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Michael Pryor, Trello

Michael Pryor

Head of Product (Trello), Atlassian

Michael Pryor is the Head of Trello at Atlassian, the visual collaboration tool that gives millions of people around the world perspective on their projects. Michael is also a co-founder of Fog Creek Software, a software development company that created popular developer tools, including Trello, and sits on the board of Stack Exchange. Michael currently lives in New York with his wife and two daughters.


Mike Butcher: [00:00:00] What gave you the idea for Trello in the first place?

Michael Pryor: [00:00:04] Okay, so... I'll go way back. Wait! Can I do something real quick? Can I see a show of hands of anybody that uses Trello, in the audience? OK. Wow! That was just for me, because like when I come to these conferences, when you're like a software guy, and you're in front of a computer all day long, you know, it's like that's the moment right there.

Mike Butcher: [00:00:25] I have never, ever seen that before. That's incredible.

Michael Pryor: [00:00:27] That's something special.

Mike Butcher: [00:00:29] Yeah.

Michael Pryor: [00:00:32] So the journey started.

Mike Butcher: [00:00:34] I mean there were other products, weren't there?

Michael Pryor: [00:00:35] Yes. So I mean it's, like, built on top of many, many failures. What seems probably like overnight success... I mean Trello, we started Trello back in 2011 at TechCrunch Disrupt, Startup Battlefield... we did not win.

Mike Butcher: [00:00:52] Are you bitter about that?

Michael Pryor: [00:00:54] I mean, I guess not, right?

Mike Butcher: [00:00:56] Are you holding it against me?

Michael Pryor: [00:00:56] We came in second, so I think maybe that's the badge of honour. It's like, because the first-place company doesn't exist anymore...

Mike Butcher: [00:01:03] This happens a lot. It's like we're doing something wrong.

Michael Pryor: [00:01:07] It's like getting featured on the covered of WIRED.

Mike Butcher: [00:01:10] Do you remember Shaker?

Michael Pryor: [00:01:11] Yes. That was the first-place winner.

Mike Butcher: [00:01:12] Oh, they were so bad!

Michael Pryor: [00:01:13] That was the actual winner in our Battlefield.

Mike Butcher: [00:01:16] Yeah, definitely not my pick, promise!

Michael Pryor: [00:01:19] So we started a software company, my co-founder Joel Spolsky, back in 2000 in New York City here, and he started blogging. He wrote a blog, Joel on Software... posted on it a lot, you know, over that decade from 2000 to 2010, and during that time we built a software company, and launched a bunch of products. Like, we didn't start the company to build one product; we just started it to make a fun place for developers to work. I think in New York at the time it was like you could work in a bank, or you could work at an ad agency, but there wasn't really a tech scene there.

Mike Butcher: [00:01:55] Yeah.

Michael Pryor: [00:01:55] So we just wanted to make our own. We did that, and learned a lot of lessons along the way, and we had this, sort of, culture of trying new things. We called them Creek Weeks. The software company was Fog Creek Software, and so we would take like a week — Creek Week — and you know, you've seen Google 20 percent time... So we would just, sort of, try something, try a different thing, and Joel had this idea. To me at the time it seemed like the dumbest idea, but he had this idea that everyone in the company would have a to do list. That would only take five things, like it only had five slots. You couldn't add more than five and you only have one list, and somehow you could see everyone's list — like you could go to a page, you could see everyone's list, and that way he could figure out, basically, what everyone in the company was working on, because that was, we were struggling with that. We had built a software development tool called FogBugz, and it was, it was great at getting all this deep information, but it wasn't really helping us figure out like well what are people working on right now.

Michael Pryor: [00:03:02] So Joel had this idea. He wanted to call it five things or five camels. We were trying to come with a unique name. There's a whole name story there that I can tell, but at first that idea, we sort of played around with it, and we were going out to meet other startups and talk to them. We'd see everyone had post-it notes on their walls that they were using to manage their projects. They were all doing this in real time.

Mike Butcher: [00:03:32] Is it called Kanban?

