Morgan Holland

Essays and tools on monetization, AI agents, and building like a team of one — from Vermont.

Writing

• The First Draft Is the Work — Everyone says PRDs are dead and writing is a relic. They're half right. AI can write a better first draft than you can, and that's exactly the problem: the messy first draft is where the thinking happens, and skipping it skips the work.
• Tearing Down Claude.ai's Free-to-Paid Funnel — An outside-in teardown of Claude.ai's free-to-paid funnel: where the path leaks conversion, and three experiments anchored on the moment a free user is trying to finish the thing they came to do.
• Three Monetization Swings I'd Run on Claude This Quarter — Anthropic went from $1B to $14B in fourteen months, but it still prices Claude per token: a value metric built for a chatbot, not an agent. Three pricing swings I'd run this quarter, with the willingness-to-pay math for each: charge for completed outcomes, get paid to cut customers' compute bills, and sell idle GPUs on a spot market.
• The Agents That Run My Mornings — I'm a product manager who has never shipped production code, and a handful of AI agents run my mornings on a schedule. How a non-engineer wires this up, the one rule that keeps it safe, and the uncomfortable thing they get very good at: noticing what you avoid.
• The Layer Below — Software ate industries, then ambition, and now computation is eating expertise itself. For product managers, AI just dissolved the wall between understanding a problem and building the solution. A field report from inside the shift.
• How to Build an Angel Portfolio That Can Actually 5x — Most angel portfolios die from too few bets, not bad ones. How to think in probabilities, respect the power law, and build a portfolio that can 5x over a decade.
• The GTD Setup That Finally Stuck — I've cycled through every productivity system on the internet and abandoned all of them but one: a boring, fifteen-minute setup I stole off a blog three years ago and still run today. Here's the system, and why it works when nothing else did.
• Productivity Is Unproductive — I went on an OCD-level inbox-zero clean-out over the holiday and noticed something ugly: clearing my lists didn't make room for real work, it crowded it out. A case against productivity systems, by way of Oliver Burkeman's Four Thousand Weeks.
• The Magic of Backlinks — How one dumb feature, the bidirectional link, turns a pile of notes into a thinking instrument that compounds for years. The mechanic, the eighty-year lineage from Vannevar Bush's Memex, why most people quit before month four, and why AI will make the practice matter more, not less.
• Vermont: Building the Ecosystem — A systems-first, twenty-year plan for growing a real startup ecosystem in Vermont, synthesizing Brad Feld's startup-community principles, Donella Meadows' leverage points, and a working map of the people actually building here. A draft, published to be argued with.