Trello’s Journey From Idea to 20M Users and $425M Exit with Michael Pryor, Trello

Everyone says listen to your customers. It's a little trite. Who else are you going to listen to? When people would come to us with a feature request, they were telling us something they had seen before and our trick was to build something that people love because it wasn't like anything that they had used before. So if all we did was listen to the feature requests that they asked for, we would just end up with the same tools that were already out there that they had already seen. I need some traction. You need some traction. Let's get some traction.

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Users because I got it on a.

Beta trial and I loved their product. So I had to invite Michael to talk about how to build products that everyone loves.

No pressure apparently. No pressure.

The most sought after exporter that's the.

First time I've heard that one. Now I feel nervous because now I have to live up to that. You can do it. We'll see. Thanks for being here. How many of you here in the audience use Trello? Whoa. All right.

Decent amount. Maybe half.

That's about half. How many of you pay for it? That's exactly what I expected to hear. These atlassian guys paid 425 million for it, so they paid for most of you for the time being, I think. But I was going to ask you, what does Trello do? But I think everybody in the audience knows. Yeah.

Maybe just to give the 2 second. If you've ever used sticky notes before, written down some notes, put them on the wall to organize your thoughts. Trello is basically a digital version of that where you can make a board, invite a bunch of people to it, put your sticky notes up there so you can organize what you're working on.

That seems easy enough. You launched in 2011, so you've been around for a while.

Yep.

Talk to me a little bit about what that launch was like, because it was a bit of a different experience. And boss, the company I work for.

As well, we launched at TechCrunch Disrupt. It was a competition thing. It was called Startup Battlefield. We got to the fine. We didn't win.

Sorry about that.

But the company that won does not exist anymore, so we don't talk about the company anymore. I think coming in second, the conference was great for us. A huge spike in signups, and I think it took probably a couple years before every day was a TechCrunch day. It took a while for that. We launched in 2011 and it was a spinoff of another company that my co founder, Joel Spolsky, and I started back in 2000. Even five years is a long time in the tech world, but in some ways it seems like, oh, look, you made this product and it's been super successful. I have 22 million people sign up to use it. How did that happen so quickly? And it's like it didn't happen quickly. It took a decade to get to the point where we were at TechCrunch, learning lessons along the way, making a lot of mistakes, a lot of luck, a lot of privilege. Just getting there and being in a position where we were able to do because of our. Where we grew up and our background, our history and all those sorts of things. We got to TechCrunch Disrupt, launched it, and that gave us a Kickstarter and had a lot of people show up and use it and eventually enough people to tell other people. And that's how we've grown ever since. So we got those 22 million signups all through. Word of mouth.

Took a while, though.

Yeah.

Where did the original idea actually come from? Because it seems like it's a really simple idea, but nobody was really doing it at the time.

So internally at the company, we tried different projects every once in a while. We called them. The company's called Fog Creek Software. And we did these things we called Creek weeks, like Google's 20% time, where you go and you just do a project. At the time, my co founder Joel had this idea and he was a little bit frustrated because people were very busy at work, but we couldn't really tell what people were working on. So he's like, all right, I got it. So everyone will have a to do list. Just one. They just have one list and it only has five slots in it. So that was. Let's be real about what you're really working on. And actually he said, two things you're working on, two things you're going to work on next, and one thing you're never going to do. So you can just see, if you show up at my door and you ask me to do this thing, it's in my Will not do slot, in my to do list. And everyone just has one list. And then you go to a page and everyone in the company, you can see all their lists. You can basically scan across the company and see what everyone's doing. And he said, we'll call it five Things or. And I was like, this is the dumbest idea ever. I just don't see how people. Why anyone would do this. There's tons of to do list apps. There's, you know, and we just started playing with the idea. We were actually building a bug tracking tool at the time that competed with Jira. And we would go into our devs offices and they would have sticky notes on their walls to keep track of stuff. And we're like, why aren't you putting us in the bug tracker? Like, why are you putting this on the wall? And there was something about the level of perspective that they needed something just, I don't know, like this deep dive of a database with thousands of things in it versus, I just need my overview. What am I? What's going on? And so those ideas kind of combined. And obviously there are a bunch of developer tools that look like Trello this, Kanban tools, this way of building software and the agile methodology, and those sorts of things. But we decided, hey, we could take the good things about this that are applicable to everyone and try to launch a product that is much more horizontal. And so that's where the idea came from. And I think we got on stage at TechCrunch Disrupt and we said we're going to get 100 million people to use this product. Which just seemed ridiculous at the time.

