Gaby Goldberg on Magic Internet Money, Living on the Internet, and How to Get Good at Twitter

Hey everybody, welcome back to another episode of Infinite Money Glitch. I'm Zach. I'm here with my co-host Martin and our very, very special guest Gabby Goldberg. Gabby, welcome to the show.

So excited to be here. Can't wait. Thank you so much for having me.

We are so, so hyped that you're here. Um, we're gonna start our show just like we start every other conversation. What is your earliest memory of the internet and how has that evolved over time?

It'll take me a minute to really think of the first memory, but I can kind of paint a scene of early memories, plural. So I grew up in Farmington, Connecticut, and both of my parents were and are doctors. So my dad works in the emergency room and then my mom is a gynecologist, but At the time she was an OB-GYN. And so I actually didn't see a lot of my parents growing up. We had an au pair live in our house and a lot of my early memories of the internet are in the computer room in our house in Farmington. And it was like one of these big computers, obviously, and it was my dad's office. And my older brother and I would spend a lot of time exploring the internet in different ways. And so. I would say probably the 3 most popular places we spent time kind of staggered across different time periods were Minecraft and RuneScape and Webkinz. And Webkinz was probably the first one. And so I distinctly remember the day that I got my first Webkinz. I remember waking up and going downstairs and there was a white poodle on the kitchen table and then getting to play. And the funny story around Webkinz is My brothers and I, I have an older brother and a younger brother, we would all play and I was really good at it. Like I was really good at playing the mini games and I had a really nice house. And basically my little brother was like homeless in Webkinz. Like all of his animals were like super dirty and hungry and they would spend time in my place and like I would make him smoothies with my blender and stuff.

Mm-hmm.

And then what I only came to find out later in life, like in the last couple years, is my mom who would work literally all day and all night delivering babies in the OR, would come home and log onto my little brother's account and play all of the minigames and go to the Curio Shop and like do these things to have his little animals survive, which I think is so cute.

Really?

And just the dedication to the craft. And so that's one of my early memories. And then growing up, I spent a lot of time on Minecraft and a lot of time on RuneScape with my brothers. Um, but I, I think probably those Webkinz memories were the earliest ones.

What do you think, like, what do you think has changed about your feelings about the internet or technology more broadly? Like going from, you know, Webkinz days to RuneScape to now, obviously you have a big kind of Twitter personality. What do you think has changed about your relationship to the internet?

Yeah, actually this morning I'll need to pull up the name of it. And then if you guys have like a show notes or something, we can put the report in the show notes. Cause I don't remember off the top of my head, but Earlier today, someone on my team sent this consumer report of the past year to, uh, my broader team. And one of the pages that he called out is that, you know, from this, from this survey, half of Gen Z wants to spend more time online and half of Gen Z wants to spend less time online. And I do feel like I'm, I'm curious where you guys fall on that spectrum. I'm not totally sure. I, I guess actually, yeah, I wanna hear from you first and then I have thoughts on it.

What is, what does it mean by more time online? Like, is it more specific than that? Was there like a breakdown of like, cuz I think being online can be so many different things.

Yeah. Let's see if I can pull it up.

Uh, if you, yeah, if you can find it. But I think for me it would be like, I, I don't think I would ever think, oh, I want to be online more. I think it would just be like, cuz I think the amount of time that I spend online is too much. So it's just a matter of like, Rewiring it into more productive things. But I, I think there's like apps I wanna use less, but I don't think of my time as like more or less time online. It's like less time on my phone. The only thing is, yeah, potentially the only situation where I think I wanna spend more time online is like playing games online with my friends or like calling my grandparents or stuff like that. Um, but I wouldn't say like just blanket statement, I wanna spend more time online. I wouldn't, I would never even think to say that.

That's interesting. I think like I resonate with one of the things you're saying, Martin, which is you want to be more intentional about how you spend your time online.

Exactly.

That's kind of how I feel too. Like, well, we'll get into this a little bit later in the conversation. But Gabby and I both have our phones set to grayscale mode now. And so it just like absolutely is not the dopamine suck that it normally is.

Yeah.

And that has definitely made me more intentional about when and how I use my phone and I actually did the same with my iPad. And so like same thing with my iPad too. I've also found to be like, I found myself to be more productive on days that I spend less time on a screen and only go to that screen with an important and intentional and, you know, current and present need to go to that screen rather than just like default to sitting on the screen and then getting distracted by a bunch of different things online. But Yeah. Gabby, what about you? How do you, uh, how do you think about that?

Yeah, so I'm looking at this, this graph now. I realized I had to stop sharing cuz I probably shouldn't be sharing my email screen on this, so I took it down. But so they, they survey Gen Z, millennials, Gen X, and boomers. Gen X and boomers are both over 30% wanna spend less time online, and then less than 20% for Gen X and 7% for boomers wanna spend more time. And I imagine that's like, I want to be more connected to be able to like see what my grandkids are doing or something like that. And then kids or grandkids, and then millennials and Gen Z are both pretty much an exactly even split. And the question is just, do you wish you spent more or less time online? So maybe for more, it's people who have goals of, of making money online, like being creators or things like that and wanting to spend more time online in that sense. And I don't know, I love being connected. I, I've talked a lot about how TikTok is my favorite social app for a lot of reasons. Maybe it's not even a social app, but, but like an entertainment, like piece of media. But yeah, Zach, as I was talking to you about this week, I, the best way I can describe it is I feel like my addiction to and reliance on technology has gotten to a point Over the last couple months, and I'm not really sure why it's happening now, but it got to a point where I basically felt like I was like unconscious for a minute. Like I was operating in such a rote state.

