Northwoods Security Notes
Latest thoughts on startup security, vCISO leadership, and risk.
Your Certificate Got You in the Room. Now They Start Asking.
About a third of breaches arrive through a vendor, so a SOC 2 or ISO 27001 badge only gets you in the room. Here is what buyers ask next.
7/16/2026Read on Substack →
Your Patch Window Is Now Your Attack Window
Exploits now hit in hours while the median fix still takes 43 days. A CISO's read for founders who can't out-patch the internet.
7/9/2026Read on Substack →
The Vendor Who Disappears
Anthropic's Fable lockout proved a closed AI model can be switched off by a government overnight - for who you are, not what you did. It's a sovereignty risk, not a vendor one.
6/25/2026Read on Substack →
Are You Writing Job Descriptions for People Who Don't Exist?
Startup security postings stack three careers into one role - then sit open for months. Staff the dominant third, buy or rent the rest.
6/18/2026Read on Substack →
You Have ISO 27001. Do You Still Need SOC 2?
Where ISO 27001 maps cleanly to SOC 2, where it doesn't, and how to bridge the gap without rebuilding your security program.
6/11/2026Read on Substack →
Resilience is Key to Startup Survival
So treat recovery measures like your business life depends on them - because it does.
6/4/2026Read on Substack →
The Credentials Nobody's Managing
Non-human identities outnumber employees 82-to-1, and 91% survive off-boarding. A four-step audit to find the ghost credentials in your stack.
5/28/2026Read on Substack →
The Biggest Breach Study of the Year Has a Startup Problem
Verizon's annual breach study analyzed 22,000 incidents. Three findings hit startups harder - and the commentary skips them.
5/21/2026Read on Substack →
Fractional CISO vs. Full-Time CISO: Which Does Your Startup Need?
Small/midmarket CISOs average $415K in total comp. Fractional runs $5K-$15K/month. But the real question isn't cost - it's stage.
5/18/2026Read on Substack →
Put Away Your Hammer - That AI Vendor is Not a Nail
Your SOC 2 checklist was built for something entirely different. If you don't want to wind up like the 97% of AI breach victims who lacked proper AI controls, here are the tools you need.
5/7/2026Read on Substack →
What Your Board Will Ask About AI Security
AI moved from pilot to board agenda faster than most founders expected. Three questions are coming - and the answers reveal more than you think.
4/23/2026Read on Substack →
Why Your Incident Response Plan Doesn't Work (Yet)
Tabletop exercises cut breach timelines by 76 days. Here's how to run one that actually changes your security posture.
4/16/2026Read on Substack →
The Plan You Hope You Never Use
Most startup IR plans are compliance artifacts, not decision-making tools. Five pre-made decisions matter more than forty pages of procedures.
4/13/2026Read on Substack →
The SOC 2 Survival Guide: What Founders Get Wrong
SOC 2 engagements grew 49% in three years - but most startup guidance skips the hard parts. Five mistakes from the CISO side of the table.
3/19/2026Read on Substack →
What Enterprise Customers Actually Check in Security Reviews
Most startups treat the 300-question security questionnaire as a compliance exam. It's a risk triage -- and only 20% of those questions decide the deal.
3/13/2026Read on Substack →
When to Hire Your First Full-Time Security Person
In 2019, security was a cost center. In 2026, it's a revenue gate. Five business triggers that tell you when to hire — none involve headcount.
3/9/2026Read on Substack →
Security Debt: Why Seed-Stage Shortcuts Cost 10x
82% of organizations carry security debt. For startups, every shortcut compounds — and the bill arrives at the worst possible moment.
2/27/2026Read on Substack →
Stop Building Higher Walls: Why 2026 Is the Year of Resilience
How to shift the priority away from prevention
1/5/2026Read on Substack →
The AI Paradox: Why Hyper-Efficiency Could Mean More Human Work
How a 19th-century economic theory can inform our thinking about AI and the future of work.
12/2/2025Read on Substack →