Michael Pryor: [00:03:32] Yes, so they were a lot of digital Kanban boards at the time, but it was interesting that everyone knew about those tools, but they were still doing this in the real world. Like they were still actually putting physical post-it notes on the wall, and we were trying to distill what was special about that, and why that was so tactile, and sort of rewarding that people would do that over using a software tool, and so those two ideas kind of merged into Trello.

Mike Butcher: [00:04:00] What did you do? What did you think that was different about the way you approach that problem that other people got wrong?

Michael Pryor: [00:04:10] You know there's some things I think we knew from that we intentionally tried to do, and then things that just happened, looking in hindsight, but the intentional things were, very early on, we knew that we wanted to map to that real-world metaphor as much as we could. So everyone looked at the same Trello board, and if you had it on your phone, and I had it up on another computer screen, if you moved a card it would move immediately on the other. So, you know, nowadays that's kind of standard, like, real-time app, yeah... but six years ago that was actually a pain to do on the tech side, and so that was like important because if you're looking at a wall in the real world, you know, and somebody moves the post-it note, you see it. Right, so to try to map to this metaphor that people already understood, which was "hey, you can take notes on a post-it, stick it on a wall." That's what Trello does. That's all you have to get, in order to get what it does, and that can be really powerful. It's like the right level of structure for what you're working on — in fact, the code name for the project was Trellis, which is like a structure for plants to grow on, and this was, like the idea was, that this was to give you structure for whatever process you're working on.

Mike Butcher: [00:05:26] You ended up with, was it 19 million users? How many users was it?

Michael Pryor: [00:05:31] Now 22.

Mike Butcher: [00:05:33] 22, right.

Michael Pryor: [00:05:34] So we went from 10 to 19, I think, in a year.

Mike Butcher: [00:05:38] I'm often asked by startups, you know, what are the best examples of how a company scales from literally a couple of hundred users to millions of users. What are the kinds of techniques and tips and thoughts that you have that? Growth hacking, et cetera.

Michael Pryor: [00:05:54] Yeah, I mean, that's like the question I get a lot, and I really have no good answer for it, because... I mean, I have a good answer, but it's not helpful, which is that you make a product that people love... Which is like OK, but how? What do I do?

[00:06:12] We never spent any money on advertising. So all of those signups are coming organically, because somebody told somebody else about the product, or they you know they invited somebody to work on it: work on a board with them or something like that. Now there's something, I think, if you look at successful collaboration tools, and certainly recently the ones that have succeeded or done really well, there's I think there's a lot of... what I'll call, like, the software is trying to be more human. Like it's... there's more personality in the software. We used to have... You know, a database-backed web site was like a big deal, and then it was like enterprise software was a big deal, and then now I think, like, the way that software delights you, and the way that it kind of surprises you — in a good way, not like a joke, not like a unicorn flying across the screen with the rainbow coming out of its butt, you know, like that kind of, like, delight — but like actual, like, I go to do something, and I kind of hope that'd work, and then it just worked, it, like, did the right thing...

[00:07:18] I'll give you examples. Silly thing, that...iIt's the small things that add up, but, like, if you take a list of items, and you go into Trello and you add it to a card... You go to make a new card, and you add it, Trello'll be like, "do you want to make one card with this list, or do you want to make like 10 with each one as a different item?"

Michael Pryor: [00:07:36] It's just, sort of like, you catch that moment where somebody was trying to do something that may not have been obvious, but the software is like, "oh, I know what you're doing", right? It's sort of like thinking about your users and the kinds of things that they want to do and doing it in a really thoughtful way that delights them.

Mike Butcher: [00:07:58] Very good answer. Do you think that productivity software like that — and there are lots of other solutions out there — but do you think that world is kind of done now, or do you think there's still plenty of areas to mine?

Michael Pryor: [00:08:12] Yeah I mean I think one that space is so competitive right now. You've got... Facebook's there, Google's there, Microsoft's there. You've got startups like Asana. You've got Slack, you've got Atlassian. I mean, there's like so many people trying to get in that space, and I think that that's actually because that space is growing itself – like it's not that these people are competing for a fixed pie, the pie's actually growing really fast. Like if you look back...

