thoughtbot's Incubator Program Mini Season - Episode 04: AvidFirst with Ashley Sheble

Dawn Delatte, Vendela Colavecchio, 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 discussion covers various aspects of the program, including the evolution of the product idea, insights gained from industry conferences, the importance of listening to customers, and the ongoing development of the go-to-market strategy. Everyone emphasizes the value of the Incubator Program in helping founders connect with their market and refine their strategy. Just catching up? Listen to Part I, Part 2, and Part 3 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. So, since we have a bigger crew here today, slightly bigger crew, we should just jump right in, right? If you're not familiar with thoughtbot, we're a design and development consultancy who create and build products from the very earliest stages. We are currently in our second incubator session. This is actually our final week. We're wrapping up this week our second program with Ashley at AvidFirst. And I'll let everybody go around and say hi and give a little intro. Today, we're going to be chatting about how the program has been going, any new recent activity, and things that we've learned and done, and, you know, what's going to happen here after the session ends. I'm Dawn. I am a Managing Director here at thoughtbot. And I will shoot it over to you, Ashley. ASHLEY: Thanks, Dawn. And my name is Ashley Sheble. I'm the CEO and Founder of AvidFirst. AvidFirst is really focused on helping people save and spend for college in a modern way. We're simplifying the process, modernizing the experience, and really, with the end goal of helping families avoid student debt. So, I've been working with the thoughtbot team for the past eight weeks, really refining our strategy, and we'll talk about this here in a minute. But pivoting a little bit on the strategy just based on what we learn from the market from talking to users, from talking to experts, from talking to people with just insight around what's needed in the space. And so I'm excited to share more about the past eight weeks. DAWN: Awesome. Thank you. Jordyn, do you want to hop in? JORDYN: Sure. I'm Jordyn Bonds. And I'm the Director of Product Strategy on the Ignite team. And I am a two-time former co-founder of tech startups, so whence I come to this work. Vendela, I'll let you go. VENDELA: I'm Vendela Colavecchio. I'm the Design Director on our team here running the incubators at thoughtbot. And yeah, should I talk about my role on the incubator [chuckles] more? I guess the incubator is sort of funny because, you know, as a designer, typically, my tasks fall under more of a traditional design category. But I think with the incubator, we're, like, all hands on deck, just trying to get lots of things done and help out in any way that we can. So, definitely some design things, but also just a bunch of participating in discussions and getting all sorts of tasks done. DAWN: I'm sure we'll dive more into that. As usual, though, we're going to let Ashley kick us off, kick our discussion off with a little bit of an update on what's been going on in these past two weeks since we last chatted and, you know, where we are now. ASHLEY: Yeah. So, the past couple of weeks have been pretty exciting. I went to an industry conference. It was a 529 and ABLE conference. So, 529s are tax-advantaged savings accounts specific for education expenses. ABLE accounts are tax-advantaged savings accounts, specifically for people who have a disability. And so, spent a week learning from experts in both spaces, hearing from all the different stakeholders, so state agencies, program distributors, you name it, every sort of stakeholder in the whole industry was there. And it was amazing to just be able to go in and learn and meet people and hear their perspectives around what's going well, what's not going well. It could not have been more well timed because I think had the conference been earlier, I might not have been ready to ask the right questions from the different stakeholders. And had the conference been later, well, we couldn't have used any of that insight and learning to continue working on refining or pivoting the project. So, it was a great experience. People were so collaborative, so helpful. I think it's interesting that my perspective going in was, oh, people aren't going to want to talk to me. They're not going to want to share their insight. But it was quite the opposite. People were really happy to talk about what they thought could be improved or what they thought seemed to be going well. But it's only from one perspective. So, if you start asking questions around what you've learned from other people's perspectives, you kind of see this, like, aha moment. Like, oh, I hadn't thought about that before. Maybe that's something to consider. So, it was an amazing experience. So, as a result of that particular event last week, have really been synthesizing what we learned, filling in any gaps. And then just using that to think about a different strategy based on kind of the signals in the room, what people were really excited about, and what people really thought needed some work versus what we went into the conference thinking was the right answer, if that makes sense. DAWN: That's so exciting. Can you tell us more about this pivot? You mentioned a pivot. ASHLEY: Yeah. And I wouldn't call it maybe a full pivot. I would say it's more an expansion on the work we've already done, which is good. So, we're not just throwing away all the work we've done for the past seven weeks and saying, "Forget it." There are a lot of parallels in the 529 space and the ABLE space. A lot of the stakeholders are the same, and it's just a different target market with a little bit different need set. And so, really trying to understand what the differences are, and what the similarities are, and how we can replicate the work that we've already done for one space in the other