three two one zero you have now arrived at your destination sure this is such a joy to do i've been a fan of yours from afar on twitter for a while but thank you so much for joining me today thanks for having me harry not at all as i said i've loved some of your twitter threads and they've been pretty informative to me uh but let's start with a little bit on you so you've been part of some of the most incredible orcs from stripe twitter google how did you make your way into the world of product first and let's start there yeah so i started my career uh back in the difficult tough days of the valley this was 2001 as an engineer and as an engineer here in california who needed a visa it was very difficult to get jobs back then it was like drastically different environment than the one we found ourselves in over the last decade and so i was lucky enough though to uh you know join some really great teams uh early on in my career as an engineer and uh i moved to silicon valley in 2003 to join a team that used to formally be loud cloud the mark and recent ben horowitz company and when i was there i got introduced to product management uh mainly because i found myself getting sent to customer interviews and customer meetings and whatnot by my manager and i didn't quite understand why because i was just an engineer very early career but i think my managers back then saw in something in me that i did not uh yet uh so uh and and i found myself getting very interested in um learning about what customers are doing with the product and and particularly coming up with you know more creative solutions uh about uh you know to solve the customer problems and that's when i realized that uh you know maybe i should try this product management thing and so uh traditionally back then most people would do their mba in order to get into product management and i decided i did not want to do that i considered it but i decided i did not want to do that and i just said oh let me just apply to some consumer internet companies uh web 2.0 was big back then and i wanted to work on web products and so i applied to a few companies and talked to google yahoo at the time yahoo during its better days and that was my first uh real product management experience is when i joined yahoo as a product manager back in 2006 uh and then since then it's been a really fun ride there's a lot that i just want to unpack i want to start which is some nomenclature product management is thrown about quite a lot as a term when i say product management to usher ass how do you define it yeah i love that question because um there are many definitions of product management and so my definition is product management is the art science and practice of making successful products and making products successful okay so there are two aspects here and it's not just a play on words both are very important making successful products uh means that you often have to start with uh nothing and then make a successful product and so that's kind of the early stage to reaching product market fit and beyond scaling so so so that's one aspect of it the other aspect which is making products successful uh is when say there is a product that already exists and maybe you know you weren't there at the beginning but it's at a stage where it's either poised for a lot of growth or it's not maybe it's even a turnaround story and product management again is the art science and practice of actually making that happen right and um you know when i when i share this harry a lot of times people will uh ask me oh but wait what is success can you define success for me uh and so my view of success is it's not complicated product success you need to start with three things to begin evaluating product success which is uh user adoption customer satisfaction and business impact right ultimately any product uh you need to start with each of these three or a subset of these three to determine product success now the exact metric may vary depending on your product depending on its stage and whatnot but ultimately building successful products is about user adoption customer satisfaction and business impact this is where i love the show because like this was never obviously structured um like user adoption is a first one there are so many different metrics that one can choose as a focus point you know i speak to many who have number of users and i'm like no 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 yeah so i think metrics is a highly misunderstood concept and there's just so much uh nuance to it that you know this kind of question gets 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's not it's not because it's easy it's not it's not easy but 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 i think overall product metrics fall in about six categories so that's a good place to start and they are 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 things one thing to observe about adoption metrics is that adoption doesn't happen on its own right like there needs need to be certain conditions that preconditions that need to be satisfied so you can get to adoption so when i'm talking to an early stage team product or startup and we're talking about adoption i often encourage them to have some sort of a north star on adoption whatever that is whether it's you know number of active users or or users that are retained or new user sign ups those are all variants of adoption metrics uh so so that's fine but uh i think it's even more important like a lot of teams just stop there a lot of teams say okay this is our adoption metric and now we're going to make it better and that's the mistake the mistake there is again adoption is an end result of something else you do so you're better off measuring uh those those things those other things and that's where things like usage metrics come in or even health metrics come in so usage metric is about how people are actually using the product right and a lot of teams don't actually have