Ep: 229 - Boys Club Live: Digital Asset Summit, Token Management, Macro Perps, AI Fruit Love Island, with guests Lindsey Winder and Kaledora

[00:01] We'll be right back. [00:31] you [00:33] Great, great. We'll never, never not be terrified of a hot mic. We'll never not respect a mic situation. We've had too many hot mics. Hi. How's it going? How are you doing? I'm so happy you're here. I'm so happy to be here. Got up at 4 m. I know. To get here from Nashville. I know. When I saw you on the street, I was like, man, she's journeyed. She's lived many lives. I've lived a full life. But happy to be here. Happy to be back.

[00:59] In the studio. In the studio here. Our friends. Kate. [01:03] just so people know, is head to toe in a McDonald's fit? [01:07] Which like [01:09] Doesn't surprise me a little bit. Actually, that's not... There she comes. Come on. Let's go on. Calm down. Okay. I think I need to show people that it's like a velour tracksuit. How would you describe this? A velour tracksuit. [01:22] Oh, and the tie. I didn't... [01:25] Oh, Japan, Tokyo. You got this in Tokyo. Could you show the back the, um, yeah, particularly the, exactly.

Incredible. So great. Incredible stuff. [01:34] She's got a jacket as well, an additional jacket. Anyway, Kate, love the look. Just always coming through. Love it. Okay, I need to share my pants. [01:43] Now it's time for you to show your pants. A little bit of a crisis that I'm having with my pants. Okay. I have, I'm so, we have been wanting to talk about these pants all morning. And every time Dean is like, shut up. We have to save it. It has to be on the live. Save it for the show.

Well, mostly because last week on the show, it was last week, right? It was last week. Yeah. [02:00] about me [02:01] searching for this type of trouser. Yes. Which I'm about to show, which is a trouser, a normal trouser with a skirt overlay. Yes. [02:10] I put it in our company Slack and said, Kate, can you help me find a dupe? She sent me back within five minutes. I do have to say there is a percentage of Kate's time that is... [02:21] allocated to that. Yeah, it was on a Saturday morning, so I didn't eat into company time for this.

But she very quickly wrote back, [02:33] with five links. [02:34] to incredible work com pretty little things is to move i think is where i ultimately got these [02:41] Pretty Little Things, is that what it's called? [02:43] Oh, that's the name of the brand. [02:45] I got the pretty, I don't, this is the first time I ever ordered from this shop. [02:49] Did it come quick? Usually I feel like really quick, really cheap, like 20 bucks. Anyway. Okay. It's time. Yeah. It's your moment. Here's the pan. Let's see. [02:57] Also, [02:58] I'm not Mike, so I need you to say what Mike is saying.

[03:02] It's giving waitress. It is kind of giving waitress. No, it's giving apron. It's giving apron a little bit. [03:12] That's the vibe I've been... [03:16] Thank you. [03:18] Kate's saying it's a popular vibe. [03:21] Yes. [03:23] I literally felt like I had a black, I think maybe I also need your styling help. [03:29] No, I was like, someone might think I'm like bussing tables. Someone's going to be like, can you take this cup? I have, I just want to hit you with a link. I do realize they're more expensive than, okay.

So my first exposure to this type of pant was Blake Finucane, our friend of the pod. The Ghani ones. The Ghani ones. $350. I know. I'm just telling you where it came from, where I've landed. Okay. They're $350. I'm feeling really defensive about the price because I'm also feeling like I should have [03:59] probably but we're just gonna back into it okay so [04:03] I saw those on her. I was like, I'm obsessed. I made a rule for myself. I can't buy any more pants because I love to buy weird pants.

And then just a bunch of weird pants. So I was like, I can't buy these. [04:13] Not that I was going to get the Ghani ones, but I was on a similar journey to you. This was in Abu Dhabi. This was in December. Okay. [04:20] The Ghani ones, then I have a favorite store here in the city called Pesh, which is sort of like maybe Korean, unclear, in the Lower East Side. [04:31] um that it's like a one size shop so it is a little like a a little bit of a problematic space it's it's it's modern brandy melville it's right okay and they only have most their shoes only go up to like a size eight okay it's for us a petite lady some shoes go bigger anyway they have this pant and i'm gonna i'm gonna send this to you kate to pull up

[04:55] that is a middle ground. Okay. $176. Okay. So, you know, a purchase, but not Ghani 350, 400, whatever they are. And it gives less waitress. [05:09] They have two size categories. Two size categories. Okay. Anyway, they're... Can we pull them out? [05:17] The Ghani ones are great. The Ghani ones are so beautiful. Also, the ones that I... [05:22] originally sent you the dupe for are also beautiful $350 from what were they? [05:27] they were wool, they were wool. Will? [05:30] what's that brand Paloma oh Paloma wall oh my gosh the best gorgeous gorgeous gorgeous um [05:38] Also, I will say just one note on this.

[05:41] personally would like a longer skirt that's the thing that's why it looks apron yeah it's like too mini skirt yeah it's okay and then kate pull up my patch one and then we can move on from the pants pants department [05:54] Thanks. [05:54] Oh. [05:56] Nice. 175. We could go today. They're sold out online, but we could go today before we flight. We've got a lot to get into. If I can't fit into those, I'm going to have some feelings about it, and they won't care. They've designed for that experience, only stopping one size.

