A True Second Brain

0:00Our brain isn't a filing cabinet. It's very messy, it's very interconnected. The same search for multiple different people should actually yield different results because you think about the world differently. Imagine if there was just a digital colleague on every team who could sit on every single meeting, read every doc that was ever written, and had all of the context that was shared across the company. and knew exactly what information they could share with who and when they should share that information. You can delete 95 to 99 % of everything you have and never feel that pain for the rest of your life.

0:38Does it actually adapt to who you are? Does it learn about who you are and does it then apply that in future interactions? What do you like a human what? I think the running joke here is a clipy it was just ahead of its time. Since the rise of the computer, humans have been gripped by the idea of having a second brain. But has reality held up to that promise? How many people spend more time organizing their second brains instead of leveraging the information within them? How many people constantly look for a better -to -do app instead of actually checking the do's that they're organizing. And how many people have an endless stream of data that they'd love to one day process, but they just don't have the right tools or time to do so.

1:25Due to the structured directive nature of computers to date, computers have been a shell of maybe the second brain that we've long hoped for, still incredibly powerful, but also requiring discrete instruction from the director. But within the last year, Consumer AI has shown up to the party, now capable of processing simple language prompts and interfacing with unstructured data, possibly fundamentally changing this game. Today, together with the founders of Mem, Kevin Moody and Dennis Sue, plus writer Nat Alyson, we explore what's gotten in the way of a true second brain, and how AI might change game, finally unlocking what knowledge management tools have promised for so long.

2:09So, can our second brains finally work for us? Let's find out. As a reminder, the content here is for informational purposes only. Should not be taken as legal, business, tax, or investment advice, or be used to evaluate any investment or security, and is not directed at any investors or potential investors in any A16Z fund. Please note that A16Z and its affiliates may also maintain investments in the company's discussed in this podcast. For more details including a link to our investments, please see A16Z .com slash Discoachers.

2:45Let's start with that. Nat has worked on a ton of projects over the years, but primarily considers himself a writer. At one point you were writing a lot about productivity and knowledge management, and That's one of the reasons that we have you here. Tell me about why you got into that space. At some point, I just got interested in it. I think at one point, I adopted the belief as many do that the more I learned about productivity and the more knowledge I collected, the more financially successful or happy or whatever I would be, and ended up going very hard down that track because a lot of people do once they get that idea in their head.

3:27And something with the tools just clicked very well for me, where something about the way I was using it wasn't as immediately intuitive to people. And then in particular with Rome for those who remember that it was really like a mania, I think. It was. I just got very lucky that I was super early on it, was using it before a lot of other people. and I think it was one of the first people with a small to medium sized audience who talked about it. And then I think that helps people with much larger audiences pick it up. Tell me a little bit more about your saying you seem to have this intuition about how to use them.

4:04And then you shared that with other folks. What was it delivering for you and then subsequently others? That's a good question because I'm not sure that I could honestly say all of the effort has delivered a compensatory amount of value in the sense that even as a kid, I very much enjoyed finding interesting bits of knowledge and then sharing them with people are trying to explain them. And so almost like this kind of digital magpie, I enjoyed just collecting shiny bits of information to the extent that it's helped with writing. Most of it hasn't. The only thing that I could say definitely has really helped is a habit that I've had for 12 or 13, 14 years now of like taking notes from the books that I'm reading.

4:55And so I used to do this on Kindle, and now I do it on physical books and use read -wise to extract the highlights. But the medium that I organized those highlights in doesn't seem to matter because I had them in text files at one point I had them in Evernote, I had them in Notion, I had them in Rome, like I've moved to them around, I've lost a lot of the formatting and additional annotations so many times that it almost doesn't matter. You're almost saying it could be on a stone tablet and as long as you have that there, or is it maybe the searchability, there's only maybe a few functions that you need in order for it to be useful, not all of the features set.