a lot of visibility into that only if you understand what type of usage leads to adoption will you actually be able to address the inputs because in some ways adoption is the output of your activities absolutely so that this is always what frustrates me when they give me like output matrix and it's like no no i want input match i want number of tasks created in notion number of new projects number of net new additions to each project in terms of sharing capabilities what was health matrix strass yeah health metrics are you know another way to define it is like their hygiene metrics and the key the way i like to describe a metric is like what key question is this category of metric answering right so with help metrics the key question that it's answering is is this product available and performing in the manner that users would reasonably expect right so you users are not using your product in isolation they use many different products and human beings compare how your product does compared to other things that they're used to using and so you know users implicitly tend to have a certain type of expectation for the for the type of product you are and those expectations vary if i'm using an e-commerce product my expectations are very different and i'm using a social product versus if i'm using some internal uh you know enterprise product as just an example um so is this product available and performing in the manner that users would reasonably expect is the key question and some examples of health metrics are latency initial load time uh data loss rate errors that you see so these are things that are really important for you to uh keep track of because oftentimes you know we we fixate on sort of the the growth funnel and all of those things and if we lose sight of like basics that we're not getting right in the product uh that are perhaps not very evident then we might wonder why you know adoption is not where we want it to be um so so that's kind of how i look at health metrics and you know health metrics by themselves will rarely drive your business forward but health metrics if you don't pay attention to them can uh drastically impede your business totally with you a leaky bucket is never a good bucket to have um you know when you speak in you advise incredible companies that i spoke to many of the founders that you advise um when you speak to founders and work with founders today what do you think is the most misunderstood metric category and and why do you think that is um i think one category that is highly misunderstood is well it's not so much a category as it is a type which is you know these days a lot of people talk about the north star metric the nsm what's your not star metric and um i'll tell you i get a lot of emails and messages over all dms from folks who who ask me you know hey i have this product i have this startup and uh you know have some some ideas on what my not star metric should be and uh and here it is and so what do you think and and the reason i say this concept is misunderstood is that the not sir metric is not a panacea uh and you know there are some you know some people who want to train you on not star metrics may make it seem that way but the north star metric is not a panacea just defining finding the perfect metric uh as your nsm is actually not necessary right like you when you're when you're especially when you're early stage uh what you're mainly looking for is is my product resonating right and so what i often advise founders is you know is classic like don't try for perfection with your nordstrom metric if you found something that generally works and is measurable just pick it as your not star metric uh you don't have to try to tweak it and you know get into immeasurable categories because oftentimes what happens is the perfect metric is very hard to measure and so uh so so then you try very hard to you know like fix that uh and you're spending time working on a metric instead of spending time actually like shipping product and actually improving your usage metrics and your adoption metrics which are the things that actually matter and will feed into your not star metric um so it's very that that aspect is very misunderstood the other thing i'll say related to north star metric is especially for early stage product i often say that you're going to get a lot more signal from the qualitative inputs than you are simply from your not star metric so and i'm not saying just do one or the other but again for early stage products it's really important not just to stare at a metric it's very important to get access to qualitative feedback well you know throughout my career one of the one of the best learnings i've had is when you know i've just uh you know exposed a feedback feedback form for users with one field which is like you know tell us what you think about the product what works what doesn't work whatever like some question to that effect and then i created a morning routine where you know there would be an email system where these uh you know users inputs would show up in my email and so my routine was just to look through those uh qualitative uh pieces of feedback uh and i got so much more user empathy and insight from those than i could ever get from a dashboard so yes you know not star metric is useful to have it's it's useful to create targets against etc but don't try to perfect it and that part i think is very misunderstood along with not taking into account the importance of qualitative inputs before we get into the different types of product leaders speaking of that north star metric and you're advising me in my hypothetical startup journey should i the founder and ceo be the one to determine the north star metric and prioritize product matrix or should that be the responsibility of my cpo head of product oh boy um the the answer to that is do you do you feel competent enough to do it that's the main question uh and if you do as a founder uh then by all means uh define it yourself and you know