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thoughtbot's Incubator Program Mini Season - Episode 03: AvidFirst with Ashley Sheble

November 1st, 2023

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.

In the third part of the Mini Incubator Series, they talk about user interviews, data analysis, and prototyping to validate ideas. They emphasize the importance of being open to user signals and adjusting their approach accordingly. They also discuss the upcoming weeks of the program and the goal of refining their story and business strategy.

Just catching up? Listen to Part I and Part 2 of the Mini Incubator Series!

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DAWN: Thanks, everybody, for joining. We're glad that you're here. If you've tuned in before, great, welcome back. You're probably familiar with thoughtbot; if you're not, we're a product design and development consultancy that helps make you, and your team, and your product successful.

We are currently running the second session of our incubator program, which is an eight-week program that takes you through a lot of different activities and exercises to help you identify market and product opportunities, experiment with them, and ideally come up with a solution that you can move forward with.

I'm Dawn. I'm a Managing Director here at thoughtbot. And I lead a team that works with very early-stage products, and founders, and companies. And I'll hand it over to Jordyn.

JORDYN: I'm Jordyn Bonds, and I'm the Director of Product Strategy on Dawn's team. And I'm kind of the...I don't know what, founder in residence for the incubator trying to bring my experience as a former founder to bear for our participants, in this case, Ashley.

ASHLEY: Okay, my name is Ashley Sheble. I'm the CEO and founder of AvidFirst and have been working with Jordyn and a great team in the second incubator session. So, removing all bias from the statement I'm about to say, but if anybody's thinking about applying to the next incubator, just do it. It's an amazing experience. You're going to learn so much. There are so many smart, helpful people who really care about building cool products that make a difference. And so, do it.

DAWN: I love it. Thanks for the impromptu promo.

JORDYN: Yeah, thank you [laughs]. It's good to hear.

DAWN: Yeah, I'm excited. Cool. Well, Ashley, why don't you maybe kick us off with a little bit of a recap of these past two weeks? What have y'all been working on?

ASHLEY: Yeah, so, just for a little background, in case anybody hasn't been following along, AvidFirst is a technology company aimed at simplifying college saving and spending. Our goal is really to make 529 accounts more usable broadly and then, more specifically, attractive to next-gen consumers.

And for those who aren't familiar with 529 plans, that's okay because neither are about 70% of Americans. But essentially, they are college savings vehicles. They're investment accounts that allow people to contribute money. The money grows tax-free and then can be withdrawn tax-free when used for qualified education expenses.

And over the past few years, the term qualified education expense has really expanded from beyond just tuition and fees to room and board on and off campus, computers, technology, supplies, apprenticeships, K through 12, like, the list is getting longer and longer. And so, our goal is just to really help simplify a really complex system and savings vehicle to make them more appealing and attractive to people.

So, the past few weeks, specifically, we have been aggregating all the data from our user interviews. We've done a lot of user interviews with different stakeholders and have been taking the information and saying, okay, what do we do next? How do we validate the way we're thinking about solving this problem will actually solve the problem in the way that we think it will? And so, through lots of process mapping, brainstorming different pilot initiatives, and then now working through some of the nuances of the industry. The 529 industry, specifically, is a complex animal. I don't really know how else to explain it. It's very complex. And so, we are just navigating these complexities and looking for solutions that will truly simplify the complexity.

JORDYN: I will just dig in a little bit to that analysis of the interviews that we've been conducting. That analysis kind of, like, stepped up a notch in the last week in a really fun way where we, the team, really kind of dug into the dynamics of each interview, sort of the things that we're most curious about, and have been asking and really, like, scored each interview. And then did sort of a cohort analysis, like, where are the trends with which personas?

We had already had some intuitions, and we just wanted to confirm with the data that we weren't deluding ourselves about what the direction was. So, that was a really, like, I think it was a really useful exercise and kind of fun to see. And what doing that helps with is our own conviction, but then it also helps us make sure that we are honing who we're talking to going forward.

