thoughtbot's Incubator Program Mini Season - Episode 02: AvidFirst with Ashley Sheble

In this second conversation in this Mini Incubator Series, Dawn Delatte and Jordyn Bonds interview Ashley Sheble, the Founder of AvidFirst, about her experiences and progress in thoughtbot's Incubator Program, which aims to help founders like Ashley turn an idea into a viable product. The trio talks about Ashley's experiences and progress in the program. She emphasizes the significance of user research and interviews in shaping product strategy and understanding customer needs. She also highlights the need to narrow their focus to specific customer segments to build a product that resonates with a particular group. Additionally, they discuss the complexities of the FinTech industry and how regulatory considerations are an integral part of their product development process. As they gain more insights, they are transitioning into the prototyping and testing phase to validate their product concepts and messaging. Just catching up? Listen to Part I of the Mini Incubator Series. Follow Ashley Sheble on LinkedIn. Follow thoughtbot on X or LinkedIn. Become a Sponsor of Giant Robots! Transcript: DAWN: Hello, everyone. I'm Dawn Delatte. I am a Managing Director here at thoughtbot. And I'm filling in for Lindsey. And I'm super excited to be here and chat with Ashley and Jordyn about how the incubator is going so far. If you are tuning in, you're probably familiar with thoughtbot, but just in case you're not, we are a product design and development consultancy who works with people and products across the entire product lifecycle to make your team and product a success. We are currently running our second incubator session. If you're not familiar with it, we've got a ton of content from our first session that you can check out, or you can follow along in this one. But our incubator program is an eight-week program that we take a founder through to validate or invalidate their new product ideas through lots of market research, customer discovery, interviews, and such. And then, we come out with a product plan that helps set them on the right path forward. In the last update, we introduced our incubator founder, who's with us again today. In this session, we'll be talking with Ashley and Jordyn about digging deep into research and plenty of interviews and, you know, what they're learning and what the process is like so far. So, I'm excited to get started. How about y'all kick us off with some introductions? Jordyn? JORDYN: I'm Jordyn Bonds. I'm the Director of Product Strategy at thoughtbot on Dawn's team, the Ignite team at thoughtbot. I'm a two-time startup founder myself. I've worked with a couple of other early-stage startups, so all about the zero-to-one startup journey over here. ASHLEY: And I'm Ashley Sheble. I am the Founder of AvidFirst, and I am the second incubator founder. And working with Jordyn and team and thoughtbot to really accelerate the mission of our company, which is focused on simplifying college saving and spending. DAWN: Ashley, why don't you recap a little bit for us what's happened since the last time? ASHLEY: Yeah, I'd love to. So, the past three weeks have been really just getting into the weeds on user interviews, talking with different stakeholders as it relates to the problem we're looking to solve. And what we're finding are some key themes. And so, really trying to aggregate the data, focus in on those key themes, and find out where we can really pull at some of those strings to start creating some solutions that are meaningful and specific. One of the primary trends that we're seeing is just lack of awareness around some of the resources and tools available to people as it relates to saving for college; 529s, for example, are a really great tool. And most people, 70%, aren't aware of them. And so, if you've never heard of them, you're in great company. So, just really looking at high-level trends, getting more specific on even more granular trends, and trying to pull everything together and create a product that's meaningful. And again, it circles back to our overarching mission of simplifying college saving and spending. DAWN: Nice. Is there something that has come up either in the process or, you know, from interviews that has been your big sort of aha or eureka moment? ASHLEY: I feel like there's an aha moment pretty much every day. And sometimes the aha moments are like, oh my gosh, this is amazing. We're really on to something. And then, sometimes the aha moments are like, wow, we're really off course, and we have no idea what this means and what do we do with it. And so, it's kind of this up-and-down experience, like we talked about last time we chatted. But it is exciting at the same time because no matter what aha moment, all of it means something. And it helps us make forward progress in the right direction versus making forward progress and then hitting a roadblock and realizing, okay, that's as far as we can go, and now we have to start all over. The team has been really good about helping me make sense of some of these findings that we are uncovering and piecing together some solutions that really address some of these aha moments, both shocking and positive. DAWN: It's really great to hear you articulate that from a founder perspective and someone who, you know, isn't doing this sort of day-to-day product and development thing because, you know, that's a really common experience for us is hearing what's going well and what's not going well and sort of pivoting. But yeah, it's good to hear that directly from you. So, y'all have been doing a ton of research and a ton of talking to