of course nobody really does it on their own like you're in in a real work setting you're getting feedback from folks anyway but yeah it would be your responsibility if you are fairly competent in this area if you're not very competent in the area uh it is still ultimately your responsibility now you might delegate aspects of it uh to somebody else on your team whether it's the chief product officer or somebody else but ultimately because this is such a you know top level metric that you're going to try to create targets against that you're going to hopefully track on a regular basis you have to be deeply involved and so you know in either case whether you're competent with it or you don't feel highly competent with it your involvement as a founder is extremely necessary especially for an early stage product do you feel competent i'm glad this is a hypothetical discussion shreya um i do want to discuss because you know the show's actually in the you know verticalized way here like 20 products started because i felt that founders didn't know what truly great looked like when hiring great product people and 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 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 yeah so i at this point uh just in the last year i've spoken with more than 50 founders about uh the general area of um oh my product is growing really uh fast and uh i think i need a cpo or a vp product or or my board tells me or my vcs tell me that i should go hire a vp product and delegate uh various aspects of the product to that person and so uh you know they reach out to me and you know sometimes we'll get on a call to discuss it and every single conversation is actually very different and uh because fundamentally if product is what's going to drive your startup success uh you have to create your own script uh around you know uh around what you are looking for and that can only be done if we understand uh how your business is going to be driven forward and what not from those conversations uh i have been able to extract some patterns and so you know one of the patterns is uh the three types of product leaders and they are uh the operator the craftsperson and the visionary uh and um you know when i kind of start sharing you know these names or these labels 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 not so fast what is really important is like there is no one right answer first of all right like uh it really depends but the but the second thing is um that it's important to recognize that it's not like you know a certain person can only be an operator like actually you know highly competent uh senior product leaders they can wear each of these hats so you can think about them as hats instead of categories but still people have a primary hat and that's the hat that makes them most comfortable that's the hat they would rather wear than any other hat so i'll just briefly go into you know what each of these is but the operator is excellent at scaling teams driving cross cross-org alignment and unblocking execution and the operator superpower is communication on the other hand uh one of their challenges is actually original product insight so this is very important to remember like there are often times there are operators who just like have amazing resumes and they've you know scaled companies and products extremely well whether it's larger companies or mid-size companies but despite all that experience i have found that they do not have the ability to come up with really original product insights uh and uh and and this is where often things go wrong with cpo hiring or vp product hiring where sometimes you know your situation is such that you don't do not yet need an operator um eventually almost everybody starts needing an operator in their head of product role but you don't yet need one but you bring somebody on with the expectation that like oh business is going to quadruple at some point and so at some point we're going to need somebody like this so why not bring them early but the problem is now this operator starts operating right instead of helping you get to a better position with your product market fit or ins because to get to a better position with your pmf that requires original product insight uh and and without much help uh the operator is not going to be able to do it on their own uh and so so that's just an example of where like things go wrong 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 yeah so uh you know i personally went through that transition myself uh when i was uh leading connect which is stripe connect which is uh you know a major major business for stripe i i started leading it when uh you know the product was already being used by quite a few of stripe customers the team was only four engineers at the time uh and so it was like 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 and then at some point i 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 just what i'm passionate about 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 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 and so back then i went uh to my manager uh john collison was my manager back then and i said you know i i think in within the next several months i think i need to go back to something that's earlier stage uh and so we ended up actually doing that i went back to uh something that was like very early stage at stripe and helped grow that business which was striped terminal it's in-person payment solution uh so from that experience uh what i learned and having then seen many founders and you know product leaders go through uh similar experiences is that it's definitely post product market fit it is nearly impossible for an operator to solely or mainly uh bring your product to product market fit now it can happen but it's extremely rare and you should not bank on it and but once you hit product market fit and as your product starts scaling and as the demand for it starts growing and as the uh the