Oct 19, 2026

Why a $1M Startup Wasn’t Worth Building in the Age of AI

Jean-Denis Greze, Town's CEO and former Plaid CTO, explains why he shut down a nearly $1M-revenue AI tax business for SMBs and pivoted to Town, an AI assistant that works from email and calendar. The conversation with a16z's Alex Rampell covers founder decision-making under time pressure, product-market fit, the consumer-grade enterprise thesis, token allocation as a business model, neutrality versus frontier labs, horizontal versus vertical strategy, uneven AI diffusion, and how agents may reshape commerce and advertising.

Oct 01, 2026

What Is Jev? The AI Model That Doesn't Generate Text

Jev is a System 1 AI model from TypeSafe that skips text generation entirely, returning calibrated probabilities for fixed-option questions in a single fast request. This explores how it works, how it is trained with reinforcement learning for calibrated decisions, how its probabilities drive software thresholds and guardrails, and how it can complement LLMs in workflows.

Aug 11, 2026

The RAG Mistake Almost Every Team Is Making (with Pete Johnson)

Pete Johnson, Field CTO of AI at MongoDB, discusses effective AI strategies, why most organizations struggle with AI ROI, and how to build reliable AI systems. He covers the importance of choosing the right embedding models for RAG pipelines, introduces Matryoshka embeddings, and explains the evolution of agentic memory to combat token maxing and ensure consistency in production AI.

Jul 31, 2026

Decagon’s Playbook for Building Enterprise AI Applications

Jesse Zhang and Ashwin Sreenivas, co-founders of Decagon, discuss their company's transition to open-source models for enterprise AI, emphasizing how fine-tuned small models outperform frontier models on specific tasks. They delve into the role of application-layer companies in an AI-first world, their product-driven 'glass box' approach for enterprises, and the transformative power of their 'Duet Autopilot' agent, which builds other AI agents. The conversation also covers AI's impact on jobs, highlighting the Jevons Paradox in customer support.

Jul 05, 2026

AI Gave You A Promotion: Why AI Isn’t Replacing Jobs

AI isn't replacing jobs, but profoundly changing them. Jeff Crume introduces a 'diamond' model to explain how AI shifts job roles to higher-value work, leading to a 'promotion' for employees. This transformation, driven by Jevons Paradox, demands new skills like flexibility, curiosity, and critical thinking, ultimately fostering overall growth and innovation in the workforce.

Jun 09, 2026

[404] – Developer Not Found: The Continuing Developer Evolution • Derek Bingham • YOW! 2025

Derek Bingham explores the rapid evolution of developer tools with AI, from coding assistants to autonomous agents. He emphasizes the shift from prompt engineering to context engineering, introduces Spec-Driven Development (SDD) as a framework for quality AI-generated code, and dispels fears about AI replacing developers, arguing instead for increased demand and the necessity of new skills like ethical and systems thinking.