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 →
Partly raw tape
D 2 · C 4 · P 3 · Cm 3 3.00
Q Okay. Uh, so then we have the thirty million dollars and we have to scale and we have some points breaking. Uh, we have strategies to scale. What did you do that with the benefit of hindsight you wish you hadn't done?
A You know, one of the things at Toast that was interesting was, and this is still an issue today, is how much do you want to do? So our focus from day one was we're going to solve for restaurants, and we're going to be the best solution for restaurants is the vertical, you know, the thesis, and the strategy was by building a platform that was purpose built, we can, we can, we can solve the problems of this industry better than anybody else in the world. As we got going, We realized the sales efficiency though, we wasn't quite there. And so we'd say, well, what can we offer where, um, we can make the financials work? Because it was a highly considered purchase back to what you said. It's like, you know, these point of sales, like I think it's described to me many times as like a root canal, switching out point of sale systems.
AI assessment note: “how much do you want to do? So our focus from day one”
Partly raw tape
D 3 · C 3 · P 3 · Cm 3 3.00
Q How does that change your approach then in terms of outbound sales, in terms of org design? Is it focusing hyper-local, building very local teams, doing kind of guerrilla marketing on a per-street basis? How does that actually change with that realization?
A One of the challenges is like, how do you play the long game and the short game? Because if you always play a short game, you just have more and more sales density in the most successful markets to grow even faster, because the productivity was some of the best. We were cutting territories. And growing faster. And our reps were more productive. And so, but they also have to put, you know, the foundational teams in all these markets around the country. It's always easier actually that we, what we noticed was to actually add maybe more in some of these markets we were seeing more success in. And so you balance the two. And, and so for us, but at the end of the day, like the, the more important thing was actually like, can you hire great people? Like this goes back to like scaling companies and this goes back to the processes to actually assess What you're looking for, like, and we have these, like, big three on how you hire now. Do you, how do you onboard? Do you have an onboarding program? One of the rules we, we, one of the things we do is everyone that joins the company, whether you're an IC, a BDR, um, you know, outbound prospecting, or a rep closing deals, or a manager, you have to go sell. If you're a district manager, it's great that you've managed people before in running sales team, but you got to go sell toast for a quarter and learn it.
AI assessment note: “have more and more sales density in the most successful markets to grow even faster”
Answered raw tape
D 3 · C 3 · P 3 · Cm 2 2.85
Q Did you know that from day one? Did you know that the fintech component would be a good one?
A Yeah, I think so. So it's not like, yeah, we, and we realized, not maybe on day one, but I think we realized Within 10 customers that, like, the, the, the financial model wasn't obvious to me because restaurants were like, you know, and we were, this is early too, but we're like, you know, we were making two, 300 bucks a month on the software at most, and it was just, it was, um, not obvious given how much my products weren't very good either, but the amount of support. I remember talking to one customer being like, you're calling me too much, like, this is not scalable at all given what you're paying us, and so I think it's, it's gotta, it's, it's a lot of factors. It's never like a black and white answer, But you want to get some model that is at least somewhat credible in your head, right? So you want to put together some simple model that says, here's what it could be, you know, but then after that very quickly pivot to like, okay, how do we make customers love what you do? So it's, you need to do both. But I think in back to Bessemer in early days, like with Kent, you know, we, we met with Kent and, um, of course he didn't invest and we raised to Steve and then Can't put, you know, uh, putting money in our Series A. And so, you know, we had this conversation many times, and we asked him, like, hey, how come you didn't invest? And he was like, well, you know, you guys seem …
AI assessment note: “not maybe on day one, but I think we realized Within 10 customers”
Redirected raw tape
D 3 · C 2 · P 3 · Cm 2 2.55
Q Did you know that from day one? Did you know that the fintech component would be a good one?
