Giant Robots Smashing Into Other Giant Robots

500: Giant Robots Smashing Into Other Giant Robots 500th Episode!

November 16th, 2023

We released episode one of this podcast on June 11, 2012. Now, more than a decade later, we're celebrating the 500th episode of our show. In honor of this milestone, Victoria, Will, and Chad caught up with each of the past hosts of the show: Ben Orenstein, Chris Toomey, and Lindsey Christensen.

We chatted about what they’re up to now, what they liked and learned from hosting the show, their time at thoughtbot, and more!

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VICTORIA: 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, Victoria Guido.

WILL: And I'm your other host, Will Larry.

CHAD: And I'm your other host, Chad Pytel.

We released episode one of this podcast on June 11, 2012. Now more than a decade later, were celebrating this: the 500th episode of our show. In honor of this milestone, Victoria, Will, and I caught up with each of the past hosts of the show: Ben Orenstein, Chris Toomey, and Lindsey Christensen.

We chatted about what they’re up to now, what they liked and learned from hosting the show and their time at thoughtbot, and more. First up: Ben Orenstein. Ben was the very first host of the show back in 2012 when he was a developer at thoughtbot. He is now the co-founder and Head of Product at Tuple, a remote pair programming tool for designers and developers. Ben, it's great to talk to you again. It's been a while since you and I talked. How have you been?

BEN: I've been decent, yeah. It's fun to be back to my roots a little bit. I told some folks that I work with that I was coming back to the pod for the 500th Episode, and they were stoked. So, it's kind of a treat to get to be on these airwaves again.

CHAD: What have you been up to since you left this show and thoughtbot?

BEN: Well, I started a company. So, I was at thoughtbot for a while; I think it was seven years. And I eventually sort of struck out to start my own thing–had a false start or two here and there. And then, I ended up starting a company called Tuple, and we still exist today, fortunately.

Tuple is a tool for doing remote pair programming. We started off on macOS and then wrote a Linux client. And we're launching a Windows client now. But it's sort of, like, screen sharing with remote control for developers who are actually writing code and want to have great, low latency remote control and who care about screen share quality and that sort of thing.

I started that about five years ago with two co-founders. Today, we are a team of 11, I think it is. And it's been going well. Our timing was really great, it turned out. We launched a little bit before COVID. So, remote work turned into a lot more of a thing, and we were already in the market. So, that helped us a ton. It was quite a wild ride there for a bit.

But things have calmed down a little lately, but it's still fun. I'm, like, really enjoying being a co-founder of a software company. It was what I've always sort of wanted to do. And it turns out it actually is pretty fun and pretty great. Although there are, of course, the ups and downs of business ownership. It is never quite as calm or relaxing as being an employee somewhere else.

CHAD: You started Tuple instigated by...full disclosure: thoughtbot's an early customer of Tuple. We're still a customer. We use it a lot.

BEN: Woo-hoo. I appreciate that. Thank you.

CHAD: If I remember right, you started and were sort of instigated to create Tuple because there was a prior product that then Slack bought, and then it started to degrade. And now, it no longer exists in the same way that it did before.

BEN: Yeah. So, there was this tool called Screenhero, which I actually started using --

CHAD: [inaudible 02:14]

BEN: Yeah, first at thoughtbot. Some other thoughtboter introduced me to it, and we would use it for pair programming. And I was like, oh, this is nice. And then yeah, Slack kind of acqui-hired it and more or less ended up shutting the product down. And so, there was this gap in the market. And I would ask my friends, I would ask thoughtboters and other developers, like, "What are you using now that Screenhero is gone?" And no one had a good answer.

And so, after a while of this thing sort of staring me in the face, I was like, we have to try to solve this need. There's clearly a hole in the market. Yeah, so we were heavily inspired by them in the early days. Hopefully, we've charted our own path now. But they were definitely...the initial seed was, you know, let's do Screenhero but try to not get bought early or something.

CHAD: [laughs] How did you or did you feel like you captured a lot of the Screenhero customers and reached them in those early days?

BEN: I think so. The pitch for it was sort of shockingly easy because Screenhero had kind of blazed this trail. Like, I would often just be like, "Oh, we're making a thing. Do you remember Screenhero?" And they'd go, "Oh yeah, I loved Screenhero". I'd be like, "Yeah, we're going to try to do that." And they'd be like, "Nice. Sign me up." So, it for sure helped a ton. I have no idea what percentage of customers we converted. And they were a pretty large success, so probably a small fraction, but it definitely, like, made the initial days much easier.

CHAD: Yeah. And then, like you said, COVID happened.

BEN: COVID happened, yeah. I think we had been around for about a year when COVID hit. So, we were getting our feet underneath us. And we were already, like, the company was already growing at a pretty good rate, and we were feeling pretty good about it. I don't think we had quite hit ramen profitable, but we were probably pretty close or, like, flirting with it.

Yeah, the business, like, I don't know, tripled or quadrupled in a matter of months. We had a few big customers that, like, just told everyone to start using Tuple. So, we had, like, thousands and thousands of new users kind of immediately. So, it was a crazy time. Everything melted, of course. We hadn't quite engineered for that much scale. We had a really rough day or so as we scrambled, but fortunately, we got things under control. And then had this, like, very nice tailwind.

Because we started the company assuming that remote work would grow. We assumed that there would be more remote developers every year. And, you know, it's probably maybe 5% of dev jobs are remote or maybe even less, but we expect to see this number creeping up. We don't think that trend will reverse. And so, COVID just, like, it just yanked it, you know, a decade in the future.

CHAD: You haven't tripled or quadrupled your team size, have you?

BEN: No. Well, I mean, I guess, I mean, we started as 3, and now we're 11, so kind of.

CHAD: [laughs] Yeah, that's true.

BEN: Expenses have not grown as fast as revenue, fortunately.

CHAD: That's good. That's basically what I was asking [laughs].

BEN: Yeah, yeah. We're still a pretty small team, actually. We have only, like, four or five full-time engineers on the team at the moment, which is kind of wild because we are now, you know, we have three platforms to support: Linux, Windows, and Mac. It's a pretty complicated app doing, like, real-time streaming of audio, webcams, desktops, caring about OS-level intricacies.

So, I think we will be hiring more people soon, although we haven't said that for a long time. We sort of have always had a bit of a hire-slow mentality to try to get the right team members and, like, feel a real pain before we hire someone into it. But we have been getting a bit more aggressive with hiring lately.

VICTORIA: Well, I really appreciate Tuple. I installed it when I first started working here at thoughtbot. And we have random pairings with everyone across the company. So, I'll randomly get to meet someone halfway across the world who's working on similar projects. And I think they really enjoy that I have a tool they like working to share what they're working on. So, I want to thank you for that.

And I'm curious about when you really started to scale during COVID, what were some of the technology architecture trade-offs you came across, and where did you land with it?

BEN: Well, we got fairly...I don't know if it was lucky, but we...for a long time, for years, even through COVID, maybe the first four years of the company, all Tuple calls were purely peer-to-peer. And there was no server that we owned intermediating things. This was, like, kind of one of the keys of, like, not having expenses. The scale of revenue was we could have lots more calls happen. And it wouldn't cost us bandwidth or server capacity.

To this day, still, for any calls with three or fewer participants, they're purely peer-to-peer. And this is nice for latency purposes because it just...we can find the most direct path to the internet between two people. It's also nice from our cost perspective because we don't need to pay to send that data. And that was hugely useful as call volume went up immensely. Didn't have to worry too much about server load and didn't have to worry too much about bandwidth costs.