people. Jordyn, tell us how you feel about user research. I know that term, in particular, has some interesting [chuckles] connotations, but dig into that. JORDYN: Yeah. Well, we kind of talked about this a little bit this week, and I think research is really broad and vague. And so, just talking about research often doesn't feel super sort of actionable to people. User research is really about once you have a product and market and you have users, how they're using your product or not using it, right? So that's user research. But I find that people often talk about this sort of higher-level strategic research that we're engaged in right now using the same term. And it leads people astray because they think that you need a prototype or you need an app to be able to do user research, which you do. But that's not really the kind of research that we're engaged in yet. Right now, we're doing customer discovery. And that involves researching and interviewing a ton of different personas, some of whom might end up being our customers, some of whom are interested stakeholders or partners. It's a really wide-ranging kind of cast of characters. And the truth is, we don't know who these people are to us yet, right? So, it's really just sort of interviewing [laughs]. It's a hard thing to kind of characterize. I would love to hear, Ashley, like, how you're finding it. But, like, from where I sit, it really isn't about walking people through an interface yet. It's way more just asking folks about their life and their work and how they're doing things now, I think, is a really critical component. Like what you're trying to do with these interviews is find out what are the true pain points that people have, not what they think you want to hear, but what the pain points are that they already have and that they are already trying to solve in certain ways and how they're solving them. And it requires a lot of just high-level questions and then closing your mouth and listening. But it's a very different thing, I think, than user research. But often, in product land, we kind of just use user research as this blanket term, but it really is a bunch of different kinds of things. ASHLEY: Yeah, I would add to what Jordyn is saying, and the use of research, it's really interesting to just hear people's experience and their own background. And we always try to preface, like, there is no right or wrong answer. We just want to hear about the way you're thinking about something or the way you're currently doing something, not how you hypothetically would do something. Because, I don't know, think about your own life, and you think about the way you would do something. It's probably about ten times better than the way you actually do something. When I get asked like, "Well, how many times a day do you set time to just decompress?" In my mind, I'm like, "Oh, probably, like, five times a day." When in reality, that's never. It's a never. So, if somebody were, like, you know, asking me for user research, you know, "Would you use this thing to decompress?" I'd be like, "Sure." But I wouldn't. I would not use it because I just don't make the time for something like that. So, the point is, is not asking people hypothetically how they would do something but how they're actually doing something now and then using that insight to build around. And then, beyond just that customer journey, the stakeholder journey. And when you think about building a solution, there are more people involved than just the end user. There are so many different parties that play into a certain product, especially as you think about FinTech or you think about a large segment like the education segment. There are a lot of players, and you have to look at the way each player is looking at a problem and understand how those all tie together. And sometimes that's super obvious, and sometimes it's not obvious at all. And so, thankfully, having a team that has a different lens in the way we're interpreting data allows us to get to a solution faster. DAWN: Yeah, I like that. Again, it's great to hear you articulating that. And I think we have this old article about not using terms like user research. I think it focuses a little bit more on user testing because that implies the idea of testing a user. But we're not testing people; we're testing our concepts. I think that we use the word usability test as a way to sort of delineate a little bit better. Here's the purpose of this test. We're actually testing the product versus, you know, having a conversation. When you throw in words like interview or even customer, customer could be presumptive in some ways. But it's difficult to sort of tell people what you're doing when you're like, I'm just having a lot of conversations this week [laughs], just meeting, meeting a lot of people and listening. Meeting and listening, I guess, is the activity [laughs]. So, why is that stuff important? And can there be too much of it? What is this process like, and why are y'all doing it? JORDYN: It's so funny to have internalized the sort of value of doing this kind of work so thoroughly that sometimes I even have...I'm like, how else do you know what's going on out there? I mean, that's ultimately the purpose of it is that you really don't know how people are living and working until you ask them or, even better, watch them live and work if you can. And what's really critical is that that changes over time. We're all constantly changing our behavior in response to new trends, new tools we might adopt, right? And the research at this level, this high level of, like, how are you living and working, really can never end for that reason, right? Like, the