Dave Killeen: [00:00:00] Hi there. Welcome back to The Vibe PM episode eight. This one is the best one yet. I promise you. This is all about personal operating systems. Everyone's talking about it. I wanna make this one practical for you so you can get up and running with yours just in a handful of minutes after you watch all of this.

So I've been using Claude as a thinking partner for about eight months, and the system is just a bunch of text files on my computer notes, transcripts, projects to-dos, et cetera. And what Claude has been doing for me is basically helping me dance with that text in a way that really has been helping me be a lot more effective in my role here as Field CPO at Pendo.

But the more information I was adding into my system, the more unwieldy it becomes. And that's the challenge you typically have with personal knowledge management systems. It was reactive, I had to ask, but recently there has been a significant unlock with Claude, they're killing it at the moment, called hooks. Do not worry, this is not technical.

Hooks are a Claude code feature that basically triggers automations to happen on certain events, certain events that happen within a [00:01:00] chat that you're having with Claude. So now my system has changed fundamentally. Now my system is proactive. It silently captures learnings during my conversations with Claude. It checks Claude code's release notes daily without me having to do anything.

And it comes to me with suggestions saying, "Hey Dave, this new capability could improve your morning routine. Would you like me to implement it?" It observes how we work together. It improves itself. Every chat, it gets smarter than the last. There's a lot of great content out there right now showing people's Claude code setups, their personal AI chief of staff.

But what's been missing for me is something that you can actually use yourself quite quickly, something that's not technical. And today, I wanna fix that for you. I'm gonna be giving you a starter kit. You don't need to be technical. Like I say, you just clone a repo. I know I said you don't need to be technical.

But, it'll be very easy. I'll show you how to do this. And just after five minutes of onboarding that this repo has in place, you will be up and running and off to the races. The system will ask you your role. Are you a product manager? Are you chief marketing officer? [00:02:00] Are you a CEO? Do you work in customer success?

Whatever one you pick, of the 31 roles that are in there, the system will then unfurl its scaffolding, right for your role. And all that self-learning capability I've just described, all baked in for you. Let's get going. I'm really, really excited about this one.

SEGMENT 1

Dave Killeen: There's a concept called compound engineering from Dan Shipper at Every, and it's about coding with AI agents, and it took the web by storm over Christmas.

In traditional software, every feature makes the next one harder. More complexity, more maintenance. Shipper flipped this. Every feature makes the next one easier. How? By creating a learning loop. Bugs insights, better approaches all get documented and fed back into the agents. The code base gets more complex, but the AI's knowledge of it grows faster.

My luck was realizing this pattern isn't just for code, it could apply to my PKM system. And so here's what I've built. The AI has instructions to watch for learning opportunities during our conversations. A mistake is made, a preference is expressed a pattern in how I work, it captures these silently [00:03:00] in the background through Claude Hooks to markdown files, and so next sessions, those learnings get loaded in automatically.

So day one, the AI is generic. In day 30, it knows exactly how I operate. And it's not just memory. The whole system improves; it commands the automations, the workflows, all of it is compounding. And that's what this repo gives you.

SEGMENT 2

Dave Killeen: So four jobs, this system handles. We start each day focused. We have one command.

That daily plan command. It checks our calendar, opens tasks, what's overdue... it gives us three priorities, heavy meeting day, it automatically drops them to two. The system will not let us over commit.

Next up, we never miss a commitment. Promises made in meetings get extracted, automatically, fed into the right person, page, and company page so we can track what we owe and what's owed to us.

Three days old, everything gets flagged. Walk into every meeting prepared. Next up before any call, what we discussed the last time, open items, what they care about after the call, their page, again, updates automatically. And [00:04:00] MCP, this is where it shines. The tools feed into the AI. MCP connects existing tools such as our calendar, meeting transcripts from Granola, and for me there's also a Pendo MCP, so customer usage data flows in before the calls adoption dropping, I see it straight away.

Now with all of that outta the way, let's show you how to get all of this set up in tickety-boo fashion.

SEGMENT 3

Dave Killeen: Okay, so this is the Dex repo and what it has down here, essentially what a repo is on GitHub is essentially details on how the whole thing hangs together, with all the code down here as well.

And so what you would do is you go in here to the area, click on copy, and then you head on over to Cursor, which I'll show you in a second. And so when you get to this repo, by the way, down here, you'll see everything. Okay? So why we built this old repo, why I think it's important, what you get from it, how the system improves itself, the jobs that it does for you on all the different skills that you have and how to use them.

So be sure you go through all of this and it'll take you through how the whole thing hangs together. And then we'll get you up and running nicely for [00:05:00] when you start building out your PKM system. Cool. Cool, cool. Let's head on. Bring now to Cursor.

SEGMENT 4

Dave Killeen: Okay. So I'm gonna quickly show you how to get this set up in Cursor.

It's fairly self-explanatory from the Read Me file, but let me just quickly take you through visually how the whole thing works together. Okay? We're gonna clone the repo, we're gonna copy and paste, or we're gonna paste, I should say, the URL we tuck in from the repo page. And I'm gonna create a folder.

