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BH Bil Harmer Operating Partner and CISO at Craft Ventures, Bil Harmer advises its portfolio and investment team on security, privacy, and IT. Before that he was Americas CIS...

“Trust is simply repetition over time.”

Cybersecurity Headlines · August 2026

“Trust is simply repetition over time.” — Bil Harmer, Cybersecurity Headlines

Harmer was laying out the zero-trust philosophy — that no service should be trusted by default. His line compresses the whole idea: trust isn't a status you hand out, it's something a system earns only by behaving predictably again and again.

Cybersecurity Headlines · 2026-08-21 Listen to the episode → More from Bil Harmer →

Transcript

Cybersecurity Headlines Around 14:50 into the episode
David B. Cross

I agree with Bill. I think like that, certainly the endpoint endpoint protection is going to include the behavioral detections and other type of things that we're seeing with the agents. It's part of the future. It's the reality.

Rich Stroffolino

…seems like it was almost created on a dare to use as much Microsoft stuff as possible here. Anything here stand out to you? And do attacks like these have to change how we treat so-called trusted services? I know Zero Trust has been on everybody's lips for years. At this point, nothing new there.

Bil Harmer

Yeah, so there are no trusted services. Just don't trust them. That is what zero trust, that's the philosophy. Trust is simply repetition over time. And not to slag on Microsoft, but I don't know, Patch Tuesday. You know, vulnerability in Microsoft is like a Tuesday. But they are running something at a massive scale and running things at massive scale requires a lot of coordination. And you can hide these things really, really well inside some of these in some of these platforms. So I think, you know, as you build out, as you develop on more…

Rich Stroffolino

Yeah, always talking about, you know, consciously accepting risk, right? And if we know, you know, to that, to that point, you know, Microsoft is a known, it carries some risk. Obviously, a lot of businesses are still going to choose to accept that based on, I don't know, the entire history of…

David B. Cross

Well, I think that Bill really kind of talked about here a little bit. It's like it's zero trust, right? It means you're zero trust everybody. You know, all your SaaS providers, you cannot trust them. You cannot trust these domains, right? And I think that's the reality. And so just kind of…

Rich Stroffolino

This is a whole nother issue, but I'm just so curious because we're talking about that. We've been talking a lot internally at the CISO series just about the challenges of SMB security, one as an SMB ourselves, but two, just in this category. And this kind of living off the land stuff feels like…

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