I Started r/AI_Agents and Now I'm Launching a VC Fund

Show Notes

Yujian Tang started the r/AI_Agents subreddit in April 2023. For the first year, it barely moved. Then it hit 9,000 members, he went on vacation, came back to 36,000, and now it's approaching 300,000. In this episode, Yujian talks about how that community grew alongside his event business (Seattle Startup Summit, 900+ attendees last year), his two failed startups, and why he just filed paperwork to launch his own venture fund.

Conor and Yujian dig into the mechanics of starting a fund from scratch (Delaware PO boxes, EIN numbers, lawyers), why AI startup valuations have doubled in the last two years, whether a one-person unicorn is realistic, and what failed founders learn that successful ones sometimes miss.

Chapters:

(0:00) Cold Open: The Subreddit Growth Explosion

(0:21) Intro and Meet Yujian Tang

(1:06) From AI Research to Community Building

(7:26) Where AI Applications Are Headed

(10:03) The AI Bubble and a Valuation Reset

(10:39) Getting Deal Flow Through Community Events

(14:02) Filing the Fund: The Boring Side of VC

(16:04) How r/AI_Agents Went from Crickets to 300K

(18:39) Building an Accidental Empire

(26:37) What Two Failed Startups Taught Him

(29:52) Why Pre-Seed Valuations Are Out of Control

(37:37) The One-Person Unicorn Debate

(39:50) Seattle Startup Summit 2026

(42:17) What Chain of Thought Should Cover Next

(43:25) Outro

About the Guest:

Yujian Tang is the founder of Seattle Startup Summit, the largest startup event in the Pacific Northwest. He created the r/AI_Agents subreddit (now nearly 300K members), runs hackathons and developer events across Seattle and the Bay Area, and is launching an early-stage AI venture fund.

Guest Links:

Seattle Startup Summit: seattlestartupsummit.com

Reddit: reddit.com/r/AI_Agents

Show Links:

Chain of Thought Podcast: https://chainofthought.show

Newsletter: https://newsletter.chainofthought.show/LinkedIn: https://www.linkedin.com/in/conorbronsdon/X/Twitter: https://x.com/ConorBronsdon

Sponsor: Thanks to Galileo. Download their free 165-page guide to mastering multi-agent systems at galileo.ai/mastering-multi-agent-systems

What is Chain of Thought | AI Agents, Infrastructure & Engineering?

AI is reshaping infrastructure, strategy, and entire industries. Host Conor Bronsdon talks to the engineers, founders, and researchers building breakthrough AI systems about what it actually takes to ship AI in production, where the opportunities lie, and how leaders should think about the strategic bets ahead.

Chain of Thought translates technical depth into actionable insights for builders and decision-makers. New episodes bi-weekly.

Conor Bronsdon is an angel investor in AI and dev tools, Head of Technical Ecosystem at Modular, and previously led growth at AI startups Galileo and LinearB.

FINAL TRANSCRIPT
================
Speakers: Conor, Yuijan
Duration: 44:02
Total Words: 8878
Generated: 2026-03-10

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[0:00] Conor:
The first year, dude, like nothing like crickets. The next half of that year, we got another like 8000 people. And then I went to China on vacations and I came back and it was like 36000 people. And I was like, whoa. And then it like did it again in like another month. And I was like, oh, my God. OK, we got to implement some rules here.

[0:21] Conor:
Welcome back to Chain of Thought, everyone. I am your host, Connor Bronsdon, Head of Technical Ecosystem at Modular, and delighted to be back with you as a friend of mine is joining the podcast today. But first, I want to say thanks to our presenting sponsors, Galileo, for making this episode happen. And that friend is Yujin Tang. Yujin is well-known in the ecosystem, running some incredible events, building great content, tinkering. He's someone that, particularly if you're in the Pacific Northwest or the Bay Area, you may know if you were involved in AI. Eugene, great to see you.

[0:52] Yuijan:
Great to see you, Connor.

[0:54] Conor:
Why don't you tell our audience a bit more about yourself, since I know there are plenty of folks who know you from your work at Seattle Startup Summit and elsewhere, but I think it'd be great to give the audience some context before we dive into the meat of our discussion.

[1:06] Yuijan:
So now I run events and developer community and work on that stuff. But previously, I was a software engineer, so I come from a very technical background. I got into software engineering because I was originally doing AI research in the 2010s. you know, back then computer vision was kind of like the big thing and it was popular. So I did some computer vision research, I did some data research, and then I worked on some natural language processing as a company. I tried to build like a natural language processing startup at one point, but through that what I found was that I was pretty good at kind of like teaching people how to do AI, how to use AI stuff. And then I found that doing events was this kind of like interesting niche fun space where there weren't a lot of really good events that I saw. And so I started doing them and now I run the largest startup event in the Pacific Northwest, which is Seattle Startup Summit. And last year we had about 900 people and we're hoping to get maybe like, you know, 1,200 or 1,500 people this year.

[2:10] Conor:
It's super exciting. It was a great event last year. And it's really interesting for me as someone who's also actively having these conversations, just to see where you show up. I feel like everywhere I look, I'm like, oh, you should, you should know that person. You shouldn't have been there. Whether it's like, you know, throwing a hackathon in San Francisco or, oh, like you're, you know, you were involved in, you know, these researchers. Or, oh, look, like you're working on raising a fund, which we're going to talk about. Or like your dev advocate work at Zillow's previously to your guest lecturing at Stanford. You're kind of all over the place and just deeply embedded in the ecosystem. But I love this story of how you got involved, because I think it's a really important thing for people to understand contextually. And not everyone, I think, or not everyone thinks about how this process has happened, where it's gone from, you know, researchers are doing AI to more developers are doing AI to now there's this whole class of AI engineers. It's everywhere. And like, even now, I would say we're seeing this transition to individuals are being enabled by AI around the world where like everyone at my company is being encouraged to use co-work and cloud code, whether or not they're deeply technical. So I think this is happening all over the place now. And I'm kind of curious on your thoughts on where this wave is going, because there's so much there's so much hype involved in the space. And we've seen both sides of that. But there's also this perception of, oh, this is this is all a bubble that comes in. And I think anyone who's listening to the show probably knows, like, look, you know, there are some bubbling aspects and what's happening for sure. But this is a transformative technology that is going to change the way we work, in fact, has already changed the way we work. and has so many more impacts down the line. But you've kind of been here since the inception of the modern movement. What's your take on how things have evolved and where they're going?

