Malware used to take 18 minutes to move through your network. Now it takes 27 seconds. Humans can't respond fast enough anymore.

Graham Westbrook is VP of International Markets at SimSpace — the "AI Proving Grounds" for cybersecurity — with a background spanning DoD/DISA, CrowdStrike, Flashpoint, and a postgrad in AI from Oxford.

Aaron sits down with him for a genuinely global, big-picture conversation about where AI security is actually heading — not from Silicon Valley, but from the ministries of defense, critical infrastructure operators, and enterprises he works with around the world.

We get into why "legacy SOC is no longer sufficient" and the shift from human-in-the-loop to AI-first defense, why governments and banks will build their own models on their own data instead of renting from OpenAI or Anthropic, and the case for preemptive defense — forecasting and patching attacks before they happen, the way Google forecasts weather. Plus: the "zero day clock" racing toward minutes, why finding more vulnerabilities is a dead end, whether AI's benefits will ever reach smaller organizations or just the giants, and why Graham thinks an AI market crash is coming — and what that means for anyone entering the field.

Guest: Graham Westbrook, VP International Markets at SimSpace. Find him on LinkedIn @ https://www.linkedin.com/in/graham-westbrook/

⏱️ CHAPTERS
00:00 Intro
01:57 Where the world actually is on AI (hint: behind)
04:06 Battlefield AI and preemptive cyber defense
06:23 Why every nation will need its own model
09:48 AI, layoffs, and the "data shepherd" future
11:12 What enterprises are actually doing today
14:14 The 27-second breakout and why humans can't keep up
16:09 The zero day clock and forecasting attacks like weather
24:58 Building a digital replica of your organization
29:33 Will AI's benefits ever reach the little guy?
32:49 The arms race with China
55:37 Getting high on your own supply — the coming crash
56:42 Advice for anyone entering cybersecurity

He's an L8 Principal Engineer at Netflix — the kind of technical leader the company puts on the problems that decide whether it wins or loses. And he just watched AI out-hack him.

Scott Behrens is an L8 Principal Security Engineer at Netflix, where over 11 years he's watched the security team grow from a handful of people to over a hundred. Today he's the technical lead for Netflix's Live product security, its Attack Emulation Red Team, and its DDoS research. He joins Aaron for one of the most honest, forward-looking conversations we've had about what AI actually does to security work, and to the people who do it.

Scott doesn't sugarcoat it: he sat down with the latest models and quickly concluded they're better at finding and exploiting vulnerabilities than he is. But instead of doom, he lays out why that's an opportunity and where humans still hold the irreplaceable edge.

We get into why the model matters less than the "harness" you build around it, the idea that human intention and hard-won wisdom are the most valuable resources in the AI race, and what actually happens when your discovery tools start surfacing thousands of real vulnerabilities you now have to fix. Plus: how AI is quietly making security the easiest story he's ever had to tell, the one-line trick that cuts vulnerabilities in AI-written code, and why the best security engineers are becoming systems thinkers, not bug-finders.

Guest: Scott Behrens, L8 Principal Security Engineer at Netflix.

Find him on LinkedIn and read his newsletter, The Engineer Setlist, on Substack.

⏱️ CHAPTERS
00:00 Intro
01:57 Excited, worried, and humbled all at once
04:16 Don't just do the old things faster
07:30 Should security teams fix the bugs, not just find them?
09:30 Human intention is the most valuable resource in the AI race
10:16 The "wisdom" AI doesn't have
12:22 Systems thinking as the human edge
18:14 Why the harness matters more than the model
20:25 Codifying 20 years of expertise into a harness
23:41 You built the harness — now what do you do with the findings?
25:32 What small and mid-size businesses should actually do
27:35 The one-line trick that cuts vulnerabilities in AI code
30:41 Rethinking the front end, WAFs, and detection
32:45 The "isadmin=false" honeypot trick
51:50 The era of YOLO security
53:09 Security as an enablement function
55:04 "The easiest story I've ever had to tell"
56:34 Where to find Scott

#cybersecurity #infosec #AI #Netflix #appsec

For 30 years, the security industry could never fully win. Justin Somaini explains what finally changes that.