[06:12] Also, I feel I need to address... [06:15] what it sound like um i'm not i'm i'm no longer contagious [06:19] According to... [06:21] my general project manager who is chat gpt um but i do sound like shit and um i apologize because it's kind of gross at first i was like oh kind of hot and now it's been like yeah 10 days and i'm like [06:33] Not so hot. Yeah. Time to get better. Maybe we should get into like a hot, like a heated room that doesn't have anyone else in it.

[06:41] Small, solo heated room. Okay. So we have a fun show coming up. We have two guests that are going to join us. Lindsay Winder from Anchorage and then Caledora from Ostium. [06:53] both who we have a lot of questions for. So we're really excited about that. And then [06:57] Actually, before we get into things, shall we give a quick shout out to our partners here? [07:05] Kate, you let me know, Octant, when we're ready. [07:12] So we love Octon. [07:14] as we love often they are well known in ethereum circles for [07:20] their tireless contribution to the Ethereum ecosystem through research and millions of dollars in grants and public goods funding, [07:26] 2026 is their product era.

Octant is now laser focused on vaults. If you tuned into last week's episodes, we had a long conversation about vaults and the interesting stuff they're doing there. Vaults enable orgs and communities to build sustainable funding systems through yield generating products. [07:44] Basically, you... [07:46] Put your capital into these vaults and then you can direct your yield towards your own orgs runway or funnel it to broader ecosystem efforts. It's all fair game with Octon's new institutional grade vaults. Earn, allocate, and grow Ethereum with DeFi. Check out Octon at OctonApp on X.

I ran into the team yesterday at DOS. Yes. [08:12] And... [08:13] Just so lovely. Really lovely people. Really doing the work. They are very thoughtful, smart, [08:19] people and had a great conversation with them about [08:22] work and then fiction. [08:25] books. Oh, any recommendations? Some fantasy stuff. Okay. I have it written down somewhere. [08:32] And anyway. Man, I have not been reading. I need to get back to. You got to get back on it. It's so nice. I love it. You have to like hit the hieroglyphics. Yeah, I've been, I, you know, I run my book club.

Yes. And we've, [08:48] read two books recently one that i would recommend the other that pissed me off um one was heart the lover okay [08:55] I would recommend. Great. Easy. The type of book where you're like, you can't put it down, but there's some like really beautiful writing in it. And then the second is like a memoir that's like kind of hitting like New York. Like I'm like seeing it all over the timeline. People are talking about it's called Strangers. It's, um, this woman who's like, um, [09:10] like comes from like a socialite family.

Okay. And... [09:15] Anyway, it's about her divorce and basically COVID happens and her husband just one day after 25 years, I'm out. And it's about that. And we'll have the book talk time here on Boys Club Live. But not recommending that one. [09:32] I think is a very, like, you could read it in a sitting, like... [09:39] I was in Mexico City last week for Stripe Commons, and I was on the plane with... [09:47] Um, [09:48] a few friends who are on the book who are in the book hub who are also working crypto so there was three of us like all reading this book strangers which it was funny and also so many crypto people on this plane which you know i hate brutal and i do have to say [10:01] Just shout out to a friend.

[10:04] Who... [10:05] A colleague, not a friend, who was on the plane with me, who did have the seat next to me, who I did not talk to the whole time. [10:13] I was just like, headphones on. I'm not here to do that. I'm not telling you. I'll tell you afterwards. [10:20] But I literally, he sat down and I was like, [10:22] And just like, yeah, not doing that. Anyway, that's a gift. That's a real gift to you. So that's both, I feel. Totally. Both of you want to. And everybody around you.

Like nothing's worse than like two chatty Cathy's on a plane at 630 in the morning. I had one coming back from Nashville. That was a lady who was just like really. And you know me. Very hard to. Oh, my gosh. Very hard to. Absolutely. No way you're getting out of that. Very hard to chat with strangers about. [10:45] stuff so it's like what do you do for work and you're like let me show you my podcast we're talking about our totally and i'm like we're talking about my boots i'm like what are we doing here but i guess that's that's humanity and i have to leave space for it but it was very i was very challenged by it yeah so anyway that was anyway thing that your seatmate did strangers um most of us finished the book on the plane so like it is a book you can't put down but i have [11:07] Some thoughts and feelings about the [11:09] whole premise of it so if you'd like to join my book club just dm me on twitter a spin-off uh podcast [11:15] Let's hear it.

[11:17] Of the book? The book is 2.5 to me. Out of five? Out of five. [11:24] Okay, so mid. Yeah, mid book. Okay, should we give a quick shout out to Anchorage? Yes, we should. We have an incredible tape we're about to roll. [11:35] In one moment. [11:39] If you haven't yet seen this, you're in for a treat. [11:44] - See this? This is your cap table. You made it in Google Sheets at midnight. It's got 47 tabs, three conflicting versions, and you're emailing investors one by one, asking for wallet addresses manually in 2026.

