After experimenting with Obsidian as a vault system for indexing and organising my business folders — TestVentures.net — I was pretty happy with it. So this morning, I went a step further and organised all of my writing for the Finn Wardman World Explorer Fund. The charity paperwork. The legal framework. The blog posts. A manuscript I'd started writing in Finn's honour. Four years of journal entries. Then I'll turn on both Dropbox and iCloud as cloud-based backups and have my life in two buckets, or vaults. Business (TestVentures) and the mission (Powered by Finn). Both tied together.
I've totally moved away from Projects in Claude chat on the web, which kind of sucks. Now I'm using the vault-based system with Obsidian and Claude Cowork. It's working great right now.
If you're curious about how this can work together and what it does, here's how I did it.
While the entire process took 45 minutes to setup, the part that actually needed my input was about 20 minutes. Then I told claude (Opus 4,6, the only model I really trust now) to run things while I took the dogs out for a 20 minute walk. When I came back, everything was done. Seriously, people complaining about AI? What's so bad about that?
Here is what I did and why I did it. I do go a bit into my technical setup for the site (this one) which I run for free and do all posting auto synced with Claude, and run deployements only using the CLI tool. Never from cowork. I'll do a post on that later probably because I'm also happy with this setup and I get hosting for free. Who wouldn't want that?
The problem: everything was everywhere
Everything related to Finn's foundation was scattered across multiple folders on my Mac. The Ghost theme repo for finnwardman.com had blog post drafts mixed in with website code. A separate folder called Finn Fund held four years of charity registration paperwork, grantee testimonials, financial records, branding assets, and videos — all dumped flat or nested in folders named by year rather than by function. The manuscript chapters for Full Cup / Empty Cup and the Vipassana book lived in a third location entirely. None of it was connected. None of it was searchable. And none of it had a backup strategy.
Sound familiar? Most founders have some version of this. Not necessarily grief and manuscripts, but the scattered folders, the duplicate files, the "I know it's somewhere" problem. The business version of this was what I solved yesterday with the TestVentures vault. Today I solved the personal version.
What I built
I created a single Obsidian vault called Powered by Finn with six numbered sections. A dashboard for tracking state across sessions. A writing section holding blog posts, manuscript chapters, journal entries, and letters. A foundation section covering grants, legal, finance, strategy, branding, and media. A personal Finn section for photos, stories, and timeline material. A reference section with voice guides, templates, and a scene index for the manuscript. And the Ghost theme code for finnwardman.com in its own contained folder.
The writing section is the heart of it. Seven possible chapters, nine Vipassana chapters, and nine blog post drafts all sit alongside four years of journal entries. When I'm working on the manuscript in Obsidian, I can search across the journals for a specific scene or memory and cross-reference it with the chapter drafts using wikilinks. That wasn't possible when the content lived in four different places.
How it works with Claude
This is the part that makes it an operating system and not just a folder structure.
Each vault has a session protocol. When I start a new Cowork session and mount the vault, Claude reads three files: the vault README (how this vault works), a dashboard (30-second snapshot of where everything stands), and the last session handoff (what we did, what's next). That means I never re-explain context. Claude picks up where we left off.
The foundation sort is a good example. The Finn Fund folder had 97 files covering three years of charity registration — including a denial from the Bermuda registrar, an appeal, and a re-registration — plus grantee acceptance letters and testimonials from five recipients, payment records, fund agreements, social media campaign plans, and branding assets. Claude sorted all of it by function into Legal, Finance, Grants, Strategy, Branding, and Media subfolders. Nothing was deleted. Everything is now findable. That took about 10 minutes.
The Ghost theme for finnwardman.com moved from the vault root into a dedicated folder. The deploy script and GitHub Actions workflow were updated to work from the new path. The vault folders are all gitignored so Git only tracks the website code. The theme still deploys the same way — push to main or run the script.
For the Finnwardman.com site, I use ghost, because I love the blogging aspect of it. This is a guy that used Wordpress for about 10 years. I will NEVER use that again. Ghost is really clean and easy to use. If you're thinking about it for your own stuff, depending on your purpose, I am really happy with it.
The backup
A daily rsync script copies the vault to both Dropbox and iCloud, excluding the Git repo, Obsidian config, and any credentials. Two cloud services, one-way sync, no conflict risk. If my Mac dies tomorrow, the vault is in two places.
Two vaults, one system
TestVentures.net handles the business — clients, prospecting, the Build in Public blog, daily operations. Powered by Finn handles the mission — the foundation, the writing, the manuscript, Finn's legacy. Both use the same structure. Both have persistent memory across Claude sessions. Both are backed up.
The vaults are the operating system. Obsidian makes them searchable and navigable for me. Claude makes them actionable. Everything I need to write, run the foundation, or update the website is in one place, connected, and backed up.
If you're building something that has more than one dimension — a business and a side project, a company and a book, revenue work and mission work — this is how you keep both alive without one always eating the other. Separate vaults. Same system. Same AI memory.
Day 4 numbers
Revenue: $0. Clients: 0. Prospects: 3, with another possible.
Day 5 tomorrow.