Gallery inside!
Artificial Intelligence

AI’s Biggest Flaw (And Why It Matters)

👔 CEO Lens: Strategy & SocietyAI red teaming used to mean thinking like the enemy. Today, it too often means poking a chatbot with clever prompts. But in a world racing toward agentic AI, that’s not enough.Red teaming was born in war — from Prussian tabletop simulations to RAND's Cold War Soviets — and later evolved to spot systemic blind spots in cyber, defense, and diplomacy. Its goal? Prevent catastrophe by thinking adversarially, not reactively.Now AI is the battlefield. And according to a new research paper, we’re getting the playbook wrong. Instead of challenging assumptions across the lifecycle — from data integrity to deployment resilience — we’ve reduced red teaming to viral jailbreaks and “gotcha” demos.For leaders, the risk is existential. Models trained on 15 trillion tokens aren't just big — they're opaque, dynamic, and potentially unstable. Governance can’t be performative. It must be strategic, systemic, and future-proof.Boardroom questions must evolve:Are we red teaming models… or entire systems?Who red teams the supply chain, datasets, and deployment logic?Will shallow exploits blind us to emergent failure modes that collapse trust entirely?🛠️ CTO Lens: Systems, Scaling & RiskRed teaming should never be a bug hunt. It’s systems-level adversarial design.Yes, micro-level prompt testing matters — but so does macro-level resilience:At inception: Should this model even exist? What are the human-AI assumptions?At training: Where’s the poisoned data? Are privacy leaks embedded?At deployment: How does the model behave under stress? What happens at retirement?And beyond both is what the paper calls the meta level — the domain of emergent risk:When multiple AI agents interact, will new behaviors emerge?When AI and humans co-adapt, will vulnerabilities hide in the seams?Can we detect when systems evolve outside their design intent?Frameworks like MITRE ATT&CK revolutionized cybersecurity by codifying adversarial emulation. AI red teaming needs the same. Think threat models, feedback loops, and continuous monitoring — not just pre-launch theatrics.🎯 Investor / Strategist Lens: Market & MomentumThe “copilot era” is here. AI is shipping fast — but red teaming is drifting.In 2023, DEFCON hosted the largest AI red teaming exercise in history. But researchers warn that these flashy events create a false sense of security. They test surface-level interactions, not infrastructure-level risks.Markets are hungry for the wrong metrics:Prompt robustness ≠ model trustworthinessOutput filters ≠ governance architectureJailbreaks ≠ systemic safetyThe real opportunity? Platforms that treat red teaming like DevSecOps — integrated, continuous, lifecycle-driven.Enterprise AI Assurance will be a category.Model supply chain security will be table stakes.Emergence simulators may become the next Palantir.This is a chance to back the AWS of AI trust — not the antivirus of 2025.⚡ TechClarity TakeawayAI red teaming is splitting in two:One is reactive, shallow, and gamified.The other is strategic, systemic, and capable of safeguarding the future.Only one of them will scale.👉 The question isn’t if we red team AI — it’s whether we’re taming the beast or just poking it.‍

👔 CEO Lens: Strategy & Society
AI red teaming used to mean thinking like the enemy. Today, it too often means poking a chatbot with clever prompts. But in a world racing toward agentic AI, that’s not enough.

Red teaming was born in war — from Prussian tabletop simulations to RAND's Cold War Soviets — and later evolved to spot systemic blind spots in cyber, defense, and diplomacy. Its goal? Prevent catastrophe by thinking adversarially, not reactively.

Now AI is the battlefield. And according to a new research paper, we’re getting the playbook wrong. Instead of challenging assumptions across the lifecycle — from data integrity to deployment resilience — we’ve reduced red teaming to viral jailbreaks and “gotcha” demos.

For leaders, the risk is existential. Models trained on 15 trillion tokens aren't just big — they're opaque, dynamic, and potentially unstable. Governance can’t be performative. It must be strategic, systemic, and future-proof.

Boardroom questions must evolve:

  • Are we red teaming models… or entire systems?
  • Who red teams the supply chain, datasets, and deployment logic?
  • Will shallow exploits blind us to emergent failure modes that collapse trust entirely?

🛠️ CTO Lens: Systems, Scaling & Risk
Red teaming should never be a bug hunt. It’s systems-level adversarial design.

Yes, micro-level prompt testing matters — but so does macro-level resilience:

  • At inception: Should this model even exist? What are the human-AI assumptions?
  • At training: Where’s the poisoned data? Are privacy leaks embedded?
  • At deployment: How does the model behave under stress? What happens at retirement?

And beyond both is what the paper calls the meta level — the domain of emergent risk:

  • When multiple AI agents interact, will new behaviors emerge?
  • When AI and humans co-adapt, will vulnerabilities hide in the seams?
  • Can we detect when systems evolve outside their design intent?

Frameworks like MITRE ATT&CK revolutionized cybersecurity by codifying adversarial emulation. AI red teaming needs the same. Think threat models, feedback loops, and continuous monitoring — not just pre-launch theatrics.

🎯 Investor / Strategist Lens: Market & Momentum
The “copilot era” is here. AI is shipping fast — but red teaming is drifting.

In 2023, DEFCON hosted the largest AI red teaming exercise in history. But researchers warn that these flashy events create a false sense of security. They test surface-level interactions, not infrastructure-level risks.

Markets are hungry for the wrong metrics:

  • Prompt robustness ≠ model trustworthiness
  • Output filters ≠ governance architecture
  • Jailbreaks ≠ systemic safety

The real opportunity? Platforms that treat red teaming like DevSecOps — integrated, continuous, lifecycle-driven.

  • Enterprise AI Assurance will be a category.
  • Model supply chain security will be table stakes.
  • Emergence simulators may become the next Palantir.

This is a chance to back the AWS of AI trust — not the antivirus of 2025.

TechClarity Takeaway
AI red teaming is splitting in two:

  • One is reactive, shallow, and gamified.
  • The other is strategic, systemic, and capable of safeguarding the future.

Only one of them will scale.

👉 The question isn’t if we red team AI — it’s whether we’re taming the beast or just poking it.

Author
Dylan Blankenship
Managing Editor
August 29, 2025

Need a CTO? Learn about fractional technology leadership-as-a-service.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.