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

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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Transcript:

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 do...so 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: hackersincorporated.com. 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 just...no 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 about...it'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?

CHRIS: No.

CHAD: Oh. How does that make you feel?

[chuckles]

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 is...it'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 helps...it 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.

CHRIS: Yes.

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 your...do 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 do