Yeah.

And I wasn't moving forward and I wasn't being as creative as I normally am, and I wasn't outputting or creating as much like energy into the world as I felt like I was before. And I've had an immediate switch this week from deleting a lot of my apps and turning my phone on grayscale to the point that I feel like this week was one of my most productive weeks in the last multiple months. And it was only 4 days and it happened immediately. So I don't even know what to make of any of that.

I, yeah, I totally resonate with that a lot. And it's, it's funny, it, it brings up a a tweet or like a Facebook post that my mom shared with me from one of my favorite just philosophical thinkers, this guy Rabbi Wolpe, who I know Gabby and I both share, you know, a love of his work. And he posted somewhere, my mom just sent me the screenshot. It says, you know, in Kabbalah's tradition of, or in a Kabbalist account of creation, God created halal panui, an empty space into which creation could flow. In a life crowded by email and social media and streaming shows, If you wish to be creative, do the same. Create an empty space so creation can find its way in. And so I think like that's what we're getting at, Gabby, which is this, you know, when you remove the color and all of the notifications from your phone, you turn it to grayscale and you're more intentional with your time. You're essentially creating this like emptiness in this vacuum that that phone or that piece of technology kind of filled as a void. And that void is where all of that new creative you know, force comes from. And I've felt the same with you where, you know, using my phone and using technology less, I actually feel more creative as a result. And so then when you go back to that thing, you now have like a purpose and a reason for why you're using that piece of technology rather than just kind of defaulting into the, you know, I guess robotic mode that you described. So I know that like, obviously, in order to get to where you are today career-wise, I mean, you obviously spent a lot of time online. And I think, Gabby, your journey is a little bit different than most. And full of interesting insights for younger people early in their careers. Tell us the story of like how you got here today from, you know, from the Stanford days to Chapter One to now TCG and what role did like the internet play in that? And more broadly, like talk about kind of your Twitter presence and writing and all that good stuff.

Big reason I spent so much time online and continue to spend so much time online is actually from my childhood. So like the Webkinz things, we'll go back to that time period. I actually grew up selectively mute for 5 years. Which is still something that I am trying to make sense of in my life. I think as a result of that experience, a lot of my memory is actually very cloudy from those years. And so there's a lot that I actually don't know. So most of the time that I was selectively mute, I don't remember it. Like, I don't remember the names of my teachers or like even like friends I had during that time period. And I was pretty young. I was like under the age of 10 for the whole thing. But because of that. I spent a lot of time online, and even as I got older, I spent a lot of time by myself and reading and writing and, and those types of hobbies were what I did from an early age. And so growing up, finding community online always felt normal to me. And so even now, some of my friends don't understand what I mean when I say I'm hanging out with Like internet friends, like actually both of you guys, right? Like I met both of you guys through the internet. And so it's, I still don't even know what to call you. I guess with you guys I do, but like for a lot of my friends, for example, who I've never met in person, it's like, what do you call those types of relationships and how do you explain it to people who don't totally get it? Side note, something there that I think is really interesting is this transition from physical relationships to or digital relationships to physical, the only place where it's really not that taboo is in dating. So I have a lot of friends and family members and just like a lot of people in my life who met people that they're dating or are now married to through something like Tinder or Hinge or something like that. And that's actually not weird. Like if I were to tell my parents that I met someone on a dating app, they wouldn't think that it's weird. But if I were to tell basically anybody that I met someone on Bumble BFF, like that is still weird.

Yeah.

And it's still really taboo. And I just think that that is interesting. So that's a side note. But I grew up playing a lot of Webkinz, and Webkinz is a bad example 'cause it's not as social, but like RuneScape, I made real friends on Minecraft. Actually, I made a friend where when I went to Stanford and he went to Berkeley, you know, multiple years later we met at the big game and like that was a crazy experience for me. It was my first time meeting a digital friend in real life. But basically I've always been really comfortable on the internet. So then I, uh, went to Stanford. I initially came in as a philosophy major because I wanted to go to law school and started taking computer science classes for no real reason. Um, I just enjoyed it and it was a challenge and I ended up studying human-computer interaction. And so a lot of the classes that I took revolved around social computing and I worked in the virtual reality lab. There's this amazing Book called, well, I know the class is called Virtual People. Let me make sure what the book is called again, by Jaron Lanier. It might be called Dawn of the New Everything.

Cool.

I'll put that in the show notes also. Great. Yep.

We'll add it in.

Great book. And that was a lot of the stuff that I was really interested in, but not connected to career at all. I really had no idea. What it was like to be a working member of society. And I really struggled with finding what I wanted to do because when you go to a school like Stanford, and I think a lot of people at a lot of schools have experiences like this, you think that the hard work is over once you get there, but actually it becomes way more competitive once you're there than even to go. And so I wasn't really involved in any pre-professional clubs or organizations, and I had no insight into Like how to get a job. Anyway, all that being said, I took a year off my junior year to try and figure all of that stuff out. And I went to Israel because I wanted to become more fluent in Hebrew. And I, obviously they have a really vibrant tech scene in Tel Aviv, and I was working at an HR startup there. I was the only woman and I was the only native English speaker on their product and tech team on the first floor. So like, it was very interesting. The second floor. Was all English speakers and all women who had moved from the States to Tel Aviv cuz they wanted to like live out the same dream that I had. But they were all doing, they were all doing like sales and comms and content and stuff like that. And then the first floor was all dudes straight from the army who all knew each other. And then it was me.

Yeah.

