💌 A case study on a newsletter that writes itself
3 September 2026
buildwitholi
[AGENDA] In today's newsletter
- [UPDATE] One more session, then Zimbabwe
- [CASE STUDY] Three hours with a leadership coach and bootstrapped founder
- [RESOURCE] The meeting your AI books with you every morning
- [THE ECOSYSTEM] Book a call for when I'm back
[UPDATE] One more session, then Zimbabwe
Hey,
Last time I was writing from a new desk in Bristol, this time I'm writing with a bag half packed.
I've got one last coaching session tomorrow morning, and then I'm off to Zimbabwe for two weeks, a trip that's been in the works for months and that I'm really excited for.
Don't worry, the daily videos and emails will keep coming while I'm out there, and the photo at the top of the next one of these should be something pretty awesome.
[CASE STUDY] Three hours with a leadership coach and bootstrapped founder
A good few of you booked a call off the last email, thank you, so here's the first of the case studies I promised.
He runs a leadership coaching business, with an edtech business on the side, and the one word underlined twice in my notes from our first call was busy.
He was spread across five different AI tools, with none of them knowing anything about what the other four were up to.
What he wanted was a weekly newsletter to send to his mailing list, which he hadn't done in the past because he didn't have the time.
So we mapped out what he'd need to be able to do it in a time efficient way, while still authentically reflecting his views.
We settled on four main sections, with the data each one needs to draw on, skills to pull it all together, and one job that runs them all and leaves the draft ready to review.
At the end of the first session, he had the mental model and the first skill built and saved.
By the time it came to the second session, he'd started to piece together the other sections.
I have complete confidence that by next week, the weekly newsletter will start going out, set up in a sustainable, repeatable way.
And in his words, "I'm getting really excited about the possibility."
[RESOURCE] The meeting your AI books with you every morning
The piece of my own setup people ask about most is the fifteen-minute meeting Claude puts in my calendar every morning, and this is what's in it:
- Today's meetings and what I need before each one, read out of my own mail.
- The threads sitting on me, each with a reply already drafted and nothing sent.
- Whatever I wrote on the tablet yesterday, filed where it belongs.
- The numbers I wouldn't otherwise look at, for me the running watch, for you maybe the invoices nobody has paid.
I've written it up with the prompts that set it up, and the honest bit about what takes longer than it looks.
[THE ECOSYSTEM] Book a call for when I'm back
The thing I didn't expect from the calls so far is where the value has landed.
People come for the AI, and what they get is business coaching, a couple of hours thinking about what building and scaling actually means for them.
The ecosystem is then the system that makes it all real, on their own machine.
If that's a conversation you want to have, book in for a call, I'm back on the 19th so pick anything after that.
I'll have some more testimonials to share soon, and next week a case study on how a bakery in Colombia is now saving two days a month by using Claude.
Chat soon,
Oli