The Exchanges

Q Can I ask, should the founder not be the visionary and the CPO not be the craftsperson?

A That is often the case. Again, it's by definition that, like, you need to have a Big vision for something, something that does not exist or is highly suboptimal in the world, uh, that you want to, uh, you want to fix. And so, so oftentimes, uh, founders end up being, uh, that kind of visionary archetype. Uh, and on founding teams, I've found that it's, it's usually, you know, one of the founders that's the visionary. Uh, and perhaps, you know, there's another founder that's more like an operator, uh, and maybe even a third that's more like a craftsperson. Uh, and I'm not saying it has to be that kind of composition, uh, but typically, you know, like this point I've kind of advised, uh, you know, a hundred plus companies just in the past two years on various topics. Uh, and, uh, I found that like, usually there's one founder who's the core visionary, who, who then takes ownership of the product, uh, early on naturally. Uh, and kind of like, you know, sometimes wears the craftsperson hat, and like I said, they can be fairly good at it to kind of translate that vision into certain kind of product, uh, manifestations. Uh, but at some point, uh, it becomes harder for them, like, because once you start getting users and once you start getting usage, what ends up happening is users are pulling you in many different directions, right? The visionary has a very clear view of the future, …

AI assessment note: “That is often the case. Again, it's by definition”

Q no, no, we don't want to grow users as much as possible. That's not a sign of product market fit. What is, is number of sessions per day, number of tasks created. I don't care about top line growth of users, but the tasks that they do to signify their product love. How do you think about, like, finding the right metric within user adoption when there are so many?

A Yeah. Uh, so I think metrics is a highly misunderstood, uh, concept and, uh, there's just so much, uh, nuance to it, uh, that, you know, this kind of question gets, um, debated endlessly within many companies, including extremely successful companies. It's like, what's the right metric? And let's do a bunch of these meetings to make it happen. And it, and it, and it, and it, and it's not, it's not because it's, uh, easy. It's not, it's not easy. Uh, but, uh, I think we need a You know, a more fundamental view here when we talk about things like, you know, user metrics and user adoption and those types of things. So, so the way I look at it, Harry, is, um, I think overall product metric metrics fall in about six categories. So that's a good place to start. And they are, uh, health metrics, usage metrics, adoption metrics, satisfaction metrics, Ecosystem metrics and outcome metrics. Okay, so we don't need to get into each of these six, and I have some articles that we can throw into the show notes if folks are more interested in these. But, but first thing you need to recognize is that there isn't like one metric, like there are many different types of metrics or categories of metrics that you need to be cognizant of. Now, You know, one of these metrics is, uh, adoption metrics, right? So, and that's where we get into things like user adoption, user growth, and those sorts of thi…

AI assessment note: “overall product metric metrics fall in about six categories”

Q great product leaders in particular. And when we spoke before, you said that there are three product leaders, um, in terms of different types. I'd love to just understand. I'm, again, the founder and CEO. I'm, I'm hiring my first CPO, head of product, product leader, whatever we want to call them. What are the three different product leader personas that I should know about when entering this hiring process?

A Yeah. So, uh, I, at this point, uh, just in the last year, I've spoken with, uh, more than 50 founders about, uh, the general area of, um, oh, my product is, uh, growing really, uh, fast and, uh, I think I, I need a CPO or a VP product or, or my board tells me, or my VCs tell me, uh, that I should go hire a VP product, uh, and delegate, uh, various aspects of the product. Uh, to that person. Uh, and so, uh, you know, they reach out to me, and, uh, you know, sometimes we'll get on a call, uh, to discuss it, and every single conversation is actually very different, uh, and, uh, because fundamentally, if product is what's gonna drive your startup success, uh, you have to create your own script, uh, around, you know, uh, around what you are looking for, uh, and that can only be done if, uh, we understand, uh, Uh, how your business is going to be driven forward, uh, and whatnot. Um, from those conversations, uh, I have been able to extract some, uh, patterns. And so, you know, one of the patterns is, uh, the three types of product leaders, and they are, uh, the operator, uh, the craftsperson, uh, and the visionary. Uh, and, um, you know, when I kind of start sharing, uh, you know, these names or these labels, uh, Uh, uh, founders will start asking me like, oh, so like, which one is right for me? Just tell me which one is right for me. And I was like, no, no, no, not so fast. Um, wha…

AI assessment note: “the three types of product leaders, and they are, the operator, the craftsperson, and the visionary.”

Q How do you determine when to listen to customer feedback versus when to progress with expected and planned roadmap and ignore it? Tough question.

