How a Simple Idea Turned Into a Product Loved By Millions of Users - with Michael Pryor

How a Simple Idea Turned Into a Product Loved By Millions of Users – with Michael Pryor [032]

How a Simple Idea Turned Into a Product Loved By Millions of Users

Michael Pryor is the CEO of Trello, a free app that makes working on group projects as easy as using sticky notes on a whiteboard. He is also the co-founder and President of Fog Creek Software, the makers of products such as FogBugz and Kiln. To date, Trello has raised over $10M in funding and is used by millions of people and companies of all kinds and sizes including Google, Adobe, and The New York Times.


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Host: Omer Khan

Guest: Michael Pryor

This is the ConversionAid podcast, Episode 32. Welcome to the ConversionAid podcast, where we help software entrepreneurs to take their business to the next level. Each week we interview proven industry experts who share their strategies and insights to help you create software that sells. Here is your host, Omer Khan.

Omer: Hey everyone, welcome to the ConversionAid podcast. I am your host Omer Khan and this is the podcast where software entrepreneurs and companies who want to grow their business to the next level and create software that sells. Today's interview is with Michael Pryor. Michael is the CEO of Trello, a free app that makes working on group projects just as easy as using sticky notes on a whiteboard. He is also the co-founder and President of Fog Creek software, the makers of products such as FogBugz and Kiln. Today, Trello has raised over 10 million dollars in funding and is used by millions of people and companies of all kinds and sizes, including Google, Adobe, and the New York Times. Michael, welcome to the show.

Michael: Hi Omer, thanks for having me on.

Omer: Now before we talk about Fog Creek and Trello, tell our audience just a little bit about yourself. Who is Michael when he is not working?

Michael: So I am a recent father of a 3-month-old; I also have a 2-year-old.

Omer: Congratulations!

Michael: Thank you. Not getting much sleep! I live in Brooklyn, right across the Brooklyn Bridge; started a software company 15 years ago with my co-founder Joel Spolsky and that is what I do every day.

Omer: Awesome! Now before we get into more details, we'd like to kick things off with a success quote, to better understand what drives and motivates our guests. What is one of your favorite quotes?

Michael: So this is more of a principle that I picked and it's…everyone knows this is sort of hard to kind of try, but it's really important. When I tell you the story about Trello, you'll see why. I mean, it is the ‘KISS' principle which is “Keep It Simple Stupid!” or “Keep It Simple and Straightforward” – some people like…

Omer: Yeah, depending on who you are talking to, right?

Michael: Yeah. [Laughter]

Omer: Okay. Let us start by giving the listeners a better understanding of Trello. I explained a little bit about the product and I am a user myself, but tell the audience a little bit about who your target customers are and what are the pain-points you are trying to solve?

Michael: So one of the things that we set out to do when we first created Trello was to create a course on our tool,  that pretty much anyone could use. And the goal of this tool was to give structure to the projects that you have, whether it is in your personal life or work and it all started from our experience as software developers. We, my co-founder Joel Spolsky and I started Fog Creek 15 years ago. We hired a bunch of programmers to do smart things. We ended up building a bunch of developer tools that are pretty popular, and that was basically our target audience. He has a blog that a bunch of people read, and we had basically been building things for developers for a decade. And we saw a bunch of principles that a developer…, for using that could be applicable to basically anyone in any areas of life and we tried to create something like Trello that was much more flexible, to be used in many different areas, instead of just for developers who are making software.

Omer: Awesome! So we'll talk a little bit about that in a minute. Now, before we do that, tell me a little bit about what you were doing before you started Fog Creek with Joel?