CHAD: Today, is there a central service that makes the initial connection for people?

BEN: Yes, yeah, yeah. So, there is a signaling server. So, when you launch the app, you sign in, and you see, like, oh, which of my co-workers are online? So, there is actually a Rails app that handles that, actually, increasingly less the Rails app. We have now...I think it's a Go service that actually manages all those. I'm further and further from the code every year. Some of the technical questions might be a little bit beyond me, or I might have slightly out-of-date info.

But back to the architecture question for a second, we did a pretty big refactor when we decided to go from just being a Mac client to supporting other platforms, where we split out a cross-platform real-time communication engine written in C++ so that we could use that for all of the heavy lifting, all the managing of the connections, and the tricky bandwidth estimation, and all this stuff, and use that across different platforms. And so, today, you have the cross-platform engine, and then on top of that is a, like, a less specific layer for each of the operating systems that we support.

CHAD: So, you mentioned you're less and less in the code these days. So, what do you spend your time doing then?

BEN: It's a mix of things. These days, it's basically mostly --

CHAD: Just cocktails on the beach, right?

BEN: Cocktails, yes [laughs], cocktails on the beach, appearing on podcasts trying to sound important and impressive, yeah. Mostly product work. So, right before this, I just got off a call with some folks from The Browser Company. They are some of our first alpha users for our new Windows clients. So, I hopped on the call with them and, like, watched three of them install the product and inevitably run into some bugs. And, you know, chatted through those with the engineer that was working on it, prioritized some stuff, made some decisions about what's coming up next, and what we're going to ignore. So, mostly product work these days.

For the first five years of the company, I was CEO, so I was doing kind of everything: marketing, and also hiring, and also product. About two months ago, I stepped down as CEO, and one of my other co-founders, Spencer, stepped up. And so, now my focus has narrowed to be mostly just product stuff and much less on the marketing or hiring side.

VICTORIA: Yeah, you mentioned that it was a little more comfortable to be an employee than to be a founder. I don't know if you could say more about that because, certainly, a lot of engineers are smart enough and capable enough to run their own company. But what really informed your choice there, and do you regret it? [laughs]

BEN: I definitely don't regret it. thoughtbot was a close second in terms of wonderful professional experiences. But running my own thing has been the most interesting professional thing I've done by a big margin. It has also been more stressful. And, Chad, I don't know if you remember, I think, like, maybe eight years ago, you tweeted something like, if you want to sleep well at night, and, like, value that, like, peace of mind, like, don't start a company or something. I have experienced that.

CHAD: [laughs]

BEN: A lot more, yeah, like waking up in the middle of the night worrying about things. It feels a little bit like the highs are higher; the lows are lower. Being an employee somewhere, it's like, if this company fails, I know I can go get another job, right? Like, you're a developer. You're extremely employable. But as the owner of the company, if the company fails, like, a huge chunk of your net worth is gone. Like, this thing you poured your life into is gone. It's way more stressful and traumatic to have that happen, or have that threatened to be happening, or just imagine that happening.

So, overall, I have found the trade-off to be totally worth it. It's awesome to make your own decisions and chart your own path. And when it works, it can work in a way that being a salaried employee can't. So, I'm happy with those trade-offs. But I think that is a good question for people to ask themselves as they consider doing something like this is, like: is that the kind of trade-off that you want to make? Because it has significant downsides for sure.

WILL: I am a big fan of Tuple also. I love it. It [inaudible 10:08] easy, especially with remote work. You hit the jackpot with COVID and remote work, so kudos for that [laughs]. Was there anything...because I know from our previous companies, about over...hopefully a lot more of the good stuff than the bad stuff. But was there anything that you learned? Because you were at thoughtbot for seven years. Was there anything that you're like, oh my gosh, I learned that, and it's helped me till this day while I'm running my company?

BEN: Yeah, quite a bit, actually. I think it'd be hard to tease apart exactly which lessons, but I I ran Upcase for thoughtbot and also FormKeep. So, I got a chance to kind of run a small division of the company, while still being a normal employee and, like, having not much of that risk. And I think that was a really wonderful opportunity for me to, like, practice the skills that I was interested in. Just, like, how do you market a thing? How do you design a product and have it be good? How do you prioritize user feedback?

There were a ton of lessons from those days that I feel like made me better at running our company when we actually took a shot at it. So, there were, like, the specific things that I learned by the work I was doing there. But then just, like, I mean, I think I am the programmer I am today because of, like, the weekly dev discussions that happened.

Like, spending so much time with Joe Ferris and, like, trying to copy as much of his brain as possible, like, really, like, imprinted on me as, like, a programmer. And also, just, like, a lot of the sort of cultural things from my time at thoughtbot of, like, you should be sharing the things you're learning. Like, writing blog posts is a great use of time. Like, doing open-source work is a great use of time.

And maybe you can't directly trace how doing, like, working in public or sharing information benefits the company. It's hard to, like, attribute it from a marketing sense. But if you sort of have faith that in the large, it's going to work out, it probably will. That feels like a thoughtbot lesson to me, and I think it has served us really well; where I recorded a weekly podcast for a long time called The Art of Product. I'm recording a new podcast called Hackers Incorporated with Adam Wathan of Tailwind fame.

And I don't ever think, like, hmm, how many new leads do we think we get per episode, and how many hours has that taken? What's the ROI? I just have this sort of reflex that I developed from thoughtbot time of, like, you should be putting stuff out there, or you should be giving back. You should help other people. And that will probably help your business and make it work in the long term.

CHAD: That's a good lesson [laughs]. One of the other things, you know, while you were a host of Giant Robots, you were the first host. I remember, you know, encouraging you to be the first host, and I think we talked about that in one of the episodes along the way. But we also transitioned the format a little bit, especially as you started to work on products here; you know, it was more about the building of those products and following along with those.

And one of the things that sort of half-jokingly defined, I think, your impact on a lot of products was pricing, experimenting with pricing, learning about pricing, increasing prices more than people were maybe comfortable doing so. How has that worked out with Tuple, pricing in particular?

BEN: It's really hard to say. It's hard to know what, like, the other path would have been through the world-. We sort of decided from, like, the early days that we wanted to have, like, a fairly premium price. Like, we wanted to be the product that was really good and was, like, a little bit annoyingly expensive, but you still paid for it because it felt worth it. And I think people could debate in both directions whether we nailed that or not.

We have had a price increase that we ended up rolling back. We went, like, a little too far one time and said, "You know what? I think we're a little bit over," and we reverted that. But I would say even today, we are still a fairly pricey product. I mean, I'm pretty happy with how the company has done. I can't prove to you that, like, if the price were half what it is, we would have, you know, better success or not.

CHAD: I think it'd be very hard to make the argument that if it was half that, you would have double the number of customers.

BEN: Yeah, that's probably not true.

CHAD: Not with the customers that you have, who are companies that will pay for products that they use as much as Tuple.

BEN: Yeah, I'm happy serving the kind of companies, and they end up being mostly tech companies that really value developer happiness. When their developers come to them and they say, "We don't want to pair over Zoom. We like this thing. It's better. It feels nicer to use," they say, "Okay," and they buy the tool for them. There are places where that's not the case. And they say, "We already have a thing that does screen sharing. You're not allowed to buy this." We don't invest a lot of time trying to sell to those people or convince them that they're wrong. And I'm pretty happy serving sort of the first group.

