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thoughtbot's Incubator Program Mini Season 3 - Episode 01: Knect with Josh Herzig-Marx

November 7th, 2023

thoughtbot's Incubator Program is back for a third round! This episode introduces founder Josh Herzig-Marks of Knect, and he will be sharing his journey from freelance work to joining the program and what happens throughout! So far, he appreciates the deliberate communication practices required for practical remote work, despite remote work already being second nature to him, and he understands the importance of proactive and transparent communication in a team setting.

One critical insight for Josh so far was the misconception surrounding the term "CRM" in personal relationship management. His moment involved mislabeling a survey, which led to confusion about the project's intent.

As the Incubator Program progresses and continues to scale, Jordyn expresses excitement about involving more teams with different geographic focuses. The goal is to foster a collaborative environment within the thoughtbot Incubator Slack channel, encouraging past and present participants to share experiences and advice.

We invite listeners who resonate with any of the challenges heard or have potential solutions to reach out! Our next Incubator episode will introduce our other Session 3 participants, Mike and Chris, founders of Goodz.

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LINDSEY: My name is Lindsey Christensen, and I head up marketing for thoughtbot. For anyone listening or joining who isn't familiar with thoughtbot, we're a product design and development consultancy that helps you make great products and help make your team a success.

One of the very cool ways we do that is with the thoughtbot Startup Incubator, which is a program that we launched this year and that Jordyn, who's with us today, has been heading up. What's up, Jordyn? And today, what we're going to be doing is catching up with one of the latest founders who's participating in the incubator and seeing what he's been up to since the kickoff over these last two weeks.

JOSH: It's been two weeks. It's been two really fast weeks.

LINDSEY: [laughs] Josh, could you give us a little introduction to yourself?

JOSH: Sure. I'm Josh. Hi. I've been in tech product management for, like, 20-ish years, 15 or so of those were in head-of-product roles. And a bunch of those early on were my own startup, where I discovered I was a pretty mediocre founder but really liked this product leadership thing. I had a very lucky exit, which I leveraged into a series of first product manager, first head of product, first product leader roles at a series of early-stage companies across a ton of domains: B2B, B2C, FinTech, mobile, Revtech.

And then, a little over a year ago, my partner and I got to do this thing we've been talking about for a while, which was we swapped who the primary parent was. We have two kids, two teens, 13 and 15, right now, so that's eighth grade and ninth grade. I wanted to take over primary parenting so that they could focus as much or as little on their career as they wanted to in the same way they had allowed me to do for the first 15-ish years of our kids being kids.

And if I were a better person, I would have found some kind of job that allowed for work-life balance, but I'm not. I have a whopping case of ADD, which we'll probably come back to later on in this conversation. And the way that I knew I'd be able to actually fulfill my responsibility as a primary parent was by retiring from salaried work. So, I did that a little over a year ago, last summer. And kind of keep me busy and occupied in between 8:30 in the morning, you know, school drop off and 3:00 o'clock in the afternoon school pickup.

And when I'm not doing shopping, and cooking, and lunches, and doctor's appointments, and dentist appointments, and orthodontist appointments, and play dates, and soccer practices, and basketball practices, and soccer games, and basketball games, and Bar and Bat Mitzvahs, and all the other things that we do, I built a very small niche coaching mentorship and advisory practice around founders, solo product managers, and first-time heads of product. And that's pretty much up until about two weeks ago what I had been doing with myself.

LINDSEY: That's a great update. I especially liked all the practices that you have to go to. [crosstalk 02:54]

JOSH: I do like practices. We went to a co-ed soccer game for my middle school kid. And it was the first time that the boys' team and the girls' team ever played together, and they got totally clobbered by this other team. And what I loved about it at the end was the kids weren't bummed. They were like, "That was really fun."

And, you know, for a lot of these kids, they've been friends since kindergarten. So, this is, like, nine years of being friends and playing recess soccer together. And they're not very good at soccer, but they just really love all playing together so much. And they just bring so much sportspersonship to the field. It was really a pleasure.

LINDSEY: Okay. So, you're doing all this fun primary parenting and going to all the fun practices. You've got a coaching business that you're working on as well. But there was this idea, this idea that's needling. What brings you to us?

JOSH: I think before it was an idea, it was a problem. And I knew this was a Josh problem. And the Josh problem was that I have a really big network, you know, built over the past, you know, more than 20 years of professional life. And, you know, one of the joke lines I have is that the solution to almost any business problem is found in talking to more people. I really value being able to, you know, call people up, message them, text them, email them, get together with them, ask them lots of questions, listen hard. And I try really hard to reciprocate, doing the same thing.