Michael: So it was…, actually I only worked for about a year and a half before we started Fog Creek, so I met Joel at a company called “Juno” which was, back in the heyday, the internet in 2000s was a company that was trying to get free email to people, competing with AOL at the time, you know. You had to pay a monthly fee to dial up to AOL and their idea was let people do it for free and then show them advertising [supported]. I am not even sure if that company still exists, but Joel and I worked there for about a year and then everything started crashing in the market and we just basically set off on our own and started to…start a software company. At the time, there wasn't a place in New York City to work at, as developers, that was a pure software company. Like, there were plenty of places to work as a developer, but you were either working at a finance company or insurance company; you weren't building end product that the company was selling. You were supporting what they were doing. Now, you know, 15 years later, there is Facebook, Google, as tons of startups in New York, the scene is totally changed, but at the time, what we wanted to build was a place where developers wanted to work. So we wanted to focus on people like us and build a company that people like us would want to work at.

Omer: What was the first product that you guys decided to build?

Michael: It was a Content Management System called “CityDesk' and so at the time, a big problem that people had was when they were trying to…you know, the things, the tools that existed at the time like TypePad, was a bunch of para-scripts essentially. If you want to install that, you had to show access to your web server in order to install it and basically that meant that not that many people could do it. So we thought, “Hey, let's build a desktop app that does all the content management stuff on your computer and then publishes those HTML files up to the server.” At the same time, I think all of the CMS creators were realizing this as well and so that's why they ended up with mostly all hosted solutions and basically remove their problem. So that tool worked for a couple of years, but then ended up not being a huge success. And in the background, we actually had some code that we had sitting around that we were using for bug tracking, while we were creating this program. And we decided, “Hey, let's put it together and sell it and see what happens,” and that ended up being a huge success for us, which was FogBugz and basically being the cash-cow for the company for the next 15 years. So sort of like a serendipitous thing, you know. We basically were pouring all our efforts into CityDesk and it was this thing that we just did on the side, that ended up being the most successful. And actually along the way, we've probably over the years have done 13 different products. Some of them you've heard about like Trello, Stack Overflow, FogBugz, Kiln, but a bunch just sort of faded off into the distance like we…Joel's blog got a lot of readers and one of the things that we did was create a job board attached to his blog, where programmers could get work and that was pretty successful, so we decided, “Hey, let's do that for Indian programmers, and so, make a place for job postings in India,” and I think we made Rs 25 and that was it! No one went to it, no one saw it. It just wasn't used. We made a movie once about our Interns and sold that as a DVD.

Omer: Wow!

Michael: Done a bunch of different projects.

Omer: And so what's been sort of the driving philosophy for you guys? Was it just because both you and Joel just, you know, have a ton of ideas and always sort of driven to pursue them or did you sort of start off the company thinking, you know, “We're going to be sort of may be incubator for these new products”?

Michael: Well, I think when we started…I mean, you know, the goal of the company was to make a place where great developers want to work, so you know, the idea was that we get smart people working with us and then we see what happens. Like we are not going to pigeon-hole ourselves into one product at the time. We'll just do things that would finally make sense and seen to be exciting, so you know, at any point in time, what we are working on now might not be what we were working on a couple of years from now. And you know, over the course of the years, some of the things have spun off under their own companies; some of the things we've sold and some of them we're still working on. Like Stack Overflow, which became Stack Exchange, the company, a huge network of Q&A sites, you know, came out of Fog Creek in conjunction with Jeff Atwood, who is a big programmer, blogger, like Joel and Joel and him brought their audience together and then Trello, which we recently, which we actually self-funded at FogCreek for a couple of years and then recently took VC and spun it off into it's own company.

Omer: So what was the reason for spinning that off as, you know, why not just keep it like you've FogBugz, within the FogCreek sort of family?