And it was a very interesting like social experiment. And I actually, I had a lot of fun. And it was great. And that coincided with COVID So basically, probably 2 weeks before COVID actually happened, I met an investor who was an American living in Tel Aviv. And he kind of saw the stuff I was doing. I was like going to networking events. I had just started putting my writing online. And he basically told me that he, that I might really like the work that he does. And that a lot of the things that I like to do for fun, you, you basically get paid to do if you work in venture. And I still had no idea what I wanted to do with my life. And so I thought that that was a pretty good idea. And I got on Twitter per his advice, and I just followed a lot of people in tech and venture, and I started getting a very high-level sense of what those people do on a daily basis and the types of people that they're friends with and what they read and they write. And it is a really helpful way to get started. So again, 2 weeks later, COVID hits. Israel's one of the first countries to basically kick everyone out unless you're staying. And so I left and it was on my flight home, or like more specifically, I was sitting in the SFO airport lounge when I saw this tweet from JMJ who had founded a micro fund called Chapter One, investing in consumer products. He tweeted out that he was hiring an intern. And so I was very much at the right place at the right time for a lot of reasons. I was physically at the place where I could see that the tweet was up and I sent him an email before he got to any applications, but From like a very high level, I was in the right place too by being, you know, fresh out of college or like, you know, ready to take a job because of COVID I had just lost this other job and I knew that I wanted to work in venture. There was a massive bull run, like even, even outside of crypto, obviously. And it was the rise of this so-called solo GP. And so funds like Chapter One were doing really, really well. And this idea of, you know, investors as almost like influencers in their own right and being able to build really powerful networks was a new narrative. And so it was a really cool place to be at that time, and I got very lucky by having that opportunity.

For sure.

And so that is how I got started. I worked with Jeff for like 7 months. Had so much fun. And then I moved over to a larger fund called Bessemer, which has been around for a really long time. They've invested in companies like Pinterest and Twilio and Shopify and things like that. And the advice that I got to join Bessemer was like, it seems like you like investing, but if you wanna really learn how to invest, you should go to a place like Bessemer. And I think that was very good advice. About a year in, I realized that there were, I, I had kind of narrowed down what I wanted to do and where I wanted to spend time. And it was 3 main things. It was early stage, It was consumer and it was Web3, and I wanted to go to a place that was really built around those 3 principles as well, which is how I got to TCG. And then the writing and the Twitter and everything happened along the way, and that was how that all happened. So I don't think I would've gotten any of those jobs had I not been writing and putting my thoughts out online and networking with people during a time where nobody was hanging out in person. Twitter was really valuable for that.

I feel like you kind of undersold how—

I was going to say that too.

I don't want to use the word meteoric, but when I was thinking about this, I was thinking about like meteoric rise. I feel like, because I think there was this period where you said, so you basically made your Twitter account in like early 2020, right? That's when I kind of started getting on tech Twitter too. And you have like 75,000 followers. And I have 2,000. So clearly you were doing something a little bit differently. I'm kind of curious how you would explain what you did at that time. Like, was it a very intentional of like, hey, like if I basically just write these articles on these things I'm learning about and tweet about them, it clearly does very well. Or was it just kind of this much more organic thing where you were just doing what felt natural and it happened that like At that time, like writing threads about, like most of my followers for me came from one time I wrote one post and one Twitter thread and I got like 200 followers.

Yeah, it was a banger.

It was, it was, it was average.

Well, I, I think that, I think that's how we connected. I'm pretty sure I DM'd you from that post.

Yeah, I think so.

So there you go.

Yeah.

I don't wanna say, I don't, I don't wanna say it wasn't organic because I like to write and writing helps me understand what I think about certain things. And so I, I try and force myself to write so I can understand how I feel about different topics. But I definitely had the sauce. Like I understood, I understood Twitter was a tool and I saw it's sort of like great online game type of vibes of like, yep. And I, I tell this to like, well, I don't know if I'm gonna say that, but You see a lot of people playing the game and you can either, you can either disregard it, which is great and fine. I have a, I have a lot of friends who are really successful in what they do and also just great people and that I love to hang out with and they're not online at all. But you can't, you can't be mad at the game, right? It's you either—

Yeah.

You either play and you figure out how to, what the rules are. Or you just don't, and then you just don't care about it, but you can't really be in the middle. So I found that it was a really quick way to get to where I wanted to go by building a personal brand. And that happened to be online because the world was online. And so specifically, if there are young people who are trying to find the sauce, I can't really help anymore cuz my engagement is awful. Like I, I just tweeted something right before.

Gabby got shadow banned.

No, I lit— I honestly might've. Well, I think my content's just not as good, but 41 minutes ago, literally 41 minutes ago, I had this great tweet, banger tweet, 8 likes, and I have 75,000 followers. So I can't help anymore. But what I did before is I would write something and I would write about various things in consumer tech. And so the first piece that I wrote that did pretty well is I wrote about basically like this hype and influencer strategy. And honestly, it's aged pretty poorly. Like if you read some of the companies that I'm talking about in there, like Well, but, but to be fair, the methods that they used for gaining hype and raising capital did work. So that's that. Yeah.

Yeah.

And what I would do is I would write about a bunch of companies and have a sort of thesis or framework. And then before I published the piece, I would put a draft in Google Docs that was view only, and I would DM every investor in those companies.

Yeah.

I would DM the founders and influential people at those companies, and I would say, hey, like, Pretty much, you know, like I'm a young person trying to break in. I'd say, hey, I just wrote this piece. I'd love your thoughts on it. Then the next day I would post it and I would tag all of those people in the tweet saying, thanks so much for your feedback and thanks so much for, you know, influencing my thoughts. And then they would retweet it and that was the sauce. And so that's what I did and it worked very well.