cross organization complexity increases now what happens is in addition to managing the product you also have a real big organization to manage right and oftentimes it's cross team right like you're not owning everything and that's where operators are tremendously valuable because they are extremely skilled at orchestrating cross-organizational action they're extremely skilled at communication to make sure that everybody is aligned they're fairly skilled at setting targets setting goals and creating a sort of a rhythm in terms of how you launch things in this complex internal environment and so so really that is the point now you know it's not necessarily corresponding to this you know the the cdc or csd or series a or b right like as as you know um there are many kind of like late stage companies uh that are still pre-emp pre-pmf for whatever reason and so so it really depends uh on sort of like what you're trying to do where your product is at what challenges you're facing uh but at some point it becomes very clear that you need an operator and then you need to go find one can you help me out what's the crafts person in terms of like that profile then walk me through that one yes so the craftsperson is excellent at defining products and strategy and mentoring other product people and and their superpower is product insight so if the craftsperson is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning and that skill of translating something high level and ambiguous to actual product actual user experience the pixels uh the customer support experience the interplay of the various things that need to happen to make a product and a business successful they are able to translate that uh really well and so again there's super power is product inside but they're not excellent at uh dealing with large orgs and it's taxes right because any large order comes with all sorts of taxes that you have to deal with they just don't enjoy that right um over my career i i started off as a visionary which we can talk about later uh but then i morphed myself into being a craftsperson and so like you know as organizations started getting large i was just like uncomfortable with managing that like i said i found that boring they love spending time with the team uh and and users okay so now it's interesting operators they love spending time with their peers so other kind of other functional heads and company execs and the board uh whereas you know scraps people absolutely love spending time with users and customers and uh the team and and they they get really excited about product deep dives and oh let's walk through this flow and how can we make it better and that sort of conversation which is very different from a conversation you might have with your cross-functional executive team or with the board for instance and so so that's the craftsperson and is a very essential ingredient in any team whether it's a product leader or even individual product managers you need these people so that you can translate something ambiguous into something concrete if i'm hiring my first cpo head of product whatever we want to name it the senior product hire is that profile the profile i want to go for being the craftsperson that is a reasonable default especially if your early stage startup and say perhaps you know pre-pmf or just about reaching pmf then craftsperson is a fairly good default but there again it depends on your competence as a founder and so particularly again when i go through these kind of sessions with founders uh one of the core things i ask them is like why do you want to hire a product manager whether whether it's at any level an individual contributor or a leader what is it that you want this person to do that you are doing right now because presumably you want to kind of like delegate certain responsibilities so what is it and is it the right thing to delegate sometimes harry the answer is oh i want to delegate a lot of the operational work i want to delegate uh you know the the the figuring out like how the sprints are going to work or figuring out you know how customer support is going to get impacted by this new product feature that we are launching those types of things i want to delegate but i still feel like i need to own uh the core kind of you know customer insight the core product insights uh and some of the definition of the product in those cases uh you may want to bring a sort of like a mid-level or a junior operator type personal person and kind of delicate those operations while still holding on to the visionary and craftsperson hat yourself as a founder so so that is possible but the default uh craftsperson is is a good place to start before we move into the visionary you mentioned like the the cross person struggles with the scaling product team what are the first things to break strass in a scaling product team what are the first signs of things breaking yeah so there are two uh two core things that tend to break across most situations uh one is within the team and that is that as a team grows a large part of your role as a leader becomes one uh you're basically a repeater you just have to keep repeating the same thing and you may repeat it in different ways but you're effectively repeating the same message um and so so you can imagine like if you're managing a team of 20 uh or 25 people uh you can like have a sort of you know personal uh relationship some amount of trust some amount of like just mind meld with a group that's say 20 or 25 but now your team is 50 people uh i'm including engineers designers etc or like the team is 80 people right like there's a team that's kind of building a product that has 80 people it's impossible it's impossible uh to [Music] to create that mind meld right so you need to change your approach which is now instead of relying on one to one or one to few uh interactions you have to rely on one to many interactions right but people don't remember as much as we think they remember right so so you have