Giant Robots Smashing Into Other Giant Robots

451: Product Strategy with Jordyn Bonds

December 1st, 2022

Jordyn Bonds is the Director of Product Strategy at thoughtbot. Jordyn helps companies validate new product opportunities and reach that first key milestone, from validating an early adopter market to creating a pitch deck to building a prototype, proof of concept, or an MVP launch.

Chad talks to Jordyn about what a Director of Product Strategy does, how Jordyn's career has evolved (She got to build for the Confessions on the Dance Floor release and tour!!), and finding practices that keep you motivated and inspired to be working towards long-term, large goals.

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CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Jordyn Bonds, the Director of Product Strategy at thoughtbot. Jordyn helps companies validate new product opportunities and reach that first key milestone, from validating an early adopter market to creating a pitch deck to building a prototype, proof of concept, or an MVP launch.

Jordyn, thank you for joining me not only on this podcast but at thoughtbot.

JORDYN: Thank you. It's wonderful to be here.

CHAD: You joined us in September of this year. And it's been really fun to watch...well, let me say it's always fun to watch people come into the company and begin to digest everything that's there, begin to, like, okay, I can see how this is working, and then to start to make your mark on things. And so thank you for everything you've done so far. And I look forward to seeing everything in the future too.

JORDYN: I look forward to it too. It's been a super interesting experience. I think thoughtbot has a really unique culture, and it's been really fun to get on-boarded into it.

CHAD: Cool. I'd love to talk a little bit more about that in a bit. But you have joined us as the Director of Product Strategy, which is actually a new position for us in the Ignite team, which is the team that focuses on those early-stage ideas, products, companies. Obviously, if we added the position, we thought it was important. We don't take those things lightly. What led you and made you perfect for that position?

JORDYN: [laughs] I think taking something from a nascent notion, whatever that is, an idea for a product or newly identified market opportunity to that first concrete thing out in the world is a really special phase of the work of new product launches. And it is, over the course of my career, just the thing I have really zeroed in on professionally over time. That's kind of my wheelhouse. And so I think that's thing number one. But what makes it special is that I like to think of it like it's almost like the first few seconds of the existence of the universe after the Big Bang...

CHAD: [laughs]

JORDYN: where you are inventing the ground rules of the thing you are building as you are building it. And that is a's just a really special time. And some people love it, and some people despise it. There's a lot of chaos and uncertainty, and you have to move forward despite all of that chaos and uncertainty. And some of us love the; I don't know, there's just this feeling that anything is possible, a sort of sense of newness and really paving the road while you're hacking through the jungle, and I just love that.

And I feel like I want to help other companies love that phase too. [laughs] It's like a weird thing to say. I'm almost like an evangelist for that time. But I'm an evangelist for it because I feel like it's really important to make sure that you're tying the mission and vision of the business; you're weaving it into what it is you're doing in the product ASAP. Do it early. Make sure you're thinking about this stuff from the jump. And if I can be an evangelist for that kind of thinking and the processes that make it possible, it's just a really exciting thing for me to be able to do.

CHAD: That's really cool. You saying that made me think about this sense that I have that oftentimes when you're faced with that period of time where everything is possible, and you're literally defining what the product and the business is going to be, maybe there are more than two buckets. But I think, generally, people fall into one of two buckets. There are the people who look at that and say, "Okay, here's what we're not going to do." And they're really good at saying no to things and narrowing down from that. Another group of people who maybe even really struggle with all of the possibility, and their reaction is to say "Yes," to everything.

JORDYN: Right. Yep.

CHAD: And you can probably say judged by the way that I introduced the concept which one I think is better.

JORDYN: [laughs]

CHAD: But that's the two buckets I see. Do you see that too?

JORDYN: Oh, absolutely. And I will say partly why I am so enthusiastic about this phase is that I was a bucket number two person and worked very hard to become a bucket number one person because that's the mindset you have to get in. But it's a real delicate balance. It's not always clear; you have to be open to things changing. But saying no is way more important than saying yes in the sense that, you know, I think the phrase people like to use in startup land is you can't boil the ocean, and that is true.