5:29Yes, I think it's really researching the indexing and the collecting that are very helpful, but pretty much all of the other features often get in the way or become distractions or give you the sense of photo activity, right? Like, oh, I'm doing all of these, I'm organizing my knowledge and you probably should be writing or like playing with your kids or doing something else, right? But expanding on that, the thing that's really been helpful is the actual reading the books, right? Like, I wish I had spent more time reading more books instead of continuing to hyper -optimize my highlights from the books I had already read.

6:01Maybe there's something meta here though, to your point, it's like because you feel like you're being productive with the notes that you take within these knowledge management tools. It makes you want to read more books because you feel like they're more useful. But at the same time, it does seem like there is this false understanding of what you're getting from these tools. But one thing that I noticed was when you and a few other creators saw a room, like you said, there really was this almost like Mania. And maybe something behind that mania, at least it felt to me, was as though there was an unlock.

6:33As though the prior knowledge management tools were lacking something that this now provided. So maybe you could speak to that experience. Yeah, it's funny because this all happened at an interesting time where I had gone through Tiago Fortes building a second brain a couple of years before. And when I went through it, I was having these conversations with him about how much I hated ever note because it really forced you into this hierarchical way of organizing your information. And so you had a folder for home or whatever and then you're putting your notes about your house in there and you have a folder for books and you're putting all your book notes in there.

7:12Pretty much every piece of knowledge should live in multiple places. And you could also do tags and stuff but the tags felt clunky. And so what was exciting to me about Rome when I saw it was was introduced more of a knowledge graph. I think they might have invented that or popularized it for notetaking tools, right? Which is really, I think, how we think about things. Right, like that's more of how our brain works. Our brain isn't a filing cabinet. It's very messy, it's very interconnected. And it felt like it fit that much better for me. And that's what made me so excited about it. And I think made so many other people excited about it.

7:47We kind of take for granted, if you're getting into knowledge management today, almost every tool has this, right? that notion very quickly adopted the same interconnected back -length structure that Realm popularize. And I think that's great because I use it in notion all the time now. And that feature in particular was what felt so magical because to the point that we talked about earlier, where very few things in these tools are actually useful for improving the creative output, which I think what you're really optimizing for by using them. Search is very useful and the cap is very useful. Well, and I do think that these bi -directional relationships between bits of information are super useful as well, so that you can log a few connections on something, as long as it's connected to two or three other things in your second brain or whatever you wanna call it, it will be very easy to resurface it later, much easier than if you have to pick an arbitrary folder to put it into, at least for me.

8:44You have to remember the route, right? You're saying with ever note, you have to remember, Oh, there's this thing hidden in four layers of folders. And I have to remember it's there versus you're saying the interconnectivity allows you to surface it more easily, almost like stumble upon it, would you say? Or... Yeah, a little bit more like that. And the thing that I liked about it too was any hierarchical file system requires very deliberate placement of each piece of information. You have to think about it a lot where you put it. It might not seem like you do, but you kind of do because you're saying, okay, in 10 years, if I don't know any of this piece of information, how do I accidentally refine it?

9:20Whereas with a much more widespread, hyperlating, knowledge graph style, you can kind of just like slap 10 different relationships onto it, and you'll probably be able to find it again in the future. That's so interesting. I was filing something away, because I'm still in ancient times, I still use ever note, but I was filing something away, and I had this thought as I was doing so yesterday, I've just, I will never see this again. It was in that folder where I'm like, I haven't revisited this in years. And so why would I in the future? I had a few people reach out to me over the last week or two because Evernote's shutting down their US office and a lot of people are migrating ad revenue and they said, hey, I need to migrate all of my stuff into a new tool.

9:57What do you recommend? And I said, well, don't migrate anything. Just start using a new tool. And then for the next three months, see which pieces of information you end up needing. and then go migrate them. But what you will probably find is that you can delete 95 to 99 % of everything you have and never feel that pain for the rest of your life. It's so true. And in a way, it reflects on the fact that so many of us are digital hoarders, where if we did the same thing with physical items, we'd end up in these homes, just boxes and boxes and boxes. And in a way, because it costs so little and it is kind of out of sight, out of mind, we do it digitally.

