Dan Pupius, CEO and Co-Founder of Range, Part One
Published 3/29/2021
Today's guest is Dan Pupius, CEO and co-founder of Range. Dan cares deeply about creating products that make healthy and sustainable workplaces a common occurrence. We talk in depth about designing constraints and opinions into products with the long term in mind. Don't miss the next episode - subscribe today!
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Transcript (Generated by OpenAI Whisper)
Hey everyone, welcome to today's episode of Developer Tea. My name is Jonathan Cottrell. In today's episode, we have a discussion with a founder and CEO, Dan Pupias, who created Range to help teams work better together. Now, before I lose you on that, it really is what Dan cares about. He wants teams to work better together, and he wants to create psychologically safe environments, and he has been hands-on designing this product to help teams do just that. And Range is a very simple application at the time of the recording of this episode, but as we discuss in the episode, Range is driven more by purpose than it is by specific features. I'm excited to talk with Dan, so let's get straight into the interview with Dan Pupias. Dan, welcome to Developer Tea. Hi. I'm excited to have you on the show, and I want to kind of kick off this episode with a question that sometimes I leave until the end. It's one of the kind of the two main questions that I like to ask at the end, but I think you might have some really interesting answers to these questions. So the first question I want to ask you is, what do you wish more people would ask you about? Yeah, when you told me you were going to ask this, I actually kind of struggled, because I'm often just curious to talk about whatever people are interested in. I think the answer would be is like the human side of engineering, and thinking about the human systems and the organization design. I think that's super fascinating, and it's often more challenging than the technical aspects of the work. I'm going to dig in on this, because... I agree with you. And I think the specifics of how this plays out is really interesting. We're going to dig into it in just a second. But first, I want to take a minute and let you introduce yourself. I guess we jumped right over that. Can you tell listeners who you are and a little bit about Range? Yeah. So my name is Dan Pupias, co-founder and CEO of Range. And we started Range a few years ago with the goal of helping teams work better together. We believe that there needs to be a balance between the team and the team itself. And that's what we're doing. We're building a team. We're building a team. We're building a team. We're building a team. We're building a team. We're building a team. We're building a team. We're building a team. We're building a team. productivity and we want organizations to aspire to create these environments where people work, where everyone feels empowered and engaged. And we do actually feel that software has a role to play in that since software facilitates so many of the work processes. So we started with asynchronous communication as a way of providing foundation for teamwork and today Range at its core is a check-in tool. So it's a simple status update that people do usually daily. They show their plan for the day and what they've got done, but also how they're feeling. So it's a little bit like a standup, but we integrate with all the tools that you use. So it's really easy. It integrates with your workflow and then also creates a lot more transparency into the work stream. So yeah, that's it today. And we, people use it to, you know, teams like Twitter and Airbnb and they use it to keep, stay connected and you know, know what's happening across the team. I love the way you describe your team. Your product as what it is today, because it does two things. One, it lets people know that, Hey, you know what, this is not, we didn't set out with this grand vision to create a standup thing. That's what you've discovered over time is, is an effective tool. And then also you leave space to change it in the future. Am I right about that? Yeah, totally. We, you can't boil the ocean and it's a big mission and we, we want to help facilitate. All work processes, um, in a way that actually makes work more engaging. And pushes authority and decision-making out to the edges of the organization, but we needed to start somewhere. So we started with this, this check-in, um, bit like a virtual standup. And the reason we liked that was it was a regular habit. It was a behavior that people were already doing that we could piggyback on. And then it is actually at the intersection of work. It's about what you've done and what you're working on, but then also the relationships between the team. So it was an opportunity to bridge that gap between the productivity and the team effectiveness. Yeah. I love it. I love the, the idea that, you know, our tools that we use every day, which developers are, we're very well known for loving our tooling, um, and for also hating our tooling, but that's a different story, right? Um, I, you know, I'm, I'm curious, what do you see as, I guess I'm just very interested in this idea of making our tooling one step more human. Um, and so what do you see as some of the, the major downfall? What do you see as some of the major problems that you see in that industry right now? Um, I'd rather talk about the opportunity versus the problems, but I guess some of the problems are not thinking around how the