So it's much easier...the path is much easier and clearer if you start small. But if you're an entrepreneur, by nature, that's going to feel really uncomfortable to you because what you see out in the world is possibility and probably endless possibility, right?

CHAD: Right.

JORDYN: So the notion that you are going to squeeze yourself into the tiniest space to start when you see the giant opportunity. And PS, everyone is asking you to articulate that giant opportunity. You need to be able to tell that story so that you can recruit people to your cause. But at the same time, you need to be ruthlessly focused in the here and now on the small things, like, the constrained things you're going to do, for now, all the things you're going to say no to for now while keeping your eyes on this larger, expansive prize. It is just a's an art; it is a hard thing to do.

CHAD: How did you shift your mindset?

JORDYN: Through failure.

CHAD: [laughs]

JORDYN: It was through painfully failing at doing this. [laughs] I made every textbook mistake, some of them fairly recently. [laughs] So there's a lot of folks out there who their first venture, their first foray into this world, was a success, and that's wonderful for them. That's great. But their advice is sort of suspect for me and for a lot of founders because it's like, well, you didn't... [laughs] maybe it was skill, maybe it was luck; it was probably a combination of both. Like, good for you that you did this.

But if you've started a business, launched a product one time, and it was wildly successful, how are you in a position to teach me who might be on failure number two, or three, or whatever, how I need to change in order to be successful, what needs to change in order for me to be successful? Like, you're not going to be that useful to me. And so I find I'm in a much better position to help other people not fall into the same potholes that I did because I fell into them.

I can look at folks and say, "I know what you're thinking. I know you've got your eyes on this large market opportunity. And you can see the mass market future ten years from now for this thing that you're building, that's great. But you have to start with the narrowest of early adopters." And you have to start with a pain point that is, quote, "hair on fire" is another phrase people like to use, like, just some pain point that people have that is just so painful for people right now that they are willing to pay someone to fix it.

You got to focus on that despite this large, open-ended opportunity that's in the future. I can only really give that advice to folks credibly because I have done the opposite so many times that I can both empathize with where they're at in that impulse to boil the ocean, but I can also tell them how one way of disabusing yourself of that mindset.

So I think back to I have an older sister. She was really terrible at math when we were younger. [laughs] And she was the best math teacher for me because it didn't come easy for her. Going to someone who's a math genius to help teach you what greater than or less than is is [laughs] not going to help you because it's self-evident to them. Like, how are they going to break that down for you? My sister was a great math teacher for me because her understanding of math was quite hard-won. So if I came to her and said, "Hey, I don't understand greater than or less than," which, PS, is truly what happened.

CHAD: [laughs]

JORDYN: I was like, I don't really...however, it was being explained to me did not [laughs] resonate. She was a great person to go to because she would not judge me for not understanding it, first of all, and she would have ways of breaking that down. So I'm that person for new founders, people just starting out trying to come up with a new product or explore a new opportunity. I have learned all the painful lessons on their behalf. So it's not like I'm coming to them with advice; that's just boilerplate advice I have read somewhere, and I'm now repeating to them. No, I have painfully learned these lessons. [laughs] Let me help you avoid that.

CHAD: And you said it used the phrase like not now or not yet. And I think that's a great way of just doesn't mean no forever. [laughs] It just means not right now, not yet. Now's not the right time.

JORDYN: Exactly.

CHAD: And I think that's a healthy way of reframing it. You're trying to strike that balance between the opportunity and the future and what you're doing today to make the product successful and get it out the door.

JORDYN: And you can do a lot of work around those bright, shiny, attractive future possibilities that make it can basically say, "Not yet, and here's what will have to happen for it to become now." You can kind of nurture those opportunities over time, and what will be the criteria to make them something you want to pursue now. It can kind of sate your desire to pursue them if you nurture the plan over time. So it's not like you just say, "Not yet," you say, "Not yet, and here's the evolving set of things that will tell us it's the right time."

And having that shared alignment on the team around what those things are but keeping your eyes on them, actively monitoring the situation to be on the lookout when now is the time can satisfy your urge to be working toward that. I think that's what's really hard for founders who really have their eyes on this big opportunity is you can sometimes feel like you're not making any progress toward it because the progress is so incremental.

