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 3 · P 4 · Cm 3 3.85
Q Stripe. Can you hit me with one more? One more.
A Um, I think if I worked a little bit harder, if I worked a little bit harder, I'm not saying I had it, but I, I think I, I could have used some relationships, um, to maybe get into, uh, the Stripe seed. I definitely had visibility into it. Yeah, I know. It might have been, it might have been like a C, A, but it was early. It was very, very early. Oh, remember I had done, I was the platform guy at Salesforce. And, uh, so even in 2007, um, you know, I was doing developer stuff since 2003. So all of the, um, I remember meeting with GitHub when they were three people, even though I was a, I was a seed investor in Heroku from the beginning. So I saw all that early, um, developer stuff. So Twilio, Stripe, all that kind of stuff. I was the first, uh, check into Docker. That's a whole nother story.
AI assessment note: “maybe get into, uh, the Stripe seed. I definitely had visibility into it.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 3 3.85
Q Stripe. Can you hit me with one more? One more.
A Um, I think if I worked a little bit harder, if I worked a little bit harder, I'm not saying I had it, but I, I think I, I could have used some relationships, um, to maybe get into, uh, the Stripe seed. I definitely had visibility into it. Yeah, I know. It might have been, it might have been like a C, A, but it was early. It was very, very early. Oh, remember I had done, I was the platform guy at Salesforce. And, uh, so even in 2007, um, you know, I was doing developer stuff since 2003. So all of the, um, I remember meeting with GitHub when they were three people, even though I was a, I was a seed investor in Heroku from the beginning. So I saw all that early, um, developer stuff. So Twilio, Stripe, all that kind of stuff. I was the first, uh, check into Docker. That's a whole nother story.
AI assessment note: “I think I could have used some relationships to maybe get into the Stripe seed.”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q Okay. So when we think about like the ownership of growth there from Salesforce, if we were to move to Dropbox, another of the iconic brands, what would be the takeaway from there?
A I mean, a lot of takeaways from Dropbox when I, uh, so, uh, I was at Dropbox, uh, in the very beginning, I was employee 11, so it was, uh, 2010 when I started. And it was already clear, even in the very early days, that they were onto something very, very special from a customer acquisition point of view. And one of the many things I learned from Dropbox, um, was the power of being really innovative around customer acquisition. And that's kind of a through line in, in, in my career in general, is, You know, we all love to talk about new technologies, and nerds like me love to talk about app dev frameworks, and databases, and, ah, different engineering, and architectural practices, and debate them all day long. One of the things that, ah, I think is maybe underrated that I'm really attracted to, and I encourage entrepreneurs to think a lot about, is what's changing? Where is their innovation in customer acquisition? And, I mean, it's hard to find a company that was more innovative in customer acquisition, ah, than Dropbox.
AI assessment note: “one of the many things I learned from Dropbox, um, was the power of being”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q Okay. So when we think about like the ownership of growth there from Salesforce, if we were to move to Dropbox, another of the iconic brands, what would be the takeaway from there?
A I mean, a lot of takeaways from Dropbox when I, uh, so, uh, I was at Dropbox, uh, in the very beginning, I was employee 11, so it was, uh, 2010 when I started. And it was already clear, even in the very early days, that they were onto something very, very special from a customer acquisition point of view. And one of the many things I learned from Dropbox, um, was the power of being really innovative around customer acquisition. And that's kind of a through line in, in, in my career in general, is, You know, we all love to talk about new technologies, and nerds like me love to talk about app dev frameworks, and databases, and, ah, different engineering, and architectural practices, and debate them all day long. One of the things that, ah, I think is maybe underrated that I'm really attracted to, and I encourage entrepreneurs to think a lot about, is what's changing? Where is their innovation in customer acquisition? And, I mean, it's hard to find a company that was more innovative in customer acquisition, ah, than Dropbox.
AI assessment note: “one of the many things I learned from Dropbox, um, was the power of being really innovative”
Redirected raw tape
D 3 · C 4 · P 3 · Cm 3 3.30
Q You mentioned the innovation there around customer acquisition channels for Dropbox. Respectfully, Has that not totally gone from Dropbox now? Like, we saw in their latest results, like, no net growth. It seems to have just completely gone. Is that a fair assessment?
