Using Jobs to Be Done to Build a Whiteboard That Does Math: A Conversation with Matt Wensing, Founder of Summit
Michele chats with Matt Wensing, founder of Summit (and exited founder of RiskPulse).
Michele Hansen 0:00
Hey, welcome back to software social, I am super excited to have a guest with me this week. It is Matt wensing, who is founder of Summit, which is a tool for financial modeling. Previously, he was founder of risk pulse, which was acquired in 2019, which was an enterprise SAS. I'm also the co host of out of beta. Matt, welcome. Thanks, Michelle.
Matt Wensing 0:31
I'm really excited to be here, too. I'm a listener. And I just love it. So this is fun.
Michele Hansen 0:37
So I have been wanting to talk to you for a really long time. And there is one tweet that you sent out in particular, that made me really want to talk to you. So in January, you tweeted out some notes you had taken from customer research that you did for Summit. And you were working with what the jobs to be done world calls the forces diagram, which is basically this diagram we use to show the different pushes and pulls and anxieties and habits people have around the tools they use, and why they might be looking for something new, but also why they might stay with what they're doing right now. And I am so curious to hear kind of like how this came about, and how you have been using customer research as you explore summits. So can you kind of like take us back in time to when you first started researching Summit?
Matt Wensing 1:52
Yeah, absolutely. So it's funny that there's actually an overlap here between even knowing what jobs be done enforces progress is and that initial research. So I attend the business of software conference each year in the States, so there's one in Europe and the States, but every October, in Boston, folks get together, at least pretty COVID and cross fingers soon. And Bob molesta is a regular speaker there as well, who is not sure the godfather of the forces of progress framework in a lot of ways. And I just remember being this is probably Oh, man, time's flying, right. So let's just say five years ago, I wanted to say three and like now, it's not three, it's probably five years ago, I listened to him interview, an audience member, kind of a mock customer interview, live about purchasing a car. And the way that they were able to take a dialogue and really parse it into a framework that you could then take away from that, and then keep doing that with more and more conversation. It just was like, Okay, this is definitely a tool that I need to add to my tool belt like this is, this is amazing. What's interesting is then fast forward into Summit, like by that time in the history of my previous company, I was doing sales, enterprise sales, mostly it wasn't doing a lot of customer research, at least in terms of the early sort of genesis of the product. So I don't know that I got to use it a lot. Back then it was mostly just listening to like we did do enterprise deals where there were custom features involved. But really, I got to use it fresh, you know, when you're second time founder, a lot of times you're like, Oh, I'm gonna do this the right way, this time around and actually use more tools and framework things I've learned. And forces progress is one of those. So I wanted to build this tool to do financial modeling. But that is such an ambiguous target that I knew I needed to figure out the value proposition. What does that really mean? What do people want? So funny enough, I gave a talk at business a software as a lightning talk in 2019. And I kind of use that as a launching point. I didn't frame it as, hey, I'm selling a product. I didn't even have a product. I had a little prototype, basically. But I use that talk to share. Really, the problem, socialize the problem space, if you will talk about, hey, this is this is a challenge, isn't it? Like this is a pain. Here's a little tool I made to kind of deal with that pain. And I really tried to draw some business lessons out of it. But really, at that same time, I started to have conversations with potential customers and prospects. And as they talked to me, I started cataloger file their feedback into these different kind of buckets, right, kind of the tool that I had learned previously and yeah, I just kind of did that every you know a few months would kind of refresh my understanding of what they were saying and built up this. This list organized list of feedback which I guess I'll put a bow on it and say it really think helped me understand the product strategy, like what did the product strategy need to be, for me to go into this space that was otherwise very nebulous? Like, how do I have opinion? Like what should my opinions be about the tool and what it needs to do? Right?
Michele Hansen 5:19
Mm hmm. It's really it's really interesting that you use basically that talk as sort of a, I guess, sort of, in a way, sort of what Patrick McKenzie would call a friend catcher, to attract people to you to talk about the problem. But then because you had that experience with the forces of progress and with seeing Bob Maestas speak who, by the way, his his book, demand side sales actually has real customer interviews in it that are all broken down by the forces. And it's like, it's so good, like it should be on everybody's shelf. And then, but you you were able to process that. And I think that's so important, because sometimes there can can feel like there's this gap between for people who are new to research of how do I go from talking to people to actually designing value? And how do I figure out okay, I've talked to these people, I know what these problems are, I know what I'm interested in. But then what is the product? And it sounds like you were able to bridge that? So I'm curious if you can kind of dive into when you went from this point of understanding the problem space socializing the problem space, you kind of had a prototype, but like, how did the prototype sort of snowball with that? And how did you figure out where it was valuable?