space, and then build upon that a lot more rapidly than it took us to build the initial work for the 529. So, there's definitely some advantages that the two industries are really intertwined. But at the same time, there are some differences that we need to be keenly aware of and making sure that we're solving a problem meaningfully. DAWN: Jordyn and Vendela, how has this, not pivot, but new expansion or new strategy, how has this affected your work? VENDELA: What I'm thinking about on sort of a meta-level is how it's exciting to see that this new angle doesn't really change how we would approach the problem in terms of just running the incubator. So, it's almost, not in a discouraging way, but it's almost just like starting back from week one and kind of going through, what do we know? What do we need to find out? What kind of questions do we need to ask stakeholders, et cetera? And just seeing how having done that already together it makes it pretty clear what the path forward would be in terms of the process. In terms of information, who knows what we'll find out? But I think that's been exciting. The pivot doesn't feel so scary as it might sound [laughs]. JORDYN: Yeah, I would just build on that to say that it's giving us this really awesome opportunity to immediately run the same process that we just ran but, like, to see how much we've learned from doing it the first time. It's like you're starting over, but you're starting over from a better place, right? With more skills, way more understanding of sort of what's important and what's not important. And, you know, once you've run the process at least once, no part of it feels daunting, right? It just feels like work you know how to do, so it's like, okay, this is a really interesting additional sort of adjacent opportunity. We need to very quickly itemize all the things we don't know about it, and then figure out how to learn about it. Is it research? Is it interviewing? Is it testing? But none of those things feels unknown, right? It just feels like you get to do it faster and better. This is, like, a thing, you kind of can't convince someone without them having done it. And a lot of folks come to us, come to thoughtbot with a product idea. And we tell them like, "Okay, let's get in there and validate and invalidate things." And they're, like, "Invalidate? [vocalization] I don't want to invalidate my awesome, precious product idea [laughs]." And what we know that they don't know is that there are pieces that we're going to validate and pieces we're going to invalidate, but always you uncover new opportunities in that process. And you're just better and better at ascertaining what's promising about those things. So, it's only upside, but it feels like we're asking them to let go of something or to lose something, right? There's a feeling of like, it's like a scary...it's a feeling of like, I've built something, a tiny thing of value here, and you're asking me to risk that. And that couldn't be further from the truth. But it's, like, a really hard thing to convince someone until you've done it once. So, it's very fun, anyway, that we're getting to do this within one incubator cycle. Usually, it's, you know, it doesn't happen that quickly. ASHLEY: I like how you qualified that as fun. I will say...and Vendela and I were talking yesterday, and we were going through the sprints around, not starting over but beginning at the beginning with this new angle. And I was having the emotional rollercoaster of, like, what are we doing? Oh my gosh. And then, oh my gosh, this is so exciting. And then, oh my gosh, what are we doing? I feel very equipped now, having gone through this process once, to have the tools, the skills, the mindset to know, okay, it's part of the process. Here's what's going to happen. Here's what we'll probably learn. And just have a very structured way of approaching a new idea or a new angle, versus feeling like just thrown into the deep end and trying to figure out how to swim or which way is up. So, that's been pretty encouraging and eye-opening, too, that I developed all these skills that I didn't realize I had developed till we started redoing this, which is exciting. DAWN: I love that. It's kind of a testament to how valuable time spent is and how important it is to become really, like, more efficient with this process and the value of sort of rapidly being able to validate or invalidate different assumptions. I imagine that this might be a little bit different than what you expected. As Jordyn was saying, [laughs] most founders don't, you know, expect to have to loosen the grip on specific ideas. So, now that you're at week eight, how has this experience been overall for you? ASHLEY: It's been incredible. First of all, just the talented team that has been working on this project with me, I cannot say enough good, nice, positive things about that. I've heard horror stories about people working with teams that there's just a lot of dissension. There's lack of trust, all those things. And we had none of that, which is incredible. So, I feel very fortunate to have been with the team that I was with. I will also say that everybody had different strengths. And so, we're looking at an opportunity or a problem from a different lens in four ways, which is amazing because then you can cover so much more ground so much more quickly. I will also say, too, just the process: the thoughtbot program has for the eight-week structure is so intentional because sometimes I would think, well, wouldn't it make sense to do this thing before this thing? But just trusted the process, and the process was right. So, I would just say anybody that's thinking about going through the incubator or goes through the incubator next, just trust the process because you guys have a portfolio of success. You know what you're doing. I'm a testament to just really endorse the fact that each step is necessary in getting to the next step in a successful way. So, you're not taking two steps forward, one