ZeroSum

Aaron Mog

ZeroSum is a new cybersecurity podcast that aims to talk honestly about the state of the cybersecurity industry. The show rejects standard "threat of the week" news breakdowns and instead focuses on the reality of the market. Viewing the industry through the lens of game theory, the podcast explores how the current cyber market is no longer a rising tide that lifts all boats; for massive VC gambles to win, the burnt-out practitioners on the ground are often the ones losing. The show features guests from all perspectives, including vendors, investors, workers, and CISOs.

Episodes

  1. 2 hr ago ·  Video

    Why Security Always Failed and What Finally Changes That - with Justin Somaini

    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

  2. 5 days ago ·  Video

    The Haystack Got Bigger. The Needles Didn't - with Ed Bellis

    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

  3. 14 Jul

    We Don't Need to Throw Out Security, We Need to Update It. - with Diana Kelley

    "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

  4. 7 Jul

    Is Anybody Safe? Adaptability in the Age of AI Disruption - with Mark Carney

    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 nowWhy Evolve deliberately isn't using AI for autonomous exploitation yetThe 50% false-positive problem with autonomous pen testing toolsAttack chains, business logic, and prioritizing high-impact exposuresChartering an "autonomous enterprise" across every business functionThe death of tasteful outbound and the abuse of the CISO relationshipCareer advice for a tough market: deliver outcomes, not activity Guest: Mark Carney, CEO of Evolve Security. Find him at evolvesecurity.com or on LinkedIn.

  5. 7 Jul

    The Scariest Story a CISO Has Ever Told the Board - with Jason Loomis

    "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 explodesThe hype gap between vendor promises and enterprise realityVulnerability chaining in the era of frontier modelsWhy AppSec is the problem actually worth solvingThe build-vs-buy debate for security toolingA myth-busting rant on AI data paranoia and security theaterWhy "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).

  6. 7 Jul

    The Cyber Industry Is Moving Fast but Chasing the Wrong Things - with Cris Neckar

    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 startupsWhy Cris's first diligence question is always "let me talk to your customers"How the Cursor playbook rewrote the rules of company-buildingHow elite hackers use AI as a force-multiplier, not a replacementWhy "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.

  7. 7 Jul

    Breaking In, Standing Out, and Becoming a "Data Shepherd" — with Wade Wells

    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 résuméThe collapse of entry-level roles and the patience the job market now demandsThe "AI slop" problem: people submitting work they never readWhy everyone is becoming a developer — or a "data shepherd" who validates what AI buildsThe reckless reality of businesses uploading confidential data to AIThe 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.

  • 7 Episodes

About

ZeroSum is a new cybersecurity podcast that aims to talk honestly about the state of the cybersecurity industry. The show rejects standard "threat of the week" news breakdowns and instead focuses on the reality of the market. Viewing the industry through the lens of game theory, the podcast explores how the current cyber market is no longer a rising tide that lifts all boats; for massive VC gambles to win, the burnt-out practitioners on the ground are often the ones losing. The show features guests from all perspectives, including vendors, investors, workers, and CISOs.

Information

  • Creator
    Aaron Mog
  • Years Active
    2026
  • Episodes
    7
  • Rating
    Explicit
  • Copyright
    © 2026 Aaron Mog
  • Show Website
    ZeroSum