software gets used or the implications. Um, and I think part of the problem with the software is that it's not going to be able to do anything about the impact of the software. Because you know, you're going to have to keep going. You're going to have to keep going. You're going to have to keep going. You're going to have to keep going. And so you can imagine some, like a productivity tool that tracks what people are working on. And it sounds good in theory, but then it ends up being a surveillance tool, which actually creates an environment that's not psychologically safe. So you can think about these unintended consequences. So I think the positive spin, I would say, is that, you know, Churchill said that we build the buildings thereafter they build us. And I think it's the same for software. We build the software, but then the software changes how we behave and how we interact with people. So we have to think about software development intentionally, about how people are going to use it and how people are going to relate to each other. There's an anecdote from my time at Google that I've mentioned a few times around code of you. So I worked on this library, JavaScript library that was used across the company. And to start with, the internal code of you tool just had your LDAP name. So it didn't even show your full name. It was just some arbitrary string. And I'd get a code of you. And I'd often have this visceral hit of anger and frustration as soon as the code of you dropped. And then if I did the code of you, I'd end up being pretty harsh and aggressive. And I got some feedback that I was scary to send code of you to. So I realized that if I went to the team directory and looked at people's profile photo and what team they worked on and what their name, then I would empathize more with them as a human. And then I'd come back to the code of you and be much more reasonable. And I'd be able to see what they were doing and what they were doing in my relation with in my review feedback. So I think that's the role software has to play is that it can humanize the recipient and it can help you give empathy into the people you're communicating with and the others in the system. And if you don't have that mentality at the outset, you can end up creating systems that can create anxiety and create tension between people where it doesn't really need to exist. This is such an interesting concept. Yeah. Yeah. It's such an interesting concept to me because I think I've encountered so many software engineers who, when they think about tooling, they think about it purely as a means to an end. And this isn't just engineers, by the way. But engineers seem to have a particular lean in this direction because so much of what we deal with as engineers is trying to get behind the pretty layers and into more the core. And so I think we... We often think about it as a means to an end. But actually, when you look at the behaviors, it's much more like a framing device. We have some bit of information that needs to be framed. And how it gets framed, the context that it's in, you know, what kind of meta information is included can totally change what you perceive. And I think you just... That anecdote you just gave is a perfect example of this. It's the same information at the core, right? That the code didn't change when you went and looked. The picture, the directory. But your perception of the code was now contextualized a little bit differently. And so I wonder, you know, what do you think of this concept of technology or tooling as a frame rather than purely as a tool? Yeah, I totally agree. So I kind of see software as architecture. And architecture shapes our behavior. And if you think about driving as an analogy, your goal is to get from A to B. And the end is being at B. But how you get there is very critical. And the architecture shapes your driving behavior. So if you have speed bumps or road signs, that will change how you drive. And if you actually remove line markings, it's been shown that people will slow down. Or if you make the street cobbled, that will change driving behavior. So the means are as important as the ends. Because it actually shapes how the journey occurs. And then that can actually change where you end off as well. So I think the software is very similar. And you have to think about the process as well as the outcome. Yeah, this is such an interesting point you make. Because I actually just read a book called Chatter. It just came out not too long ago. And in the book, one of the things they discuss is the effect of our environment on our well-being. In ways that we wouldn't necessarily intuitively expect. So, of course. For example, being around green spaces. This is a very well-studied effect. And unfortunately, not very well-known in common culture. But green spaces can have a pretty dramatic effect on your well-being and on your cognition. And a whole host of other things. Biomarkers, etc. And so what you're saying to me. And I was just thinking as you were saying it. The A to B. The destination didn't necessarily change. But you did. The person on the journey changed. And perhaps the people that are on the other end of that will change as well. And so it seems like a lot of our jobs as software engineering managers. Is to build environments rather than software. To build an environment where good software can be grown. Very similar to kind of cultivating. Yeah. A garden. Do you see the role of the manager to be similar to that? Yeah, totally. And I've used