[4:03] Yuijan: [OVERLAP]
Yeah, so I had just started research, you know, in like the late, like 2016 or something like that. And so I wasn't like, you know, building the CNNs back in like 2012 when AlexNet was coming out. But even so, in the last 10 years, like the evolution of Neural nets has been has been crazy. It's just been like, you know In in in 2016, you know, we're kind of at the space where it's all convolutional neural nets 2017 you have the attention is all you need the transformers paper, right? That was like super big came out. It was like super popular a lot of sightings and then Actually, one of my friends, I don't know if you met Yin Han last year but she is She was one of the authors, I think she was the first author on the Roberta paper, which was another like, you know, Transformer-like paper that came out of Meta. From basically, you know, 2017 to 2022, we were just kind of like building larger nets, and that's kind of like just pushing the scaling laws. And then, you know, I think now we've kind of gotten to the point, you know, when Chatscript came out, basically we were like, oh, like there really is like a switch somewhere that happens where the amount of parameters, the amount of data, and just the amount of compute that you have that goes into these models really starts to give you this feeling that you're talking to like a person. And I think, and I still see this, like, conversation, these conversations online, especially with like the whole, like, Clodbot, Moltbot,

[5:33] Conor: [OVERLAP]
Moltbot,

[5:34] Yuijan: [OVERLAP]
open...

[5:34] Conor: [OVERLAP]
whatever it's called now.

[5:36] Yuijan:
Yeah, yeah, that thing, like, there's a ton of people, like, talking about, like, oh, like, is this, like, Sentience? It's like, this is the chat you'll be seeing all over again. I don't want to get too into the metaphysics of, like, what is Sentience? So we'll skip that. But, like, you know, seeing all of this stuff really shows you that, the technology is definitely transformational. It's there. People, like you said, people are using it. It's transforming work. It's transforming the way that people live. And in some ways it's transforming the way that people live for the better. And in some ways it's transforming the way that people live for the worse. People are kind of getting into this thing where, you know, like they're like becoming codependent on the AI. And I would say that's probably worse for people. But then, you know, like if you think about when the internet came along, like, The internet also introduced new problems for people to kind of deal with, right? Like previously you probably couldn't get email phishing, right? That's a new thing. And now it's like, okay, now you're getting like AI bot scams, which is like a new problem, right? But then there's like the benefits of it. And so like the benefits you can kind of see are like, you know, the internet creates this connectivity. We wouldn't be able to be having this conversation as easily if it weren't for the internet.

[6:49] Conor:
Totally.

[6:51] Yuijan:
AI also helps you create like more, like it kind of like accelerates things that you would regularly do. And so some of these things are like, oh, like I want to edit something that I wrote. Like I would say, I would suggest that you probably shouldn't use AI to write your first drafts, but like, I know people do. And, oh, this is funny. I got an email recently where someone was like, oh, like blah blah blah this is my blah blah blah blah and then it was like if you want to schedule some time with me and then it was just like insert link and i was like oh yeah

[7:24] Conor: [OVERLAP]
Hmm,

[7:24] Yuijan: [OVERLAP]
okay totally

[7:25] Conor: [OVERLAP]
okay.

[7:26] Yuijan:
ai um so like there's i think there's there's this kind of like you know feeling that we we've gotten to a point where it's really started to get some applications right so the research is there the technology is there now it's like how do we apply this in a way that kind of is able to benefit people is able to to really um to really make lives better um and of course there's always the fear that you know like oh ai is taking your job because it makes it easier it makes it accelerated but it's like okay like it will probably just produce new jobs same thing with the internet right it just produces new jobs there's new things that you have to do Um and I also saw something that was like on Reddit recently that was like about uh um coding and it was just like oh like as a as a coder previously what I would have to do is I'd have to read the docs and I would have to you know read the the example code and then like debug and I would read the terminal output and now what I do is I read the docs. But of something else, I read a different set of docs and now I read a different set of output and I check that, oh, these lines are fine here. This is the diff between these two files. And it's like, okay, yeah, it's very similar still. It is just more advanced. It accelerates things. And I think, you know, over the past few years, we've had a ton of investments into, I guess what I would call infrastructure technology. In the 2018-2022

[8:59] Yuijan:
phase, we saw a ton of investment into MLOps. which basically once ChatsDB came about, it just quickly flipped the switch into LLM Ops. And now we've seen a lot of investment into this set of infrastructure tools, which I think, you know, some of these you can call Ops tools, some of these you can call Builder tools, some of these you can call whatever it is that you want to call them, it's like things that makes building AI easier. And we've seen a ton of investment in that. We've seen a ton of spend. I just made a post on LinkedIn recently, and it was like, oh, like this spending on AI from this time last year is up like 44%, which is a lot. And it's like a bubble, you know, it does feel like a bubble. And if you remember in 2000, we had the dot com crash, which felt like it was like the bubble for the internet and it's still here. It's still around. It's clearly grown since then. And I, I would not be surprised. I'm not going to say that we are going to see something like that, but I would not be surprised if we saw something like that.

[10:01] Conor:
Totally.