I don't know what your professional network looks like, Lindsey or Jordyn, over the past, I don't know, couple years, decade, however long it's been, you know. But what used to be email and LinkedIn, maybe, and maybe getting together in some local meetups, has really spiraled what, to me, feels, again, whopping case of ADD, completely out of control, right?

I have my LinkedIn network, which has not gone away, right? And now I'm a member of, I don't know, Jordyn, we share these a lot, a dozen different professional networking Slacks. Those are the ones that Jordyn and I share, probably far, far more than that, right? Product management ones, entrepreneurship ones, product marketing ones, engineering ones, tech company ones, ones geographically based for the Boston area, ones that are focused on things like climate change and climate tech. So, a ridiculous number of these.

And as somebody with some experience and the privilege to have some free time, it feels kind of like, I don't know, an obligation sounds too grandiose, but it feels like a nice way that I can give back is by participating and trying to be helpful inside of these. So, that's happened.

And Discord became a thing, you know, certainly, it had been a thing for gamers since before that. But since the beginning of the pandemic, Discord became a thing. I'm in, like, I don't know, a dozen different similar Discord groups. And I'm in WhatsApp communities, and I'm in Telegram communities. And in-person meetups have started to happen again.

And I found myself kind of losing control. I was telling people, whether, you know, over the phone, or in Zoom calls, or direct messages, that I'd make connections to them, make intros, and it was getting increasingly hard to do that. I was forgetting about people, you know, like, it's hard to remember to stay in touch with all of your colleagues when you move on from past roles.

And, you know, I would try to make connections to people to be like, okay, Lindsey, you know, you wanted to meet somebody else in marketing in the Boston area. And I remember that, like, six years ago, they worked at Rocket, and now they've moved on to something else. I can't remember what it's called. And, like, how do you, like, you know, page through your email and your Slack connections and your LinkedIn to find that person? And that was really hard, too.

So, I have ADD. My family would say that I'm, like, moderately functional. So, how do I achieve that? By creating systems for myself. And I did all the things which other people have tried to do. I built myself, like spreadsheets and Notion databases. I have an awful lot of, like, Notion databases now powered by forms. I'm like, just put your information in, and it'll appear magically into my database where I try to, you know, push the work onto other people. And none of it was really working for me. And that was kind of the genesis of the idea and then trying to figure out, is this a Josh problem, or is this a broader problem? That's kind of how I got started.

LINDSEY: Lots of people, lots of channels, not a lot of tracking or confusing tracking. And we chatted briefly before, you know, you were starting the program. And this really resonated for me. And I also ended up doing a user interview [chuckles] with the team about it.

JOSH: Yeah [laughs].

LINDSEY: Because yeah, in my role, and moving from different companies or doing mentoring on the side, and being in investor communities and marketing communities, it gets overwhelming for sure. And I feel the pain. And I've had the embarrassing moments of not remembering how I know someone or a conversation we had, or someone I really respect asking me for an intro, and I'm like, I don't remember anything about how I know that person.

JOSH: I mean, that was both gratifying and disappointing. Gratifying, like, oh, it's not just a Josh problem; we all struggle with this, and disappointing, right? And as I've had more of these conversations, just to realize, like, I know almost nobody who doesn't struggle with this. There's a few. There's a few outliers, a few weirdos, a few superheroes who are able to do this really well and who feel in control. And, like, literally, as they describe it, it sounds like...Jordyn, you're nodding, right? It sounds like a superpower as they're describing how they do this, how they kind of manage it.

JORDYN: [laughs]

JOSH: But for the most part, thank goodness it's not a Josh problem. The bummer is, nobody has, like, you know, the magic incantation, right? The spell or the secret or, like, the one weird trick, or the tool or, like, could I just give you money and solve this thing? And none of this really exists today. And that was kind of a bummer. I was hoping for, you know, better news that this was a solved problem.

LINDSEY: [laughs] Yeah. Jordyn, heading over to you for a minute, Josh applied for the incubator with this problem that he was working on. We had a lot of great applications, I think, for this session. What made you think or you and the team land on Josh as one of our session three founders that would be a great fit for the programming?