It's pretty killer. I would say like, I mean, I know Gabby, we've talked about this a lot, probably privately. I don't know if you've ever talked about that on a podcast publicly. But for people who want to like build a social following, I think you really have a good playbook for that, which was actually write good work, first of all, which is hard enough, but then share it with like people who have distribution and you earn distribution if you give them good things to distribute. And like, it really is that simple if your work is solid. And so I think it speaks wonders to your journey and how you got to where you are. What would you say is like the thread that ties all of that together? Like, obviously, I see a lot of, you know, consumer throughlines here. There's a lot of crypto stuff. There's a lot of putting out your work publicly. What do you think is the number one theme that kind of drives the last couple of years until now in your career?

Yeah, it's gonna sound like I'm like taking myself so seriously. And I promise I don't. But no, so what I would say is storytelling. Is the thread from like me being a kid to stuff that I did in high school to loving to write, to going into venture, which is I started out literally, no pun intended, without a voice and wasn't able to share that. And then as I gained a voice, both physically as a kid and then kind of metaphorically as I got older. And became in a position where people would look at the things that I said, I realized that the ability to tell compelling stories is really, really powerful and meaningful. And specifically capital is a really great way to tell stories. And so it's a real privilege to be in this position where I am a steward of many different people's capital. And I can use that to tell the stories that I care about. Or even if you think about, um, in Web3, when you have this public ledger of information, the data actually becomes media and the stories that you can tell from on-chain media are really powerful. Or, you know, like the different interfaces that allow us to connect with each other online and offline are all really powerful. And so I think that is sort of the through line for it. And specifically, I think one of the edges that I've had in my career is being someone who can tell those stories. So I happen to love investing in consumer, but even if it were something else, I think I would be writing just as much because I think it's really powerful to make things meaningful to other people.

Totally. So I know that we, let's double-click on that because I know that we've talked a lot about now, you know, how you relate to technology and the internet and your Coming up into venture and crypto more broadly. Let's double-click on crypto mainly through this lens of, you know, interfaces and kind of the saying that we shape our tools and then our tools shape us. How do you think, you know, the different interfaces that have been designed in crypto impact the way we use those applications today, or more broadly unpack this idea of, you know, we shape our tools and then our tools shape us in crypto?

Yeah, obviously I didn't come up with that. It's been around for a hot minute and it's true outside of crypto. But I think it's really worth exploring of, I guess what it comes down to is at least from like a, like a tech perspective, distribution. And, and this, this might be a hot take. I don't think it is, but I think there's a misunderstanding where a lot of people believe that if you have a really beautiful product or something that operates really well or is very high quality, That, that is the answer to your problems. And it's always been my view that distribution is king, and it actually doesn't, to a degree, it doesn't really matter how good the product is if it helps people do what they want to do and it makes things more convenient. And a lot of that comes down to the actual medium or the interface. And so one example is MetaMask. So MetaMask surged from half a million to like 10 million users in a span of a year during DeFi summer because That was the easiest way that you could engage in DeFi, you know, buy, sell, and hold tokens. And now there are a lot of things that you can do in Web3 that aren't DeFi, and there are a lot of wallets that allow you to do those things. But to a degree, MetaMask is still such a popular wallet because it's the most convenient, right? Like everybody allows you to connect with MetaMask and it's right on the browser, and most of Web3 is browser-based. And my view is that as new products emerge in Web3, the wallet that allows you to interface with those things 10 times more easily than MetaMask or whatever the other incumbent is will win. I was actually listening to a podcast today that my partner Jared sent me kind of along this same line. Let me find it. It was an Invest Like the Best podcast with Bob Pittman from iHeartRadio. And MTV, and I think Six Flags also, but I haven't gotten that far in the podcast yet. And he talks about that too. But a good example is the microwave that he talks about in this podcast. The microwave, and Zach knows I can't even talk about this cuz I don't have a microwave in my apartment. It's actually so annoying.

Worst part, just a toaster.

Worst part about my apartment is I don't have a microwave. And this is a perfect example. Microwaves do not make good food. Like food does not taste good.

Oh, okay. No, no, no, no, no, no. That's a lie. I need to, I need to cut you off there. That's a hot take. Have you, you haven't seen David Chang from Momofuku on TikTok talking around how microwaves are like just a really expensive steamer?

Yeah, but it's like, okay, if you're going to make a pizza in an oven or a microwave.

Okay, fine, fine, fine. It's bad.

Oh yeah, yeah, yeah. If we're talking pizza.

Well, no, but this shows like I would actually rather make something in the microwave than make it in a place where it would taste better. Because the convenience is so important. So now it's like, oh my God, the amount of microwavable foods that I buy at Trader Joe's because I want an easy lunch and then I have to preheat my oven to 425. It makes me want to freak out, like literally freak out. And so now I only eat cold foods and I eat toast because it's all I have. So anyway, the microwave is a really good example of convenience over quality. I wrote a piece yesterday about messaging, and I think that that is another good example. And this is not to meant— this is not meant to be a dig on like companies who are building in Web3 messaging. If anything, I think it's like one of the most exciting spaces to be building in. And I think that a lot of them have been thinking about what I wrote about for a lot longer than I have. So not to say that I'm the first person to think about this stuff, but, and I also co-wrote this with someone on my team, Sophie, who's amazing. So we'll put her in the show notes too. Mm-hmm. But basically, the interfaces that allow us to communicate via the wallet are not good, and so we don't communicate via the wallet. The interface changes the way that we behave. So I'll give you an example. You can actually send on-chain messages right now. It's very possible. And actually, every now and then, if I'm like poking around on Etherscan or another block explorer that I like to use, I will find these messages and I think it's kind of funny because people kind of think that they're private and they're obviously not private. So it's fun. I saw someone applying to a bunch of different jobs in crypto sending like, you know, popular VCs these resumes.