Michael: Our goal with Trello basically…we're trying to get a hundred million people using Trello and have 1% of them pay us a 100$ a year, so that's like the sort of size of the market that we are going after. We want so many people getting value out of Trello and the people that are getting the most value, they pay us a little bit of money and then that's a successful business. But if you start from that, those numbers, sort of the magnitude is important there, not the specific numbers, but you realize that it has to be a total horizontal tool that anybody can use and when we first created Trello, you know, we thought that's what we were building and after a couple of years, we saw that the traction was there and that it was going in the right direction and we decided to basically, you know, go full speed. And it made sense. We had a lot of people contacting us, wanting to invest. There was a lot of interest; we didn't really even have to do the typical, like go out and pitch it. There were already people that were inbound interest and we decided it just made sense; we had something successful, but to really grow it, we're going to need to invest a lot more money than FogCreek is able to invest.

Omer: So can you tell me a little bit more about where the idea for Trello came from?

Michael: So you know, going back to how we did a bunch of different projects over the year, we were at a point in the company where we wanted to experiment a little bit and I think we separated that into a couple of teams and tried to build 4 different products, just to see, you know, what happened and whether any of them are interesting. And the product that one of the teams was building was an idea that Joel had which is called “Five Things” and the idea for Five Things was, you'd only…it was a list basically that had five slots. Two things that you're working on now, one that you are currently working on and one that you can work on in case that one blocks and then two things that you're going to work on next and then the fifth thing was something you would just never work on. And the motivation for that was just that we saw, you know, the way businesses were working, the way software development was working and this SaaS model, really seen often and it was just changing the way people work, where it was like, they wanted to just ship and ship fast and that was…if you had this huge backlog of items that you had to worry about, it wasn't really helpful because two weeks from now, your product could be completely different. So this was more of accepting, like you can only concentrate on a couple of things at once, so this tool actually forced you to only concentrate on those things and what happened was, that idea, the Five Things sort of morphed into something different when we…it kind of, we went around and we were looking at software development teams and what they were doing, and when you go into one of these, you know, open plan offices, we are all sitting around, and you would see these whiteboards, where they had posted colored posted notes on the whiteboard. And they were moving them around to track all the different things they were about to ship, whether they were shipping, whether they were tested, what they want to build next and they basically had this really easy visual tool to show their progress essentially on what they were building. And we realized that, you know, that, coupled with this idea that you don't want to give people the ability to create an enlist backlog of items to work on, because that just sort of slows…I mean, look at how most people use their email inboxes, right? They are upset because there is a thousand messages in there, and they are like, “I am never going to get through this.” Like, it is something about the way that we work or we're afraid to just let go of things and accept that we can only work on a couple of things at once. So it sort of married those two ideas together and that's where the initial version of Trello came from.

Omer: Got it. Okay, so you've got this idea, you know…so before we get into that, so do you guys, have you been doing this regularly, where you sort of get teams together and just go and pursue these ideas to see if something will stick? Is this kind of like a culture thing there?

Michael: Yeah. I mean, we don't have like a set schedule for it, but we call them ‘Creek Weeks” at FogCreek, it's called a ‘Creek Week” because we like to take off and sometimes they are trying to innovate in a way that we are just experimenting, something outside of what we have done before and sometimes they are actually just a moment to be protected by the other people on your team, so that you can focus on something that you haven't had any chance to work on. And so, you know, back to the idea that we have smart people, they have lots of ideas. Joel used to actually keep like a text file on his desktop that had all his ideas in it and it just kept getting longer and longer and longer. But you know, yeah, we have done a bunch of things and we don't have a formal system for it, but it is something that is instilled in the culture and then we try to keep doing.

Omer: And then, how do you guys validate these ideas? I mean, from my experience, you know, I have worked with developers who will come up with great ideas for products, but it doesn't necessarily mean a translates into a business or a commercial success.

