Trello can look like an overnight success, but it grew out of a decade of experiments and failures at Fog Creek Software - and a deceptively simple idea about a to-do list with only five slots that eventually collided with the humble post-it note on a startup's wall.
Michael Pryor tells how Trello was built around a real-world metaphor people already understood, why the team obsessed over small moments of software delight, and how it reached over twenty million users without a cent spent on advertising. He's frank, too, about raising money just once and the Atlassian acquisition that began with Mike Cannon-Brookes quietly flying from Sydney to New York for lunch.
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What what made you what what gave you the idea for Trello in the first place? Okay. So I'll go way back. Wait. Can I just do something real quick? Can I see a show of hands of anybody that uses Trello in the audience?
Okay. Wow. I have never seen that 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, know, it's like that's the moment right there. I have never ever seen that before, that's incredible.
It's amazing. That's something special. Yeah. So the journey started I mean there were other products, weren't there? Yeah. The 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 twenty eleven at TechCrunch disrupt. Yes.
Started Battlefield, we did not win. Are you bitter about that? No. I mean, guess not. Right? You holding it against me? We came in second, so I think maybe that's the badge honor. It's like because the first place company doesn't exist anymore. This happens a lot.
Like covered of wire. Remember the shaker? Yes. That that was the first place Oh, they were so bad. That was the actual winner in our battlefield. So They definitely not my fault. Promise. So we we started a software company. My co founder Joel Spolsky back in two thousand in New York City.
Yeah. And he started blogging. He writes a wrote a blog Joel on software posting on it a lot, know, over the over that decade from two thousand to twenty ten. And during that time, we we built a software company and and launched a bunch of products.
Like it 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 at a bank or you could work at an ad agency, but there wasn't really a tech scene there.
Yeah. So we just wanted to make our own. We did that and learned a lot of lessons along the way. And and we had this sort of culture of trying new things. We called them CreekWeeks. The the software company was Fog Creek Software, and so we would take like a week, CreekWeek.
And, you know, you've you've seen Google twenty 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, you only have one list. And somehow you could see everyone's list. Like you go to a page and 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 FogBugs, 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? So Joel had this idea. He wanted to call it five things or five camels.
We were trying to come up with a unique name. There's a whole name story there I can tell. But at first, that idea, we sort of played around with it and 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. Right? They were all doing this in real time. And Is it for Kanban? Yeah. So there were there 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 notes on the wall. And we were trying to like, 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. What did you do what what did you do do you think that was different about the way you approached that problem that that other people got wrong? You know, there's there's some things that I 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 it 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 under understood, which was, hey, you can take notes on on a on a on a post it, stick it on a wall. That's what Trello does. Like, that's all you have to get in order to get what it does.
And that can be really powerful. It's like the the right level level of structure for what you're working on. In fact, the the 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 give to give you structure for whatever process you're working on.
You ended up with was it nineteen million users? How many users was? Now twenty two. Twenty two. Right. Yeah. So we went from ten to nineteen I think in a year. I'm often asked by startups, you know, what 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 on that? Growth hacking Yeah. Mean, that's like the question I get a lot, and I I really have no good answer for it because I 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, okay, but how?
Right? What do I do? We never spend any money on advertising. So all of those sign ups 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 it's there's more personality in the software.
There's more like, you know, we we used to have you know, database backed website 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 kinda 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 like actual like, I go to do something and I kinda hope that work and then it just worked.
It like did the right I'll give you examples. Silly thing that that it'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 car you go to make a new card, you add it.
Trello will be like, do you wanna make one card with this list or do you wanna make like ten with each one as a different item. Right? And 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? So that helps you. 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. 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?
Yeah. I mean, I think well, that space is so competitive right now. Right? 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 is actually growing really fast. Like if you look back So it's not a bad thing that there's lots of No.
I you know, like I think some people think like, oh, there's gonna 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 near term. If you look back to right before Trello came out, we all, you know, got these in our pocket.
Right? You and basically, before that, you kinda 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, know, you had your home person and your work person, you commute to work.
And I think the way that people work and 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 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 what they've how they're trying to organize their life or communicate in their in their in their life.
You you've obviously raised money several several times. Once. Once. Oh, sorry. Once. What's your approach to dealing with investors? Well, you know, we so at when we built Fall Creek, the idea was we're gonna build a profitable software business. Like a bootstrap business that makes money. We did that.
Raise money. Yeah. We never raised money for Fog Creek. But actually, Joel wrote a big article that's been shared a lot about Ben 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 like 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 so that you get money to speed things up.
You basically are exchanging money for time. Right? 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 never 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, the the it's 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 with 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 wanna invest in Trello?
He's like, sure, okay. And then you know, was like, which is not super typical. We got really lucky. But you know, we had a lot of But do you debate that base that decision on having a good relationship? Yeah. I think like that's a hundred percent.
Like the the thing one thing I knew about our investors was like, and this is really important to me was that if everything went to ****, which probably in most cases for startups it does, right? I knew that they the first thing out of their mouth would be like, hey, how are you doing?
