This is temporary. There’s no stopping the march of AI across everything you know.
Image set1 image · open to inspect
Robert Chapman·
Gotta be careful out there.
Image set1 image · open to inspect
Robert Chapman·
I bet Nina doesn't get a Christmas card this year.
Image set2 images · open to inspect
Robert Chapman·
It seems obvious, but the strongest sellers I work with get out and do the work. They follow up, they remember people, they're likable, and they don't get hung up on details that don't matter. They also fundamentally don't blame others for their lack of success. It's a competition with themselves.
Nothing is more infuriating, as someone who uses a lot of AI tooling, than suddenly having the overly aggressive corporate security controls get layered on and basically break every workflow useful and interesting about AI.
Robert Chapman·
Field CISO is out, and Deputy CISO is in. Watch it change over the coming years.
Image set1 image · open to inspect
Robert Chapman·
I see this playing out in the market right now. I get asked about attack paths more than anything else.
“Women and children knew deep in themselves that no misfortune was too great to bear if their men were whole.”
The Grapes of Wrath
Image set1 image · open to inspect
Robert Chapman·
codex gpt-5.5 is really good at writing code and wicked fast, but boy, is the overall harness dumb about tool discovery and making sane decisions for a project. Claude Code is so much stronger at just being a smarter coding companion.
Robert Chapman·
MCP or its next successor will overtake HTTP in how people consume data on the web. HTTP won't go away, as MCP will likely continue to ride its rails for a while to come, but the layer at which humans consume data over the internet will disappear behind agent protocols.
Image set1 image · open to inspect
Robert Chapman·
Starting a new book.
Image set1 image · open to inspect
Robert Chapman·
In sales, there are 2 things I know to always be true as the solutions engineer. Your sales person has a disease that prevents them from knowing how to check your calendar. The other is that a BDR/SDR has never found a camera that works.
Image set1 image · open to inspect
Robert Chapman·
A colleague once told me, "Don't make it hard for your customer to give you money." I'm trying to get rates for a HELOC. The number of banks that don't have basic contact information working or phone trees that route incorrectly is astounding. Ascend Federal Credit Union will just hang up on you. The local bank I called won't call me back. It's wild.
Image set1 image · open to inspect
Robert Chapman·
I have a coworker that pronounces Anthropic's Mythos model "me thos" and it cracks me up every time. They've had people try and correct them, and they don't care. Just totally doubled down on it at this point.
Image set1 image · open to inspect
Robert Chapman·
It's been my belief for some time that most sports are completely corrupt at some level. Not for every player, team, or game, but more than we'd care to accept.
I have a love/hate relationship with cybersecurity. I've loved the tech side of it since the early 90s when I first got into computers and hacking. I didn't actually get my first security role until much later in my career, having detoured through other adventures.
One of the biggest challenges I have now is that the cybersecurity space today doesn't feel at all like what it was when I was young. I don't mean in the tech sense; I always expected that to change. I mean in the culture sense.
I've gone to defcon, bsides, blackhat, etc and others and some of the time it feels right and other times I feel like an alien. Part of it is cultural/social. I don't really party and Vegas isn't my scene. I'm not a tattoo guy. I don't "look" the part. I understand that this space is a big tent and I'm painting with a broad brush but there's a stereotype that has been created and I think it's one I don't identify with at all.
There's plenty of nice people and many to learn from, but I rarely feel like I've found my tribe. It's an odd feeling.
I jumped to the vendor side a few years ago. I found a good home here. I get to still be technical but also get the social side of it. It has its own trade-offs. I still feel like an alien among the sales side some days too.
What I like probably most is the actual business of it. This is burying the lede a bit, but this is what I think I stumbled into almost by accident coming to the vendor side: seeing how security and business really meet.
I get annoyed by the white-knighting and crusading that occurs in the security space. It's often so divorced from how organizations and businesses work. There's a place for that conversation, but too often when I see the discourse around security, I think "none of these people have actually had to do this in real life with real people".