Talking to folks is, like, so critical and is so not scalable. It is so time-consuming [laughs]. So, you want to make sure that you're doing it really strategically. So, it's sort of, like, every wave of interviews we do, we do a little more analysis. And it's, like, we finally got to a critical number where we felt like doing this data pass was going to be statistically significant. We had enough interviews to really focus the interviews we're going to do going forward. So, just to give a little, like, lens into how that's worked and how we've been thinking about it.

DAWN: I think we ask this question often, maybe every time, but I'm interested to see how it continues to evolve. But what was something that you learned these past two weeks that really surprised you or maybe even confirmed your hunches?

JORDYN: So, as often happens, when you start talking to a focus group of people who share a lot of pain points in their lives or their work, you end up with, like, a lot of trends. Like, there might be a thing you're asking them about that you're particularly focused on or curious about, and you want to focus your questions on that. But invariably, you're talking to a human being, and they're going to talk about a lot of different things.

And so, early on, and when we started interviewing people at the very beginning of this project in August, you know, we were very focused on college savings and spending. But an interesting thing, like, sort of trend that came up was also how much parents care about imparting, you know, some sense of financial responsibility in their young adults [laughs]. And we were like, well, that's interesting. Okay, let's, like, keep an eye on that. Maybe that's interesting to us.

And what has kind of surprised me in the last couple of weeks is how much of that has sort of solidified. This is not, like, a news flash, by the way, like I think [laughs]. This is, like, a thing. Anyone who has teenagers out there is like, duh, like, why is this shocking to you? But the way that it ties into college savings and spending, I think we found some really interesting connections and threads there that have only gotten stronger with the specific cohorts that we've been talking to.

So, I think that we, at first, had started as just this sort of, like, well, that's interesting, but we'll see where it goes kind of thing. And now it's, like, become a little bit more core to how we're thinking about just broadly what folks are facing, who we're addressing. So, I guess it wasn't, like, a surprise, but, like, the deepening of that signal, you know, in the sense of signal and noise, has been, like, really interesting to us, I think.

ASHLEY: There's a system thinking expert that talks about how changes in a field are rarely made by the experts in the field but rather outsiders looking in. And so, for me, that's amazing because I don't have experience as a technology founder. I'm working with others who are founders in the technology space, which is great.

But it does leave some question marks for us as it relates to building some processes and doing some pilot mapping, which completely overcomable because we're able to draw on resources from within the thoughtbot organization. And then, also, just network, people within our network. Jordyn seems to know everybody. I'll be like, "Do you know somebody in North Dakota?" And she's like, "Actually, yes, my third cousin's sister lives there, and I can get her on the phone." And it's just --

JORDYN: It's my first cousin. I will tell you, it's my straight-up first cousin.

ASHLEY: Well, there's always someone that Jordyn knows no matter where, it seems like, which is extremely helpful when we're trying to find experts to help us answer some questions. So, it's great to be able to work through problems in a very systematic way, using some of the strategies that thoughtbot has employed, I guess, over and over and can be applied to different industries. But it does help us find, what are the questions we still need answered? And then, who are the people that can help us answer these questions? And be very strategic about that.

JORDYN: I would add to that on the networking score. I think this is one of those things that first-time founders often struggle with. They struggle with recognizing who in their network is a valuable person to talk to in the first place. And then, they struggle with making those connections because it feels like you're asking people to do stuff for you, and that doesn't always feel great.

But really, your network, and where you come from, and the people you know and who care about you are one of your biggest assets going into this work. And it's important to take stock of those folks as early as you can and think about how to involve them. And often, they want to be involved. They're excited to have a way to support you and contribute their expertise or whatever else.