Mike Butcher: [00:08:48] So it's not a bad thing that there's lots of competitors?

Michael Pryor: [00:08:50] No, and you know, like, I think some people think like, "oh, there's going to be one winner-takes-all kind of thing", and I don't think that will happen. I think that... at least, not in the near-term. If you look back to right before Trello came out we all got these in our pocket, right? And basically, before that, you kind of had this... A more, stricter division between when you were at work, and when you were at home. Like you had kind of two identities, you know? You had your home person and your work person, and you commute to work. And I think the way that people work in their connectedness is changing, and it's much more fluid and the apps that people are building to help people collaborate are also... they're more consumer-friendly. Like they're things that you would use in your own personal life, but also at work, and that appeal really fits to the way that people think about their devices, and how they're trying to organize their life, or communicate in their life.

Mike Butcher: [00:09:55] You obviously raised money several times.

Michael Pryor: [00:09:59] Once.

Mike Butcher: [00:10:00] Once! Oh, sorry. Once. What's your approach to dealing with investors?

Michael Pryor: [00:10:07] Well, you know, we... So when we built Fog Creek, the idea was, we're going to build a profitable software business, like a bootstraped business that makes money, and we did that. I never raised money. We never raised money for Fog Creek, but... actually, Joel wrote a big article that's been shared a lot about, you know, Ben and Jerry's versus Amazon. Like, two totally different companies and like, when you should take money and when you shouldn't, and you know there's sort of areas where there's a big network effect, and it's a winner-take-all scenario, and then it makes sense to take that money — borrow money essentially... well, not borrow, but sell your shares to get money to speed things up. You basically are exchanging money for time, right?

[00:10:52] You can still build a big business without taking VC money, it just might take you longer. So like, for example, Atlassian built a huge business and they took one round of financing, but it was like right, not long before they IPO'd. So, you know, I think that you can do it in the right circumstances, and I think that in most cases, it's... You know... It's really important to think about the individuals that you're putting on your board, and the kind of support that they give you. I think we got really lucky in the investors that we got for Stack Overflow early on, and that set us up, because since we knew them, and we were successful at Trello, and Joel and I just... We didn't have a typical fundraise for Trello, we just kind of like, "Hey, Bijan" — you know, from Spark Capital — you know, we were like, "hey do you want to invest in Trello?" He's like, "sure, okay." And it was like... Which is not super-typical. We got really lucky. You know, we had a lot of...

Mike Butcher: [00:12:00] But did you base that decision on having a good relationship?

Michael Pryor: [00:12:03] Yeah, I think that's 100 percent... Like the thing, one thing I knew about our investors was, like — and this is really important to me — was that, if everything went to shit, which probably in most cases for startups it does, right? I knew that the first thing out of their mouth would be like, "Hey, how are you doing? Like, how... Are you ok? Like, how do you feel?" Like, it's very much focused about you... Like it's not about, "oh, scramble, like, we have to figure this out and like scrape every last penny..."

Mike Butcher: [00:12:33] Punching you around the head and, "Get it right!"

Michael Pryor: [00:12:34] Yeah. Because I think, like, running a company is super stressful. You don't have a lot of support. There's not... It's hard to find peers, right? If you're inside your group, and you're growing your group, you're like... everyone's coming to you with their problems. Who do you go to? You know.

Michael Pryor: [00:12:48] So I think that's basically it's a support group you're building on your board, and so if you have people that are not really thinking about it the right way, then that can be a really stressful situation. You're getting squeezed from the top in the bottom.

Mike Butcher: [00:13:05] You eventually got to the point where, so, reportedly Mike Cannon-Brookes from Atlassian was building, was doing some renovation on his house, using Trello...

Michael Pryor: [00:13:16] Yeah, I think...

Mike Butcher: [00:13:17] Was that how the story went?

