fc37 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 and wholesale. We also break down our specific resolutions for the year ahead, including strategies for tighter product launch cycles, clearing dead stock through bundling, and managing cash flow without revenue-based loans.


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]]> 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 and wholesale. We also break down our specific resolutions for the year ahead, including strategies for tighter product launch cycles, clearing dead stock through bundling, and managing cash flow without revenue-based loans.


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]]> Tue, 13 Jan 2026 09:58:58 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1682 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 and wholesale. We also break down our specific resolutions for the year ahead, including strategies for tighter product launch cycles, clearing dead stock through bundling, and managing cash flow without revenue-based loans.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl AI Email Platform: Eltie First Take 29 29 AI Email Platform: Eltie First Take full 4654b684-9bc9-473f-85cc-66a364f485c3 https://share.transistor.fm/s/707196f4 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 brand. We test the tool in real time, exploring its ability to generate HTML emails and product images, while debating whether AI tools can ever truly replace human agencies. Join us as we break down the pros and cons of the platform's Klaviyo integration and decide if it’s worth the investment for small teams.

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]]> 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 brand. We test the tool in real time, exploring its ability to generate HTML emails and product images, while debating whether AI tools can ever truly replace human agencies. Join us as we break down the pros and cons of the platform's Klaviyo integration and decide if it’s worth the investment for small teams.

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]]> Thu, 01 Jan 2026 09:42:25 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2176 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 brand. We test the tool in real time, exploring its ability to generate HTML emails and product images, while debating whether AI tools can ever truly replace human agencies. Join us as we break down the pros and cons of the platform's Klaviyo integration and decide if it’s worth the investment for small teams.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Year In Review: Ecom Trends and Challenges 28 28 Year In Review: Ecom Trends and Challenges full 1d13fa2e-3226-4f71-b6aa-91cc1111e354 https://www.youtube.com/watch?v=ji_EiCwNAW8 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 actually moved the needle. Plus: what we’re doubling down on in 2026 and why “newness” might be your biggest growth lever next year.

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]]> 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 actually moved the needle. Plus: what we’re doubling down on in 2026 and why “newness” might be your biggest growth lever next year.

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]]> Sat, 20 Dec 2025 14:30:14 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2527 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 actually moved the needle. Plus: what we’re doubling down on in 2026 and why “newness” might be your biggest growth lever next year.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl BFCM Recap: Record Breaking Month! 27 27 BFCM Recap: Record Breaking Month! full ea57473d-3a6f-40b2-aff5-1f4e955ed3d7 https://share.transistor.fm/s/d6cf3187 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.

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]]> 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.

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]]> Sun, 07 Dec 2025 11:01:07 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2378 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl First Guest Ever 26 26 First Guest Ever full 61e7f1ed-eaf0-4458-9b5b-db04290dac6f https://share.transistor.fm/s/f539b7cc 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.

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]]> 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.

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]]> Tue, 02 Dec 2025 06:45:56 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2501 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Toby Johnston Drowning in To-Dos? How Virtual Assistants Are Keeping Us Afloat 25 25 Drowning in To-Dos? How Virtual Assistants Are Keeping Us Afloat full fbd01e8b-dc96-417b-bd22-e8998f5f70cb https://share.transistor.fm/s/daf23b8c 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.

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]]> 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.

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]]> Wed, 12 Nov 2025 09:55:56 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1997 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Survival, Attention Economy…Cactus 24 24 Survival, Attention Economy…Cactus full 779806c2-a160-4227-8726-f3f0842a7892 https://share.transistor.fm/s/2e9bca9f 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.

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]]> 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.

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]]> Fri, 31 Oct 2025 04:13:23 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1446 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Rebuilding My Meta Ad Account From Scratch 23 23 Rebuilding My Meta Ad Account From Scratch full 2be05dfb-3f3b-4530-96a7-d6bb968ea26e https://share.transistor.fm/s/f5c70772 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.

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]]> 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.

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]]> Thu, 16 Oct 2025 05:17:06 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2964 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Q4 Isn’t Just Black Friday: How We’re Actually Planning for the Biggest Quarter in Ecom 22 22 Q4 Isn’t Just Black Friday: How We’re Actually Planning for the Biggest Quarter in Ecom full 7ae1b000-e3b9-49bf-8f94-16f7991b11b5 https://share.transistor.fm/s/af13a554 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.

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]]> 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.

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]]> Wed, 17 Sep 2025 09:51:53 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2839 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Capitalizing on Creativity: Mastering Business Operations 21 21 Capitalizing on Creativity: Mastering Business Operations full 7c46dd94-beca-4299-bccf-06017546b305 https://share.transistor.fm/s/3ea02b7a 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.