JORDYN: I'd say it was probably two factors; one is the stage. What's really tough was figuring out who's a good stage fit for us. So, like, what that means is you've identified a specific enough problem. You're not just, like, I want to solve world hunger or something, like, super broad. There's enough of a specific pain point or a problem that you're trying to solve that there's, like, we might conceivably make progress on it in eight weeks. But you're not so far along that you are basically like, "Hey, I've got the specs for an MVP. Can you just build it?" Which is, like, too late for us.

And part of that is a discovery mindset of, "Hey, I've identified this pain point. I think other people have it. But I am very open to how we solve the problem or learning new things about it, learning that it is a bigger need in a market I've never thought about," like being open to the things we might learn together. So those things: stage fit, mindset fit.

But, also, like, it is a problem that is addressable with software, right? thoughtbot's focus is software. Like, yes, we have worked on products that are not software products, but, like, our bread and butter is software. And my personal bread and butter professionally is software. So, is the problem on the table something that, you know, software is a big component in meeting the need?

So, it's, you know, it's stage. So, I guess it's three things: stage, founder mindset, which is this combination of having conviction but being open-minded, a very weird [laughs] thing to find in a person. And then, you know, can we conceive of a way to address this with software without jumping to a solutionizing? That's sort of what we're looking for, and Josh checked all of those boxes.

And I think, also, just had a problem that people really resonated [laughs] with, which is clear from [laughs] what Lindsey was saying and for me personally as well, I think I should [laughter] say. This is a problem I have. So, when Josh and I first talked about it, I was just like, yes, I would love to solve this problem. I also wish there was some spell, or incantation, or weird trick, or existing products, et cetera.

JOSH: We might have spent an hour nerding out over all of the things that we've tried, yeah.

JORDYN: The things that we've tried, emphasis on the nerding.

JOSH: On the nerding part, yeah.

JORDYN: Any of you listening [crosstalk 10:45]

JOSH: Or what if we get sneakier connect Google Sheets to this, like, really weird web query and [laughs] --

JORDYN: [laughs] Exactly. And then giving up because it's totally unmaintainable or, like, [laughter] impossible, yeah. So...

JOSH: Right. Oh, and it's all crap, too [laughs].

JORDYN: Right, right. So, if anyone out there listening is like, "Oh yeah, that's me," first of all, you're not alone. Second of all, please reach out to us. We would like to interview you [crosstalk 11:09]

JOSH: Or, if anyone out there is like, "Oh, I have this thing solved," right? If you got the solution, please reach out to us.

JORDYN: [laughs] Yes, also, please.

JOSH: You can save us six more weeks of work [laughs].

JORDYN: If you know the solution, definitely tell us. Anyway, so to your question, though, Lindsey, that's how this [inaudible 11:23], and it just seemed like a great fit along those lines.

LINDSEY: Yeah. So but, Josh, you mentioned...well, I think you kind of downplayed your founder history a little bit. But you've been a founder who had success, certainly a product team leader who has been very successful in the early-stage teams. What were you looking for from thoughtbot? Like, what attracted you to working with the thoughtbot team on your problem when you have all this kind of past experience already?

JOSH: I think there's probably three parts to it; one is I know a bunch of people in the thoughtbot team pretty well. In past roles, I have actually hired thoughtbot; I think it was twice. And I've referred a bunch of your current and past clients as well. Like, I'm just generally a big thoughtbot fan. I think I've even used thoughtbot products long before I even knew, like, Chad or Jordyn, some of your old products from, like, you know, the early 2000s. So, we're going really OG here. So, I knew thoughtbot really well and think really highly of everybody who I've interacted with there.

Number two is, I know, you say incubator, but, for me, the word that's really been resonating has been accelerator. It can be really slow the early, I don't know, weeks, months, years to go from an idea to, hey, this is really an opportunity. And I didn't want to spend weeks or years at this. I have a full-time job. It's, you know, taking care of the family. Like, that's what I wanted to be focused on. And if this was really an opportunity, I wanted to figure this out relatively quickly. And I love the fact that thoughtbot has this eight-week accelerating program.

And the third one is I had this...and, you know, not every assumption I came in with was one that I'm going to leave the program with. But I came in with the assumption that a lot of the risk was technology risk. I had a rough idea. I was quickly discovering this wasn't just a Josh problem; this was a broader problem, right? There's plenty of challenges beyond that, but it's good to discover that your problem is broad. But is it something which can actually get built and built relatively straightforward?