[10:02] Yuijan:
Yeah.

[10:03] Conor:
At least we're going to see some companies fail at a minimum, right? Like not every AI company is going to be a massive success, despite some of the valuations we're seeing. Is it going to be systemic? I mean, I think there's arguments for there being risk, but it doesn't mean that technology is going to wipe out. It means that we're going to see a bit of a reset of valuations.

[10:22] Yuijan:
And I would love to see that, especially as an early stage investor.

[10:27] Conor:
Yeah, so tell me about this investment side of things. I know you have been getting more deeply involved in AI investing in particular the last year or two. What's happening on that front and what are you seeing?

[10:39] Yuijan:
Yeah. So one of the things about having a community and about building a community, I think is, okay, so there's multiple sides to it, but let's like simplify it in the sense that you'll need some sort of funding. you'll need a set of people who kind of are all interested in similar technology or similar topic. In this case, it'll be a technology. And you need to find a way to give back to this community. And so one of the things that I really enjoyed about my community work was And this came as a total accident was getting early stage founders to come in like demo and pitch. So I held this event and I did the classic, you know, tech event talk style. You have a few panels, a few speakers, usually their sponsors, and then, you know, you have them speak. But one time, This one company sponsored, it's a big AI company, so I'm not going to say who they are, but they sponsored my event and then they didn't show up. And so I was like, well, we have this like 30 minute slot that if we have like, you know, a few people who want to come and demo. And so I just basically went up to the stage and was like, is anybody brave enough to come do a live demo of their tool? And this was like something that people really loved. Like people came up to me after and they were like, hey, that was cool. I would love to do that next time. I just wasn't ready this time. And I was like, oh, wait, maybe we could just have this as a recurring session. And so like I played around with it a little bit and then we just started adding it as like a recurring thing to the events that we do. And, um. I put up a form that was basically like, if you want to demo and you've raised only a small amount of money, like this is for you. Like, this is the way we give back to the community. Like we, we give these builders a way to showcase what they're building before, you know, they go in and raise like 10, 20, $30 million and whatever. And so then we, we had companies like WordWare, which, you know, was super popular in 2024, uh, that, you know, eventually they raised a $30 million round a few months later. And then, um, we had some, Really new like open source projects like assistant UI Which now just raised like a 4.5 million dollar seed round So we saw a lot of these projects coming by and at first it was just like okay, you know You're just giving builders like a way to show off what they're doing But then I kind of looked back like towards like the middle of last year in like 2025 and I was like, huh? a lot of these companies are actually like going on and like raising rounds and like, you know, the valuations are going up. And some of these people, like I've known from like very early stages. And so I'm like, maybe I should get into investing. So last year I put some money into Aperture Capital, which is a

[13:17] Yuijan: [OVERLAP]
VC firm run by Don Shu, who's a guy at the Python Software Foundation. I think he's like a fellow or something. He's like someone who's important in there. And then Enrico, and I can't remember Enrico's last name, but he's managed like billions of dollars before. And so these guys were doing investment for a while. I've known Don since like 2021. And I was like, hey, I'm interested in investing. I'm going to put some money into your next fund. And then I thought, oh, wait a second. So there was like a couple of things here, but I thought, oh, wait a second. What if I raise the fund because, you know, like these guys will invest in whatever it is that they're investing in, but I could also invest in specifically the.

[13:58] Conor: [OVERLAP]
Right. You're getting deal flow. You're seeing these early deals. You can do this directly.

[14:02] Yuijan: [OVERLAP]
Exactly. I'm seeing the early deals. I'm getting deal flow. So I was like, I can invest in some of these companies. And so, um, I talked to some investors and they told me about how they got started. And I was like, well, it sounds like it's hard, but Hey, you know what? We'll give it a go. And so, uh, I, you know, started the formation. We actually like just filed the formation. I was hoping to file them in January, but things kind of like, I had to like find a, um, This is like things that people don't tell you about are like, Oh, like in order to do this, you have to get like a lawyer to basically file things for you. And because you can't file, I mean, you can file it yourself, but it's like, it's a, it's,

[14:35] Conor: [OVERLAP]
It's

[14:36] Yuijan: [OVERLAP]
it's a real

[14:36] Conor: [OVERLAP]
not

[14:36] Yuijan: [OVERLAP]
hassle.

[14:36] Conor: [OVERLAP]
going to go well. Yeah.

[14:37] Yuijan: [OVERLAP]
Yeah. Yeah. It's a real hassle. You have to have. So typically venture funds will have three instates. They'll have an LLC, a GP and an LP. And so what we did was we were like, we're not going to take any, um, You need management fees. And so we'll just have a GP and an LP. And then you need to get an EIN for both. You need to set up a bank account for both and you need addresses. And I was like, well, I don't, I'm not going to use my house as an address.

[15:00] Conor: [OVERLAP]
Got to get a PO box or something.

[15:02] Yuijan:
We get a PO box in Delaware. Uh, so, you know, then I did, I went through and did all these things. And so now it's like, okay, we could finally file and raise money and stuff.

[15:11] Conor:
Okay. I'm curious now, did you have to fly to Delaware or did you use a service that is just forwarding?

[15:17] Yuijan: [OVERLAP]
No, so, um, I found out about this thing called, uh, stable and, uh, it's like, um, Stripe recommended it to me. So I use, I use Stripe for, for, you know, taking credit cards. And so,

[15:28] Conor: [OVERLAP]
I mean, of course. Yeah.

[15:29] Yuijan:
yeah. And so, so this was like recommended by Stripe. And so I was like, okay, let's check it out. And it's like, I think it's like $50 a month, like something like that. So I was like, okay, we'll try it out, you know?