A You know, I haven't been, uh, part of Dropbox for over a decade, and so I don't follow it that closely. Um, growth is hard, right? In, in the twenty-twenties, SaaS growth, SaaS growth is hard, and, you know, Dropbox is, is coming from a very large base. I mean, you know, doing billions of dollars in revenue. I think there's, look, it gets back to what I was saying about kind of Salesforce. Look at Salesforce's numbers. Mark used, I don't know if he still does, he used to tweet them every quarter, you know, kind of the full history, right? And I, you look at just accruing billions and billions and billions, not in revenue, but in growth. That is where, that takes a very particular, uh, uh, very intentional growth mindset. And growth is the scarcest Thing in the universe, right? That is the, that's the thing we're all trying to capture and harness. So, um, you know, I, I, I'm, I'm here to critique the things I, I didn't like about Salesforce too, but it's hard to argue with that, especially at that kind of scale. And so, yeah, Dropbox at scale, um, needs to find new acts to drive growth. And I think it's also a lesson for all those entrepreneurs out there, right? Like I've done two startups, zero to one. I most recently was, uh, CEO of a publicly traded company. It's always growth all the time. You're always looking for growth, so the job never stops.
AI assessment note: “I haven't been, uh, part of Dropbox for over a decade, and so I don't follow”
Redirected raw tape
D 2 · C 4 · P 4 · Cm 3 3.25
Q I really like you, Adam, but that feels like it came out of an SAP book. Like, what's an industry transformation narrative? I don't know what it is.
A If your company doesn't have one, it should. You're always trying to do is navigate your company on two dimensions. One is be emotive, and the other is be strategic. You need to be emotive And, right, because you want people to care. You want people to have a, ah, ah, ah, ah, an experience with your product that, um, they, they feel emotionally and passionately and viscerally connected to. And that could, you could be like, oh, that sounds silly. That's not how we did developer tools in the, you know, in the nineties, right? It was like, who cares as a compiler? Well, think about developer tools now. Think about how emotive the brands are of like GitHub or, Uh, or Heroku, or, you know, you know, more modern ones like Vercel. These are deeply.
AI assessment note: “If your company doesn't have one, it should. You're always trying to do”
Redirected raw tape
D 2 · C 4 · P 3 · Cm 3 3.00
Q I really like you, Adam, but that feels like it came out of an SAP book. Like, what's an industry transformation narrative? I don't know what it is.
A If your company doesn't have one, it should. You're always trying to do is navigate your company on two dimensions. One is be emotive, and the other is be strategic. You need to be emotive And, right, because you want people to care. You want people to have a, ah, ah, ah, ah, an experience with your product that, um, they, they feel emotionally and passionately and viscerally connected to. And that could, you could be like, oh, that sounds silly. That's not how we did developer tools in the, you know, in the nineties, right? It was like, who cares as a compiler? Well, think about developer tools now. Think about how emotive the brands are of like GitHub or, Uh, or Heroku, or, you know, you know, more modern ones like Vercel. These are deeply.
AI assessment note: “If your company doesn't have one, it should. You're always trying to do”
Redirected raw tape
D 2 · C 3 · P 3 · Cm 2 2.55
Q You mentioned there about kind of the innovation around customer acquisition channels. I feel that a lot of customer acquisition channels today have kind of really run their course. We see TikTok absolutely bang for consumer social and for direct to consumer, but it's a real fricking challenge. How do you think about that? And am I wrong and too negative?