Justin Somaini is one of the people who helped define the modern CISO role — former CISO of Symantec, Yahoo, SAP, and Box, and now a Partner at YL Ventures. In this episode, Aaron sits down with him for a genuinely optimistic conversation about why security has always fallen short, and why he believes we're at the most exciting inflection point in the industry's history.

Justin lays out his core thesis: security has never truly succeeded because of two structural problems — you can never hire enough people to review everything, and the industry never solved the "shared accountability" gap with engineering and IT. For the first time, he argues, AI can absorb the enormous amount of pattern-matching work that's always overwhelmed security teams — letting them finally operate at the scale the business actually demands.

We also get into how he learned to separate real founders from the hype (and the belief he had to unlearn), why "drop the first slide" is his number one pitch advice, how CISOs actually make buying decisions versus what they claim, and his honest take on where the funding market is heading. Plus: the first CISO ever, why word-of-mouth beats every marketing tactic, and what makes a startup worth betting on.

Guest: Justin Somaini, Partner at YL Ventures. Find him on LinkedIn or on his podcast, Somaini Trust Issues.

⏱️ CHAPTERS
00:00 Intro
01:38 Learning from Steve Katz, the first CISO ever
04:03 Why a 30-year veteran is optimistic right now
05:23 Why security has always failed — the two real reasons
07:42 How AI absorbs the work that overwhelms security teams
10:03 How to separate real founders from the hype
13:13 Salesperson, or a product engineer faking it?
16:15 "Drop the first slide" — fixing the founder pitch
18:20 Why first-time founders are like teenagers
22:10 The funding market and where it's headed
28:12 Need-to-have vs. nice-to-have
36:42 How CISOs actually make buying decisions
52:00 How to get anyone to care about what you're building
57:04 Where to find Justin

The haystack got bigger. The needles didn't. Ed Bellis on why the vulnerability problem stopped being human-scale.

Ed built Kenna Security, sold it to Cisco, and is now back with Empirical Security, building custom AI models that predict which vulnerabilities will actually get exploited in your environment — not just which ones score high on a generic global list. He joins Aaron for a candid conversation about what AI is really doing to the vulnerability landscape, the security talent pipeline, and the funding environment.

We cover why AI is producing more code than ever and more vulnerable code than ever, what Anthropic told him about not hiring junior devs anymore ("what happens when the seniors time out?"), why every organization needs a model trained on its own environment, and where startups still win against Microsoft and Google. Plus: why raising $180M in a seed round quietly kills your optionality, the "fast no," and the Chicago startup problem.

Guest: Ed Bellis, CEO of Empirical Security → empiricalsecurity.com

⏱️ CHAPTERS
00:00 Intro
01:20 Coming off a raise — what it actually changes
03:22 What money doesn't fix
05:02 The mistakes he won't repeat from Kenna
07:47 Why a huge seed round kills your optionality
09:03 Is private equity coming for cyber?
12:48 Why every company needs its own model
17:22 Is it just YOLO security now?
18:28 The haystack got bigger, the needles didn't
20:25 AI, remediation, and operational risk
23:45 Anthropic doesn't hire junior devs anymore
26:19 If you take the bottom rung out of a ladder
30:42 Advice for a 22-year-old entering cyber
32:57 Cutting through the noise at Black Hat
36:47 Why he loves a "fast no"
37:26 The Chicago startup problem
39:22 Where startups fit against Microsoft and Google
43:47 Build vs. buy: should you train your own models?
49:02 Where to find Ed

#cybersecurity #infosec #AI #vulnerabilitymanagement #startups

"We don't need to throw out what we've been doing all of our careers. We just need to be AI-aware in how we apply it."

Diana Kelley — CISO at Noma Security, formerly CISO at Protect AI, and a 25+ year veteran of Microsoft, IBM, and Symantec — joins Aaron for a grounded conversation on what actually changes, and what doesn't, when AI enters security.

We cover why trust boundaries and identity are still the job even as AI reshapes the attack surface, why the LLM itself can't function as a trust boundary, the shadow AI sprawl most CISOs haven't gotten a handle on, and the identity mess created by agents inheriting permissions from whoever spins them up. Plus: does AI actually level the playing field for builders, or just make the biggest players bigger?

Guest: Diana Kelley, CISO at Noma Security.

⏱️ CHAPTERS

00:00 Intro

01:34 Nearly four decades in security — where are we right now

13:23 The labs stole the data to begin with

22:19 Shadow AI sprawl and the identity problem

28:21 First principles: trust boundaries, not a full rewrite

39:18 Are the frontier labs going to crush every startup?