[15:41] Conor:
I, as an aside, I absolutely love that Stripe has their percent of global GDP running on Stripe, uh, on the main screen of their webpage now, like right here on the homepage. It's like, Oh, as of today, early February, it's 1.56%. Like, God, what an ambitious company.

[16:01] Yuijan:
That's pretty amazing. Yeah. I love that.

[16:04] Conor:
I love this journey. Like you obviously have been deeply involved in the community for a while. I mean, like we're talking about events here, but you've been, I think you, you started the RAI agent subreddit.

[16:15] Yuijan:
Yeah, yeah I started the AI underscore agent subreddit and I specified there's an underscore because there's multiple AI agent subreddits now. But I started this subreddit back in like April of 2023 because I was at Zillis and I was working on RAG and after like doing like some work on RAG I was like dude this is important like there's a really not like okay there's a lot to RAG if you get really deeply into it but like you know There's not that much to it. There's not that much to it. And I was like, and then, um, auto GBT was this project that was like super popular at the time. And nobody knew like really what to call it either. And then like, I heard somebody like float this idea of this thing called agents. And I was like, huh. I bet this would be cool. Let's build a community around that. And so I made, I just made the subreddit and it was like AI agents. And I did like the things you would normally do to build communities online. You know, you have like a weekly thread. We had project displays. We had questions. I think we're going to add hiring this year because there's been a bunch of people who are posting like hiring like posts on the subreddit. And I'm kind of like, I

[17:19] Conor: [OVERLAP]
You

[17:19] Yuijan: [OVERLAP]
don't really

[17:20] Conor: [OVERLAP]
want to

[17:20] Yuijan: [OVERLAP]
want

[17:20] Conor: [OVERLAP]
consolidate,

[17:20] Yuijan: [OVERLAP]
separate

[17:20] Conor: [OVERLAP]
yeah.

[17:21] Yuijan: [OVERLAP]
posts. Like let's just put it all into one thread. But anyway, like I saw this in 2023 and I was like, yeah, let's do it the first year dude like nothing like crickets like a Thousand people joined and it was mostly like it started off like it started off just me telling people like hey You guys should check out the subreddit and people would join and so for a year that worked get us up to a thousand And then the next half of that year, we got another like 8,000 people. So it started growing. And then like in like December of 2024, we were at like 9,000. I was like, well, this is super cool. I remember I posted this meme, like the over 9,000, like, you know, Dragon Ball Z meme about this. And then, um, And then I went to China on vacation. So I went to go see my wife's family. And I came back and it was like 36,000 people. And I was like, whoa, that was a lot. That was really fast. And then it like did it again in like another month. And I was like, oh, my God. OK, we got to implement some rules here, because at that point you start getting spam. You start getting

[18:20] Conor: [OVERLAP]
Right.

[18:20] Yuijan: [OVERLAP]
like people being like, here's this perplexity plan. And then here's this NSFW chat GPT thing. And I was like, all right, we got to like we got to figure out a way to deal with this. Um, so yeah, but that was, it was, it was like a really weird thing. And now it's at like almost 300,000 people. Um, maybe like 2. I think it was like 2.5 million views last one.

[18:39] Conor:
It's so interesting talking about this because from the outside looking in, it feels like this could be this very intentional plan where it's like, yeah, you should build these like digital communities and then started doing a bunch of in-person events and leverage that to create content, and then he still builds on the side, and then he adds investing to really lean in. But knowing you and talking about it, I'm like, no, you really love this stuff. You are fascinated by AI. You love building community. You love talking to people. And you're just kind of pursuing your passion seemingly. And then you kind of go, oh, I could add this to like with the investing piece to your point where you're like, yeah, if I was really thinking about this two years ago, maybe I invest in a couple of earlier companies, but also like, no, I just wanted to like feature these builders. I'm just excited by it.

[19:31] Yuijan: [OVERLAP]
Yeah, yeah, I think if you talk to a lot of people who are in this space, a lot of it is accidental. I saw this TED talk way back when I was like, I don't know, like 16 or something like that, that was just like, oh, here's these startups, here's this stuff that we've done with these startups and blah, blah, blah. And they're like, the most crucial factor is timing. And so for me, I honestly, After, um, after, so I failed at building like two different startups at this point. Right. So one was like this, like social media, like a survey type app that was just like really dumb. And then there was like the natural language processing API, which was much more interesting when I was talking, which, which, what I did, but, um, Once ChaiGBD came out, I knew that was going to fail. And so I was like, all right, you know what? We're going to work in some startups. I'm going to go figure out what these people are doing and learn from these startup founders. But I think the timing was just really good in the sense that as I was doing this, more and more people wanted to be involved and more and more people kept getting into the space. And also, It is really just something that I just enjoy doing. Part of it is that I enjoy doing it. I spend a lot of time doing things that are boring now, like sending emails, reading emails, reading legal

[20:52] Conor: [OVERLAP]
You

[20:52] Yuijan: [OVERLAP]
docs.

[20:52] Conor: [OVERLAP]
don't have an AI agent for that yet? Come on, Rand.

[20:54] Yuijan: [OVERLAP]
I don't have an AI agent for reading emails. Sending emails, I actually have tried this. So actually I tried this and then my domain got blocked to spam. And so I was like, we'll figure this out later. Like as for now, like I'll just do it manually. And then I actually, you know what? I just don't trust agents for reading legal docs, you know?

[21:15] Conor: [OVERLAP]
Oh, yeah. No, I think there are certain things where you need to have

[21:18] Yuijan: [OVERLAP]
I'm like,

[21:18] Conor: [OVERLAP]
more

[21:18] Yuijan: [OVERLAP]
I

[21:18] Conor: [OVERLAP]
control.

[21:18] Yuijan: [OVERLAP]
want to read this doc. I want to know what it says. Um,

[21:21] Conor: [OVERLAP]
Yeah.