CHAD: So, you've mentioned that you've still been podcasting. To be honest, I didn't realize you were starting something new. Is it live now?

BEN: It is live now, yeah.

CHAD: Awesome. Where can people find that?

BEN: It's about the transition from developer to founder, which is kind of what we've been touching on here. Yeah, hopefully, the audience is developers who want to start something or have started something who are maybe a little bit further behind progression-wise.

And it's kind of, like, I have some lessons, and Adam has some lessons, and, you know, we don't think that we're experts. But sometimes it's useful to just hear, like, two people's story and sort of see, like, what seemingly has worked for them. So, we've been trying to share things there. And I think people will find it useful.

VICTORIA: I was going to ask you for a lesson, maybe give us a little sample about how would you advise someone who's built a product and wants to market it, and it's targeted towards developers since you mentioned that previously as well.

BEN: Yeah, in a way, the question already contains a problem. It's like, oh, I built the product; now how do I market it? It's a little bit indicative of a very common failure mode for developers, which is that. They sort of assume, okay, after you make the product, you then figure out how you're going to market it. And marketing is sort of a thing you layer on later on when you realize that just, like, throwing it on Twitter or Product Hunt didn't really work.

When we started building Tuple, I was out there marketing it already. So, I had two co-founders, so this is a luxury I had. My two co-founders were writing code, and I was out doing stuff. I was recording podcasts. I was tweeting about things. I was making videos. I was giving conference talks. And I was getting people to hear about our product well before it was done. In fact, I was even selling it. I was taking pre-orders for annual subscriptions to the app while it was still vaporware.

So, I would say, like, you basically can't start marketing too early. If you start marketing early and no one really cares, well, then you don't really have to build it probably. I would actually even go a little further and say, like, I started marketing Tuple before we had a product available. But in reality, I started marketing Tuple seven or so years before that when I started publishing things through thoughtbot.

It's like when I was traveling around giving talks about Ruby, and when I was making screencasts about Vim, and when I was running Upcase, I was, over time, building an audience. And that audience was useful for thoughtbot, and it also was useful for me so that when I left, I had something like 10,000 Twitter followers or something, a few thousand people on our mailing list.

But there were a lot of developers that already sort of knew me and trusted me to make fairly good things. And so, when I said, "Hey, I've made a new thing, and it's for you," I really benefited from those years of making useful content and trying to be useful on the internet. And in the early days, we had people sign up, and they would say, "I don't even really think I'm going to use this. But I've learned so much from you over the years that I want to support you, so I'm going to pay for a subscription."

VICTORIA: I like your answer because I think the same thing when people ask me, like, because I am an organizer for Women Who Code, and I know all these great people from showing up for years in person months over months. And so, then people will ask, "Oh, how do I recruit more women in my company?" I'm like, "Well, you got to start showing up [laughs] now and do that for a couple of years, and then maybe people will trust you," right? So, I really like that answer.

WILL: How has your relationship with Chad continued to grow since you left? Because seven years at the company is a lot. And it seems like you're still on really, really good terms, and you're still friends. And I know that doesn't happen at every company.

BEN: I mean, it was tough deciding to leave. I think, like, both of us felt pretty sad about it. That was the longest I'd ever worked anywhere, and I really enjoyed the experience. So, I think it was tough on both sides, honestly. But we haven't kept in that much touch since then. I think we've emailed a handful of times here and there. We're both sociable people, and we sort of get each other. And there's a long history there. So, I think it's just easy for us to kind of drop back into a friendly vibe is sort of how I feel about it.

CHAD: Yeah. And the way I explain it to people, you know, when you're leading a company, which Ben and I both are, you put a lot of energy into that and to the people who are on that team. If you're doing things right, there's not really hard feelings when someone leaves. But you need to put in a lot of effort to keep in touch with people outside of the company and a lot of energy. And, to be honest, I don't necessarily do as good a job with that as I would like because it's a little bit higher priority to maintain relationships with them, the people who are still at thoughtbot and who are joining.

BEN: What you're saying is I'm dead to you [laughter]. That's CEO, for you're dead to me.

CHAD: No. It's hard feelings.

BEN: Totally.

CHAD: I think one of the things that has been great about the show over the years is that we haven't been afraid to change the format, which I think has been important to keeping it going. So, there is sort of; in fact, the website now is organized into seasons. And I went back and re-categorized all the episodes into seasons. And when the seasons were made up of, like, sort of the format of the show or particular hosts...when we started, it was just an interview show, and it was largely technical topics.

And then we started The Bike Shed, and the technical topics sort of moved over there. But it also went with your interests more under the product and business side. Then you started working on products at thoughtbot, so it started to go even more in that. And I think Chris joined you on the show, and that was sort of all about those topics.

BEN: Yeah, that makes sense. I think if you don't let the hosts kind of follow their interests, they're going to probably burn out on the thing. It's not fun to force yourself, I think, to record a podcast.

CHAD: Yeah. And then when you left, you know, I took over hosting and hosted by myself for a while, went back to the interview format, but then was joined by Lindsey for a little while. We experimented with a few different things: one, interviews, but then we did a whole, just under a year, where we followed along with three companies. And each month, we would have an interview episode where we talked to them, all three companies, about the same topic.

And then, we also did an episode with just Lindsey and I talking about that topic and about what we learned from the startup companies that we were following along with for the year. And now we're back to interview freeform, different guests, different topics. It seems like we're going to stick with that for a little while. But, obviously, as Will and Victoria have said, like, we'll probably change it again in some way, you know, a year, two years, three years from now.

VICTORIA: Yeah, and I'm definitely bringing my interest around DevOps and platform engineering, so you'll see more guests who have that focus in their background. And with that, sometimes my interview style is more; how do I ask a question that I can't read from your developer docs and that I might not understand the answer to? [laughs] That's kind of where I like to go with it. So yeah, I'm really excited's probably one of my favorite parts of my job here at thoughtbot because I get to meet so many interesting people. And, hopefully, that's interesting to everyone else [laughs] and our guests, yeah.

BEN: Totally. Well, I dramatically underestimated how awesome it would be to meet all kinds of cool people in the industry when I started the podcast. I didn't truly connect in my head, like, wait a second, if I have a 45-minute conversation with, like, a lot of prominent, awesome people in our field, that's going to be really interesting and useful for me. So, I think, yeah, it's nice to be in the hosting seat.

VICTORIA: And it's so surprising how I'll meet someone at a conference, and I'll invite them onto the podcast. And the way it winds up is that whatever we're talking about on the show is directly relevant to what I'm working on or a problem that I have.

It's been incredible. And I really appreciate you for coming back for our 500th Episode here.

CHAD: Ben, thanks very much again for joining us, and congratulations on all the success with Tuple. And I wish you the best.

BEN: Thank you so much. Thanks for being a continuing customer. I really appreciate it.

CHAD: Next, we caught up with Chris Toomey, who had a run as co-host of the show with Ben throughout 2016.

CHRIS: Hi there. Thanks for having me.

So, we're talking with all of the past hosts. I know you joined the show, and you were on it with Ben. And then you moved over to The Bike Shed, right?

CHRIS: Yeah. So, I had co-hosted with Ben for about six months. And then I think I was transitioning off of Upcase, and so that ended sort of the Giant Robots “let's talk about business” podcast tour for me. And then, I went back to consulting for a while. And, at some point, after Derek Prior had left, I took over as the host of The Bike Shed. So, I think there was probably, like, a year and a half, two-year gap in between the various hostings.