Jordyn here [inaudible 13:27] this all the time. You know, I don't like science project problems, right? And thoughtbot is really, really good at building software and partnering with somebody who could help to remove that kind of risk as a non-technical founder, as somebody with literally zero technical skills, I find that very, I don't know, comforting, exciting.

LINDSEY: Okay, writes down in marketing notebook: "Accelerator resonating more than incubator." [laughs]

JOSH: I wanted to get to the decision...incubator is a better word for it. But I personally wanted to get to that is this a good opportunity or a bad opportunity decision faster.

LINDSEY: To quickly validate invalidate.

JOSH: Right. I wanted this, like, I wanted to timebox this thing, and eight weeks is a nice chunk of time.

LINDSEY: Love that, yeah.

JORDYN: I want to just, like, flag here that, like, all of these words are very frustrating [laughter]. And we had a really hard time picking one.

LINDSEY: I know [laughs].

JORDYN: And we really actually, like, in literal terms, I think that program is way more, like, founder bootcamp than anything, but thoughtbot can't run a bootcamp without people thinking it's a Rails bootcamp, right?

JOSH: Yeah.

LINDSEY: [laughs]

JORDYN: Like, if we just said, "thoughtbot bootcamp," people would be like, oh, as a developer, I should go to this bootcamp, and thoughtbot will teach me how to be a better engineer, which would be totally reasonable from a brand standpoint, right? So, we were like, all right, not bootcamp.

And then accelerator typically comes with investment dollars, in my experience as a founder, and we don't invest cash in the companies that we work with yet. So, that was off the list. And that just left incubator, which, eh, like, I don't disagree that it's not the best word, but, whatever, we lack a good one.

JOSH: I'll tell you one thing. So, I'm involved with other things in this space. I'm based in Boston but for Raleigh's brand-new Founder Institute chapter, which I think is a great program. And I'm really proud of the, you know, first cohort of founders that are going to the program down there. And I love them. And I love their energy, and enthusiasm, and focus and that we at Founder Institute are providing them with value. I think we really are, or I wouldn't be participating.

But I wanted people to work alongside me. And I think that's actually one of the things which is really unique about thoughtbot's program. This isn't, like, you know, a bunch of other founders with varying amounts of experience working alongside you. This is, like, actual people who do things: designers and software engineers, developers who are working alongside you and learning alongside you. But it makes it, I would say, less of a lonely process.

This is one of the things I remember. When I founded a company, the one time I did this prior, I did it with my best friend, which is about as unlonely as you can possibly get. And it still is really, really lonely. Having this like, you know, team backing you up and a company backing up that team and organization is nice.

LINDSEY: Thanks for sharing that about the loneliness factor. That kind of reminds me, Jordyn; I know in the last session, you were trying out the idea of, like, this founder emotion tracker. Has that made its way to session 3?

JORDYN: Not really, mostly because both of the teams we're working with, two teams, by the way, not just Josh, have been founders before. And so, the emotional rollercoaster of, like, literally every day, you know, Monday, you feel like a million bucks because you have a really great idea, and you're really excited about it. And then, Tuesday, you talk to a bunch of people who add some complexity to the assumptions that you had [laughs] made on Monday. And then you start to feel like maybe this isn't a thing, oh no.

And then, Wednesday, you learn about some, like, technical thing that you didn't realize was a stumbling block. And so, by the end of Wednesday, you're like, everything is doomed. I shouldn't even be doing this. I've just wasted everyone's time. But then the team wakes up on Thursday and is like, "Actually, there's an easy solution to this. And we've found a new group of people to talk to who have this problem in a really clear way." And then you feel like a million bucks again. And then you just cycle through it.

Like, that cycle is something that Josh and our other founding team have actually felt before. And so, we haven't really been, like, leaning on the emotional roller coaster timeline as much just because it hasn't been as relevant. And that's kind of what's tough about the program we're running, which is that everybody comes to it with different assets in hand. I always think of that scene in The Princess Bride when they're outside the castle, and Westley is like, "What do we have? What are our assets?"

It's like you arrive to this with different assets in hand. You might have already talked to 50 people, but you have no technical background. So, you don't know what on earth to do about the information that you've learned. Or, you know, maybe you do have a technical background. And so, you've done a bunch of solutionizing, but you haven't talked to a single person about [laughs] whether they have the problem you're trying to solve. Anyway, it really runs the gamut.

