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 5 5.00
Q Let me ask you this. A lot of people might be hearing like, oh, chat GPT. It's like, like, why do you need marketing? It's like the most magical thing in the history of the world. Like how much value does anything add to making it as successful? Can you just talk about just like the value that a marketing person adds to a product like that? That's already incredible.
A Yeah. When you think about all of the different stages of the funnel, awareness was clearly not the problem that ChatGPT or OpenAI had. Everyone knew of ChatGPT, but when you clicked one zoom level further, the thing that came up was, I don't know what to use it for. Like, I don't know what it replaces. Like, should I be using search for this? Should I be using ChatGPT for this? Or how can it even help me? And so the work of marketing ended up becoming Creating this sort of use case epiphany where people could say, I had no idea Chatsheet BT could do that. And yeah, maybe I should be using it for XYZ reason in my own life. And so I think you have to be very diagnostic in terms of what can marketing be doing to help rather than just going off of the typical top of funnel and then middle of funnel and conversion oriented tactics that end up being a playbook.
AI assessment note: “the work of marketing ended up becoming Creating this sort of use case epiphany”
Answered raw tape
D 5 · C 5 · P 5 · Cm 5 5.00
Q Can you speak more about what this looks like? Say a startup wants to start implementing something like this.
A Two simple processes that you could put into place today is one set up a forum called marketing review. This can be an live meeting that you host for an hour a week, or it can be a Slack channel where people are posting things async, or even an email alias where things get sent to. Have that be transparent to the rest of the organization. So anyone in the marketing team, anyone in the product organization can join that forum. What that does is it creates a fishbowl where you see sort of What are the themes that come out when somebody reviews a piece of content? Is it, are they looking at the strategy? Are they looking at the audience? Are they looking at the words? Are they looking at the sort of design approach? So you learn through osmosis of looking at, at some of these discussions. And then I would say don't overdo it. I would say there are probably two checkpoints in a program that are really important to get aligned at. One is the 20% review. A 20% review is a strategy review. What are we trying to accomplish? Who are we trying to do it for? And what is the rough approach that we're going to take? If everyone feels comfortable with that, you come back at the 80% mark where you've done a lot of the work on the artifacts, the different types of teams that have to be involved, and how do you take something to market in the first place? And the reason that I say 80% is sort o…
AI assessment note: “Two simple processes that you could put into place today is one set up a forum”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q amazing guests, all these super successful people on the podcast, all these stories of epic wins and nothing but success, and I think in reality that's not the case, and it's important for people to hear that things aren't always up and to the right and always win-win-win. Is there a story from your career you can share where things didn't work out and what you learned from that experience?
A And again, this question's hard because there's so many things to choose from as, as potential examples here. And you're absolutely right, Lenny, in that like most careers are not the sort of linear journeys that are reflected on somebody's LinkedIn profile. Now I'll talk about a fantastic success, which is called Stripe Relay, which you probably, I'm just kidding because nobody remembers it. It was ahead of its market. We launched it back in 2014. It was supposed to be The platform with which e-commerce companies would tap into social commerce, you know, the buy buttons, if you, if you remember that, and It launched to a lot of fanfare, but then eventually failed. Like it didn't produce the sort of revenue or the numbers that we had expected. And the understanding here was that as, as much as one side of the marketplace, or you might have some conviction that you need to put something into the market for a particular moment in time, the timing of the market really matters. And the timing of multiple parties coming together to make a platform work really matters. And so the learning here was like, we hadn't gone deep enough into the market dynamics. We hadn't done enough user research. Did people really want this? And if they did, what were their alternatives? What was the stacks that they were operating in and would they adopt a net new tool versus one that integrated into exi…
AI assessment note: “I'll talk about a fantastic success, which is called Stripe Relay... A clear flop”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Can you speak more about what this looks like? Say a startup wants to start implementing something like this.
