It's an Elephant in the Room takeover by Wes and Dustin Bolander! They're tackling the excuse MSPs keep hiding behind: "We can't sell AI because of our insurance." Here's the truth: most of what you've heard about AI and insurance is wrong, and believing it is costing you revenue.

Nick Ross and Wes Spencer are bringing Andrew Moore onto Above the Stack to talk about how MSP leaders can build an AI learning strategy across the business. We’ll get into what different roles need to learn, where specialization makes sense, and how to turn scattered AI experiments into skills the whole MSP can build on.

Todd Kane and Kyle Christensen will talk through the imperfect, always-changing rules of how to talk like a manager. They’ll cover how to approach difficult conversations, repeat yourself without losing patience, read the room, and decide when to step in versus when to give a situation more time.

This time, the case file feels a little more… magical. All year, Trouble in Techland has dropped MSPs into live incident response scenarios built in partnership with IRGame. The mechanic is simple: watch what happens when smart teams have to make decisions with limited information, rising pressure, and no perfect answer at the bottom of the page.