It's actually really transformed some of my relationships, like family relationships that I didn't necessarily have as...people I just discovered in my own sort of extended family who were doing related things to me. And we're much deeper friends now because we get to talk about that stuff all the time. And before I was a founder, we just didn't really talk [laughs]. So, just think through who you know and how they might be able to help you, and chances are they really want to. It's a very useful exercise. And it doesn't have to be super transactional. It can be a real bond builder.

ASHLEY: Yeah, I would say that's completely true, especially from my own experience. I don't like to ask people for help, generally. And so, asking people for their time and for their advice, I'm like, oh my gosh, why are they going to give this to me? What can I do for them? But it's really been amazing how generous people are with their knowledge, and insight, and their time.

I'm attending a conference next week for the 529 industry. And there have been so many helpful, kind people who are just experts in their field, leaders in their companies and are willing to talk to me about their experiences about what challenges they see. Because ultimately, you know, when a company succeeds and helps the industry grow, everybody grows and benefits from that. So, I hadn't really looked at it that way until Jordyn really encouraged me to just be, like, just call that person or just, you know, reach out. And sure enough, they were more than willing to be helpful.

DAWN: I imagine there is a sort of a bit of human factor here in that, you know, what you're giving to them is an opportunity for them to share, like, something that's, like, deeply important to them and that probably not a lot of people ask them about, even their day-to-day work. So, I imagine that can feel good, too, and maybe even sort of help them better understand [laughs], like, what it is they're doing.

So, you've definitely sunk into who to talk to. What about the how? Like, what are y'all doing now to try to continue validating that this is the right opportunity and that there's a product opportunity there?

ASHLEY: Yeah, so, really drilling down on those two cohorts that we mentioned a little earlier, specifically one of them, making sure that we are asking questions now related to this solution that we are thinking about, and more around their experience with similar type of products or similar type of solutions to make sure that we are thinking about building features or building process flows in a way that will integrate into the way they're used to doing things today so it doesn't seem like a new learning curve to, you know, think about adopting our product.

And then, also, just making sure that we are providing value, ultimately, because we don't want to just build something just to build something that we think will work for this group of people who told us that something is hard. We want to make sure that we're actually making something that's hard much easier than it already is.

JORDYN: Yeah. We've really, I mean, to build on that, we've gotten a little bit further into testing messaging, which is we think that we understand folks' problems and how they are talking about them, but we really need to validate that. And, you know, we have created some landing pages and are showing them to folks and getting their reactions. But we've also started doing a little bit of prototyping, which we hope to start showing folks soon.

And this is all just...a prototype, in this case, meaning this isn't, like, a clickable app. This is just, like, sort of a static design that appears clickable [laughs], think of it like a PDF with some links in it, and just showing that to folks and saying, you know, "What would you do here? How would you respond to this?" And it's just a really great way's fast. It's easy to spin one of those up and then get them in front of folks and make sure that how we're thinking about this is sort of broadly in the right direction.

It's so much cheaper to find out that we're thinking about this wrongly with something like that than with an app that we spent six months building and launching, ha-ha. Now, who's done that before? Not me, no, never [laughs]. I've never wasted a year building a thing. So, it's a really fun thing to do. And sometimes you can's not even, like, let's validate what we're thinking. Sometimes, it's really helpful to actually throw some curveballs in there on purpose to make sure we're invalidating the right things. So, it's really fun to be moving into that phase with what we know to be true and really getting closer to testing things out in, like, a real-world situation.

ASHLEY: It's somewhat surprising, too, what people are reacting to or not reacting to. The things that we thought people would be really excited about, they're like, "Eh." And the things that we thought are just kind of, like, filler on the page, they're like, "That's awesome." So, it's really crazy to see that juxtaposition. And then, you've got some people who will be like, "Huh, that's cool." And then, you've got some people who are like, "Can I sign up right now?" And you have to say, "We'll let you know when you can, but not right now." Just the differences are pretty surprising.