step back. You're constantly making forward progress. DAWN: That's awesome. What about you, Vendela, and Jordyn, how has this program and this session been this time around? VENDELA: I can talk about my experience as the first time going through the incubator, and then maybe, Jordyn, you have some insight on comparing the two or how you think it went in general. But I think one thing that has been really fun to do and participate in, and to Ashley's point about kind of having this environment of trust and just counting on each other that we're all distilling the information that we're hearing, I guess, accurately or in a way that aligns with how the rest of the team would perceive these things, is that we've had these really cool moments of not feeling like we 100% with complete certainty know exactly how something looks, but being creative about how we might get closer to that point. So, hearing a few tidbits here and there, thinking of ways that we're reading between the lines and interpreting that, and thinking about how we can narrow who we're talking to or approach the conversation slightly differently, so adjusting our script, or running some kind of other experiment, or structure things differently. And then, we might find that that angle wasn't exactly right, but by pursuing that angle, we learned something new that actually did get us closer in some way. And I think a lot of that was subtle throughout the process. But now, just thinking about this new kind of topic or pivot, whatever you want to call it [laughs], that we're pursuing, I think that lesson is going to be really valuable for Ashley moving forward, too, and just thinking, okay, I feel like what we're trying now isn't getting any closer. What have I heard that I could just grab, like, a small piece of string and pull on it, and see where that goes, and unravel something, and hopefully learn something new? So that there's just consistent kind of learning and not feeling like you're just totally blocked at any point. JORDYN: Yeah, to build on that a little bit, there's a real quality with this early work of just starting with what you have, where you are. And, you know, you don't have everything you need, like, you just don't, not in life and certainly not in [laughs] startup land. But the question is, like, figuring out what you need and figuring out how to get that from where you are. And that might be validation of a hypothesis you have, or it might be resources that you need that you don't have yet. And so, a lot of the work that we did together is to identify those things and to figure out ways to get them. And it's a real creative process because every problem is different. It's why it's really hard to talk about the programming in a specific way. It's like, you know, broadly, we're driving at the same outcomes every time. But every problem space, every industry requires a kind of different set of approaches, and, to me, that's really fun. It's like, okay, imagine as a metaphor, you know, that you are dropped from a helicopter into a jungle in Central America versus into Mongolia. Like, what you're going to need to survive in those two [laughs] environments is probably going to be pretty different, right? But that doesn't mean that your strategy for figuring those things out is going, like, the tactics you employ will be different. Yeah, I'm glad to hear, Vendela; that was a fun aspect of this. And sort of jumping off from that point, what was different this time? It's always different running this program. And every time, there's something new and different. But this was the first time we've run it with a FinTech product, and just learning about that ecosystem, the players, and the complex landscape of incentives and motivations, et cetera, was just, like, there was a steep learning curve for us at the beginning. And it was just super interesting and helpful to sift through that. It was like being, you know, dropped from a helicopter into a new sort of ecosystem. And we were like, all right, like, which berries are poisonous here? I don't know. But I also know that I need to eat something to survive [laughs]. So, it's like those kinds of questions, which is just super interesting. And then, what it always causes me to do is look at my own network anew. So, often, we find ourselves talking about, like, this question of starting with where you are with what you have. That includes with the network you have and the people you know. And it really depends on the problem you're solving, who you tap for what questions, right? And, suddenly, like, every one of these that we run, I get to turn to my own network. And I find new reasons to talk to different people about different things in my own network, which is really fun. It's like it allows me to get to know people in my own life in a new way. Like, every time this happens like, one of the first things we do is we turn to our own networks. Like, who do we know that has this problem or works in this industry, whatever? But having never worked on a FinTech product before, I didn't really need to do that with this lens. And it's like a whole new set of people lit up for me, and I got to have really interesting conversations with them. So, that was one thing that was different and really kind of fun. ASHLEY: It's funny to hear your take on the FinTech complexity because I feel like every time Vendela, or Jordyn, or Dave, who's not here, would ask me a question, it was, well, here's the answer, but if this, then that, or if this other thing, then that. It was never just a straightforward answer. And I was like, oh my gosh, they're just going to throw their hands up in the air at some point, but never did. They were just like, cool, that's fine. We'll figure out these different pathways, and if this, then we'll do that, and if this other thing, then we'll do this other thing. And I was just blown away by how nimble the team was and willing to just embrace the complexity. So, that, for me, was a huge positive. I