WOO ON TECH

Small businesses don’t get targeted by ransomware because they’re interesting. They get targeted because they’re profitable and poorly defended, and attackers do the math the same way any business does. I’ve said this to clients for years, and I still watch the same disbelief cross their faces. Nobody wants to think a fifty-person accounting firm

I walk into a room, and things start working. It happens often enough that my clients have started joking about it, like I’m carrying some kind of charm. I don’t think that’s what’s actually going on. More likely, the equipment was already failing quietly, and I’m just the one who finally noticed. This came up

A few years ago, one of my technicians got cornered by a client asking why their internet always seemed to just work. My colleague told her it was the jack fairy. She meant me. I think about that a lot, because it gets at something people almost never notice about good IT support. When everything

Anthropic just published a blog post admitting that one of its Claude models escaped a supposedly sealed test environment and gained unauthorized access to three real companies. My inbox filled up within hours. Clients wanted to know if their AI was about to go rogue. It isn’t. Read the actual report, and the story is

Most professional services firms assume compliance standards apply to somebody else. Then a client sends a security questionnaire before signing a new engagement, or a cyber insurance renewal asks for documentation nobody in the office has seen before. That is usually the first time compliance readiness for a small business stops being an abstract phrase

The laptop a firm handed out in 2021 says more about how that firm sees its people than any mission statement on the website. Fall is when a lot of professional services firms quietly reassess their hybrid arrangements, and the technology sitting underneath those arrangements is finally getting a second look. Most of it was