Why are you working twice as hard? [12:06] Anchorage Digital. Anchorage Digital's full stack token management solution. One dashboard. [12:13] CLIFFS, LOCKUPS, IT AUTOMATES STAKEHOLDER COLLECTION, SO YOU NEVER SEND ANOTHER JUST FOLLOWING UP E-MAIL AGAIN. POST LAUNCH, YOUR TOKENS ARE HELD SAFELY AT ANCHORGE DIGITAL, HOME TO ANCHORGE DIGITAL BANK, THE FIRST FEDERALLY CHARTERED CRYPTO BANK IN THE S. AND THEY'RE NOT JUST SITTING THERE. YOU CAN TRADE, DISTRIBUTE, STAKE, AND EARN REWARDS WITHOUT YOUR TOKENS EVER LEAVING CUSTODY, VIA ANCHORGE DIGITAL'S FULL-FULLY FEDERAL. [12:34] fully integrated offerings. And your investors can easily access them through their own portal.

If time is money, then make sure you use Anchorage Digital to get hours back. You following me, camera guy? You're not going to need this anymore. Go to com or call 1-800-AT-ANCHOR. Don't really call. [12:49] Thank you. [12:53] I do just have to say, we recorded that two weeks ago here in the studio, and... [12:58] I was just like... [13:01] blown away at the acting that was happening from Kate. I was like literally could never like it was Wes and me and Kate and Wes was just like okay go and Kate was like [13:12] Line, line, line.

And I was like, I felt secondhand. [13:19] like stress yeah from it and i was just like man i know she a real one she'll come out and she'll surprise you with her talents many talents uh should we bring our first guest [13:28] up utility player uh lindsey come on in um hi come on down here nice to see you nice to nice to see you hi um you can slide in make yourself comfortable i will say it's a cozy couch it's a cozy couch it's kind of a [13:47] bar back couch okay you seem fine right do i sit like this one no no no like adjust yourself however you feel most comfortable and then we can adjust your mic [13:56] We've had some guests who, unfortunately, their feet are up.

You don't have that problem. We're in a good spot. Like a perch. You look great. Okay, Lindsay Winder, Token Vesting Lead at Anchorage Digital. Welcome to the show. Thank you for having me. Great to be here. I'm so excited. Great video, by the way. I just got to say I was watching it again. It was incredible. Thank you. Thank you. [14:26] Okay, so you were at the Digital Asset Summit yesterday. Digital Asset Summit yesterday. [14:34] DAS or DOS. DAS, DOS. [14:37] as some as some may call it um what was your take [14:41] I love DAS.

I went last year and it instantly became one of my favorite top two conferences of the year. Same as last year, I feel like there's so much energy there, which is like what you want to see at a conference. [14:56] It's a completely different group of people than we see on our kind of like global conference circuit. [15:02] So it's a group of people that... [15:05] aren't usually present at those other ones and the energy and excitement and just seeing what people are building. It's, [15:11] So it got me into crypto.

But now seeing it on this different kind of level than, you know, six or seven years ago with institutions and just new builders. [15:21] I was incredibly excited being there yesterday. It was great. [15:26] Yeah. It's crazy. Just the scale that it's hit and the seriousness of the people in the room. And I was joking. I was like, man, it's really funny to see a lot of the people that I've been in this industry with for many years, like in their Sunday best. Like I was just like, oh, this is funny.

People are like showing up in their suits and in their like blowouts and their blazers. And I was like, oh, wow. Okay. This is a different vibe than like [15:50] I don't know, seeing you in Idlewild, California, like in the forest, like there's like a code switching that has happened, um, that I think is like appropriate and, uh, [16:00] an appropriate like maturing of the industry that's happened. And then like so many new faces of people who, yeah, are excited to be there and feel like genuinely interested and, um, [16:13] invested in what the future of [16:15] digital assets are going to look like.

Yeah. I had multiple people who I was meeting with just walk right past me and they're like, "I've never seen you in a suit before." Yeah. I don't know who you are, what's different about you. You've changed. Yeah, exactly. I was like, "Oh, we've all in a really healthy way, I think collectively sold out a little bit." And I'm like, "It feels kind of good, honestly, to be here." And be like, [16:38] I'm like, we're at like Javits Center. I was like, wow, this is a really different vibe. It's great.

You know, I mean, like, [16:44] We've... [16:45] pushed for so many years. I got into crypto in 2017. [16:49] And just seeing how it's progressed, all the things we were talking about with adoption and [16:55] And there's so many different ways adoption could go. Yeah. You know, we push for... [17:00] individuals, there's so many [17:02] ways it could go, but the institutional adoption, which is what you see at DAS, it's here. It's [17:11] We didn't know if that was going to happen for a very long time. And we're very much in the middle of it.

So it's all systems go right now. You know, it's great. Exciting. Anything surprising from yesterday or particularly interesting from either panels or conversations that you had? [17:27] Yeah, I mean... [17:29] I think, you know, I caught up with a lot of people that I've known for years and seen the kind of progression they've taken, whether it's. [17:35] in what they're building, what direction that they're headed, um, [17:39] And the surprising thing was like you mentioned the suits, but like everyone is kind of moving in this direction. Yeah. Right. Right. [17:46] Because as your audience changes and as it matures, whether you're building a protocol or a service or product, [17:54] you need to adapt to that.

And so it was a good surprise. Yeah. But just to see all of my old friends still here, still building, [18:03] Just with, you know, different clothes sometimes. Yeah, yeah, yeah, totally. Okay, so you got into crypto in 2017. [18:10] Tell us a little bit about your background and how you got into this industry and... [18:14] my background, um, [18:16] I started, I moved to New York 14 years ago as a speech pathologist. Oh, wow. Not crypto. [18:23] And I started building technology companies in healthcare and, [18:27] Around 2017, one of my good friends, we started just exploring crypto building companies.