the gardener analogy before. And I think to tie this back to one of your previous comments. Is that there really aren't ends. There are only means. And often we don't really know where exactly we want to end up. We know if we're a gardener. We don't know exactly what the tree is going to look like. And we just know that we want a Japanese maple that looks pretty. And has blooms in the summer. And we cultivate it and set the environment for it to grow. And for it to be successful. And I think that's the same with teams. We have a vision or an idea about the destination. But we don't exactly know where it is. And then it's very much about the journey. And the journey becomes exploratory. And then I mean, it's stretching the analogy a little bit. But making sure that everyone who is on the team. And who is working towards that destination. That you get their perspectives. And that they're able to contribute as much as they can. I think that was one of the realizations I had working with Ev at Medium. Was that he's a big product visionary. But he didn't have an exact picture of what he wanted to be built. He had a feeling of what it would be like if we succeed. And then we had to build an organization. Which helped him explore the path to that vision. And to realize what the destination really was. Versus setting a line in the sand that we have to walk towards. Yeah, when you said that you wanted a Japanese maple. In my head, I immediately translated that to. Well, actually what you want is the feeling of looking at a Japanese maple. There could be many things that could get you there. And I think often the biggest mistake that I see. Both in individual contributors. But also in other managers. Is that they'll look at a request for a Japanese maple. And instead of abstracting upward to. Well, what you want is the feeling of looking at the Japanese maple. They'll go down even further. And they'll say, well, okay. So we want this specific type of Japanese maple. And we need this specific type of Japanese maple. And we need this specific type of Japanese maple. And we need this specific kind of soil. And we need these specific lighting conditions. And it continues to add more and more kind of imposition to the work. And that creates this kind of system of inflexibility. Whereas if you were to abstract upward as a manager. You're kind of building in flexibility to the process. Because there's many pathways. of you know honing in on only a singular pathway yeah and i think i think the other thing is that um especially when you're talking about customers and product is that they ask for something that they think solves their needs but so you have to dig a layer underneath like what is the need that they they actually have and then how might you solve that and often often they don't have the best idea of of what would actually serve them and i think it was it was henry ford which was people would ask for a faster horse they didn't ask for a car um so you have to get you have to get underneath the the request and really empathize with their their needs i want to ask you a question on this because i've been thinking a lot about it lately and you know i i talked to my colleagues i talked to my family even my wife is a product owner herself and i i i continue to kind of push this same point which is you ask about the underlying need right you say okay you're saying you want this thing but what is it that you want to do with this thing or what is it that you need out of it and you can continue with that chain of okay but why do you want that right you want you know you want this sales tool so that you can increase your throughput and you want to increase your throughput because you believe it's going to increase your revenue there is a point where you can ask questions that will mayensionijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijijij Everyone knows about the hierarchy of needs. In his actual books, he doesn't talk about them as being a strict hierarchy. But if needs aren't satisfied, if lower-level needs aren't satisfied, then you can't hope to achieve the high-level needs. So in an organizational context, if people don't feel psychologically safe or don't have some of their basic emotional and psychological needs taken care of, then they're never going to be able to take risks or perform to their full capabilities. So I mean, I think, yeah, it's definitely tricky and it is a judgment call. And then I think you have to also look at, is this system-wide or is this individual? But I think you start just answering the question or asking the question of, what do these people need? And then digging as deep as you can. In the context of range, we think about that a lot, which is that we're building at what, like you described it as a stand-up tool. But I think when we look at the stand-up tool, we look at what people need to be effective. And we've really drilled it down to three fundamental pillars, which is transparency, purpose, and belonging. So knowledge is power. And in regressive organizations, information is hidden in order to consolidate power. But often it's not explicitly hidden. It's just not publicly available. Or it's not in a format that you can easily access. So if we can create more transparency around what's happening in the organization and artifacts that are being produced, like documents and designs and decks, then people have more knowledge. And then they have more context. And then they're able to better make decisions themselves. And then if you make