Straight Answers
An LLM assessed 938 question → answer exchanges, the host's own answers included. Speaker names were hidden during assessment. Each exchange was marked answered, partly, redirected or not addressed, with a quote as its source. Every exchange below is timestamped and plays. How it works →
These readings are observational: the transcript shows whether the question was answered directly, whatever the reason. It is an AI reading of a public exchange, never a claim about intent, and the tape is one tap away on every row. full disclaimer →
Every one of the 195 people on the record is accounted for: 5 carry a full rate (8 or more assessed questions on raw tape), 171 more have their questions counted (16 of them with at least one not answered directly; too few raw questions for a fair percentage, edited feed included), and the remaining 19 never took a direct question in any tape we hold: compilations, panels and cameo appearances leave nothing to assess.
None identified
All 4 people who answered every question put to them, ranked by how many they took, so the ones with the most assessed questions come first. highest rate none identified small samples
| Person | Not answered directly (%) | Redirected + not addressed | Questions | Argument clarity /5 |
|---|---|---|---|---|
| Michael Shemelis DX Engineer, Convex | 0% | 0 | 10 | 4.2 |
| James Dickerson Founder & CEO, Boring Group | 0% | 0 | 9 | 4.2 |
| Roberto Nickson Founder, Eluna AI | 0% | 0 | 9 | 4.2 |
| Theo Tabah Co-founder & COO, Late Checkout | 0% | 0 | 8 | 4.2 |
The moments, on tape
The question Greg asked, then the AI assessment note from the answer. Tap to play the moment. Not addressed = the question was not engaged; redirected = acknowledged, then steered elsewhere.
“How long did that take you from start to finish?”
answered: “So, uh, it was lunchtime here in SF. By the way, you know, what's funny”
“And going back to, you know, acquiring newsletters, you obviously have a lot of experience in this space. How do you go about, you know, thinking about a framework for what's the right price for a newsletter?”
answered: “the approach here is like, I always talk about this idea of the hub”
“Um, Harley, I'm curious, like, how, how important do you think that is to some of the entrepreneurs that you see in terms of, you know, having a safe spot? Is that, is that key to success?”
answered: “So we're going to jump around timelines a little bit here”
“I'm not saying it's bad. I'm just saying, why is everything purple?”
answered: “I don't know, man, but I don't like it. I don't like it”
“What do you, what advice do you have for, for people who want to get into physical books, but you know, it's hard for them to, to focus and they don't have, you know, it sounds like this is, you have an innate ability and you just kind of love these books. Like what advice do you have for people who aren't born with this?”
answered: “I don't, I don't know because like, I, I didn't understand”
“You have, you have 48 hours to make a million dollars. How do you do it?”
answered: “I'm going to challenge the prompt a little because I'm like”
“But the question is plastic bags. How much is that really impacting climate change?”
answered: “The thing with data and the scientific studies is it depends who you ask.”
“I'm looking to grow it to 500,000 subscribers within the next four months. What would you do if it was me?”
answered: “I'm actually more careful now than I used to be about giving straight up advice.”
“And I've, I've heard you actually talk about religion before on other podcasts. You know, I know you're a student of religion, but could you talk a little bit about maybe some similarities that you see with what you're building at rite of passage and interestingly enough, how religion is structured?”
answered: “So I'm just going to go on the religious tangent of why I think”
“Because, you know, ultimately as a business owner, you care about the, You know, moving up in the rankings, right? So you, you don't want to, like, have a loop just for the loop's sake.”
answered: “even if you do try this experiment and it doesn't work, you haven't necessarily lost anything”
“Which is a startup idea in itself. Like why doesn't, right?”
answered: “for many reasons, which we don't need to get into. But I want to talk”
“Do you think, uh, you'll be using lovable in 12 months from now?”
answered: “until these integrations get solidified, I haven't gone like end to end”
“Hey, it looks like you have a Q-tip in your ear, stuff like that. And the question is, What could have Apple done to lean into that, to sell more AirPods?”
answered: “What you just said reminds me of what Elon does with the Tesla.”