So finding those practices that feed that thing for you, that keep you motivated and inspired to be working toward that long-term large goal, finding those ways to keep at it, to see the progress, keep refining why it is you're doing what you're doing and how it is you're getting there, can make you feel like you're pursuing and even when you're not [laughs] if that makes any sense. I just acknowledge that people need to do something. Just telling yourself or your team not yet is sometimes not enough because you're in it for that big vision, right?

CHAD: Right. Yeah, that's great. One of the things that stood out to me when we first met was the variety of different experiences that you've held, different positions, different roles, different things you've done. You started doing web development. You've done user experience, product management, you've been CTO, you've been CEO of companies. You did product lead and VP of product. That variety of experience, I think is more than I have. [laughs] You have held those different roles. How has that evolved for you in your career? What's been driving that forward for you?

JORDYN: I was always this product strategy person inside. I didn't necessarily know it. I didn't really even know. I mean, back in the early days of the web, a product mindset wasn't even really a thing, and advertising got a hold of the internet first. And so it was really about graphic design for a long time and a bunch of other things. But throughout that first decade that I spent as an engineer, as a front-end engineer, I was just constantly that annoying person on the team who was like, "Why are we building this? Who are we building it for? Why are we building this?"

Because what I learned is as much as I liked to code, and I liked the puzzle of solving the problem of how to turn a design into a thing people could click on, that was really fun for me, but it was only fun for a while before I started to become really sad, disappointed that we would launch things that would be market failures in the sense of, yeah, we launched a thing, and we checked the box, but no one was using it.

And I would come back and say...and I was mostly doing agency work at the time, and so there was not a lot of follow-up. We'd launch something, and then it was, like, move on to the next project. I wanted to know, was this successful? Did people use it? Are people using it? Like, how are they using it? Is it easy to use? And I wanted to answer those questions. And then, when I started to do more of that follow-up work, and then I was finding that most of the things we were launching were failures by my standards. No one cared about them. No one was using them. They were hard to use.

And I wanted to make impactful things. And so I kept asking the questions, and I kept asking them earlier and earlier. This is how I ended up in user experience design. I was like, well, can we answer these questions first? Can we make a plan before we ever put pixels to screen, so to speak, [laughs] before we start building? Can we know something so that when we do build...which I had intimate understanding of how much work it is to build software. It's not nothing. It's a big investment of time and energy. And what I wanted increasingly was for that to be time and energy well spent for the entire team and for the universe. [laughs]

And so that's how I ended up...I think of it as like swimming upstream in the sense that there's still a lot of waterfall process going on in software. And I was just constantly asking why and for whom earlier and earlier in the process, just so that we could make sure that what we were building was "The Right It," to quote a book title that a lot of folks [laughs] in startup land have read.

Like, let's make sure it's "The Right It" before we invest a lot of time and energy, and, frankly, emotion into building something. That was really where this was coming from for me is that I think at heart, secretly or not so secretly, I'm still that engineer, that front-end engineer. And I want cool projects. I want to work on cool projects with cool people that are impactful. And I think that's true of most engineers. [laughs]

No one is purely satisfied to just be given an assignment that they're supposed to execute without thinking about it. And getting into UX and then getting into product management was for me almost like a mission to make sure that by the time something got to engineering, it was a good idea. I just wanted to save engineers from terrible projects; that was my whole mission. [laughs]

CHAD: Well, at thoughtbot, we have a set of core values, and one of them is fulfillment. And in the writing around that, the phrase we often use is we want to work on products that we believe deserve to exist.


CHAD: And that doesn't just mean that they have a positive impact on the world instead of a negative impact. But we're very intentional about the words we use, so there's a double meaning to that phrase. It's having a positive impact on the world, but it also means that it's the right product. This is what we should be building that it deserves to exist.

JORDYN: Yes, because you all know, we know how hard it is to make software. It's actually really hard. I think certainly building new products, you know, what a new product meant in 1920 is a very different thing than what [laughs] it means in 2022. And while it is a lot easier to bring new products into the world, like software products, internet products, it doesn't mean it's just easy. There's a lot of effort and resources that go into doing this, so let's make sure we're spending those things wisely.

