Get in touch

Postlight joins Launch by NTT DATA! Learn more.

Throughout his engineering career, Andrew Childs used his fair share of project management tools. None of them felt quite right, so he quit his job and built his own — Andrew joins Paul and Rich to discuss why the tool has become so popular at Postlight, and how it’s managed to survive in such a crowded project management marketplace.


Andrew Childs My favorite story from those four years was I personally broke

Paul Ford Oh, that’s good.

AC For a day.

Rich Ziade Thank you for doing that, we appreciate that.

PF That is an important lesson.

RZ That is like a bucket list thing. [Andrew laughs]

PF Just the sheer destructive power you have in your everyday job when you’re doing engineering is just wonderful.

RZ It’s wonderful. [music ramps up, plays alone, fades out]

PF Richard!

RZ Hi, Paul.

PF You know, a funny thing happened about, I don’t know, I would say about a year ago, I started to get all these invitations to a new product, a new service. 

RZ Ohhh Vine?

PF No, it was called Clubhouse.

RZ I mean, I obviously, I know. It makes sense. You’re a podcaster.

PF No, no, has nothing to do with that. This is a different Clubhouse focused on project management for engineering groups.

RZ Okaaay.

PF You hear about this?

RZ It’s also called Clubhouse?

PF You’ve also received invitations.

RZ I have it. It’s very good. 

PF It is. We’re not going to talk about that. It just so happens that there’s a semantic collision around Clubhouse. 

RZ Yes. So this is

PF That lets you move the boxes around with the things that you do on them.

RZ Mmhmm. That’s a good summary.

PF It’s very fast. That’s the big deal about Clubhouse. 

RZ This is why Postlight loves it actually.

PF Speed is the number one ethos in our engineering culture. And it’s also a New York City oriented startup, which is very exciting.

RZ More love because of that. 

PF And today, well, why don’t you tell us, you’ve actually established this relationship. Who is on the podcast with us, Rich?

RZ Andrew Childs.

PF Yay!

RZ The founder of

AC Hello!

PF Hey, welcome. Glad you’re here.

RZ Welcome to the Postlight Podcast.

PF And the Postlight office, we’re all in one room.

AC I’m so excited to be here.

RZ We’re excited to see you in real life.

PF Andrew brought doughnuts.

RZ He did bring doughnuts.

PF No guest ever has brought doughnuts.

AC I know how to come back to an office.

PF Snacks are the number one—everyone is like very concerned about remote work. And I think snacks are a major driver for office culture.

RZ No doubt. No doubt. 

AC I mean, you can mail doughnuts.

PF We do it. We mailed ice cream last week.

RZ We mailed ice cream.

PF You missed it, man. That was some unbelievable ice cream.

RZ I got to get that ice cream.

PF Rich didn’t put his name on the list.

RZ I forgot to put the name on the list.

PF Yeah, it’s like macha flavor. It actually wasn’t cool, because you just kind of keep going back. Anyway.

RZ I want to hear the origin story. But before then give us the elevator pitch. But the elevator is only in a three storey building. Well, what is Clubhouse?

AC So clubhouse on the 10 is project management software, I would say there’s a big impact that we’re going for and there’s a little impact. One of them is, you know, on the little impact side, you know, we’re trying to build a product that allows your software team, right your engineers, your product people, your designers to plan and manage and document your work in a way that doesn’t make you angry. [Rich laughs]

PF Ah, this is really important. Because I don’t know if anyone out there has ever used—I’ll name a competitor, JIRA. JIRA will make it piss you off real bad, real fast, like people just get angry. It’s just like, they set it all up. And then there’s people whose job it is to set it all up. And then you get roped in and you have to like, and you’re just like to hell with this. I guess the software is just gonna, I guess our product is gonna suck, because I’m not going to figure out how to use this. 

RZ Yes, yes, I’m gonna name another one that I think and I’m gonna wade into potentially dangerous waters here. I think Basecamp is a lousy product. I’ve always thought it was a lousy product for many years. I never understood. I get it. I think people fell into the patterns around Basecamp and then defended it. But I never found it to be very good. Yeah, I guess so, you waded into waters that are that have a lot of players. Why go there? Like what made you confident that this thing was going to was going to be different?

AC I think a lot of this stems from my experience, and my co-founders experience that our last company, we you know, saw our our startup go from, you know, a team of 10 people up to over 100 people. And throughout that four years that we were there. We saw you know, we were using a product called Pivotal Tracker.

PF Oh, sure. 