CHAD: Are you doing any podcasting now?

CHRIS: I'm not, and I miss it. It was a lot of fun. It was, I think, an ideal medium for me. I'm not as good at writing. I tend to over-edit and overthink. But when you get me on a podcast, I just start to say what's in my head, and I tend to not hate it after the fact. So [chuckles], that combination I found to be somewhat perfect for me. But yeah, lacking that in my current day-to-day.

CHAD: Well, what's been taking up your time since you left?

CHRIS: I had decided it was time to sort of go exploring, try and maybe join a startup, that sort of thing. I was sort of called in that direction. So, just after I left thoughtbot, I did a little bit of freelancing, but that was mostly to sort of keep the lights on and start to connect with folks and see if there might be an opportunity out there.

I was able to connect with a former thoughtbot client, Sam Zimmerman, who was looking to start something as well. And so, we put our act together and formed a company called Sagewell, which was trying to build a digital financial platform for seniors, which is a whole bunch of different complicated things to try and string together. So, that was a wonderful experience. I was CTO of that organization. And I think that ran for about two and a half years. Unfortunately, Sagewell couldn't quite find the right sort of sticking point and, unfortunately, shut down a little bit earlier in this year.

But that was, I would say, the lion's share of what I have done since leaving thoughtbot, really wonderful experience, got to learn a ton about all of the different aspects of building a startup. And I think somewhat pointedly learned that, like, it's messy, but I think I do like this startup world.

So, since leaving Sagewell, I've now joined a company called August Health, which has a couple of ex-thoughtboters there as well. And August is post their Series A. They're a little bit further along in their journey. So, it was sort of a nice continuation of the startup experience, getting to see a company a little bit further on but still with lots of the good type of problems, lots of code to write, lots of product to build. So, excited to be joining them. And yeah, that's mostly what's taking up my time these days.

CHAD: So, I know at Sagewell, you made a lot of technical architecture, team decisions. It was Rails in the backend, Svelte in the frontend, if I'm not mistaken.

CHRIS: Yep, that's correct.

CHAD: You know, hindsight is always 2020. Is there anything you learned along the way, or given how things ended up, that you would do differently?

CHRIS: Sure. I was really happy with the tech stack that we were able to put together. Svelte was probably the most out there of the choices, I would say, but even that, it was sort of relegated to the frontend. And so, it was a little bit novel for folks coming into the codebase. Most folks had worked in React before but didn't know Svelte. They were able to pick it up pretty quickly.

But Inertia.js was actually the core sort of architecture of the app, sort of connected the frontend and the backend, and really allowed us to move incredibly quickly. And I was very, very happy with that decision. We even ended up building our mobile applications, both for iOS and Android. So, we had native apps in both of the stores, but the apps were basically wrappers around the Rails application with a technology similar to Turbolinks native–if folks are familiar with that so, sort of a WebView layer but with some native interactions where you want.

And so, like, we introduced a native login screen on both platforms so that we could do biometric login and that sort of thing. But at the end of the day, most of the screens in the app didn't need to be differentiated between a truly native mobile app and what like, mobile WebView would look like. So, we leaned into that.

And it was incredible just how much we were able to do with that stack and how quickly we were able to move, and also how confidently we were able to move, which was really a nice thing. Having the deep integration between the backend and the frontend really allowed a very small team to get a lot done in a short time.

CHAD: Does that code live on in any capacity?


CHAD: Oh. How does that make you feel?


CHRIS: It makes me feel very sad, I will say. That said, I mean, at the end of the day, code is in service of a business. And so, like, the code...there are, I think, probably a couple of things that we might be able to extract and share. There were some interesting...we did some weird stuff with the serializers and some, like, TypeScript type generation on the frontend that was somewhat novel.

But at the end of the day, you know, code is in service of a business, and, unfortunately, the business is not continuing on. So, the code in the abstract's more, you know, the journey that we had along the way and the friends we made and whatnot. But I think, for me, sort of the learnings of I really appreciate this architecture and will absolutely bring it to any new projects that I'm building from, you know, greenfield moving forward.

VICTORIA: I'm curious what it was like to go from being a consultant to being a big player in a startup and being responsible for the business and the technology. How did that feel for you?

CHRIS: I would say somewhat natural. I think the consulting experience really lent well to trying to think about not just the technical ramifications but, you know, what's the business impact? How do we structure a backlog and communicate about what features we want to build in what order? How do we, you know, scope a minimal MVP? All those sorts of things were, I think, really useful in allowing me to sort of help shape the direction of the company and be as productive of an engineering team as we could be.

CHAD: A lot of the projects you worked on at thoughtbot were if not for startups, helping to launch new products. And then, a lot of the work you did at thoughtbot, too, was on Upcase, which was very much building a business.

CHRIS: Yes. I definitely find myself drawn in that direction, and part of like, as I mentioned, I seem to be inclined towards this startup world. And I think it's that, like, the intersection between tech and business is sort of my sweet spot. I work with a lot of developers who are really interested in getting sort of deeper into the technical layers, or Docker and Kubernetes and orchestration. And I always find myself a little bit resistant to those. I'm like, I mean, whatever. Let's just...let's get something out there so that we can get users on it. And I am so drawn to that side, you know, you need both types of developers critically.

I definitely find myself drawn to that business side a little bit more than many of the folks that I work with, and helping to bridge that gap and communicate about requirements and all those sort of things. So, definitely, the experience as a consultant really informed that and helped me have sort of a vocabulary and a comfort in those sort of conversations.

WILL: How did Upcase come about? Because I know I've talked to numerous people who have gone through Upcase. I actually went through it, and I learned a ton. So, how did that come about?

CHRIS: I think that was a dream in Ben Orenstein's eye. It started as thoughtbot Learn many, many years ago. There was a handful of workshops that had been recorded. And so, there were the video recordings of those workshops that thoughtbot used to provide in person. Ben collected those together and made them sort of an offering on the internet.

I think Chad, you, and I were on some podcast episode where you sort of talked about the pricing models over time and how that went from, like, a high dollar one-time download to, like, $99 a month to $29 a month, and now Upcase is free. And so, it sort of went on this long journey. But it was an interesting exploration of building a content business of sort of really leaning into the thoughtbot ideal of sharing as much information as possible, and took a couple of different shapes over time.

There was the weekly iterations of the video series that would come out each week, as well as the, like, longer format trails, and eventually some exercises and whatnot, but very much an organic sort of evolving thing that started as just a handful of videos and then became much more of a complete platform. I think I hit the high points there. But, Chad, does that all sound accurate to you?

CHAD: Yeah, I led the transition from our workshops to Learn, which brought everything together. And then, I stepped away as product manager, and Ben took it the next step to Upcase and really productized it into a SaaS sort of monthly recurring billing model and took it over from there. But it still exists, and a lot of the stuff there is still really good [laughs].

CHRIS: Yeah, I remain deeply proud of lots of the videos on that platform. And I'm very glad that they are still out there, and I can point folks at them.

VICTORIA: I love that idea that you said about trying to get as much content out there as possible or, like, really overcommunicate. I'm curious if that's also stayed with you as you've moved on to startups, about just trying to get that influence over, like, what you're doing and how you're promoting your work continues.

CHRIS: I will say one of the experiences that really sticks with me is I had followed thoughtbot for a while before I actually joined. So, I was reading the blog, and I was listening to the podcasts and was really informing a lot of how I thought about building software. And I was so excited when I joined thoughtbot to, like, finally see behind the curtain and see, like, okay, so, what are the insider secrets?

