Updated for Claude Pro subscribers with Cowork access. Covers the recommended Readwise + Cowork stack, plus a fully no-cost alternative using Chrome and Claude in Chrome — both designed for a library of 50–100 files.
Before diving into tools, it helps to understand the underlying idea. Traditional search finds documents that contain your keywords. An AI knowledgebase does something more powerful: it understands your content and can synthesise answers across many sources at once — like having a research assistant who has read everything you've collected.
The technical term is RAG — Retrieval Augmented Generation. In plain language: when you ask a question, the system finds the most relevant pieces from your documents, then an AI model reads those pieces and writes you a synthesised answer with source references. You're not limited to "which document mentioned this?" — you can ask "what do my sources collectively say about X?"
Getting your content in — PDFs, web pages, newsletters, Word files, presentations, and Google Docs.
Your content lives in a designated folder on your Mac. Cowork reads files directly — no separate indexing step needed at your scale.
You open Cowork, describe what you want, and Claude reads your files and returns a synthesised answer drawn from your own material.
Why no vector database? At 50–100 files, a persistent vector index (like AnythingLLM uses) is overkill. Cowork can read your entire library on-demand within a single session — faster to set up, simpler to maintain, and no ongoing API costs on top of your Claude Pro subscription.
Given your Claude Pro subscription and Cowork access, there are two practical approaches. Both use Cowork as the query engine. The difference is how you capture and organise web content.
Readwise Reader handles web article and newsletter capture with a single browser click. Your content syncs to a local folder that Cowork reads from. Best capture experience, especially for newsletters and paid Substack.
Cost: ~$17 AUD/month (Readwise) + Claude Pro subscription
Best for: Heavy web readers, newsletter subscribers, anyone wanting a polished one-click save workflow
No extra subscription. You use Claude in Chrome (included in your Pro plan) to manually save article content into your knowledge base folder as you browse. More manual, but zero additional cost.
Cost: Claude Pro subscription only
Best for: Occasional web readers, those wanting to keep costs minimal, or as a trial before committing to Readwise
| Feature | Option A: Readwise + Cowork | Option B: Chrome + Claude in Chrome |
|---|---|---|
| Article capture speed | One click — browser extension saves instantly | Manual — 2–3 steps per article via sidebar |
| Paid newsletters (Substack) | ✔ Via email forwarding to Readwise inbox | ⚠️ Requires copying/pasting or forwarding manually |
| YouTube / podcast transcripts | ✔ Readwise Reader pulls transcripts automatically | ⚠️ Possible via Claude in Chrome but manual |
| Local files (PDF, Word, Excel, PPT) | ✔ Drop in folder, Cowork reads natively | ✔ Drop in folder, Cowork reads natively |
| Google Docs | ✔ Use Google Drive for Desktop to sync locally | ✔ Use Google Drive for Desktop to sync locally |
| iOS reading app | ✔ Readwise Reader has a full iOS app | ✘ No equivalent |
| Safari support | ✔ Readwise extension works in Safari | ✘ Claude in Chrome requires Chrome browser |
| Extra monthly cost | ~$17 AUD/month | None |
The stack: Readwise Reader captures web articles, newsletters, YouTube transcripts and podcasts with a single click, exporting them to a local folder on your Mac. Cowork reads that folder — plus your local PDFs, Word, Excel, and PowerPoint files — on demand. Two tools, zero overlap, 100% of your content sources covered.
Go to read.readwise.io — 60-day free trial, then ~$11 USD/month ($9.99 billed annually). Download the Mac app and the iOS app if you read on your phone.
Available for both Safari and Chrome. When you're on any article you want to save, click the extension icon — the full article is saved to your Readwise library instantly, formatted cleanly without ads or sidebars. This replaces your Safari Reading List going forward.
💡 One click saves = same speed as Safari Reading List, but queryable by CoworkIn Safari: File → Export → Bookmarks. This gives you an HTML file. In Readwise: Import → Reading List and upload it. Readwise will fetch the full content of each URL. Do this in batches of 100–200 to avoid timeouts.
In Readwise settings, find your personal inbox address (e.g. yourname@readwise.io). Forward your Substack and newsletter emails to this address. Because you receive the full article in your email as a paid subscriber, Readwise captures the complete content — no scraping required, no paywalls hit.