A Two simple processes that you could put into place today is one set up a forum called marketing review. This can be an live meeting that you host for an hour a week, or it can be a Slack channel where people are posting things async, or even an email alias where things get sent to. Have that be transparent to the rest of the organization. So anyone in the marketing team, anyone in the product organization can join that forum. What that does is it creates a fishbowl where you see sort of What are the themes that come out when somebody reviews a piece of content? Is it, are they looking at the strategy? Are they looking at the audience? Are they looking at the words? Are they looking at the sort of design approach? So you learn through osmosis of looking at, at some of these discussions. And then I would say don't overdo it. I would say there are probably two checkpoints in a program that are really important to get aligned at. One is the 20% review. A 20% review is a strategy review. What are we trying to accomplish? Who are we trying to do it for? And what is the rough approach that we're going to take? If everyone feels comfortable with that, you come back at the 80% mark where you've done a lot of the work on the artifacts, the different types of teams that have to be involved, and how do you take something to market in the first place? And the reason that I say 80% is sort o…
AI assessment note: “Two simple processes that you could put into place today is one set up a forum”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q amazing guests, all these super successful people on the podcast, all these stories of epic wins and nothing but success, and I think in reality that's not the case, and it's important for people to hear that things aren't always up and to the right and always win-win-win. Is there a story from your career you can share where things didn't work out and what you learned from that experience?
A And again, this question's hard because there's so many things to choose from as, as potential examples here. And you're absolutely right, Lenny, in that like most careers are not the sort of linear journeys that are reflected on somebody's LinkedIn profile. Now I'll talk about a fantastic success, which is called Stripe Relay, which you probably, I'm just kidding because nobody remembers it. It was ahead of its market. We launched it back in 2014. It was supposed to be The platform with which e-commerce companies would tap into social commerce, you know, the buy buttons, if you, if you remember that, and It launched to a lot of fanfare, but then eventually failed. Like it didn't produce the sort of revenue or the numbers that we had expected. And the understanding here was that as, as much as one side of the marketplace, or you might have some conviction that you need to put something into the market for a particular moment in time, the timing of the market really matters. And the timing of multiple parties coming together to make a platform work really matters. And so the learning here was like, we hadn't gone deep enough into the market dynamics. We hadn't done enough user research. Did people really want this? And if they did, what were their alternatives? What was the stacks that they were operating in and would they adopt a net new tool versus one that integrated into exi…
AI assessment note: “Stripe Relay... It launched to a lot of fanfare, but then eventually failed.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Beautiful. Okay. We got a new framework. Cut off the presses. I love it. Date. Okay. So with differentiation, what's your thoughts on being, saying you're just a lot better or a lot cheaper?
A Being cheaper is a race to the bottom, especially when you think about, um, sort of scaling laws and how things are playing out. Every company is sort of becoming an AI company at this time. And so as models get cheaper, more capable, being cheaper is not going to be the thing that really is a durable approach in the market. And I think in terms of doing things differently, it's not just for the sake of it. I think it's, it's really that novelty and that differentiation is something that people are craving for. They're not looking for yet another tool in the market. They are looking for something that aligns with their values, aligns with what their goals are. And so if you can be really crisp on understanding the user need, understanding what is the problem space in which they're operating, I think that kind of one, two punch of a fantastic product experience, and then the marketing experience to match can be a superpower for your company.
AI assessment note: “Being cheaper is a race to the bottom”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q the furthest edge of where AI is going, and so it's just such an interesting place to study. So let me ask you this, just like, as a person working there, what are, what's like something people may not know that's a Like a wonderful positive element of how OpenAI works. That's just like, oh, that's super interesting. And then what's, what was maybe a challenge of working at OpenAI?
A A surprising thing that surprised me at the company was just the warmth and intellectual curiosity of my peers and leaders at the company and truly the sort of Commitment to the mission of making artificial intelligence that benefits all of humanity was not just lip service. It was something that was embodied day to day. The sort of questioning that happened, the sort of pressure testing that happened, the rigor with which products were developed, go to market strategies were developed was bar none. And so that's something that I really admire and it was a privilege to be a part of that organization. I think challenging, of course, is just being at the eye of the storm, right? The eye of the eye of the hurricane. And so all eyes are on OpenAI at all times. And I think that is a good thing because of the ramifications of the product, but it also really raised the stakes in terms of how we operated and with what scrutiny, everything that we did was looked at with.
AI assessment note: “A surprising thing that surprised me at the company was just the warmth”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Beautiful. Okay. We got a new framework. Cut off the presses. I love it. Date. Okay. So with differentiation, what's your thoughts on being, saying you're just a lot better or a lot cheaper?
A Being cheaper is a race to the bottom, especially when you think about, um, sort of scaling laws and how things are playing out. Every company is sort of becoming an AI company at this time. And so as models get cheaper, more capable, being cheaper is not going to be the thing that really is a durable approach in the market. And I think in terms of doing things differently, it's not just for the sake of it. I think it's, it's really that novelty and that differentiation is something that people are craving for. They're not looking for yet another tool in the market. They are looking for something that aligns with their values, aligns with what their goals are. And so if you can be really crisp on understanding the user need, understanding what is the problem space in which they're operating, I think that kind of one, two punch of a fantastic product experience, and then the marketing experience to match can be a superpower for your company.