And I was equal parts let down...actually, not equal parts. I was a little bit let down but then also sort of invigorated to see, like, no, no, it's all out there. It's like, the blog and the open-source repos and those sort of...that really is the documentation of how thoughtbot thinks about and builds software. So, that was really foundational for me. But at the same time, I also saw sort of the complexity of it and how much effort goes into it, you know, investment time Fridays, and those sort of things.

Like, a thoughtbot blog post is not a trivial thing to put up into the world. So many different people were collaborating and working on it. And so, I've simultaneously loved the sharing, and where sharing makes sense, I've tried to do that. But I also recognize the deep cost. And I think for thoughtbot, it's always made sense because it's been such a great mechanism for getting the thoughtbot name out there and for getting clients and for hiring developers.

At startups, it becomes a really interesting trade-off of, should we be allocating time to building up sort of a brand in the name and getting ourselves, you know, getting information out there? Versus, should we be just focusing on the work at hand? And most organizations that I've worked with have bias towards certainly less sharing than thoughtbot, but just not much at all. Often, I'll see folks like, "Hey, maybe we should start a blog." And I'm like, "Okay, let's just talk about how much effort that [laughs] actually looks like." And I wonder if I'm actually overcorrected on that, having seen, you know, the high bar that thoughtbot set.

CHAD: I think it's a struggle. This is one of my [laughs] hot topics or spiels that I can go on. You know, in most other companies, that kind of thing only only helps in hiring or the people being fulfilled in the work. But at most companies, your product is not about that; that's not what your business is. So, having a more fulfilled engineering team who is easier to hire—don't get me wrong, there are advantages to that—but it doesn't also help with your sales.


CHAD: And at thoughtbot, our business is totally aligned with the people and what we do as designers and developers. And so, when we improve one, we improve the other, and that's why we can make it work. That is marketing for the product that we actually sell, and that's not the case at a SaaS software company.

CHRIS: Yes, yeah, definitely. That resonates strongly. I will say, though, on the hiring side, hiring at thoughtbot was always...there was...I won't say a cheat code, but just if someone were to come into the hiring process and they're like, "Oh yeah, I've read the blog. I listen to the podcast," this and that, immediately, you were able to skip so much further into the conversation and be like, "Okay, what do you agree with? What do you disagree with? Like, let's talk." But there's so much.

Because thoughtbot put so much out there, it was easy to say, like, "Hey, this is who we are. Do you like that? Is that your vibe?" Whereas most engineering organizations don't have that. And so, you have to try and, like, build that in the context of, you know, a couple of hour conversations in an interview, and it's just so much harder to do. So, again, I've leaned in the direction of not going anywhere near thoughtbot's level of sharing. But the downside when you are hiring, you're like, oh, this is going to be trickier.

CHAD: Yeah. One of the moments that stands out in my mind, and maybe I've told this story before on the podcast, but I'll tell it again. When we opened the New York studio, it was really fast growing and was doing a lot of hiring. And one of the people who had just joined the company a couple of weeks before was doing an interview and rejected the person was able to write an articulate reason why. But it all boiled down to this person is, you know, not a fit for thoughtbot.

Based on what they were able to describe, I felt very confident with the ability or with the fact that they were able to make that call, even though they had been here only a couple of weeks, because they joined knowing who we were, and what we stand for, and what our culture and our values are, and the way that we do things, and all that kind of thing. And so, yeah, that's definitely a huge benefit to us.

VICTORIA: I've certainly enjoyed that as well, as someone who hires developers here and also in meeting new companies and organizations when they already know thoughtbot. That's really nice to have that reputation there, coming from my background—some really more scrappier startup kind of consulting agencies.

But, you know, I wanted to talk a little bit more about your podcasting experience while you're here. So, I know you were on both The Bike Shed and Giant Robots. Which is the better podcast? [laughter] So, what's you have, like, a favorite episode or favorite moment, or maybe, like, a little anecdote you can share from hosting?

CHRIS: Well, I guess there's, like, three different eras for me in the podcasting. So, there's Giant Robots with Ben talking more about business stuff, and I think that was really useful. I think it was more of a forcing function on me because I sort of...Both Ben and I were coming on; we were giving honest, transparent summaries of our, like, MRR and stats and how things were growing, and acted as sort of an accountability backstop, which was super useful but also just kind of nerve-wracking.

Then, when I joined the Bike Shed, the interviewing sequence that I did each week was just a new person that I was chatting with. And I sort of had to ramp them up on, hey, here's a quick summary on how to think about podcasting. Don't worry, it'll be great. Everybody have fun. But I was finding each of the guests. I was sort of finding a topic to talk about with them. So, that ended up being a lot more work.

And then, the last three years chatting with Steph that was by far my favorite. There was just such a natural back-and-forth. It really was just capturing the conversations of two developers at thoughtbot and the questions we would ask each other as we hit something complicated in a piece of code or, "Oh, I saw this, you know, article about a new open-source repository. What do you think about that?" It was so much easier, so much more natural, and, frankly, a lot of fun to do that.

And, two, I actually do have an answer to the favorite podcast episode, which is the first episode that Steph was ever on. It was before she actually joined as a co-host. But it was called “What I Believe About Software.” And it was just this really great, deep conversation about how we think about software. And a lot of it is very much, like, thoughtbot ideals, I would say. But yeah, Steph came in and just brought the heat in that first episode, and I remember just how enjoyable that experience was. And I was like, all right, let's see if I can get her to hang out a little bit more, and, thankfully, she was happy to join.

WILL: What was your favorite position, I guess you can call it? Because you say you like the mixture of business and, you know, development. So, you've been in leadership as development director, CTO. You've been a web developer. You've been over content, like, with Upcase. What was your favorite position [inaudible 16:43] you were doing, and why was it your favorite?

CHRIS: The development director role feels like sort of a cheating answer, but I think that would be my answer because it contained a handful of things within it. Like, as development director, I was still working on client projects three days a week. And then, one day a week was sort of allocated to the manager-type tasks, or having one-on-ones with my team sort of helping to think about strategy and whatnot. And then, ideally, still getting some amount of investment time, although the relative amounts of those always flexed a little bit. Because that one sort of encompassed different facets, I think that's going to be my answer.

And I think, like, some of what drew me to consulting in the first place and kept me in that line of work for seven years was the variety, you know, different clients, as well as, even within thoughtbot, different modes of working in podcasts or video. Or there was a bootcamp that I taught, a session of Metis, which that was a whole other experience. And so, getting that variety was really interesting.

And I think as sort of a tricky answer to your question, the development director role as a singular thing contained a multitude, and so I think that was the one that would stand out to me. It's also the most, you know, the one that I ended on, so [laughs] it might just be recency bias, but yeah.

VICTORIA: Oh, I love that. Is there anything else that you would like to promote on the podcast today?

CHRIS: No, although as you ask the question, I feel like I should, I don't know, make some things to promote, get back into some, I don't know, content generation or something like that. But for now, no. I'm, you know, diving into the startup life, and it's a wonderful and engrossing way to do work, but it does definitely take up a lot of my headspace. So, it's an interesting trade-off.

But right now, I don't know; if folks are online and they want to say hi, most of my contact information is readily available. So, I would love to say hi to folks, anyone that listened in the past or, you know, has any thoughts in the now. Would love to connect with folks. But otherwise, yeah, thank you so much for having me on.