💡 Create a mail filter to auto-forward from substack.com and other newsletter domainsPaste any YouTube URL into Readwise Reader — it automatically fetches the transcript. For podcasts, paste the episode URL from a supported app. Both are saved as readable, searchable text that Cowork can query.
In Readwise settings, go to Export → Continuous Export → Markdown. Set the export folder to your Knowledge Base folder on your Mac (e.g. ~/Knowledge Base/Web Articles). Readwise will automatically export every saved article as a markdown file, keeping this folder in sync as you add new content.
Create a root folder on your Mac — e.g. ~/Knowledge Base — with subfolders by content type or topic. A simple starting structure:
~/Knowledge Base/
Web Articles/ ← Readwise exports here automatically
PDFs/
Word & Excel/
PowerPoint/
Google Docs/ ← synced via Google Drive for Desktop
Copy your existing PDFs, Word docs, Excel files, and PowerPoint presentations into the relevant subfolders. Cowork can read all of these natively — PDF, .docx, .xlsx, .pptx, .txt, .md, .csv. No conversion needed.
💡 Start with your most-used 20–30 files and add more over timeDownload Google Drive for Desktop from drive.google.com/drive/download. Once installed, your Google Drive files appear as a local folder on your Mac (typically at /Volumes/GoogleDrive or similar). Point a shortcut from your Knowledge Base Google Docs folder to this location, or simply note the path. Cowork can read from it directly.
Open the Claude Desktop app. Click the Cowork tab in the left sidebar. When prompted, grant access to your ~/Knowledge Base folder. Cowork will ask for confirmation before taking any action — you stay in control throughout.
Try a question like: "Read through all the files in my Knowledge Base folder and tell me what themes appear most frequently across my web articles and PDFs." Cowork will scan your files, synthesise across them, and return an answer drawn from your own material.
Anything you save in Readwise Reader is automatically exported to your Web Articles folder via the continuous export. Nothing to do — the next time you open Cowork, new articles are already there.
When you get a new PDF, Word doc, or spreadsheet you want in your knowledge base, simply move it into the relevant subfolder. No upload step, no sync required — Cowork reads directly from the folder each session.
Google Drive for Desktop keeps your local copy of Docs in sync with the cloud automatically. As you update a Google Doc, the local file Cowork reads updates too — no manual action needed.
When opening Cowork for a knowledge base session, be explicit about the folder: "Look through everything in ~/Knowledge Base and tell me..." or "Search my PDFs subfolder for anything about [topic]." Cowork can handle cross-folder synthesis and will tell you which files it drew from.
💡 Cowork uses more usage allocation than regular chat — if you hit limits, save complex queries for when your allocation resetsWho this is for: If you don't want an extra subscription, or you want to try the system before committing to Readwise, this approach uses only tools included in your Claude Pro plan. The tradeoff is that saving web articles requires a few more manual steps per article, and you'll need to switch from Safari to Chrome for browsing.
Key requirement: Claude in Chrome is a Chrome browser extension — it does not work in Safari, Firefox, or other browsers. If you primarily browse in Safari, Option A (Readwise) is the better fit, as the Readwise extension supports Safari.
Go to claude.com/chrome and click Install. This adds Claude as a sidebar panel accessible from any Chrome tab. Sign in with your Claude Pro account.
Create the same folder structure as Option A on your Mac: ~/Knowledge Base/ with subfolders for Web Articles, PDFs, Word & Excel, PowerPoint, and Google Docs.
Open Claude Desktop, go to Cowork, and in Settings enable the Chrome connector. This links Claude in Chrome with your Cowork session so browser-captured content can be saved directly to your folder.
This is the key manual step that replaces the one-click Readwise save. It takes about 30–60 seconds per article once you're used to it.
Browse to the article you want to save as you normally would.
Click the Claude extension icon in your Chrome toolbar, or use the keyboard shortcut. The Claude panel opens on the right side of your browser.
Type a prompt such as: "Read the article on this page and save it as a markdown file in my ~/Knowledge Base/Web Articles folder. Use the article title as the filename and include the URL and today's date at the top."