It's still not there yet.

Yeah, I know. It's still got a ways to go. There's a lot of work between here and there, but definitely seems a lot closer than it did that day for sure.

Now when you launch, you were talking about how this really picks up from a methodology that developers use very often. Was that your target audience though when you started or did you feel like you could do? Were those the first users though?

We knew from the very first day when we said 100 million people, there's not 100 million developers. So like the idea was to set the scope for what this product could be. And we really did want it to be a universal tool used by everyone from people in sales and marketing and hr and obviously who wouldn't want everyone to use their tool. But I think when you're building a very horizontal tool instead of focusing on niche, you make different trade offs and different decisions. Now you're right that most of the people that knew about us knew us from Fog Creek. They were either customers, they were developers. We also had co created this company called Stack Overflow, which if you're a developer, you know what Stack Overflow is. It's a Q and A site for devs. And so that was most of the people that saw the app in the very beginning. That was a weird dilemma for us because what would happen was people would show up and they would start asking for feature requests for things that they had seen before and things that were very appropriate to their work and who they were in their role. And we started to ignore it a little bit. And everyone says listen to your customers. It's a little trite. Who else are you going to listen to? When people would come to us with a feature request, they were telling us something they had seen before. And our trick was to build something that people loved because it wasn't like anything that they had used before. So if all we did was listen to the feature requests that they asked for, we would just end up with the same tools that were already out there that they had already seen. And so what I told people to do and what we learned to do was to listen to the pain that people were having. So the first thing they do is, here's how to solve my pain. All you have to do is add this feature. And in fact, in that day, things like user voice were really popular. This crowdsource, go tell us what you want and then vote it up. And we even had a Trello board in the early days where we had people putting their feature requests and voting them up and down.

Did you just move it up and down?

But it's like a weird contract because you're basically saying, hey, tell us what you want to build. Tell us what you want. And then if you don't do that, it looks like you're ignoring your users. And I think that the trick is you had to ask them what the pain was that they were having, and think about that pain from the perspective of other people that are not developers. The trick with building a horizontal app is you can't put a very specific feature in there that solves one person's problem. You have to build the feature that's going to solve most everyone's problem. I'll give you an example. There's this concept in Kanban called Swimlane. So you see, Trello is the sticky notes are organized in the columns, and sometimes they want to organize things horizontally in addition to vertically, and they call them swimlanes. And it's like this concept that I don't think necessarily people would immediately get or understand. And so it's tricky. And so we ask, what are you trying to do? And there's some visual separation that they're doing. And once you start thinking about that, you're like, okay, maybe there's other ways I can do that, that give people the building blocks to solve in that way, but also give other people a building block to solve it in a different way.

Did you take any feature requests, though? You must have gotten a lot of feedback in those early days.

So some things I think that were probably a mistake. So in the concept of Trello, we weren't trying to build a task management tool. We're trying to build a project management tool. It can certainly do that, but it does so much more. Like, people use it to keep track of the art in their house, or they're gonna go on a vacation with their friends or church group, or all these different things that if you went to the person that was trying to solve that problem, they would never go, oh, what I need is project management tool to plan my wedding. They would never. That wouldn't occur to them. So we weren't trying to build a project management tool, which meant that the concept of a card could be anything. Like a card could represent. I don't know, I'm not going to tell you what it represents. And so a lot of people are using Trello. They used it to represent tasks, which is very common. And so they wanted the ability to mark a task as done. But in this world in which you can use Trello for so many different things, having a card that is like a piece of art in your living room, like, you can't mark that as done. So how do you solve that? And that presents interesting problems.

How do you solve that? Because if you want to build such a universal tool for everybody, you run into everybody's problems.