CHAD: In 2017, I took over from Ben as solo host of the show but was joined by Lindsey Christainson as cohost in 2019. After some time away from thoughtbot, Lindsey is back with us and we sat down to catch up with her.

VICTORIA: Why don't you tell me about your current role with thoughtbot?

LINDSEY: I am currently supporting marketing and business development at thoughtbot, as well as working as a marketing consultant for thoughtbot clients.

VICTORIA: Great. And I understand that you had worked with thoughtbot many years ago, and that's when you also came on as a co-host of Giant Robots. Is that right?

LINDSEY: Yeah, a couple of years ago. I left thoughtbot in spring of 2021. And I forget how long my stint was as a co-host of Giant Robots, but over a year, maybe a year and a half, two years?

CHAD: Yeah, I think that's right. I think you started in 2019.

LINDSEY: Yeah. Yeah, that sounds right. And Chad and I were co-hosts, I think, similar to the setup today in which sometimes we hosted together, and sometimes we were conducting interviews separately.

CHAD: And then we sort of introduced a second season, where we followed along with a batch of companies over the course of the entire season. And that was fun, and we learned a lot. And it was nice to have consistent guests.

LINDSEY: Yeah, that was a lot of fun. I really liked that format. I don't know; they almost were, like, more than guests at that point. They were just like other co-hosts [laughs] that we could rely on week in, week out to check in with them as they're working on early-stage companies. So, every time we checked in with them, they usually had some new, exciting developments.

WILL: I really like that idea. How did y'all come up with that?

CHAD: I'm not sure. I think a few years before I had taken over hosting of the show, and I memory maybe is that I went to Lindsey and said, "You know, let's do something different." But I'm not sure. Does that match your memory, Lindsey?

LINDSEY: Yeah, I think there were two main drivers; one was I think you were feeling like you were having similar conversations in the interviews every time. Like, you couldn't get to a certain depth because every time you were interviewing someone, you were doing, like, the, "Well, tell me your founding story." And, you know, how did you raise funding? It kind of got a little bit repetitive.

And then, on the side, the few we had done together, I think we both really enjoyed. So, we were thinking, like, what's the format in which the two of us could co-host together more regularly? Because I'm a pleasure to talk to [laughter]. I think you were like, I need to talk to Lindsey more. [inaudible 3:13]

VICTORIA: What is your hosting style? How would you describe your approach to hosting a podcast?

LINDSEY: I mean, obviously, it's a podcast about products and business. I think as a marketer, I am, you know, drawn a lot to the marketing side, so tending to ask questions around go-to-market audience, users. That's always just, like, a particular interest of mine. But then also, like, the feelings. I love asking about the feelings of things, you know, how did it feel when you started? How did it feel when you made this tough decision? So, that's another thing I think I noticed in my interviews is asking about some of the emotions behind business decisions.

VICTORIA: And I like hearing about how people felt at the time and then how they felt afterwards [laughs]. And, like, how people around them supported each other and that type of thing. That's really fun.

I'm curious, too, from your marketing background and having to do with podcasts like; some founders, I think, get the advice to just start a podcast to start building a community. But I'm curious on your thoughts about, like, how does podcasting really play into, like, business and marketing development for products?

LINDSEY: Oh yeah. It's become definitely, like, a standard channel in B2B these days. I feel like that it's pretty typical for a company to have a podcast as one way that they engage their audience and their users. In marketing, you're really vying for people's attention, and people's attention span is getting shorter and shorter. So, like, if you have an ad or a blog, you're getting, like, seconds, maybe minutes of someone's attention. And whereas something like a podcast offers a unique channel to have someone's undivided attention for, you know, 30 minutes, an hour, and if you're lucky, you know, checking back in week over week. So, it became a really popular method.

That said, I think you're probably also seeing the market get saturated [laughs] with podcasts now, so some diminishing returns. And, you know, as always, kind of looking for, you know, what's the next way? What's the next thing that people are interested in in ways to capture their attention?

CHAD: What is the next thing?

LINDSEY: I don't know, back to micro-content? TikTok videos --

CHAD: Yeah, I was going to say TikTok, yeah.

LINDSEY: Yeah, you know, 10-30 seconds, what can you communicate?

VICTORIA: I see people live streaming on Twitch a lot for coding and developer products.

LINDSEY: Yeah, I think we've seen some of that, too. We've been experimenting more at thoughtbot with live streaming as well. It's another interesting mechanism. But yeah, I don't know, it's interesting. It's another form of, like, community and how people engage with their communities. So, it's always evolving. It's always evolving, and sometimes it's not. Sometimes, people just do want to get in a room together, too, which is always interesting.

WILL: What has been, in your experience, the good the bad? Like, how do you feel about the way that it has shifted? Because I think you started in, like, 2000, like, kind of earlier 2000, 2005, something around there. And it was totally different than now like you're saying. Because I feel like, you know, Channel 5 30-second ad, you know, with some of the marketing depending on what you're doing, to now to where you're, like, you're paying influencers to advertise your product, or you're doing an ad. Or it's more social media-driven and tech-driven. What has been your opinion and feelings on the way that it has grown and evolved?

LINDSEY: Marketing, in general, yeah, I graduated college in 2005 and started my marketing career. And yeah, you could, like, actually get people to click on banner ads back then, which was pretty [inaudible 07:14] [laughs].

WILL: I forgot about banner ads [laughs].

LINDSEY: I don't know, yeah. I don't know. In order for myself to not just get too frustrated, I think I've got to, like, view it as a game kind of. What new things are we going to try? You know, what do we see work? But it can really depend. And I've always been in B2B side of things. And consumer, I'm sure, has its own kind of evolution around how people engage and how they consume content and byproducts. But in B2B, you know, it can really depend on industry too.

You know, I'm working with a client right now in the senior living space, and they're really big in in-person conferences. So, that's how people consume, get a lot of their information and, make connections, and learn about new products. So, it's been interesting to work in an industry that what might be considered, like, a little bit more old-school channels are still effective. And then just thinking about how you weave in the new channels with the existing ones without ignoring them. They might get information in conferences, but they're still a modern human who will then, you know, search online to learn more, for example.

VICTORIA: It reminds me of a phrase I like to say, which is that, like, technology never dies; you just have more of it. There's just more different options and more different ways to do things. And some people are always, you know, sometimes you have to be flexible and do everything.

CHAD: So, tell us more about what you did in between...after you left thoughtbot, what did you do?

LINDSEY: I was heading up B2B marketing for a company called Flywire, which is headquartered in Boston but is a global company now. And they were just kind of starting their B2B business unit, which, as I mentioned, B2B is my personal specialty. I had been connected to their CMO through the Boston startup community. And yeah, I was helping them kind of launch their go-to-market for B2B. The industries they were in before...they got their start in higher education and then expanded in healthcare and found a niche in luxury travel, and then we were figuring out the B2B piece. But yeah, I was there for about a year and a half.

They actually went public the second week I was there, which was an interesting [laughs] experience. I knew they were, like, on that journey, but it was kind of funny to be there the second week, and people were, like, "Congrats." And I was like, "Well, I definitely didn't have anything to do with it because I just finished my onboarding, but thank you," [laughs].

CHAD: One of the things that really impressed me when you joined thoughtbot was the way in which you learned about who we were and really internalized that in a way where you were then able to pretty meaningfully understand our market, our positioning in the market, and come up with new strategies for us. I assume that's something you're good at in general [laughs]. How do you approach it? How did you approach it when you joined Flywire, for example? And how was it the same or different than how you approached thoughtbot?

