Tom OS: How AI transformed my workflow in a weekend
Can AI help you streamline your workflow? If there’s nothing off-the-shelf that works, it’s easier than ever to build something bespoke.
A few years ago, I decided to see if AI could help me streamline my workflow. And honestly? I didn’t come up with much beyond the obvious and boring. Capture meeting minutes? Great.
But this year is looking like it’s going to be my busiest year ever. With lots of concurrent projects, as well as running Pomona Partners and The Kartel, I decided my workflow could do with an upgrade. So this weekend, inspired in part by James O’Malley’s post about how he has been using AI to improve his work, I fired up Claude Code and decided to build my own personal operating system. Not an OS like Windows, but rather a single app and interface to bring together some of the critical information and processes in my working life.
I’ve named it, rather boringly, Tom OS (again O’Malley inspired). But do you know what? It’s amazing.
Integrated Workflow
Tom OS brings together my kanban-style todo list (I’ve been using Trello for years for this), with tracking of enquiries and their transition into projects, with a deep AI-powered index of all my historical work. And it puts a generative AI layer over the top of all that information.
The result is that I can do clever things like this:
When a new enquiry comes in to my website, it is automatically tracked in Tom OS.
When it converts, I can create a Project from it.
Projects have type-specific workflows. For example, if it’s a speaking gig, starting a new project will create a sequence of tasks like “Collect Brief”, “Confirm Logistics”, “Research”, “Slide Deck/Script” and “Follow Up”
AI automatically contributes to each of those actions. For example:
it takes everything we know about the project from the original enquiry and packages it into a Brief document with some prompts for critical missing information.
In the research phase it looks through my historical work in the same domain/subject areas, finds me past scripts, papers and slide decks that I have written, as well as looking at the event agenda and summarising themes, and gives me a summary of the latest news in that space.
It is this last piece that is the real time-saver. I’ve produced a massive volume of written work and presentations over the last twenty years, including lots of custom slides and diagrams, endless stats research, Intersections exercises, and theories. If I can cut even 20% of the time I spend at the start of a new project looking back through old ones, it will be really valuable.
Tell me what to do
Alongside this, Tom OS is integrated with my email and calendar, allowing Gemini to look at those and give me a summary of my tasks for the day, including my todo list (and any overdue items). And it’s integrated with my billing system, allowing me to track projects consistently through from first enquiry to invoice and beyond.
There are a few other features I’m going to build-in as well. I still spend too much time doing manual finance stuff, like making sure I’m saving the right amount for future tax bills. I’m going to automate a lot of that and probably a few more things as well as time goes on.
But for now this feels like a real, practical upgrade to my working practice. And all built in the space of a weekend thanks to AI.