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AI-Scaled Attacks: Your Risk Model Is Obsolete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.
#professional development
73 posts
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.
How I Work On The Road
Discover how to stay productive while traveling with essential tech tools and gadgets. Explore the featured gear from a recent Minneapolis trip and learn how to optimize your mobile workspace.
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.
Responding to Every E-mail: Two Months In
Discover the journey and challenges of responding to every e-mail for two months. Explore the surprising reactions and insights gained, and why some e-mails may no longer warrant a reply.
My Longest Running New Years Resolution
Discover the rollercoaster journey of a five-year-long New Year's resolution to go paperless. From tech upgrades to small victories and persistent challenges, find inspiration in the quest for digital organization.
We Make A Life By What We Give
Discover the profound impact of giving in this insightful blog post. Explore practical tips for donating money and time, ensuring your contributions align with your passions and foster deeper connections.