Is the product idea good? Does it deserve to exist, but also, have we done our homework to validate that people want this, that they're going to use it? And to the extent that you can. There are limits to the ability of any team to forecast that. But when you bring more of this experimental mindset to it as soon as possible, it's like you up the odds that you'll end up building something valuable. And like you were saying about the word deserve, the word valuable to me is very broad, valuable to users, valuable to the business, valuable to the world. Let's create things of value if we're going to go to the trouble of creating things.

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CHAD: Have you found any tools, or techniques, or things that work particularly well for doing that?

JORDYN: Yeah, and it's probably not going to be all that satisfying. There are no shortcuts, I think, is what's challenging about this. [laughs] The tool and the process that I always start with and come back to is talking to customers and talking to users if those two people are not the same. Talk to people, not about your product idea; talk to them about their lives. Talk to them about what is difficult for them, what is easy for them, what they value, and you will seldom go wrong if you start and return to that process and truly listen.

This whole thing of talking to customers and talking to users is an art in and of itself. It's not idle, you know; it's not just a thing you toss off once in a while. [laughs] It's a skill. It's an art. And that is where you begin in it. Now, that is not the whole thing. But if you're starting there or returning there, you can always do this. I talk to teams all the time who have whiffed on this step of the process, and it's fine. Like, people who are builders, especially entrepreneurs, just want to get in there and start making something, like, I get that.

CHAD: Well, I think it's the combination of really wanting to move quickly and get to something really, really quickly. But I also think there is an element of fear...

JORDYN: [laughs] Yes.

CHAD: that causes people so that these two things combined really set people up to not do this...

JORDYN: To not do this, yes.

CHAD: because they're afraid of what they'll learn. And so it's much easier to just say, "Well, I know what to build. Let's build it. And you don't need to actually talk to people who might tell you something that isn't aligned with what you think the product should be."

JORDYN: 100%, 100%. Getting over that fear is hard, and you probably will just have to fail really hard without getting over it. I mean, that was certainly my experience, I mean, like several times. [laughs] I tried to build things without talking to anyone about it. I also was one of these people that built something that...and I can get into the story, but I built something that was successful enough without talking to a single person about it. And it really sent me down a fool's path for a while because I thought that's how it worked. But yeah, that fear is real.

But I think the thing that got me around it eventually and gets me around it now is there's the rational side of this which is, well, wouldn't you rather know sooner than later that something is not a good idea or this is not a pain point? Sure. But the more visceral, emotional thing that got me around it is good ideas are actually a dime a dozen. You'll have good ideas. You'll have ten good ideas tomorrow morning. Your one idea that you have decided to explore and build out and build a company around it won't be your only idea. It is not the only good idea. [laughs] You will have more of those. If you had 1, you'll have 10.

So talking to users means you'll figure'll have the opportunity to come up with more of those ideas, and one of them will be the winner. All of them are probably good ideas on some level. Having ideas isn't the problem. People are afraid of talking to customers and learning that their idea is not good, but you got to turn that on your head. You talk to customers to learn what they need, and then you'll have 20 ideas about how to solve that for them, solve that need.

The real fool's path here is to get attached to your first one idea that you had to solve a problem. It's to get attached to your problem before you have validated it. That's another pitfall here. But then to think that the first thought you had and how to solve it is going to be your only good idea, nah, you have lots of good ideas; we all do. [laughs] You'll have more.

So really just focusing on that pain point and listening to people and then really doing the work to generate more and more ideas. Even if you think you have a good solution now, it's always worth thinking about what other solutions might be constantly because your solution that you've come up with might have some feasibility issues. It might have other problems that you haven't seen yet. So it's always good to have more solutions in the hopper in case the one that you're pursuing right now doesn't turn out to be the right one.

CHAD: This is something that I don't know the answer to, and that is I do know you didn't originally start out as a developer, and it's not what your education is in.

JORDYN: [laughs] No.

CHAD: But how did you get into development?

