David Evans of Sentiero Ventures on Artificial Intelligence, Lyapunov Time, and the Knowledge Problem | Self-Evident Week 12

I Asked an AI Investor Whether a Machine Could Set Every Rent in New York. He Said It Absolutely Could.This is the Thursday interview closing week 12 of Self-Evident: The Road to 1776. Sunday’s article and Saturday’s history followed a group of Scots to an argument that sounds wrong the first time you hear it — that the most sophisticated arrangements human beings possess were not designed by anybody. Tuesday ran that claim against a rent board, a municipal grocery store, and a federal investment portfolio. This hour puts it to somebody who builds the machine that is supposed to answer it.David Evans is the founder and managing partner of Sentiero Ventures, an early-stage venture fund outside Dallas that invests in business software where artificial intelligence is the core of the product rather than a feature bolted onto it. Before the fund he was an operator. He has been writing software since the early 1990s, built and sold a national digital signage network, and founded EasySeat, an online ticket resale business that reached the Inc. 500 and sold in 2015. He teaches graduate courses on innovation and entrepreneurship at the University of Texas at Dallas. He and Jeff met as seventeen-year-olds sharing a dorm room in Baltimore in August 1995.The question put to him was direct. Could a system read every rent-stabilized building file in New York and produce a number the board could not produce? He said it absolutely could — and then he scoped it, and the scope turned out to be the whole answer. It could read every unit, every tenant, every price and every alternative in the city at once, at a fixed point. What it cannot do is carry that forward, because every decision every person makes compounds against every other one until the thing diverges past recovery. He has a name for that horizon, borrowed from mathematics rather than economics, and he ran into it twenty years ago building ticket prices, where he spent years assuming it was a data problem before concluding there was no data to find, because the events had not happened yet.The conversation also covers why large language models are not on the road to general intelligence, what a dog and a bell reveal about the difference between having the words and having the world, data poisoning as an attack on the record itself, why the arithmetic of federal equity stakes stops working past a certain size, and the moment an aggregator becomes a market maker and the number on the screen stops being a price.The closing monologue does not let the argument off easily. It builds the strongest version of the challenge, grants it everything it asks for, and then runs the week’s test on it anyway.Recorded 6 September 2026. Several matters discussed here are live and may have moved since: the Rent Guidelines Board litigation was argued on 2 September with the decision reserved, and the Senate version of the fiscal year 2027 defense authorization had not been taken up on the floor after cloture on the motion to proceed failed in July.Did this leave us more free, or more governed?⏱️ CHAPTERS00:00 - Introduction to the Episode 01:15 - Guest Introduction 05:11 - Interview Commences 05:47 - Machine Learning in Ticketing 09:09 - The Business Value of AI 13:10 - AI and the Job Market 17:27 - The Scottish Enlightenment and LLMs 23:43 - Data Poisoning and Future Content 29:08 - Technocracy and Government Intervention 32:19 - Can AI Replace Human Planners? 40:11 - The Scale Problem of Government Investing 44:31 - The Solow Paradox and Productivity 47:59 - Market Disruption and Autonomous Trucking 53:35 - Innovation vs. Regulation 57:03 - Post-Interview Reflection 01:02:44 - More Free or More Governed?📚 The companion article for this week, covering Hutcheson, Hume, the Aikenhead execution, the Union vote, Hume’s rejections at Edinburgh and Glasgow, and Francis Alison’s line from Donegal to Chester County:https://www.consequentialactions.com/post/the-scottish-alternative-the-scottish-enlightenment-part-i-foundations🔗 Sentiero Ventures: https://sentiero.vcConsequential Actions publishes four times a week. Sunday article, Saturday history, Tuesday application, Thursday conversation. Next week the Scots continue with the system of natural liberty — Adam Smith and Adam Ferguson, and the argument Smith is famous for is not the argument he thought he was making.#selfevident #consequentialactions #davidevans #artificialintelligence #knowledgeproblem #hayek #davidhume #scottishenlightenment #venturecapital #libertarian This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jeffkellick.substack.com