That's smart.

It's so smart.

That's interesting.

And I don't even know if they see them because if you wanna see it, what you do is you have to go look at all of the transaction hashes that are associated with the specific address. Then you find one that says, 0 ETH was transferred from one wallet to yours. Then you click on that transaction hash. You have to scroll down on Etherscan. Then Etherscan makes, makes you click a button that says more. You click the more button and you see it, and it's a string of very confusing numbers and letters. And then you have to convert that to UTF-8, and then you see what the message is. So obviously, like, why would we expect anybody to send a message that way? Because nobody's reading them. Then it, it kind of goes beyond that of like, okay, fine, let's make an easier way to send a message. We're probably still not gonna use it because Telegram and iMessage and whatever else people use as their daily drivers are still the most convenient way to send a message from one person to the next. So the goal of Web3 messaging, in my opinion, should not be make a Web3 Telegram, like make a Web3 peer-to-peer messaging tool, because peer-to-peer messaging is not really that interesting because Until you make something 10 times more convenient, it's not gonna be used. And I don't really know what a more convenient version of iMessage or Telegram is. So that's not really the goal. The goal really is to figure out what is uniquely enabled by the fact that this is crypto, and it's the fact that you can unlock a new recipient of the message, which is the protocol. And that wasn't possible before.

Hmm.

Without crypto. So I'll give you an example. I use Forecaster, and in the feed you can see the NFTs that people buy.

Mm-hmm.

So I start my, I start the story on Forecaster. I find an NFT I wanna buy, then I go on OpenSea and Foundation and any other marketplace that I'm looking at to find the best price for the specific NFT in that collection that I wanna buy. And then I mint it on MetaMask, or if I'm on my phone, I'll probably use Rainbow. And then from there it ends up in my wallet. And then if I wanna engage with the project, I've gotta follow them on Twitter and I've gotta go on their Discord or their Telegram, and then How do I make sure I get announced by new projects? Or maybe, I know you guys like the Nouns community, you've gotta go to the Nouns Prop House. And it's like, what the hell? Like, why are we going to all of these different places? Why don't we centralize it all, maybe in the wallet, and you can still protect the identity of the consumer and you can message and you can interact with the protocol? Because if you think about it, when you connect to the Nouns Prop House, you're signing a message with your wallet. Like the, the, the, the messaging between wallet and protocol already exists. And so what if we treated every single on-chain action as if it were a message? And then what type of interactions might you be able to unlock when the interface is actually better?

That's fire.

So do you feel like, yeah, that's great. There might be this one quote in here actually that I re— Yeah. Damn. Yeah. I wish sometimes, do you ever wish like your job was just a little bit closer to like a rapper or like a, like a, like an athlete? Like, I feel like they get these moments where it's just like, bam, like celebration, everyone claps. Like, I feel like we don't have that for like VCs. Like maybe we need some sort of like VC alternative where like people can just go crazy.

Well, that's VC Grimes.

You had this one cool— I didn't invest in FTX. Mic drop.

Yeah.

There's, you had this one quote in here that I really like that I think sums it up pretty well. We hear a lot of conversations around hooks for crypto-native messaging, like permissionless social graphs, verification, and token gating, but these are features of Web3 messaging, not the core use of it. I feel like that really summed it up super well. So is your take on this then that this doesn't get solved with like, because the, with, there's gotta be messaging apps out there That like the user journey that you kind of described where to figure out the message that someone sent me, I have to really dig through Etherscan or something. There's gotta be apps out there that just like make that slightly more easily, more slightly easier. Do you think though that this just gets solved at like a higher level where like, it's like the entire interface is completely different where you're not interacting like with Etherscan and MetaMask? And some other app, it instead becomes kind of all just one interface basically. And so sort of like, I don't wanna say super app, but kind of like that, uh, is it vertical integration?

Yeah. Yeah. We called it a super app in the piece. I don't know if there's a better word for it. I think a good example right now is Daylight, which announced their fundraise this week. Yeah. And I, I think it's been launched in beta for, for a little bit before that. And I think that's a really cool example of where we're going, of centralizing all of those, you know, if we call them messages in the wallet. And now the wallet becomes— and Zach, you've called the wallet like an email inbox before. Now the wallet—

I was going to bring that up.

The wallet really does become an inbox because you get to log in and you get to see like what's new. Um, there's another block explorer that I've been kind of testing out that I love, and it almost has a similar inbox feature of You can follow and track different addresses on like the sidebar. And, you know, let's say I haven't logged in for a week and then I log back into the block explorer a week later. Mm-hmm. The addresses have little notification buttons of like, oh, this one has done 10 new on-chain actions since you last logged in and you get to see what they are.

That's cool.

I think that's cool too. I don't totally know what it will look like, but I, I've always been biased to having the sort of like nexus of identity be central to the wallet. I've always viewed it that way. And I know not everyone agrees. So I'm sort of biased to believe that it will take place in the wallet, but I'm not totally sure.

So what do you think is like, what's on your request for startups in that space? Like, I know you and I have talked about, and you've written about this, like, you know, wallet as an email inbox. And as your life becomes, you know, more rich online, you're going to have to be able to triage all of these digital assets. What sorts of projects are you looking to fund or what sorts of projects have you been seeing that are doing things in a different or interesting way in that space?

