Giant Robots Smashing Into Other Giant Robots

thoughtbot's Incubator Program Mini Season - Episode 01: AvidFirst with Ashley Sheble

November 1st, 2023

Lindsey Christensen is back as the Marketing Lead at thoughtbot! She's joined by guests Jordyn Bonds, the Director of Product Strategy at thoughtbot, and Ashley Sheble, a founder currently participating in thoughtbot's eight-week startup incubator, to discuss the multifaceted journey of entrepreneurship.

thoughtbot's Incubator Program aims to help founders like Ashley turn an idea into a viable product. They're currently at the stage of validating assumptions about the problem space and target market. Jordyn introduces a new concept: a project roadmap visualization that includes an "emotions workstream." This is designed to help founders anticipate and navigate the emotional rollercoaster often associated with the early stages of startup development.

Ashley finds the roadmap valuable, especially as it challenges her to examine her ideas from multiple perspectives. She appreciates the one-on-one support from the Incubator team, which complements her own expertise. She also speaks to the liberating aspect of acknowledging emotions in the startup journey, which is especially pertinent for female founders who often face additional challenges like lack of funding.

Jordyn emphasizes the importance of early and continuous customer engagement for product validation and innovation. She encourages aspiring entrepreneurs to talk to potential customers as soon as possible to iterate and learn from these interactions. Jordan and Ashley stress that embracing the logical and emotional aspects of entrepreneurship leads to more effective and grounded decision-making.

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LINDSEY: All right, we are live. So, thank you for joining us today. So, we've got a new founder that's going through thoughtbot's startup incubator. And we're going to be checking in with her as she goes through the program, learning what she learns, learning about the process.

Quick reminder: thoughtbot is a development and design company. We help founders and existing companies create, launch, and improve amazing products and their teams. And one way we do that is through our startup incubator. The incubator is an eight-week program. And our second session just kicked off, which we're going to be talking about a whole lot today.

So, I'm excited to introduce you to the founder that's going through that process, as well as our fearless leader of the incubator program, Jordyn, I myself, Lindsey Christensen. I'm the Marketing Lead here at thoughtbot. I'll be asking lots of questions. But if you also have questions, please enter them in the chat, and we'll get to those as well. Before we get to Ashley, I'm going to start off with Jordyn. For those who may not be familiar with you, can you tell us who you are and what you're doing?

JORDYN: I am Jordyn Bonds. And I am the Director of Product Strategy on thoughtbot's, Ignite team, which is the team that is kind of experimenting with this incubator, shall we say. And I am a two-time startup founder myself. I've worked at other early-stage startups as initial head of product. Long ago, I spent ten years as a software engineer. So, that's my distant background. And I live in Boston.

LINDSEY: Oh, we got our first comment. Someone says, "Thanks for sharing your experience." Thank you. Welcome. Love that. Keep the comments and questions coming.

Okay. And now for our latest guest of honor. Ashley, can you introduce yourself to the audience? A little bit about you and maybe even about your journey to bring you here today.

ASHLEY: Yeah, absolutely. So, hi, everybody. My name is Ashley Sheble. I'm currently based in Houston, Texas. I have about 15 years of experience in sales and operations roles. And I have two kids. I've got one who started third grade yesterday and one who started her senior year of high school yesterday, which is crazy. Time really flies by.

But the reason why that's relevant for this conversation is because I have attended so many college tours over the past few years and started learning about just how expensive higher education has become. I had no idea that a public four-year in-state school could cost $100,000 plus for just four years. And then, you start looking at out-of-state and private schools, and that number doubles, which is crazy to me.

So, after I got through that initial sticker shock, I was like, how is this possible? Like, now I understand why the student debt crisis is happening. And became really passionate about learning more about it and trying to figure out ways that I could help. Because obviously, the solutions and tools we have today to help people prepare for the education they or their children or family members need or want just aren't working. So, became really excited about that and working with thoughtbot as their second founder to explore this further.

LINDSEY: Amazing. So, Ashley, fighting the good fight. Student debt, I know, a topic near and dear to many people who are dealing with this. You mentioned your kid's journey to college is what started the idea. Let's dig into that a little bit more. How are you approaching the challenge, the problems that you see? Or maybe, like, how long it's been that you've been kind of playing around with this idea.