JORDYN: [laughs] I was in college. This was just such a lucky, random thing. But I was in college, and I was in a band, a rock band. And this was early '98, maybe even fall '97. We were just at practice one day, and someone in the band was like, "We need a website." And this was when this was like a new thing that people did. [laughs] And everyone in the room just turned and looked at me. And I was like, "Oh, I'm making the website? Okay."

CHAD: Why? Were you a tech person in their mind?

JORDYN: I don't know, I guess because I seemed scrappy and capable even then. I have no idea. But I was like, all right, I'll see what I can figure out. So I wandered into the computer lab and just went to the person running the computer lab and was like, "Hey, how do I make a website?" [laughs] And this guy whose name I don't remember which is horrible, I really wish I could reach out to this guy and be like, "Hey, I have a career because of you, thank you."

CHAD: [laughs]

JORDYN: He was like, "Oh, cool. Here's what you do." And he basically opened up Netscape and was like, "Hey, there's like a..." there was like an editor. I don't even remember what it was called now. If you recall, there was an editor in Netscape. He was like, "Here's the basics of this. And here's a website," which was the... [laughs] What was the name of this website? All of the articles on this website were titled something like, so you want to make a webpage? Or so you want to make an interactive image replacement? Or so you want to host a website on a server? Whatever, like, that was all the articles.

And that website taught me how to code, and that guy put me on a path, and I just immediately was like, this is the most fun thing ever. I was like, I love this. [laughs] And it wasn't like two months before I had built the websites for a couple of departments on campus. My mom had a recruiting business at the time. She was like, "Can you make my recruiting business website?" It was just like, off to the races, which was great. But I graduated into the dot-com bust, which meant I could not get a job doing this. It's like entry-level folks always see a recession coming first, right?

CHAD: Right.

JORDYN: And everyone was like, "Oh my God, you can write HTML. You're going to get a six-figure job immediately," whatever. [laughs] And I was like, that is not what's happening here. I would have a job interview at someplace, and then they'd stop calling me. And I would find out that the company went under the day after I interviewed. That was what was happening.

So I couldn't get a job, a professional job doing this for a while. But I kept doing it on the side basically for my friends and family and eventually managed to get back into some professional [laughs] aboveboard real roles doing this work, but it was a struggle at first. And it was only just because I just really loved doing it, which, again, to circle back to something we talked about before, was kind of a liability for me for a while. Liking coding makes you really unthoughtful about what you're coding because you're always happy to do it, right? [laughs]

CHAD: Oh, I speak from personal experience, yes. [laughs]

JORDYN: Yes, right. I just wasn't thinking, is this a good idea? I was thinking great, cool; I get to code more. I love this. That was fine early on because I did get a lot of experience. And the first real job I got doing this work was at a company that was building websites for musicians, and our main client was Warner Brothers music. And so I got to build the My Chemical Romance website.

CHAD: Cool.

JORDYN: I got to build for the Confessions on the Dance Floor release and tour.

CHAD: That's really cool.

JORDYN: Like, it was really fun. And basically, I got to build a new website every two weeks for three years which was amazing bootcamp for me. The designers there were just fantastic. I learned more than I can ever even probably understand about doing that. But partly what I learned was [laughs] this feeling of this was where that feeling began where I was like, is this the right thing? Are we building the right thing? Or is this successful? That's when I started to ask those questions: is what we're doing what people want? So anyway, it was very fun. I got into it because I was in rock bands, which is strange. I don't think people typically find lucrative careers being in rock bands. [laughs]

CHAD: I talk to a lot of people over the years through our apprenticeship program, through different things where there are people out there who connect with programming like you did and like I did. The difference is that, for whatever reason, I had that experience when I was 10. [laughs] And other people just never get the opportunity to be exposed to that until later. But it's remarkable when it happens, and you get that connection where it just connects with you at a level that almost nothing has before. It's like a constant dopamine hit when you're programming.

JORDYN: Oh, it is. Yeah, I used to joke that, basically, I felt like I got to play video games for a living because that's what it felt like. It was just one puzzle game after another. It just didn't feel like work. I got to go to work every day and solve what felt like really interesting problems and puzzles. And at the end, there was a thing people used or could look at. It just felt like I'd hit pay dirt. I felt so lucky to have found it.