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]]> 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.

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]]> Wed, 03 Sep 2025 08:44:48 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 3151 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl How would we start over? 20 20 How would we start over? full b2d9bede-21f8-431a-94ca-70f7af5f0af9 https://share.transistor.fm/s/71efa74b 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.

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]]> 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.

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]]> Wed, 20 Aug 2025 08:29:31 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2306 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Bid Caps Are Working? 19 19 Bid Caps Are Working? full 8363bd73-e16f-4bac-aa1d-dea288d99d41 https://share.transistor.fm/s/855e7b11 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.

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]]> 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.

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]]> Thu, 31 Jul 2025 08:43:10 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2283 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Our Most Valuable Apps! 18 18 Our Most Valuable Apps! full 88aaeaf0-d4bd-4857-983f-b1ed5485fdc0 https://share.transistor.fm/s/26dd2eee 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.

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]]> 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.

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]]> Fri, 25 Jul 2025 08:30:03 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1530 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Margin Focused Offers 17 17 Margin Focused Offers full 9a3cfd77-eb8c-4727-b191-3c281139a6c9 https://share.transistor.fm/s/c73b331b 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.

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]]> 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.

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]]> Wed, 16 Jul 2025 09:58:15 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2140 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Collabs 16 16 Collabs full 976615e5-c9e4-4939-bbe4-5f961abb7fbf https://share.transistor.fm/s/b82e2ce0 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.

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]]> 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.

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]]> Tue, 01 Jul 2025 14:21:52 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2379 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Email Marketing 15 15 Email Marketing full 0227257f-1bec-4966-8a4f-1d32d20a8d1c https://share.transistor.fm/s/3efa9cfd 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.

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]]> 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.

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]]> Mon, 23 Jun 2025 01:39:51 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1711 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Cliffs and Cashflow 14 14 Cliffs and Cashflow full 76a058d3-82f1-481b-bdf7-82c01d4ac39f https://share.transistor.fm/s/dac1c1f5 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.


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]]> 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.


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]]> Wed, 11 Jun 2025 10:01:40 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1918 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.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Bid Caps in Meta Ads? 13 13 Bid Caps in Meta Ads? full e793dd0d-b871-49e6-b3ba-2297e9afb58a https://share.transistor.fm/s/03cf275d 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.

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]]> 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.

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]]> Wed, 04 Jun 2025 14:35:46 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1590 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Shipping: In-House vs 3PL 12 12 Shipping: In-House vs 3PL full a27376bb-6966-4eec-bfa8-6f74e6985412 https://share.transistor.fm/s/0185126c 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.

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]]> 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.

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]]> Wed, 28 May 2025 03:00:25 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2642 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Profit First 11 11 Profit First full 352961fc-a6c9-4b1a-8033-ba01260806d6 https://www.youtube.com/watch?v=X2I2DZFeEI0 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.

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]]> 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.

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]]> Tue, 20 May 2025 13:39:23 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2038 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Product Product Product 10 10 Product Product Product full 577ad67e-5a6e-4045-acec-9638b45555cc https://share.transistor.fm/s/f25249db 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.

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]]> 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.

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]]> Tue, 06 May 2025 06:59:13 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 1683 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Meta Ads Deep Dive 9 9 Meta Ads Deep Dive full 4572e146-ce96-4dca-8bcf-1eb9d8a517b3 https://share.transistor.fm/s/642f742b I​​n 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.


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]]> I​​n 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.


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]]> Mon, 28 Apr 2025 08:00:00 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2984 I​​n 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.


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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Climbing the Sourcing Ladder 8 8 Climbing the Sourcing Ladder full 0b1c9770-d640-4016-92b9-7941f7203825 https://share.transistor.fm/s/6334c47d 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.

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]]> 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.

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]]> Tue, 22 Apr 2025 06:35:59 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2096 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.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Our Ecom Origin Stories 7 7 Our Ecom Origin Stories full be342030-523f-4bec-9bb5-c081257d4c74 https://share.transistor.fm/s/c90efdee 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 episode, they dive into the unexpected twists, early mistakes, and the wins that shaped their journeys, all while keeping it real about what it actually takes to build something from nothing.

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]]> 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 episode, they dive into the unexpected twists, early mistakes, and the wins that shaped their journeys, all while keeping it real about what it actually takes to build something from nothing.