So that example. I'll tell a story about that. So we would have that feature request come up a lot. People would say, let me mark a card as done. Let me mark as card is done. And we would say, why don't you archive it? Why don't you put in a list called Done? We had all these different suggestions for them. And somehow that pain was still there. That kept coming back with that feature suggestion. As we dug into it more and more, what we discovered was there's a way to add a due date on a card. And if the due date passes, when you look at the board, there's a little red bell that appears on the front of the card to let you know, hey, this due date passed. And we realized that was annoying people, because if you had a card, you had a due date, the date's passed. You don't want to archive the card. You're like, why is Trello yelling at me? We're causing anxiety in our users. And that's basically what you don't want to do. You want things to be very natural. You want them to love your product. And that was the pain. The pain was this red in their face that was saying, you didn't do this thing. And they're like, I did do it. And so then they were like, I hate you, Trello. And so they would say, the feature request, like, mark this card is done. And we're thinking, well, cards are not necessarily tasks. How do we introduce this without sort of pigeonholing Trello into this thing? And we had a lot of different ideas, but once we discovered that it was really just this red badge on the front of the card that was annoying people, you could focus on just that piece. And what we ended up doing was if you add a due date on the back of the card, there's A little checkbox. You just check it and it won't show you that red badge anymore. And basically the request for marking cards, as done, disappeared. Even though we didn't add that feature to the app, we added something much smaller and more focused that everyone just kind of gets and understands. And then the pain went away. Sure.

Now, I looked at your launch presentation from 2011, and it struck me how similar Trello looks today to how it looked a few years ago. That means you must have said no to a lot of things. And that's hard to do, I think, especially in the tech world, where everybody wants to add more features and do more things and be something for everybody or go down into some niche.

The problem is every time you're adding features, you're creating a more complex system. And that's what developers do all day long. You think of an abstraction and you create code around it, and then you present it to a person. And so devs are really good at doing that. But when you have that system and people come into it, then you have to explain to them what it does. So, for example, if you use Salesforce, you've got to come up to speed on what a lead is, what a contact is. There's like all these concepts in there, and contact can become a lead, but a lead cannot become. I don't know, there's all these rules around it.

Thankfully, I don't have to use Salesforce well.

But once you understand that, Salesforce becomes a very powerful tool to you as a salesperson. And because Salesforce, the app, knows about the data that you've put into it, it can tell you all these amazing things. Like, it can be like, hey, your pipeline's too short. You're going to miss your quota next month. In Trello, we're trying to do something more akin to what Excel did, which was, we're going to give you some building blocks to build something that's going to solve the problem the way that you see the problem. I'm not coming into a very specific role and saying, hey, you're a salesperson. These are the tools that you need. These are the objects in your world. And you can add labels to cards, and that can be whatever you want. You can put somebody's face on a card, it could be whatever you want. I don't have a preconceived notion of how you work. And so Trello is allowing you to build that system as you go, in the same way that if you put data into a spreadsheet, you start to tell Excel, you're like, this is money and this column represents this. And even when you go to add a chart in Excel, you kind of have to tell it what you want it to chart. It doesn't know. Whereas, like in Salesforce, it could be like, here's your bookings next month. Building that horizontal tool where you don't know exactly what people are going to do with it, you have to think about giving them really easy building blocks. And it's tricky because then it means that there's a little bit of work that they have to do, but it also means that you can be applied to so many different situations.

Now, we just noticed that a lot of people use Trello but don't pay for it just yet. How did you start monetizing? And how did you improve that process over time? Or maybe you didn't because they're not paying.

Yeah, it goes back to what we said at TechCrunch that day, which was. And we didn't make this up, but we get 100 million people to use the app. You get 1% of them to pay you $100 a year. Great $100 million business. And those sorts of numbers were just guideposts. They weren't specific goals. But to say that there will be some people that get a lot of value out of Trello and use it to run their organization or their company or their team, and as they get deeper into that, they'll have more advanced needs. And we still have a lot of ideas around how we're going to do this, but we're doing some of it now, we're going to do more later. But we can provide that additional functionality and let people become paying customers because we expose that to them so we can deliver more value. We certainly give away a lot of value right now, but that's partially also why people love it. Now, there's two ways people. Or there might be more, but there's two ways I can think of that people pay us. One is they give us money, and two is they love Trello so much that they evangelize it for us and tell other people how they use Trello to solve their problems. And a world which you don't spend a dime on advertising up until today. Now we are previously. So it's very important that your users are fans and that they tell other people how they use the product, especially in a horizontal tool, because they. If we went out there to pitch an ad, you could use Trello to do wedding planning. But if we make an ad, that's about wedding planning, it's, you're already married. Like, it's not going to really resonate. So in this world in which you can use it to do so many things, the way that most people will experience Trello is because someone else is already using it and then they invite them into their problem or their plan.