classic example in sort of software product land is when Netflix really started to invest in online streaming and gradually sunset its DVD-by-mail service. And they did it right at the peak of that service. And so, people were like, this is really wild. Why are they doing this? This is so successful. Why would they, like, stop doing this thing that's really successful? But they had been talking to their customers, their end users. They had been, as you said, Dawn, more than talking to them, listening to them. And they were looking at the trends. And they were like, there's no future in this. There's a future in online streaming, and we need to get ahead of that future. And we need to dominate that opportunity because we're in a position to do so. And it takes a lot of listening, synthesizing, and then risk-taking. But it doesn't feel like a risk when you've been listening to your customers, I guess, is, like, why this research is so important. When you know something about the market because there is no daylight between you and how folks are living and what they're doing out there, it doesn't feel very risky. You have, like, complete certainty about what's happening out there because you know. Because you're talking to people. You have relationships with them. It's not merely about some...and when we say research, I don't want it to sound, like, sort of cold and, like, purely numbers-driven. This is, like, we're having warm, engaging, you know, human conversations with human beings, like, all day, every day. But because of that, we have a really good sense of what's going on out there. And the decisions we make, they feel inevitable or something. You start to see an opportunity out there that just feels obvious. And it's a funny thing to watch that kind of once everybody on the team is aligned around that reality that we're hearing and the sort of inevitability of, like, what you need. You start to get kind of panicked because you're like, who else is seeing this? This is so obvious to us. And you start to kind of be like, who else is it obvious to? But, you know, sadly, I don't know what the right word is here, but, like, it's hard work. This work of listening it is not very scalable work. You can do some things to operationalize it for sure, but it takes time to engage with humans, to synthesize what you've heard, to share it with your team, to stay on the same page about it. It's not super scalable work, straight up. But it is the most valuable work that you could possibly be doing. So, it's okay that it's not scalable. But yeah, you start to identify these real market insights. And then you kind of have this minute of, like, who else is seeing this? Because this looks really clear to us, right? [laughs] ASHLEY: And it's interesting because the last time we chatted here a couple of weeks ago, Lindsey was like, "I'm sure you'll be in a different spot next week. And, you know, you'll be thinking about something different than you are right now." And, in my head, I was like, probably not. I've done a lot of research. It'll probably be the same. And she was right. It's very different from where we were a couple of weeks ago, and the way we're thinking about taking a certain path and circling back to having these conversations that are so critical and really shape the way you're thinking about problems from so many different directions. And so, I thought that was funny that she was right. DAWN: Lindsey is always right. JORDYN: Another ingredient here that I think is really important that becomes clear when you start doing this work but is a hard thing to describe...and I would kind of love to hear how Ashley has been thinking about this. But if you're not hearing a pattern, if you're out there doing the interviewing and it's just a million different descriptions of reality, that is the surest sign that you are not focused on a small enough addressable group of people. You haven't narrowed into a group of people who are the same. And that's really the only way to build a product is to find a group of people who are the same. Make something for them that they love, and then think about where you can go from there. You can't please all of the people all of the time, but you can't please all the people at once, right? You're not going to be able to build a product that does that. And I would say, like, even later, you're not, you know, there's like...it just...it totally dilutes your focus. So, if you are out there doing a bunch of interviewing, a bunch of research, and you're just hearing a bunch of different voices, and it sounds like there's no signal there, it's just that you haven't sufficiently narrowed. So, one of the things we've been doing over the last couple of weeks is really trying to figure out who exactly has the pain point the most that is addressable, in the sense that it's a group of people who are similar, similar enough that we can build a product for them, that is going to work for all of them, and we can speak about it in a way that resonates for them? And it feels kind of impossible. And it also kind of feels, I don't know, a little bit like cheating. Like, it feels opposite of how I think founders think about making products. It's like, you want to build a thing that appeals to a lot of people. That's the drive, and that is absolutely the correct long-term drive, right? And it feels a little bit about sort of throw the game by choosing the people. It feels a little bit like you're like, well, of course, we can make something for a group of people if we've already pre-selected who they are, but it's like, yeah, exactly, that's a lot easier [laughs]. So, anyway, I didn't want