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(120)

This Week in AI Security - 2nd July 2026

A lighter week on volume, which gives Jeremy room to go deeper on a set of stories that all reinforce trends we've been tracking for months. The through-line: prompts keep showing up in places nobody ...

2 Jul 12min

This Week in AI Security - 25th June 2026

This week's episode is short but loaded. Jeremy walks through a run of stories where AI is reshaping both sides of the security fight at once. Models are now surfacing decades-old vulnerabilities that...

2 Jul 13min

Taylor Hersom of Eden Dta

In this episode of Modern Cyber, Jeremy is joined by Taylor Hersom, Founder of Eden Data, to explore the critical intersection of cybersecurity, compliance, and enterprise growth.They discuss why star...

24 Jun 42min

This Week in AI Security - 18th June 2026

In this episode, Jeremy explores the fallout of the first US government-mandated global model kill switch, an unprecedented action taken against Anthropic's new Fable model. We also examine CISA's rad...

18 Jun 14min

Kenneth Ellington of Ellington Cybersecurity Academy

In this episode of Modern Cyber, Jeremy sits down with Kenneth Ellington, founder of Ellington Cyber Academy, to explore the rapidly evolving landscape of SIEM engineering, threat hunting, and automat...

16 Jun 30min

This Week in AI Security - 11th June 2026

In this episode, Jeremy explores how the automated "Vulnpocalypse" is officially manifesting in enterprise networks. As Microsoft logs a historic record-shattering Patch Tuesday to keep pace with AI-a...

11 Jun 12min

Nick Cawthon of Guage

In this episode of Modern Cyber, Jeremy sits down with Nick Cawthon, an enterprise-scale design strategist and user experience researcher, to explore the critical and frequently neglected relationship...

9 Jun 38min

This Week in AI Security - 4th June 2026

In this week's episode, Jeremy reports live from the sidelines of Infosecurity Europe in London. As state-sponsored actors turn to thousands of automated recursive prompts to weaponize zero-days, the ...

4 Jun 14min