Daniel Mahncke and Shawn O’Malley take a deep dive into Microsoft — the $3 trillion incumbent whose entire investment thesis now hinges on two of the most contested questions in technology: whether AI will reinforce or quietly dismantle the software franchises that built the company, and whether the OpenAI partnership is the strategic masterstroke it appeared to be in 2023, or a relationship that is slowly turning from asset into liability.

Some investors believe Microsoft is uniquely positioned to weather — and profit from — the AI transition, with Azure capturing the infrastructure layer, Copilot embedding AI into the workflows of hundreds of millions of Office users, and a distribution machine no startup can replicate. In their view, the OpenAI partnership remains a crown jewel: privileged access to frontier models, a revenue share on one of the fastest-growing companies in history, and a hedge against any single lab pulling decisively ahead. Others see a far more uncomfortable picture. Office, Excel, and PowerPoint look exactly like the kind of legacy interfaces that generative AI is built to disintermediate.

Join Daniel Mahncke and Shawn O’Malley as they work through whether Microsoft’s software moats can survive the very technology Microsoft is helping to build, examine what the OpenAI partnership actually looks like in 2026 versus the story sold to investors three years ago, and assess whether one of the most widely owned stocks in the world still deserves a spot in The Intrinsic Value Portfolio.