I run marketing and technology at a mid-market headwear manufacturer. Three brands, B2B and direct-to-consumer channels, and all the complexity that comes with physical products meeting digital infrastructure. I make technology decisions every week — which tools to keep, which to kill, what to build in-house, where to double down on a vendor. I've managed 300+ application stacks, negotiated enterprise software contracts, and watched millions go to tools that nobody used. I know what bad software decisions cost because I've lived with the consequences.
AI changed what I thought I knew about software.
In 2023, I tried building a custom tool with AI assistance. It failed. The technology wasn't there yet. In 2025, I tried the same project. It worked in a weekend. That gap... that experience rewrote everything I thought I knew about when to build and when to buy.
And I'm watching the same thing happen everywhere. Leaders are making software decisions based on intuitions that formed before AI could write production code. They're signing three-year SaaS contracts for capabilities an AI agent could handle tomorrow. They're building in-house when a $20/month tool does it better. The discipline of developing software has changed so dramatically in the last few months that most people's instincts haven't caught up to the capabilities.
I want to fix that. I want people making good decisions and spending their company's money well. That's why I'm building all of this.
What I'm building.
The B4 Index is a software decision engine. 299 categories across 19 domains, each scored on five dimensions. Build, Buy, Bridge, or Beware. It's the independent, data-driven tool I wished existed when I was staring at a 305-app stack wondering where to start.
Build or Buy is the book. The complete framework with worked examples, the methodology behind the scoring, and the thinking you need to navigate software decisions when AI is rewriting the economics every quarter.
The Build Report is the newsletter. Category shifts, new scores, and what's changing in the software landscape. It's where I share what I'm seeing from the operator's seat.
And there's more coming. MCP tools, Claude integrations, an assessment workflow... the goal is a full toolkit that helps you think clearly about software decisions, whether you're a CTO evaluating your stack or a founder deciding what to build first.
Why follow along.
I post regularly on LinkedIn about AI-assisted development, software category analysis, and the build-vs-buy decisions I'm making in real time. If you're trying to figure out how AI fits into your technology strategy... or how to think about software purchases when the ground keeps shifting... that's what I write about.
I'm not a consultant theorizing from the sidelines. I make these decisions at a company that ships physical products to customers every day. The framework, the book, the index... all of it comes from that work. Follow along and it'll sharpen how you think about these decisions too.
The best way to start is The Build Report. Or connect on LinkedIn — I respond to every message.
The Build Report
Bi-weekly analysis of software categories through the B4 Framework. What to build, what to buy, and how to leverage AI to make better decisions for your company.
No spam. Unsubscribe anytime.