A 4-week cohort for founders who are using AI tools but haven’t built the system around them yet.
Format
Live workshop
With Tim Barker and
Mark Littlewood
Cohort
Max 12 founders
No observers, no spectators
Schedule
Weekly · 11am UK
Wednesdays, four weeks
Starts
23 September
Doors close at 12 seats
You’ve got agents running. Maybe Claude, maybe others. They’re doing useful things, writing drafts, summarising documents, handling tasks you used to do yourself.
But you don’t have visibility into what they’re deciding. You don’t have rules they’re required to follow. You don’t have a way to hand context from one session to the next without starting from scratch. And if something goes wrong, you have no record of what was authorised.
This workshop is for founders at that exact inflection point: AI tools in use, no governing system in place.
You arrive with your operating system already built. Over four weeks, you put it to work: two running missions doing something real for your business by the end.
Want to discuss fit before registering? Email mark@businessofsoftware.org
What you get
Bootstrap first, before Week 1: run it on your own, and you’ll have a working CLAUDE.md and OS folder structure by the time the cohort starts.
Four two-hour sessions, one a week.
SESSION 01
Mission Impossible
How the workshop runs, how the system stays safe by default, no external comms or commitments without your sign-off. We look at what Bootstrap actually produced for people in the room. Homework: run the workshop skill.
SESSIOn 02
Mission in Action
What Bootstrap and the workshop skill between them surfaced as worth acting on in your business. The session closes by casting and specifying the agent your first mission needs. Homework: shape that into a running mission.
SESSIOn 03
Mission Control
What happened running your first mission, what it taught you about the business, and where your second mission is likely to come from. Homework: start it.
SESSION 04
Mission Accomplished?
By now you’re likely running two missions. This is where you learn the ongoing rhythm for reviewing them, and what comes next: Founder Circle, Advancing Skills, running missions on your own.
You don’t leave with a stack of documents to file away. You leave with two missions already doing something for your business, and the operating system underneath them: a CLAUDE.md that reflects how you actually run the company, and a specified agent or two doing real work inside it.
This is for founders using AI tools without a system governing them, wrestling with delegation, information flow, and decisions at scale. Not a course on which AI tools to use or how to prompt. If you haven’t run Bootstrap yet, that’s the prework, not a blocker: you do it before Week 1 starts.
What you’ll need
The setup is straightforward.
If you’re not already using Claude in some capacity, this workshop isn’t the right starting point.
Who’s in the room
Two facilitators, eleven peers, no audience.
Tim Barker
CEO and Co-Founder, Attain IP
Tim Barker has founded five startups and seen the startup journey from every angle. He sold his first company to Salesforce, spent five years in the formative age of cloud computing, taken companies public, and scaled them to several hundred people. Tim is a keen advocate for transparency, eating humble pie, and owning your mistakes. He is also a lifetime learner, which is part of why he felt compelled to ask: “What happens if you’re AI-native from day zero?”
Mark Littlewood
Founder, Business of Software
Mark has run Business of Software for 19 years, two annual conferences, more than 400 practitioner talks, and a community of founders building software companies that last. He has spent that time working out what actually separates the businesses that make it from those that don’t. This workshop is built on the same principle as every BoS event: helping entrepreneurs build better businesses alongside other smart people.
Registration open now
Build Your AI Company Operating System
$2,000 per participant
The BoS No Quibble Guarantee: if you attend and feel you didn’t get value, we will refund your fee. No questions asked. Questions about fit? Email Mark.Common questions
What’s included in the workshop fee?
Four two-hour sessions, one per week from 23 September. Pre-requisite: Bootstrap complete before Week 1.
What tools do I need before I start?
Claude Desktop, a Claude Pro or Team plan (required for Cowork mode), and to already be using Claude in some capacity in your business. Pre-requisite: Bootstrap complete before Week 1.
How is this different from an AI tools course?
This is not a tools course. It won’t teach you prompting basics or help you choose between platforms. It is about building the operating system underneath your tools, the documented rules, values, decision boundaries, and memory that allow anything you delegate to actually run without you holding it together. There are no paid speaker slots, no frameworks being sold, no sponsor content. The cohort is capped at 12 because peer quality and challenge are part of what you’re paying for, not a marketing tactic.