And so, the programming is designed to help teams find focus and find market message fit. But what people roll up with is very different. In this case, we have a cohort, so to speak, that has some prior startup experience, especially as founders. And so, they know a little bit more about how every day is going to emotionally feel different. And that emotional rollercoaster workstream is on the roadmap. But we don't spend as much time with it as we did with Ashley and with Agnes before in the first two sessions because they were first-time founders and really didn't know how they should be feeling.

And that, to me, is one of the many value adds, including what Josh mentioned, like just having a team diligently focused on your problem space full-time is a huge boost of momentum and confidence. Just, like, people thinking about the same thing you're thinking about with you and bringing their earnest efforts to solving the problem has been one of the main things people have found valuable about it, in addition to the acknowledgement that, like, you're going to have a lot of different emotions. And it doesn't mean anything necessarily.

Like, your day-to-day emotion does not mean that you are a failure or that this is a bad idea or that you're a success, and this is a good idea [laughs]. Like, neither of those things is necessarily true.

LINDSEY: So, let's chat a little bit about what has actually been happening since kickoff. So, two weeks ago, started. Jordyn, maybe I'll start with you. What has the first two weeks of programming looked like?

JORDYN: We have been really heads down on interviewing. Josh rolled up having done a survey, which yielded a bunch of conversations already, conversations [inaudible 19:34]. So, we iterated on the scripts. You know, part of the efforts of the first couple of weeks are really geared toward having our team understand the things that Josh understands already. We need to kind of get on the same page.

And so, we try to talk to as many people as we can because there's nothing...One of our theses here, beliefs, I don't know what the right word is, is that there's really nothing that drives momentum quite like team alignment, and there's nothing quite like talking to customers and hearing for yourself what their pain points are. That drives alignment. So, it's like, everyone's talking to people. I'm sure people out there have been on teams where it's like one person talks to customers, and they're translating to everybody else. "Here's what I'm hearing. So, this is what we need to build."

And it's like if everybody has first-hand experience with the conversations, alignment and conviction sort of grows organically out of it. It's a lot less work to align if everybody's talking to people. So, it's always, like, the first order of business is, how do we talk to people so that we know the things you know to the level that you know them? So, we've been doing a ton of interviewing. And then, that's about driving alignment and understanding, but it's also ultimately about trying to drive focus.

So, as we are talking to people and listening to them, we're really trying to listen for patterns and to map those to the market segments these people inhabit. So, like, every one of us has our own network that we're bringing to this effort, and so we start there. And we start where you are with what you have, right? I think that's, like, a Teddy Roosevelt quote: start where you are with what you have. Somebody said that. Anyway, so we all do that.

But really, ultimately, we want to...building software is all about a repeatable problem that you can address with a one-size-fits-all [laughs] more or less product. What we're trying to find is, like, we're trying to listen for patterns and listen for pain points that are addressable and really focus in on a narrow niche or a situation context that we can address in some repeatable way. And I would say, at this moment, we've done a bunch of that interviewing. And we're now like, okay, we're feeling the need to focus, but we have not quite started that dive. I don't know, Josh, maybe you feel the same or different.

JOSH: No, I think that's right on. I mean, you know, the first thing we all had to do was develop our own [inaudible 21:45] understanding of the problem and the potential user, right? It wasn't going to happen from me talking to people. It was going to happen from us talking to people. And then, the next step is to start to align that empathic understanding, which sounds like a thing that gets finished, but really, it's only a thing that gets started and never really ends.

And then, you know, we got to be willing to make some bets, right? We got to figure out, you know, what is our hypothesis? You know, what do we think are the risky bits? And what are the things that differentiate this from being a problem? Where I think we have broad agreement across the entire team. And, literally, everybody we spoke to, the only people who don't think this is a problem are the ones who have some complicated, ridiculous system they built themselves, which they will acknowledge is not going to apply to anybody else. So, the problem is broad, right? But where exactly is the opportunity? Because at the end of the day, we're looking to build a business.

LINDSEY: Josh, I saw your head nodding during the alignment discussion. How has it been aligning with the team around the problem you've been thinking so much about?

JOSH: I don't know, Jordyn, how you feel about it. I've found it really fun. And it's been fun for a couple of reasons. I think the number one reason that I really like it is this is a really diverse team, right? So, Jordyn and I are in Boston and have; I would say, fairly similar tech company entrepreneurish sort of, you know, hand-wavy, miscellaneous tech people, startup folks background. We have somebody in Denmark, but she's Spanish. We have someone in maybe London right now, but he's Nigerian. And we have a member of our team in Saudi Arabia. That's a lot broader perspective.