Yeah, 2 companies that I think are cool that we're not investors in, but I think are interesting are Lines and Dispatch, which are both on sort of like the quote unquote B2B side of things where basically one of the areas where Web3 is actually really exciting is for businesses to have better understanding into who their customers are. And so if you have the wallet, now you understand not just who they are and what they've purchased from you and that type of history, but also where they spend time elsewhere. And obviously this really only works at scale, like if lots of businesses are using the wallet as a means of identity, but it is cool to think about like, okay, Let's say you've connected your wallet to like X clothing company and you see that a huge percentage, the company sees that a huge percentage of connected wallets also buy at this other store. Now it becomes really interesting and really easy to do types, these types of like partnerships and collaborations and build loyalty programs cross-platform and be able to track where people spend time all across the internet and not just on your site. I think that's really cool. The problem is you see companies realize that and start to do that, but it really means nothing until you can talk to the wallet. And so now, you know, I think like Web3 companies are the best examples here. Like you connect your wallet to OpenSea or you connect your wallet to Mirror, but you still have to give them your email because it means nothing unless they can tell you what to do with that connection. And so the ability to actually talk directly to the wallet And not need the email address, I think is a big unlock. And that's what Lines and Dispatch are both doing. And I think there are other companies in the space as well.

Kind of with that. Yeah. If it's something I was thinking about recently connected to that is who, who has the best, the biggest database mapping Ethereum addresses to email addresses is something I was thinking about. And I think it would be probably OpenSea or maybe Premint, like they did the NFT minting like waitlist, but they, there's probably a ton of bots and stuff on there. But wouldn't you say right now, I mean, it's different, but for example, if you have like 300,000 Instagram followers, you don't have their email addresses, right? You don't have that. And you can still build a viable kind of business or whatever you're doing without having that. Do you think it's—

Yeah.

Like, how do you reconcile that? Because I feel like there's a world where people just build these really good lists of, hey, I have this person's Ethereum address and I have this person's email address. And therefore, like, that's inherently like way more valuable. Is that not like the end game? Like, it feels like there will be a need to communicate to Ethereum addresses, or you think this, it can survive like this for a long time, basically?

Meaning we can survive with the email and with the wallet for a long time.

Yeah, because for example, on Instagram, it's like you don't get DMs from, you know, the celebrities you follow, right? We have, we have a similar state, I think, with social media as we do with crypto. And it feels like it's like stable enough. So why do we need it in crypto? But maybe that's like not the right way to approach this. I feel like I don't know if I'm approaching this in the right way. It's just that like, we don't have a way to communicate to Instagram accounts, for example. Um, so why do we need it for crypto?

Well, that, I, I think if I'm understanding correctly, that is exactly the problem. Like, like businesses might have an email, but I might be super engaged from Instagram and that might actually be the best place to engage me. Or like, they, they don't understand who I am on Instagram versus Facebook. Versus email versus signing up for text updates. And you kind of see that businesses are really hungry to get as close as they can to the, to the customer. Like, give me your email and then sign up for text and you're gonna get 15% off. Like, that's how badly they want it.

Mm-hmm.

How do you make that easier for them to have insight into who the customer is? And the big part is how do you do that while protecting consumer identity?

Yeah.

And I think that's why the wallet becomes more interesting.

Do you view the wallet as like a deeper relationship with the customer in that way? Like if we're, if we're talking about the kind of cascading effect of the different pieces of info you ask from a customer, an email, uh, you know, their actual physical address, their phone number, where does wallet fall on that hierarchy in your opinion?

I think at scale, when you have the network effects of like lots of businesses acting this way, and the ability to communicate to the wallet, my view is that it becomes the most important because most of these businesses are internet-native businesses. And like, they're not like stores that have, that, you know, like are mostly like brick-and-mortar retail, you know? It makes sense to have an internet-native identity layer as well, sort of how I view it.

Have you changed your mind at all about the The idea of like embedded wallets versus almost like an all-in-one wallet. I know a while ago we talked about this idea of like, you know, a fashion NFT marketplace may not want to have people just connecting their MetaMask wallet, but instead you want a place to show off your clothes like a closet, right? Or if you were to have a, I don't know, a gaming, like a Call of Duty, you know, on-chain game, you might have your war chest instead of a wallet. Right. And so do you think that this new piece that you wrote conflicts with that viewpoint that you would have like embedded wallets that are verticalized and focused? Or do you think that this just means that, you know, in that world where there are verticalized wallets, we're still thinking of the wallet as both a kind of place to hold inventory and assets, but also a way of communicating?

Yeah, I mean, it's sort of— it's like it's either apps in wallets or it's wallets in apps.

Hmm.

So I guess my original, my original view was, was wallets in apps. Wallets would be embedded inside different applications. And so if you're like a digital fashion marketplace, you have a wallet there and it only shows the things that are relevant. And the same for gaming and maybe one for DeFi and whatever. Yeah, the messaging layer. Well, the, the view is they're probably all the same wallet.

Mm-hmm.

You may have the same private key. across all of these. And there are companies building in this space, but the interfaces of them are different. So I guess it's still probably in line with the thesis of like, you have the wallet, but different interfaces are embedded in different applications.

But for sure.

Yeah. Curious what you guys think, because I know not everyone agrees.