AI assessment note: “Being cheaper is a race to the bottom”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Let me ask you this. A lot of people might be hearing like, oh, chat GPT. It's like, like, why do you need marketing? It's like the most magical thing in the history of the world. Like how much value does anything add to making it as successful? Can you just talk about just like the value that a marketing person adds to a product like that? That's already incredible.
A Yeah. When you think about all of the different stages of the funnel, awareness was clearly not the problem that ChatGPT or OpenAI had. Everyone knew of ChatGPT, but when you clicked one zoom level further, the thing that came up was, I don't know what to use it for. Like, I don't know what it replaces. Like, should I be using search for this? Should I be using ChatGPT for this? Or how can it even help me? And so the work of marketing ended up becoming Creating this sort of use case epiphany where people could say, I had no idea Chatsheet BT could do that. And yeah, maybe I should be using it for XYZ reason in my own life. And so I think you have to be very diagnostic in terms of what can marketing be doing to help rather than just going off of the typical top of funnel and then middle of funnel and conversion oriented tactics that end up being a playbook.
AI assessment note: “the work of marketing ended up becoming Creating this sort of use case epiphany”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q the furthest edge of where AI is going, and so it's just such an interesting place to study. So let me ask you this, just like, as a person working there, what are, what's like something people may not know that's a Like a wonderful positive element of how OpenAI works. That's just like, oh, that's super interesting. And then what's, what was maybe a challenge of working at OpenAI?
A A surprising thing that surprised me at the company was just the warmth and intellectual curiosity of my peers and leaders at the company and truly the sort of Commitment to the mission of making artificial intelligence that benefits all of humanity was not just lip service. It was something that was embodied day to day. The sort of questioning that happened, the sort of pressure testing that happened, the rigor with which products were developed, go to market strategies were developed was bar none. And so that's something that I really admire and it was a privilege to be a part of that organization. I think challenging, of course, is just being at the eye of the storm, right? The eye of the eye of the hurricane. And so all eyes are on OpenAI at all times. And I think that is a good thing because of the ramifications of the product, but it also really raised the stakes in terms of how we operated and with what scrutiny, everything that we did was looked at with.
AI assessment note: “I think challenging, of course, is just being at the eye of the storm”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q issue with people just starting earlier in their career where they just, like, never learn how to do the thing, and they just rely really heavily on ChatGPT and tools like that to write, to email, to communicate well. I guess, is there, do you have any advice for folks at an early career just, like, how to find that balance of over, not over-relying, but still leveraging these tools?
A I think there's two schools of thought here. One is that sort of the domain, the discipline itself stays static and the way that you approach it changes over time. So whether you're going at it in a manual way or an automated way or an AI augmented way, But I think the other school of thought, which I more believe in is that the discipline itself is changing. And so what it means to market a product, what it means to show up as a fantastic operator is in itself changing. And so if you're not leveraging some of these tools, you will be putting yourself at a disadvantage, but understanding the underlying mechanics, you know, this is why I would still be a very firm believer in, in STEM education is that you understand The fundamental concepts, and then you can have a choice and optionality in how you decide to apply those concepts, but the concepts themselves have to be there in the foundations.
AI assessment note: “understanding the underlying mechanics... you understand The fundamental concepts”
Answered raw tape
D 4 · C 4 · P 4 · Cm 4 4.00
Q issue with people just starting earlier in their career where they just, like, never learn how to do the thing, and they just rely really heavily on ChatGPT and tools like that to write, to email, to communicate well. I guess, is there, do you have any advice for folks at an early career just, like, how to find that balance of over, not over-relying, but still leveraging these tools?
A I think there's two schools of thought here. One is that sort of the domain, the discipline itself stays static and the way that you approach it changes over time. So whether you're going at it in a manual way or an automated way or an AI augmented way, But I think the other school of thought, which I more believe in is that the discipline itself is changing. And so what it means to market a product, what it means to show up as a fantastic operator is in itself changing. And so if you're not leveraging some of these tools, you will be putting yourself at a disadvantage, but understanding the underlying mechanics, you know, this is why I would still be a very firm believer in, in STEM education is that you understand The fundamental concepts, and then you can have a choice and optionality in how you decide to apply those concepts, but the concepts themselves have to be there in the foundations.
AI assessment note: “understanding the underlying mechanics... you understand The fundamental concepts”