And I think that comes to play in, like, at least three different ways. They come with their own perspectives, and their own world experiences, and lived experiences, and values, and ways they talk about those things, right? Number one. They come with their own networks of people to talk to you for whom it's easy to reach. So, it's not just all hand-wavy, tech startupy folks like I'd be talking to. And, like, literally, my entire list is, like, oh, they're all people like me. Like it was really easy to get 60 people to want to talk to me because they're all people I've been talking to for a while, which is awesome and maybe a little bit uninteresting.

But more than that, they all bring different language. Like, we've been struggling. Like, this is what we did. We spent what? Two hours of our hour and a half meeting this morning struggling with, like, are we having a difference, like, meaning or a difference of words? And it's not an efficient way to use your time, but it really is an effective way to use your time. Because, like, that struggle of trying to communicate what we're hearing and try to communicate what we're thinking and what we're feeling, I think, has led to a much better understanding of the problem and maybe even the opportunity than we would have had otherwise. I'm a big fan of struggle.

JORDYN: Definitely. And I do feel like there's an element of this where you can never understand your customers' problems in too much detail. It's like every pass we do at this, we kind of have a deeper, more granular, nuanced sense of the problems. And just in that conversation this morning, we, like, took a problem that we had understood one way and, like, were able to break it down, like, okay, what are the actual pieces of this? Oh, there's, like, many pieces of it, right? Like you said, Josh, it feels inefficient, or sometimes it just feels like you walk out of a call and you're like, what was that about?

And then only later do you find, you know, maybe when we are ideating, like, ways we might solve a problem, that conversation we had that felt really murky and, like, are we just arguing about semantics here? Are we arguing [laughs]...I don't know, like, however, you might frame that, like, actually becomes really important where you're like, oh, well, I'm very glad we took the time to break this problem down because now that we're trying to develop a solution, it becomes clear that there are many, little things we're trying to solve. And we can't solve them all at once. And so, it's great that we all have a fluent understanding of the details of that because it makes those conversations much faster so [inaudible 25:30].

JOSH: Can I say a nice thing about thoughtbot? I know this isn't, like, the, you know, [crosstalk 25:34]

LINDSEY: Please. Please do. Welcome, Josh. Yeah, the floor is yours.

JOSH: Let me say a nice thing about thoughtbot. The last time I did this, I did this with my best friend, Ben, a person I had literally known since I was six years old, maybe five, I don't know, since first grade. And we were entering a new space. This was, like, grocery marketing.

And we talked to a crap ton of people, a lot of them doing things like going to grocery store headquarters and just talking to people and meeting people who are, like, manufacturers of a grocery product and going to trade shows with 60,000 grocers all in one giant room. Remember those days pre-COVID? We would, like, you know, take the samples with your left hand and shake with your right hand, and don't get those two things mixed up because there's a lot of people in the room with you.

And we talked to easily 1,000 people, and we knew how to establish that, like, shared empathic understanding of the market and the problem really well because we were side by side. We were really well-practiced at having those conversations. And, you know, after the day of, you know, shaking hands, and meeting people, and introducing ourselves was done, we'd go back to the hotel room, shared, of course, because we were young entrepreneurs who couldn't afford to get nice hotel rooms. And we'd spend the next couple of hours, like, talking about it. We, like, talked to each other all the time.

One nice thing about thoughtbot is you're really good at working remotely and working asynchronously. And if, you know, it had been up to me by myself to be like, okay, you know, Josh, you have this, like, remote team in different time zones with, you know, non-overlapping hours. How are you going to, like, work together to establish this common understanding, this common semantic model, this common syntax for talking about the problem, and the users, and the needs, and the opportunity? I'd be like, I don't know, right?

And this is somebody who's, like, worked remotely for the past, I don't know, 5,6, 7 years, I mean, most of his job. But, like, still, that early bit is a thing, which, you know, I've seen a lot of thoughtbot practice and skill around. And it's not an easy skill to master. And it's one that you practiced organizationally. And that's really valuable. And I don't think I fully appreciated that until we got started.

LINDSEY: Oh, thanks. Jordyn, any thoughts on that? Were you thinking about remote setup of the program, or at this point, it's just everything is remote?

JORDYN: Working remotely can really deepen, in good ways, one's communication practices because it forces you to be intentional about communicating in a way that when you are co-located with people, you kind of don't have to because there's people in front of you when you talk to them. So, I agree, Josh, that thoughtbot does a good job of making that work, the work to communicate and stay on the same page, like, tangible, visible, whatever it is.