[21:23] Yuijan: [OVERLAP]
but, uh, what was I saying? Oh yeah. So it was just like, you know, it's just something that I enjoy doing and then kind of compounds and you just figure out like if it's going to work or not. And I talked to someone about this recently and, and, uh, they were like, how do you, like, how do you do it? Like, how do you, how do you do all these events? And like, you know, how are you doing all this community stuff? I was like, dude, I don't, I don't really know. Like sometimes I'm just doing things and then, um, Sometimes I do things because I know there's a lot of people counting on me to do it. The Seattle startup summit is actually like, it's a lot of work. It's way more work than I had hoped that it would be, as a lot of these things are. But I was like, at this point, I have too many people that are counting on me to do this. I can't just like not do it. And so it's like, okay, you have to like, sometimes it's like, you know, you get into doing things and sometimes it's part of it is like, you get to do these because you like it. Sometimes you get to do these, you continue doing it because people are counting on you and you kind of like, are like, okay, like, let's make it work, you know? And then the investment thing was like really more of like a, Hey, like, I think there's this opportunity here. I don't even know if I'm going to be good at investing. Like, dude, like, I don't, I don't know. But I think I've talked to enough VCs that my opinion is really like, it seems like most of these people don't know if they're going to be good at investing either. Right.

[22:41] Conor: [OVERLAP]
It takes a while to figure it out, yeah.

[22:43] Yuijan:
And so it's like, ah, well, it seems like nobody really knows. So give it a try.

[22:48] Conor: [OVERLAP]
I like it. I will recommend a couple of helpful assistance that I've enjoyed as far as email here. Quora.computer has a really solid summarization to help you kind of just get through your inbox faster. I enjoyed that quite a bit, though I admit I'm not currently using it on my work email and probably ought to set it back up again. And then I'll shout out a startup that I invested in from YC last year, Iris, which is doing summarization of emails and calendar work and it's been fairly helpful. Though I think it's a little better on iPhone than Android for the moment.

[23:28] Yuijan: [OVERLAP]
This is what they call a value-add investor.

[23:31] Conor:
I do what I can. Yeah, I have to. I have to be a somewhat value add.

[24:18] Conor:
I think investments you want to shout out here now that we're all the time.

[24:22] Yuijan: [OVERLAP]
Um, no, all of my, all of my current investments are currently under contract. So I can't, I basically,

[24:27] Conor: [OVERLAP]
Okay. Okay.

[24:28] Yuijan: [OVERLAP]
I basically was like, I was like, here are 10 companies I want to invest in. Now I need to raise money now. And at the same time about that, I need to raise the money to be able to invest in these companies. I need to get them to send me these contracts so I can sign these contracts and get them.

[24:41] Conor: [OVERLAP]
Yeah.

[24:41] Yuijan: [OVERLAP]
Ready. And then I have to wait until they're ready to announce before I can even say, Oh, I invest in this company. Which honestly, these are things that you don't think about as an investor. You think like, Oh, I just wire this money into this company and suddenly I own part of this. And it's like, no, that's not how it works at all. There's

[24:56] Conor: [OVERLAP]
Yeah.

[24:56] Yuijan:
actually a lot of docs. And I was like, dude, I, I signed up to be, I signed up to read docs. That's what I signed up for.

[25:04] Conor:
You're like, I want to do the cool part of this. I wanted to like talk to companies be like, yeah, your stuff is cool. Let me help you get, let me give you some money. And now you're like, wait, I just read legal documents all day.

[25:13] Yuijan:
Yes, it's been a lot of time really reading legal docs. It's like, uh, um, I do want to shout out something here. Uh, the r slash AI agents does have a weekly project thread, which gets, you know, at first it was getting like one or two projects a week. Now it gets a lot of projects. I get notifications about this at least like two or three a day that they're, you know, people are posting, I think usually ends up with more than 10 projects.

[25:38] Conor:
I saw that Sterling Chin posted Marvin on there recently and

[25:44] Yuijan: [OVERLAP]
Yes.

[25:44] Conor: [OVERLAP]
got quite a few

[25:45] Yuijan: [OVERLAP]
I talked

[25:45] Conor: [OVERLAP]
likes.

[25:45] Yuijan: [OVERLAP]
to him about that, dude. I talked to him about that last Friday and I was like, dude, are you going to turn this into a startup? And he was like, he was like, I got to check the IP. And I was like, all right, let me know. Cause like, I'm, I'm interested.

[25:57] Conor: [OVERLAP]
It

[25:57] Yuijan: [OVERLAP]
It's,

[25:57] Conor: [OVERLAP]
seems interesting.

[25:58] Yuijan:
it's, it's, it's got good traction. Like it's, it seems like it's pretty new. It's like something that he's kind of like, and this is the right way to do a startup, right? It's like you build something that you kind of like, you get your friends on it and they like it. You know, you get your coworkers on it, they like it. And then now it's like this open source thing that has, you know, a few hundred stars and it's actually getting popular. And I was like, this is how you build an open source startup. So hopefully it does turn into something like that. That would be really

[26:24] Conor:
I actually want to go back to something you said earlier about basically being a failed founder. Because I'll say as someone who has failed once at founding, I've only given it a try once to be clear, so 0 for 1.

[26:37] Yuijan:
cool.

[26:37] Conor:
So let's just be very clear, no successes. It was a huge learning opportunity for me. Like I learned so much about like what I'm good at, what I'm bad at, where my gaps are, what what it kind of takes to go next. And similar to you, I think I then went off and was like, OK, let me go work for some startups and maybe I'll try this again down the line. Uh, you have done that and now you've kind of come out the other end of that and have started to build an events company. You've started to build an investment business. What are the things you learned as like an early founder that you have now adjusted in your, your day to day today, particularly as we're starting to automate so much with AI, I'm kind of curious about that workflow and that change for you.