to move on without sort of mentioning that that focus on a persona is really, really critical. Yes, we're doing a ton of research, or we're talking to a ton of different people. But in each of those categories, we're really trying to figure out who are addressable niches to start? ASHLEY: Yeah, and I think just getting as specific as possible, like Jordyn has said, has been...in my mind, I was thinking, we don't want to do that because then that really limits the amount of people we can help or the amount of people who could really benefit from a solution. But the good news is that once you solve a problem for a group of people, you can expand upon that and use the learnings from that solution and build something that can help more and more people. Because initially, I was like, "No, we don't want to do that. That's crazy." And she was right. DAWN: Jordyn is another one of those people that's always right [laughs]. Mostly right. Okay, so you're using what you're finding and hearing in these conversations to help guide, you know, your focus, but especially the space that y'all are operating in, FinTech, in particular, is a very complex space. And so, there's all sorts of other dynamics that have to come into your strategy and direction for the product. So, how are y'all navigating which dynamics to focus on outside of what you're discovering in these conversations, you know, whether that be infrastructure, regulatory things, like, you know, all of those complexities? ASHLEY: Yeah, I would say, right now, we're focusing on infrastructure. And that will inform the regulatory piece because there are so many nuances in the space as it relates to what type of product you're building for whom and where. And so, once that is more crystallized, the regulatory pieces can be plugged in. And you're right; it's super complex. And we want to make sure that we're being extremely compliant in every possible way. And so, that is highest priority. But I think, too, to try to boil the ocean with all the different nuances when maybe we're not as crystal clear on the infrastructure would be, I don't know, waste of time is the wrong phrase, but I think it would not be the most efficient use of time. I think getting that infrastructure and then nailing down the regulatory piece around the infrastructure is the best path that we're thinking. JORDYN: Yeah, I would just add here that this space is really complex. And the image that's kind of emerged most recently is of a giant puzzle we're putting together. There are a lot of pieces to this puzzle. It's not a thousand-piece puzzle, but it feels close [laughs]. But where we're starting out is where you start with any puzzle, which is the corner pieces. Like, what are the cornerstones of what we're doing? And figuring out what those are, always centered in what the value proposition is to customers, right? We need to know what their incentives are, what they need and want. That's the cornerstone. And then the feasibility and the infrastructure and, you know, regulatory are the blanks we fill in sort of from there. But without demand, none of that stuff would matter, right? It's a really hard thing because you start to think about...and we talk about this stuff all the time; I want to call out. It's not, like, we're strictly disciplined about we're not talking about that right now. Like, it comes up all the time. And we're sharing what we're learning and what we're seeing out there. We're looking at other products that have, you know, come onto the market recently, like, long-time players in the FinTech space. We're looking at all of that stuff, what they've done, what they've built, and how. We're thinking and talking about those things, but those decisions are not as important as making sure that we're as close to the customer as we can. That's the cornerstone pieces. Our customers and our partners, what are their motivations? What do they need? And then, once we have those corner pieces, then we fill in the puzzle. It's a big, complex puzzle, but you always have to start with something of value. If you're not bringing something of value to those folks, none of this other stuff really matters. DAWN: This is making me wonder if there are people out there who start their puzzles in the middle [laughs]. JORDYN: Guilty as charged [laughs]. DAWN: I meant more [inaudible 18:57]. I didn't mean metaphorically. We know that happens [laughter], unfortunately. JORDYN: Yes, no, I have absolutely been that person personally, you know, and it can be really distracting. The feasibility puzzle is very interesting, and it feels inevitable. Like, you're going to have to solve those problems. The problem is that you don't know which of them is going to matter right now. So, solving those problems now, like Ashley said, it's sort of a waste of time. You might end up solving them eventually, right? But you need to figure out the strategic path forward. And so, yeah, it's tough. I have an engineering background. I love solving complex puzzles. It's very tempting to go do that right now, and it feels much more tangible. Like, okay, we can go read the regulations. We can, like, look at what the infrastructure can do right now. Let's go solve that problem. But it would be just a colossal waste of time to go off in that direction right now. And we don't yet know fully what the value proposition is for whom. Like, that is the gem at the heart of this. I want to acknowledge that there are software efforts out there where the core value really is in a technical innovation. But I would still argue that the timing of bringing that technical innovation to market has as much to do with the market. We can see