That's also just something I've given a ton of thought to because I've been working remotely, like, as a primary orientation since 2010. And so, this is just, like, how I work. And it's very; I don't know, organic to my mind now that it's basically, like, if I'm doing something and I don't tell someone about it, it's like a tree falls in the forest, you know, if there's no one around to hear it. If I'm working on something and I don't tell anyone about it, it's like I didn't do anything.

Communication is, like, 60% of the job. And the setpoint is, oh, I did something. Oh, I emailed someone. Maybe I should tell the team about this [laughs]. Just literally because you're not in a situation where I'm going to overhear a phone call that Josh is having because he's at the desk next to mine, or I'm going to, like, ambiently be aware that, like, Carol and Toby went into a conference room to talk about something. Like, while I maybe didn't consciously think about that, it's sort of in my periphery. Like, none of that is happening because we're not in the office together, right?

We don't get to do the thing that you did with Ben, where we just talk about stuff because we're near each other. So, you really have to get into this practice of externalizing very proactively the things going on in your own mind with the team. And it's a challenge. It's work. It doesn't just happen effortlessly, right?

But yeah, to say it's critical or to say it's a critical piece of how we approach the work is an understatement. I don't know, it's like, it is the work [laughs]. The making of the software, whatever, that's easy [laughs]. Communicating about making software that's hard [laughs]. So, I don't know, it's very heartening --

LINDSEY: Yeah, that makes sense.

JORDYN: To hear, Josh, that you think that we do a good job of that. I think we're constantly trying to do a better job of it, frankly. I don't know if you can do [crosstalk 29:28]

JOSH: That's probably why you do a good job.

LINDSEY: So, I know a lot of the early weeks, days has been around alignment and doing a lot of these user interviews. Have there been any moments yet, Josh, any new, like, light bulbs for you or insights, or are we not quite there yet; it's more kind of setting the scene?

JOSH: I'll share one really embarrassing one.


JOSH: Which keeps on coming back to bite me. When I sent out the survey and, of course, I [inaudible 29:57] for everybody listening, basically, surveys are useless, except they're really nice lead generation tools for people who are willing to talk to you. But when we sent out the survey, at the top, it says something like, "Personal CRM survey." And I'm pretty sure that when I set up the calendar invite system, which is, by the way, for folks listening out there, like, you want to get your, like, operational side of this thing done before you start sending emails out because you're going to quickly, like, lose the ability to keep track of stuff.

I think the meeting of it also, I said something like personal CRM survey. And it was, I don't know, sometime in the middle of the first week, maybe later on, when, like, I think we all realized on the team that, like, CRM is the wrong framing for this thing, right? Nobody likes CRMS [laughs]. CRMs are transactional. They're tools to sell something to somebody. You know, they are tools for, like, auditing your behavior if you're a salesperson to make sure you're doing what you're supposed to be doing. They're, like, on a cadence. Like, CRMs are tools for a world, which is not what most people aspire for their personal relationships to be.

And I don't think we've quite settled on what this thing actually is. And maybe there isn't a thing yet, right? Maybe that's part of the challenge that we're having, like, this thing doesn't exist, but it's not a CRM. And three-quarters of the way through the interviews is when I asked people like, "So, what question should I have asked you?" They all said, "Well, you didn't ask me about personal CRMs at all." I'm like, "Okay, that's a good point [laughs]."

So, there have been plenty of pivots inside of my head around this and the way that I think about this problem, and some of these things are still embarrassing and still kind of coming back to haunt me and maybe haunt the rest of the team as well. I don't know, Jordyn, what [crosstalk 31:27]

LINDSEY: Honestly, I was hoping for something way more embarrassing, but [laughs] --

JOSH: Way more embarrassing.

JORDYN: If that's your embarrassing...[laughs]

LINDSEY: Yeah, you're doing great. You're doing great.

JORDYN: You're doing great.

JOSH: Okay, the number of video calls where I'm not wearing pants.


LINDSEY: Okay, onto the next question, Jordyn –-

JOSH: Embarrassing or awkward, I don't know, yeah.


LINDSEY: Jordyn, you mentioned that Josh is not the only participant in this [crosstalk 31:52]

JORDYN: Great question.

LINDSEY: Tell me about, why not just Josh? What's going on? What are the developments there?

