AI 2030

Rohit Sharma spent his first decade in Silicon Valley building a company from two employees to 750 before it got acquired, then landed at True Ventures, where he's stayed for almost fourteen years without ever planning the next move. He tells Chad and Dhruv why he calls AI a new form of labor rather than a technology, why LLMs are Shannon's machines and not magic ones, and why founder visi...

Inbound stopped being a signal the moment LLMs let candidates fire the same resume at a thousand companies at once. Ishan Gupta, CTO and Co-founder of Juicebox, argues the fix isn't better filtering of that flood but a shift back to outbound, where his agents read what someone has actually done to infer adjacent skills, tech stacks, and likely employers rather than matching keywords. He's...

Most enterprise AI projects don't fail because the AI can't perform. They fail because nobody documented what the AI is actually supposed to do, or how it should behave when things get ambiguous. Binny Gill, former CTO of Nutanix and now CEO of Kognitos, spent five years solving that by making English the programming language for business process automation, with a proprietary interpreter...

Most VCs are chasing AI deals right now. Will Quist, Partner at Slow Ventures, thinks most of them are chasing the wrong thing. With somewhere around $1B deployed across pre-seed and seed, Will makes a direct case that the shift from client-server to SaaS was more economically disruptive than anything AI is doing to software today, and that building a defensible company in this environment require...

Francois Chaubard co-created CS224D at Stanford with Richard Socher and others, the course that replaced the entire NLP curriculum two years after launch and still carries his name. He then spent nine years as a founder before closing a $60M enterprise deal at Focal. He is now a Visiting Partner at Y Combinator and a PhD researcher working on alternatives to backpropagation. He is not a generalist...

Jay Hack was building async coding agents before the term "agentic AI" existed in the mainstream, back when GitHub Copilot was the ceiling of ambition and everyone else was focused on IDE autocomplete. As Head of AI at ClickUp, he's now running one of the most ambitious agent bets in enterprise software, a platform that treats agents not as a feature, but as the primary way work gets...

Over a million security guards in the US spend their days watching things happen. Sud Bhatija, Co-Founder and COO at Spot AI, is building the system that makes most of that unnecessary. In this episode, he breaks down how physical AI works at enterprise scale — from the edge-cloud architecture that enables real-time video analysis, to a three-tier multi-agent system that cuts false positives down...

Alex Bates studied artificial neural networks in middle school, founded Mtell to predict equipment failures at oil rigs and power plants, and has now applied that same thinking to executive search at HelloSky. His core argument cuts against the prevailing AI narrative: as LLMs scale, domain expertise and operating experience become more valuable, not less, because the decisions that actually move...

Most teams building AI agents are blaming MCP when their integrations fall flat. Gil Feig , co-founder and CTO of Merge , says that's the wrong diagnosis entirely — and he built the infrastructure layer that connects agents to enterprise systems to prove it. Gil makes the case that MCP is a thin wrapper around API endpoints, and the actual failure point is the access pattern underneath it. He...

The engineers most resistant to AI coding tools are not the junior ones. Chris Kelly, Head of Product at Augment Code, has watched senior engineers, people with 20 years of experience shipping production systems, be the last to adopt. The reason is not fear of job loss. They were trained to build deterministic systems where A plus B always equals C, and a non-deterministic model that occasionally...

Enterprise AI spend on LLM APIs hit $8 billion in just the first half of 2025 — double all of 2024. Most of that spend is going to the same general-purpose models, and Iddo Gino thinks companies are building on a foundation that won't hold. Iddo founded his first company at 17, scaled it to unicorn status by 24, and spent nearly a decade in the API integration space. His position is straightfo...

Every trust and security system in payments was built around one assumption: a human is on the other end. CAPTCHA, email confirmation, UI-based checkout flows — none of it works when the buyer is headless. That's the wall AI agents are running into right now, and it's not a model problem. It's an infrastructure problem. Jim Nguyen, Co-Founder and CEO of InFlow, has watched payments evo...

Traditional competitive moats collapse when anyone can replicate your product by afternoon. Dmitry Shapiro, CEO of MindStudio and former Google executive, explains why the ability to continuously refactor operations in 5-30 minutes matters more than what you initially build, and why the companies resisting this shift are already behind. Over 400,000 agents deployed on MindStudio reveal a pattern e...

RAG isn't just another AI buzzword, it's the architectural foundation that determines whether enterprise AI delivers value or burns budget. Eva Nahari, former Chief Product Officer at Vectara and four-year venture investor, explains why separating data from models matters more than the models themselves, and why 90% of AI implementations fail at the execution layer, not the technology laye...

Customer support exists to paper over product gaps. As AI handles more tier-one resolution, the question isn't whether automation replaces humans, but where human intervention becomes luxury versus necessity. John Wang, Co-founder and CTO at Assembled, outlines the execution challenges leaders overlook when deploying AI support systems. AI tackles straightforward requests, but high-touch servi...