to keep repeating the vision the goals the strategy etc etc and like that becomes a really important part of your role uh and you know a craftsperson can do this but as the team scales a craftsperson most crafts people don't enjoy that aspect that much because a craftsperson derives energy from being in the product from having intimate conversations about uh uh evolving the product and so it's not the kind of thing that a craftsperson wants to do as a major part of their job and so so that's one thing that kind of starts breaking internally for a craftsperson that makes it harder externally so outside of the org outside of the team what ends up happening is as the business scales there are other parts of the business other departments like sales and support and bde and marketing and various other parts of the organization uh that us begin relying on you uh and you begin relying more on them as well you're no longer kind of self-sufficient and scrappy and so as the company has grown and as your product has grown there are a lot of just like alignment issues there are a lot of dependencies that you need to resolve and at that point you know when you reach a certain scale that becomes an extremely large part of a product leader's role and at that point you are basically just in many many meetings unfortunately and again crafts people can do meetings and they they enjoy meetings but if a craftsperson spends three weeks uh you know uh going to these various alignment meetings they are going to get frustrated right so so that's the part that starts breaking outside of the team uh at which point uh you know if you're a self-aware craftsperson that wants to remain a craftsperson you start thinking oh maybe it's time for me to go back to something more scrappy something more early stage i i totally get you i'm just intrigued because i i'm i'm wondering what visionary is if craftsperson does have the original product inside does have that creativity within them what is the profile of a visionary yeah so a visionary is a very interesting one and like among these profiles the visionary is the most rare or at least the competent visionary is extremely rare the visionary is excellent at big picture thinking and inventing what's next and their superpower being that they can see what others cannot see and it would seem like this is uh you know this should be a uh you know a fairly common trait but again a competent visionary is extremely rare um and so what's the difference the difference between a competent and an incompetent visionary given so much of their beliefs of future held what's the difference 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 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 and and it's my favorite of their they have really great leadership principles this one's my favorite because this is so misunderstood because you know the the 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 follow a process yeah and uh make sure it's a good process make sure you set okrs make sure you 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 100 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 luxury to be able to take a product from 20 to 60 right and and and that could have only happened with the vision of a visionary and the craft of a craftsperson uh who are right a lot right so uh so now sometimes it gets confusing like okay so but what's the difference between a visionary and a craftsperson one of the challenges with the visionary is uh that a visionary finds it difficult to translate that big vision which by the way again by definition very few people can see that vision even many crafts people cannot see that big vision a visionary finds it hard to translate that to concrete product steps like okay so i want to do this i want to revolutionize i don't know spreadsheets right like and and and i have a certain certain vision in my head of how that is supposed to happen uh but what is the first step i take what is the next step i take and what's the step after that uh that is where a visionary uh works very well with a craftsperson because a craftsperson can kind of translate that into concrete steps along the way uh and again there are many visionaries who are also crafts people right so uh and i've worked with many uh such folks uh and so so they can do that job but only to a point like like you know these really great visionaries they often find it hard not always but they often find it hard uh without the support of craftspeople and operators to do it consistently can i ask should the founder not be the visionary and the cpo not be the craftsperson uh 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 sub-optimal in the world that you want to uh you want to fix and so so oftentimes uh founders end up being uh that kind of visionary archetype and on founding teams i've found that it's usually you know one of the founders that's the visionary and perhaps you know there's another founder that's more like an operator and maybe even a third that's more like a craftsperson and i'm not saying it has to be that kind of composition uh but typically you know in like at this point i've kind of advised uh you know 100 plus companies just in the past two years on various topics and i found that like usually there's one founder who's the core visionary who who then takes ownership of the product early on naturally and kind of like you know sometimes where's 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 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 and the visionary has a very clear view of the future but being responsible people they also now take into account user and customer feedback and that can get confusing at times um even if it's not confusing for them they may find it hard to kind of like you know bring the team along on like okay given all this kind of conflicting feedback and this plethora of uh you know ways in which we can take the product here's what we're going to do is step one step to step three