SF

Scott Farrar

Things Scott Says on Podcasts

Where to Find Them

Scott Farrar has been a guest on Lenny's Newsletter and How I AI .

Recently: “Claude Code + Obsidian: My family’s AI brain | Scott Farrar” on Lenny's Newsletter (November 2026); “Claude Code + Obsidian: My family’s AI brain | Scott Farrar” on How I AI (November 2026).

What They Said

Claire Vo asked whether his Claude Code and Obsidian household brain actually changes his behavior. Scott says that because tasks and next steps live in markdown files, Claude keeps nudging him, and he has cleared his own backlog of household projects.

How I AI · 2026-11-11 Permalink → Listen →
How I AI Around 18:19 into the episode
Scott Farrar

…And then maybe some longer term stuff that's like needs attention and just some stuff for my kids. I also made a section of recent wins just to say like, good job. You did fix that or you found out what iPads were out of date with software. You fixed the water heater in one day. Great job, Dad.

Claire Vo

…on and we would like move it on this physical board. And then we had like a wall of wins. And I like that you were bringing that very wonderful scrub master energy to your household, household management. Do you find that this like helps you get stuff done? Does it actually change your behavior?

Scott Farrar

It does. It does because when it has built a checklist for me, like on the insurance, all these next steps or open items, they are not like lost in my memory of like, oh, I should do that, just like a should thought in my head. It's recorded somewhere and it's like, well, come back every time I do something in any chat, it might remind me of like, hey, actually, you're overdue on something. Like it's going to remind me that you've been waiting since September 24th on this. And so it's really actually has moved me forward on so many projects that I've actually kind of like run out of pending fires. And I was like, oh, that's a new experience. I used to have a backlog and now I'm, now I actually, it's the balls on everyone else's court. Like I'm always sending the email and it's, I'm waiting on them. And that's been really nice.

Claire Vo

So give me, just give me the list of, you know, if somebody's like lives in their house as an adult, give me a list of like, here are household tasks you should just get your AI to think about. So I saw repairs. I saw like comparison shopping. What else? What's on, what's on the list so people can…

Scott Farrar

So here's the, here's what's in this to-do list. There's repairs. There's a little bit of like, yeah, insurance, financial, maybe like future planning, wills, guardianship, trusts, retirement funds. Like if you want to consolidate your retirement, actually, that's a huge headache that I've been…

Claire Vo

I really love this. And what I'm seeing here, it looks like this is invoking a skill or a plug-in to just follow your little process.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“Instead of a chatbot tutor aiming to teach the student, the chatbot aims to extract some teachings from the student. The chatbot might say, help me understand how to solve a linear equation. And the student says, well, maybe subtract things from both sides. And the chatbot's like, ah, but why do you have to do that? Students have a lot of great knowledge in their heads, but sometimes they're afraid to share it with humans and with AI.” — Scott Farrar, Lenny's Newsletter

Claire asked for an example of keeping student agency in AI-assisted math learning. Farrar, a math teacher, proposes flipping the tutor relationship so the student does the explaining.

Lenny's Newsletter · 2026-11-11 Permalink → Listen →
Lenny's Newsletter
Scott Farrar

…the answer or is too helpful or kind of maybe even doesn't appreciate the ideas that the student is giving. So I'm really, I really like some of the products I see out there that are interpreting what the students say and running with that. It's like, oh, good idea, kid. Tell me more about that.

Claire Vo

…And from a AI education perspective, you like, you know, solutions where it can support interpretation of what a student is doing, but not take away that agency of like, I am learning how to solve this problem. I am learning how to, how to do the work. Can you show me an example of what you mean?

Scott Farrar

Yeah, I think like I've seen some projects. I've kind of noodled on projects myself where you kind of flip the relationship of a chatbot tutor where the tutor is now that the chatbot is not aiming to teach the student, but the chatbot is aiming to extract some teachings from the student. And so the chatbot might say, help me understand how to solve a linear equation. And the student might say like, oh, well, I kind of know what you should do is maybe subtract things from both sides. And the chatbot's like, ah, but why do you have to do that? And, you know, can the chatbot be positioned so that they are not annoying, but they can still grab the ideas that the student has. And the students have a lot of great knowledge in their heads, but sometimes they're afraid to share it out with humans and share it out with AI. So I think it's going to be powerful if we can enable kids to share their thoughts.

Claire Vo

Today is, this is my second episode I've recorded today. And the earlier one was also about a language tutoring episode. So it might already be live. But what we were talking about in that one is AI is this like infinitely patient private tutor you can say all your dumbest stuff to. And so it's…

Scott Farrar

Yeah, I think actually the zone of frustration or zone of proximal development, I think, like, you know, can the tutor, I like you also mentioned infinite patience. And I think that's something that is interesting to play with in the chatbot realm of like, should it be infinitely patient or should…

Claire Vo

I need to give you some. You can do it. Why don't you give it a try? Yeah,

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“I wanted to build a system where I was confident that AI was grounded in my truth and knowing what it knows about me, so that I could be confident in the advice it was giving me back. So instead of the chat interface, I switched over to a coding agent. In Claude Code, I built this system that would read and write Markdown files, so they would have the memory of what we were talking about, and it would live on my computer.” — Scott Farrar, Lenny's Newsletter

Claire Vo asked what problem he was solving with his household setup. Farrar explains his unease with chat tools, never knowing what the model remembers about him, and why he moved his family's information into plain files a coding agent can read and write.

Lenny's Newsletter · 2026-11-11 Permalink → Listen →
Lenny's Newsletter
Scott Farrar

Busy, busy adulting.

Claire Vo

…Everybody always asks, like, we need more parents on. We need more people handling their busy lives. And so when I saw some of the stuff that you were doing, I was so excited for you to demo it for us. So walk us through what your busy adulting looks like and what problem you were trying to solve.

Scott Farrar

I have kids. I've got a career and it's like hard to juggle everything. And if I come up with a question like, oh, should I, do I have the right car insurance? Do I need to change that? You know, lots of like lots of people, I might come to AI. I might go to the chat and have it help me out. But the problem I was having there is if I start doing a complex problem with chat, it's like, well, do I dump my information in there? Do I give it all the context into this chat here? And as the conversation goes, is it drifting? What is it really remembering about me? So I wanted to build a system where I was confident that AI was grounded in my truth and knowing what it knows about me so that I could be confident in what advice it was giving me back. So what I did, instead of just going with the chat interface, switching over to a coding agent. So in Claude Code, I built this system that would read and write files, read and write markdown files. So they would have the memory of what we were talking about. And it would be living on my computer so that if I come back later and start a new chat session, a cloud code session, it can reference those same files. So if I, here's kind of a sample of the car insurance…

Claire Vo

So, the problem that you're trying to solve here really is when you're using like the web, you know, Chat GPT or Claude, you're like, what does it really know about me? What does it really remember? What information does it have? Like, that is very opaque to most people. But once you download these…

Scott Farrar

What I started with was just saying, well, should I should I update this? And in the conversation or an updating another insurance, it says, well, one of these people giving you a quote said, you need to update the cars. And if you also wanted this other policy, and in the previous years, I might…

Claire Vo

And I mean, how would you have done this before? Because I'll tell you exactly how I would have done it before. I wouldn't have done it.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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