Podcast/Weekly/Oscar & Matt

Human in the Loop

A weekly signal filter for the AI economy. Oscar and Matt sift the week's noise, debate real business ideas, and close with two hot takes you won't hear anywhere else.

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Now Playing/EP 07

Cursor's $0.50 Coding Model + Anthropic's $900B Round

May 26, 2026·98 min·Available on Spotify & YouTube

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LatestEP 07

Human in the Loop

May 26, 202698 min

Cursor's $0.50 Coding Model + Anthropic's $900B Round

Cursor just shipped a coding model that matches Claude Opus 4.7 at one tenth the price, built on an open Chinese base model. The same week, Anthropic is closing a $30B round at a $900B valuation. If frontier coding got commoditized in seven days, what is anyone paying premium for? Welcome to Human In the Loop, a weekly podcast where two builders cut through the AI hype cycle. No breathless hype. No doomerism. No surface-level recaps. Honest, opinionated conversations from people actually building with AI.

May 19, 202692 min

Anthropic Killed the AI-for-SMB Playbook + AI Agents 101

Three months ago on Episode 1, we asked if there was a real business in selling AI to small businesses. This week, Anthropic shipped it themselves. So we just watched the founder playbook get eaten by a frontier lab in 90 days. If you were six weeks into building that company, what do you do Monday?

May 12, 202676 min

Self-Hosted AI, Everything You Need to Know

Anthropic and OpenAI are burning billions and your token bill is climbing. Oscar and Matt sit down with the show's first guest — Jackson Oaks, founder of RecursionAI and the self-hosted platform Courier — who's running production AI workloads for SMBs on Mac Minis. No NVIDIA. No per-token billing. Bootstrapped and profitable today. They get into the 80/20 of open-source AI, the Apple M-series long bet, a Fortune client who paid Big Four six figures for a glorified GPT wrapper, and a 14B open-source model that beat GPT-4o on a real production task. Three hot takes close it out — one says Anthropic and OpenAI don't exist in their current form three years from now.

May 5, 202672 min

9 Seconds to Delete a Database

An AI agent deleted a company's entire production database in 9 seconds — backups included — then confessed. Oscar and Matt break down what actually happened, what every team shipping agents needs to fix today, and why Anthropic took funding offers at a $900B valuation five days later. Plus three real startup ideas pulled from YC's Summer 2026 RFS. Steelman. Pushback. Verdict. No fence-sitting.

Apr 28, 202661 min

GPT-5.5 Ships, Mythos Loses a Round

OpenAI shipped GPT-5.5, DeepSeek V4 went open-source on the cheap, and Google just bet $40B on Anthropic. Oscar and Matt walk through the developer tools they're actually using, then split on the takeaway: open-source won the cost war but lost credibility, or frontier releases are quietly turning into incremental software updates.

Apr 21, 202662 min

The Second Best Model You Can Actually Buy

Anthropic shipped Claude Opus 4.7 — but the best model most people can actually touch still sits a tier below. Oscar and Matt unpack context engineering, agentic AI, and frontier model tiering in plain English, debate the business ideas hiding in the noise, and close with two hot takes.

Apr 14, 202647 min

The Model Anthropic Refused to Ship

Anthropic unveiled Claude Mythos Preview — then refused to release it. Responsible scaling, or enterprise GTM dressed up as safety PR? Oscar and Matt filter the week, debate three real business ideas, and close with two hot takes.

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Human in the Loop is produced by VallySeed