Michael: Yeah, I mean, I think we are not actually that great at figuring out how to do that…like we had a tool. There is this tool called ‘JSFiddle' that lets you put java script up and test it on a website and we've built something like that for CSS and we thought, you know, people could basically point their…they could host their CSS on our servers and then it will allow them to add it in a WYSIWYG way through a web browser and they would get all the benefits of, you know, being on a CDN and able to edit these CSS files quickly and it was a cool idea, but it just didn't catch on. We had a bunch of people using it, and at some point, e just had to pull the cord on it. You know I told you earlier we had made a movie about our Interns and that was a huge success at the time, and then we went and basically spent a couple of months building a whole series of movies. It was 5 different movies about the process of making software and we priced it like, I think it was $2500, so this was kind of like a different type of product. It wasn't a $20 DVD and you know, when we went to sell it, what we found that there wasn't a really huge demand for that. Another example where we didn't quite, you know, understand what the ramifications would be was, when we first built our code review tool, Kiln. We only explored Mercurial because at the time, Mercurial and Git were kind of competing to see which one was the winner, more really like Mercurial and then at some point we said, “You know what? Git's kind of winning. We've to get on board with this. Let's support Git.” And we thought, “Hey, what if we allow people to use either Git or Mercurial on the same repository,” which nobody does. And we actually spent a lot of time making that work and it turns out that no one does that, so there wasn't a lot of demand for it and it created a lot of complexity in our product on the backend. So you know, some of these things, we just don't find out till later and we're getting better at sort of testing these ideas and figuring out what's working, so you don't have to invest all your time in them first, but I think it is just a learning process.

Omer: So you guys have been building software for developers for well over a decade and then with Trello, as you said, you know, you focused on a horizontal tool which could be used by anyone. So what did you do differently to go and market that product and acquire customers who were developers?

Michael: So one… we had a couple…there were some simple rules like ‘Keep it Simple' and what I referred to earlier, we had some simple rules that we started with, before we made the product, that we hoped would actually make it organically, you know, spread organically essentially. So one of the ideas was that we were going to only use the latest technology, so “Don't build anything that's going to work for an old browser” essentially. That was just a rule that we had. What you just said, one of the rules was “Don't build a developer tool.” So we knew that our early audience was going to be mostly technical people and that the kinds of features that they would ask for would sort of steer us down that road and since we knew from the beginning that we wanted to build a consumer product that anyone's mom could use, they just get it immediately, we were able to sort of accept that feedback, but understand that that's not what we were building. You know, other thing was we had to work pretty much on every device, like your mobile, iPad, the iPhone, Android, and it had to be real time. So if somebody changed something on a Trello board from their computer, it had to immediately update on your computer, no matter where you were, so that you retain that sense of you are all looking at one document, just like it was a big white board in your shared work space.

Omer: Got it, okay. So there is no shortage of project management tools out there. Did you guys spend much time or energy looking at what was already on the market and how you could differentiate or were you very clear about this, sort of the vision for this product and sort of focus mostly on that?

Michael: I think that, you know, you called it a project management app which is, a lot of people call it that or they might call it ‘To Do List'; they might call ‘Trello To Do List' because there is some…you are trying to describe what Trello is, and I think actually what we are trying to build is something that doesn't…there is not a name for it, because if you think of our project management that implies a certain type of tool, I think it basically… If you were, for example, going to plan, you know, get your family together to coordinate who's going to buy gifts for your kids, like your mom and your uncle and you don't want them buying the same gifts and you know, no one's going to go online and search for a project management tools to solve their problem. But a lot of people kind of feel frustrated and don't feel like they have a lot of organization around that issue, and we wanted to solve that problem. I think that's actually one of our challenges, because essentially we are trying to build a tool that people don't know what it is called. There is not a term for this specific thing. You can use Trello as a project management tool, but you can also use it as an applicant tracking system or a CRM or you know, a bug tracker. We see a lot of people doing those things, but the flexibility that we've built in our product is sort of…the product has to stay really simple for people to be able to use it in all these different ways, but that also means that it's hard for people to get, you know, that kind of level of detail that they might need, when they actually have, for example, a thousand applicants applying to their company every day; then Trello is not going to work anymore. But it's going to work for, “Oh, you are doing the kitchen remodel in your house and you've to coordinate with your contractor.” So you know, I think trying to figure out how we communicate that to people, that we have this solution for a problem they feel, but there is no word to describe exactly what it is, I think that's one of the challenges that we have to figure out, how to do in our marketing. But you know, it actually is happening organically; we saw it happen organically which we didn't even do anything to help, but we would see people writing blog post of how they were using Trello and they would describe all these different use cases. They would just…you know, somebody that was a marketing person would write how they were doing marketing with Trello or somebody that was, you know, an editor at a newspaper would write about how they were using Trello or a recruiter would write about how they were using Trello, but they were basically telling people, “You can use this tool to do this one thing,” and they were speaking to their specific audience and then it would just basically spread like that, and we are trying to figure out now how to help people do more of that, how can we do more of that ourselves.