Yeah, I think I probably fall in the middle of that spectrum. If one side of the spectrum is, you know, The app has it, or the app is basically a wallet that has access to your keys and can sign transactions versus a wallet that has underlying plumbing, connective tissue, whatever you want to call it, to the underlying protocols and applications. And those sit within the wallet. I probably sit in the middle there. I actually think that the solution to this is essentially a hybrid between a block explorer and a wallet. So a block explorer where you can very easily see what's going on on-chain, you can get those notifications that you were talking about earlier of, you know, following or getting notified about certain contracts or wallets. But you're also able to sign transactions and go take action on-chain from that same interface. And so I think that like, my answer has shifted from, you know, wallets get embedded in the applications to it's actually both. The wallet is the application. So that's kind of embedded. And then the applications are very easy to interface from that one UI. Um, so it's, it's an ever-evolving thesis, but I think it's, it's somewhere in the middle of what you described.

Yeah. I think a cool example is WalletConnect. Obviously WalletConnect is basically like the communication layer for all of it. So it's not like they're building all of these different wallets. It's just a communications protocol, but I think they view it in the same way of like, how do you push forward and encourage different interfaces. You know, if you scroll down to the part that says we connect you with more than 450 apps, and you can see all of the different applications, and maybe your wallet will look different on these different applications connected by this, by this communication tissue, sort of.

Yeah, that's super interesting. Martin, I know, I know you had another topic we wanted to touch on before we wrap up today. Do you want to bring that one up and we can then Absolutely.

This is maybe my favorite topic ever in the history of the 2 episodes we've recorded from this podcast. It's a little silly and directly relates to the podcast name Infinite Money Glitch, which at one point I wanted to call the podcast like Magic Internet Money or something like that. And I think this directly connects. Gabby, can you explain to us what doubloons are and What we should take away from them. Well, I know what they are. Can you explain it to Zach? Because he's, he's not well versed.

Yeah. So I'm not— fill in my gaps if I miss some stuff. But basically, well, I call them doubloons.

Yeah, I have no idea how you pronounce them. So go for it.

But basically, I've never even seen these— this thing.

See, you're obviously not—

is this like a tick?

Not chronically online?

Is this a— is this a new TikTok trend?

Yeah. So basically, it's This new digital economy that has emerged with millions of people. And I imagine someone started one video that kicked this off, but they, they created this currency called the doubloon or the doubloon. And it's, it's named after this coin centuries ago. I think it was like the 15th or 16th century called the doubloon. And now it's what it is. And like I said, before we started recording, this is like the modern cheese touch. Mm-hmm. Where you'll scroll over a video and someone will get your doubloons, or you'll scroll over another video where someone will take them from you and people are bartering and like different things are happening in the doubloon ecosystem. And it's basically an honor system to keep track of how many doubloons you have. And this is why TikTok is so cool because you don't ever have to post a video on this application to be a part of it. Because you see all these people who don't even have profile pictures, they don't even have usernames, but they're in the comment section like, holy shit, all my doubloons just got stolen.

It's like a meta DAO.

That is such a VC thing to say, Zach. Just some fun little TikTok trend. You're like, yeah, it's like this little DAO concept, dude. I don't know. No, this—

now what are the terms?

Yeah, Martin, Martin put in our chat it's Web6.

Literally.

But I'm investing at a 50 million doubloon, uh, No, I feel like, I mean, this is the first time I'm hearing about this. But it all— what I comprehend it as is essentially this, like, community that lives in people's heads. And so it's the complete opposite of, you know, crypto and the trustless systems we're trying to create. It's like the most trustful system because it only exists in your head.

Exactly.

That's interesting.

I think it's, it's like, So I have a few takeaways from it as I was thinking about it a little bit more. But yeah, basically, that's all I know about it. I don't think there's that much to know. It's just that like the money is entirely real and entirely fake. And so it feels like a, it's like a role play, basically, is kind of how I think about it. Like, I think some comparisons are like Dungeons and Dragons type stuff where it's like you're just kind of making up the stories and stuff as you go. And there's maybe some element of realness to it. But generally, you make it up as you go. And it also reminds me, this is like super niche, and it unlocked this memory for me. But I I used to play a lot of Wizard101 when I was kind of late in elementary school, which was an MMORPG for kids basically. And I was part of the— I was very active on the Wizard101 forums. That's kind of where I actually started learning about graphic design. And one, at one point they added this category called like role-playing games or something like that. And I didn't really understand what it was, but after a while I figured out basically people would create a thread and they would be like, all right, like in this post we're basically just gonna like roleplay Harry Potter. And so you have to reply and you have to introduce your character and like, you know, what house in Hogwarts are you in? And like, what's your backstory? And then you would like act out stories basically. It was just like, you know, at recess when as a kid you would like come up with stuff. It was the same thing, but like online in this forum. And I think the balloons definitely just like connect with that for me where it's like, um, just this like made up world, but it is with money. And it, it just made me wonder like, There's another crypto thread, which is what if you just had some blockchain where it was just all, maybe this is testnet, but it's all like fake money and you can reenact like hacks and just like roleplay on the blockchain or something. I don't know.

It's kind of cool.

I think it's pretty fun.

Wait, but what if that is Bitcoin?

I, I didn't say that. I think we can edit that one out.

It, I think it's not, not crypto. Like, I think sometimes when I read about the doubloon stuff, I'm like, this is probably how people feel about NFTs. They're just like, this is not real stuff, guys.

Like, it's just not real.

It's like when you think about, so, so like I, I've had people ask about like Web3 insurance before. I promise this is relevant of like, how do you build a Web3 insurance product to like insure your NFTs? And the problem is, sure, we don't know how to value digital assets. Because so that's the real issue. The issue is not insurance, but it's how do you actually appraise these things? And you've got a lot of companies trying to do it, like Upshaw and Abacus and like all of these other companies. But, but the, but the fundamental issue is like an asset is worth as much as what someone is willing to pay for it. And that could be extremely different from today to tomorrow. Like think about Azukis, right? Or think about like, I don't know, there are so many examples and like, It's this collective suspension of disbelief to, that makes the whole thing work. Yeah. It's also the dollar. Okay. Like I didn't say that, but you know what I mean?