ASHLEY: Yeah, absolutely. So, I'm in a graduate school program and have used this as an opportunity to really explore different ways to attack problems. I became really interested in innovation and entrepreneurship at grad school and began just doing research, learning about ways to solve really big, complex problems, and found that technology could really be an interesting way to approach the student debt problem differently than what's been done before.

It's an industry that has largely lacked innovation, and have been working with professors and experts just to think about ways to apply technology to this really complicated problem to provide a more simple solution for people who just want to pay for school.

LINDSEY: And this is your first time being a founder. Is that right?

ASHLEY: It is. So, thank goodness for thoughtbot being my partner here because I'm not a technical person, meaning I don't develop software. I'm not a software designer, and knew that that was going to be a critical piece of developing a solution. And so, I'm grateful for the opportunity to work with Jordyn and her team.

LINDSEY: Have you, like, always thought you would, at some point, start your own thing? You know, have you always been entrepreneurial?

ASHLEY: Yeah, I think so. I can tell you my first business started in third grade. I launched my babysitting venture and marketed my services all over the neighborhood and church, and wherever would allow me to hang up a flyer, and had a pretty steady book of business, if you will. And in hindsight, I really cannot believe that parents allowed a 10-year-old to babysit their kids. You know, maybe in the '90s there were fewer questions–definitely less legal restrictions around age.

LINDSEY: The '90s were wild.

ASHLEY: The '90s were wild, yeah. Maybe I just seemed mature and responsible. I don't know. I don't know.

LINDSEY: Amazing. All right. Jordyn, so Ashley submitted for the thoughtbot incubator. What stood out to you in that application? And why did she seem like, you know, the right fit to go through the program?

JORDYN: Yeah, Ashley's application was just had that combination of prepared, done her homework, done the work to present the story well, but also clearly had a passion and a connection to the problem space. It wasn't just, like, a purely academic exercise for her, and just came prepared–really gave thoughtful answers in the application. There's a number of interviews that happened during the application process. She showed up with bells on and asked really good questions, which is something we always look for from founders as well. And she just knocked it out of the park.

ASHLEY: Thank you.

LINDSEY: And why was maybe where she is in her business or product journey a good fit for the incubator?

JORDYN: Great question. So, we sit at a really special moment, which is usually founders are coming to us, well, hopefully, founders are coming to us pre-product. So, they have not built a thing yet. They're basically at that moment where they've identified an opportunity. They've given it lots of thought, done a ton of research, maybe started talking to people about it.

But they're not sure how to take an idea, an opportunity, and what happens between that moment and innovation, actually a plan for a product, a strategic plan for product, and the ability to execute on that. There's a big gap there in understanding, especially for first-time founders. It certainly was a gap for me as a [laughs] first-time founder. That's the ideal candidate for us.

That said, we do have folks coming to the incubator who are interested in executing, like, a strategic pivot. Maybe they've found that the first thing they did was just, like, a market flop, and they basically want to do the programming. They're sort of starting over. Maybe they have a little bit...they're basically like, "Hey, we disqualified one idea. [laughs] We would like to come up with some other options." Those folks are also a good fit. And that is exactly the moment that Ashley is at. She's done a lot of great research so far–has a really interesting idea, interesting take on an interesting problem, but could really benefit from the programming of turning that into technical innovation.

LINDSEY: Which leads me back to you, Ashley. Can you tell us a little bit about your pre-thoughtbot research, like, both, like, how you approached it and maybe even some things that you learned that have helped you with your early direction?

ASHLEY: Yeah, absolutely. So, initially, just did a lot of industry research, just general population research, and then became a little bit more focused on solving problems for families in the U.S. right now. So, narrowing down that market scope.

And then, our focus right now is drilling into: how can we serve parents, students at each phase of their journey as parents or students, making sure that we are adding value as we're creating a service to help attack saving for college in a really effective way that is easy to do and is also going to help somebody be financially prepared to pay for a really expensive price tag without having to rely on student loans?