JORDYN: Yeah, and I'm glad you brought that up, Ashley, about, like, the stuff that you just kind of put on the page to make it look like a real page, and then people really zero in on it. There's just so much serendipity involved in this work. And part of the skill in making products is being open to the right things at the right time, right? You want to stay focused on your mission and what it is you're trying to accomplish. But you don't want to ignore, you know, if people are reacting really strongly to something that you thought was sort of ancillary, it's important to, like, take a beat and think about that. How does that fit in? Can we use that?

What you want to do is find lightning that you can bottle, and if people are not feeling lightning [laughs] about the primary thing you are working on but they are about something else, that's totally okay. I mean, the recent past of successful applications in software products is littered with stories like that, where people thought they were building one thing, and they just consistently heard about this related thing from their users. And they were like, well, why don't we just invest in that? It takes a lot of courage to stare in the face of that signal, the data that you're getting from people, and let go of the things that are not working and really embrace the things that are.

DAWN: This reminds me a little bit of the conversation we were having when we were together in New York last week around the focus on validating or invalidating. The conversation we were having was kind of trying to shift that away from ideas to assumptions. But this is making me think that it focuses too much on one single thing that you're trying to get an answer for, as opposed to, like you're saying, being open to sort of receiving signals about completely tangential things or things that you may have not been paying attention to before. So, that makes a lot of sense.

ASHLEY: Yeah. Now I'm thinking, like, should we put even more crazy things on the page and just see what happens? Who knows?

JORDYN: I think there's another aspect of this first-time founders often struggle with, which is that feeling that you shouldn't put anything on the page that you're testing that you couldn't actually do. And it's tough. It can feel a little bit like you're misleading people. But there's absolutely ethical ways to do this, where you tell people, "Hey, this is just an idea. We're just trying to get people's gut reactions to this. We have not even put pixel-to-paper here. We don't even know. We just want to get your reaction."

As long as you're transparent with folks about where you're at and about not promising them things you can't actually do, I mean, obviously, if it were as easy as just promising stuff to people of what they want, we could just make a landing page that said, like, "Free bag of money. Who wants free bag of money," right? [laughs] And people would be like, "Why is the bag of money free?" [laughs] Right? And so, you really want to be careful and not necessarily do anything that is misleading.

But on the other hand, there's no better way to get folks' emotional reaction than to put something together and just see how they respond to it. So, there's a lot of, like, sort of nuance to doing this. And, Dawn, to your point, the balancing act between being open and being scattered, right? That's a fine line. I've definitely been on teams before that are just, like, the new hotness every week. "Hey, there's this cool app out. Let's just immediately redesign everything to look just like that." And you're like, "Maybe? [laughs] I don't know if that's, like, the best idea."

So, it's a real balancing act, but it always comes back to who you're building for and what they want and need. And if you're staying very focused on that and measuring, you know, comparing every idea anything that comes your way against those, showing it to them and getting their reaction, you can't fail. Keeping no daylight between yourself and your customer that is the surest path.

DAWN: Yeah, it kind of carries through to the core thing that we're saying, which is don't focus on one thing to validate or invalidate. Be open to receiving signals from other, you know, opportunities. But that's not validating or invalidating something. That's showing you where to focus your time. And then the product experiments and feasibility research and all of that is designed to help you to get closer to validation.

But, in some cases, there's a point at which you have to take a risk, right? And your customers are ultimately going to tell you over time whether or not the solution was the right one. But you get more confidence. You get closer to the right solution the more strategic you are about that process, so...oh, go ahead.

ASHLEY: I think the great thing about technology, too, is it's not set in stone. You can change it. If you learn something new, you can modify what you're doing to fit what you're hearing, and I think that's so incredible. We live in a time where there are so many tools and resources out there to really be nimble. And just to Jordyn's point earlier, I think the hardest part is being willing to take in some of these signals and be like, okay, this is what they want, and being willing to move in that direction versus the path you have already designed in your head.