decisions yourself, you're empowered. Whereas if you don't have that information, then you have to rely on other people. So transparency is one of the things we think about in the context of range. And then purpose is, you know, burnout is a big topic at the moment. But one of the biggest causes of burnout is not really understanding how your work fits into the bigger picture. So if you can help, if someone can understand on a day-to-day basis that this work is important, even if it feels rote and repetitive, then that can really help them feel more engaged in their work. And then the final piece is belonging. And that's the precursor to psychological safety. So micro moments of vulnerability help you trust the people around you. Once you trust people, you feel a sense of belonging. And then that belonging is what, Yeah. creates the environment of psychological safety. And then you can take risks and push yourself and challenge yourself in ways that wouldn't be possible if you were, if you didn't have that sense of safety. Yeah. You mentioned something so interesting a moment ago about how it's not necessarily hidden, but it's not visible either. It's this idea that it's almost accidentally obscured. Yeah. Yeah, totally. It's often, it's not intentional, but then say that you got, you started hearing about a project that was going on and you didn't know about it. And if you are not safe, like if you're in a psychologically safe environment, you would just say, hey, what's going on with this project? But if you weren't psychologically safe, you'd be like, oh, is there a reason that I'm not being told about this project? And maybe they don't trust me, or maybe I'm not seen as important. And you start writing these stories and then that compounds. And that makes you feel less safe. And then that, then you show up in meetings differently. So if you can work in the open and provide a lot of transparency and all the work that's happening in the organization, then people can, a lot of these anxieties can be calmed. We'll get right back to my interview with Dan Pupias right after we talk about today's sponsor, Square. 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But the natural way to fill in the blank might be there's a reason that I don't know about it, and it's because of a shortcoming that I have. Yeah, I mean, I think it comes down to trust. And trust has a half-life. It degrades. Yeah. So when you're looking at groups, you have to have these renewals, these belonging cues that make you remember that you're all on the same team and that you're not going to attack each other and steal each other's food. And it goes back to very basic instincts from earlier in our evolutionary history. So this, again, ties to good work practices, where if you can create these micro moments of vulnerability every day, then you're basically renewing the belonging cues that create trust. And then you're less likely to write those stories. Yeah. And those stories are so often implicit. They're beliefs that we almost don't even realize that we have. Would you agree with that? Yeah, I think it's survival instincts. Yeah. So I think it comes down to some very base evolutionary needs. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. combative and conflict can be not healthy. Healthy conflict is dialectic of perspectives. Unhealthy conflict can easily slip into the picture. What I find so fascinating about this discussion that we're having right now, if anybody who's listening to this, myself included, has gone to any kind of therapy, particularly if you've ever gone through anything like CBT, cognitive behavioral therapy, these are the kinds of things that are discussed. The idea that we catastrophize, for example. But most of the time, the prescription is to think through and try to judge from the outside looking in. Imagine that you're an impartial third party looking at your own scenario. I think the issue that we face is we can't ask people to approach their work with that level of intentional self-awareness without also meeting them where they are. In other words, creating the environment, like you're saying, building our tooling in a way that respects that underlying survival instinct and tries to design an environment that doesn't fall, you know, prey to these baser, unproductive instincts. Yeah, totally. Yeah. It's not an individual problem. It's a systems problem. And it's, yeah, it's absolutely about the environment and making it so people can show up. And, I mean, slightly related, but one of the things that's been very influential for me is the work of Robert Keegan out of Harvard Business School and cognitive development levels. And him and Lisa Leahy did a bunch of research into adult cognitive development and identified these milestones, which, which how people make meaning. And the, and over the course of a day, you are fluctuating between these different levels. So it's not like a purely linear progression, but the, the base level is just instinctual behavior. So if you're out on the street and you get attacked by a robber, you're going to have an instinctual response. And that, that is, you know, contextually appropriate and healthy, but you don't want to instinctual response in the workplace because then that, that, that, that leads to behavior that is just not appropriate. The next level up is a very egocentric view of the world, where it's, you know, very right and wrong, black and white. And that's where you start to think that these people might be out to get