And so, we're doing a lot of focused research right now, building on what I did in grad school with professors and mentors and experts there, but being more focused and intentional around understanding each phase of the customer journey. So, whether you're a new parent, maybe a parent of kids that are a little older, or a parent of kids that are about to go to college or in college, how are we providing value at each stage of that journey? And so, we're really focusing in with customer interviews, understanding the pain points, and understanding what value is lacking as we think about building something that people want and like to use.

LINDSEY: In that early research, is there anything you learned or, like, positive signals you got as you were talking to people where it gave you a motivation to keep going, like, there is a good idea here to follow?

ASHLEY: Yeah, there have been some ideas that we're finding are just absolutely terrible, and they're just not going to work, which is good to know now before we spend a lot of time chasing something that's not going to be helpful. And also really finding some interesting patterns among conversations. We're digging in a little more where, initially, we thought, oh, nobody cares about that, or, oh, that's not a big deal. That's not a pain point, but actually, it is.

So, Jordyn, with her experience as a founder in prior experiences she's been able to use what she learned that maybe went well or didn't go as well as she had hoped and apply that learning to what we're doing together on this particular project. And so, that's super valuable, helps me avoid some rookie mistakes, and definitely prevents us from wasting a lot of time and resources that probably would have been wasted otherwise.

LINDSEY: Jordyn, can you tell me a little bit more about the kickoff, where we are? Because this is early, early days, where, you know, maybe a week in. You know, what does that initial kickoff with the founder look like? What are you doing?

JORDYN: Yeah. So, the first few days are really spent...we as a team on the thoughtbot side need to get to the place where we know everything the founder knows to date. So, it's very intense, a lot of, like, resource sharing, research sharing, conversations, a lot of elliptical conversations where Ashley will tell us something, we'll all go off and do some digging and some research, and come back and be like, ask her some questions, where she's like, [laughs] "If you recall, I said that to you," you know.

But, basically, it's one of those sort of processes where you don't know what you don't know. You start to understand. You come back, you ask questions, you dig. And the process is really about figuring out: where are the holes? So, Ashley has done a ton of really great work. She is but one person who has had divided attention. So, there are some places where we have some assumptions, all of us as individuals, and Ashley, specifically as a founder, has some assumptions about this problem space that we haven't validated yet. We haven't validated or invalidated. That's really what we're looking for.

It's like, is this hunch correct, incorrect? How do we know? So, we're really in those first few days are listening for those assumptions, for those untested assumptions. There's a ton of stuff in there where she's just like, I know the answer to this already. Here's what I know, and here's how I know it. Great, cool, validated, got it. But there's this other set of things that really then becomes the focus of the subsequent weeks of work.

And often, we find what those assumptions center around are early adopter market characteristics. There's the big vision, right? Which we don't doubt. Basically like, we do not disagree that paying for college is a huge problem. The student debt crisis is huge. There's a million ways to go about addressing that problem. How are we going to, from where we are right now, lay a pathway where we build value upon value? We find something valuable to give the market where it is right now, where we are right now, and then we build from that.

And so, you know, there's assumptions about who needs this, who wants this, who's struggling to pay for college, who's having no problem at all paying for college. But what we're trying to do is sort of zoom in on that group of folks, very tiny, specific group of folks who are having this problem the most acutely in a way that we are best situated to address. That's the magic we're trying to do.

So, it's really those early days are about listening to what Ashley knows, going out into the market, doing some research, follow-up research, but then really trying to come up with an early adopter hypothesis. And then immediately, as quickly as possible, interviewing as many of those people as we can so that we can validate or invalidate the assumptions we have about them. So, that's really the phase that we just started. Like, today and yesterday, we just started interviewing.

We have our first sort of hypothesis about...Ashley mentioned the journey of, like, beginning of child's life. Maybe, as a parent, I have aspirations for this child to go to college. Where do I start saving? You know, that end of the journey all the way to I am actively paying for a college education right now. Where in that journey are the pain points? And can we focus specifically on a particular group of people at a particular moment in that journey in order to provide maximum value right now and then expand from there?