this over and over again with tons of technologies that were developed years or decades ago, but the market was not at a place where it needed that thing yet. And I really say needed; wanted is a different thing, right? You need to get to a place where the need is red hot. So, it's tough. The puzzle is fascinating. It's very distracting. We end up talking about it a lot, but we have to, like, bring ourselves back to the stakeholders. DAWN: To wrap things up, now that y'all have sort of deepened your understanding of things, what can you expect from the process going forward? What should we expect to sort of hear about next time we meet? JORDYN: We're actually already edging into this, and it's fun to watch how this process happens. When you start to hear something repeatable, you inevitably move into prototyping because you start to have a real shared understanding of what it is you need to put in front of people. We're just now, I would say, like, today, getting to the place where we're confident that we need to be testing messaging in particular. We've heard enough things that we need to start testing. Like, are we talking about the problems in the way that, you know, customers and our partners are talking about them? And we need to start trying that language out and then seeing how it resonates. That's the first piece of testing. We're already starting to conceive of workflows, like a prototype concept. It's so fascinating how, again, it's just always is a consequence of alignment and insight. You don't have to plan it. It emerges. As soon as you've started to put the pieces together a little bit, it's just very natural that, as a group, you start talking about how you might address this problem. You can tell when we've gotten there because we are aligned. In the same way that you're hearing the same thing from the customer, you start to see the same solution because it's clear what is needed. So, we're really moving into that. I want to make it clear, like, we don't stop interviewing. We don't stop talking to folks. But the sort of how specific we are with what we're asking and what we're showing people changes a little bit. That's really just starting to happen now. And I'm sure we'll have a lot more to say about that next time [laughs]. ASHLEY: Yeah, it's been a lot of fun. I'll say the value of the team is incredible. I can't stress that enough. Just this morning, I came to our morning sync and was like, "Listen, I learned this thing. I think it's over. We're done." And Jordyn and team were like, "No, this is actually a really great thing." And, you know, I'm just like, they're going to give up. They're going to shut it down. They're going to say, "No, we don't want to work with you." And they're like, "This is great news." And so, just the diversity of perspective is so different, and it's really great to have that. Because sometimes you can get focused on something in such a linear way that you're like, there's no way out of this thing. And you kind of miss the forest for the trees, so... JORDYN: I'm glad you brought that moment up. I was hoping we would talk about it during this live session because it was one of those moments where you were like, "I have some really bad news. I learned something. This is very sad." And you kind of talked about it a minute. I had a sort of unbridled glee [laughs]. I was like, oh, awesome, because we knew enough to know there was, like, we were missing something. There are a bunch of solutions in the market that look very different than what we were considering. And we were like, why? There's got to be a good reason. These people are not dumb. The market they're seeing is not different from the market we're seeing. So, like, why have they made a different call? And this piece of information, you know, Ashley showed up and was like, "Hey, I learned something, here it is." And I was like, "That's the piece of information. Great." So, now we actually can make a plan. We are still sort of convinced of the value that we were driving toward. And now we just have an added understanding of what it will take to get there. Good. Now we know what it'll take. It's really terrible to have an idea of the value prop that you want to pursue and not have any idea of how would it get there. But now we actually really did feel like a piece of a puzzle falling into place. And it was hilarious because Ashely was, like, very grim, and then I was like, "Oh," I was like, "Great." [laughs] ASHLEY: I was like -- JORDYN: Ashley was like, "Wait, what?" [laughs] It was very funny. ASHLEY: Yeah, it was great. I was like, I hope the rest of my day is this good, so... [laughter] DAWN: Well, I'm sorry to say, Ashley, but you can't get rid of us that easily [laughter]. Thank you both for chatting with me today. If y'all want to stay updated, you can follow along on LinkedIn or YouTube. We do these live streams every two weeks. We also share incubator news and updates on our blog, so thoughtbot.com/blog. You can always go to the incubator site to understand a little bit more about the program. That's thoughtbot.com/incubator. Send us your questions if you have them. And you can always attend the lives, comment on the threads, send us an email. We love to hear from y'all. Thank you for tuning in AD: Did you know thoughtbot has a referral program? If you introduce us to someone looking for a design or development partner, we will compensate you if they decide to work with us. More info on our website at tbot.io/referral. Or you can email us at [email protected] with any questions.Special Guests: Ashley Sheble, Dawn Delatte, and Jordyn Bonds.Support Giant Robots Smashing Into Other Giant Robots