Entrepreneurship
Burnout or Ambition: The Tell Most Founders Miss
Burnout and ambition look identical from outside, so founders misread their own drive. How to tell which of the two engines you are actually running on.
Essays & Field Notes
Field notes from four reinventions — a $200M exit, two unicorns, and building AI-native. Published as I learn.
AI & Technology
The Governance Gap: Why AI Agents Stall Before Production
Most enterprise AI agents die between demo and production. Not on model quality, on the governance gap: who is accountable, can you audit it, can you stop it.
Entrepreneurship
The Seniority Debt: Who Makes Your Next Senior?
The seniority debt is what you take on when you automate junior work and stop growing your own seniors. Here is the real cost, and which roles to protect.
AI & Technology
Context Rot: Why Bigger Windows Make AI Worse
Context rot means a model's effective context window is far smaller than the number on the box. Here is why bigger windows make AI worse, and how to feed less.
Entrepreneurship
The Data Dividend: Should You Sell Your Data?
AI labs are paying millions for company data. Before you take the check, here is what your data is really worth and what you give up when you sell it.
Entrepreneurship
The Standard Drift: How AI Lowers Your Bar
AI made producing work free. The hidden cost is standard drift: your sense of good quietly resets to the machine's median. Here is how to spot it and defend your bar.
Entrepreneurship
Founder Secondaries: When to Take Money Off the Table
Founder secondaries let you sell shares before the exit. Here is when taking money off the table makes you a bolder founder, and how much is far too much.
Entrepreneurship
The Recovery Problem: The Skill You Can’t Delegate
AI runs the happy path and quietly erodes recovery, the one skill you cannot delegate. Why recoverability decays as reliability rises, and how to keep yours.
Entrepreneurship
The Delegation Threshold: When Buyers Stop Testing AI
The delegation threshold is the line where buyers stop testing your AI and start depending on it. Here is how to read it in revenue, and how to cross it.
AI & Technology
The Inference Shift: Where AI’s Real Cost Moved
The inference shift moved AI's real cost from training models to running them. Where the money, the constraint, and the founder opportunity actually live now.