Matt Wensing 6:48
Yeah, so to put a timeline on this, this was, what you're describing now is essentially the journey from late 20, October 2019, through probably April, May of this year, so you know, almost almost two years, essentially. And during that time, I've released multiple versions of the products, really knowing that this was not going to be it. Now I'm a developer, a full stack developer who can build full, I can build applications top to bottom, not as strong as they used to be on the front end, but like it works. And what I was essentially trying to do was understand, okay, so there are few risks of the business. And funnily enough, Patrick McKenzie was one of the first people I pinged about this idea, because was his work at stripe Atlas and stripe. And just in general, I knew that he would have interesting opinion. And his thoughts were okay, financial modeling is interesting. But it sounds like it could be transactional, like, somebody has a need, they do it. And then they're gone. And I knew I wanted to build a SAS. And so that was like, Okay, that's a great point. Because a lot of times, the use cases that would come up when I talked to people were, oh, yeah, I have this investor meeting, or Oh, yeah, I have this fundraiser. Oh, yeah, I need to figure this thing out. And it sounded like it had a pretty finite shelf life of utility. People come they use it, then they go away. I was like, okay, that's not a great recurring revenue business, you know, because it sounds like something you could just sell for $50 one time, and then people don't ever need to keep paying you anything. So I recognize that pretty early on that engagement was a key risk to the business being a sustaining recurring revenue model. And engagement is tricky, because as much as you want to do, you know, mock ups and kind of smoke tests and things that are not you don't want to over invest in engineering, it's very hard to de risk engagements with a paper mock up or a screenshot or a prototype, like, how do you know that they're gonna come back to it unless they actually get to use something. So I basically spent those 18 to 24 months, releasing, what I knew were really technically debt laden, let's put it that way versions of the product, where all I cared was that the front end was communicating what I wanted it to like, this is what this is, this is what this does for you. If you click this button, this happens, and it works, how it works less important. So I built a lot of basically throw away versions of the product, which was expensive, but I felt like it was the key to knowing would people actually come back and reuse it? And I guess let's pause there. That was my approach. And that was why I took that approach to de risking or, or getting more valuable feedback from people than just like, a conversation or interview right? And then I think I paired that with, do you use Excel to use sheets, you know, how do you do this today? But I learned, I just want to point out, I learned from both the usage of the early versions and the customer conversations.
Michele Hansen 10:12
I love how you underscored there, how the customers intrinsic behavior and their intrinsic needs, drive usage of the product, like there's only so many sort of engagement hacks that you can do to make someone come back to a product. But like, if they only need to raise money every 18 months, then there's nothing that you can do that will make them come back daily or weekly, because their fundamental underlying need for the product is infrequent. And I'm reminded of the pain and frequency framework from Dez trainer, which, you know, he said, you know, that that most, you know, painful and frequent is sort of the best quadrant to be in, because people have an underlying need for something and they're annoyed by it. But infrequent and painful, can be kind of a danger zone, it can be a space for good products, you know, I think, you know, I sort of think of like buying a house and getting a mortgage is very expensive. And it's so complicated. And it's, you know, expensive to get it wrong, but it's very infrequent. But other things that are infrequent and painful, you know, can maybe not be a great business, which it sounds like you had some indications that the underlying need for this, what you were originally thinking would not be frequent and and therefore people would not have a subscription. And so rather than staying with that, and going down the path, and then a year from now being like oh my god, I have this churn problem. How do I keep people to stay around? You pivoted towards something that was more frequent.
