S5 E10 - Doug Finke – From Mainframes to Machine Learning

In this episode, I have a conversation with Doug Finke. A 16-time Microsoft MVP and long-time technologist, Doug’s experience ranges from mainframe assembly programming to pioneering AI integrations in software development. We reminisce about the early days of system programming and explore how those foundational skills have enabled technologists like Doug to excel in the rapidly evolving world of AI.

Doug shares his journey from COBOL and assembler to becoming a PowerShell innovator, highlighting how his early exposure to structured programming and domain-specific languages now serves as a superpower in working with large language models (LLMs). Our discussion pivots to the game-changing potential of AI, specifically the rise of function calling, modular design, and the Model-Context-Protocol (MCP). Doug explains how these patterns transform AI from simple copilots into powerful collaborators capable of orchestrating entire software systems.

We also look at the implications of AI-driven software development for enterprises, examining whether vertical SaaS solutions may soon be disrupted by in-house, AI-built alternatives. Doug emphasizes how AI accelerates both code creation and maintenance, challenging long-held assumptions about whether to buy or build software.

Our conversation concludes with a philosophical lens on teaching AI, the evolving role of junior developers, and the importance of naming, structure, and design patterns in crafting software that AI can effectively understand and extend. Whether you're deep into AI tooling or just starting to explore, Doug's perspective offers a clear bridge between classical computing and today's transformative technologies.