A It's an excellent, excellent question. And, um, I, it's something I think about a lot, you know, I'm more of an enterprise person. So if you think about what does customer acquisition look like for, Uh, kind of traditional SaaS versus, you know, a consumer app, which is with ATT and everything that's happening in that world, that's a whole different, uh, landscape. I think, you know, Not surprisingly, and it's maybe not directly customer acquisition, but it is kind of go to market. And of course, I'm not going to win any awards for saying this, but the impact of AI. And I will, I'll put a plug in. So, um, my most recent gig, uh, I'm going off of your rapid fire round, but, um, so I, I, uh, most recently was interim CEO, uh, at Vimeo, uh, where I previously been on board and, you know, Vimeo is now, uh, Twenty-year-old company, publicly traded, and I had to onboard myself. And one of the things that Vimeo, um, had at the time, and there are many tools in the space and they're all great, is Gong. And the ability to see a sales call and have it, you know, be analyzed by AI as somebody in my role as CEO trying to onboard, um, uh, versus, you know, the tools and what we, uh, uh, had before is miraculous. And you think about what, you know, Gong and, um, all of their, uh, uh, uh, brethren companies are, uh, you know, uh, being able to capture with all of that data and really start th…
AI assessment note: “maybe not directly customer acquisition, but it is kind of go to market”
Redirected raw tape
D 2 · C 3 · P 3 · Cm 2 2.55
Q You mentioned the innovation there around customer acquisition channels for Dropbox. Respectfully, Has that not totally gone from Dropbox now? Like, we saw in their latest results, like, no net growth. It seems to have just completely gone. Is that a fair assessment?
A You know, I haven't been, uh, part of Dropbox for over a decade, and so I don't follow it that closely. Um, growth is hard, right? In, in the twenty-twenties, SaaS growth, SaaS growth is hard, and, you know, Dropbox is, is coming from a very large base. I mean, you know, doing billions of dollars in revenue. I think there's, look, it gets back to what I was saying about kind of Salesforce. Look at Salesforce's numbers. Mark used, I don't know if he still does, he used to tweet them every quarter, you know, kind of the full history, right? And I, you look at just accruing billions and billions and billions, not in revenue, but in growth. That is where, that takes a very particular, uh, uh, very intentional growth mindset. And growth is the scarcest Thing in the universe, right? That is the, that's the thing we're all trying to capture and harness. So, um, you know, I, I, I'm, I'm here to critique the things I, I didn't like about Salesforce too, but it's hard to argue with that, especially at that kind of scale. And so, yeah, Dropbox at scale, um, needs to find new acts to drive growth. And I think it's also a lesson for all those entrepreneurs out there, right? Like I've done two startups, zero to one. I most recently was, uh, CEO of a publicly traded company. It's always growth all the time. You're always looking for growth, so the job never stops.
AI assessment note: “I haven't been, uh, part of Dropbox for over a decade”
Redirected raw tape
D 2 · C 3 · P 3 · Cm 2 2.55
Q You mentioned there about kind of the innovation around customer acquisition channels. I feel that a lot of customer acquisition channels today have kind of really run their course. We see TikTok absolutely bang for consumer social and for direct to consumer, but it's a real fricking challenge. How do you think about that? And am I wrong and too negative?
A It's an excellent, excellent question. And, um, I, it's something I think about a lot, you know, I'm more of an enterprise person. So if you think about what does customer acquisition look like for, Uh, kind of traditional SaaS versus, you know, a consumer app, which is with ATT and everything that's happening in that world, that's a whole different, uh, landscape. I think, you know, Not surprisingly, and it's maybe not directly customer acquisition, but it is kind of go to market. And of course, I'm not going to win any awards for saying this, but the impact of AI. And I will, I'll put a plug in. So, um, my most recent gig, uh, I'm going off of your rapid fire round, but, um, so I, I, uh, most recently was interim CEO, uh, at Vimeo, uh, where I previously been on board and, you know, Vimeo is now, uh, Twenty-year-old company, publicly traded, and I had to onboard myself. And one of the things that Vimeo, um, had at the time, and there are many tools in the space and they're all great, is Gong. And the ability to see a sales call and have it, you know, be analyzed by AI as somebody in my role as CEO trying to onboard, um, uh, versus, you know, the tools and what we, uh, uh, had before is miraculous. And you think about what, you know, Gong and, um, all of their, uh, uh, uh, brethren companies are, uh, you know, uh, being able to capture with all of that data and really start th…
AI assessment note: “it's maybe not directly customer acquisition, but it is kind of go to market”
