The Skill Tree

Nick Nisi and Neil Roberts

The Skill Tree is a podcast about AI skills, agents, developer workflows, and practical ways to use LLMs. Neil Roberts and Nick Nisi talk with developers, tool builders, and creatives about prompt engineering, evals, scripting, tooling, MCP, and the systems people use to make AI actually useful.

Episodes

  1. 2d ago

    I Haven't Given It a Soul

    Episode 2 of The Skill Tree is a hosts-only catch-up where Neil Roberts and Nick Nisi trade notes on a fast-moving few weeks in AI coding tools. They dig into the Ralph Loop arriving as a /goal command, the personal utilities they are each building around their agents, the industry's drift from Markdown to HTML for agent output, and a genuinely unnerving npm supply-chain worm. The conversation is less about any single tool and more about the workflows forming around them. Nick walks through a session-search tool he built to fuzzy-find across every Claude, Pi, and Codex transcript he has ever run, and Neil describes the Dockerized, mobile-first OpenCode setup he wired to Readwise Reader, Tailscale, and a synced Obsidian vault — a rig so pleasant to use that Nick asks whether he has accidentally built his own OpenClaw. "I haven't given it a soul," Neil says. In This Episode Where looping agents like the Ralph Loop (/goal) actually help, and where the context window still gets in the way The small cross-tool utilities worth building yourself: Nick's session-search tool and Neil's mobile agent stack Why the AI crowd is rediscovering web development — external stylesheets, token budgets, and Cloudflare Code Mode — as agent output shifts from Markdown to HTML The npm supply-chain worm Shai-Hulud, its dead man's switch, and what it does to your trust in npm install Episode Chapters 00:00 An Honor Just to Be Nominated 01:02 Notion, Obsidian, and Claude Writing Your Docs 01:57 The Ralph Loop Arrives as /goal 07:31 Nick's Sessions Tool: Searching Every Transcript 12:11 Walled Gardens: CLAUDE.md vs AGENTS.md 15:10 Chasing Subagents Across Pi and OpenCode 19:01 Broken Agent IDEs and "Everything's Vibe Coded" 21:11 The TanStack Attack and Shai-Hulud 22:03 OpenCode Go, ChatGPT, and Claude's $20 Plan 23:08 The Unreasonable Effectiveness of HTML 27:40 Constraints, Cloudflare Code Mode, and Throwaway Scripts 31:28 npm Supply-Chain Fear and the Dead Man's Switch 32:38 Neil's Dockerized Mobile Stack 38:07 Is It an OpenClaw? Hermes, Raindrop, and OpenCode 42:42 Outro: Procrastination and Intuitive Living When Looping Agents Earn Their Keep The episode opens on the Ralph Loop — the trick of running an agent in a while-loop against the same prompt — showing up as a first-class /goal command in both Codex and Claude. Nick recounts pointing it at a real task and watching it report back, "I have been running for an hour and three minutes. Goal achieved." Neil counters with a non-loop version of the same instinct: using Maestro end-to-end tests to let an agent iterate on his React Native app until the Android build actually worked. The useful part is where they draw the line. Looping shines on deterministic, verifiable workflows, and falls down where the context window does. That tension — between letting an agent grind autonomously and keeping it on a short enough leash to stay accurate — runs under most of the tools they discuss. Building Your Own Tools Around the Agents Both hosts have started treating their agents as platforms to build on. Nick's session-search tool indexes every Claude, Pi, and Codex transcript into SQLite — even across deleted worktrees — so he can fuzzy-find that thing he did last week, and he wraps it in an MCP server so the agents can search their own history. Neil's project is a Docker Compose stack he can drive from his phone: OpenCode's web server behind Tailscale, VS Code and a couple of web file browsers, and a Readwise Reader pipeline that summarizes saved articles through an agent and files them into a CouchDB-synced Obsidian vault as a daily "dispatch." It is the moment Neil describes that setup — nice enough that Nick asks if it is "an OpenClaw" — that gives the episode its title. The throughline is that a lot of the value now comes from the unglamorous plumbing you assemble yourself, not the model. Markdown, HTML, and Rediscovering the Web The back third turns to a shift in how agents are told to produce output: away from Markdown and toward HTML. Nick brings up Thariq Shihipar's post on the unreasonable effectiveness of HTML, and the two connect it to Cloudflare Code Mode, where forcing the model to write one throwaway TypeScript script instead of many tool calls cut token usage by nearly 90%. Neil's read is that the whole industry is watching people rediscover web development — external stylesheets, image optimization, token budgets as the new bandwidth constraint — and that the right response to repetitive work is often to have the machine write a small script and move on. Threaded through it all is a real note of supply-chain dread: the self-propagating npm worm Shai-Hulud, and the dead man's switch that would wipe a home directory if it detected you rotating your GitHub token. It is a good reminder that the same ecosystem making all this possible can still bite hard. Tools, Projects, and References Mentioned Ralph Loop and /goal - running an agent in a loop against one prompt, now surfaced as a slash command in Codex and Claude OpenCode (and OpenCode Go) - the provider-agnostic terminal agent, web server, and open-model tier at the center of Neil's mobile setup Pi, Codex, Devin, Warp, and Hermes - the other agents and IDEs the hosts are poking at, from PR-comment automation to Nous Research's agent framework Maestro - the YAML-driven mobile end-to-end testing tool Neil used to fix his React Native app Cloudflare Code Mode, Flue, and Astro - the Cloudflare-flavored thread on typed SDKs, sandboxed TypeScript agents, and Fred Schott's team Readwise Reader, Obsidian, CouchDB, Tailscale, and Raindrop.io - the personal-knowledge and networking plumbing behind both hosts' automations Shai-Hulud - the npm supply-chain worm and its credential-rotation dead man's switch Related Listening They're All Markdown Files Cleaning the Fridge: The Hero's Journey