here's how we're going to actually build out the product uh these are the flows that matter these are the flows that don't matter that's when whether it's a cpa or a vp product or even a director of product or an individual product manager a craftsperson becomes a great asset for a visionary how do you determine when to listen to customer feedback versus when to progress with expected and planned roadmap and ignore it tough question 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 they are highly customer driven 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 and and sometimes that can be the right answer 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 and so so that works but i have found that it's very important to you know ground what you do in terms of a core strategy so the strategy becomes a the piece uh the artifact uh the guideline for when you listen to customers and when you don't listen to customers 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 a striper 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 its own solution like that and one of the challenges that we faced is that we were competing against very very powerful incumbents and again because point of sale payments had been around for a long time there was a massive gap that we had to fill in terms of just basic table stakes features uh like for instance to give you a concrete example um you know when you are accepting payments uh say with a card like physical card you're accepting payments um you know for events uh it is complicated because sometimes the event might be occurring so it's a concert or something else the event might be occurring in a place where there's no network access okay so how do you do that online auth authorization that uh this card is good for the 100 ticket that it's purchasing or uh whatever goods that they're purchasing at the concert you can't uh and so uh so there is a solution to that uh which is offline mode uh for for payment uh payment terminals and so uh you know as we and it's not easy to build that so as we were trying to get stripe terminal to get adoption we would get all these feature requests right which is like oh we need offline mode uh and we need uh you know all sorts of other kind of security features or all sorts of uh you know additional customization features like for instance the point of sale terminal that you see uh the payment terminal that you see at the grocery store is highly customized it has the branding various other things and so customers were asking us for all of these features uh and our team was very tiny uh if we were to just build all of these what i call table stakes features it would just take us five years just to even just basically meet the table stakes uh and and and we could have done that we could have done that but at the end of those five years you end up with a product that's just a poor substitute for one of the incumbent products that have had a 10 year 15-year lead on you right so so yes i can follow what customers are saying and i can launch these features that'll make them happy but now i have a product that's hardly differentiated right so so in this situation what we decided to do was something different we said you know what we are actually going to uh i have this framework called uh um you know i haven't talked much about it or in at all about it like sort of externally so this will be the first time um i have this framework called the btd framework which is essentially for any sort of like important aspect of your product uh you decide whether you want to come in below table stakes that is b um you decide if you want to come in at table sticks that is t or you decide you you actually want to differentiate that is above table sticks above what what is expected and that's differentiation um so you know just use btd right which is be intentful about certain customer requests and say you know what for this type of request we are going to come in below table stakes right so that's your b in other cases you may decide oh i want to meet table stakes and in some other cases you may go well beyond what customers are saying or build something entirely different that customers uh aren't even asking for which is a lot of what we ended up doing with terminal um and so so that that it becomes the basis of your strategy and that's why i think being strategy driven is very important ask you a hard question when angel investing and advising companies today when you look at that framework which are you most attracted to and do you find most compelling as a product leader product investor which one are you most attracted to today a hard question um in terms of you know categories what i get most attracted to or categories of like companies or founders it is below table or above when you look at those like i like ones which um actually come in above like i hate it when we have to catch up to incumbent feature sets and then we assume that they're just going to stagnate and they're never going to stagnate you're just always going to be behind actually i'd rather say hey you know what the current poses may have all these features but it we're gonna make this feature that plays iron maiden when you buy anything um and it's gonna be a wow consumer experience so we're gonna come in like above but kind of except below in other areas do you see what i mean do you have a preference when you're investing for where they insert themselves on that feature insertion point or product in session you know uh what uh what i found uh most interesting is and i think this generally works for most products and the new products and new startups is when you are entering a fairly crowded space where maybe there's a very powerful incumbent um the customer segment you target becomes really important because what you want to do is you want to target [Music] a kind of customer a segment of customer uh that the incumbent is not doing a very good job of satisfying and for that target customer then you determine