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]]> Mon, 14 Apr 2025 03:42:47 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2034 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 episode, they dive into the unexpected twists, early mistakes, and the wins that shaped their journeys, all while keeping it real about what it actually takes to build something from nothing.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl All About Wholesale-B2B 6 6 All About Wholesale-B2B full 65a1bcce-c0ec-4cc8-bd08-b8307663c12f https://share.transistor.fm/s/e2673daa In this episode, Jack picks David’s brain on all things B2B and wholesale—from getting stocked in REI and airport gift shops to building a Shopify-powered wholesale channel from scratch. They dive into tools like Faire, SparkLayer, and Trunk, discuss margins, outreach tactics, and what makes wholesale a viable (and sometimes brutal) growth lever for DTC brands. Plus, a quick detour into how new AI tools are shaking up creative workflows and initial ecom community reactions. 

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]]> In this episode, Jack picks David’s brain on all things B2B and wholesale—from getting stocked in REI and airport gift shops to building a Shopify-powered wholesale channel from scratch. They dive into tools like Faire, SparkLayer, and Trunk, discuss margins, outreach tactics, and what makes wholesale a viable (and sometimes brutal) growth lever for DTC brands. Plus, a quick detour into how new AI tools are shaking up creative workflows and initial ecom community reactions. 

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]]> Thu, 03 Apr 2025 09:42:29 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2318 In this episode, Jack picks David’s brain on all things B2B and wholesale—from getting stocked in REI and airport gift shops to building a Shopify-powered wholesale channel from scratch. They dive into tools like Faire, SparkLayer, and Trunk, discuss margins, outreach tactics, and what makes wholesale a viable (and sometimes brutal) growth lever for DTC brands. Plus, a quick detour into how new AI tools are shaking up creative workflows and initial ecom community reactions. 

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Mystery Boxes & Kickstarters 5 5 Mystery Boxes & Kickstarters full 281eb29d-67e5-44ee-b798-1990365bb91c https://share.transistor.fm/s/a851aff0 In this one, David breaks down how he pulled off a mystery box sale to move excess inventory—VA hacks, ops chaos, and way better ROAS than expected. Jack’s deep in stockouts throughout a sale, wrestling with whether to open up pre-orders… We get into the real trade-offs of crowdfunding, cash flow pressure, and why sometimes it’s better to just wait—even when customers are begging to buy.

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]]> In this one, David breaks down how he pulled off a mystery box sale to move excess inventory—VA hacks, ops chaos, and way better ROAS than expected. Jack’s deep in stockouts throughout a sale, wrestling with whether to open up pre-orders… We get into the real trade-offs of crowdfunding, cash flow pressure, and why sometimes it’s better to just wait—even when customers are begging to buy.

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]]> Thu, 27 Mar 2025 10:54:29 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2087 In this one, David breaks down how he pulled off a mystery box sale to move excess inventory—VA hacks, ops chaos, and way better ROAS than expected. Jack’s deep in stockouts throughout a sale, wrestling with whether to open up pre-orders… We get into the real trade-offs of crowdfunding, cash flow pressure, and why sometimes it’s better to just wait—even when customers are begging to buy.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl More Fixed Costs 4 4 More Fixed Costs full 111325bf-8226-4ad6-bd66-40c9aafc6965 https://share.transistor.fm/s/a59e2c75 In this episode, we open up about the very real challenges of juggling fixed costs — from surprise fulfillment bills and tariff headaches to stacking revenue-based loans. We discuss how we’re purging unnecessary apps, negotiating SaaS pricing, and finding creative ways to turn fixed costs into opportunities. If you’re navigating tight margins and trying to stretch every dollar, this one’s for you.

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]]> In this episode, we open up about the very real challenges of juggling fixed costs — from surprise fulfillment bills and tariff headaches to stacking revenue-based loans. We discuss how we’re purging unnecessary apps, negotiating SaaS pricing, and finding creative ways to turn fixed costs into opportunities. If you’re navigating tight margins and trying to stretch every dollar, this one’s for you.

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]]> Thu, 20 Mar 2025 05:25:00 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2113 In this episode, we open up about the very real challenges of juggling fixed costs — from surprise fulfillment bills and tariff headaches to stacking revenue-based loans. We discuss how we’re purging unnecessary apps, negotiating SaaS pricing, and finding creative ways to turn fixed costs into opportunities. If you’re navigating tight margins and trying to stretch every dollar, this one’s for you.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl How We Use AI 3 3 How We Use AI full 181ca1ef-3545-41e5-a8b4-8e455960a0e5 https://share.transistor.fm/s/256a4191 This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

This week, we (David & Jack) are getting real about the challenges we’re facing right now in our businesses—along with some cool experiments we’ve tried (fundraiser, anyone?). Plus, we’re sharing practical insights on AI from the perspective of two underdog operators.