[27:22] Yuijan:
Yeah. So I think when I founded my first company, I was very, very good at building software. So like I, because I run a lot of hackathons, I get a lot of questions about people who are like, how do you become a software engineer? Especially like, you know, like people who are earlier stage or who have, you know, seniors in college or like, you know, masters or whatever. And I'm like, I can't help you because I had the weirdest career, like, I started as a software engineer when I was 16 because I won some international competitions. And then I was really good at doing this. I was good at building software. I went to school. I was good at doing research. And I was just a very vertically skilled person. And then when I went to start my first company, the first thing I learned was nobody cares how good your software is if they don't know what your software is.

[28:13] Conor: [OVERLAP]
Mm.

[28:14] Yuijan: [OVERLAP]
And that was number one. And I was like, OK. I guess we'll go learn how to do marketing. And so I learned how to do social media marketing. And what that really meant was that I learned that you should post on social media. And that was about the extent of what I learned from that. Number two was like, you have to go do sales at some point. You have some money, you have to go do sales at some point. I actually talked to quite a few VCs. So I think one of the nice, one of the interesting and like success, one of the interesting points and successes that came out of failing my first startup was that I learned how to cold email, maybe not like how to cold email well, but I learned how to do it, which was like, you

[28:53] Conor: [OVERLAP]
Psychologically,

[28:53] Yuijan: [OVERLAP]
don't,

[28:54] Conor:
it's hard.

[28:55] Yuijan:
it is, it's hard to do. It's even harder to send warm emails sometimes to people you know. And so it's just like, it's just like, okay, like you have to, you just have to send this email to this person. And I ended up getting to meet some VCs here in the Seattle area. And I learned from them basically, like about what a startup is versus like what like a business is. And in the sense that they were like, look, no one's going to invest in you unless they think you're going to make a hundred million dollars a year. And I think with the AI automation thing, that number is going to go up. People are going to expect more.

[29:29] Conor:
I'm already seeing it.

[29:30] Yuijan:
Until the bubble pops. I think I, you know, the, once, once valuations go down again, people will be like, Oh, you know, actually these are like businesses in this, at the end of the day, they are businesses and they do have this kind of scale with the available, you know, real like GDP thing. So

[29:49] Conor:
So, so to your point here, and I'm going to sidetrack us briefly, but.

[29:52] Yuijan:
yeah.

[29:52] Conor:
You know, I think most people listening here know that if you're investing at like an early stage, you are looking for a hundred X outcomes. Like even if a business starts to return you two X on your money, that doesn't really help you that much in the grand scale scheme of the fund, because 90% or more of your businesses are going to fail that you invest in. And so the startup investor, like you need those outsized outcomes. You're really relying on them. It's why it can feel so odd for folks who are used to like bootstrapping a business, but you're like, I'm making money. Like, why would you not invest in me? And a VC is going to say, well, I don't see the upside. And so it's just, it's just not worth my capital. I need that higher opportunity. Um. But to your point, we've seen a major change in valuations lately. So I make an easy example here is like a Bay Area startup that was joining YC a few years back might've come out of it valued at about 10 million for its pre-seed round. And now it's 20 million is typical. So, and there, there are higher valuations than that too. Uh, obviously there's some variants, but like there's been a, it's doubled, uh, if not more sometimes. So we've seen this crazy valuation rise, which means, okay, if I want a hundred X, I don't just need a billion dollar outcome. I need a $2 billion outcome. And that starts to get really challenging as you point out, because yeah, there are some AI native companies that can pull a cursor and have these like insane outcomes, but most companies are not cursor.

[31:11] Yuijan:
Right. Yeah.

[31:15] Yuijan: [OVERLAP]
Yeah. Yeah. I don't know what's going to happen with this because there's this, I mean, like, you know, just on the investment side, like you talk to a lot of VCs and people are like, why are all of these pre-seed companies have such crazy valuations? And even like for like my own like fund, like there are some like there are some companies that I want to invest in that I'm just going to invest in because I know the founders and I like want to get it on the round. And it's like it's a series A round there at one hundred and fifty million, two hundred million dollar valuation. It's like, OK, like So at that point, I'm like, does this thing, is this thing going to 10x? Is this thing going to 20x? That's all I think about. But also like, I'm not a classical VC. I'm only, I have a tiny fund. I can be a little flexible on like what I do because you know, it's not like I'm managing $750 million that I have to turn into like, you know, like $3 billion or whatever.

[32:05] Conor: [OVERLAP]
Give

[32:05] Yuijan: [OVERLAP]
Yeah.

[32:05] Conor: [OVERLAP]
it 10 years. I'm curious to see your fun sides 10 years here.

[32:07] Yuijan: [OVERLAP]
We'll see, we'll see what it looks like in 10 years. Like, you know, it's a year one fun one. You just kind of like, you're like, okay, let's, let's test the waters. Let's get into these companies, you know, get some, get some traction and things like that. But this helped me like this, you know, when I first started out talking to these VCs helped me kind of see what VCs see and then see from what startups see. And that is kind of like, that's part of like the reason why, like I shut down the first company was like, because a, I was just burning money. I didn't know what I was doing. I couldn't get any sales and I couldn't raise money. So then I was like, okay, well, what if we do something that is actually venture scalable? And that's how I got into this NLP API. Cause I was like, well, I have a lot of credibility in this space and I know how to build APIs and I know this makes money. And actually, like you were saying earlier, it's like as an entrepreneur, you kind of think like, oh, this is making money. Like why won't people invest? That was actually a very good reason is because ChatGPT was out. So it was a really good idea that nobody invested in that because if they had invested in it, it was just lost money. Anyway, like doing this kind of stuff, like really taught me how to do like the marketing, the sales, and then like doing events really teaches you how to do operations.