So, we're doing a bunch of interviewing. I had a customer persona interview right before coming to this. You immediately start learning. There's just no substitute for it. The thing I tell founders constantly and I just sound like an absolute broken record, but you got to talk to people. You got to start talking to them now. You got to keep talking to them. You got to think hard and creatively about what you're hearing and who they are. And that's really the work that we're doing together right now.

LINDSEY: Exciting. [crosstalk 15:04] Ashley, I was going to say how is this kickoff then for you?

ASHLEY: Really good. One thing Lindsey and team have brought to the table, especially thinking about me working as a solo founder, is just around the fact that everybody has different perspectives. And we all have different expertise and different experiences that we're bringing to the table. So, the way that I've been thinking about a problem could be 180 from the way Jordyn's thinking about it or some other folks on our team.

And it's really interesting to have to really test a lot of these assumptions. I'm like, oh yeah, everybody thinks this way. Oh yeah, everybody does this. And it turns out I'm the only one, or maybe only a couple of us in the group are aligning with that perspective. And so, it has been so valuable as a solo founder to have a team of people researching the same problem from a different perspective. So, I just wanted to add that.

LINDSEY: No, that's a great one. And that is sometimes challenging, I think, for the founders. I don't know if you're finding this when you're just getting started. But as you go through the process, things that you have maybe held to be true or facts you end up finding out are assumptions, or maybe assumptions that are false. Which also reminds me of Jordyn: you were telling me something very interesting that you're doing during this incubator, which is founder emotions mapping.

JORDYN: [laughs] Yeah.

LINDSEY: What is this?

JORDYN: Yeah, we've got this project roadmap visualization. It's a Gantt chart. Y'all, it is a Gantt chart. And it basically just lays out, broadly speaking, what we're going to do together on what timeline. It helps us, together, visualize where we're going, where we are, and what we need to do in between so that we don't lose sight of that.

And this time, it was the first time that we added...we had this sort of insight that we should add an emotions workstream [laughs] because so much of the early stage is just an emotional rollercoaster because you are learning so much so fast. And if you're lucky and you immediately go into innovation, delivery, learning more, scaling, right? It's this very fast loop. And it's not just that you're learning stuff about your market really quickly. You're learning stuff about yourself and about the work. The learning curve is just really steep.

And we had realized that you end up going through this cycle of emotions that's pretty predictable [chuckles], and that's great, right? We want founders to know that their emotions...not only are their emotions, like, totally valid, we wanted to welcome them in a little bit more than we have in the past.

So, we added this little emotions work stream that was basically just like, hey, first week, first few days of kickoff, you're going to feel like a million bucks. You're like, yes, I know some stuff. I finally got a team working on this with me. To the moon, right? Like, you got this, like, very optimistic, exuberant kind [laughs] of attitude.

Immediately, you start hearing perspectives you hadn't heard before in your problem space. You start uncovering contrary evidence. We start talking to people. Immediately, you start to learn things that you didn't know you didn't know, right? So, up until this moment, you've just had some blinders on, and you're like, the path is clear, and it is amazing. I'm just going to motor my way to success.

And our process is about really taking those blinders off and figuring out what is actually around me on this road? Are there words of attackers coming at me from the sides? Like, I need to know those things, right? But what happens is you start to know what you don't know. And so, there's this dip. You start off very optimistic, and then you have a week or two of declining mood where you're mortified. You learn that you had some assumptions that are not valid. There's some other risks and things lying out there in the market. It's truly mortifying.

Maybe you learn about a competitor you didn't know about because you just weren't searching the right words, or whatever it is, right? That moment a lot of founders are just like, the moment I discovered my first real competitor, and I had, like, a panic attack, right? That happened to me.

But then you start to make a plan around those things, okay, cool. Like, maybe we need to differentiate ourselves. Maybe there is some more information we need to figure out about how to go after this, et cetera. And you start that slow climb of dealing with the new information that you have, right? And filling in those gaps [inaudible 19:22].

Then you start to climb out of the hole, right? You're like, okay, we got a plan. I got a team. We're doing the work. Awesome. You learn new, really exciting things. And then you end up back on that, like, high where you're like, this is so awesome. We have the best idea. And now we know everything there is to know. But no, no, you've just reached a new plateau [laughs]. And there are more things to be learned and more things...So, it's this really predictable cycle, and that's fine. That's good. You wouldn't be here if you didn't care about the problem space, right? If you weren't passionate about it.