42:52 AI, equality, and who gets left behind

55:56 Where to find Diana and get involved

#cybersecurity #CISO #AI #infosec

Is any security company safe from AI disruption? Evolve Security CEO Mark Carney's answer: no and that's the wrong question anyway.

Aaron talks with Mark Carney, CEO of Evolve Security and one of the OG figures in security services, about where the industry sits at a genuine inflection point. Mark breaks down why tech-enabled services are hotter than ever while human-only services are a dying breed, and how private equity now runs "AI disruption due diligence" before writing big checks.

We get into:

• Why finding vulnerabilities became a commodity — and where the real value lives now
• Why Evolve deliberately isn't using AI for autonomous exploitation yet
• The 50% false-positive problem with autonomous pen testing tools
• Attack chains, business logic, and prioritizing high-impact exposures
• Chartering an "autonomous enterprise" across every business function
• The death of tasteful outbound and the abuse of the CISO relationship
• Career advice for a tough market: deliver outcomes, not activity

Guest: Mark Carney, CEO of Evolve Security. Find him at evolvesecurity.com or on LinkedIn.

"This is the scariest story I've ever had to tell my board."

CISO Jason Loomis on what AI is really doing to security teams.

Aaron sits down with Jason Loomis for a raw, funny, unfiltered conversation about AI's impact on security teams, careers, and the humans caught in the middle. Jason lays out his "farm team" problem: the tier-one SOC, GRC, and help desk roles that grow new talent are being automated away and he's brutally honest with his own team about it.

We get into:

• Why the security fundamentals haven't changed in 20 years, even as velocity explodes
• The hype gap between vendor promises and enterprise reality
• Vulnerability chaining in the era of frontier models
• Why AppSec is the problem actually worth solving
• The build-vs-buy debate for security tooling
• A myth-busting rant on AI data paranoia and security theater
• Why "security is a revenue generator" is a line CISOs need to stop repeating

Guest: Jason Loomis, CISO at Freshworks and co-host of the new "Gen and Tonic" podcast. Find him on LinkedIn (no pitch-slapping, please).

The cyber industry is moving faster than ever and Cris Neckar thinks it's chasing the wrong things.

In the debut episode of Zero Sum, host Aaron Mog sits down with Cris Neckar, security researcher turned entrepreneur turned VC at Two Bears Capital in Whitefish, Montana. Cris traces his unusual path from hardcore offensive work to venture capital, and explains why the biggest roadblocks in security aren't technical but structural: broken incentives, revenue-first boards, and founders who fall in love with cool tech instead of customer problems.

We get into:

• The "scientist vs. salesman" failure mode that kills early-stage security startups
• Why Cris's first diligence question is always "let me talk to your customers"
• How the Cursor playbook rewrote the rules of company-building
• How elite hackers use AI as a force-multiplier, not a replacement
• Why "nobody wants to buy more red on a dashboard"
• FinOps for AI spend, compliance-as-collateral, and betting on power and data centers

Guest: Cris Neckar, Partner at Two Bears Capital. Connect on LinkedIn or pitch via the Two Bears website.

Cris is a Partner at Two Bear Capital.  The views he expresses are his own and do not necessarily reflect the views of TBC or its partners.

Entry-level security jobs are vanishing so how does anyone break in now? Detection engineer and educator Wade Wells has thoughts.

Detection engineer, educator, and B-Sides San Diego organizer Wade Wells joins Aaron for a practical, honest look at entering and surviving in security today. Wade, who teaches cybersecurity students across all levels, admits the field moves so fast he can no longer confidently tell students what to do, since even the old advice can now be faked with AI.

We get into:

• Why networking and a genuine community footprint beat a perfect résumé
• The collapse of entry-level roles and the patience the job market now demands
• The "AI slop" problem: people submitting work they never read
• Why everyone is becoming a developer — or a "data shepherd" who validates what AI builds
• The reckless reality of businesses uploading confidential data to AI
• The coming "AI living off the land" attack and the yes-but approach to security

Guest: Wade Wells, detection engineer and B-Sides San Diego organizer. Catch him at DEFCON or on LinkedIn and Twitter — just mention where you found him.