Mark Baker is VP of IT at Block Imaging in Michigan. They service legacy medical equipment. Big iron MRI and CT machines that hospitals can't replace.Which means Mark deals with Windows systems no longer patched, medical device regulations, and security frameworks spanning three decades of technology. The fundamental challenge hasn't changed since Mark started at a small computer shop. Back then it was "what's a network card?" Now it's "we need AI." Different technology. Same conversation. A CEO gets on a plane, reads an article, comes back convinced this will solve everything. Mark's the one who explains physics. We get into why 85% of AI initiatives fail to return value. Mark doesn't chase bleeding edge. He's a fast follower. He waits to see what actually works before committing. "I'm not looking for a solution that's looking for a problem. I actually have an issue. And how can I actually address this with what I know about AI today?" We talk about the vendor myths that keep recycling with new labels. Cloud means you don't need backups. Wrong. It's more resilient, but not backed up unless you pay for it. New technology will save you money. Also wrong. AI tools are underpriced right now. OpenAI charges fifty bucks for something costing them two hundred to deliver. Those prices are going up. Mark destroys the idea that IT projects happen overnight. "This did not occur overnight. This will not be corrected overnight." Projects are underestimated. The lift is bigger than anyone thinks. Trying to run fast without proper planning just means you pile the next thing on top of the last thing until throughput slows to a crawl. We get into why Mark hates the word no. It shuts down conversation. When a request will blow up the security framework, he doesn't just reject it. He explains the why. He brings it to a conversation. "We have to be tactical about what we're doing and if it is the wrong path, bring that to a conversation, not just say no and walk away." The biggest struggle? IT pursues technology for technology's sake. Mark's seen departments chase zero trust or cloud without asking if it aligns with where the business is actually going. The mistake is forgetting that IT exists to solve business problems, not implement the latest framework because it sounds impressive. The answer? Push business knowledge down through your entire IT organization. From VP to intern. Everyone should understand how their work connects to company goals. Mark challenges his team to take accounting classes. Understand EBITDA. Learn the business, not just the tech stack. Because you can't speak business language if you don't understand the business.