A Yeah, I think so. So it's not like, yeah, we, and we realized, not maybe on day one, but I think we realized Within 10 customers that, like, the, the, the financial model wasn't obvious to me because restaurants were like, you know, and we were, this is early too, but we're like, you know, we were making two, 300 bucks a month on the software at most, and it was just, it was, um, not obvious given how much my products weren't very good either, but the amount of support. I remember talking to one customer being like, you're calling me too much, like, this is not scalable at all given what you're paying us, and so I think it's, it's gotta, it's, it's a lot of factors. It's never like a black and white answer, But you want to get some model that is at least somewhat credible in your head, right? So you want to put together some simple model that says, here's what it could be, you know, but then after that very quickly pivot to like, okay, how do we make customers love what you do? So it's, you need to do both. But I think in back to Bessemer in early days, like with Kent, you know, we, we met with Kent and, um, of course he didn't invest and we raised to Steve and then Can't put, you know, uh, putting money in our Series A. And so, you know, we had this conversation many times, and we asked him, like, hey, how come you didn't invest? And he was like, well, you know, you guys seem …
AI assessment note: “not maybe on day one, but I think we realized Within 10 customers”
Redirected raw tape
D 2 · C 3 · P 3 · Cm 2 2.55
Q How does that change your approach then in terms of outbound sales, in terms of org design? Is it focusing hyper-local, building very local teams, doing kind of guerrilla marketing on a per-street basis? How does that actually change with that realization?
A One of the challenges is like, how do you play the long game and the short game? Because if you always play a short game, you just have more and more sales density in the most successful markets to grow even faster, because the productivity was some of the best. We were cutting territories. And growing faster. And our reps were more productive. And so, but they also have to put, you know, the foundational teams in all these markets around the country. It's always easier actually that we, what we noticed was to actually add maybe more in some of these markets we were seeing more success in. And so you balance the two. And, and so for us, but at the end of the day, like the, the more important thing was actually like, can you hire great people? Like this goes back to like scaling companies and this goes back to the processes to actually assess What you're looking for, like, and we have these, like, big three on how you hire now. Do you, how do you onboard? Do you have an onboarding program? One of the rules we, we, one of the things we do is everyone that joins the company, whether you're an IC, a BDR, um, you know, outbound prospecting, or a rep closing deals, or a manager, you have to go sell. If you're a district manager, it's great that you've managed people before in running sales team, but you got to go sell toast for a quarter and learn it.
AI assessment note: “the more important thing was actually like, can you hire great people?”
Redirected raw tape
D 2 · C 3 · P 3 · Cm 2 2.55
Q Okay. Uh, so then we have the thirty million dollars and we have to scale and we have some points breaking. Uh, we have strategies to scale. What did you do that with the benefit of hindsight you wish you hadn't done?
A You know, one of the things at Toast that was interesting was, and this is still an issue today, is how much do you want to do? So our focus from day one was we're going to solve for restaurants, and we're going to be the best solution for restaurants is the vertical, you know, the thesis, and the strategy was by building a platform that was purpose built, we can, we can, we can solve the problems of this industry better than anybody else in the world. As we got going, We realized the sales efficiency though, we wasn't quite there. And so we'd say, well, what can we offer where, um, we can make the financials work? Because it was a highly considered purchase back to what you said. It's like, you know, these point of sales, like I think it's described to me many times as like a root canal, switching out point of sale systems.
AI assessment note: “one of the things at Toast that was interesting was”
Redirected raw tape
D 2 · C 3 · P 2 · Cm 2 2.30
Q How much juice can you extract from restaurants? And I know that's a horrible statement, and that's why I'm a VC, obviously. Um, but like, how much revenue can you actually get before you hit the ceiling and go, we gotta go to retail. We gotta go to broader hospitality.
A First of all, I think it's about value creation. I think the monetization follows. It always starts with value creation. This is one piece of advice. It's like everyone should focus on what is the value you're creating. I think often companies get in trouble when they're looking around to say, how do we drive our metrics versus the customer's metrics? And then back to like the strategy of like, how much can you do? It's really hard, but the fundamental question is like, how much can you do well? Which actually goes back to people. If you've got average talent, You get in the details of why it's not working, and there's a million reasons why the things don't work, and you get into this mode of, like, your micromanaging, versus, like, you bring in great talent, and actually, like, they go and figure it out, and so a lot of, like, how much can you do, and how much can you do well always goes back to people and talent, um, and for us, I think, you know, when we think about all the different variables and all the different ways in which you can grow, as we, as we looked at, like, You know, and maybe you could argue we're doing too much, but we, we have, you know, we, we see opportunity where the platform we serve, the strategy can work in other segments, in other geos, upmarket enterprise, and we can expand the platform. And the question is, how do you sequence all this in ways, rig…
AI assessment note: “First of all, I think it's about value creation. I think the monetization follows.”
