Content
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AI-Scaled Attacks: Your Risk Model Is Obsolete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.
#career development
79 posts
Do You Still Want to be a Fireman?
Explore how shifting aspirations can keep your security career future-proof. Discover why continual learning and adaptability are key to thriving in an ever-evolving industry landscape.
All of My Old Jobs No Longer Exist
Explore how evolving technology is reshaping security roles that once thrived. Learn strategies to future-proof your career and adapt to the ever-changing landscape of information security.
4 Old Books on Security You May Not Have Read
Discover four overlooked security books from the past that can enhance your career. Explore these hidden gems from the author's 1999-2003 collection and keep your security knowledge sharp.
Why I Turned Down A Security Job at Playboy
Discover why the author turned down a security job at Playboy, prioritizing career growth and company values over glamour. Learn insights on making pivotal career decisions in his new podcast.
Announcing the Building a Life and Career in Security Podcast
Discover inspiring career journeys in the "Building a Life and Career in Security Podcast." Each episode features interviews with security pros, exploring pivotal career decisions and lessons learned. Subscribe now!
Don’t Go to Hacker Cons
Unlock true career growth in security by broadening your skillset beyond hacker cons. Focus on management, communication, and strategic skills to elevate your career to the next level.
How to Broaden Your Knowledge
Discover strategies to expand your tech and business acumen beyond deep security expertise. Learn how to effectively grow your knowledge in your spare time with this insightful video guide.
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.
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.
My Morning Routine
Discover the intricacies of a balanced morning routine shaped by family dynamics, work demands, and personal habits. Learn how adaptability and planning create a seamless start to each day.
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.