DAWN: Yeah, we've only got a couple of weeks left in this incubator [laughs]. How are y'all feeling? What are you planning? What are you looking forward to over the next couple of weeks?

ASHLEY: I can't believe that time went by so fast. I thought eight weeks felt like two years when we first started. I was like, oh, we've got so much time. We're going to do so much. We have done a lot. But the time has really flown by. So, I'm just kind of, like, now thinking about how do I make the most of the last few weeks? And just make sure that we check all the boxes that we set out to check in the beginning, and then have a plan from there in terms of continuing the work in a productive and, you know, exciting way.

JORDYN: Yeah, one of the, like, sort of Northstar outcome for us in the incubator is to give the founder confidence in what they're doing and their path, the confidence in that vision, and then enough confidence to articulate it consistently to the folks they need to sort of bring along with them. So, what I'm, like, really looking forward to in the next couple of weeks is honing that story for Ashley. Like, what's your story? What's your why? What's your how? What's your when? And how to make sure that story is just easy to communicate.

I mean, already, Ashley, like, up top of this exact livestream where you articulated sort of, like, what AvidFirst is doing, I think I feel better and better about that articulation given what we know. It feels really good. It feels solid. And as we're going, we're just as skeptical as anyone else, right? But we're trying to anticipate what folks...external stakeholders broadly define what their misgivings are going to be. And we're compiling a kind of list of frequently asked questions about what AvidFirst is doing, like, why 529s? Why next-gen consumers? Et cetera. Just so that that story is so internalized that, like, you can't really be taken off guard necessarily.

I mean, you want to be open to new questions and new ideas. That's not what I'm saying. But just basically, like, being able to thoroughly and deeply, at the drop of a hat, to sort of pitch this to your dentist while they're cleaning your teeth, you know, like that kind of conviction and, like, the solidity of the narrative is really what we're going for in the next few weeks.

And I think we're well on our way there. We have all the pieces. It's about putting it together coherently, I think, at this point. It's really exciting, though. I do feel like we're really zeroing in on a valuable lens on college saving and spending that I think the market is really ripe for, so it's exciting.

DAWN: Yeah, it's been great to see all the progress. We have a comment that I just noticed.


DAWN: Not a question, but I wanted to call it out because it was related to what you were talking about a few minutes ago, Jordyn. Kiran said they totally agree. "We had the same epiphany/pivot this summer. We went from direct-to-consumer to an enterprise model. Try to zoom out with a systems thinking lens, and it will help with a clearer path and tell your story."

JORDYN: Yeah, that's awesome.

DAWN: There are no other questions from the audience. And it seems like maybe there's still a little bit of a lag. So [laughs], we can wrap up. If anybody has questions after this, feel free to comment. We'll be, you know, checking out the posts on LinkedIn and YouTube. And we can follow up there.

You can always, like I said, come and follow along. Check out our incubator site. You can both apply to the next incubator session and sign up to hear from us in our weekly newsletter. We write about progress on our blog as well, so There's all kinds of ways to find us and actually talking about the work that we're doing. So, please follow along.

JORDYN: Anyone out there who's wondering, am I right for the incubator? Just apply. It's really, like, nothing is too early if it's just an idea you've been kicking around that's born of your industry experience or your personal experience. The application process is really lightweight. This is not going to take you days to fill out this application.

We've heard from folks that even filling out the application is the first thing they ever did with regard to the idea, helped solidify it, and solidify their thinking for them. So, just go apply. You got something? You got an idea for an app? You see a growing market out there, and you feel like it's underserved with software? Just holler at us. We'd love to hear it. Apply. It's fun [laughs].

DAWN: Yeah. Thanks, everybody, for tuning in. Thanks, Jordyn and Ashley, for participating. See you again in a couple of weeks, yeah?

JORDYN: Yes. It'll be the last week, so we'll have things to say, no doubt.

DAWN: Yes, tune in. It'll be a good time. All right. Thanks, everybody.


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