[18:34] And, [18:35] you know, [18:36] There's this thing we saw in 2017 where it almost felt like it could be an inventor. [18:41] You could literally just write code and millions of people could access and you could build these incredibly complex, important tools. [18:49] And that sucked us in. And we just said, we want to build in this space. [18:54] And so over the next, you know, several years, we just... [18:57] Everyone has this resonant frequency. No matter what you want to do, you always just end up going towards something.

It's how you're wired. We always like working with people, with builders. My friend and I, who started the company, [19:11] We always just, we were fascinated by people. [19:14] startups building in crypto. [19:16] Just like the humans, the operations, the thing that keeps them up at three in the morning, like... [19:21] No matter what I wanted to do, I always just came back to wanting to fix that stuff. And it's why we got into token investing, which may sound like a boring thing, but if you're running a company, it's a very important thing.

[19:32] And for the last several years, you know, we've really pushed and [19:36] and develop these systems for these builders and, um, [19:39] Last year, we were acquired by Anchorage. [19:42] Congratulations. Thank you. Yeah, it was great. And we got the opportunity with Anchorage to do those [19:49] The same things we wanted to do, but just on a bigger scale with more resources and the incredible team at Anchorage just. [19:55] all of their weight pushing forward because, um, [19:58] they, as we found, you know, they're as obsessed with protocols as we were, probably even more, to be honest with you.

And to get to join that team and rise the opportunity of just working with builders, [20:11] in this new era that we talk about with TAS. It's been incredible. Okay. So that was Hedgie. You were running Hedgie, which was sort of like a Carta, [20:21] You can think of it as sort of like a Carta for on-chain teams. So token management, vesting, lockups. You have a thesis that we were talking about yesterday that token management is risk management. [20:32] Can you tell me a little bit more about that? [20:34] Yeah, I mean...

[20:35] Thank you. [20:36] you know, [20:37] So my co-founder, former co-founder, now he's at Anchorage on the protocols team. He was a treasury manager at WeWork for five years. His job was literally like risk management. [20:47] On a global scale. Uh-huh. [20:48] And he, you know, I ripped him off when I said that's his saying. He's the one who thinks the things I just get to say them. [20:55] But his whole kind of thesis has always been, [21:00] your job when you're running a company's risk management. And in crypto, [21:05] you have all the inherent risks of running a startup, right?

You have just running a startup is inherently risky. It's a high failure thing. You're pushing on the frontier of something new. [21:15] And then when you introduce what most companies in crypto are building, which are protocols, that's additional risk. You have to worry about that's a core product you're offering. [21:25] And so you're operating on these risky kind of endeavors, which are just part of the game. [21:30] But the thing you don't want to do is introduce risk you don't need to take, right? [21:36] You shouldn't do that. [21:37] And so when we talk about token management is risk management.

[21:42] It's about just offsetting risk as much as possible. [21:46] And it's why when we joined Anchorage, you know, the approach we took was how do we use Anchorage, by the way, which which we all know is a qualified custodian, one of many things that they are. They're more. [21:57] think of that as like a base and then a bunch of services wrapped around that focused on protocols, investors, everyone, right? But how could we leverage the qualified custody layer, the product that [22:10] secures your tokens and keeps them safe. How could we use that in token management so that [22:15] All these builders we love and we work with, they're not waking up at three in the morning.

[22:19] wondering if 40% of their supply is safe. How could we just take that off their plate? [22:25] And so when I say token management is risk management, that's what I mean. It's about not taking risks when you don't have to, the things that you don't have to take risks on. [22:34] That's nice. [22:36] Okay, this is kind of a question that's... [22:40] like a little bit of a tangent but one thing that they were talking about yesterday um at the conference was and i think i've i've [22:47] personally been seeing this in the industry is just like, sort of like the divorce between revenue and token price.

[22:54] And like how much they're, [22:58] Over the last, I don't know, let's call it. [23:00] especially around altcoins in the last year, like some of these companies are actually doing quite well and they are, [23:06] having very consistent revenue. Their businesses are actually more foundationally secure than they maybe were two years ago. But that doesn't seem to be like affecting the price of the token. And this kind of being like an industry wide phenomenon that's happening. And I think, [23:23] I, you have so much exposure, I feel like to many people.

[23:28] startups that have launch tokens, that are thinking about that. I'm curious if you have any thoughts about that. If you're seeing that as well, if that feels like a [23:36] a thesis that you agree with. [23:39] And if so, if you have thoughts around that. Yeah, I have thoughts. I don't know if they're good thoughts, but, you know, [23:45] I think if you look at crypto over the last six years, there's kind of... [23:48] a pattern you can see [23:50] Right now, I think we may be in a transitory state where how assets or prices changed.

If you look back [23:57] four or five years ago, perhaps. [23:59] there weren't as many tokens as there are now. There wasn't a fun or something where you could just produce tokens [24:05] a token and tokens are, [24:09] basically all fighting for attention and liquidity. Right. And so in the industry, um, [24:15] There are so many more assets fighting for attention. [24:18] Yeah. Right? Where... [24:19] you're kind of [24:21] core structure and everything you can say, like, say this token should be worth a lot more because it's a great business.