Matt Wensing 11:58
Yeah, that's exactly right. So I often use the metaphor for the first version as like, because I didn't know what else to build. So I just bought, I just built, I built the version that I knew people would use at least that first time, right? Because then I knew it was gonna fail. I felt like it was gonna fail. But I was like, okay, but I have to figure out the bridge from here to there. Like, I have to take a step. And so I'm going to give them at least gonna give them that initial thing and then just see, will they tell me like, you know, what else would be great is if, you know, like, what else could I learn by doing this? And so I built kind of that coin operated version, I call it like a vending machine for a financial forecast. Because my original thought was, yeah, people need a forecast. That was the value proposition, how fast can I get them a forecast that that works. And people use that. But then again, it was the churn problem, it was the going away, it was the it was hard to build, you know, that raving fan base, that you need to get something off the ground? Because it just wasn't sustainable. So I realized that to build a SAS in this space, I was going to have to figure out what did they do regularly? You know, like, Okay, if you only close your books once a month, or even your maybe you don't even do that, because you have a bookkeeper or accountant that does that for you. If you only raise money every 18 months, like what is it that you do? That's close to this that is more frequent? And that's really how I got drawn into more of the modeling space meaning like, Okay, but what, tell me about what you do regularly, and if you look at what these founders made, if I would just have them, show me what you made, show me what you made, I basically got into this thing of like, you are spending time somewhere. Where is that? What are you doing, right? And they would show me, the spreadsheets that they were making, that were very ephemeral, like they were very, they were throwaway products, if you will, they would make this like, I gotta figure out if I can afford this higher. And so they would just come into a G sheet G sheets, not new, right? Create a little spreadsheet and then use it for like a day, and then go away. But then it's like, well, how many of these do you have? Say, Oh, well, I mean, I probably do that, you know, once a once every other week, once a week, twice a month, like sometimes multiple times. And I'm like, wait a minute. So you don't build like a giant, you know, official forecast all the time. But you are using spreadsheets a lot. And you are doing things with money in spreadsheets a lot. Like Tell me about that. And that started to inform our strategy of Wait a minute, you know, there's really two customers here are two potential users. There's the CFO, if you will, or the analyst who builds those. That's the founder, even if it's a founder that's a hat they were where they do it like every once in a while I have to get serious about finance and do this proper thing. And then there's the non CFO founder, I just need something to solve my question or answer my question, person persona, who actually kind of does this work that they don't show to anyone else? They're really embarrassed. They know it's not, you know, they know it's not. Right, like with a capital R, right. But they're doing it a lot. Like they're doing this to make all the little decisions about pricing and metrics and goals. And how much can I afford to pay this person, like, I'm like, wait a minute. Turns out, you're actually doing a lot of modeling, you just don't talk about it. And you don't, you don't show it to anybody because you're embarrassed, right? It's this like dirty little secret almost that you have that you build these things and make decisions. Because of course, you use numbers, nobody doesn't use numbers, but like, you just don't call this some financial model. So that was a key insight, realizing that there were these two personas that were actually living within the same person. And they had compartmentalize those very cleanly, but I was much more interested suddenly in the other person, right.
Michele Hansen 16:13
That's so interesting. Like, you know that what you just showed there is, I think it's such a key, a key point and activity based design, which is the idea that we're designing for activities that people do and not for a specific person. And so in my book, for example, I talk about, you know, everything is a process, and everything is an activity. And the activity of you know, for example, one person might both have a Carraig pod coffee machine, and have a French press. But they use the Carib pod coffee machine when they're trying to get the kids to school in the morning, and they're rushed, and they're doing a million other things. And they use the French press on the weekend when they have a friend over to chat. And to them. Those are two very different activities that they're doing. But they're being done by the same person. And so if you design for the person, that wouldn't make sense to you that they would own both, and would try to pigeonhole them into one. But really, they're a person who's doing many different activities with many different goals. And so you have this one activity where I need to create financial models for official purposes, to share them with other people, maybe for compliance reasons, maybe for sort of me in my official capacity reasons where other people are reviewing this. And then there's also this activity of, I need to make a decision that involves numbers. And it's basically this sort of like there's the official activity. And then there's the back of the envelopes activity, which is where this kind of I've heard people describe summit as like a whiteboard that does math. Yes. And that is also where that activity comes in. And that's more so replacing those those millions of spreadsheets and which other really fascinating about this is that so often is the core thing and jobs to be done. So often the competitors to a product is not actually another piece of software or another product product. It's somebody doing it. It's them making a spreadsheet. It's something in Google Docs, it's like them doing it by hand like that is as much a competitor as another piece of software. It's like, there's so many pieces. Yes, this is great.