Omer: So what is the…I know you said it was sort of a challenge for you guys, but what is the best way to sort of position Trello in a way that people can understand it easily, right? Because even to me, I completely get that it's not a sort of a formal project management tool and I think in many ways that is the beauty of the product, right? I mean, number one, whenever I show it to somebody, they get it instantly, right, and then they are like, “Wow! Oh my God! It's like, you know, I was like trying to do with whatever are the product and have a bunch of these lists, and it was really hard to kind of visually see what was going on.” And the other thing that I really like about it is the simplicity of it, right, which sometimes can be a little bit frustrating, like for example, you know, may be within a card, I may have a checklist of multiple things that I want to give different items on the checklist different due dates, right, and it doesn't let me do that, but in some ways, just being forced to think about what is the one due date that matters the most for this one card, actually kind of brings some clarity to what I am doing. So those are some of the things I love about it, but what is the best way to explain it to people?

Michael: I think it's a tool that helps you organize. Basically, if I had to give a quick sense, I mean, and this is actually, we are actually going through a brainiac exercise right now, to just to try to figure out how the best way to explain this to people, but the name actually ‘Trello' comes from the project code name, which was ‘Trellis'. And if you think of a Trellis, you kind of give structure to a plan, as it grows, and I think about people, when they have, you know, things that they are working on their life with other people and they are just feeling a little bit frazzled, you know, like, “Ah, I don't know where this project is,” or “I don't know what's going on with my florist that was planning the flowers for my wedding?” or “I've no idea if this kitchen renovation is even, if people are even there doing anything?” And it is just sort of solving that issue, where it's allowing people to communicate and show progress in some aspect of their life or their work. But that was a pretty long sentence to describe something that's really simple. You know, and we borrowed a lot from like real world metaphors, like that white board, the posted notes, and I think that's why people get it so quickly; because there is not really a huge learning curve and it's like, “Oh, you already got this.” There is like cards and you put them on your fridge or on your computer screen, you know, in a certain place, so you remember to do something, and that is what Trello ought to do and you were talking a little bit about how, you know, you had a card and your checklist on the back and you wanted to put a due date on the checklist, but you can actually put due date on the card, and one of the other…so there is, you know, Trello has a certain hierarchy to it and I see sometimes people struggle, because way they first start with Trello, they get the mentor hierarchy that they have for how they want to lay things out, like off by one, right, like if all your checklist items were cards, then you would be able to put the due dates and I think the flexibility of the system and the fact that you could just switch that card or switch that checklist to be a bunch of cards, like probably in 20 seconds, is what makes it so useful; because basically the way people…when you start, the old way when projects was done was you get hold of a bunch of people together, you write spec, there is, you know, a whole bunch of deliverables and deadlines and you are something like Microsoft project and you know, the way people work now is, “Hey, let's iterate quickly,” and the project might be totally different in two weeks than it was today and you need something that's just going to be flexible in the way…it's flexible like we are working, yeah.