How do you get people to love you, though? Because most people do not love their task manager, I think. Unless you do.

Yeah, that's a valid point. I think there's a couple specific things I'll say so. One is that the brand and the voice of the product are engaging and fun. Like, I'm wearing our little mascot, Taco the Husky. There's something about the way that we speak to people and the fact that it's not going to be this enterprise tool. You can use it for all different facets of your life. The freemium helps that too, because then people can just get into it and start. But fun is interesting because it's not something you can just like sprinkle on. You can't come to the board meeting and your VCs are like, you need more fun in your product. And you go back to the designers and you're like, add some fun. And then every time you archive a card, a unicorn like flies across the screen and people are just like, ugh.

That's how we got stickers in every app.

We have stickers in trial. But I think it's more about, like, allowing the personality of the people to shine through. You're gonna have people on your team that are super creative and you need to create a space so that those people can do the things that they do. So for example, when you log into Trello, the sample login text changes. It's like some pop culture references that are jokes to the people that get it to the people that don't get it. It just still tells the story of. Here's where you put your email. Trello is available in 21 languages. So when we go to those other countries, we try to do something similar in those countries. But it wasn' I said or had a product said, hey, we should do this thing. It was because we just had a really creative developer and he felt the freedom to be able to do something fun like that and then did it in the product or even this mascot. Like, one of our designers just was really a big fan of our co founder's real life dog and created a mascot for it. And so I think that stems from the culture and then make space for the people to do that the other thing I think more actionable. When I talked before about causing pain to people, like expecting something to happen and your app's doing the reverse. It's like that what you want to do is preempt what they expect to happen. So in Trello, if you hover over a card and you copy like Control C or Apple C and then you paste it, it'll paste it, paste another card in Trello and if you go to another app, it'll paste a link to the card and it's like a simple little thing. But maybe people wouldn't expect that to happen, but then they're like, oh yeah, of course it works like take a list of items somewhere else in another Word doc or something and you paste it in to a card. Trello would be like, hey, did you want one card or did you want 10 cards? It just knows that you just paste it in a list. So there are little things throughout the app that are. Oh yeah. That made. That made it a little bit easier to. And I kind of didn't necessarily expect a web application to do that, but then it did and it was really nice. It's very human, right. I feel like trying to make software that's very human now is really important because it's really easy to make software now. It used to be that if you could build a database backed website like you were golden, right? Yeah. But nowadays it's awesome because now there's all these frameworks and ways to build these apps much quicker, but it raises the bar much higher. So Meeker's report yesterday was talking about designers to developer ratios. And actually Atlassian was one of the examples where you can see the shift where there's more designers per developer now at most of these companies. And you look at Snapchat and the way that that work and it's all about the expectation of the user, which sometimes can make it difficult. If you're not familiar with Snapchat, you're like, what the heck is going on?

How do I do anything? You were talking about the word of mouth aspect of growing. At some point you must have hired salespeople as well to sell into the enterprise maybe. And the bigger companies, the ones that.

Do actually pay, or because we're freemium, our enterprise sales model is we're not actually selling the tool to the company, we're just going to a company where there's already thousands of people using Trello and saying, and it's actually like the end users, like all the people here might be using it and Be like, I don't pay for it. But actually their company might. They might not know. So in that world, they might get a lot of value out of Trello. The IT person says, what, there's 1,000 people and they're not using two FA and SSO. And if somebody leaves the company, I can't get access to their data. And you're like, oh, we have that, that's in the enterprise package. So do you care about security?

Nobody does.

So. But it's kind of interesting because that person is not necessarily a Trello user. We're not actually selling the app itself. We're not selling like, hey, you should use Trello. It'll make your company more, like, productive or more organized. That's already happened. And so we're just coming in, we're saying, yep, we'll work with you, we'll tell you the things that are relevant to you as an IT manager or the cio, and then we'll go through the procurement and the contract negotiations and all that kind of stuff.