But yeah, I haven't done this since the pandemic. But for several years before that, I was a Girls Who Code instructor, and being able to pay that experience forward and help middle school, high school-aged girls who hadn't necessarily had this experience yet find themselves in coding, that was really the mission me and my co-teacher had decided that was really what we were after. We didn't care if they walked away from doing this with any hard coding skills. What we wanted them to have in their minds was I can be a programmer, and that seems like fun or possible for me. That was all we wanted.

And it was so amazing to see that moment where it clicked for them where they were like, "Oh, there's like a pattern here." And yeah, see that dopamine hit thing start to set up, you know, in their brains and know that it was only going to help them. I mean, I often said to them, "Major in whatever you want in college, but get a minor in computer science; that's where your job is. [laughter] Sorry to break this to you, but this is where your job is." [laughs]

CHAD: Another thing that you've done is you've advised a lot of companies through a few different organizations: Underscore VC, the Harvard Innovation Lab. What makes a good advisor as opposed to a bad advisor?

JORDYN: This is a really hard question, actually, because it's not often entirely clear in the moment whether a given advisor is...if you feel a lot of rapport with someone and they're helping you out in the moment, that's great. But often, one finds that something an advisor told you that did not land at all at the time comes back later to be something that's really useful. So I want to say up front that what makes a good advisor is really idiosyncratic to the founder, and to the advisor, and to the moment they find themselves together in.

So with that as a big caveat, I think what I bring to this, what I go out of my way to bring to it, is that I've been in the trenches. I know what that feels like. And I trust founders, like, my job there is to just add some perspective. I've participated in building over 30 products, so I can help them. They might be doing their first product or business, and all I'm there to do is bring a bunch of other experience for them to pick some insights from. It's not actually my job, I don't think, to pre-filter that stuff for them.

I'm very practical and hands-on. They bring a problem to me, and I'm like, "Okay, here's three times I've seen that situation before. And here are three things that happened." And I basically multiply their historical experience that they can draw from; that's sort of what I bring to this.

There's another thing here when I've had valuable advisors, this thing that's kind of hard to articulate. But it's like, often early on, what you need is just someone to take you seriously, just really take you seriously as a founder and a leader. I go way out of my way to make it clear that I am doing that with them and that it is my assumption 100% that they will rise to that occasion, that they will figure out who they need to be, what resources they need to bring to bear in order to be successful.

And doing that, taking them seriously and taking their ideas seriously, taking their experiences seriously, and really demonstrating that I think they have what it takes and I think that they can rise to this occasion, I think is probably the most valuable thing because most people don't do that. They come to your idea looking to tear it down, and I think it's well-meaning. They want to stress test you and your idea. That's all well and good. But, I mean, I'm often advising underrepresented founders and what they need is confidence. They need to be built up, not torn down.

That doesn't mean I don't bring skepticism and help them try to think evermore clearly about what it is they're doing and why; I definitely do that. But there's this baseline of I think you are capable of doing this. I think you are a person who gets to do this; that is not in question for me. And that alone I think is probably the most valuable thing you can get from an advisor, [laughs] is just someone to take you seriously.

CHAD: That's great. So for folks who have been familiar with thoughtbot for a while, we have a lot of advice out there in the world for how to build products, how to validate things, exercises to run, all that kind of stuff. And we bundle all of that up in what we call our playbook. And now, as we're sort of almost 20 years into this now, that's a big resource.

And so we're doing something new, which is extracting the information that we have specifically targeted towards those earliest stages of a new product or a business into a separate playbook. You're taking your wisdom, and you're going to be able to add it to that as well. And it's going to be a little bit more targeted. So we've just launched that. And you can find it at I would encourage folks to check that out.

Jordyn, when it comes to sharing, we're big at that at thoughtbot, and I'm excited to have you as part of that. Is there something that you think our approach from the fact that we're a consulting company or an agency makes it either in good ways or bad ways different than joining a product company and what you might do in a new role, or in sharing, or in working on things that we work on?