  2. Mar 31

    Cleaning the Fridge: The Hero's Journey

    Episode 1 of The Skill Tree is a conversation with Nick Cannariato about how people actually use Claude skills once they move past the toy stage. Neil Roberts and Nick Nisi talk with him about narrative frameworks for talks and blog posts, connector-heavy research workflows, skill generation, memory systems, and the strange mix of control, curiosity, and frustration that makes AI-assisted work productive. The discussion stays practical even when it gets philosophical. Nick C explains how his post and talk skills grew out of a dislike for one-size-fits-all story structures, how he uses Claude connectors to automate real sales and research work, and why the right response to repetitive work is often to tell the machine to do more of it. In This Episode Why Nick Cannariato built post and talk skills around 22 narrative frameworks instead of defaulting to the Hero's Journey How Claude connectors, skills, and long-running agents help automate research, deal prep, documentation, and internal workflows What Nick Nisi's Case project is trying to prove about evidence, state machines, memory, and AI-assisted software work Why all three hosts see AI less as a replacement for thinking and more as a way to ship faster, learn faster, and reduce the fear of getting started Episode Chapters 00:00 Opening, Guest Intro, and the Cult of Skills 01:04 Meet Neil and Nick Nisi 03:50 Ideation, Pi, and the New Skills 04:11 Monomyths, Story Circle, and 22 Narrative Frameworks 08:44 What the Post and Talk Skills Do in Practice 10:23 Born Out of Spite 11:05 Connectors: Slack, Gong, Notion, and Deal Research 13:35 Meta-Skills, skill-forge, and Hidden Anthropic Docs 16:27 How Nick C Organizes His Skills 18:28 Case, Evidence, and AI State Machines 20:56 Auto-Dream Mode and Memory Management 23:34 Stealing Ideas, Markdown Files, and bat-kol 26:35 Evernote, GitHub, and Becoming an Engineer 29:06 AI Anxiety vs. Shipping More Than Ever 33:35 The Thursday Estimate That Shipped Monday 37:21 Why AI Fits How Our Brains Learn 38:12 The Blog-Writing Hack: Mine Your Claude Transcripts 39:51 Parting Advice 42:53 Break Stuff and Get Paid to Fix It Narrative Frameworks Beyond the Default Arc Nick C explains that his post and talk skills were built as a reaction against forcing every talk or blog post into the Hero's Journey or Story Circle. Instead, he has Claude choose from a larger set of narrative frameworks, including more technical, absurdist, and open-ended structures that better fit conference talks, support stories, and real-world writing that does not resolve into a clean heroic arc. This part of the episode gets into something bigger than presentation structure. The hosts are really talking about taste: how much of yourself you want to preserve when AI helps you write, and how a good skill can encode preferences that are hard to express in a single prompt. Skills as Working Automation, Not Just Prompts One of the clearest through-lines in the episode is that skills become more valuable when they are attached to actual work. Nick C walks through using Claude connectors with Slack, Gong, and Notion to recover context from meetings, assemble research, and update documentation without having to manually retrace everything himself. That same impulse shows up in his skill-generation workflow, where one skill helps tune and improve other skills. Nick Nisi describes a parallel idea in Case, his system for taking issues from intake through implementation while still requiring evidence that the work really happened. Between the two approaches, the episode draws a useful line between lightweight reusable instructions and heavier orchestration systems that manage agents, memory, and proof. Learning Faster Without Pretending the Tradeoffs Are Gone The last third of the conversation shifts into what AI work feels like day to day. The hosts talk about shipping faster, using Claude as a patient collaborator for exploration, and reducing the fear that used to come with unfamiliar code or vague estimates. At the same time, they acknowledge the tradeoffs: trust has to be calibrated, review still matters, and some kinds of craft can atrophy if you stop caring about the underlying systems completely. What makes the conversation useful is that nobody treats this as abstract future-of-work discourse. The examples stay grounded in real projects, real habits, and the way these tools change how people learn by letting them revisit a problem in layers instead of having to understand everything at once. Tools, Projects, and References Mentioned ideation - Nick Nisi's skill for turning rough ideas into clearer implementation artifacts Pi - another coding agent environment that comes up as a comparison point for Claude Code new-post and conference-talk-builder - Nick Cannariato's skills for generating posts, talks, and narrative structure Slidev and Rough Notation - tools behind Nick C's talk-generation workflow and presentation styling Slack, Gong, and Notion - the connectors and systems that make Claude useful for real work beyond local coding Case and Playwright - Nick Nisi's evidence-driven system for automated implementation and verification skill-forge, octoflow, and bat-kol - examples of meta-skills, Git workflow hooks, and voice-tuning experiments Nick Cannariato Nick Cannariato is a software engineer at WorkOS with a background in support, product development, and technical writing. In this conversation he brings a strong point of view on automation, storytelling, and what happens when people who were never traditional software engineers suddenly have tools that let them build and ship anyway. Related Listening They're All Markdown Files