Now you've got millions of users who love you. And then in January, Atlassian calls me up and says, hey, we're buying Trello for a good amount of money, especially because you haven't raised all that much. Why did you sell?

We didn't need to, right? Like, we're doing great. We had a lot of VC interests. I was actually trying to think about another raise at that time. I was talking to VCs and Mike Cannon Brooks, the co founder of Atlassian, sent me an email and said, hey, I'm going to be in New York. Do you want to sit down and have lunch? I kind of knew what we were having lunch. Like, I kind of figured out, okay, sure, I had nothing to lose. Like, I was ready to do this round, but I thought, hey, I'll listen and see what he has to say.

You must have been quite aware of Atlassian.

Obviously, I've been competing with them for a long time. Very aware of them. And so Mike and I sat down and we had lunch. Later I found out he had flown from Sydney to New York to have lunch and then flew back. I didn't know that at the time. So we had this hour and a.

Half that would have giveaway, I think, if you'd known that.

And I'm thinking, I haven't been through this before. I don't know how this works. This wasn't corp Dev showing up like, hey, let's do a partnership. And then later, something like that. This was like, founder, okay, great, I'm thinking, is he gonna slide a piece of paper across the table and I'm gonna look at it. He's like, I don't know, what should I order? What's good at this place? And so we ordered some food and he's tell me about what are your goals? What do you want to do? And so I start telling this story about what we want Trello to be and this hundred million people. HE laughs and I'm assuming he's laughing at said 100 million people and he thinks that's ridiculous. And I'm a little bit, well. And he's no, it's funny because we internally had this big, hairy, audacious goal to motivate the company for a very long time. We wanted to get, I think it was 60,000 customers and they were always moving towards that goal. And he's. Then we passed it and then what do you do? You got to come up with a new goal. A very audacious goal. And we spent a lot of time thinking about this and we came up with, we want 100 million people to use our products. And I'm like, oh, that's interesting. It was a little thing. But I was like, yeah. And then we started talking more and we talking. He asked me all these questions about the culture and the people and it was just one of those moments where I was like, he started. Him and Scott started a company at the same time that Joel and I started our company. We've been through a lot of the same. The dot com bust, the 2008, like there was no stripe or braintree back then. We both wrote our own billing code. There was a lot of shared experience there and a lot of shared lessons. When I thought about that 100 million goal and I'm sitting at the table with somebody that I really would enjoy working with and I think that can help us get there faster. And there was a good offer as well. Seemed like a no brainer to me.

No doubt you immediately knew you were going to take it.

If it was a typical corp dev experience where like a big company came and showed up, it would have been a totally different scenario. And it's certainly like the offer was a good offer, but I think the focus on the people and the mission of the product was really important to me. It's like that we were speaking the same language.

So you must have had a few offers before this one that you turned down the Microsoft, Google, but this one was the one. Now after a few months, does it feel like it was a marriage Made in heaven.

It doesn't feel that different. Certainly working at a 2000 person company is completely different experience than working at 100 person company. There's that, I'm not going to say like nothing's different, you have a lot more people. But in the same way that's actually really good for us. We would spend a lot of time thinking about we have our one year plan or three year plan or five year plan. When you think about that landscape and all those other companies out there like Facebook and Google, Microsoft, we're like, how are we going to compete with them? Because eventually if we keep going on this path and we get bigger and bigger, we will have to compete with them. And it's oh, are we going to build another app? And we snapped our fingers like overnight we became a 2000 person company that has a lot of really smart people building other products and now we're instantly competing with those other companies. So it was like I was almost like a fast forward, like eventually we wanted to get there anyway and so instead of spending all the time and energy like doing that, it was like, okay, now we can immediately compete with them and with really smart people that are doing many different things across all kinds of different products and areas.

What's next for Trello?

100 million people. We still got, you know, we got our ways to go there. I think this year I think more about people that really get into it. They've got a lot of boards and they're trying to get perspective over multiple boards and they're really getting more use out of it. I think we're going to spend some more time thinking about those people.

I still feel bad that you didn't win the battlefield.

I know it's a badge of honor now. If you come in second and start a battlefield, it seems like that's the.

Better way to go now. Yeah. And I wasn't working there at the time, so actually I don't feel that sorry for you. Thank you very much.

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