10:41But that kind of brings me to this question. Do you think that maybe the way that these knowledge management tools haven't quite lived up to their promise? Is that just because we misunderstand the way our own brains work and what we really need? Or is it a facet of these tools not having the right technology, maybe the right feature set yet? I think it might be more of a false promise issue because I think if you look at say the notion marketing or the Evernote Marketing, they advertise themselves as a wiki, as a digital filing cabinet and they do those things very well, right? They allow you to collect and organize information.

11:27and I think the false promise that many of us believe or have gotten into or whatever is that if you organize information, you will write better articles, you will make more money, you will be happier, you will get all of these benefits from it, right? That one I think is probably just not true, right? Andy had this great tweet where he was like, you know, for all of the influencers talking about personal knowledge management and note taking in those things, remarkably few of them have written a great book or one in the ME or an Oscar or like actually done anything that incredible with their knowledge management systems.

12:11The main use case seems to be talking about your knowledge management system. And I think that he was kind of like brutally honest.

12:23They're very seen right? I've seen other tweets similar where you're like, yeah, if you want to learn from the best founders, they're busy building companies, right? Not writing lead threads. Yeah, and there are obviously exceptions and things, but I make this analogy all the time that 99 .9 % of the best books ever written were written on a typewriter by hand. Like if you think that you need a good writing app to write your book, you're just wrong. It's just not true. History has shown us, this is not true. Exactly. So I do think that there is this big element of the other thing that delivering is fun, right?

12:58And we don't like to admit that the reason we Reproductivity books or watch motivational YouTube's or stuff is because it's fun and makes us feel good And that's part of what they're delivering to like it's fun to organize your stuff, right? And I had this really funny experience Because our older daughters almost to now and one of her favorite hobbies is to just organize random things like opening the pantry and like pulling stuff out and like moving it from one container to the other or taking all the mixing bowls and like sacking them in the correct sizes. And I'm watching her do this and I go, oh, like this is just hardwired in me.

13:32Like there's just part of my brain that likes moving things around and putting them in a satisfying order. And like that's what I'm getting out of these tools. That is so good, because we've all been there, right? Like, oh yeah. I mean, the most meta thing, right? You have in your ever -note or in your notion, organize ever -note. And it's just like this is like so circular. or everybody's had the experience of, maybe not everybody's had this experience. We're people like me who've had this experience, of getting a bunch of things done, and then looking in your task manager and being annoyed that you didn't put those things in there first.

14:00Oh yeah, and then you add them. Then you add them and then check them off. So you can feel good about yourself for the day. I know and you somehow convinced yourself that you did the right thing. Instead of following the things you had outlined, it's more important. You did unimportant other things, but it still must be checked off. No, totally. So I think you're right. I think there is this level of just humans wanting to feel productive and these tools can sometimes validate that. And sometimes I do think that they can help us. I mean, if I truly had to remember off the top of my head all of the, quote unquote, important things that I had to do, I just couldn't.

14:33So there is a level of utility here. Totally. I mean, the number of times I had this experience of writing an article and then I think like, I feel like I've seen this or I've felt this idea somewhere before. And then I look over at my bookshelf and one or two books pop out that remind me of what I'm talking about and then I go into my note taking tool and surface my highlights from those books. And then I like immediately have a quotation that I might have saved 10 years ago from a book that I can use in the piece that I can reference. Like that's so useful. Right. Right. So the useful things were reading the book and capturing the highlights and then being able to search for it and it kind of like stops there.

