All Episodes

I Sent the AI a Strongly Worded Prompt. I Think We'll Be Fine.

Data Is the New Oil, in That It's Useless Until You Refine It

Mirror, Mirror on the Wall, Who Has the Best Infrastructure of Them All?

Our AI Agents Are So Safe and Reliable You Can't Buy Insurance for Them

BONUS EPISODE: Super Cyber Friday Express - Hacking Vendor Selection

We Strongly Value Your Willingness to Accept Less

Backlogs? Where We're Going We Don't Need Backlogs.

When Frameworks Stop Being Polite and Start Getting Real

"Ignorance Is Bliss" Is Our Acceptable Use Policy

Secure by Design. Ignored by Default.

Why Solve Your Problems When We Can Just Scare You?

See, Our Compliance Framework Includes a Checkbox for Resilience

Why Don't You Tell Me Which Metrics Sound Most Impressive?

With AI, I Can Now Be Pulled in 5x More Directions at Once!

The Only Thing Worse Than Technical Debt is Newly Discovered Technical Debt

What Part of Zero Trust Does Your Exception Not Understand?

These Aren't Speed Bumps, They're Opportunity Ramps! (LIVE in NYC)

It's Not That We Don't Value Your Experience, We Just Don't Want to Pay for It

Boards Love to Hear Jargon," Says Soon-to-Be-Fired CISO (LIVE in Boston)

There's Nothing an LLM Can Screw Up That the Cloud Didn't Do First

Our Data Security Policy Is Transparent in That It Doesn't Exist

If You Love Cloud Misconfigurations So Much, Why Don't You Marry Them!

Why Be Responsible When We Can Just Blame AI?

Can You Please Train the AI on Your Way Out the Door?

AI Confidence: It's a Trap! (LIVE in San Francisco)

Step 1: Deploy New AI Tool. Step 2: Discover Security Flaws. Step 3: Repeat. (LIVE in Orlando)

Back in My Day, You Could Get a Cybersecurity Job at the Corner Store

Our Theoretical Controls Work Great Against Hypothetical Attacks

Remember, Every Underappreciated Risk Is Just a Crisis Waiting to Be Discovered

Do You Think These Compliance Boxes Check Themselves? (LIVE in Clearwater, FL)

Why Highlight Diversity When We Can Just Hope You Don't Notice?

They're Less "Best Practices" and More "Sounds Good on LinkedIn"

It's Okay to Put All Your Eggs in One Basket as Long as You Really Trust the Basket

Our Security Team's Love Language is Buying New Tools

If We Can't Do Better, at Least Do It Faster

We Gave the CISO Risk and Liability, and Now They Want Authority. The Nerve.

When We See White Smoke, We Know We Have a New CISO

Take Two-Factor Authentication and Call Me in the Morning

I'll Show You Our Resilience Plan Once Our Cloud Storage Is Back Online

AI Is Very Efficient at Making Us Forget the Value of Humans

Managing Risk Has Been a Priority Ever Since You Asked About It (LIVE in NYC)

Imagine Scaling Mistakes 5x Faster. Thank You, Automation! (LIVE in NY)

How Much Risk Would a CISO Risk if a CISO Could Risk Risk? (LIVE in Boca Raton)

I'm Worried That We're Not Worried About the Right Worries With AI

You Can't Fall Behind in AI if You Never Start

Why Architect for Human Error When We Can Make People Feel Really Bad About It?

Are You Implying This Line Graph Isn't a Compelling Cybersecurity Narrative?

Our CISO Certainly Puts the Tool in Multi-Tool (LIVE in LA)

I Don't Just Guess About Effectiveness, I Make Educated Guesses!

It's a Little Hard to Evaluate New Solutions When You're Screaming "AI" at Me All the Time (Live in Houston)

Dear Abby: Why Should I Trust a Vendor Selling Me Zero Trust?

The Difference with AI Red Teaming is We Added the Word AI

Don't Worry, We'll Get to Solving Your Problem on Slide 87

Time to Choose a Security Vendor: Dart Board or Spin the Wheel?

Now That You Mention It I HAVE Heard Some Hype Around These AI Tools

Wait, SMS Doesn't Stand for "Super Mega Secure?"

We All Agree That Prevention Is the Best Advice We're Never Going to Follow

We're All for a Responsible AI Rollout as Long as It Goes as Fast as Possible

New Study Finds No Email Has Ever "Found You Well"

I Just Can't Communicate With the Business. I've Tried Condescension AND Derision.

Impressive! Our AI is Approaching "One 9" of Accuracy.

They Can't Hack All Our Tools If We Keep Buying New Ones

Cosmo Quiz! 23 Ways to Make Your Vendors Obsessed With Your Security Standards

We'll Worry About Recovering From the Attack Once We Ace This Audit

Once You Memorize the Manual, Our User Interface is Very Intuitive

Not Enough Hallucinations? Let's Outfit Your LLM with Another LLM

We Require 3-5 Years of Experience to Qualify for the Cyber Skills Shortage

We Can Either Build Resilience or Just Always Be Perfect

We Checked the "Yes" Box for Cybersecurity. What Else Do We Have to Do?

Aside From Text, Images, and Videos, GenAI Can't Fool Me (Live in Boston)

AI Isn't Going to Take Your Job, It's Going to Eliminate It! (LIVE at BSidesSF)

I Can't Choose. I Love All My Assets Equally.

Why Learn Security Fundamentals When We Could Just Chase Our Tails?

I'm Not Looking Down at You, I'm Looking Down at What You're Doing

They're Not AI Mistakes, They're Happy Little Incidents

Get ALL the Challenges of Cybersecurity AND Fewer Resources

Data Minimization Means We Don't Tell You What We're Collecting

Welcome to Cybersecurity: Where Everything Is Made Up and the Points Don't Matter

With AI, Don't Think Like a Hacker, Think Like the Whole of Society

This Security Control Is So Good We Don't Even Have to Turn It On (LIVE in Clearwater, FL)

The Security Incident Has Been Upgraded From "Ouch" to "Boiiiing" (LIVE in Orlando, FL)

How to Best Maintain a Healthy Work-Work Balance in Cybersecurity

Our CISO Might Be Virtual, But the Lack of Respect Is Genuine

All Cybersecurity Problems Are Easy to Fix… With Unlimited Time and Budget

Every Failed Startup Starts as a Dream for a Single Pane of Glass

Fix it? Let's Just Get Rid of It.

Zero Trust Purple Team DevSecOps Mesh: A CASB Journey Through the Identity Fabric

Our Developers' New Motto is "LLM Take the Wheel"

As Long as We Keep Moving the Goalposts, We Have a Great Security Culture (LIVE in Dallas, TX)

4th Party Data Breach? We Can Barely Catch the 1st Party Ones!

I Support Open Source as Long as I Don't Have to Invest in It

Ewww! How Long Has This Router Been in the Fridge?

Why Bother Helping Users When We Can Complain About Them?

Can't Our Employees Just Go Back to Stealing Pens?

We Take Software Security Seriously, As Long As It Ships on Time

Aww, Your Cybersecurity Concerns Are So Adorable (LIVE in La Jolla)

Once You Show Me Your Diploma, I'll Explain Why We Don't Gatekeep

Wait, We Can Prioritize Data Privacy Before an Incident? (LIVE at Stanford University)

Luckily, We Haven't Had to Adapt to Any New Technologies Before AI

We Need to Hire a Unicorn But We Only Have Budget for a Donkey