Omer: Yeah. No, I think things like Microsoft projects are wholly, completely different beast of a product and in fact that, you know, like I said, for example, I actually used Trello to manage production of these podcast episodes, right? Initially, when I went out looking, people were like, “Yes, you can use ‘x'…whatever product,” and as you move to a different phase, like you move from may be somebody has, you know, agreed to come onto the show, there is some prep work or research you need to do before the interview, you know, the work flow will trigger a bunch of tasks that you can do. And on the face of it, that sounded great and I look to Trello and say, “That is a shame, if that doesn't really do that for me,” you know. I can move things around, but it doesn't really trigger a new set of tasks. But what I eventually ended up doing was creating, I guess an empty card which on it, has the full checklist that gets used through all the phases and every time I get a new guest, I just copy that card and it basically gives me everything I need behind there to make sure that I take this through from research through to publishing or scheduling the show. And again, I think the beauty of that was that it helped me to really simplify my process and to think more about what I was trying to get done, rather than how am I going to use this tool, right, which is where a lot of people get lost, right? It's like they spend more time in Microsoft project than they do sometimes managing their projects.

Michael: Right. And I think that you hit on it right there, which is that if people have, they have a process and a lot of times they just want the tool to help them with their process, they don't want to like adopt the tool's process and that's what Trello likes to do; like we actually just found out that there is…there are whole bunch of consultants out there right now who go in the organizations and talk to them about their process and help them, you know, figure out what's going on through big Fortune 100 company and then the tools that they give them to manage that process is Trello! Like it's one of the tools. so it's like, it's a really flexible way to basically take a process and make it so that other people can see what you are doing and you can figure out that you are actually making progress on this. Another use case that I really love is there is a company that uses Trello to do it's on-boarding. So they've a template board where they have all the things that a person has to do on the first day, all the people that are at the company, the things that they need to read, the accounts that they need to create and they basically just clone that board, like in the same way that you clone the card and they are signing personally the board and then there is all the things that they have to do on their first week. And then if they find out that there is something wrong with that process, they forgot something, they just go in and add in another card or they edit it or change it or sign someone different, you know. It's just a really flexible way to sort of give structure to a process.

Omer: Okay, I want to talk a little bit about FogCreek and the culture that you guys have built there, so I was looking at your ‘About' page and there were a number of things that really stood out to me, and I just wanted to read them out, just so for the audience's benefit.

“In a world of build-to-flip type of growth, venture capital field, social media startups, FogCreek was built for the long term. FogCreek was built to take ideas from a group of brilliant people and grow them into products that support future development. And then we get into sustainable business model, where FogCreek is owned by it's employees. We don't have outside investors, so we are free to do things based on long term interests of the company. We pay our bills and fund you development with the revenue from our products and we've been profitable since day one. At FogCreek, we only work on products that grow organically from ideas we have in-house and FogCreek was conceived as a Silicon Valley style tech company located in New York. We over-invested in plush offices as our head quarters. We're proud to over-offer private offices for every developer, free lunch and snacks, high end espresso, great chairs, height adjustable desks and all the 30 inch monsters you can eat, now that working remotely is just as effective as working from a single office. All of our development teams do their work fully online; that means any team member can work from just about anywhere with high-speed internet and we are happy to hire great people from anywhere in the world.”

I read that and I thought, “I want to apply for that place.” [Laughter] So, you know, what is it about the company that, you know…was this a vision you and Joel had when you said you wanted to build a software company in New York? Or how much of this has evolved over the…you've sort of figured out over the years?