Not addressed raw tape
D 1 · C 3 · P 2 · Cm 2 2.00
Q Not at all. Um, I've made many hiring mistakes, dude. What's your biggest hiring mistake?
A Like hiring is hard. And so just building a rigorous process actually is really important. And we, we're still not great at it in trends because it's hard because it takes time, right? Like you're busy, but like, and it differs per function. Yeah. Fair. But I think, yes, it does. But I think fundamentally, like doing the hard work to say, what are you looking for upfront the process, writing it down, right? Being clear about it. Sometimes there's only like the basics are lost. Like, what are you hiring this person for? What are they going to do? Like, and being clear about it as a group. In the interview process, like having, I think Amazon does as well, like writing down your notes, like clearly the transcript of what happened in the interview. I think in the interview itself, you have to be able to go deep, because you only have so much time, and it's hard to go deep and ask hard questions somebody you don't know. One of the things I've learned is you have to do it, even if it's uncomfortable or hard, because you have to understand, like, you know, where has this person Really dealt with grit, uh, dealt with, you know, challenges and had to be resilient. Where, what have they done that has been impactful where they were the driver on the bus and not just the passenger. And so that, that's what's like really important in the process.
AI assessment note: “Like hiring is hard. And so just building a rigorous process actually is really important.”
Redirected raw tape
D 1 · C 3 · P 2 · Cm 2 2.00
Q How much juice can you extract from restaurants? And I know that's a horrible statement, and that's why I'm a VC, obviously. Um, but like, how much revenue can you actually get before you hit the ceiling and go, we gotta go to retail. We gotta go to broader hospitality.
A First of all, I think it's about value creation. I think the monetization follows. It always starts with value creation. This is one piece of advice. It's like everyone should focus on what is the value you're creating. I think often companies get in trouble when they're looking around to say, how do we drive our metrics versus the customer's metrics? And then back to like the strategy of like, how much can you do? It's really hard, but the fundamental question is like, how much can you do well? Which actually goes back to people. If you've got average talent, You get in the details of why it's not working, and there's a million reasons why the things don't work, and you get into this mode of, like, your micromanaging, versus, like, you bring in great talent, and actually, like, they go and figure it out, and so a lot of, like, how much can you do, and how much can you do well always goes back to people and talent, um, and for us, I think, you know, when we think about all the different variables and all the different ways in which you can grow, as we, as we looked at, like, You know, and maybe you could argue we're doing too much, but we, we have, you know, we, we see opportunity where the platform we serve, the strategy can work in other segments, in other geos, upmarket enterprise, and we can expand the platform. And the question is, how do you sequence all this in ways, rig…
AI assessment note: “First of all, I think it's about value creation. I think the monetization follows.”
Not addressed raw tape
D 1 · C 3 · P 2 · Cm 2 2.00
Q Not at all. Um, I've made many hiring mistakes, dude. What's your biggest hiring mistake?
A Like hiring is hard. And so just building a rigorous process actually is really important. And we, we're still not great at it in trends because it's hard because it takes time, right? Like you're busy, but like, and it differs per function. Yeah. Fair. But I think, yes, it does. But I think fundamentally, like doing the hard work to say, what are you looking for upfront the process, writing it down, right? Being clear about it. Sometimes there's only like the basics are lost. Like, what are you hiring this person for? What are they going to do? Like, and being clear about it as a group. In the interview process, like having, I think Amazon does as well, like writing down your notes, like clearly the transcript of what happened in the interview. I think in the interview itself, you have to be able to go deep, because you only have so much time, and it's hard to go deep and ask hard questions somebody you don't know. One of the things I've learned is you have to do it, even if it's uncomfortable or hard, because you have to understand, like, you know, where has this person Really dealt with grit, uh, dealt with, you know, challenges and had to be resilient. Where, what have they done that has been impactful where they were the driver on the bus and not just the passenger. And so that, that's what's like really important in the process.
AI assessment note: “Like hiring is hard. And so just building a rigorous process actually is really important.”