[24:28] We just haven't transitioned perhaps away from a speculative market that's just going off attention and vibes. [24:34] to one based on fundamentals. I will say it's what I like about the Digital Asset Summit, though, is that that's the institutional audience. Yeah. And they very much so care about fundamentals. [24:46] And so I think we may just be in a bit of like a paradigm shift at the moment. [24:51] I'm a terrible trader for one. So first, like, well, you, you're preaching to the choir on that one. So we buy high sell out.

So yeah, that's kind of our thesis. I'm the person if I ever talk about something, it's the sell signal. No, 100% same. So, you know, I'll just say like, I think how we price assets. [25:12] is changing. And I think the institutional audience does care about fundamentals and it might just take time to think about. [25:20] how the institutional audience works [25:23] gets exposure to those assets in a way where the fundamentals do matter. Yeah. So you think that the catalyst for when and why that would change is because there'll be some institutional recognition and adoption of those tokens that are around the businesses, the organizations that have strong businesses, strong business models?

Yeah, I do. I heard that a lot yesterday where people are looking at like, [25:46] business models. [25:47] Whether it's a protocol, you know, I mean, no, genuinely, I feel like that's also with startups. You know, if you look 15, 20 years ago, and Twitter, it was just about attention and getting people on and growth, right? Yeah. And then it very much shifted. [26:05] And I think we might be at that stage and that's healthy. Yeah, totally. Because at the end of the day, it's, it's, it's what you build and what value does it have to the world?

Right. Yeah. And I think. [26:17] Having that frame will ultimately drive, whether it's tokenomics or just core principles of what you're building, [26:25] to go towards that direction. [26:27] which I think is net positive for everything. Yeah. [26:31] Yeah, totally. Okay, a little pivot here, but AI agents. Oh, yeah. Is there any, what's the overlap between that space and treasury management or token management? [26:42] If any, nothing now, nothing now. It shouldn't be. I mean, I, I mess with Claude and, and my old Claude bought her open claw now. Yeah.

Um, um, [26:52] And, [26:53] it's magic when you play with these things, right? Yeah. You know, building with AI, autonomous agents, [27:00] But they like hallucinate. You can't trust them is the big thing. Yeah. And when I say token management is risk management. Totally. Having an AI agent manage your treasury is probably one of the riskiest things you can do now. [27:13] I don't know if that will always be the case. [27:17] But, you know, I do see... [27:20] Thank you. [27:20] agents playing a very important part in crypto right not in treasury management but just with the protocols like one of the things is i get to see everything that's like coming out right because i work with a lot of protocols as they're preparing to launch and then [27:34] I speak with them every week after they've launched and just see what, what everyone's building.

[27:39] And it's definitely taken the attention of crypto. [27:42] protocols that aren't building AI. They want to make sure these agents can get exposure to their protocols. And so there's just a certain set of tools and things you need to do for protocol management. [27:54] to allow agents to interact with what you're doing. And I see a lot of that happening now across the board. Interesting. Is like a kind of core thesis some people have is that agents will represent the majority of transactions. And if you think about it, it kind of makes sense going to Uniswap and clicking.

[28:12] Swap. [28:13] Versus having an agent that can do all that for you, but also 24-7 all the time, exactly how you want. [28:21] It's kind of what crypto was built for. Yeah. Anyways. So I think they're very complimentary. [28:26] But I think we have a lot of work to build on like, [28:28] Do I trust this agent with my retirement account? Do I trust it with my treasury? [28:33] I'll throw like a hundred bucks in a wallet and let it rip. [28:36] I expect all of it. [28:38] Go to zero.

Yeah. Just have fun. Yeah. But I would not trust it with a treasury. Yeah. [28:45] It'd be great if you could, but for now, I think there's a lot of things around like [28:50] wallet security, [28:52] just everything that you need to really build up. [28:55] Yeah. Yeah. OK, can we talk a little bit about some cap table red flags that you have seen? [29:01] Cap table red flags? Yeah. Like... [29:05] So this goes back maybe to like... [29:07] when I was at Hedgie and you're raising and things on your cap table.

I mean, [29:13] this is like a whole conversation. I'll come back for this one, but you know, I mean, if you're, I think when I speak with founders, everyone kind of knows the same thing. You want people on your cap table that you trust that have your best interests on, uh, at heart. And, [29:29] You know, the job of an investor is just to give you money, trust you and let you build something. Right. Right. [29:35] Um, [29:36] When you can get more than that, it's when an investor will actually be active.

[29:41] So I don't know if I have any like red flags. Like there's not like Lindsay's five things that are red flags for investors. But, you know, when you raise, you make mistakes of – [29:52] of [29:52] you are worried about the due diligence on you and you're not doing enough due diligence on, is this going to be a partner? I want to, [29:59] work with for the next three years. We weren't in that position. Luckily, we had great mentors, great investors from day one. [30:07] I've had lots of friends at their companies who they've, [30:10] spend way too much of their time dealing with [30:12] just unnecessary headaches.

Yeah. So you're, you have this interesting perspective, which you spoke to earlier about just being able to see across a lot of different teams that are launching across the industry. Yeah. What's the, [30:26] like vibe, appetite, [30:28] energy around launching tokens right now. [30:31] So busy. [30:32] Great. Really? It's insane. Wow. I was so busy this morning before I came in here. I was up to like one last night. [30:40] I feel like I've been like that for the last, like... [30:43] four weeks, 12 weeks. Yeah. I mean, Anchorage is in a very great position because they focus on protocols from like [30:50] a year before they launch, sometimes earlier to four years after.

