The Billion-Dollar Mistake Hiding in Every Shopify Checkout episode artwork

EPISODE · Jul 18, 2025 · 52 MIN

The Billion-Dollar Mistake Hiding in Every Shopify Checkout

from We Live to Build

There's a massive flaw in the Shopify checkout process that costs merchants millions in customer service hours and lost revenue. I sat down with Hamish McKay, CEO of Order Editing, a startup that's solving the one problem Shopify hasn't: letting customers edit their own orders after purchase. He breaks down The Billion-Dollar Mistake Hiding in Every Shopify Checkout—the 1.5% of customers who make a mistake and why giving them self-service options is a huge opportunity. We also explore the hidden technical complexities of building for Shopify and dive into a deep, philosophical conversation about the future of work and creativity in the age of AI. This is an essential conversation for any e-commerce founder or operator. Check out the company: https://orderediting.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - Introduction: The Problem with Post-Purchase Mistakes00:50 - The 1.5% Problem: A Massive Hidden Cost for Merchants02:00 - Why Hasn't Shopify Solved This Obvious Flaw?04:15 - The Acquisition Dilemma: Selling to Shopify05:40 - How Self-Service Editing Creates Customer Joy08:45 - The Hidden Technical Hell of Building for Shopify14:40 - How AI is Now Building 70% of Our Software21:20 - The Race to Become the "Master App" in E-Commerce37:45 - The Pleasure of Creation vs. The "Grayness" of AI43:50 - A Dystopian View on The Future of AI and Humanity51:15 - "Why The F*ck Am I Running an E-commerce Company?"Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

There's a massive flaw in the Shopify checkout process that costs merchants millions in customer service hours and lost revenue. I sat down with Hamish McKay, CEO of Order Editing, a startup that's solving the one problem Shopify hasn't: letting customers edit their own orders after purchase. He breaks down The Billion-Dollar Mistake Hiding in Every Shopify Checkout—the 1.5% of customers who make a mistake and why giving them self-service options is a huge opportunity. We also explore the hidden technical complexities of building for Shopify and dive into a deep, philosophical conversation about the future of work and creativity in the age of AI. This is an essential conversation for any e-commerce founder or operator. Check out the company: https://orderediting.com----------------------------------------------------------------------------------------------------------------------------📚 NETWORK BEFORE YOU NEED IT (6 LESSONS THAT MADE SEAN $15M)----------------------------------------------------------------------------------------------------------------------------▶ Get my eBook free - https://welivetobuild.com/network-----------------------------------📈 WORK WITH ME-----------------------------------▶ Buy 300 Lessons From 300 Founders: https://welivetobuild.com/300-lessons-ebook▶ Book a Paid Advisory Session: https://welivetobuild.com/book-a-call▶ Startup Fundraising: https://welivetobuild.com/fundraising▶ Sponsor the Channel: https://www.welivetobuild.com/sponsorship---------------------------------------------👀 CONNECT WITH SEAN---------------------------------------------▶ LinkedIn: https://linkedin.com/in/seanweisbrot▶ Inquiries: [email protected]🕒 CHAPTERS---------------------------00:00 - Introduction: The Problem with Post-Purchase Mistakes00:50 - The 1.5% Problem: A Massive Hidden Cost for Merchants02:00 - Why Hasn't Shopify Solved This Obvious Flaw?04:15 - The Acquisition Dilemma: Selling to Shopify05:40 - How Self-Service Editing Creates Customer Joy08:45 - The Hidden Technical Hell of Building for Shopify14:40 - How AI is Now Building 70% of Our Software21:20 - The Race to Become the "Master App" in E-Commerce37:45 - The Pleasure of Creation vs. The "Grayness" of AI43:50 - A Dystopian View on The Future of AI and Humanity51:15 - "Why The F*ck Am I Running an E-commerce Company?"Leave a Review (it truly helps us grow): https://welivetobuild.com/review Hosted on Acast. See acast.com/privacy for more information.

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The Billion-Dollar Mistake Hiding in Every Shopify Checkout

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This episode was published on July 18, 2025.

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There's a massive flaw in the Shopify checkout process that costs merchants millions in customer service hours and lost revenue. I sat down with Hamish McKay, CEO of Order Editing, a startup that's solving the one problem Shopify hasn't: letting...

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