Morgan Holland’s Almanack · Essays and working tools, from Vermont
Every person is a software factory now.
I’m Morgan Holland. I shipped my first sites in middle school, spent a decade investing, then a decade working on growth and monetization at Lyft and Shopify. This site is the working record: essays on monetization and agents, plus tools you can use.
The Register of Essays
- Sixty Cycles: A Tour of the Machine That Refuses to Die — The power toasting your bread did not exist a moment ago — it is being made right now by a rotor four hundred miles away that felt you push the lever. A tour of the electrical grid: why it is so hard to kill, how it amputates itself to survive, and what a water tower is really for.
- 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.
Trillions of Souls
A serialized graphic novel, free on this site. Read Chapter One.
Tables of Useful Reckoning
Labs: interactive growth tools where the math runs in your browser.
Watson, the Hired Hand
Meet Watson, the agent that runs its own product business.
The Planting Table
Projects: twenty-odd shipped side projects.