15:08Right. And it's being able to get the information you want at the right time and not having to do as much digging. And so with that in mind, And if we think about things along this spectrum of actual utility that these tools are indeed bringing, and then this false promise, tell me a little bit more about how you've maybe moved closer to that utility side of the spectrum. I really think the next big utility is going to be a note -taking tool that offers custom GPT or whatever embeds as a service for your knowledge graph. because I've seen people do it. Dan Shipper has that great project he did where he put all of Andrew Huberman's podcast transcripts into a GPT -Embed model.

15:51And then you can just query it with anything you want to know. And it feeds you back Huberman's answers from podcasts. Right. Theoretically any note -taking app should be able to offer that. I'd pay like a thousand dollars or more for this. Very happily. Where I could just say, okay, here are my notes from like four or 500 books now, thousands of articles, every little idea I've written down over the last 10, 15 years, here's all of it. I just want you to index it and then as I start writing, just give me a little pop -ups along the side. Or what I asked for them to give me a little pop -ups to say, oh, you had this idea, oh, this idea from this book, or this idea from this article, or whatever, like these are all relevant to what you're doing right now.

16:31Because I'm pretty sure we can actually already do that with the tools that are available on the market. Yeah, nobody's just created a consumer side version of it. That's like literally a second brain. That's literally your previous thoughts and work and effort being processed by this external cognitive entity and then fed back to your current working mind or whatever to enhance what you're trying to do without you having to go look for it. And that would be incredible. Like that would be so useful. I would use that non -stop every day. And if we just break down what the difference is there, it feels like maybe something you're pointing at is the proactivity.

17:08You are having, as you're saying, a second brain support you in a way where you don't have to go and say, hey, I need this. Let me go search for this. It's popping up and saying, hey, I've actually gone through all of this unstructured data that you've compiled over years and years. Yeah, I would say it turns your note -taking tool from a means to surface known unknowns. So, you know, right now I can say, I know that I know this thing, but I don't remember it exactly. I know that I have notes from what your food ate, but I don't remember what this note was. I will go find it. It does that very well, but with this it could provide you with your unknown unknowns.

17:48It's making connections that you haven't thought of yet. Exactly. Exactly. It can look at every single sentence of what you're doing and say, oh, you actually wrote an article about this six years ago. Like I forget about articles I've written all the time, right? Like somebody will say, oh, I really love that article or they'll send me links and be like, oh my god, I wrote that. Or have you ever had that experience where you go reread it and you're like, did I write this? Yeah, yeah, super weird. Totally. They're impressed or maybe like annoyed sometimes where this is feeling of, oh, I already wrote this article three years ago and I kind of like forgot and now I'm rewriting the same article.

18:20And that would just be so powerful because you don't have to try to remember the surface level of everything you've stored. like it's handling that for you and just feeding you back things that are yours. Because there's definitely going to be this phase, I think at least for a while, of AI helping to enhance high -performing creators. Right? Like, if you look at GPT -4's writing, it's better than 90 % of people, probably 95 or 98 % of people, but it's like way worse than the good writers. In the top 100%. Yeah. Yeah. And it's actually pretty hard to get a ton of value out of it for the parts of writing that you're good at.

18:57But if it can actually surface stuff for you to use, right? Like if it can handle some of that search for you and whatnot so that you can produce a lot more, produce faster, right? Like that starts to get pretty interesting. Yeah. You can imagine how the unstructured nature of AI can actually maybe surface some of these more interesting connections where it's, again, you're talking about one concept, but But it's like, hey, this isn't directly related, but there's a similar arc, there's a similar learning. Yeah, my dream tool would just be a blank page where as you start writing words get underlined or sentences get underlined and like very subtly.

19:35So it's not going to interrupt your flow, but it's there as a little note. And then whenever you want to take a break, you can go back and hover over it and it'll pop up and show you, you know, the stuff that you've written about or done or said in the past might be related to what you're talking about right there. Then you can start through it at your leisure and all that's just being done on the fly as you write without you having to interrupt yourself without being interrupted. Right. What's really interesting about that is we've obviously seen how different AI tools have been used for code.

