Caleb Sima of WhiteRabbit

In this episode of Modern Cyber, Jeremy is joined by cybersecurity veteran Caleb Sima for a deep dive into the practical realities of securing AI inside organizations. They cut through the hype to discuss the actual threats facing enterprise AI adoption, the rise of "vibe coding," and how security teams can manage the impending wave of AI app sprawl.

Key Episode Highlights:

The Core Threats: Caleb identifies prompt injection as the number one most likely and impactful threat model for AI systems today, followed closely by data poisoning.
The Rise of "App Sprawl": As employees across departments like HR and Finance use AI to build their own functional applications, organizations will face a massive shadow IT challenge without proper deployment pipelines.
Defending the Inputs and Outputs: Managing AI security requires an approach similar to handling cross-site scripting, monitoring the inputs coming from untrusted sources and analyzing the outputs to prevent unauthorized actions.
Getting Back to Basics: To secure AI, organizations must start with foundational visibility, establishing AI councils, and routing all LLM traffic through centralized enterprise gateways or firewalls.

About Caleb

Caleb is a multi-time founder, CEO and CTO, and also a CISO and practitioner at CapitalOne, DataBricks and RobinHood. Caleb has also recently started his own cyber investment firm, WhiteRabbit. At his core, Caleb is an engineer who loves problem-solving, getting into the weeds at the keyboard, and building things that matter.

Episode Links

Caleb Sima on LinkedIn: https://www.linkedin.com/in/calebsima/
WhiteRabbit: https://wr.vc/

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(138)

This Week in AI Security - 15th October 2026

Back to the normal fifteen-minute format this week, across three themes: a couple of fresh attacks, a run of agent-behavior breakouts, and the policy response forming around them. Attackers are now dr...

15 Okt 17min

Søren Brandbyge & Adam Burns on Email and DNS

Email is the one application almost everyone on the internet uses every single day, and almost nobody understands how fragile it really is. In this two-part episode, Jeremy Snyder sits down with two g...

13 Okt 50min

This Week in AI Security - 8th October 2026

Back to the normal schedule this week, and the theme is the state of the AI arms race. Three major reports landed at once, from Microsoft, Google, and Anthropic, and the shared message is that attacke...

8 Okt 14min

This Week in AI Security - 1st October 2026

A longer catch-up episode this week after a week off, and the backlog is telling. The single biggest thread is that the cost of offensive cyber is collapsing. An open-weight model, Z.ai's GLM 5.3, is ...

1 Okt 26min

Richard Stiennon of IT-Harvest

Jeremy Snyder sits down with industry analyst Richard Stiennon, founder of IT-Harvest and author of the annual Security Yearbook, for a tour of the cybersecurity industry from the inside. Richard has ...

24 Sep 47min

This Week in AI Security - 17th September 2026

A shorter episode this week, recorded from the sidelines of Mind The Sec, soon to be Black Hat Latin America. The headline is distillation. Two separate disclosures, one from Anthropic and a joint adv...

17 Sep 9min

Jonathan Schaeffer of Kind

In this episode of Modern Cyber, Jeremy is joined by Jonathan Schaeffer, a 40-year AI veteran and the inventor of Kind, to discuss the sweeping evolution of artificial intelligence. Jonathan traces th...

11 Sep 48min

This Week in AI Security - 10th September 2026

This week's episode covers several stories plus a couple of topics that sit just outside the strict security lens but are too important to skip. The theme is hard to miss. AI agents are now running th...

10 Sep 14min