uh okay what are their unfulfilled needs right so yes the incumbent has a bunch of like features and like they're doing well etc but you will find pockets of customers and segments these segments that are highly dissatisfied and and so that's a good strategy for a new product where you find those pockets of customer segments that are highly dissatisfied with certain features because they're not important for the incumbent across its customer base but they're very important for this specific segment and that's where i like companies that are that are very clear on targeting certain segments and then creating highly differentiated experiences for them and when you do that and this is essentially what we did with stripe terminal is when you target a specific segment and meet their unfulfilled needs in surprising ways and you go way above table stakes you differentiate they will give you a lot of leeway they will be willing to live without a bunch of other conventional table stakes because your product performs so well on their core use case where the alternatives are not that great frankly for them that they will be willing to live with some pain they'll give you a lot of you know just leeway to catch up on some of the table sticks 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 yeah you know um i think the the core thing that uh perhaps um you know and this this one's very obvious in hindsight but like you know previously i when i started angel investing uh i i was very attracted to the idea and again being sort of like a product idea person a craftsperson like you know i was like this needs to exist in the world and so so i'm very excited about this i want to invest in this i want to support this founder and whatnot and what i realized over time is uh that that isn't unnecessary 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 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 uh if that is true and that's the bar i apply for advising as well right like because uh i i want to keep the number of companies to a manageable size and so one of the core things i look at is is this person one of the most capable persons i've ever come across and are they do i think that they will be able to create and hire a top-notch team so if you look back at the collisions in particular can i ask what profile would you put them in in terms of craftsperson visionary or operator they're different very different people so yeah so uh i mean they're both brilliant people so it is a tough question it's hard to kind of like you know put them in one box and not that these archetypes are about boxes but my assessment would be that patrick is very much a visionary craftsperson [Music] type person so you know every time i've interacted with him and i learned a lot from you know about product uh from interacting with him um that's been the conversation is is the visionary craftsperson uh mindset uh which is what is the big idea here right like and how are we gonna differentiate uh and uh how how are we gonna get user adoption uh and also uh you know how do we get like the the product details right uh how do we surprise users uh how do we make uh you know how do we further the brand uh you know how is this brand aligned those types of things um uh were a constant kind of you know um aspect of uh my interactions with patrick uh so he would be that visionary uh craftsperson archetype uh john is interesting uh in that like you know he is he's one of the rare people who can do i think who kind of can do and i've seen him do all three really well uh in fact there were many times when like john was managing certain teams on an interim basis uh at stripe that like you know he clearly had never managed that type of team whether it's sales or something else uh before but he was able to do it really well uh so i think john is harder for me uh because i've seen him kind of do each of these three uh and and not just do each of these three but like actually uh just uh enjoy doing it uh at least from the way i was looking at it i i totally agree with you on john being a unique mixture of all three um oh yeah i i totally agree with you that final one and it's a bit random how important is time to value in a customer experience often i speak to fans like oh we need to reduce the time to value it needs to be quicker it needs to be more uh kind of emotive and valuable faster and sometimes i think yes and sometimes i think you have to go slow to go fast and you do need to connect your data sources your different accounts whatever the process is how do you think about time to value when advising companies today yeah i think it goes back to what is the core customer motivation and how strong is that core customer motivation okay so and i think this is something that uh very few teams do on a consistent basis um and in fact some of the companies advise like i i love to see after i've advised them for a while where like they'll run some products by me uh and uh they will actually start with uh okay so the core customer motivation or the core user motivation we think is x and so in order to help the customer fulfill that motivation here's the product so this lead with the motivation rather than leading with the the actual product experience and so i love that now just expanding on that a bit when the core customer motivation is extremely high you can afford to lend in that time to value right but when the core customer motivation is not that high and and particularly um you have to remember it's not just about what they hope to accomplish it's also about what alternatives they have so the alternatives factor into the degree of motivation uh around fulfilling uh that motivation with your product so if i have a lot of alternatives including the alternative of continuing with the tool uh or the app that i already use that i'm used to using which may be sub-optimal then my core customer my core motivation as a customer is not going to be that high uh and so then in that case you've