you, or they're hiding information. And it's, it's a very, so it's me-centric view of the world. And then the, the level above that is, your mind literally makes meaning through the, through the group dynamic. So it's, it's, like a socialized self and you think about yourself in the context of the group and that's that's where you have these sort of more egalitarian um like feelings and um you know altruism and um and that's that's that's you know if you're at the pub with a group of friends that's you're going to be in that level the socialized level so if you can create that environment at work um that's just a much stronger foundation to to have creative discourse whereas if everyone's in these low levels of either the egocentric self or the um instinctive self they're going to be very reactive and not thinking through things from a kind of like a group what's best for the group yeah that so i i wonder when when you're saying that that this kind of the highest functioning self is one that's in a in a social atmosphere or a social kind of the social identity or group identity there's actually levels above that which um oh go ahead so the levels above are actually when you then detach your ego then detaches from the group and you think more institutionally so the group the the socialized mind has a bunch of strengths but it can also it has some downfalls like group think or being in group out group um but the the the next level is where you think much more institutionally and um is it i mean it's a interesting progression um and it's been very useful for me in sort of analyzing and diagnosing organizational behaviors can you give an example of the institutional thinking how how might that play out in in a workplace um so honestly that's where the most creativity happens and um and that's where you you can avoid some of the the downfalls of the in-group out-group and when you and you and you think it's sort of from a perspective that's slightly decoupled um and depersonalized so you don't think of um oh the marketing team are idiots because you know they're they're not doing anything xyz or the infrastructure team are letting us down you think more of um the the system and the perspectives and that's where empathy occurs and understanding these needs of of different groups um so robert keegan talks about that as the the institutional self versus the um versus the socialized self very interesting i i wonder if they there's there's two questions that come to mind when you when you describe these two uh these these different selves um or or layers of identity um the first question that comes to mind is do you think there's a time or do you think it's possible for that institutional kind of detached uh self to to get confused with the egocentric self uh especially if you if you're aware of this framework i can imagine that happening um and the the second question that comes to mind is you know is there there's it seems that there might be a suppression of the self-awareness of the individualism or um because you're kind of graduating beyond that egocentrism how does that kind of combine with respect for our individual differences and that kind of mindset yeah i mean that that kind of what you're talking about there at the end that's that's the kind of the definition of the moving into the institutional space where um it's where you you have a very clear sense of identity identity and you're able to kind of understand the the the the the the the the but in relation to others um i see so if you think about beginning to develop respect for them rather than antagonism yeah whereas like think of like um like football supporters um their identity their identity is so tightly linked to the group um and like like a lot of bad things can happen without you know that's where the football violence occurred back in the uk and um people get you know i remember being in manchester and there's like red shirts blue shirts and you know you'd hate the people who were in the group and they were like you know you're not going to do anything with you know you're not going to do anything with people on the other side because it's like so closely linked to the group so yeah so moving into these higher levels is that you you have this sort of sense of self-authorship and self-identity but in relation to groups and um the like the broader system uh-huh that makes sense yeah so i think that yeah so when we talk about you know going back to the environment we want to create an environment which is defaults to this sort of socialized mindset where people feel like they're all in the same group and on the same team that they don't have to worry about you know what they're doing and you know threats and um um and like othering but then that creates the foundation for jumping into these higher higher cognitive states where you can have um healthy conflict and um you can integrate people's perspectives and and and and be more creative yeah yeah this so i this makes me kind of go back to range and wonder you know how what are some practical things that you've done in designing building this software that integrates some of these philosophies that we've been talking about i mean a lot of this stuff is is very much i imagine nuanced and small decisions can have cascading effects so i'm curious are there any practical ones that you you know are particularly proud of or were really intentional decisions on your part yeah at this at this stage it's it seems simple and there's a few other products that are doing