Jul 18, 2025 · 52m · we-live-to-build
Why Every Checkout Will Have This in 5 Years
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Order Editing co-founder Hamish McKay and host Sean Weisbrot discuss the hidden operational complexities of post-purchase e-commerce, AI-accelerated software engineering, and the broader societal implications of advancing automation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 51.5% of the talking time here. How this is scored →
Sean as informed peer 5.3 Guest teaching 3.4 Guest disagreement 0.8 Sean pushing back 1.3
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 51:14 Hamish Rejects Dystopian Fatalism
Hamish gently resists Sean's existential despair, pointing out that humanity is smart, problems are exciting to solve, and living in fear is counterproductive.
Hardest push from Sean ▶ 43:54 Sean Refutes the Feasibility of UBISean firmly dismisses the optimistic notion that governments will cushion AI job loss through Universal Basic Income, arguing the math makes it impossible.
Biggest teaching moment ▶ 4:15 The Math of Platform AcquisitionHamish schools Sean on the harsh realities of platform power dynamics, explaining why selling to Shopify would likely yield a low valuation compared to private equity.
Sean holds their own ▶ 13:00 Sean Breaks Down E-Commerce Integration HurdlesSean demonstrates his firsthand technical knowledge by recounting why building an e-commerce cash flow auditor failed due to multi-SKU complexity and QuickBooks synchronization.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| The Hidden Scale of Post-Purchase Checkout Mistakes | 4 | 5 | 1 | 2 | Sean asks straightforward business strategy questions about why Shopify has not solved post-purchase editing and whether Hamish aims to be acquired. Hamish explains Shopify's product priorities, negotiating dynamics, and acquisition math in depth. | |
| User Experience Friction and the Origins of Order Editing | 3 | 3 | 0 | 0 | Sean asks about the core user experience value and origins of the company. Hamish recounts the Princess Polly return friction and his own history as a customer support rep handling hundreds of edit requests. | |
| Technical Moats and Backend Complexity in E-Commerce | 5 | 5 | 1 | 2 | Sean probes why competitors have not entered and raises valid technical complications around in-transit package adjustments. Hamish walks through the complexities of dynamic state sales tax recalculation, discount codes, and weight-based shipping rates. | |
| AI Engineering Velocity and Smart Post-Purchase Upsells | 5 | 4 | 1 | 1 | Sean shares his own experience vibe coding a Shopify cashflow audit tool and pivoting away due to e-commerce complexity. Hamish explains how Cursor has boosted his co-founder's velocity and how AI powers post-purchase upsell recommendations. | |
| Conversational AI Assistants and Software Retention | 6 | 3 | 0 | 1 | Sean describes building an expense-auditing conversational assistant with Cursor in two minutes and pitches why e-commerce apps need chat interfaces. Hamish agrees, discussing workflow automation with N8N and how UI familiarity drives SaaS retention. | |
| Early Market Timing and the Evolution of Development Costs | 7 | 1 | 0 | 0 | Sean delivers a long monologue about his 2018–2020 entrepreneurial journey building blockchain chat tools and enterprise AI assistants years before market adoption. Hamish largely listens and acknowledges the shift in development costs. | |
| Content Strategy and Philosophical Engagements with AI | 6 | 3 | 1 | 1 | Sean discusses his content repurposing business and his philosophical voice interviews with AI models like Maya and Bordy. Hamish contributes thoughts on human loneliness, journaling, and using AI for therapy. | |
| Human Creativity, Automation Risks, and Global Uncertainty | 6 | 3 | 2 | 3 | Sean presents an extensive dystopian worldview involving AI job displacement, economic collapse, unviable UBI, and climate disaster. Hamish provides a pragmatic, slightly contrarian counterpoint about retaining human creativity and having faith in problem-solving. |
Statements from this episode (14)
McKay: About 1.5% of Shopify shoppers make checkout mistakes
“What we're finding in the Shopify space specifically, which has this accelerated checkout is about one and a half percent of all people will make a mistake.”
McKay: In five years, every e-commerce checkout will feature order editing
“And we also had the thesis that like, if we do this right, if we execute well here and win in five years, every checkout will have it. And they're not all going to use our software, but every checkout will use this in five years time.”
McKay: Order Editing is built intentionally for an acquisition
“We have the ambition of wanting to get acquired. That's always been the vision for this company is we're building a medium sized business.”
McKay: Shopify would probably offer the lowest valuation in an acquisition
“But if we get to a buying circle, right, and we've engaged 20 vendors that are interested in acquiring this, and maybe there's a couple PE firms in there, I feel like I could almost guarantee that Shopify would probably give the worst valuation out of all of t…”
McKay: Princess Polly customer service rejects order changes within 10 minutes
“If you make a mistake on Princess Polly and you reach out to customer service, their response will be, Hey, sorry, we've already processed your order. It's about a ship in like 10 minutes, and we can't make any changes to it, but we do do free returns.”
McKay: Shopify Does Not Natively Recalculate Sales Tax on Edited Orders
“If you do it in Shopify, Shopify doesn't natively recalculate tax for you.”
McKay: 60% to 70% of Order Editing's software is built with AI
“Now somewhere between like 60 to 70% of our software is probably built with AI or in copilot with AI.”
McKay: E-commerce merchants are actively seeking to consolidate third-party app stacks
“There's a massive, Demand right now from merchants to consolidate the amount of applications in their tech stack, the amount of third party tools. They're practically begging for it.”
McKay: The 'one master app' post-purchase e-commerce strategy is super unattractive
“A lot of the post purchase application strategy right now is how can I be the one master app for everything? And I don't know if I love that strategy. I kind of hate the fact that everyone is doing it. I think that makes it super unattractive.”
McKay: Familiarity and UX will decide the winner between ChatGPT and Claude
“That's what we'll win between Claude and ChatGPT. It's like for the average everyday user, the, Six billion people or whatever it might be. What's going to be most important for them is UI, UX, and how familiar they are with it and how often they use it. So if…”
Weisbrot: Building our 2020 AI product today would cost thousands, not millions
“If I were to have started that business today, I could have had the entire thing working with the AI cost maybe a few thousand dollars and take like two or three months. But it's a, it took two and a half years and cost over a million dollars and we still didn…”
McKay: AI podcasts will fail because humans cannot connect parasocially with AI
“They'll ultimately go and die because humans are Inherently lonely, or at least the majority of the human race would describe themselves as lonely or close to it, and they want to hear two people have a conversation and connect, and they want to connect in a p…”