The Bespoke Software Myth

This week Matt and Liam pull at a thread they’ve been circling for a while: the idea that bespoke software is too expensive, too risky, and only really viable for the big end of town.

It’s a myth. And once you start poking it, it falls apart in several directions at once.

Liam comes at it from the SMB angle — the mum-and-dad shops, the 10-to-20-person firms competing against the big names that have custom tools quietly humming away in the background. Matt comes at it from the risk angle — the belief that commercial off-the-shelf software is the “safe” option, when in practice it’s often the more expensive, more locked-in, more liability-heavy choice.

Both angles land in roughly the same place: most businesses are being sold a story that doesn’t reflect the reality of where software is, or what it costs, in 2026.

We get into:

• Why small businesses are told bespoke “isn’t for them” — and why that’s wrong
• The rent vs buy analogy, and why custom software is an asset rather than a recurring liability
• Vendor lock-in, licensing surprises, and the “yes, but that’s extra” trap
• De-platforming risk: Etsy banning 3D-printed products, Shopify-style policy shifts, and Scott Hanselman’s “own your words”
• The Salesforce paradox — disruptors that quietly become the thing they were supposed to replace
• Why off-the-shelf software is commoditised, and therefore homogenises the businesses that adopt it
• Your “secret sauce” / superpower / USP — and why encoding it in custom software is the point
• The infamous SAP-via-IBM “Should’ve Altered Processes” anecdote
• Why the entire enterprise software lexicon (bills of materials, work orders, pipelines) comes from manufacturing — and why that model is a poor fit for knowledge work
• How AI is making bespoke development more accessible than ever — though you still need someone who knows what good looks like
• When renting genuinely is the right call (you really shouldn’t rewrite Excel)

It’s a conversation between two people who agree, which Matt and Liam cheerfully acknowledge — and an open invitation to anyone who thinks they’re wrong to come on and argue the other side.

The episode also lands on a clear mission statement for both of them: helping businesses make informed choices about build vs buy, rather than misinformed ones shaped by decades of enterprise sales narrative.

And there’s a teaser for next episode — picking up the related question: what even is “enterprise”? And do you actually need it?

Matt – Lagavulin, in a Superman glass (both birthday presents) 🥃
Liam – Adelaide Hills Pinot Noir 🍷 (the kegs are empty — desperate times)

• Matt’s blog post: The Bespoke Software Myth 📰
• Liam’s LinkedIn post on building custom software for SMBs 💼
• Michael E. Gerber – The E-Myth Revisited 📘
• Etsy’s 2024 ban on 3D-printed products 🔗
• Scott Hanselman on owning your words ✍️

Any Likes 👍, Shares 📣, Subscriptions 🔔, and Love ❤️ go a long way to helping us keep doing this for fun.

Cheers! 🍻