And so, we really wanted to actually call that out this time and make space for it and put it on the map. Hey, we might be feeling this way right now, just heads up. That's okay. We're going to be feeling really great in a week. And then, the week after that, we're going to be feeling [laughs] like garbage again. It's okay. Because knowing that really makes you feel.

And it took me a long time as a first-time founder to realize that, like, my moment-to-moment emotional experience is...I need to make space for it. It is what it is. But it is not the story of my business. And it's a thing you just kind of have to learn after going through a bunch of those cycles. But, like, part of what we're trying to do with the incubator is help founders not fall in those potholes, not make the rookie mistakes, as Ashley put it.

And one of those rookie mistakes is thinking that the first time you identify a direct competitor, everything that you've been working toward for the last year is useless, and you should quit, and everyone thinks you're a fool, and, like, whatever crazy narrative you [laughs] have going on in your mind [laughs]. We're kind of here to be like, it's okay. This is to be expected: onward and upward. The hard work continues.

So yeah, it's very fun. At some point, we will publish a little version of this visualization with our little cycle of feelings on the bottom. But it reminds us to make space for them in the conversation when we are doing those check-ins. Like, here we are on this roadmap, and here's where our feelings may or may not be.

ASHLEY: Her recap for day one is spot on. I left that conversation; I walked out of my office and told my husband, I said, "Listen, we're going to solve the student debt crisis. We're going to." And he was like, "Really? Okay." And I was like, "Yeah, we are." And then, like, two days later, I was like, "No, we are not going to be effective at this." And then, the next day, I was like, "No, I fixed it. We fixed it. It's fine." So, being able to reference that chart is really helpful and validating for me as a person to be like: I should be feeling like this; yes, I do. Perfect, you know, I'm right on track.

And I think, too, as a founder, and especially as a female founder, you are expected to just keep it together. Maybe that's a self-imposed belief. But when you think about the fact that female CEOs only have about 2% of the venture capital funding, it's like, you know, why would I ever raise a red flag for myself by letting my emotions be part of the conversation or letting my emotions even have a place in the business I'm building? And so, for her to say, "Listen, no, that's a really important part of this journey; we need to talk about it and make space for it," is really liberating.

And I think, too, just when you think about what has happened with the pandemic and all the awareness around mental health and behavioral health, and making sure that we're making time for managing emotions has been more important than ever. We see the research that if you don't manage those emotions, they're going to manage you. So, find a productive way to do it. Work with your team and find support in a way that works for you or a productive way to just kind of get some stress out without having to just internalize everything because that never works out.

So, it's been really great to have her be able to bring that as part of our conversation and our project plan and make sure that it's a relevant piece.

LINDSEY: Very well said. And I'm so glad you did bring up that point about being women founders, and, you know, having more of a, you know, an uphill battle and feeling that emotions are a sign of weakness or a sign that you don't know what you're doing. We have more impostor syndrome because of these outside factors like lack of funding, you know, lack of support. So, it's really great for you to share that and hopefully inspire others. In fact, we got a comment: "Ashley, your drive and ambition to solve a huge issue in our country is so inspiring." Thank you --

ASHLEY: Oh, thank you.

LINDSEY: For adding that comment, folks who are following along. So, it sounds like, for you, the emotion mapping is a positive experience, where it's helping you kind of ground yourself as, even these early days, some assumptions are being challenged, or you're seeing some challenges in the business idea.

ASHLEY: Oh yeah, absolutely. Circling back to the thoughtbot team, couldn't do this without them in a really tactical and effective way. Because they have the experience and the skills that I don't have, and us working together on this same problem has been incredible.

LINDSEY: How did you come to get connected with the incubator and thoughtbot and submitting that application?

ASHLEY: Yeah. So, I'm part of the Harvard Innovation Lab, which is the innovation program at Harvard for all the students. And somebody was talking about this incubator program, and there are a lot of incubator programs out there. And so, initially, I thought, oh okay, well, this will be just, like, all the others and probably not what I'm looking for. But I did some research and looked at the website and read more about the program and thought, oh my gosh, this is exactly what I've been looking for and didn't know existed because it is that one-on-one support, and most incubator or accelerator programs you're one of many companies going through the process.