20:03When I think of many of the UI's that have been designed for code, they originally started with this idea of like, oh, it's just going to write the code for you. and similarly, they came to the understanding that actually developers still want to code, but they just want suggestions, especially when those suggestions are likely to help them. And so you can kind of design the tool to say, oh, I'm pretty sure if it's like a 95 -plus -percent chance this is related, I'm going to showcase it. People even have their own dials to say, I want it to be as broad or as precise, depending on what kind of article I'm writing.

20:36And what's really magical about that is the more you write or have written or the more you do, the more useful the tool becomes and the more powerful you become. JTPT is a very, really, any of these is a very democratic tool right now in the sense that everyone has access to the same quality of recommendations. But if you have your own private custom model that's been trained on everything you've ever done and your style of writing, and really you writing at your best, because I think I think everybody who writes this had this experience of, they sit down and they're just on fire and they bang out an article in 30 or 60 minutes and at the end of it, they're like, whoa, like, that was sick, right?

21:16Like, who wrote that almost? In your sad when you don't get that feeling because you know it can be better, you can be really on it, but you can't have it all the time, right? You could theoretically train it on your best work and then have it help you configure anything you're writing to emulate you at your best. And that's pretty magical thought too. So, but I love that idea of it helping you become the TEDx better version of yourself as opposed to what it does now where it basically just like raises the floor for everyone. Right. Yeah. I mean, as we discussed, like maybe a true second brain.

21:49So on that note, final thing is just if you imagine a tool like this where an AI can parse your personalized unstructured data, it can be proactive and it can surface things as you need them, what do you think this unlocks? There's this interesting element of world that we're getting into of the valuable thing is the ideas But everybody receives ideas in different ways for example like one thing I realized about myself at some point is that I have a very hard time processing auditory information Like I don't remember it. It just doesn't really imprint for me But when I read things they stick with me really well And so if I read a book I can remember a ton from it but if I listen to an audio book, I don't remember anything.

22:33And some people prefer the like spunkier punchy, Twitter thread style. Some people prefer the long form essay style. Like some people would prefer a short form video of the idea. Right. And so if you have an idea and you can turn it into one of those forms, something that's trained on you should be able to help you produce those other forms of your work to help that idea reach that most people possibly. Right. And we're seeing something else in tandem with the potential for that, which is like platforms aren't really letting you use them as funnels anymore. Early internet marketing with social media 10 years ago or whatever.

23:12Like your Facebook and your Twitter and whatever, we're all to drive traffic back to your site, right? Where you could get email science or sales or whatnot. And it's way harder to do that now. Like it's really harder. It's way harder. It's really punished. It's really punished. Yeah, yeah, they punish it. They don't want you to do it. And so you actually want to create native stuff for each of those platforms for the people who want to spend time on those platforms, because that's what's going to get rewarded. But now you're like not creating one article, you're trying to create like 10 assets off of each idea, which is a huge time stock.

23:42And so it's interesting to think too, like what would it look like if you had this kind of like content assistant who you train not only on all of your writing and stuff, but on your preferred format for short and long form videos. and train on your voice so that you can immediately create like a podcast from your articles and all these things so that you can be this like hyper -distributed idea person. That world is not very far away. It's probably like less than two or three years out. I think what you said that's interesting there. It's in your unique way. Because you can hire agencies, you can bring on other folks and many people do that already.

24:16But I think maybe the nugget there is if you were able to take one nugget and repurpose it in your unique style over and over, that does seem special and that does seem like you can't quite do that today. Yeah, you made a really good point there about agencies, right, because I've been reached out to by a number of like short -form video agencies where they say, oh, you look at your TikToks and we think they could be better. Here's an example of how we improved it and I looked at it and I'm like, I've seen 10 other people on TikTok with this exact same style of editing. You have templates that you can just copy and paste for everyone and it probably works to some extent but then people start to note it, they start to see the edges of it.