[33:13] Conor:
you

[33:15] Yuijan:
And then at some point, a lot of it was just about working with people. It's like knowing the right people, And part of it is about liking people and being able to talk to people. I was always kind of an extroverted person. As a software engineer, I was very extroverted for software engineers. And so for me, that part has been not too hard. It's been easier. But even so, it's still kind of hard, because I think building a business, being an entrepreneur, and I'll kind of talk about this from this perspective of founders versus, let's say, S&B entrepreneurs, which is kind of where I'm at right now. Um, I think like in this space, I have a lot more like flexibility. I have, it's a much more broader role in the sense that like, you know, I'm going to be doing, uh, operations, manage, uh, management, marketing, sales, building the deck tech behind the scenes. I use, uh, I use Gemini to write all my code. Um, I used to use Claude,

[34:12] Conor: [OVERLAP]
Okay,

[34:12] Yuijan: [OVERLAP]
um,

[34:13] Conor:
interesting, yeah.

[34:14] Yuijan:
and I switched to Gemini and I'd been on Gemini for a while. So I use Gemini, um, and I

[34:19] Conor: [OVERLAP]
Did

[34:19] Yuijan: [OVERLAP]
use

[34:19] Conor: [OVERLAP]
Gemini 3 get you to switch or what was the switch for

[34:21] Yuijan: [OVERLAP]
No,

[34:21] Conor: [OVERLAP]
you?

[34:21] Yuijan: [OVERLAP]
2.5.

[34:22] Conor:
Oh, interesting, okay, alright.

[34:24] Yuijan:
Yeah. Oh, 2.5 pro is actually quite good.

[34:26] Conor:
Yeah.

[34:27] Yuijan: [OVERLAP]
Um, I found that, uh, actually even 2.5 flashes is quite good for writing front end code because you know, like, to be honest, it's not a lot of, I mean, okay, to be honest, the websites I'm building don't require a lot of complexity. So it's like 2.5 flash is even good enough, but I usually

[34:41] Conor: [OVERLAP]
And

[34:42] Yuijan: [OVERLAP]
use.

[34:42] Conor: [OVERLAP]
it's much cheaper than Anthropic.

[34:44] Yuijan:
Yeah, it's much cheaper. Yeah. But I usually use Pro. And then, you know, I'm just doing all of these different things. And then I think as a startup founder, It's, I have a lot of flexibility in how I scale. Like I don't have to hire anyone. I don't have the money to do it anyway. But even if I did, it's like, you know, like I don't have to do it. I don't have to scale. I'm not under pressure to be like, I need a $10 million business tomorrow. You know, but as a startup founder, when you go as a startup founder and you raise money to do, to do a startup. You raise that money with the intention of, OK, I'm going to raise this money. I'm going to hire two engineers. I'm going to hire a marketer. And next year we're going to go and we're going to we're going to like, you know, be a 10 million AR business in 24 months, you know, something like that. And so as a startup founder, you have to have like the flexibility to and the ability to kind of like let go eventually as you scale. And I think like that is actually a different skill set. And it's a very, very challenging skill set to do well, because, and I'm sure you've seen it, right?

[35:51] Yuijan:
Founders are really good at getting things off the ground. But the moment you have like 200 people in your, up until like 5,200 people, like your founders are pretty much always going to be your best bet on any leaders for your organization. Beyond that, that's where you see like, is the founder able to evolve and keep up with the business? And so investing early stage is always interesting because you're kind of, you're betting on the founder. And you're also betting on the idea that the founder will know when it's time to be like, okay, I have to evolve. I have to like step this up. Um, so yeah, there's just like, uh, these two are different things that require a lot of different skills. And, um,

[36:33] Yuijan:
yeah, I

[36:34] Conor: [OVERLAP]
No,

[36:34] Yuijan: [OVERLAP]
don't

[36:34] Conor: [OVERLAP]
I totally

[36:35] Yuijan: [OVERLAP]
have

[36:35] Conor: [OVERLAP]
agree

[36:35] Yuijan: [OVERLAP]
any.

[36:35] Conor:
with that. I've talked to the co-founders of DevRev about this, Dheeraj Pandey and Manoj Agarwal. And Manoj was on the podcast last year and Dheeraj I interviewed on Dev Interrupted a couple years back. And they both talked about this where it's like, Yeah, as you get off the ground, like you can control a lot. But what's what they pitched is basically their biggest predictor of success was getting other team members to buy in at a founder like level and scaling leadership. Because as you get to that larger org size, you just can't do it all yourself. You have to have enabled a crew of people around you with founder like qualities, with leadership qualities who can help grow the org. And even with the scaling of AI tools and that enabling certain people to 10x their output, whether that's creating more 10x engineers, whether that's more marketing collateral, whatever it is, you still need to scale that team. It's really hard to get to venture scale without broadening your team.

[37:37] Yuijan: [OVERLAP]
Yeah, I always think like, you know, there's a lot of talk around the one person unicorn right

[37:46] Conor: [OVERLAP]
We're not there

[37:46] Yuijan: [OVERLAP]
now.

[37:46] Conor:
yet, in my opinion.

[37:48] Yuijan:
It might happen, but if you are that one person unicorn, like whoever that is gonna be doing that, like that person has to have some incredibly good and an incredibly wide skill set. And it's

[38:00] Conor: [OVERLAP]
Yes.

[38:00] Yuijan: [OVERLAP]
just,

[38:00] Conor: [OVERLAP]
It's

[38:01] Yuijan: [OVERLAP]
I think maybe we'll see like a 10 person unicorn, maybe like a 20 person unicorn, something like that. But one is like, I'm like, I don't know about that one dude.

[38:11] Conor: [OVERLAP]
hard to do. Yeah.