[30:55] And one of the great parts of just [30:57] being on the token vesting teams. I just build product and talk to users. Anchorage, their whole system just [31:05] takes care of every part outside of that for these protocols. [31:09] But there are so many protocols launching, like... [31:12] Again, like when you go on Twitter or you go to like some conference and everyone's just down about it. Yeah. They don't see the like the inside baseball of like. [31:21] the actual energy companies. [31:23] And it's tremendous. It's, it's, [31:26] 10 minutes before I got here, I was just on calls helping people launch today.

After I leave here, I'm doing the same thing and I'm going to be doing that [31:34] You know, until my eyes fall out in a year from now. [31:37] I think it's a very... [31:40] good moment that we're in. That's such a fun job. It's awesome. I just talk to people and build stuff. Yeah. Do you have any [31:50] uh, particular products that you have had a really fun time working with or that you products that you, [31:56] personally use that you love? Yeah. A lot of them. I actually don't know which ones are public, so I don't know which ones I can say.

That makes sense. Yeah, totally. [32:04] first discretion. Um, [32:07] I'm very fortunate, though, because... [32:10] for the last four years that's all i've done is work with other builders yeah all i see and and [32:15] It's the thing I like the most. It's just seeing what other people are doing. I always give too much advice. I always give people product advice because I build products and jam with founders on this stuff. [32:27] Um, there are a lot of cool products coming out. [32:30] right now that are not just forks of something that existed three or four years ago.

I'm talking like new primitives, products that are very like cutting edge and frontier. Yes, institutional products. [32:43] Yes, privacy, which are the things we all know. [32:46] There's a lot of like... [32:48] I think we'll see a phase two of prediction markets. [32:52] We think of prediction markets as like Cal Sheet Poly market, but there are so many people building... [32:58] new things that are like the layers beyond that. I think, you know, six months we'll be talking about that. [33:05] Yeah, I mean... [33:07] It's all I do is like just see awesome things people build.

[33:11] and make sure I help them set up their token allocations for everyone. Okay, so institutional prediction markets. Did you sit in on the prediction market panel yesterday? I didn't. Okay. I'll talk about that later. Any hazards? Yeah. Hot takes? Yeah, what's up? I mean, it was – [33:30] It was interesting. I mean, I think that... [33:34] There were sort of like three, I think, like main takeaways from the panel. And it was a few investors who were investing in prediction markets. Um... [33:44] I think John Wang is his name.

He's like the Cal sheet crypto guy. Um, and then one other guy, I am not remembering who he was. Um, [33:52] So yeah, mantle on prediction market. But it was... [33:57] One thing they talked about was... [34:00] Basically, like, how... [34:03] uh, [34:04] about valuations of these prediction markets, like whether they're appropriate, whether they're just like inflated right now, and where there's like room. There's so much volume happening on these right now. Like where's there actual where's there actual room for them to continue to grow? And one of the things that was interesting to me was that like it's really regional right now.

It's very much like a few key countries that are actively using prediction markets and that there is an opportunity for, [34:32] other like smaller teams and smaller startups that are like in Brazil or, you know, in very specific regions to build for, you know, [34:42] their people, the things that that region cares about. And that's like untouched at this point. So that was one thing they talked about. And then let me see, I have some notes around it, because I felt like it was... [34:57] um, [34:58] Oh, they talked a lot about like, look, what are the moats right now?

And a big [35:03] thing was like liquidity and trust. And that like... [35:07] you, like, to bootstrap either of those things is, like, nearly impossible. So new players, like, how do they solve for that? And then... [35:17] starting with like a niche and like going really deep into one thing and, um, garnering like attention for that very specific thing. And then, and then building from there. And then the last thing that, um, [35:33] Thank you. [35:33] they talked about, which... [35:36] I have like mixed feelings on is that it's like, [35:39] Um, [35:40] prediction markets as reshaping what media and information and data and financial markets.

That's sort of how [35:49] Um, [35:51] these investors are justifying the valuation of at least Polymerkin and Kalshi at this point, is that it's not just a betting platform. It's new media or it's new social or it's shaping a geopolitical landscape. There's these really, really big stories that they can tell around what [36:08] they actually are, which I feel like... [36:12] Remains to be seen. Remains to be seen. Yeah. Yeah. So, but really interesting. And like... [36:20] A funny John Wang showed up in sweatpants, which I was just like, totally my dude.

I almost showed up in sweatpants today. Until I watched the video and realized you showed below the head. [36:33] So yeah, anyway, I was... [36:35] It was interesting to hear that. [36:37] A lot of the people on the panel felt there was a lot more room for new types of prediction markets where I don't know that I had that view going into that panel. [36:44] Yeah, I agree. I mean, I think, um, [36:48] you talk about like, um, [36:50] financial institutions having interest in them. And it's interesting because, [36:54] forever.

[36:55] You know, if someone says like the Fed's going to raise or cut rates, you would buy calls or puts and you'd basically be taking a position on an event. Right. With like options or something. [37:06] And with prediction markets in those spaces, it lets you actually go before the [37:11] buying calls or puts on the outcome of the event and actually, you know, [37:14] place speculation on the event itself. [37:17] So many ways like they're tied together and it's actually filling a gap. People were taking action on. [37:22] but there was no mechanism to take action on.