Yeah.

No, I agree with you. I agree with you though.

Like it's not, it has nothing to do with crypto, but it's more about like, how do we value things? Um, it's also, I'll just, I'll plug one of our investments, which I think is like fun and a cool working example of this. It, it kind of feels doubloony and actually He was gonna call the currency doubloons like months ago. So hopefully it's not like, doesn't sound like he copied it, but, but it's this game called Castaways, which is like an online Mm-hmm. Web3 game. And it's basically like Minecraft, but you own the assets and the game doesn't work unless you play it. Like, like the assets are not valuable unless you build on the island and you fish all the fish so you have a monopoly on them and then people need to buy the fish from you. But maybe you're a tomato farmer, so then you get a good deal on the fish cuz they really need your tomatoes and like. People are really playing and it's really fun to hop in and see what's going on. And it's like, it's giving to Bloons, you guys.

It's pretty amazing.

I think there's gonna be some, uh, some interesting, like, um, almost like, uh, Animal Crossing meets like Crusader Kings meets Civilization meets, uh, on basically on-chain. I think there's, and that gets like into the really like the The great online game kind of aspect of it. So I think there's definitely something, there's like something there. It's not like, it's not nothing. I mean, it's just like kind of kids playing around and having fun, but I think there's definitely like connection of like this understanding of like digital, like narratives and digital currency and who can control that. Because I, something I was actually just thinking about is, okay, I honestly don't really understand how the Ethereum blockchain works at like the smallest levels. But my understanding is that you can create a fork, right? So in theory, I can create a fork of Ethereum where I stole all of Zach's money, which is not that different from a TikTok where I say, hey, I stole all your doubloons, right? So there's some connection there, but it's light. It's not a big connection.

Yeah, it's like, you know, it's forking technology versus forking reality in this case.

Exactly.

I know.

Well, that's a whole other conversation about how technology actually influences reality. Like, oh yeah, I, I haven't published this piece yet, but I talk about how, like, I'm trying to think of how, what I would call this, but like the fact that the Museum of Ice Cream exists means something about how our digital world is mirrored in our physical life.

Hmm.

Yeah.

I'll just leave that there.

That's interesting. Yeah, it's super interesting.

Great teaser.

Eric, Eric Thornberg and I wrote a blog post that I'm like struggling to remember the name, but it was similar concept of how like, you know, when we all live on the internet, reality just kind of fractures into thousands of shards of what we think is real. And everybody in their own way, from their own perspective, is trying to piece together all of these, you know, different shards of reality to create their own vision of what's real. And it leads to some pretty weird effects, as we've seen over the past couple of years. But I think there's, there's some tie-ins there, Gabby, with your Museum of Ice Cream piece, and can't wait to read that. So I guess to tie, tie things up in a nice neat bow and wrap us up here, obviously we've talked about a lot, you know, our relationship to technology, your journey on the internet, Gabby. What sorts of things are you excited about in the future? Like, as you look forward into the next handful of years, I know It's it's very easy to pull up, point out you know negative things like the FTX collapse or just broader macro markets. But what's exciting you these days? Or what idea do you want to leave our listeners to simmer on until next time?

Yep. Well, if anyone's listening and wants to DM me about anything that we talked about, I try and read most of them. So please feel free. The two areas.

Yeah, plug your socials. Where can people find you?

It's @gabby_goldberg on Twitter. But in case If that doesn't exist by the time this goes out, I'm @GabyOnForecaster. And what else? I need to get a newsletter going because I have an email list or something. But anyway, the things that I'm thinking about from a, you know, obviously personal but mostly professional perspective are new models of media production, whether that comes from blockchain data. Um, I don't invest in AI. I just think it's interesting of like how AI is changing the way media is produced. And then the other one is future of stuff that's happening on mobile. And this matters for a lot of companies, but particularly Web3 and crypto apps that have a hard time getting put onto iOS. I think mobile web apps are super interesting and there are a bunch of companies that have found success on mobile web apps. And so the future of what that might look like, I think is really interesting. Um, and then Last thing I'm thinking about that I'll leave people with, and maybe we can talk about another time, is like this idea of like a dopamine detox, like we talked about at the beginning with getting rid of technology. And what I've been simmering on is I wonder if I continue to have a dopamine detox, if my apartment will have more color in it than it does right now. Because the last, I don't know how to say this in a sentence, but because I consume so much media. I think I get overwhelmed and my apartment is all white. It's a sensory deprivation tank because I need a place to cope with the fact that there's so much going on. And I wonder if I delete these apps and I put my phone on grayscale, if I'm going to start buying artwork and put colorful blankets in my room and things like that.

That's so interesting. Yeah. I mean, I noticed since going to grayscale, even my daily walks outside feel that much more beautiful these days. So I'm sure that it would help some impact. Very cool. Well, Gabby, thank you so, so much for your time. This was a great, great conversation, very wide-ranging, and looking forward to hopefully having you back another time to chat through some of that other crazy stuff soon.

Thank you guys so much.

Thanks, Gabby.

You guys each get 2 of the balloons.

Awesome. Thank you.

Thank you.

Hopefully not steal all your balloons before next time.

I stole Zach's.

Yeah, I'm poor in balloons. Oh well.

I'm rich.