[38:12] Yuijan: [OVERLAP]
Yeah, yeah, yeah. And to be honest, I think also like at the end of the day, AI is an enablement tool. And I'm not sure I want AI to be super autonomous, like truly, truly autonomous, because it's a little bit scary. But maybe it will happen, maybe it won't. I don't know. When I was younger, I always thought the singularity would be an interesting thing. We all plug our minds into a core and upload ourselves onto the web or something like that. But as I've gotten older, I've been more of the opinion that actually, Uh, a lot of these things just require people and a lot of the problems, a lot of the problems and scaling businesses. And maybe this is a effect of my like community work, but like a lot of these problems is just like, do you have the right people in place? Um, and I, I'm not going to name any names, but I see companies that I, I talked to, I talked to the founders and they're like incredible. And then I see who they hire and I see what they're doing. And I'm like, I don't know if that was the right pick.

[39:18] Conor:
Not every founder is great at hiring and you need to be if you're going to scale past a certain point.

[39:24] Yuijan:
Yeah. Yeah. Yeah. At the end of the day, I still think a lot of it is, I mean, you know, even with the acceleration of AI, the acceleration abilities of AI, I think a lot of it is like a people thing.

[39:35] Conor:
Yeah. And speaking of people, if you want to get the skills to be an incredible founder or you want to meet the next company that you should join, maybe check out Eugene's Seattle Startup Summit coming up here in a couple of months.

[39:48] Yuijan: [OVERLAP]
Yes.

[39:48] Conor: [OVERLAP]
And I'll let him pitch that himself.

[39:50] Yuijan:
Yes, yes, yes. If you're a tech leader and you are interested in keeping up with innovative technology, or if you're a startup founder and you're interested in basically talking to tech leaders who are going to be your buyers, you should come to Seattle Startup Summit. This is like last year, we had 467 unique companies there. We had 900 people there. This year, I'm expecting that number to basically like, you know, almost double. And, you know, we've we've got basically all the big companies and big investors here in the Pacific Northwest. You know, Madrona, Anthos, Ascend, Fuse, like all of the big VCs you can kind of think of up here, which is not a lot. But, you know, like they're there, they're there here. And we have some people coming from the Bay as well and some people from New York and some billion dollar funds that are that are coming in. They're looking for companies to invest in. They're looking for companies to invest in. And also the tech, the tech people here, like there, there's a ton of enterprises. And I think, so I think Seattle actually has one interesting advantage over the Bay, which is that there are actually a bunch of these like huge enterprises out here. And you can just like, like these people are around, like they live in the area. You can kind of like, they'll, they'll come to the events. You can get to know them. Like, you know, like I've met multiple people who are like directors of engineering at like companies like, Intel, or Coupang, or Expedia, or Booking.com, or whatever. And these are the companies that are more likely to buy your product than Google or AWS. Not that Google or AWS won't buy your company or your product, but like these people are much more

[41:26] Conor: [OVERLAP]
They

[41:26] Yuijan: [OVERLAP]
likely

[41:26] Conor: [OVERLAP]
might

[41:26] Yuijan: [OVERLAP]
to.

[41:26] Conor: [OVERLAP]
be more likely to buy your company. That's your point.

[41:28] Yuijan: [OVERLAP]
They

[41:28] Conor: [OVERLAP]
Yeah.

[41:28] Yuijan:
are much more likely to buy your company. This is very fair. Google, Meta, they're much more likely to just be like, I want to buy your company. So yeah, I think that's one unique advantage for Seattle is the B2B enterprise space, which is why all the VCs up here fund the B2B enterprise companies.

[41:45] Conor: [OVERLAP]
And

[41:45] Yuijan: [OVERLAP]
But yeah,

[41:46] Conor: [OVERLAP]
you

[41:46] Yuijan: [OVERLAP]
that's

[41:46] Conor: [OVERLAP]
can

[41:46] Yuijan: [OVERLAP]
what I

[41:46] Conor: [OVERLAP]
find

[41:46] Yuijan: [OVERLAP]
did.

[41:46] Conor:
all the info on that at seattlestartupsummit.com, which we'll of course link in the show notes here as well. Youshin, it's been so much fun catching up with you. I'd love to kind of close with a question for you about what the topics or people are that you think we should be exploring on the show. Like if you were to write the content plan or make suggestions on it for us, What should we be covering? Who should we be talking to?

[42:17] Yuijan:
Let's see, Chain of Thought is the title of your show. It seems you talk to a lot of people who are in tech leadership positions and founders and things like that. I think, you know, that's probably the most interesting audience if you're trying to kind of like get into covering more of like the AI file leadership stuff. And I think maybe something that would be interesting to do, if not, I mean, and probably also quite difficult, is getting interviews with exited founders. It may not be too hard to get interviews with people who are like recently exited. But, you know, like people who exited not just in the sense of like, oh, my company IPO'd, but also exited and like, oh, my company got acquired. So like, I think these people have a unique view on the current landscape. And so I think they would be interested to have on.

[43:13] Conor:
That's a great idea. Uh, Eugene, thank you so much. Really appreciate you taking the time to chat today. It's been a ton of fun as always. And, uh, can't wait for sale startup summit.

[43:23] Yuijan:
Yeah, thanks Connor, I'll see you there.

[43:25] Conor:
And if you are listening and you enjoyed this conversation, remember to leave a rating or review on your podcasting app of choice. If you're on Apple podcast, we particularly appreciate a short little review. Uh, or if you didn't like it, you can reach out to me personally on LinkedIn or elsewhere and tell me what you want to see, uh, because we are responsive to our fans. Uh, so thank you so much for listening, everyone. We appreciate you and we'll see you next week.

[43:51] Yuijan:
Alright, thanks Howard.