Claude will read the page content, clean it up (removing ads, nav menus, and footers), and write a clean markdown file directly to your folder via Cowork.
💡 Save this as a Cowork shortcut or skill so you only type it once — run /save-article each time after thatCowork will show you the planned action (create file X in folder Y) and ask for your approval before writing. Click confirm. The article now lives in your Knowledge Base folder as a clean, readable markdown file.
When you want to query your knowledge base, open Cowork in Claude Desktop and ask away — the saved articles will be read alongside your other local files. The experience from this point is identical to Option A.
Limitations to know about with Option B: Paywalled content (paid Substack, premium articles) cannot be fully read by Claude in Chrome if the page requires a login and you aren't already signed in. For newsletters, you'd need to open the email in Chrome and save from there. YouTube transcripts require asking Claude to extract them from the page — possible but an extra step. There is no iOS equivalent — mobile reading stays in Safari or another app and doesn't flow into your knowledge base.
To avoid re-typing the save instruction each time, you can create a Cowork skill that runs with a single command. In Cowork, go to Skills and create a new skill called save-article with the instruction: "Read the currently open Chrome tab, extract the article content, and save it as a clean markdown file to ~/Knowledge Base/Web Articles/ using the article title as the filename, with the URL and date in the header." Type /save-article in the Claude in Chrome sidebar whenever you want to capture a page.
| Content Type | Option A: Readwise + Cowork | Option B: Chrome + Claude in Chrome |
|---|---|---|
| Web articles | One-click save via Readwise browser extension (Safari or Chrome). Auto-exported to your Web Articles folder. | Open article in Chrome → use Claude sidebar to save as markdown to Knowledge Base folder. ~30–60 sec per article. |
| Paid newsletters (Substack) | Forward email to your Readwise inbox address. Full article captured automatically including paywalled content. | Open the email in Chrome and use Claude in Chrome to save it. Or copy content manually to a text file in your folder. |
| YouTube videos | Paste the YouTube URL into Readwise Reader — transcript fetched automatically and exported to your folder. | Navigate to the YouTube video in Chrome, open Claude sidebar, ask it to extract and save the transcript. |
| Podcasts | Paste the episode URL into Readwise Reader — transcript captured if available. | Most podcasts require a transcript source. Paste a transcript from a provider like Podscribe or Otter.ai as a text file into your folder. |
| PDFs | Drop into ~/Knowledge Base/PDFs/ subfolder. Cowork reads natively. | Same — drop into the PDFs subfolder. Identical experience. |
| Word documents (.docx) | Drop into ~/Knowledge Base/Word & Excel/ subfolder. Cowork reads natively. | Same — identical experience. |
| Excel spreadsheets (.xlsx) | Drop into ~/Knowledge Base/Word & Excel/ subfolder. Cowork reads natively. Note: works best with clean tabular data, not presentation-style spreadsheets with merged cells. | Same — identical experience, same caveat on structure. |
| PowerPoint files (.pptx) | Drop into ~/Knowledge Base/PowerPoint/ subfolder. Cowork reads the text content of slides. Diagrams and charts are not interpreted. | Same — identical experience. |
| Google Docs | Install Google Drive for Desktop — Docs appear as local files on your Mac. Cowork reads them from the Drive for Desktop path. (Note: Google Drive MCP connector not yet supported directly in Cowork.) | Same approach — Google Drive for Desktop is the current workaround for both options. |
| Google Sheets / Slides | Google Drive for Desktop syncs these locally. Cowork can read the exported format. Alternatively, download a specific Sheet as .xlsx and place in your folder. | Same approach. |
| Safari Reading List (existing) | One-time import: File → Export → Bookmarks in Safari, then import the HTML file into Readwise Reader. Readwise fetches full article content for each URL. | Safari Reading List cannot be directly exported to a folder in a usable format. Manually re-open important articles in Chrome and save them one by one using the Claude in Chrome workflow. |
Cost tip: Readwise offers a 60-day free trial — you can trial Option A for two months at no extra cost. Use that time to judge whether the one-click article capture is worth ~$17/month to you versus the manual Chrome workflow. If you read fewer than 5–10 articles per week, Option B may be perfectly sufficient.