AC And that was a great product for what it what it was designed to do. 

PF It was kind of interesting because they were software development for hire. But they had this data encapsulated their whole process into the tracker software, which they then resold and so it was just like, as an agency, that’s a really interesting model to be like our process is so good. We turned it into software. You should buy it. Right, then later someone bought them, which I think is another kind of outcome you get. So what was this last company by the way? I’m curious.

AC It was an ad tech company called Intent Media.

PF Okay. 

AC They were based in Soho.

PF Alright, so not, you like to stay on a relatively small number of train lines? 

AC Yes, yes.

PF We do too. Okay, so you’re there, you’re using—

RZ What was your role there?

AC I was pretty much the first designer and frontend engineer. So kinda small—

PF It was little, so you got to do everything. Okay. Yeah.

AC I did learn a lot about JavaScript. And, you know, building kind of a simple framework and architecture there, because we were placing JavaScript on travel sites.

RZ Okay, so you’re there. So you’re using this tool.

AC Yeah. And, you know, I got to see before this, I was basically running my own little agency. I mean, if you’re one person, you’re really not an agency. You’re just a person.

RZ Independent.

PF You can pretend. [Rich laughs]

AC Refer to ourselves as ‘we’.

PF That’s freelancing! Okay, so yeah. 

AC So but, you know, at this startup, when I got pulled into the startup world, I got to see how software teams work, how the process that they come up with kind of emerges and evolves and kind of falls apart as you as you go from 30 people to 50 and 50 to 100.

PF What broke? I’m very curious, where where did you go like, oh, man, this isn’t working anymore?

AC A couple things. One is when we built a QA function, and in Pivotal Tracker, you have a rigid, kind of fixed workflow. And they have terms like, delivered and approved. And they don’t necessarily map to—

RZ Funny how they commit to them verbs in these tools. Pretty hilarious.

PF But see, the flip side there is will allow you to define any verb you’ve ever wanted.

RZ Which is also just potentially—

PF Yeah. And then then you have enterprise problems. Yeah.

AC Yeah, when one aspect was the workflow, but then also people were working across different projects. And there was no way to see kind of high level, what was happening. Projects were looked at in isolation, and you couldn’t do kind of high level planning, or there’s no way to really observe the organization. 

PF Sure. 

AC Once we got to say 50 people. So this led to Kurt, my co founder, who was the CTO at our last company said, okay, we need to move to JIRA. JIRA is the industry standard.

PF Buh-buh-buhhhh.

RZ Things that inspire people, Paul. Okay. 

AC And so, that happened, we exported everything out of Pivotal Tracker imported into into JIRA. And I can’t explain why. But something about just completely destroyed our kind of day to day, working lives.

RZ It was just enormous friction for the whole group.

AC Oh, yeah. And, you know, it wasn’t like, information architect. I mean, it was it was everything about it. So it just, it became really painful to use. So this coincided with a hackathon.

RZ JIRA in the background, dark days. Nobody’s happy.

AC Yep. And so what happened was, I was thinking, what if we move back to Pivotal Tracker, but built a kind of Trello-ish, like kanban UI on top of it Pivotal Tracker.

RZ On top of it. Because Pivotal Tracker has an API, you could—okay, okay.

AC So we did that. I should say, I did that and built this Hack Day project, a project that allowed us to see across project what was going on.

PF See everybody, it could be a better world. Right? 

AC Yeah. And so you know, I demo that people liked it, we actually moved the entire engineering team back to using a Hack Day project. 

RZ So you went off JIRA?

AC We went of JIRA, we export everything out JIRA, imported it back into Pivotal Tracker.

RZ Wow. 

AC We actually open sourced that library and talk to some of the people from Pivotal Tracker. And they were like, this is very interesting, what are you going to do with it? And we’re like, nothing.

PF Do with it? Now you gotta get back to work. Yeah.

AC But then six months later, you know, Kurt and I were sitting in the cafeteria, as one does in an office.

PF Eating donuts.

AC Eating doughnuts, looking at each other. And we’re like, well, if we replace the Pivotal Tracker API with our own API, we can back out of all the decisions that we didn’t agree with. And kind of went in our own direction with it. We could, it felt like a very organic move. Yeah, organic kind of opportunity. And the thing I would say about all of the products in the space, it is a very, very crowded space. But, you know, all of these products are, they go in a certain direction. They’re very much based on the original people that designed it. You know, and the opinions and thoughts and feelings that those original people had are baked into the product. You know, and they, they kind of go in different directions. And it just felt like nobody really nailed it.