LINDSEY: Ooh, yeah, that's a good question. And I appreciate that comment because it's difficult. But I think, yeah, with any new organization that I'm joining, you know, I think starting out with your kind of mini-listening tour of your key stakeholders across, you know, the different departmental focuses to get a sense of, what are the challenges? What are the opportunities? It's actually like, you know, it's the SWOT analysis, kind of trying to fill in your own mind map of a SWOT analysis of where the company is. What are the major hurdles you're facing? Where are people trying to go? What have they tried that's worked? What have they tried that's failed?

But then, like, I think for the culture component, I think a part of that maybe is, like, feel, and maybe something that I do have a knack for. Again, maybe this is, like, you know, emotional intelligence quotient, where it's like, you know, but it's the company, you know, who is this company? What is important to them? How do they work and go about things?

I know thoughtbot is certainly very unique, I think, in that arena in terms of being, like, a really value-driven company, and one where especially, like, marketing and business work is, like, distributed across teams in a really interesting way. You know, I'm sure the fact that it fascinated me and was something I could get passionate and get behind was something that also helped me understand it quickly.

CHAD: I was excited that...or it was sort of a coincidence because I had reached out to you and without realizing that you had left Flywire. And Kelly, who had been doing a combined sales and marketing role, was going on parental leave. And so, it was fortuitous [laughs] that you were able to come back and help us and provide coverage, like, Kelly was out.

LINDSEY: Yeah, it definitely felt like stars aligned moment, which, you know, I'm pretty woo-woo, so I believe in [laughter]...I believe in that kind of thing. You know, yeah, it was wild. It really did feel like your email came out of nowhere. And, you know, I mentioned it, obviously, to my partner and my friends. And they were like, "Oh, he definitely knows, like, that you left your last company." And I'm like, "I actually don't think he does [laughter]. I actually don't think he does." Yeah, and then we started chatting about me coming back to help. And it was great. thoughtbot makes it hard to work anywhere else [laughs]. So, I was happy to come back. I missed the team.

CHAD: And one of the exciting things, and you've mentioned it, is you're not just doing marketing for thoughtbot now. We have started to offer your services to our clients.

LINDSEY: Yeah, I'm super excited about this. And it's something I'd started thinking about. I had decided to take some time off between Flywire and my next thing and had started thinking about doing marketing, consulting. And as I'm doing that, I'm thinking a lot about how thoughtbot does consulting and, you know, wanting to emulate something like that.

So, I started back up at thoughtbot. That wasn't part of the plan. I was just going to, you know, fill in for Kelly and help with marketing things. But then, you know, a good opportunity arose to work on a client, and I was really excited. When, you know, Chad, you and I chatted through it, we came to the conclusion that this was something worth exploring under the, you know, thoughtbot umbrella. And it's been a really great experience so far. And we now have brought on another client now. And if you're listening and need early-stage B2B marketing support, reach out to

CHAD: Definitely. And Lindsey is pretty good, so you're going to like it [laughs].

LINDSEY: Yeah, you're going to like the way you look.

WILL: Yeah, definitely. Because I can even feel your presence here, you know, coming back. Because even like, you know, the market where it's at now and some of the suggestions that, you know, you've been helping us. For example, like, I do a lot of React Native, and you're like, "Hey, you know, blog posts have done a lot of traction, you know, let's get some more blog posts out in the market to help with the traffic and everything."

So, the question I have with that is, like, thank you for even suggesting that because it's, like, those little things that you don't even think about. It's like, oh yeah, blog posts, that's an easy transition to help the market, clients, things like that. But with the market the way it is, what has been your experience working during this time with the market? I don't know if you want to call it struggling, but whatever you want to call it that, it's doing [laughs].

LINDSEY: Yeah, I mean, the economy is difficult now. We also went through a really tough spot when I was here last time. During COVID, you know, we faced a major company challenge. And, I mean, I'll let Chad speak to it, but I would imagine it's probably one of the bigger, like, economic inflection points that you faced. Would you say that?

CHAD: Yeah, definitely. The thing about it that made it worse was how quickly it happened. You know, it was something that you didn't see coming, and then, you know, about 40% of our business went away in a single month. That's the kind of thing that was a real shock to the system.

I think the thing that made it difficult, too, was then the aspects of COVID, where we were no longer able to go into our studios. We were all working remotely. We were isolated from each other. And so, that made executing on what needed to be done in order to make the company survive additionally challenging.

LINDSEY: Yeah, so I think, like, going through that experience, also, and seeing how the team and the leadership team rallied together to get through it. And then, you know, ultimately, I think 2021 and 2022 have, like, really good years. That was a really positive experience. And something I'll definitely take with me for a while is just, like, keeping a cool head and just knowing you have, like, really smart, talented folks with you working on it and that you can get through it.

And just, like, doing some, I mean, we relied on what we did best, which was, like, design thinking, using design exercise to think about, like, how we might re-organize the company, or what other services we might try launching, or how might we re-package, you know, larger services into smaller more palatable services when people have, like, kind of tighter purse strings. So, that was, like, a great educational experience, and I think something we just continue to do now: be open to change, be open to changing how we package services, what clients we go after, and coming at it with, like, an agile, experimental mindset and try to find out what works.

VICTORIA: I really appreciate that. And it aligns now with the new service we've developed around you and the marketing that you provide. And I'm curious because I've had founders come up to me who say they need help with marketing or they need to, like, figure out their marketing plans. So, say you've met a founder who has this question, like, what questions do you ask them to kind of narrow down what it is they really need and really want to get out of a marketing plan?

LINDSEY: I've been thinking about this a lot recently. And, like, obviously, I see other marketing leaders in the market. Marketers like to talk about what they do on LinkedIn [laughs], so I get to...I read a lot about different people's approaches to this. And some people kind of go in and are like, okay, this is what you need. This is how we're going to do it, and they start executing on it.

And I really do take a very collaborative approach with founders. I think they're, especially in early stage, they're your most important asset in a way, and a lot of their intuition around the market and the business, you know, it's gotten them to where they're at. And so, I think starting from the point of, like, taking what they view as priorities or challenges, and then helping them better explore them or understand them with my own marketing experience and expertise, to narrow in on work that's going to be valuable for them, is kind of my starting point with early-stage companies.

Again, a little bit of that, like, listening tour kind of attitude of, like, what do you think is important? And there's probably data points behind that. And then helping you as a company frame that into, you know, what's going to be the most valuable? Like, is it an awareness campaign, or a lead-generating campaign, or a content strategy?

Do we actually need to take a look at the data you have and spend a little bit of effort cleaning that up so that we understand what we're working with better? Is it sales enablement? You know, do you have existing salespeople, but maybe they're struggling or don't have unified tools and messaging that they're using? That's how I kind of first approach it with the founder, very much kind of in lockstep.

VICTORIA: I appreciate that little preview of what your services would be like. And I always really appreciate when you help me with my marketing plans around our Mission Control team and platform engineering and how to really refine our message and make sure it reaches the right people.

LINDSEY: Yeah, I think another thing I used at thoughtbot in the previous time that I've taken with me to Flywire and now with clients is, like, the idea of, like, mini-briefs and working on them with the key stakeholder, whether that's you the head of, you know, a business unit or a founder, which is, like, let's just take the, however long, 30 minutes to talk about, who's the audience? What's our goal? You know, what are the elements that might help us achieve that goal? What are some of the metrics that we might use to measure whether or not we were successful in reaching that goal?

