Musings of an optimistic skeptic
Every human in the workforce has two crude goals: Get paid 2x more, or keep salary flat? Get paid more! Go home at 11:01 PM, or stay up until 5 AM? Go home at 11:01 PM! This isn’t a moral judgment. It’s just…economics. Which brings us to one of the stranger problems with enterprise AI: Continue reading The Principal-Agent vs. Agents Problem
Almost every day I get a note from a student saying they want to get into venture investing. got a nice one yesterday from a rising senior at Harvard (comp sci major), here was my response: my strong, strong recommendation: don t start in venture capital or even investing! this is the greatest time in the Continue reading Don t (Start) Work in Venture Capital
What is a System of Record, and what makes some stickier than others? A system of record keeps track of the atomic units of a business. Calendars for resources and people (busy vs free), inventory (in stock vs not, delivery dates, costs), personnel (hours worked, vacation days, and salaries), shareholders (ownership, options, and types of Continue reading Systems of Record
The proliferation of AI demands a new proof of work. Personalized, intelligent spam is still spam. Personalized, intelligent unwanted sales calls are still unwanted. Humans just checking in can now be superpowered and never drop a ball again which means all communication is going to be so crowded as to be unusable. Bitcoin s origins date back to Continue reading AI s Proliferation Requires a new…
If you try to get advice from anyone *where they lack full context* you can build support for any position imaginable. Imagine: the hospital refused to do surgery on this patient to fix this problem? Isn t that outrageous? without the context of the patient is 104 years old. Try asking a startup investor: should I Continue reading Advice on Seeking Advice
Seed bets are largely people bets, and the way I think about them is a set of simple (but hard to know!) assessments of the entrepreneurs can they materialize labor and capital, are they going to get to traction on the seed (vs what I call a slow boil company), and how prolific/encyclopedic are Continue reading How to Invest in People
The payments market is going to massively expand over the next decade because: 1. ANYONE can now build anything digital — AI code creation means exponentially more digital SKUs that can be created and, of course, paid for. We are in the very early innings here. The gating item is just human creativity. It s not Continue reading Digital Payments are Going to REALLY Grow
Somebody needs to build a parallel education stack, from top to bottom. The current one is just too broken. There s an incredible new input to education (learn anything for free with AI!) and a very different world in terms of needed skills (and economic realities) upon graduation. Against a legacy cost curve that seemingly is Continue reading Redoing Education: Lysenkoism and Preference…
The best entrepreneurs constantly “read the room” (or the market) and adjust their presentation style, their mannerisms, their product description, their team, their focus, their advisors — everything. They have the smallest number of axioms (things they accept without questioning). Everything else is subject to questioning, upgrading, and re-synthesis. Particularly since almost invariably they…
History doesn’t repeat, but it rhymes. Before SaaS, and before freemium, there was “shareware” — try before you buy software. This was a concept dating back to the 1980s, where software would be freely distributed on floppy discs attached to PC magazines…dozens of products on one floppy! Written by hobbyists and even upstart companies. id Continue reading Software Clone Wars of 2004, meet AI…