A Oh boy. That's, uh, you know, the, the perennial question of product management. Uh, and look, my view on this is, um, There are Some teams that say that, um, they are, uh, highly customer driven, uh, and that's seen kind of as a virtue, which is like, oh, we are very customer driven. Um, but in reality, what ends up happening when you kind of label yourself that way, that you're customer driven is, uh, you end up just following what customers are telling you. Uh, and, and sometimes that can be the right answer, uh, especially. You know, once your product has already, uh, sort of, like, reached a certain scale, uh, you can be customer-driven, uh, and build, uh, you know, what they ask you to build, and because you already have some assets, some differentiation, uh, and so, so that works. Uh, but I have found that it's very important, uh, to, you know, ground what you do, uh, in terms of a core strategy. So the strategy becomes a, the piece, uh, the artifact, uh, the guideline, uh, for when you listen to customers and when you don't listen to customers. Um, so, and this is best explained, uh, perhaps, uh, via an example. Um, so, uh, you know, one of the products I managed at Stripe, uh, was, uh, Stripe terminal, which is an in-person kind of point of sale payment solution. Uh, and Uh, point of sale, uh, payments have been around for a really long time, and Stripe was creating it…

AI assessment note: “strategy becomes the guideline for when you listen to customers and when you don't”

Q Um, and so what's the difference between a competent and an incompetent visionary given so much of their beliefs of future held? What's the difference?

A Yeah. So it is, uh, you, you cannot define it, uh, looking forward, uh, simply because ultimately, and there's not going to be a satisfying answer, but this is, True. Uh, as far as I've seen is you're just more right about where the world is headed. Uh, and, and there are people, uh, you know, clearly there are people who are more right than others. This is actually why I love Amazon's one of Amazon's leadership principles is, uh, leaders are right a lot. Uh, and, and it's my favorite of their, they have really great leadership principles. This one's my favorite. Because, uh, this is so misunderstood because, you know, there are many people who say, well, like, you know, there is no such thing as being visionary, as being right a lot. Like you just, you know, you, but you, you, you, you follow a process and, uh, make sure it's a good process. Make sure you set OKRs, make sure you, uh, execute, uh, well and success will be yours. No, that is not how anything works in the real world. Right? That is actually the operator speaking when that operator has taken a product from say, 20 to 60, or 60 to a hundred, and it's easy to say that, oh, success is all about just following processes, setting structures, setting goals, and diligently following them, and all of that is very important, but they forget that it's actually A high degree of creativity and instinct that gave you the luxur…

AI assessment note: “you're just more right about where the world is headed”

Q no, no, we don't want to grow users as much as possible. That's not a sign of product market fit. What is, is number of sessions per day, number of tasks created. I don't care about top line growth of users, but the tasks that they do to signify their product love. How do you think about, like, finding the right metric within user adoption when there are so many?

A Yeah. Uh, so I think metrics is a highly misunderstood, uh, concept and, uh, there's just so much, uh, nuance to it, uh, that, you know, this kind of question gets, um, debated endlessly within many companies, including extremely successful companies. It's like, what's the right metric? And let's do a bunch of these meetings to make it happen. And it, and it, and it, and it, and it's not, it's not because it's, uh, easy. It's not, it's not easy. Uh, but, uh, I think we need a You know, a more fundamental view here when we talk about things like, you know, user metrics and user adoption and those types of things. So, so the way I look at it, Harry, is, um, I think overall product metric metrics fall in about six categories. So that's a good place to start. And they are, uh, health metrics, usage metrics, adoption metrics, satisfaction metrics, Ecosystem metrics and outcome metrics. Okay, so we don't need to get into each of these six, and I have some articles that we can throw into the show notes if folks are more interested in these. But, but first thing you need to recognize is that there isn't like one metric, like there are many different types of metrics or categories of metrics that you need to be cognizant of. Now, You know, one of these metrics is, uh, adoption metrics, right? So, and that's where we get into things like user adoption, user growth, and those sorts of thi…

AI assessment note: “overall product metric metrics fall in about six categories”

Q When does that transition happen from not needing the operator to needing the operator? Is it post product market fit? Is it series C and beyond? Is it post international expansion? Like when is that transition of now you need an operator?

A Yeah. So, uh, you know, I personally went through that transition myself, uh, when I was, uh, leading connect, which is, uh, Stripe connect, which is, uh, you know, a major, major business for Stripe. I, I started leading it when, uh, uh, you know, the product was already being used by quite a few of Stripe customers. Uh, the team was only four engineers at the time. Uh, and so it was like, uh, early ish in its, uh, life. Uh, and, uh, the business just, I was leading it for three years and the business and the product was just like, you know, scaled tremendously in that time. Uh, and then at some point I realized that. Oh, this is getting too big for me and not big in terms of just, you know, my ability to manage the business or my ability to, um, to manage the team, but more in terms of, um, uh, just what I'm passionate about. Uh, because, uh, you know, as during those three years, the product grew, I don't know how many X, but like significantly. Uh, and so, and the team grew correspondingly as well. Uh, and I just realized that like I was doing things. My day was spent in doing things that frankly, I did not enjoy. And in many cases I found boring, but that was the job at that point. Uh, and so back then I went, uh, to my manager, uh, John Collison was my manager back then. Uh, and I said, you know, I, I think In, within the next several months, I think I need to go back to …

AI assessment note: “I personally went through that transition myself, uh, when I was, uh, leading connect”

Q When does that transition happen from not needing the operator to needing the operator? Is it post product market fit? Is it series C and beyond? Is it post international expansion? Like when is that transition of now you need an operator?