Matt Wensing 18:37
Oh, yeah. And that's why, you know, I try to explain, like, this is such a journey, because you, we joke within the company, like, gosh, we did you know, we were so dumb a week ago, like how we thought we were so smart, but we knew nothing. And when I started this journey, you know, you just so in the dark, and then you take these steps and you realize, wait a minute, wait a minute. And so it is kind of a weird thing that you have this perennial sort of optimism as a founder that there's something here and you can you want to figure out that if you're wrong, you're wrong, but at the same time, people are not telling you. You know, and this is the thing I think so key like this is a skill to develop is people are not what people don't say is as important as what they do say and like learning to find out that wait a minute, we were we were standing in this room, if you will, in your mind talking about financial modeling. And here I am thinking that this is where the gold is, you know, this is trying to get all my answers. And you're telling me next door you've got like 12 spreadsheets with numbers and money in them and you're you didn't tell me about like, how did I How was I so close but yet like you didn't you know, like if I had just if I had given up them right. I would have missed the room that actually had all the gold in it right? But it was literally connected but in their mind at what it was a different room. It's like oh, you're asking Give me about this. But, you know, you're not asking about that. And so that's what's so kind of vexing for like, in hindsight, I just laugh because stumbling across the actual value is is something that you, you partly luck part skill and getting people to. And really I'll cut my rambling short by saying I think observation is more powerful in those cases than just question and answer because the real key for me was when I said, Show me, show me what you have today. And they had to, you know, at that point, they couldn't say, like, Why have nothing. But they did have to say, Oh, well, let me open up the store over here and show you what I have today, because I haven't been through a fundraiser, and I haven't, whatever, but I've got something. And it's only when I said, Show me that I got to see like, wait a minute, there's this whole other room here, that is exactly where I want to be. So we pivoted our strategy towards that other space. And it's been very fruitful.
Michele Hansen 21:12
And there's two really important skills for entrepreneurs there, that you just sort of, underscored without really stating them outright, that I want to, I want to hone in on for a second. The first one was basically thinking about how much of an idiot you were a week ago, and thinking about that, and not being embarrassed about it, but kind of being like, delighted that you have learned something, and that you have added to your understanding of customers. And, and kind of being able to like, not laugh at yourself, but almost sort of look at it with like this, this sort of it's almost a pride in a way of being like, man, I was such an idiot six months ago, like, and it's kind of delightful to have those moments of realizing how much you didn't know, but to be delighted by that, and not be embarrassed by that. And kind of as a company being able to say, like, Yeah, we had no idea we're doing. And now we six months from now, we're also gonna say we, you know, we don't know what we're doing. Right? Like, but you know, we are aware of that. And then also the curiosity, the combination of that approach to learning and being excited by learning and looking for surprises, and then allowing yourself to be curious when you talk to the customers, and not just accepting what they're saying at face value. But saying, Well, can you? What's what's in this closet over here, like, and just, but like, you can only get to that point if you have really built trust with them. Because as you said earlier, they were embarrassed by doing this back of the envelope math, they were embarrassed by their legions of spreadsheets of whether they can hire people because it wasn't real official forecasts done by a BI team, like maybe they they're so small, they don't even have a BI team. Right? Like, exactly. So. And so they don't want to show this anyway. But when you did the interviews, they trusted you enough, which tells me that the way you ran the interviews was when you ran them really well, because they were willing to let you in and poke into what you thought was a little closet. But it turned out they were like pulling out a books and a book. And then the whole bookcase like turns around. And it's like their secret lair full of spreadsheets.