got to show me the value sooner right so and let's take b2b because i just love this question and there's so much like uh so much value to be created by companies and startups if they understand this consistently is you take some b2b products uh and uh you know my observation is some b2b products are what i call mandate products and what i mean by mandate products is that when an executive gets hired in a specific role that executive makes it a company mandate and certainly a mandate for himself or herself to roll out that product across the organization or across the department so that's a mandate product okay what's an example of a mandate product workday is a great example of a mandate product which is in you know many parts of the world and certainly in the us if you are a chief people officer that has joined uh you know or you know vp of human resources that just joined a scaling company say more than 500 or a thousand people often a lot of the work is happening in spreadsheets or some tools and you come in and the first thing you say is we're going to roll out workday right and so so workday becomes a mandate product if you're a cfo uh uh you know and you if you're hired as the first cfo you'll come in and you will likely uh uh roll out netsuite as the mandate product uh and and there are many other examples like that if you're the chief data officer or whatever uh but the point here is that uh a mandate product usually has a very long time to value because you have to kind of you know roll it out across the organization uh you have to train people you have to you know it's like a six month process sometimes even a year-long process for instance uh to roll out netsuite within an organization uh so that time to value is very long but the the the observation here is that the credibility has already been established which is like you cannot go wrong if you roll out this product within the organization right you will not be fired in fact you might get promoted for rolling this out because you'll create a whole lot of cost savings or you'll create a whole lot of efficiencies and that's what you want to do as a new executive right within the company is to start showing how you are being a lot more effective than the com then then the company was be before you so uh so in those situations like the marketing and the branding also matters the positioning matters right uh so when your positioning is very unique um and very strong you can have a much longer time to value as well so again it's like you know i i don't think there's one right answer and sometimes on twitter or other places people will just say this is the one way to do it and it's like no no you you have to be really thoughtful and intentional about these things the problem i have with you is um i could talk to you all day about a lot of these things because i have a lot of like product questions where i've thought them for a long time and needed your wisdom um but uh we we can do a part two in in another segment i want to do a quick fire round now where i say a short statement and then you give me your immediate thoughts does that sound okay all right let's do it okay so what in the realm of product have you changed your mind on recently again the role of metrics how so and it's basically what i shared earlier uh like which is like there isn't one type of metric there are actually you know several types of metrics and you have to really decide what type of metrics are really important for you right now uh versus what will become important later what are the biggest mistakes you see founders make when hiring their first product hires they they over emphasize background resume titles and companies that the executive has worked at uh and they often ignore their instinct about the the executive during the interview process and then unfortunately end up regretting the choice six months 12 months down the road what one piece of advice would you give to a new product leader starting a new role today first focus on understanding the customer and the domain extremely well don't pressure yourself into creating value within the first 30 days or even the 6 for 60 days because you are playing the long game and also build start building relationships and strong relationships across the organization but especially with your team from day one do not postpone that as a product leader yourself a bit of self-reflection what was your biggest strength and what was your biggest weakness biggest strength was uh product sense the ability to uh often be right about what product is uh going to work uh biggest weakness uh was about making the broad organization aware about all the progress that my team and my product was making final one what recent company product strategy have you been most impressed by hmm you know there's a company uh that's based out of india it's called a lead school and i've been advising them for more than a year and um their their product strategy is uh is just really exciting for me because what they're doing is they're bringing high quality really high quality school k k through 12 education to smaller towns and smaller cities so not the big metropolitan areas in india but the smaller towns and smaller cities in india where what they want to do is they want to create greater parity of the quality of education you can get being part of you know living in a smaller town as a child in in india and canada and they are doing that via a combination of curriculum uh technology uh and uh uh operations to support the curriculum and technology and so it's been great to sort of like watch them kind of not just formulate that strategy but also execute on it over the last year sure i knew this would be a great show but this is like shows like this make me really appreciate why i love what i do so much so thank you so much for joining me thank you for putting up with my basic questions i'm so enjoyed having you on yeah likewise harry this was a blast and uh looking forward to our next chat