A Yeah. So, uh, you know, I personally went through that transition myself, uh, when I was, uh, leading connect, which is, uh, Stripe connect, which is, uh, you know, a major, major business for Stripe. I, I started leading it when, uh, uh, you know, the product was already being used by quite a few of Stripe customers. Uh, the team was only four engineers at the time. Uh, and so it was like, uh, early ish in its, uh, life. Uh, and, uh, the business just, I was leading it for three years and the business and the product was just like, you know, scaled tremendously in that time. Uh, and then at some point I realized that. Oh, this is getting too big for me and not big in terms of just, you know, my ability to manage the business or my ability to, um, to manage the team, but more in terms of, um, uh, just what I'm passionate about. Uh, because, uh, you know, as during those three years, the product grew, I don't know how many X, but like significantly. Uh, and so, and the team grew correspondingly as well. Uh, and I just realized that like I was doing things. My day was spent in doing things that frankly, I did not enjoy. And in many cases I found boring, but that was the job at that point. Uh, and so back then I went, uh, to my manager, uh, John Collison was my manager back then. Uh, and I said, you know, I, I think In, within the next several months, I think I need to go back to …

AI assessment note: “during those three years, the product grew... and the team grew correspondingly”

Q great product leaders in particular. And when we spoke before, you said that there are three product leaders, um, in terms of different types. I'd love to just understand. I'm, again, the founder and CEO. I'm, I'm hiring my first CPO, head of product, product leader, whatever we want to call them. What are the three different product leader personas that I should know about when entering this hiring process?

A Yeah. So, uh, I, at this point, uh, just in the last year, I've spoken with, uh, more than 50 founders about, uh, the general area of, um, oh, my product is, uh, growing really, uh, fast and, uh, I think I, I need a CPO or a VP product or, or my board tells me, or my VCs tell me, uh, that I should go hire a VP product, uh, and delegate, uh, various aspects of the product. Uh, to that person. Uh, and so, uh, you know, they reach out to me, and, uh, you know, sometimes we'll get on a call, uh, to discuss it, and every single conversation is actually very different, uh, and, uh, because fundamentally, if product is what's gonna drive your startup success, uh, you have to create your own script, uh, around, you know, uh, around what you are looking for, uh, and that can only be done if, uh, we understand, uh, Uh, how your business is going to be driven forward, uh, and whatnot. Um, from those conversations, uh, I have been able to extract some, uh, patterns. And so, you know, one of the patterns is, uh, the three types of product leaders, and they are, uh, the operator, uh, the craftsperson, uh, and the visionary. Uh, and, um, you know, when I kind of start sharing, uh, you know, these names or these labels, uh, Uh, uh, founders will start asking me like, oh, so like, which one is right for me? Just tell me which one is right for me. And I was like, no, no, no, not so fast. Um, wha…

AI assessment note: “the three types of product leaders, and they are, the operator, the craftsperson, and the visionary.”

Q I totally get you there, especially in kind of the verticalization. Can I ask you, when you think about your angel investing today, How do you think that has changed your product mindset, having had the exposure that you now have from advising and investing in so many?

A Yeah. You know, um, I think the, the core thing that, uh, perhaps, um, you know, and this, this one's very obvious, um, uh, in hindsight, but like, you know, previously I, when I started angel investing, uh, I, I was very attracted to the idea. Uh, and again, being sort of like a product idea person or crafts person, like, you know, I was like, this needs to exist in the world. Uh, and so, so I'm very excited about this. I want to invest in this. I want to support this founder and whatnot. Uh, and what I realized over time is, uh, that, that is a necessary, but by no means a sufficient condition. In fact, it's not even one of the main conditions. Uh, and instead, um, I realized that like the core thing that, um, Matters is just, you know, how great is this founder? And this is why it's obvious, right? Like it's, it's not like I'm the first person, uh, to realize this, but I had to sort of like go through that journey to really accept that realization that, uh, you know, if the founder, like, and now the core question I ask is, uh, uh, is this person among the most capable people I've ever encountered? Right. Uh, and it's a very simple litmus test, and obviously, you know, that requires conversation, that requires asking, you know, good questions and whatnot. Uh, but, um, if that is true, and that's the bar I apply for advising as well, right? Like, because, uh, I, I wanna keep …

AI assessment note: “realized over time is... the core thing that Matters is just... how great is this founder”