I finished writing Founder Unfriendly in August of last year. Between then and now, something changed.
Not the fundamentals of fundraising — those haven't moved. What changed is the toolset you're working with. When I was writing the book, AI was a novelty you could use to draft an email or generate a first pass at something. It wasn't yet a real thought partner, a research engine, or a working prototype machine.
It is now.
The analysis in the book stands. The self-assessment questions, the investor psychology, the pitch mechanics — all of it. But there's a layer of practical acceleration available to founders today that simply didn't exist in the version of the world I was writing for. This companion guide adds that layer.
The goal isn't to replace the book. It's to help you use the book faster, go deeper on the parts that matter most to you, and build things you used to need a team or a budget to build.
A note on tools: Claude does everything in this guide pretty well — research, writing, simulation, analysis, pitch prep. Some tools have specific advantages for specific tasks (Granola for meeting transcription, NotebookLM for synthesizing large document sets, Lovable for building apps), and we'll call those out where they matter. But for the core exercises, Claude handles it all. More importantly, if you use Claude consistently across every exercise, it builds context about your startup over time — your stage, your market, your investors, your thinking. That compounding knowledge makes every subsequent prompt smarter. If you have a tool you prefer, use it. But if you're starting from scratch, just use Claude.
The tools referenced in this guide:
- Claude (claude.ai) — everything. Start here, stay here. If you connect Google Sheets via MCP in Claude's settings, Claude can write directly to your spreadsheets — no copy-pasting needed. Same for Gmail, Google Drive, and other tools. Setting up MCPs once at the start makes every exercise that outputs structured data hands-free.
- Granola (granola.so) — meeting transcription. Runs in the background, feeds transcripts to Claude.
- NotebookLM (notebook.google.com) — upload a set of documents, videos and websites and have a conversation with all of them at once. Great for ingesting podcasts that post to YouTube.
- Lovable (lovable.dev) — build a working app from a plain-English description.