Michael Pryor: [00:13:18] I think he's... He was using Trello. He's a fan, and he sent us, he sent Joel an email, and said he was going to be in New York, and wanted to know if we were around, or... I said, "sure." We were, at the time, we were thinking about doing a B-round... to go out and raise again for Trello, and had a lot of interest from investors, and so I was like, okay, this is the perfect time, we'll talk. I kind of suspected what he wanted to talk about. And so we went to this Mexican place near my office, and had lunch, and it was funny because I didn't know it at the time, but he had flown all the way from Sydney for lunch, and then flew back, like...

Mike Butcher: [00:14:08] Really?

Michael Pryor: [00:14:08] I just was like, "oh he's in New York, like sure, I'll just meet up..."

Mike Butcher: [00:14:11] So it wasn't just casual?

Michael Pryor: [00:14:13] No. And Then, it was also kind of funny, because I thought, you know, I'm like, "okay, so, probably thinking about acquisitions. So what's this lunch going to be like?" I'm suspecting, you know, he's going to show up with a little piece of paper with the number on it, and slide it across and I'll be like, "oh!" I have to, outrage, like I...

Mike Butcher: [00:14:34] "How dare you?!"

Michael Pryor: [00:14:34] But we just sat there and had this hour and a half long conversation about product, and people, like the the the people in the company, and what we wanted Trello to be, and where we saw it in the future, and just like our values. There was this like, I don't know, it felt very much like I was talking to somebody that I had known for a very long period of time. It was like they had started Atlassian around the same time that we started Fog Creek and it had gone through a similar era, had a lot of success. So I had a lot of respect for what they had built. And you know at the end of it, I went back to the office and I was like, you know, it's kind of like, "Did he try to acquire us?" I wasn't sure. Like we just had a great conversation, but I don't know what happened, and...

Mike Butcher: [00:15:25] Who paid for lunch?

Michael Pryor: [00:15:27] I don't remember. That's a good question. I don't recall. But you know, later, and then as we looked... We kept having conversations about this, and trying to figure out like, well, we share the same vision. In fact, that was one of the points he asked me, was like, "What are you..." When he was talking to me about, "where do you want to take Trello?" And I said, you know, "Joel got up on stage at TechCrunch Disrupt and launched this product and said, 'we want to build a product 100 million people use.'" Which, when he said a hundred million, that was just a ridiculous number that he made up to signify how broad we wanted the product to reach, not a real number, okay? But now we're getting to the point where, oh, that's actually a pretty good goal for where we are now. 

[00:16:13] And he laughed, and I was like, you know, "Are you... Was he like making fun?" Like, did he think that was ridiculous when I was saying, you know? I'm like... He said, you can go look this up, I'm not making this up, he said, "We used to have a big hairy audacious goal inside the company to get to 60,000 customers, and we passed it, like, you know, a couple months ago or something, so we had a big exercise like what do we want our next big goal to be?" And he's like, "we want 100 million people to be using our products." And it was just like... It was a simple thing, but I think, like, that kept happening where there was a lot of overlap between the way that we thought about what we were trying to do, and the kind-of companies that we were trying to build, and as we looked at it more, I just thought this is a really good outcome for both of us.

Mike Butcher: [00:17:05] Atlassian's made a number of acquisitions prior to you guys. What do you feel is — how do you feel that there is there a, kind of a transition process, or are they sort of just letting you get on with it?

Michael Pryor: [00:17:18] So they had done...

Mike Butcher: [00:17:19] Sometimes when companies get acquired, there's a "Oh shit! How do we fit into the organization?"

Michael Pryor: [00:17:24] So they had done 18. I think we were the 18th acquisition that they had done, so they had a lot of experience with this. They had done, never one of the size that we had. We had about 100 people. So this was a big deal for them to get this right. And one of the things that I really admired about them during the conversation, Mike and Scott, was that they're very... It was very important to them when they do something to do the retro, and look at mistakes that they had made, or like to learn from the mistakes. And you could, I could tell as we went through this process, there were specific things that they were doing, that they had learned from from a previous acquisition.

Mike Butcher: [00:18:06] Could you give us an example?

[00:18:09] Like, there were... Well one, putting the alignment on people and culture upfront, instead of the financial aspect of it in the terms. So it was like, focus on that, because if there's not an alignment there, then what does it matter. Like, you know, you only live once. Like why would we do... They don't need to do this, right? So you want it to be fun. You want people to have fun. You want it to work and have the people fit together. That was one thing.