  3. Mar 13

    They're All Markdown Files

    In this trailer episode of The Skill Tree, Neil Roberts and Nick Nisi talk about why they started the show and the kinds of AI workflow conversations they want to have. The discussion centers on skills as reusable Markdown-backed instructions, transcript-first publishing, and the tools they keep returning to in day-to-day work. The format is intentionally loose. There is no formal intro or outro, and the episode drops straight into a conversation about ideation workflows, spec generation, evaluation, and the mix of tools shaping how the hosts think about agent-assisted development. In This Episode Why The Skill Tree exists and what kinds of conversations the show is meant to explore How Neil and Nick think about AI skills as practical workflow building blocks What makes a strong ideation and spec-generation workflow for agentic coding Why transcripts, reference files, and structured Markdown can make audio content searchable and reusable Episode Chapters 00:00 Under the Skill Tree 02:34 How Skills Clicked 04:30 NebraskaJS and the Birth of Ideation 15:40 DeepWiki as a Skill Generator 19:01 Open Models, Cost, and Harnesses 23:31 Guests, Segments, and the Show Format 25:35 skilltree.fm, Podcast Metadata, and Skill Evals Discussion Highlights Starting with a loose trailer episode Neil and Nick use this first episode to start publishing before every segment, workflow, and production habit is locked in. That makes the episode feel more like an initial conversation than a polished pilot, but it also gives a direct introduction to the show's focus: practical AI workflows, developer tooling, and how these systems hold up in real use. Why skills matter even when they are "just Markdown files" One of the recurring ideas in the episode is that the format is simple but the structure is useful. When instructions, references, and workflows are organized clearly, they become reliable inputs for both agents and humans. The conversation treats skills less like magic and more like reusable working instructions. "They're all markdown files. What does this even do?" That line captures a lot of the episode's framing. A big part of the discussion is about the gap between a plain file format and the workflows it can support when the structure is good enough. Ideation as a bridge from rough ideas to implementation Nick's ideation skill is one of the clearest examples in the episode of how a workflow can improve AI-assisted development. Instead of jumping straight to an answer, the skill asks clarifying questions, checks its understanding, builds a contract, and only then expands into specs or PRDs. That creates a better handoff between rough human intent and concrete implementation work. Neil and Nick frame this as an interface problem as much as a prompting problem. Better systems come from better scaffolding: rubrics, progressive disclosure, execution phases, review loops, and artifacts that other tools can consume. Tools and systems shaping the conversation The episode moves across a wide range of tools, from day-to-day coding environments like Cursor to research and execution layers like DeepWiki, Context7, Mastra Code, Agent Zero, and pi.dev. NebraskaJS enters the story as a proving ground for showing workflows in public. Wispr Flow connects to the dictation-heavy, brain-dump style behind ideation. DSPy and Tessl push the conversation toward evaluation and what it means to know a generated workflow is actually good. Tools, Projects, and References Mentioned Cursor - the coding environment both hosts keep returning to for AI-assisted development NebraskaJS - the meetup where workflow demos and the ideation origin story took shape Wispr Flow - the dictation tool behind the freeform brain-dump style that inspired ideation DeepWiki - a way to turn repository documentation into structured references and skill inputs Oxlint and Oxfmt - examples of tools Nick was manually experimenting with while thinking about what still feels good to do by hand Context7, Mastra Code, Agent Zero, and pi.dev - examples of agent tooling and execution harnesses that shape the discussion DSPy and Tessl - part of the thread on evaluating skills, workflows, and generated systems About The Hosts Neil Roberts Neil Roberts is a software engineer at SitePen active in the JavaScript community and podcasting. On The Skill Tree, he brings a strong interest in AI workflows, documentation-driven systems, and practical ways to make LLMs more useful. Nick Nisi Nick Nisi is a DX engineer at WorkOS focused on TypeScript, AI tooling, and podcasting. He brings a tinkerer mindset to the show, with a particular interest in skills, agent workflows, ideation systems, and developer tooling.

Trailer

About

The Skill Tree is a podcast about AI skills, agents, developer workflows, and practical ways to use LLMs. Neil Roberts and Nick Nisi talk with developers, tool builders, and creatives about prompt engineering, evals, scripting, tooling, MCP, and the systems people use to make AI actually useful.

Information

  • Creator
    Nick Nisi and Neil Roberts
  • Years Active
    2026
  • Episodes
    3
  • Rating
    Explicit
  • Copyright
    © 2026 Driftful
  • Show Website
    The Skill Tree