And so, the feedback I have from others who have gone through similar paths is it's great, and it's nice to have a cohort. But at the same time, you're largely figuring things out for yourself, which I was doing anyway. So, I was like, well, what value is that going to bring? This is a one-on-one experience. There's a team dedicated to working on this solution, problem, et cetera with me.

And I'm just so thankful that there are software developers and designers that are interested in helping me tackle this challenge also. So, that was really exciting to have other people also excited about the same problem but able to bring different skill sets to the table to actually bring this to life.

LINDSEY: Oh, that's great. Thanks for sharing. All right, so nearing the end of our chat here. Jordyn, what is next? I think we're going to check back in in a couple of weeks. What might those weeks include?

JORDYN: Well, as I mentioned, we really began customer interviewing...I say customer, and this is really...often, it means a lot of things. It means interviewing people who might be users, people who might be customers, people who might be partners in what we're building. And we are just going to learn so much so quickly. We're going to invalidate a lot of things. We're going to come up with new ideas. So like, we will be different humans with a different perspective on the world in two weeks, which is really exciting.

But really, so this effort is really about learning how to have your audience lead you. And it isn't about just listening to your audience. So, when they say like, "Make the button blue," you're like, "Okay, blue button, you got it." It's like actually hearing about their lives and their pain points and then innovating. They're not software developers, your audience typically, so they aren't solving this problem themselves. It's up to you to translate what you're hearing into something innovative.

I think a standard metaphor here or example–I guess it's more like a case study—is, like, the famous Ford quote that, like, if he had pulled people and asked them what they wanted, they would have said faster horses, not a car, right? So, it's like, you got to look at the landscape, look at what's possible, maybe new things are possible technically, right? And so, we can solve this problem better, a problem that we know humans have, which is paying for college, or, in Ford's case, getting from point A to point B quickly.

So, it's really our job to listen and let what we're hearing from the audience be our guide, but not just, like, sort of take dictation, right? And that's where the skill and having done this lots of times comes in. So, that's what we're going to be doing in the next two weeks. We're going to be listening very closely, iterating on the questions that we're asking and who we're asking them to. And out of that will emerge the strategically sound innovation path, and it never fails to work. I cannot stress enough that if you talk to [laughs] people and you listen to them, opportunities become very clear.

So, if any of you out there are nursing an idea that you've been nursing for a while, and you're like, I'm not ready to talk to people about it; I need to think about it longer, nope. Talk to people about it today, please. Will you screw that conversation up? Yep. But the sooner you have it, the sooner you'll screw it up and learn from it. The longer you wait, the more your assumptions build, and then it gets very tense and very wrong. And you could really think yourself off into, like, a very weird place.

So, I encourage you all to do your research; talk to people about what you're thinking, what you're working on, the people for whom it matters. And that is what we are going to be doing for the next two weeks, and then is what Ashley is going to be doing for the rest of the life of this company because you never stop. It's not a thing. You don't do, like, a customer research sprint, and then you stop. If you stop doing that, you stop innovating, and then other people in the market overtake you. Sorry, I feel passionate about this issue [laughs].

LINDSEY: No, that's good. That's a quick pitch at the end here for everyone to apply to the next session incubator. Start getting the idea and the research you've been doing together. This could be you. So, hope you'll join us again in two weeks as we catch up. And yeah, as Jordyn said, things are going to be...there'll be so many insights in that amount of time. I almost started laughing after I asked, like, what will happen in two weeks? Because I know it's going to be so different, you know, day to day you all are doing so much work, learning so much. So, I'm really excited to learn about that.

So, stay tuned with us here in two weeks. We'll also be posting updates to the thoughtbot blog: And just really looking forward to following along with your journey, Ashley. Thank you so much for joining and sharing today.

ASHLEY: Yeah, thank you for having me.

LINDSEY: Jordyn, thank you as always.

JORDYN: Of course.

LINDSEY: And thank you, audience. Everyone have a fantastic day.

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