They could only take action on the outcome. And I think it's interesting when you put it in that perspective of it actually is an actual new financial instrument for many of these people. Interesting. Oh, one other thing that I thought was really interesting was, [37:37] Um, [37:38] that [37:40] Talking about... [37:42] bots and sort of like trading bots specifically, and that it doesn't seem yet that... [37:50] there has been an ability to, in like a mass way for people, [37:56] Individuals to... [37:57] to train their bots to arbitrage against both of the platforms.

And pretty unanimously, they were like, that day is coming. And that actually presents a much... [38:07] more opportunity that there will be like more trading volume, more platforms because basically building for that use case. And [38:16] Yeah, and sort of talked about how you saw that initially, not with bots, but just with user behavior. [38:22] doing that with like sports books when they first, when that like sports book apps first started, that was like such a big thing that so many people were [38:31] were doing. And so that was kind of interesting seeing that as an opportunity as opposed to [38:36] A feature, not a bug.

Like a cross-platform arbitrage? Yeah, exactly. [38:41] So many people talk about that on Twitter. Like you see, like, here's the script to do it. And the truth is anyone who's doing that is not talking about it. [38:50] Totally. Totally. If you figure that out, yeah, you're not telling anyone. For sure. So when I see all this stuff, I'm like, oh, I could be doing arbitrage on some random thing I don't know. And my claw bot goes schizo every like, you know, five minutes. [39:05] But in reality, people probably are pulling it off.

But they're just not talking. There's no incentive to. Okay, last question here. You have some thoughts on communities and DAOs and cap tables, I believe? I heard through the grapevine. Yeah, sure. I could talk about that. Okay, I'd love to hear. I feel like, I don't know, we have some scar tissue around the whole, the DAO of it all. Everyone does, yeah. Yeah, yeah, yeah, totally. What are the thoughts? [39:35] I could say that [39:37] you or the audience doesn't already know, right? I mean, we've all been through it. [39:41] Trauma bonded.

Trauma bonded, yeah. I think there's so much potential and you see a lot of the service providers for DAOs recently shutting down as well. [39:51] And I see... [39:54] DAO is still having a place for many protocols that are launching, but not just unanimously across the board. I think it's much more of a conscious decision now than... [40:03] you're launching a token, you're launching a DAO, which was definitely what it was. Everything's going to be a DAO, it's not the case. I think you are seeing companies launch more in the US.

[40:14] starting to come. Yeah. And launch without DAOs. And, you know, [40:19] Like the truth is like you don't need a Tao for everything. [40:22] Right? And I think a lot of star tissue comes from people launching DAOs when they didn't need to have a DAO. [40:29] It can be very useful though. Like I'm not saying... [40:32] DAOs are terrible for everything because they are actually very useful for a very specific thing. But when you just have a DAO and it's still like... [40:42] two people who were like, we're going to do this.

[40:46] The Dow is just either for show or it's just like... [40:50] I [40:50] a forum where people just, you know, doubt doubt chats, like maybe just go crazy in there. Right. Have you dealt with this? Yeah. Maybe really. Um, I also, uh, I do think though, what could be interesting is a doubt of agents like that. I'm like, yeah, okay. That does seem like it's autonomous in a way that our, our doubt certainly never was. So I could see a future where it totally has a new life. Um, [41:17] as a container for effort.

[41:20] for building value, but [41:23] Yeah, I don't. [41:24] It's just a decision-making construct, right? How are we going to make decisions? Yeah. [41:31] And the actual origin of doubt was just protocol level of you have this many people, this many assets, and they decide this, it happens. Yeah. But then it became... [41:40] People getting roles and elected. Yeah. [41:44] And that still has a place for some organizations, but not like it. [41:48] you know, was thought to be. Not in the way that we thought. Yeah. Lindsay, thank you so much for joining us.

Thank you so much. So nice to chat with you. Absolutely. See you later. See you later. [41:58] *cough* [41:59] Okay. [42:03] so fun really fun stuff man dow dow too dumb to dow i thought about that the other day first ever podcast episode too dumb to dow and it remains true i kind of want to like go back and give it a listen [42:17] Oh, you did. What was it like? It was fun. [42:22] Oh, we were so... [42:24] We knew so little. We weren't jaded yet. Oh, man. Okay. [42:31] So we're going to chat for a little bit.

You, me. [42:34] um [42:35] And okay, tell me what's going on with AI Love Island. Take care. Okay, AI Love Island. Okay, this is kind of a meaty story. There's many parts to it. [42:46] There's a lot of, it's got some legs. Okay. I'm going to begin. [42:53] Okay. Kate's giving me notes. Okay. I'm going to start by saying, [42:59] my first exposure to AI fruit. [43:02] Where were we again? I was on Twitter. [43:06] As one does. As all video. And it was... [43:11] The premise of the video is sort of like a hyper-sexualized [43:15] back and forth between a strawberry [43:18] who's leaving an eggplant's home, presumably post-cortical, and goes back to her partner who's another strawberry.

She gets pregnant. The male strawberry is very excited. They have the baby. [43:32] The fruit baby. Uh-huh. [43:34] It's a small eggplant. [43:36] he freaked out and sues yeah he's like and she's like i'll never do it again she's crying whatever it's this whole thing yeah and the quote tweet was like i can't remember exactly what it was but it was something along the lines of like the shit men send to each other in the group chat or something like that um and i was like [43:52] First of all, what is this slop?