JORDYN: Yeah. I mean, I'm sure I'll have more to say about this when I've been here for a year. Having been here for a month, [laughter] this answer might be suspect. So far, anyway, the way I think about the differences here is that our role in working with product companies is to help them build the muscles to do this work, not to do it for them because they need to be able to do it going forward. We're not going to embed with them for the rest of time.

So that's a big difference, and that's both good and bad in the sense that we can maintain a certain amount of perspective because we can bring a kind of insider-outsider, like, we've done this lots and lots of times. We've seen the myriad ways that can go. And so we can bring that experience to bear while also remaining somewhat, I mean, objective is maybe a problematic word here, but some flavor of that while remaining outside of the everyday operational reality of the business. So that can be a really helpful perspective.

But I think the sort of risk there that I see is not being able to fully appreciate...that's the wrong word, but it's like, maybe not having the credibility we could have because we aren't going to be around to see this thing through. There's really, especially at early stages with projects, you really need people who are in it to win it, in it for the long haul. And so, I can see this looking like a tough sell for certain founders.

But from what I know so far, what I know about myself, what I know about thoughtbot so far is that that couldn't be further from the truth for us. We really are invested in folks' long-term success. And we do want to leverage our ability to focus and stand slightly outside of day-to-day operations to help them gain that perspective. But that is really the give and take, I think, of being a consultant rather than being part of the company.

CHAD: Now, it does make us...there are companies out there that that's not the goal, the goal is to make you dependent on them.

JORDYN: Yes, right. [laughs]

CHAD: That definitely is one of the unique things about thoughtbot is that that is not our goal. Our goal is to teach people to do what we do. But we do sometimes get criticized for, in those early stages, exactly that. It's like, where's your sense of urgency or your passion about this? And actually, we do have it. It's just the analogy I often use is we're like a professional sports team. [laughs] We make it look easy because we're really good at it.

And a lot of environments are ones where in order to make things happen, you need to create an environment of stress or those kinds of things. And that's what people are used to. And so when they start working with us, and they don't see that, they think something is wrong.

JORDYN: Yes, yes. 100%. And that is a huge cultural challenge with working with startups in general, where there is a real fire-fighting mentality. Like, let's get in there and make some stuff happen. Things are shifting constantly, and you've got to react. And I'm working 80-hour weeks to just make sure everything gets done. And I would hope..., and I've seen this to a certain extent in my month here so far, but the goal is for us to help folks work smarter, not harder, in the sense that more output does not mean more success.

We do have the experience of having worked on so many products, each of us individually and then collectively as a company. It is our goal, and it is my personal sincere hope that we can help these companies see how to do this work better and more sustainably without burning yourself out. If you happen to be successful while focused on this kind of work more output, it's only by chance you were successful there. It wasn't because you worked that hard. [laughs] And it's hard to see.

There is a lot of like hustle culture stuff out there that makes you feel like unless you are burning your candle at both ends, you're not doing it right. I think thoughtbot has the depth of experience to say," No, we can say otherwise," and to help companies figure out how to do that. I can absolutely see what you mean that people are like; these people don't have the fire in their belly, which couldn't be further from the truth. But it does feel very different from the inside.

CHAD: I feel like I could talk to you all day, [laughs] but we have to keep the episode somewhat within our normal constraints. Jordyn, thank you so much. If folks want to follow along with you or get in touch with you, where are the best places for them to do that?

JORDYN: So I am @skybondsor S-K-Y-B-O-N-D-S-O-R pretty much everywhere that you might want to... [laughter] A friend of mine gave me that nickname years ago. That's my handle pretty much everywhere. I spend a lot of time on Twitter, so that's probably the best place if you want to follow me or interact with me. But I'm also on LinkedIn and a lot of other places.

CHAD: And you can subscribe to the show, find notes along with a complete transcript for this episode at If you have questions or comments, email us at You can find me on Twitter at, not as an exciting username as @skybondsor, but @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore. Thanks so much for listening, and we'll see you next time.

ANNOUNCER: This podcast was brought to you by thoughtbot; thoughtbot is your expert design and development partner. Let's make your product and team a success.

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