and that are now doing similar things but um you may have heard of evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution evolution So choosing it is interesting. And then when you share it, there's actually some depersonalization in the sharing where you can share this emoji, which actually might seem silly, but it's less risky than at the start of a meeting saying, I'm really tired because my daughter wasn't sleeping or I'm feeling really anxious today because I've got so many things on my plate. So you can just use a grimace emoji or a sleepy emoji and it actually makes it much easier to share how you're doing. And then the rest of your team have that perspective. And we often hear from customers where you have a manager or a teammate who didn't know that someone on their team was struggling. But this emoji then allows you to have a conversation. So instead of saying, why are you tired? Or you seem stressed, what's going on? You can say, hey, what's the story behind the grimacing emoji? Or I noticed you were yellow today. Is there anything I can do to help? And actually it makes it feel less judgmental and more safe. So that's one of the things that we did early on, which many people thought was silly, but has been surprisingly impactful for both our own team and our customers. Yeah, this is a practice that I, in a totally different way, have implemented in my one-on-ones as well as in our stand-ups as much as I can. And the way that we practice it is similarly very definitive and normalizing. I ask for a kind of a one-to-one, one-to-seven, how are you doing? Where seven is the best possible, and then one is you're doing quite awful. And what I've found is the number becomes important for a couple of reasons. One, it forces people to take what is otherwise a non-quantitative internal feeling and try to balance it and figure out all things considered. And so this can actually, I've seen it actually help improve people's moods just on its own because they say internally, I can kind of see the wheels turning and I've done it for myself as well, where I had, you know, somebody cut me off in traffic. And we know this from research that small bad things can have a disproportionately negative effect on your day, on your mood. But then I start to take into account how I'm doing in other areas. And once I assign, something to it, when I say, okay, you know, I really have to try to assign a real number to this. I realize that I'm actually doing better than I thought I was. And it's kind of this weird observational sense that I get that I otherwise wouldn't have had, that I would just kind of, I'm feeling my feelings otherwise, but now I'm kind of observing my feelings. And it's all happening because somebody's saying, what number are you? Yeah, it's essentially a mindfulness exercise where you check in with yourself and you get out of autopilot. And we're so often, we're not conscious of like how we're feeling or how our body is or the tension. And all that then affects how we communicate with each other and how we collaborate. So if you can bring some self-awareness to how you're actually feeling and like what tension you're carrying, and then that can actually calm some of the transferences as the, the psychological term, the transferences that are coming from those like feelings. So yeah, it's very, very, very important. I'm curious what got you interested in this deeply psychology-based understanding of product. Was there a moment in time or was there an experience that you had or a book that you read or something where you said, wow, this is really the core of what I care about. Yeah. Yeah. It was, so I did this. So I got really interested in, in how teams work as the starting point and, and rethinking management structures to really help people feel empowered and not, you know, and be more like these like sports teams where, where everyone is, is really, is really, is really, is really, is really, is really, is really, is really, is really, is really, is really, is, is, is playing and everything's dynamic. And in the moment you're not being directed by someone. So everyone feels like part of the game. And that got me into, they think about the conditions and like group dynamics and that led to the psychology. And then it was a, a leadership training program that really opened my eyes and it kinda just answered a bunch of questions and around like how people behave and why, why things unfold and, in a really just like eye-opening way. So that was like the, and I got really interested in that. And this, and that was, that leadership training program introduced me to the concept of psychological transference. And then I, so I read a bunch about that and how therapists use it in the therapeutic process. And it's just like a really interesting empathy exercise and trying to, the meaning of our communication is so much of it is subverbal and so much of it is actually the, is interpreted by the recipient. And that dynamic is just like super fascinating. And then you can see when it goes wrong, it kind of just like snowballs and all these reasonable, seemingly reasonable people are making rash decisions and behaving really inappropriately. So just like understanding the dynamics became just very interesting to me. Thanks so much for listening to Two-Ton. Thank you. Thanks for chatting in Discord, which is a fantastic platform, by the way. Head over to developertea.com slash Discord. You can join there. Thanks so much for listening. And until next time, enjoy your tea.