Like, how are you okay? Like, how do you feel? Like, it's very much, like, focused about you. Like, it's not about, oh, scramble. Like, we have to figure this out. Like, scrape every last penny piece. Punching punching around the head and get it right.
Yeah. Because it 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 Yeah. Like everyone's coming to you with their problems.
Who do you go to? You know? So I think like 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 and the bottom. You eventually got to the point where so so reportedly, Mike Cannon Brooks from Atlassian was built was doing some renovation on his house, and he was using Trello. Yeah. I think he Is that how the story went?
Well, 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 gonna be in New York and wanted to know if I if we were around or, you know, I I didn't I said, sure.
We were at the time, we were thinking about doing a b round of to go out and raise again for Trello. And had a lot of interest from investors, and so I was like, okay, is the perfect time, we'll talk. I kinda 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. Really? I just was like, oh he's in New York, like sure I'll just So it wasn't just casual.
No. Then it was also kind of funny because I thought, you know, I'm like okay, so probably thinking about acquisition, so like what's this lunch gonna be like? I'm like suspecting, you know, he's gonna like show up with a little piece of paper with a number on it, and like slide it across, and I'll be like, oh, I have to you know outrage like How dare you?
Thought this was No, but we we just sat there and had this like hour and a half long conversation about product and people. Like the the the the people in the company, and the 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. I felt very much like I was talking to somebody that I had known for a very long period of time. It's like they had started Atlassian around the same time that we started Fog Creek and had gone through Yeah.
You know, 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, was kinda like, did did he try to acquire us?
I wasn't sure, we just had a great conversation, but I don't know what happened. Who paid for lunch? I don't remember. That's a good question. I don't recall. But, you know, later and then as we looked, we 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 do 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 his product and said, we want build a product that one hundred million people use.
Which when he said one hundred million, that was just a ridiculous number that he made up to signify how broad we wanted the product to reach. Right? 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.
And he laughed, and I was like, you know, are you was he like making fun of like did he think that was ridiculous, what I was saying, you know. But 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 sixty thousand customers. And we passed it like, you know, a couple months ago or something. So we had this big exercise, like what do we want our next big goal to be?
And he's like, we want a hundred 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. Atlassian's made a number of acquisitions prior to you guys. Do you feel is how do you feel that is there a kind of a transition process?
Or are they sort of just letting you get on with it? So they had done Sometimes when companies get acquired, there's a, oh, ****. You know, how do we fit into the organization? Yeah. So they had done eighteen. I think we were the eighteenth 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, like a we had about a hundred 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. Could you give us an example? Like, they were well, one, putting the the alignment on people and culture upfront instead of the financial aspect of it and 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 like, they don't need to do this. Right? Like so you want it to be fun.
You want people to have fun. You want it to work and have the people fit together. So that was one thing. 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 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.
Sort of So like, you're like, oh, guess I'll have a meeting, I guess I'll have this and then you're you realize like, you've just slowed down. You were running this product and this with this team of people, and now you're spending all your time talking to this broader organization.
And, you know, they're trying to help, but you're just stuck in meetings and not doing anything. So you have to make that process more gradual. So we basically run as a standalone product and try to limit the things that are gonna slow us down.
So where are you now then? What's happening now? It's been six months. You know, and I think you get through the initial, like 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 know, we've had a hundred people at our company, and now we're part of a two thousand 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. You know, so I report into 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 we took all of our internal hiring needs and we sort of like said, hey, do you have any great people that at Atlassian that wanna work on Trello?
And we've got twelve amazing people like that. Yeah. And the best part about that was those people are super experienced, and when they came over the difference is when you hire someone, it takes them a little time to ramp. These people are like checking in code like day one, you know, like fixing bugs day one.
Wow. So that was super helpful. And there's just a lot of resources there and a commitment to invest in r and d and build an amazing product that, you know, just basically helping us move faster than we were before. Yeah. Sometimes when acquisitions happen, product sits on the shelf and then it'll kind of just sort of stay status, doesn't it?
Yeah. That's kind of disappointing sometimes. I think it's like, what what was the intention of the acquire? Did they acquire to sort of just take that out of the you know, are they but for us, there's a lot of investment happening in our group, and the the the the the what's the term for this?
It's like the the the Atlassian's 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.
Do you know, obviously you seem pretty happy and you're you know, you've got a fantastic exit and you're obviously still excited about the product itself. Do you feel obviously, it's a little bit way in the future, but do feel you've got a few more acts to go?
Oh, More startups in here? Oh, more startups? I got more here's the thing. When there are so many features and things that we have to do at Trello. Like the list and the the board that we have is just like got a lot cards Trello's Trello board like?
It's got a lot of cards on it. I think there's a little warning that says like, you have more than five hundred cards on this board. Please archive some of those cards. No, but there's so many things that we have to do in the product and that I haven't even thought about that yet.
That's for another time. Yeah. You've got a large Trello board to deal with Yeah. At the moment. Yeah. That Trello. Well, I think we've we've heard so much about you. It's fantastic to meet you in person and to hear about your success. Well, for having me.