And it sounds really basic, but a lot of people can skip it. And I think then there's confusion around who you are targeting, or people have different ideas in mind of, like, what you are actually trying to achieve.

VICTORIA: I like that. And to pivot a little bit, I wonder if you have any thoughts on our podcast here at Giant Robots. What do you think the benefit of it is to thoughtbot, actually?

LINDSEY: I think it's been a brand builder and a way to, again, like, another channel to engage with our audience. It's been so long-standing now, you know. I talked about how most companies have a podcast now. But this is what? The 500th Episode, right? Over years and years, which is really impressive that it's been going that long. So, it's a way to bring the brand to life.

I think one of my first insights coming into the thoughtbot team is, you know, as a consulting organization, when I interviewed clients about what they loved about thoughtbot, I thought they were going to say that they ended up with amazing products. And they did. They did say that. They said they ended up with amazing products. But I said, "You know, what was the biggest benefit, or what stood out to you the most?" And they all said it was the people, you know, they loved the people. They loved learning from thoughtboters. They were, like, you know, teachers and mentors, and so smart, but also, like, very kind and helpful.

So, when you think about it like that, podcasts or videos and ways you're able to, like, better see and hear and feel the person on the other side is a really great way of, you know, continuing to make that connection with folks.

VICTORIA: I love that answer. I wish we had little heart emojis we could share, like in Google Meets with Zencastr. So, what do you think...Maybe this is a question for everyone on here, too, that we're asking is, like, where do you think we should go with the podcast? What should we change? What should we think about for future episodes?

LINDSEY: I think you should ask the listeners if possible. We tried, in the past, surveying. And it's hard because you don't have, like, necessarily an email list of listeners. But there does tend to be some overlap of, like, our newsletter subscribers with podcast listeners. So yeah, I'd go straight to the audience and just learn more about...ask them what they care about and what they want to learn. Because at the end of the day, it's really for them, providing value for them and something they want to come back to listen to week after week.

CHAD: Oh, when we've done the surveys in the past, we've had very few people [laughs] respond. So, you can always email us at if you have feedback on the show, questions for people, questions for the hosts, or opinions on, you know, who would make a great guest or a direction we should take the show. All that is super valuable. And we definitely would take it to heart.

VICTORIA: Yes, please send me your feedback. I will read your emails and incorporate it into the show. So, it'd be great. I wonder, Lindsey, do you have any questions for us?

LINDSEY: How do y'all like hosting the podcast? [laughs] How's it going?

WILL: I feel like I'm starting to find my style and the way that it works best for me, so that's exciting. I do want to engage more with the listener. So, that's one thing that I'm trying to brainstorm on what's the best way to do that. Also, you know, inviting just different types of guests, trying to think through what's some different type, a different angle that we can invite for the podcast? But as far as how do I like doing the podcast, I really enjoy it. It's pushed me out of my comfort zone. But it was a good thing for me. So, I'm really enjoying it.

LINDSEY: How long have you been doing it, Will?

WILL: A little over a year. So, I think I started after I went on parental leave with my youngest child. And then when I came back, I took a couple of weeks, and then I started. So yeah, about a year, a little over a year.

LINDSEY: That's fun. What's your favorite part about doing it?

WILL: I love talking to the guests. And I love learning, like, people's stories. And so, that has been the most exciting thing for me, like, because especially with the founders, like, it's not easy to be a founder. But people they go all out, and they make a difference. And even through the heartache, and the pain, and just all different levels, but they're willing to endure it because they believe in their product. They believe it's going to make a difference. So, I think the stories, the stories, and the people, meeting new people, and hearing their stories is what I love.

VICTORIA: And I'm the same as Will. I've been on the show for about a year now. And the first episode I recorded with Chad, I think afterwards, he said, "Oh, you didn't ask any questions [laughs]. Like, you were too quiet." But then I think I got a hang of it. And now I really like making people feel comfortable and opening up about their story and hearing, yeah, like the emotions and what it really felt like to go through that. Because, you know, if it's interesting for me to hear that, then I think that our audience will also appreciate it and to feel like you're not alone, right? To build that community and hear those same stories and people going through similar things.

Yeah, some of the guests that we've had on have just been really incredible. And they are people who I admire in the industry, and to have them on the show and to be a part of it has been really special.

LINDSEY: Yeah, that's cool. That reminds me another kind of underlying thing I love about the podcast and the interviewing. It's also low-key, like, market research [laughs], which is interesting, like, better understanding the types of people we provide services to and their kind of drivers and challenges. There's, like, an interesting element there. And yeah, at the end of the day, you get really interested and into it, and you're just, like, having a conversation with them, probably makes for the best kind of episode.

VICTORIA: Right. And then afterwards, you have to, like, pace around the room to, like, decompress [laughs] because you're operating at, like, such a level, at least, that happens to me; I don't know about anybody else.

LINDSEY: No, totally. I would also...if we had, like, an episode scheduled and then it got, like, rescheduled at the last second, I would find I had all this, like, pent-up energy that my body was, like, preparing me to, like, go into the interview.

VICTORIA: Yeah, sometimes I have to get hyped. Like, you got to do some movement right before because you got to get into the zone. But I'm curious, Chad, this is, you know, you've been a host for a number of years now, too. Like, how do you feel about the podcast? Do you still like hosting it?

CHAD: No [laughs]. I'm kidding. I have taken a little bit of a break recently from the ongoing continuous hosting because I was really busy. And it was hard to create the time and dedicate the time to it. But I really like hosting the show. I love talking to different people and learning about their stories. I also really like the episodes where it's able to be more of a conversation with people, and I get a lot of enjoyment out of that.

LINDSEY: We've seen, also, some trends in, like, the episodes where Chad will talk about, like, the business of thoughtbot perform well, too. Because I know there's, like, a lot of folks, who listen who also own agencies or consultancies and always appreciate Chad's transparency around how we run thoughtbot.

VICTORIA: That's interesting. And yeah, I think one of the ways that we've been experimenting with getting the episodes to be more conversational is to have more than one host in the episode. So, Chad or Lindsey, if you're ever wanting to rejoin an episode or invite a founder on and be one of the co-hosts, you're always welcome.

LINDSEY: I'm always down. I love talking. That actually...that does remind me we were thinking...we've been doing live streams that cover thoughtbot's new startup incubator. So, we have the second session currently in progress. But repurposing some of those live streams into, like, mini–Giant Robots episodes. So, that may happen soon. We may do a little bit of that and then give some insight into what it's like week in, week out for founders going through the startup incubator. It's super, super interesting if you're a startup nerd like me.

VICTORIA: That would be great, yeah. We did an episode with Agnes for the first incubator round, and I think that was really interesting. And something we've been experimenting with a little bit is having that diverse group of founders. So, there's founders from companies who the company has managed to survive and excel, and they've been around for ten years or so. Then there's other people who are just starting out. And, like, hearing those stories, too, and, like, the things they're thinking about and what challenges they're facing has been super interesting. Anything else you'd like to promote Lindsey?

LINDSEY: Hire me for all your marketing consulting needs.

CHAD: It was great to catch up with everyone in celebration of our 500th episode. Thank you to Ben, Chris, and Lindsey. But most of all, that you to you. We make the show, but you make the show possible.

You can subscribe to the show and find notes, along with a complete transcript for this episode at If you have questions or comments, email us at
This podcast is brought to you by thoughtbot, and produced and edited by Mandy Moore. Thanks for listening, and here’s to the next 500 episodes!


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