If you're a team of one looking to leverage AI to grow your brand, this episode is for you.

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]]> This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

This week, we (David & Jack) are getting real about the challenges we’re facing right now in our businesses—along with some cool experiments we’ve tried (fundraiser, anyone?). Plus, we’re sharing practical insights on AI from the perspective of two underdog operators.

If you're a team of one looking to leverage AI to grow your brand, this episode is for you.

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]]> Fri, 14 Mar 2025 06:44:02 -0700 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 2519 This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

This week, we (David & Jack) are getting real about the challenges we’re facing right now in our businesses—along with some cool experiments we’ve tried (fundraiser, anyone?). Plus, we’re sharing practical insights on AI from the perspective of two underdog operators.

If you're a team of one looking to leverage AI to grow your brand, this episode is for you.

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]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl The Great App Purge 2 2 The Great App Purge full 5b121e53-accb-43ba-baa9-5d98e6d1735b https://share.transistor.fm/s/8f3394ad This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In true Underdog Ecom style, we’re diving deep into the Shopify apps we’re paying for—what’s worth it, what’s not, and how much we’re actually spending. No app shilling here—just two operators figuring out how to cut the bloat and grow more profitably.

If you’re looking to trim unnecessary costs and optimize your tech stack, this one’s for you.

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]]> This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In true Underdog Ecom style, we’re diving deep into the Shopify apps we’re paying for—what’s worth it, what’s not, and how much we’re actually spending. No app shilling here—just two operators figuring out how to cut the bloat and grow more profitably.

If you’re looking to trim unnecessary costs and optimize your tech stack, this one’s for you.

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🎧 More from Underdog Ecom:
Website: underdogecom.com

]]> Wed, 05 Mar 2025 06:55:41 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 3829 This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In true Underdog Ecom style, we’re diving deep into the Shopify apps we’re paying for—what’s worth it, what’s not, and how much we’re actually spending. No app shilling here—just two operators figuring out how to cut the bloat and grow more profitably.

If you’re looking to trim unnecessary costs and optimize your tech stack, 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.

đź’¬ Join the Conversation:
• Jack on X: https://x.com/passportprodigy
• David on X: https://x.com/austriker27

đź“© 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: underdogecom.com

]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl Underdog Ecom Podcast Introduction 1 1 Underdog Ecom Podcast Introduction trailer b42512ee-fb3a-4eea-a524-bccfe80a2479 https://share.transistor.fm/s/451a5ac5 This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In this first episode, we (Jack & David) introduce ourselves, why we started this podcast, and what you can expect. Spoiler: We’re keeping it raw, unfiltered, and packed with actual insights—not just success stories.

If you’re tired of the “get rich quick” ecom content and want to hear real stories from people in the trenches, Underdog Ecom is 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.

đź’¬ Join the Conversation:
• Jack on X: https://x.com/passportprodigy
• David on X: https://x.com/austriker27

đź“© 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: underdogecom.com

]]> This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In this first episode, we (Jack & David) introduce ourselves, why we started this podcast, and what you can expect. Spoiler: We’re keeping it raw, unfiltered, and packed with actual insights—not just success stories.

If you’re tired of the “get rich quick” ecom content and want to hear real stories from people in the trenches, Underdog Ecom is 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.

đź’¬ Join the Conversation:
• Jack on X: https://x.com/passportprodigy
• David on X: https://x.com/austriker27

đź“© 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: underdogecom.com

]]> Wed, 05 Mar 2025 06:54:28 -0800 Jack Oswald & David Lindahl Jack Oswald & David Lindahl 685 This isn’t another e-commerce podcast filled with gurus telling you how rich they are. We’re in the trenches, running our own brands, and sharing the real ups and downs of building an ecom business in 2025.

In this first episode, we (Jack & David) introduce ourselves, why we started this podcast, and what you can expect. Spoiler: We’re keeping it raw, unfiltered, and packed with actual insights—not just success stories.

If you’re tired of the “get rich quick” ecom content and want to hear real stories from people in the trenches, Underdog Ecom is 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.

đź’¬ Join the Conversation:
• Jack on X: https://x.com/passportprodigy
• David on X: https://x.com/austriker27

đź“© 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: underdogecom.com

]]> ecommerce, shopify, bootstrapped, dtc, direct to consumer, bootstrapped business, ecommerce founders, ecom, solopreneur No Jack Oswald David Lindahl