And second of all, why am I watching it to the end? Like, I'm like, I need to know what happens between these strawberries. So that was my first exposure to it. Turns out there is, it's like a whole phenomenon that's happening around like what sort of looks like a... [44:10] like Pixar style, like Timu Pixar. Um, [44:16] that's like taking over Tik TOK and they're obviously AI generated, um, videos and, um, [44:24] Thank you. [44:25] We're going to play one. But wait, wait, let me just say what then developed... [44:29] you [44:30] is a whole series, Love Island Fruit, AI Fruit.

[44:35] So we'll say we'll say welcome to fruit love island where eight single fruits are about to flirt fights and trust things get messy fast. [44:44] Okay, this villa is insane. I'm not leaving here single. I just hope the guys are hot. [44:50] I'm here to have fun and probably break a few hearts. Rose said the quiet part out loud. I just hope the girls like nice guys. Okay, the banana guy is definitely my type. [44:59] Wait. [45:01] see or unable to see that it's [45:06] Hyper sexual fruit. [45:10] Looks maxing fruit in like scantily clad.

[45:16] Looks like some sort of beachy setting. The male fruit have their... The male... [45:22] presenting fruit have their shirts open um and the girls are in little outfits the girls are very like love if you've never seen love island and you've never seen any of these videos you can just skip this whole segment because it's it's not for you um [45:40] Yeah, and like millions and millions and millions and millions of views, like unprecedented. And so people are watching this. I mean, it's storytelling. It's storytelling, I think. So there was one account, I think it was called Fruity AI, that had the producers of the Love Island fruit thing.

I think it was like the fastest growing TikTok account. [46:01] to date and it has now since been removed from the platform i think there's been a cultural divide [46:09] of people. [46:10] Some people who are very, very upset by AI content, who are continuously reporting it, and... [46:18] obviously a bunch of people who are loving it and watching it. And it seems to be that there's platform, [46:24] Like, [46:25] um, drama around it. Um, so, uh, [46:29] uh [46:30] That's essentially the story. The newsletter After School by Casey Lewis is great.

And she did a little like excerpt about it that I highly recommend. And then also Zara Larson. [46:47] uh-huh started talking about it uh-huh people got really mad at her pop star Sarah Larson um [46:53] Why do people get mad? Because they were like, how could you be promoting AI content? Oh, she was pro. She was pro. She was into it. She was like, I'm watching my show. My show's on. And so, yeah, I think there's something about it that is... [47:07] We were talking about it before we began here.

And there's something like... [47:13] adjacent to like the anime porn stuff henty hentai hentai um [47:19] And, you know, [47:21] that like takes, like, [47:23] swaps platforms and like gains momentum on other platforms and then you kind of get like you get locked into the algorithm around it like if you watch one hentai thing then like i guess your whole feed becomes that yeah and it's similar where it's like it's hyper sexualized but it's not people and yeah [47:42] It also seems like it's somewhat of a Rorschach test or whatever, like that thing where you show people and it's like you can use the Rorschach test.

There it is. [47:55] You see it. You show people the Fruit Love Island. Yes. They're either going to react. I hate AI videos. This is slop or whoa. Like I need to watch everything. Yeah. Totally. Interesting. That's the story. Thanks for thanks for filling in anytime. Oh, there's one other element to it that the creator of I believe the Fruit AI, the original podcast. [48:18] one that got taken down, started posting really explicit, quite mean comments on, I believe, their Instagram. And I think the quote was... [48:31] Thank you. [48:31] We, we basically something along the lines of like, you guys aren't going to have any water left.

Like, [48:38] Saying like, I'm going to go so hard on creating these videos. So like the environmental impact of creating these videos was like brought into the conversation all of a sudden. And I was just like, where are we in the world right now? Anyway, on that note, actually, we could talk about the Sora shutdown news, which hit... [48:56] Yesterday, breaking news. Breaking. 36 hours later, breaking. Yeah, 48 hours later, Sora. So for those who don't know, Sora was OpenAI's [49:07] AI video generation platform slash social network is kind of how they were positioning it.

Mm-hmm. [49:14] You would use Sora presumably to make these videos that you're – Yeah, yeah. [49:19] I'm not making these videos. You're not making the videos. Fruity AI is making this video. Fruity AI would be perhaps using Sora, but maybe – It's usually Sora Larson. Or there's other ones, but it was a really big, splashy launch that OpenAI did when it first came out. [49:33] And they've really been pushing it. They, um, [49:37] had a big, huge investment from Disney, $1 billion. December 2025, that was announced, a three-year license. And basically the plan there was, hey, we are Disney.

We have all this incredible IP. We're going to license 200 of our most famous, iconic IP characters ever. [49:58] to uh sora so that you can generate all this stuff within sora make your own videos and that was that happened in december i remember when we covered it and it was a big deal everyone was freaking out um it's now march that deal is dead they were you can just do things you could just kill a billion dollar deal honestly that was that was news to me i didn't know that was possible um and disney was uh there's a quote somewhere that they were like [50:23] surprised, somewhat surprised by this announcement.

They were like... OpenAI was surprised or Disney was surprised? Disney was surprised. And basically what's going on or the speculation is that OpenAI is preparing for a Q4 IPO. [50:41] And they are really cutting some categories that aren't really working. Yeah, they're cutting some categories that aren't working and they're streamlining. They basically feel like.