Matt Wensing 23:36
Exactly, exactly. Was that they had made like yesterday, and then this one from today and that one from a week ago. And I'm like, wait a minute, you're not just doing this, like once every you're doing this, like, this is enough, guys, this is enough, you know? And like, what if you actually enjoy doing this? Like, oh, wow, you know, and so then it was like the opportunity to switch that negative emotion to a positive one and say, let's change embarrassment to fun and joy and just, let's embrace the informality of it by letting you do it this way. But we're going to level you up like we're going to make it better and faster and take out the tedium. So that's where I went back into my forces of progress. And I said, Okay, for this non CFO founder, what are their thoughts? And you know, they say stuff like, I'm embarrassed by my spreadsheet. I'm not very good at this,
Michele Hansen 24:29
right. Also, their spreadsheet, like they love playing in the spreadsheet. They
Matt Wensing 24:33
do love to play exactly. So they like the act of playing with it, right? It's almost like a child who's like, I love to finger paint and create things. But then it's like the kid who's embarrassed to show his parents or teacher whomever like well, you know, this is just for me. And so it was a very, like private activity. And so I was like, wait a minute, so this is an opportunity to say, Don't worry, we've got your back. Like, we'll make sure the math is right. We'll run the team will do the tedious parts for you. We'll make it look really well designed without you having to do the work of making it look professional. And we'll even help you use smarter, you know, building blocks to do this work. So you might not, you still might not use it to do that fundraiser, get that for an evaluation or whatever, like, you're still gonna have to create a spreadsheet, perhaps, for all those little decisions. Like, that's where summit wants to start, like, we want to be your tool for that, right? And I think over time, we can grow into the, oh, hey, you're really, you're really skilled at Excel? Are you really good at G sheets, and you have total, you are like, really confident and proud of your work? We'll get to you, but like this, then give us that shape of adoption that that's okay. Like, there's enough people. And in fact, there's more people. It's a bigger market of people who are a little bit embarrassed, a little shy and a little inexperienced, frankly, with this stuff than the other one. And oh, gosh, guess what team? Like, the feature requirements are completely different. Like, instead of having to build the enterprise, incredible version, that's going to win people away who are like veterans, right? We get to start with, like, the people who need the simplest things, you know, like that was the other exciting part is that, wow, you're just doing addition, subtraction, multiplication, division, basically, right? Like, okay, great. You know, I don't have to like, cuz I will say, you know, I don't want to leave this part out, like there was a pivotal moment in those 18 months where I was, hadn't decided yet that this is where we were going to go. And I found myself torn, trying to build more and more sophisticated tools and analysis for that really confident diehard user. And they were so demanding, and so exacting, and I was just barely getting, like, I'd say a b plus, with them. And it was causing me to almost have to go, Okay, this is going to end up being a consulting business, if I'm not careful, because I'm going to end up having to do a lot of bespoke work a lot of custom work for them, I'm going to end up, you know, having to get into the models that mean, I have to become a data scientist, like it was just so intense, that I realized, okay, this is not the business I want to build either like, this is just a bad fit from a, you know, I want a high margin, self serve SAS business. And I might come back to y'all. But this is not where I'm going to start. I can't I can't start here, because there's only one of me. At that point, there was one of me so. So I made the decision, then, okay, we're going all in on the other side. And that also allowed us to say, wait a minute, you know, all these opinions, we were baking into the product, all these best practices, all these things, we kind of need to like, lower that not come across as so proper and formal and the right way to do things, you know, you can only do things the right way, right? We actually need to be more invited, it changed our whole brand, right? We went through a rebrand where we said, instead of being serious and professional and discipline looking like Wall Street kind of style branding, you know, traditional financial branding, we actually said, what if we were playful and inviting and inclusive, and, you know, just warm and friendly with our branding, that would actually resonate more with these people who treat this stuff as their playground, right, like you said, and so it didn't just affect your product strategy, you know, really changed our whole positioning and brand identity, once we realized that this was the this was the side of the person we wanted to go after. Right?
Michele Hansen 28:48
Hmm. It's so interesting that there were multiple inflection points there. Were you really stopped to think like, is this the business we should build? Whether that's from a product perspective? Or from a, you know, like a business perspective? Like, is this the business I want to be in? And when those points came? In sounds like you were quite reflective about them. And, you know, you know what, when you're at that point where you realized, you know, that, you know, that people were not doing the modeling, you initially thought they were on the frequency that you hoped they would be. You could have been threatened by that discovery. And you could have decided to, you know, give up or dig your heels in on it. And you didn't, and I think that it's such an important mental shift that needs to happen in order to really do customer research well, is to be open to what you're going to hear and to follow it wherever it's going to take you. And so you initially thought You were building a serious financial modeling tool for, you know, say startups, CFOs, and founders that is polished and professional, and they can give it to their boards or whatever. Yep. And, and then it turns out, you're actually making this fun private playground for them to make decisions in, in a way that helps them do it faster, and maybe doesn't use all of the skills they have about, you know, you know, decision support systems they learned in business school, but instead, it's somewhere that's like, safe. And yeah, for them. That's a very different business than you thought you were building. And you allowed yourself to be, you know, sort of led by the customer, still applying your own, you know, analysis on top of that, still asking yourself, you know, of all of these different directions that customers leading me in, or I could allow them to lead me in, you know, are those businesses I want to be in? Are those products I want to build? Is that is that the future I want for myself and for this company? And you allow that answer to be No, right? You didn't just force yourself into it. But you said, No, and we're going to do something else. Because there's something else that's interesting here, like there's still something here. Yeah. And maybe that's not it, but there's something else, but allowing yourself to sort of just just sort of to go with it, but still be steering it at the same time. And I don't I don't know if I'm quite conceptualizing that very well.