don't know if you'll ever want to work in a FinTech product again; maybe yes, maybe no. DAWN: I would argue that we're more prepared now. You know, we've done a lot of FinTech work in the past, but applying this framework to understanding it as quickly as the team needed to, I'm sure, sort of pushed everybody farther, faster. So, Dave -- JORDYN: Yeah, I should say that was specific to me. thoughtbot has done plenty of FinTech work, Jordyn has not. But also, to your point, Ashley, like, I would love to actually. Now I'm like, oh okay, I kind of understand where the opportunities are here. I feel more prepared now rather than, like, more daunted. ASHLEY: Well, and you have a huge network in the FinTech space. So, that was something that was hugely helpful to me was talking with other founders who have been successful in the FinTech space, or people who have exited and had a great experience, or maybe people who have exited for, you know, reasons they didn't choose. But it was so important to hear from all those different perspectives and say, okay, here's what I would want to replicate, what I would definitely want to avoid. And so, anyways, just the network that Jordyn and others had and were willing to share with me was so valuable. DAWN: I was going to quickly shout out to Dave, who was sick this morning and wasn't able to make it. We were going to have him join. He was the senior developer in this sort of product pod that you've been working with. And I'm sure he has some interesting, more technical perspective to share. He did write a blog post, I think, maybe after week four, that I'm sure has some of those insights in it for folks who might be interested in reading from a developer's perspective. Yes, this is all wonderful to hear. I am curious to know what's next for AvidFirst. ASHLEY: Yeah, continuing on. There are a couple of things to pilot. And so, that's really the next step, pilot MVP as we think about this new angle. Because we want to make sure that the solution in mind is actually the solution that's needed. And so, those are the next steps, and then capital raise and then off to the races. So, if there's anybody listening that is interested in teaming up or wants to talk or contribute, would love to have a chat. DAWN: Is there anything that we can help with, anything on your mind, more network connections? [laughs] ASHLEY: Oh, gosh, offhand, I feel like I would be over-asking at this point because you guys have been beyond helpful. I really think the framework that I have to work with going forward—the team helped build a plan for here's what to do next, here's what to do after that, and here's what to do after that—is really setting me up for success as I think about continuing this journey without the amazing team day in, day out. JORDYN: Well, you have us as a team for life now, sorry. So, anytime you need something, [laughs] you can call. VENDELA: I was going to say I hope that you stick around in our Slack channel and update us on what's going on because now we're super invested, and we definitely want to hear how you're doing. ASHLEY: Yeah, absolutely. DAWN: Vendela and Jordyn, we've got another application window happening right now about to close for the next incubator session. Who should apply? What should they expect? JORDYN: Anybody with a business idea that involves software. The earlier, the better. And a lot of people, you know, come to us and are like, "Well, I have this idea that I'm kicking around for years in my head, but I haven't done anything yet. You know, what do I have to do to apply?" And we're like, "Sounds good. Apply." And then, other folks who are a little later, you know, and they feel like maybe they've hit some doldrums with an idea that they've explored a little bit. But they need a little bit of sort of reinvigorating and, you know, like a spark to get going on it. That's also a good time. We're really sort of excited to hear everybody's ideas. And the only, you know, downside is that we get more applications than folks we can work with. And there's always, like, a lot of great stuff in there. But everyone is encouraged to apply. You know, we used to have somewhat of a, like, non-technical founder. And when we first started, that was kind of the premise was, like, if you're a non-technical founder, we'll be your technical founding team. But I think we're finding that we kind of round out any skill sets in a way. If you bring a technical background, we can help you with the sales, and the marketing, and the business strategy. And if you come with those things, we can help you with the product and the technology strategy. It's the early-stage work, and the early-stage work is the early-stage work, regardless of your background. We can help fill in those gaps. ASHLEY: Yeah, I'll just add, too, I came in with this pitch check. I'm like, I'm ready to go, you know, we just need to build this thing. And, wow, the idea has changed so much since eight weeks ago. And so, I would just say, too, like, be open to feedback, be open to where the experience takes you. Even if you do have a really well-researched idea, there's always opportunity for improvement based on what the market says. And the market is constantly changing. And customer needs are constantly changing. And so, if you're not evolving with that experience, then you're going to get left behind or build a product for no one or, you know, a product for everyone is really a product for no one also. So, being open to the team's input and process is just invaluable no matter what stage somebody is coming into this with. JORDYN: That makes me just so happy to hear. And I will add that, like, I cannot stress enough that mostly what this program is for is to help folks connect with their market. Like, we actually don't want you to listen to us. We want you to listen to your customer all day, every day. How can you make sure you're moving with those folks, evolving with them, speaking their language, addressing the pain points that they