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Strategic insights on blockchain, AI, security, leadership, and career in an age of disruption.

The Real AI Risk Hiding in Your Company
78% of CISOs cite AI agent security as their top concern. The danger isn't the model—it's the unsanctioned agent with production access your team built last week.
Recent Essays

Prediction Markets as Insurance: The Kalshi Hedge
A conference used prediction markets to hedge weather risk—turning a speculative exchange into an insurance desk. Here's why it works and what your CFO needs to know.

AI Won't Replace Your Judgment—Just Your Beatmatching
As AI automates technical skills, the real competitive advantage shifts from execution to judgment: knowing which correct answer matters most.

S&P's OpenZeppelin Bet: Risk Rating Meets Smart Contracts
S&P Global's acquisition of OpenZeppelin signals a watershed moment: traditional risk frameworks are now applied to blockchain infrastructure, fundamentally reshaping how institutions evaluate tokenized assets.

AI-Scaled Attacks: Your Risk Model Is Obsolete
Five federal agencies warned of AI-generated exploits targeting industrial systems. The real threat: attackers now scale expertise through automation, invalidating risk models built on scarcity.
#security
142 posts

Finding a Job in Information Security
Discover why aligning job priorities leads to success in information security. Learn from Chris's story and find out why sticking to your values can guide you to the right career path.

Why Developers Don’t Know Security
Explore why developers often overlook security in coding and how education gaps contribute. Discover strategies to integrate security into development from the start and foster a culture of secure coding.

Security Pros Guide to Optimizing LinkedIn
Discover how to stand out in the security industry with an optimized LinkedIn profile. This guide covers crafting a unique summary, selecting impactful skills, and highlighting non-work activities.

7 Types of CISO
Explore the diverse landscape of CISO roles, from Executive to Buried CISOs, and learn how companies can avoid mismatches by aligning the right talent with specific security leadership needs.

RSA: Are We Talking About The Right Things?
RSA's focus misses the mark, overlooking key issues like nurturing security talent, expanding the workforce, and measuring program effectiveness. Let's reshape the conversation for next year's event.

Are We Running Out of CISOs?
Explore the growing demand and dwindling supply of CISOs as fear of breaches drives security leaders to avoid top roles. Discover why experience with breaches is becoming a valued asset.

How We End Up With Too Many Security Policies
Explore the pitfalls of policy bloat in security management, as the article delves into redundant policies, misplaced guidelines, and tech-enforced rules, advocating for streamlined security measures.

You Have Too Many Security Policies
Explore the pitfalls of excessive security policies that prioritize compliance over true protection. Discover how simplifying and reducing policies can enhance your organization's security posture.

Security is Not A Special Snowflake
Explore how to integrate security seamlessly into technology processes, transforming it from a policing role to a collaborative partner, ensuring robust systems without hindering innovation.

How I Curate Security Longreads
Discover how Jay Schulman curates his Security Longreads newsletter in just 15 minutes a week. Learn his efficient process using tools like Feedly, Pocket, and Goodbits to stay informed and share insights.

How to Properly Configure SSL on nginx
Learn how to securely configure SSL on nginx by removing SSLv3, optimizing performance, and enhancing security with TLS protocols and efficient cipher orders.

Security Longreads — Issue #17
Explore the latest issue of Security Longreads, featuring in-depth articles on major data breaches, innovative tech solutions, and privacy concerns in education. Stay informed on key security insights!