Michael: No, I mean, the mantra of creating a place where the best developers want to work, you know, was basically our mission from day one. So we started FogCreek in New York. We were like, we looked around; there weren't any software companies that you could work at; we were working on the product that was actually getting shipped, like you were the important component of the organization and so we decided to start one and we knew that that the only way that we were goimg to succeed is if we got really smart people to work for us and the way to do that was to treat them well. So that is why we have private offices, we lunch together and you know, in the early days, we used to see people looking at job offers and they will be like, “No, I am trying to decide between Google and Microsoft and FogCreek” and we just thought that was…fun[Laughter] I mean, like the people are putting us, you know, at the time, we were probably like 15 people. But you know, we have a huge advantage of being in New York and being, you know, one of the only pure software companies here and then over the course of, you know, a decade and there is more Startups, there is more perks, people are treating developers right, because they realize how hard it is to hire developers and so you get to a point, you know, couple of years ago, where there is not that much difference between working at FogCreek and working at a different, you know, software company in New York. But that's when we realized, “Hey, we can work with all these great people that aren't located in New York city and try to figure out how we can work with remote people essentially.” And we had a bunch of people in New York that wanted to move, who previously would have just left, gotten a different job; then we were able to retain them and you know, the tools were getting better to work with people. I mean, we used Trello all the time to coordinate that, we used Slack to chat with people and Google Hangouts all the time, so the tools got better and I think it is still an administrative nightmare on the backend – taxes and all that kind of stuff, but we were able to basically get people that otherwise would not have worked for us. Like at Trello, we actually have one of…there is only five in the US,  that are called Google Developer Experts – GDE and we have one of them working on the Android team, and he lives in Minnesota.

Omer: Wow!

Michael: So you know, I don't think we would have been able to attract somebody…I remember back in the day actually, we had the movie I was telling you, the Interns that you have made screen-sharing product called ‘Co-Pilot' and it's basically what ‘LogMeIn' is now and it was actually, we created it almost before ‘LogMeIn' even existed, but one of the Interns that helped create, that brilliant guy just didn't want to live in New York and so we lost him. He went to go, work for Microsoft and that was about 10 years ago and now he works for a company called ‘FireBase' which is a very successful database company, but you know, now he would have been able to work for us and live wherever he wanted to live. Now it's certainly, there is a lot of challenges, working with remote people, I think like culturally it's very difficult because now, everyone is not here, you don't get all those conversations at lunch and those types of things and we are trying to figure out, you know, learn as we go on, how to keep that culture alive, even though those people aren't in the same physical space.

Omer: So let us talk about the business today. Do you guys disclose revenue?

Michael: No. FogCreek is totally private.

Omer: And profitable!

Michael: Yes. And Trello is in growth mode, so we're just focused basically right now on just getting the product; like our top two development efforts right now are localization and offline mode in mobile. So you know, we are just hiring; we have raised a bunch of money so that we can spend more money than we are making, so that's not really our number one focus at the moment.

Omer: And how many people do you have working at FogCreek and Trello?

Michael: There is about like 35 in FogCreek…or maybe 39, and there is I think just over 30 at Trello.

Omer: So why did you decide to take on the CEO role at Trello?

Michael: So I previously was working as the President for FogCreek, taking care of FogCreek and then also the CFO at Stack Exchange, because at the time, when we first spun that company off, I was just running all the operational side, you know, the accounting, the legal…all those things. As that company got bigger and bigger and bigger and we had three offices and 200 people working for the company, and it just became very obvious that we needed somebody with real finance background, to come in and get things in order. So we found somebody, hired him and I, you know, stopped my day-to-day role at Stack Exchange; still doing everything else, doing at FogCreek and that sort of freed me up and basically at that time, you know, we've had the investors who wanted to invest in Trello and we were sort of pushing them off saying, “It's okay,” like “We'll just keeping funding on our own and then we'll go on a little bit slower because we can't pump always money into it, but that's okay for us,” and it just sort of, you know, made it more clear that I actually could spend some time doing that and it probably was a good time for us to take outside investment. So all those things kind of coalesced into that moment.

Omer: Got it! So is there one thing in your business that you are most excited about right now?