PF You’re like, we’re, it’s, it’s our turn. We’re gonna give it a try. How big is this market overall? Did you size it? Like, how did you approach that?

AC It’s billions. Sure. I mean, when we did our first seed, pitch deck, I think it was 4 billion, maybe. 

PF So you’re like, let’s build this API. Did you go out and raise? What did you do next?

RZ Well, don’t go there yet. Like tell me about the leap because you’re still at the job in the cafeteria.

PF Yeah. But it’s a startup. So the signal is like, come on.

RZ Do you quit your jobs? 

AC Like, yeah, and you know, I had, I don’t know, eight months of savings.

RZ Good on you. Your cofounder quit too?

AC He quit too. It took a couple more months for him to leave because he was involved in fundraising.

PF The thing about the startup though. Say, you look them in the eyes. You say, I gotta go build this. And they’re there. You know, it’s an ad tech startup. Okay, what are they gonna say?

RZ Right. Okay, so off you go. And raise some money.

AC We raised some money. You know, it was just the two of us for a year or so. 

RZ Coding, designing, launching.

AC Coding, building, it’s wonderful. [Rich laughs] Just making decisions left and right. 

RZ Yeah, those days are gone for you now. You don’t get to do shit now!

PF To be clear, Rich said to me, like, let’s do that, let’s you and me start something together. And then he’s like, you know what, though, we can also build an agency.

RZ That is a great feeling right? When you’re able to—the feedback loop is so tight. Signal is so strong.

PF Two people in a room can make a lot of progress. 

RZ It’s incredible. I think you can get to four or five, I think that the human tax kicks in, the human communication tax kicks in. That’s my number.

PF What was launch day like? What was it like when this thing went out in the world?

RZ Where are we? What year are we? When you and your co-founder together in a room? What year is that?

AC So I left in January 2014. Started working on this. And then a couple months of fundraising. 

RZ You got like a seed round or whatever? 

AC Yep, we did seed round and then Series A and Series B. It took about two years, I would say to get to the point where we could actually allow people to pay us.

PF Yeah, of course, of course. Alright. So two years to truly a viable, not an MVP, but a viable product that people can spend money on. Do you remember that first customer?

AC I do. I remember that first meeting actually, with it was a startup called Timehop?

PF Noooo, it was Timehop? We know Rick Webb? Yeah, yeah, yeah, sure. Okay. 

AC And that was our first actual usability test.

PF No kidding. 

AC Yeah, it was, it was brutal. You know, the first minute was like, oh, wow, there’s 20 bugs and 20 usability problems.

PF It’s horrible to be beheld isn’t it? Yeah. 

AC Oh wait, of course, you want to use your keyboard to do that. [Rich laughs]

PF You like when things work. That’s, wow. Okay. I didn’t factor that in.

AC But that’s what’s, you know, something that’s been really interesting and fun about this. I mean, I think of it as a project. It’s, you build the thing, and then you’re just polishing and polishing and polishing. And then more people come in, and they want to build an add and add and add stuff. And then you’re like, but wait, we need to keep polishing and polishing it.

RZ Okay, this is an interesting thought, because it’s something I got my roots, roots or product management, also. And my inclination is to strip down and make the core better. Whereas a lot of times, people and by people, I mean, anyone, it could be designers could be other product managers, it could be engineers want to solve through more software? And do you feel like that’s part of why you’ve seen success with Clubhouse, that you stayed true to the core thing that you the core principles behind it?

AC I think so. I think that’s what’s gotten us to where we are today.

RZ You’ve done a few things extremely well.

PF Help us quantify today just a little bit, I’m, it’s totally fine. If you don’t want to share numbers, but like, size of community, like, you know, any big customers anything sort of help people understand where this thing sits in its market?

AC Well, it’s a big market, we’ve got 1000s of software companies, and agencies, like Postlight paying us and have a free base, free user base of teams that are between one one and 10. And then 10s of 1000s of customers.

PF Okay, so 1000s of paying customers. I don’t have that.

RZ We own an agency, Paul. It’s a different game.

AC The difference between an agency and, you know, product company is an interesting topic, too. I mean, what’s interesting about Postlight, too, is even just within agencies, right? There are product development agencies, and like multi disciplinary agencies like Postlight. Right. And then there’s very specific specialized agencies that only do marketing or only do design.

RZ Yep. We cut across.

AC Yeah, this is why I think it makes sense that Postlight is a customer of ours because you act and you know, you’re very similar to a start up.