have? Because that's why you're doing this, not because of what you think alone or what we think as your product pod. It's really what the market is doing and what your customer base is doing, and thinking, and feeling. And really, the programming is sort of geared toward helping people understand how to do that work. Like, you might conceptually understand that you need to do that. As a first-time founder, I certainly, you know, I had read the blogs, man. I knew I needed to be, like, customer-centric or whatever. But, like, I didn't really actually know how to do that. And once I did talk to some folks, it was a whole other new skill set to figure out how to listen for the things that mattered in what they were saying to me, right? Translating, you know, what folks are telling you and how they talk about their life and their work into product opportunities and innovation, it's a whole skill set that I, even coming into this work, you know, as a first-time founder with the background I had, I didn't have that skill set. You know, most people sitting out there would not argue, like, of course, you need to listen to your customer and move with the market, et cetera. But the question of, like, how to operationalize that [laughs], you know, is a completely opaque thing sometimes. Even for folks who have, like, done it before somewhat, it can still remain challenging. ASHLEY: Yeah, I feel in a better position now to continue keeping pace with the market. Because if you look at FinTech, historically, there were major innovations every ten years, and then that pace changed to every couple of years, and then it changed to every one year. And now you're seeing FinTech innovation accelerated to every few months; the landscape is different. And so, the solution today may need to be different in six months, or three months, something like that. But I feel like I have the tools now to keep up with that pace of change, whereas before, I would have been left behind. So, I feel really grateful for that. Thank you. DAWN: That warms my heart. We do have a question. So, does thoughtbot help with go-to-market strategy, or is the incubator more focused on zero to MVP? JORDYN: You know, I'm full of very spicy takes. Spicy take here: you're always going to market. Zero to MVP is different than go-to-market? I'm sorry, how? So, the answer is, like, absolutely. And really, what you're doing is perennially going to the market [laughs]. You're making a go-to-market strategy. You're keeping that fresh. You're keeping it new in the same way that you're keeping your products and technology strategy fresh and new, given what you're learning and what you're hearing. So, absolutely, I would say that's actually primarily what the incubator is for [laughs], and then making sure that those strategies are aligned. So, like, one of the things that I've seen in my own work at multiple startups, not just my own, is that those things can become disconnected as your team grows because people have different backgrounds and different...they just have a different focus, right? Your head of marketing has a different focus than your head of product and has a different focus than your head of technology. And keeping all of those strategically aligned and focused on the same customer and the same problem set is a lot of the work of an early-stage startup. And that's, like, a lot of the work that we kind of help founders figure out how to do. How do you tie your go-to-market to your MVP? Like, how do those two things fit in together, right? And how do you keep them in sync? It's not merely like you do this one time and then everyone goes their separate ways [laughs], and in 18 months, you meet back again and have a conversation about it, like, [laughs] not how this works. So, I mean, absolutely. VENDELA: I would add to that, too; I think something that we talk about with all these types of projects is just...and, internally, we talk about this a lot, too, like, we kind of hate the term MVP because it's so ambiguous really. Like, what does that mean for any given product? And so, I think, to your point, Jordyn, like, the going to market and the MVP are so tied together because the whole point of an MVP is to learn something so that you can then bring it from a minimum viable product to something more than that. And we talk a lot with founders about different approaches to MVP. I think some people have maybe a narrow view of what they can be. It's this, you know, maybe slightly lower fidelity but coded custom thing. And there's lots of ways to approach it that don't fit that definition and maybe would work better as a way to experiment and learn something, and then create a new version later on. So, you know, with that first version, you can still go to market, but you're learning something, and then you're maybe building a new MVP after that. And so, making sure that that's not too precious or hard to throw away is something, I think, we tell everybody, too. DAWN: Yes, that's great. Cool. Well, I think it's about time for us to wrap up. Thank you so much, Ashley. It's always an honor to kind of watch the team work with different founders and see them sort of learning as they go and seeing the product and the opportunities evolve. And it's been really great to be able to participate a little bit more this time and chatting with you and hearing about how things are going. I'm happy to hear that there was a lot of opportunity for you to continue exploring with AvidFirst. And we'll be here, so please [laughs] come to us as much as possible. Everybody is really excited to see, you know, you and this thing be successful. So, thank you, Vendela and Jordyn, as always, for being a wonderful team. If you're interested in applying to the incubator, do it. Don't hesitate. You can always visit thoughtbot.com/incubator for more information. And thanks 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, Jordyn Bonds, and Vendela Colavecchio.Support Giant Robots Smashing Into Other Giant Robots