“Cause you're like, you couldn't, couldn't you use this technology to do that? And in, in which case the outcome is like a high, more retentive student.”
answered: “what I'm trying to get at is a lot of bad tutoring is the actual, the relationship”
“Where do you think the, the tea space is going? Cause I know you are involved in a tea company and, and next time, well, you're, you can come back on the show anytime you want, but the next time we need to be drinking tea.”
answered: “this is not me trying to, you know, Promote fire belly, but”
“Um, what was your big rejection? What, uh, what, what, what kind of cemented that realization for you?”
answered: “I can tell a lot of stories about how like I've gotten rejected”
“And it was a business show and You know, in terms of viewership, it didn't have a huge viewership, but it had a super high value viewership. So the idea here is what are other high value audiences that need live shows?”
answered: “What I'm trying to do is I'm trying to take all of this inspiration”
“So Google stitch is another one. Like, can you show us how we can, how we can go from, you know, MD file plus HTML to creating something?”
answered: “getting the MD file, but also focusing on the design aspect.”
“Fair request. Is that something you've said before?”
answered: “Um, yeah, so I've been doing this a lot. Well, usually you should get an error.”
“Which is kind of what my friend Joe is doing with Mixi, right? Because like he knows that people want to share these mixes.”
answered: “one thing maybe we could touch on briefly is just the algorithmic feeds of today”
“And how, how big of a business do you think you can create? You know, I, I see like the traffic and the, and the, and the opportunity and the traffic, but like from a revenue perspective, how big do you think it can get?”
answered: “a couple of ideas I've had with Guilty Chef, I think the obvious ones”
“I mean, I'm not surprised, but, um, yeah, what's your take on that? Like, is there an opportunity before you get into your ideas and before we like start cooking, basically, is there an opportunity to create apps that are like not AI or do you have to come up with an AI app idea for TikTok?”
answered: “I believe that we're currently just scratching the surface of new, uh, application functionality”
“It's this thesis that, you know, people are generally bad at accomplishing their goals, but if they have someone who holds them accountable, they're more likely to do it. So for example, would people be willing to pay for accountability around working out?”
answered: “This kind of thing is going to be a huge category... but there's problems.”
“Are you a media guy now? Is that how you describe yourself?”
answered: “My entire life was always the combination of two things.”
“He uses Instagram in a really smart way where he always draws it back to the newsletter. I wonder if James Clear, like, was he really passionate about atomic habits or did he see the opportunity to build this ecosystem?”
answered: “and I, you know, I've learned from that and do, like, a similar thing.”
“Let's talk about that for 1:02. What would, If Naval was designing, you know, a high school or something, what would, what would it be like?”
answered: “I think it's like focus on math, basically. [...] I've been thinking about this actually with AI.”
“Like I, it's hard to identify like what is actually unique Data. Because all they need to do is gobble up a big enough sample size to have it be predictable in almost any arena.”
answered: “I want to talk about a few things... So the Cal AI example”
“You can't do it all. So how do you decide?”
answered: “I only go on Twitter while I'm drinking coffee. I call it the coffee framework.”
“Do you think, uh, you'll be using lovable in 12 months from now?”
answered: “I like these tools to quickly MVP myself... So now I'm going to say”
“It's like, what if we can get to that level? What was the unlock of our creativity?”
answered: “There's an opportunity to use something like this and basically do client work”
“Um, and so I'm, I'm curious just for your guys' perspectives on that. Like, have you found in general that overthinking results from inaction?”
answered: “when you think about zero to one consumer social, it's probably 90% art”
Percentages come from raw unedited recordings only: produced podcast audio has tangents and stumbles cut in the edit, which moves the speaker up by about 12 percentile points. The small-sample counts include the produced feed. This is a reading of a transcript. It is not an accusation of dishonesty, and there are many good reasons not to answer a question directly (confidential numbers, unreleased products, someone else's news to break).