Worktrees

Jack Bogdan and Chris Messina unpack ⁠Raycast 2.0’s shift away from a purely native Mac architecture⁠, the ⁠backlash from power users⁠, and what cross-platform ambitions mean for modern app development.

They also dive into Jack’s new project ⁠Recursive⁠, an agentic IDE built around plugins, local file-based workflows, multiple AI coding providers, session replay, autonomous commits, and self-debugging loops. Jack demos how Recursive helps him build and improve his own apps — including ⁠Click⁠ — by automating crash analysis, performance benchmarking, and iterative fixes.

Chris shares his new Coaster project for analyzing iOS app updates, and the conversation expands into how AI model companies may compete with vertical software — including Jack’s finance app prototype built on the same Recursive foundation.

A wide-ranging episode on native vs web architectures, AI-assisted development, vertical workspaces, and what it means for software to increasingly build, explain, and improve itself.

Jack Bogdan and Chris Messina unpack Raycast 2.0’s shift away from a purely native Mac architecture, the backlash from power users, and what cross-platform ambitions mean for modern app development.

They also dive into Jack’s new project Recursive, an agentic IDE built around plugins, local file-based workflows, multiple AI coding providers, session replay, autonomous commits, and self-debugging loops. Jack demos how Recursive helps him build and improve his own apps — including Click — by automating crash analysis, performance benchmarking, and iterative fixes.

Chris shares his new Coaster project for analyzing iOS app updates, and the conversation expands into how AI model companies may compete with vertical software — including Jack’s finance app prototype built on the same Recursive foundation.

A wide-ranging episode on native vs web architectures, AI-assisted development, vertical workspaces, and what it means for software to increasingly build, explain, and improve itself.

Generative interfaces, vibe-coded desktop apps, and Jack's attempt to build agent workspaces for every domain.
We opened with Flipbook, a generative visual web experiment where pages are rendered as AI-generated images instead of traditional HTML interfaces. The bigger question: what happens if software skips GUI frameworks entirely and models generate visual UI directly?

• Flipbook

• X-Pilot

• Coverage: Flipbook as a generative visual internet

Chris tested Claude Design for slide creation and found the output visually polished but practically unusable. The discussion centered on design as intent, not aesthetics: Claude handled fonts and colors well, but missed constraints, hierarchy, format, and density.

• Claude Design

• Mike Krieger leaves Figma’s board

• Figma

We talked through Glaze, Raycast’s new AI app builder, and Chris’s attempt to recreate a Ring camera desktop/menu bar app from a PRD. Glaze produced a functional TypeScript app shell, but authentication, live data, OAuth, and polish remain open challenges.

• Glaze

• Raycast

• Ring App Store

• Ring Live View

• Fly.io

Jack proposed testing Glaze with an FFmpeg wrapper: a simple drag-and-drop video converter with presets. The point was to see how far these AI-built app platforms can reach beyond mock UI and into real local tooling.

The results were not bad with a one-shot prompt!

• FFmpeg

• Permute

Jack shared progress on Recursive after 1,500+ sessions using it as his primary development environment. The next step is abstracting the core into a monorepo so the same agent workspace, inbox, plugin system, automations, and tooling can power vertical apps for finance, writing, marketing, and more.

• Obsidian

• Model Context Protocol

• Copilot Money

• Xcode

The episode closed with a quick Click update: new builds are ready, but Apple review and TestFlight checks have slowed distribution to testers. The conversation touched on how review processes may be getting stricter, especially around privacy-sensitive app behavior.

• TestFlight

• Apple Developer

In this episode we talk about what happens when the models get so good that you become the bottleneck. We dig into the foundations that let you actually leverage AI for native development, how to organize a massive codebase for agents, the insane list of features shipped in a few days, why Jack is building an automated CI/CD pipeline for content and docs, personalized release notes, and a brand new offline voice-controlled D&D experience called DM.MD.