JORDYN: Yeah, this is really exciting. So, we wanted to scale this program from the moment that we ran single companies [inaudible 32:08] to start because we wanted to learn as much as we could in a kind of intense, focused way from developing a process and seeing what's valuable about it. So, this was always kind of on our minds to do.

And the way it worked out was just that there were two teams at thoughtbot ready and willing to serve. And we had, you know, anytime we [inaudible 32:28] the application window, we always kind of have a list of folks that we're excited about. We can't take all of them. But in this case, we had the two teams. And it also kind of fell in this nice way where we've got this team with a center of gravity, you know, GMT center of gravity, essentially. And then we have another team, which has more of a, like, U.S. center of gravity. And so, the timing kind of worked out.

And yeah, I don't know, it wasn't anything more complex than that. It's just we'd always been on the lookout for how we could scale this effort––bring it to more folks. And this was the first opportunity where it appeared like it would work out. I mean, TBD if it's working out [laughs]. We can decide at the end [laughs]. But it's very exciting. It's fun. And we're really looking for ways to help these teams collaborate, you know, we'll see how.

Everybody's in a Slack channel together inside of thoughtbot's Slack called thoughbot incubator. And our past participants are in there as well. And we're really trying to create an atmosphere where people can help each other, share tips, talk about what they're working on. There is actually some intersection between what Josh is working on and what the other team is working on, I think, just because, Josh, what you're working on applies [laughs] to a lot of people. I think it applies to these people, too. Anyway, that's [crosstalk 33:42]

LINDSEY: It's fun to see the incubator Slack start to build out and folks talking to each other, and more thoughtboters are trickling in there. Because, Josh, you mentioned you've been a client before and a thoughtbot fan in the past. And now you can officially live in thoughtbot Slack, too, and hang out with us 24/7.

JOSH: Still just a guest.

LINDSEY: [laughs]

JOSH: Only got my two channels. Can't DM you unless you're in one of those two channels.

LINDSEY: One [crosstalk 34:11]

JOSH: But yes, it is very exciting. This is better than snacks at your downtown Boston office.

LINDSEY: Yeah, that's great.

JOSH: I think I even added an emoji to Slack. I was pretty happy with that.

LINDSEY: Oh, nice. We've got a good custom emoji library.

JOSH: I mean, that's what we have for company culture, right? Is company emojis.

LINDSEY: To kind of finish this out here, Josh or Jordyn, do you have any calls to action for our viewers or listeners, maybe interviews or survey participants or anything else?

JORDYN: Well, certainly, if the pain point we described resonates for you [laughs], reach out. We would love to interview you. Or, like Josh said, if you actually have solved this problem [laughs] --

LINDSEY: Oh yeah, that was a good one.

JORDYN: Please reach out [laughs]. That would be amazing.

JOSH: But I actually meant that. So, like, hey, if you out there are a software developer, an entrepreneur, own a company that you think has really solved this, I would love to learn from that if you want to talk to us.

If you are a person who struggles with this and feels like you've tried really hard to solve this, I'd love to hear from you as well. You know, did you search for a tool? Did you ask your friends? Did you try to build something yourself? Do you still use that thing you built yourself? Did you try one of those CRMs? [crosstalk 35:26] Did you try a personal CRM tool out there, right? Clay, Dex, Monica, folk, if those names resonate with you, like, I want to hear, right? I want to hear about people who feel like they're doing this thing really well or people who don't feel like they're doing as well as they should but who feel like they've put, like, real effort into it.

LINDSEY: Great. Well, we're going to be catching up with Josh here every other week.

JOSH: Great.

LINDSEY: We'll have some updates on the thoughtbot blog. And in our alternating week, we're going to be catching up with the other founders going through the incubator. So, next week, we're going to chat with Mike and Chris. And y'all will get to meet them and hear a little bit about their journey and what's led them to validating their idea in the thoughtbot incubator as well.

JOSH: And strong rec people to tune in for that one. They are extremely photogenic and very funny, and they talk slower than me, too, so a greater chance for people to understand what they're saying. So, all in all, definitely tune in for that.

LINDSEY: That's a great promo.

If you want to stay up to date with the incubator or are thinking about applying for the next session, I think will be in the new year, you can go to And you can also sign up for email updates. And we can make sure to send you recordings of these interviews as well as the blog updates and then keep you up to date about when applications open and end.

Jordyn and Josh, thank you so much for joining today and sharing what's been going on in the early days. It's really exciting to follow along. All right, have a great day. Thanks, everyone, for watching.


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