Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Uh, you've been in the game for a long time. Can you tell me the story of your first investment ever?
A Yeah. Um, our box group is named after our first investment. Uh, so, uh, it's like a combination. So the first investment's a company called boxy. Uh, it was a, uh, Roku competitor. Um, uh, we were in their seed round as a adorable check. Um, I didn't want to write my name as an angel investor. So I created an LLC called box group to invest in boxy. Which made me feel bigger. Uh, the box was like a cool nightclub in the city at the time. It felt like a cool word. Uh, I've looked with Aaron Levy. Uh, he registered box.net like two months before I did box group, which I'm bitter about. So at some point he'll sue me and it's all over.
AI assessment note: “So the first investment's a company called boxy. Uh, it was a, uh, Roku competitor.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Chatbots. Yeah. Wait, yeah, what, uh, wasn't there, this was sort of before my time, but there was a whole chatbot era, right? Wasn't there, like, pre-AI was like, it was supposed to be the thing. It was sort of right. It was just didn't have the, the underlying tech trend. Is that right?
A I feel like the tech wasn't there, but also the branding of chat bot to, uh, chat GPT isn't that different, um, but magically different from a outcome and, uh, sort of adoption curve. If you look like the automated chat bots, I think is what they were called for that moment in time. Uh, they all fell on their face because They weren't interesting enough, good enough. They were like pre-programmed answers. And then, uh, open AI releases in essence, just an advanced version of that in many ways from a consumer positioning. Uh, and here we are. And so you are like, the idea of chatbot was right in how you're interacting with the tech. The tech, uh, to your point, just wasn't good enough.
AI assessment note: “The tech, uh, to your point, just wasn't good enough.”
Redirected raw tape
D 2 · C 4 · P 4 · Cm 4 3.40
Q what you're seeing on the LP side, but we've heard that there might be some fatigue from LPs on what's going on in venture, but at the same time, it feels like that David Goggins meme where, you know, venture just keeps on chugging no matter what, uh, you're going to the AGM. Uh, what, what are you seeing broadly in terms of LP appetite for ever bigger venture funds?
A We're a small, adorable seed fund based in New York city. So I, we are not, we are not responsible to answer that question. I think our, like your job, if you take LP capital is to give them back a lot of money one day. And I think if you haven't, um, you, you owe that to them. And so at some point the patients should run out. And I, I appreciate that. I think the challenge is the, Time for liquidity in early stage venture has gotten pushed significantly from where it was more predictable a decade or two decades ago. You could say seven to 10 years on an early stage fund and mean it. Today, I think you say seven to 10 years, and you're like, by that, I mean, like, 12 to 15. And that, that's a substantial difference. And I think you need to align with your investors on what that timeline is, because it's in a rational timeline. Like, The people we fund, if you go back 15 years, they were, like, pre-elementary school for the most part, right? Like, if you look at the young founder that you're investing in today, a fifteen-year timeline is two-thirds of a life. Like, it's an irrational number, and so these, like, the go-in motion of making an investment to the return the fund to LP's timeline is so decoupled from, I think, a psychological standpoint that, um, your stakeholders are just Dramatically, uh, unrelatable.
AI assessment note: “We're a small, adorable seed fund... we are not responsible to answer that question.”
Partly raw tape
D 3 · C 4 · P 3 · Cm 3 3.30
Q to like go try a startup and then maybe I'll invest later. Uh, and obviously the Teal Fellowship is kind of like a scaled version of that, but there's a lot of other, you know, initiatives. Uh, how has that changed your strategy? Has it changed your strategy at all? Uh, and kind of like, What, what does the early stage market look for you look like for you today?
A I think they're like, there's always been these splashes of noise. Um, and Very, very little, like, if you go back again, I'm old, and so I've been doing this through these microwaves of, uh, change in the early stage market, um, very few products stay where they are. They move in different directions. They either get later. So if you think about new entrances as funds into the early stage market, most of the ambition is to become a bigger fund, and in doing so, you Become later by nature of scaling, uh, your business. And I think on a product side, uh, you're only as good as the product you're offering. And so what has been amazing to me about YC is they've just continued to compound quality of the satisfaction to their customer. They are, they are not free, right? You're giving YC equity. And yet if you look at like the happiness factor, the, the MPS or whatever, uh, cheesy acronym you, you call reviews, but like, People go to YC because other people who went to YC loved it, and they think it was entirely worth it. And so I think the products that get invented need to live up to the cost. And if the cost is free, like nothing is really free. And so what comes with that freedom? Is that attaching to a brand? And if you attach your company to a brand, is that a good thing to have done? Or is there some negative, uh, externality that comes with that? And so I think Um, and it's …
AI assessment note: “there's always been these splashes of noise... very few products stay where they are”
Partly raw tape
D 3 · C 3 · P 3 · Cm 3 3.00
Q them as like a YC company, right? Uh, and it found, it seemed like that the story of Airbnb was like, COVID was a transformational moment for them, and they emerged like a stronger company than ever. Um, Do you expect that to happen to any startups, uh, maybe in your portfolio or just out there in the market that are getting beat up but might emerge stronger than ever?
A So, so like if you isolate tariffs, that has a sure impact on a subset of companies, various side of software in many ways. Um, I think there's software companies that involve logistics and shipping that definitely, uh, are impacted, but I don't know that the, like come out of the tariff, uh, is a predictable framework. Like, what does that actually mean? Do we get to free trade in reality? Do we get to some equilibrium? Is this China? Only that we're talking about, and I think within there lies a very hard to foresee, again, point of stability, whereas at least in COVID, if you said we return to a normal world, that was a more predictable endpoint. Um, if you assume, you know, early in COVID, it was wait two weeks, and then the world will start again, and then it was some longer period, but I think there was an appreciation for what coming out of it, Could look like. Whereas I think right now you're in like the creation period. Harder to, to guess. Um, yeah. You know, the, the easy guess is like American manufacturing windfall, but that feels Like a big stretch, like no one's building a factory overnight. I feel like that happens in other parts of the world, not here.
AI assessment note: “I don't know that the, like come out of the tariff, uh, is a predictable framework.”
Not addressed raw tape
D 2 · C 3 · P 3 · Cm 3 2.70
Q Um, no, no, no. I, I, I, I was more, um, how was, has there ever, you know, it feels like over the last two years, call it, there's been more of these sort of roll-ups than ever before. Was there, was there another, did, was there another kind of like general, like market-wide crack, or was it just sort of like individual areas, um, and opportunities versus broader trends?
A I struggle to think that the way to build companies is to replicate Another company that's succeeding. In these moments, what you tend to have is one winner and a bunch of followers that don't win. And so can there be a single version of a roll up? If you look at Android, they're great at acquisitions. That's a different phrasing of the word roll up. Roll up is either we're going to buy a bunch of things that are the same size or we're going to buy like one big thing and then tuck in some other smaller things around it. So I think unpacking the nuance In these words is more important than assuming a general like success across a wide variety of companies. I think the like moment in time where you probably saw fast followers or fast movers win was in the on-demand business, right? When Uber trained the world that you could touch something on your phone and something in the real world would happen, it unlocked like a A behavior across the world that was very different, right? And that was this phone to real world connection that I think opened up a ton of other businesses. I don't think they all worked, but I do think that that was a horizontal opening versus a business model innovation that has been used in other industries or financial industries and then applied in venture.
AI assessment note: “unpacking the nuance In these words is more important than assuming a general”
