There's a moment in my conversation with Bob Bobel where he mentions that customers are having a harder time finding people who actually know Active Directory. Not cloud identity — the old on-premise stuff that most large organizations still run, even if they've also got Entra ID and Office 365 sitting on top of it. That expertise is retiring, and it's not being replaced fast enough. Bob is the CEO of Cayosoft, which builds management, auditing, and recovery tools for Microsoft environments. He's been in this space for a long time — long enough to have sold to some of the same agencies he's selling to now, nearly two decades later. He started the company on his 401k, which his wife apparently still doesn't know about. We covered a lot of ground in this episode. Some of it is squarely in the weeds of Microsoft infrastructure — hybrid environments, the gap between what native tools can do and what organizations actually need, and why change auditing matters more than most IT teams realize. Some of it is broader: AI, the ecosystem of companies that build businesses around Microsoft's footprint, and what federal agencies are actually looking for when they go shopping for tools in this space. The recovery conversation is worth your time on its own. Bob tells the story of how Cayosoft ended up building their patented approach to Active Directory recovery — it starts with a phone call at 3 am, a demo coming up in four days, and no hardware anywhere near Key West. The problem they had to solve in that moment turned into something they still consider one of their core differentiators. I'll let him tell it. On AI, Bob is more measured than most people I talk to right now. He's not skeptical of it, but he's also not pretending it's ready to run your identity infrastructure. His argument is that the more realistic near-term use case is capturing what experienced engineers know before they retire — embedding that institutional knowledge somewhere useful rather than just losing it. Cayosoft recently filed a patent around that idea. He explains the thinking behind it, and also where he thinks the hype is running ahead of reality. There's also a good thread in here about what it actually means to build a company inside someone else's ecosystem. I used to work at a company that was tightly coupled to AWS, so I know that tension — the question every year of whether the platform you're built on is going to decide to build what you do. Bob has a pretty clear-eyed take on the Microsoft version of that dynamic. It's a good conversation. Check it out wherever you listen to (or watch) podcasts.