RZ We launch product pods, then are discrete teams that go out to do the thing. That’s absolutely true. That’s why I think we gravitated towards it. Versus like augmenting teams, which we’ve done occasionally. But mostly, they’re full full on product teams. 

PF Also, we have the ability to drive the product stack. Yeah, right. And so like what people reacted to most strongly about Clubhouse was speed. They were just like, boy, this is fast to use. I think it was just that sense of—

RZ I think it was straight forward, too. That was another thing.

PF Yeah, we’re also a JIRA customer because our clients need it. And I think there is that, that real sense of like that friction is an enterprise artifact like it takes a while and you can do everything with it. And it’s still better than nothing but and we’ll, we’ll adapt as we go. But if you give us our druthers, we’re going to use the smaller, faster tools that are good for like the five person team, not the 500 person team. And so that’s it’s just spread throughout the org, kind of just like that. There have been a few, Whimsical did that, Mural is doing that now a little bit of Mural. But Clubhouse definitely took over. We find out because the bills come due, we’re like what’s this one?

RZ Clubhouse is supposed to fail. Most of these things are supposed to fail, especially ones that are wading into waters that have these behemoths that dominate the space. Why didn’t it fail?

AC That’s a good question. I honestly don’t know. I mean, I think I could say—

PF That it is the best product answer.

RZ That is a humble leader right here in front of us, Paul!

PF It’s a lot easier to be humble when it’s working pretty well.

RZ Was it a killer feature?

AC Well, I mean, it was I think it’s been, it’s been validating, to see and have all these customers that validate and repeat back like, yes, we have the same exact problems that you had, that you tried to solve in this product. A big part of it is not trying to do too much,

RZ You didn’t get into a future war with a platform that’s been around for 15 years and has 1000s of features.

AC And that’s just that’s the big challenge, I think, for us and for me as a designer is to push back, like you never want to say no, to, to customer or to request because you can, you can always say you can always solve any problem, right? But you got to think about the whole, right the system as a whole. And when you have a product like this that you’re working on for almost a decade, you have wave after wave of people asking for things. Nobody’s writing into say, don’t build this feature. [Rich laughs]

PF No. 

RZ Keep it simple! Keep it simple Clubhouse! You just be you.

PF That’s a very specific kind of customer. You know, where you see this happen? It also it feels like your particular audience. Enterprise customers are brutal, right? Because you see it actually see, like, even the big cloud services, like there’s this very funny thing where Google, we’ve talked about this in the podcast, like Google Cloud, whenever they go out in public, and they do a deck half the time and includes like, they’re awesome Gardner statistics, just like Google needs Gartner to tell people they’re okay? But you need that validation from Gartner. And then the enterprise customers come in, and this is for all the big cloud services and a lot of them where they’re just like, I’m gonna need that q3, you’re gonna you know, but then we’re going to buy a trillion dollars worth of services once you get it for us. And it just likes slams the roadmap over and over and over again.

RZ I think I’m going to reference an article I wrote, which is terrible. I’m sorry, I’m apologizing in advance. I wrote an article called Backlog Driven Development, which is essentially—

PF Available on the Postflight website.

PF So good place to work.

AC We care about what we do good. Customers care to. Because they tell us. [Rich laughs] 

PF No but I mean, you know, Postlight loves itself some Clubhouse, of course, you know what’ll happen? We’ll go in Slack will be like, “Hey, we talked to one of the cofounders at Clubhouse, they’ll be like, well, you know—”

RZ “We’ve moved on to Winkeedoodle…”

PF No, they definitely haven’t moved on. But if there will be sort of like “It’s been interesting what they’ve been doing… bah bah bah”

RZ That’s not the voice either of the team at Postlight.

PF [Paul in deeper voice] “They’ve been making some interesting decisions.”

RZ There we go.

PF That’s that’s what our engineers sound like on Slack.

RZ Thanks again, Andrew. This was great, great conversation. 

PF Thank you for bringing doughnuts. 

RZ Thank you for the doughnuts.

PF Didn’t bias us in any way. 

RZ Not at all. 

AZ Greenpoint, man.

PF Greenpoint! For people who aren’t in New York City. It is a very specific neighborhood. Not Williamsburg. It’s Greenpoint.

RZ Reach out. 

PF That’s all you gotta do.

RZ And check us out at Lot of good case studies.

PF Big clubhouse users.

RZ Big clubhouse users. Have a wonderful week, everyone. Thanks again, Andrew. 

AC Thank you. 

PF Thank you! [music ramps up, plays alone, ends]