[00:18:42] There was, when we... after the acquisition took place, they placed a 'do not disturb' on the Trello group. They basically said to the rest of Atlassian, "don't disturb Trello." And they created an integration stream. So we had a couple, like three little meetings to like make sure that we could get information across, but the reason was that previously they had seen that if you have a small group of people, and then you have this giant group of people, everyone... Best intentions, positive intent, they want to help, but it can be really overwhelming. So like you're like I guess I'll have a meeting. I guess I'll have this. And then you realize like, you've just slowed down. You were running this product with this team of people and now you're spending all your time talking to the broader organization, and you know, they're trying to help, but you're just stuck in meetings, and not doing things. So you have to make that process more gradual. So we basically run as a standalone product and try to limit, you know, the things that are going to slow us down.

Mike Butcher: [00:19:45] So where are you nowm and what's happening now?

Michael Pryor: [00:19:49] It's been six months, you know, and I think you get through the initial, there's... It's like you quit your job and you got a new job right. You have to do all the paperwork, come on onboard to the new systems, and that kind-of thing, and I think there's, you know, we've had 100 people at our company, and now we're part of a 2000-person public company. So we had to get our books closed on a timely basis, and there were a lot of things that we had to check off early on. Got those done, but day to day, from the product perspective, not much has changed. So I report in to Mike, one of the co-founders, and the product roadmap for Trello is, if anything, moving faster, one of the first things that we did was, we took all of our internal hiring needs, and we sort of like said, "Hey, do you have any great people at Atlassian that want to work on Trello?" And we've got 12 amazing people like that.

Mike Butcher: [00:20:49] Yeah.

Michael Pryor: [00:20:49] And the best part about that was those people are super experienced, and when they came over... the difference between when you hire someone and it takes them a little time to ramp, these people were like checking in code, like, day one. You know like fixing bugs day one. So that was super helpful. And there's just a lot of resources there, and a commitment to invest in R&D and build an amazing product that, you know, just basically helping us move faster than we were before.

Mike Butcher: [00:21:15] Yeah. Sometimes when acquisitions happen the product sits on the shelf, and then it will kind-of just sort of stay status doesn't it.

Michael Pryor: [00:21:24] Yeah.

Mike Butcher: [00:21:25] It's kind-of disappointing sometime.

[00:21:26] I think it's like, what was the intention of the acquire? Did they acquire to sort of just take that out of the, you know... Or are they... But for us, there's a lot of investment happening in our group, and what's the the term for this, is like the: Atlassian goal is to unleash the potential of every team. And I think that, you know, that goal: the important thing there is every team. Like, they've obviously had huge success on the technical side, and I think Trello helps them accelerate that getting closer to that every team part of the goal.

Mike Butcher: [00:22:11] Do you, you know, obviously you seem pretty happy, and you're, you know, you've gone a fantastic exit, and you're obviously still excited about the product itself. Do you feel, obviously it's a little bit away in the future, but do you feel you've got a few more acts to go?

Michael Pryor: [00:22:25] Yeah.

Mike Butcher: [00:22:25] A Few more startups in you?

Michael Pryor: [00:22:27] Oh, more startups? I got more. Here's the thing: when there are so many features, and things like we have to do at Trello, like the list in the board that we have is just like it's gotten...

Mike Butcher: [00:22:39] Like, what is the Trello board like?

Michael Pryor: [00:22:42] It's got a lot of cards on it. I think there's a little warning that says like, "you have more than 500 cards on this board. Please archive some of these." So that's good. No, but there's there's so many things that we have to do in the product that, you know, I haven't even thought about that yet.

Mike Butcher: [00:23:02] That's for another time. Yeah. You've got a large Trello board to deal with it at the moment at Trello. Well, I think we've... We've heard so much about you. It's fantastic to meet in person and you hear about you.

Michael Pryor: [00:23:13] Thanks for having me.

Mike Butcher: [00:23:14] Pleasure. Thank you so much.

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