Matt Wensing 31:40
No, yeah, it describes, you know, basically describes, I would say, December of 2020, in January 2021, where we just realized that I realized that this was not the right segments, this is not the right value prop for the right, you know, hats that people were wearing. And we were able to charge more money, but it wasn't going to grow the way I wanted to. So we rebuilt the darn thing, again, for hopefully the last time in April, May and June of this year, and then release the beta version in July. And it's really exciting. Now we've had three months of growth, we've had three months of consecutive growth, which had never happened before. Right. So revenue up each month, and retention. So we've actually had negative net negative retention each month, which has never happened before, either. So it turns out these people love it, it's doing what they want to the prices, right? And there's a lot of them. So I'm like, This is great. You know, you know, we have that we have a business and I will come it's funny, full circle, we now have some of our users who are founders, saying, hey, one of them, it blew my mind, he shared a screenshot of a zoom call with his board, where he did show summit on the call, which he never would have done with the G sheet that he created. Right. But because it looks like rigor, it looks rigorous. It's actually doing justice to his thoughts. Like he's a super smart person. But I think the problem before was like a mismatch between, you know, the tools that he had to express his logic and his thinking and his, his conceptual gifts, right, like, very, very talented, but like, you put them in front of a spreadsheet, and he would, you know, that just wasn't his native tongue. Right. It wasn't where he wanted wasn't the right tool for him to express those thoughts. Now that he and they have that they are starting to share them more on tweets, and with board meetings and like, which is great for us. But I think it's a testament to the fact that they're proud of their work now. Right. And that's really exciting for us. So yeah, it's it's a journey.
Michele Hansen 34:01
It sounds like it has been, I mean, an incredible journey so far. I'm I'm super excited to see where this takes you. i You know, I've had a little bit of experience with with you know, with working with analysts myself, because I used to work in sort of the the financial space and I definitely knew a lot of people who love their spreadsheets and, you know, like genuinely reveled in making discounted cash flows and excel and very proud of your macros. Yeah, thing. And, yeah, yeah. Like, just like, and I mean, I feel like I have a little bit of that where I like, you know, genuinely enjoy, like playing in a spreadsheet. Yeah. And it's been so cool to see everything that you're sharing about different kinds of things that you could do with it, but also people doing it for their own personal budgeting and like, you know, founders, like founder financial situations are always so like weird and different and like, figuring out whether, you know, can I? Can I do this? Can I send my kid to this school? Can I, you know, can I buy a house, you know, all of those sorts of different things. Um, really, really exciting stuff. And, and, you know, I noticed you tweeted recently that you feel like you're getting to that, that point where it's really, it's really starting to take off and have that. You know, you know, you feel like you have found the product, you have discovered the products, which is the hardest part, and that you're getting those rabid fans. And actually, I told you this already, but I was at a wedding a couple of weeks ago. And these table I was sitting at like the, you know, there are two guys who work in finance sitting across the table from me. And like one of them was like telling them like about summit and how awesome it was and how he had to get access to it and all this like stuff you've built with it, you know, and I was on the other side of this huge table, and I wasn't really part of that conversation. But I was like, What are they talking about what they think I think, you know, wow, like, Oh, my God, like the internet in real life happening at this table at wedding.
Matt Wensing 36:12
Founders delight right there. Yeah, yeah.
Michele Hansen 36:16
But I think there's, I think we're gonna be hearing a lot more of people using summit and stuff so you can do with it. It has been an absolute delight talking to you today. Thank you so much for giving us some insights into your customer research and product discovery process. I really appreciate.
Matt Wensing 36:38
You're welcome. Thanks for having me, Michelle.
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