Then it's gonna pull everything down locally from that repo onto my machine and they're gonna open up that folder. And just to show you while it's pulled down, if you go to the cog at the top right hand corner, go to sidebar enable, you'll see everything that's been pulled down, right? So it's gonna have a Claude.md file.

The Claude.md file is the kind of brains of every time you go back and forth and talk to Claude, this file gets invoked and thrown into the context, right? So I'll come back to that in a second because we're gonna show you how this Claude.md file gets updated through the onboarding that we're about to go through and do.

So to start the onboarding, we're gonna go in and just try to set up, and now it's gonna kick off. So this is a command that we put into Claude for the [00:06:00] onboarding. And if you ever, by the way, want to have a look at any of the commands and understand how they all work, all you need to do is go into Claude and just ask it to say, look, can you just tell me how this whole thing works in simple terms?

And that gives you enough knowledge to then come up with ideas and how to improve it, and gives you some idea generally just on how commands are working so that you can then create other ones for your system. So when you first do this, it probably takes about 20 seconds for it to kind of kick into gear, and then you're off the races.

Okay? So it's asking me for my name. I'm gonna say, Dave,

It's not gonna ask me what's my role. So the system basically has a whole bunch of kind of templates for each of these roles that you see here, all 30 of them. Depending on which one you select, that context then would be fed in to the system. And then the Claude.md file will build out its own scaffolding by folder structure that's relevant to a role that you'll be choosing here.

So I'm gonna save number 22, I'm the CPO. And next up I'll ask you then is what kind of company are you working in? So I'm gonna say two, a [00:07:00] hundred to a thousand people. And then from there, it's now gonna ask me what projects do I have in fly right now? So I'm gonna say I want to launch a new mobile app and take that to market.

I want to then work with my exec team on the Series D fundraising, and I also want to come up with an AI fluency career letter for my organization. What you can see here is, yeah, even though, I obviously spoke too quickly and it says career letter, it knew exactly what I was looking to do. Here now is asking me if I've got additional context about me and what I do.

I can throw in my LinkedIn profile if I want to do that here. In the interest of time, I'll say just no. Again, the more context you give it about who you are and the projects you're working on, the better. Now it's asking if I'm using Granola for transcription because again, the onboarding is set up in a way and to look for the cache that Granola creates locally, and then connects that down to the Granola MCP that's baked into the system.

Now it's saying do I want to have the process meetings processed manually or automatic? I'm working on the assumption that [00:08:00] no one's going to have an API key, so we go manual. If you do manual, then Claude within Cursor, Opus 4.5 will then, as new content comes through when you run the command for process meetings that you see here, then it will use Opus 4.5 within your Cursor subscription to process everything. If you have an API key, then do automatic, it will then instruct you on how to pull the API key down and give it into the system. And then all of that then will happen automatically in the background for you. Whether you're doing manual or automatic.

All the right information will flow through to the relevant company page, person, page, and so on. All the tasks, all extracted, all there through then to work with. So I'm just gonna go for one in the interest of time.

Now it's updating everything. It's creating an updated Claude.md file. It's looking at what a CPO would typically do and creating the structure around all of that formula, in terms of my file structure. It's making all those different folders, and [00:09:00] that's it. When you see accept, just click on that and that's updating that Claude.md file that I showed you earlier.

And that's it. That easy.

So it's created my role, it's created additional role specific folders, and now if I want to get going, if Granola's connected, process the meetings, bring that context in, I might wanna say, okay, for my mobile app launch in active projects, let's go ahead and create it. Hey, can you walk me through setting up the active, uh, setting up the mobile launch for my active in my active projects folder?

And then it's gonna do that and guide me through all of that. And it's that easy. So just ask it to ask you for the context it needs for all your projects, all your work, and then any notes you have, just throw it in here. And you're all then up and running. It's that easy.

CLOSE

Dave Killeen: So here's what to do. Clone the repo, linked in the show notes, run through the onboarding that I just took you through, and then create some projects.

And then the day after, run the daily plan command first thing in your day. [00:10:00] By week two of daily practice, you'll be in full flow. You'll have all the skills to keep building. There's a great companion article that goes along with this episode. Again, link in the show notes. And that explains how everything hangs together from a first principal's point of view.

Here's what I believe. The people who figure this out, this personal knowledge management system. And the self-learning system will have a genuine edge, not incremental, transformational, getting more done with less stress, walking into every meeting prepared, having the AI as a thinking partner, having a system that gets smarter about how you work every single day.

Small impact and more joy in your work. This is the year of the personal operating system and is time now to build years. Many thanks for joining me on episode eight of The Vibe PM. Please spread the vibes and I'll see you next time. Take care.

Pendomonium

Dave Killeen: Registrations for Pendomonium 2026 are now open and you really don't wanna miss this one.

Folks, we're bringing together the most inspiring minds in product and leadership who will challenge your thinking on everything. I would like to personally offer you exclusive 30% [00:11:00] discount when you use the code, theVibePM30. That's the Vibe PM all lowercase one word. And the numbers three zero. Get your discounted ticket at pendo.io/pendomonium.

See you there.