Michael: So for Trello, there is…I told you about the localization and mobile offline mode, and then we have sort of a wild card project that we are working on in. It's kind of top secret. I am not even sure if we are going to ship it, but yeah, the idea is that what we see a lot of people taking Trello into a standup or like a weekly meeting or you know, even a one-on-one, where you are just meeting on a one-on-one or a team, but basically, Trello is the content of the meeting, they are using Trello just sort of look at what they were supposed to work on, you know, report progress, so it's sort of they are all meeting in person and talking and they are looking at a Trello board. Lot of times they have an Ipad or it's up on the screen or something like that and so we are trying to figure out a way to facilitate that so everyone actually doesn't have to be physically located in the same room.

Omer: Got it! Okay.

Michael: We'll see if that's interesting to people or it may just be, you know, an experiment that we end up not shipping, but I am pretty excited about it and I think it is going to actually change the way people use Trello.

Omer: Cool! Okay Michael, it's time for our lightening round. I am going to ask you a series of questions. I would just like you to answer them as quickly as you can. You ready?

Michael: Okay, sure.

Omer: What's the best piece of business advice that you've ever received?

Michael: So there was something recently that Keith Rabois said on a podcast; it's “How to Start a Startup.' Sam Altman is putting that out of Y Combinator. He said, “Measure your false positives, because if you are just measuring one thing, you are not understanding how that affects the business,” and his example was Paypal. If they had just told the fraud department to measure, you know, the lower fraud rate, they could've done that by actually calling up every customer and vetting them before they were actually able to do a transaction, but that would have been horrible to the business. So you can't just measure like, “Are we getting more trials?” because maybe those trials are actually useless.

Omer: I like that one. What book would you recommend to our audience and why?

Michael: Keeping the theme of keeping it simple, there is a book that, I don't even think it's published yet, but I just got sent it a couple of days ago. It's called ‘Simple Rules', so it's kind of coming out real soon and I have just started reading it and it’s fantastic!

Omer: Well, we are getting a lot of insider stuff here! [Laughter] What's one attribute or characteristic in your mind of a successful entrepreneur?

Michael: So if I look back on my own experience, one of the things I contributed to all the amazing things that have happened on my career is having a great co-founder! So I don't know if there is something you can, like, make happen, but it certainly contributed to my success.

Omer: Well, you can make it happen by making sure you picked the right guy, I guess!

Michael: Sure, yeah.

Omer: What's your favorite personal productivity tool or habit, apart from Trello?

Michael: I was going to say Trello…let's see, well…you know, we use Slack all the time. It's a chat program and I think having, you know, being able to communicate on the computer with the rest of your team when they are remote is immensely useful and Slack is a great tool.

Omer: If you had to start over tomorrow, how would you go about finding that next business opportunity?

Michael: I think I would look for frustrating things that I was dealing with as a business owner and try to make them better. So that is basically what we have been doing for the past 15 years, but there is a lot of things that I have dealt with recently that I am still wondering why someone hasn't created a simple way or better way to do it.

Omer: Yeah, I think that's such a huge point, that there are so many opportunities out there. You just have to look. [Laughter]

Michael: Yeah. And sometimes you just reinvent this…like how does, you know, why…there were tons of content management systems out there and now Medium comes out and everyone starts using Medium and it is just huge, you know, like why? I don't know; you know, like there is something about the way that it works and it is solving problems that look like they are already even solved can be, you know, usually successful doing that, so…

Omer: What's an interesting or fun-fact about you that most people don't know?

Michael: So I'll give you a fun-fact about Trello, that most people don't know, which was that, Joel wanted to call it ‘Five Camels'; it doesn't make any sense, but that was..I don't know why, and then we couldn't figure a name for it, because, the domain was taken and we couldn't get it, and so we had this company-wide meeting and basically spent like, you know, all day trying to pick a name and when you crowdsource a name, you come up with some, a lot of crap! The name that we agreed on was ‘Planety' and it was so bad that I went back to my office and I was like, “I am going to find a better name, better domain name that exists than Planety,” so you know, Trello could actually have been called ‘Planety.”

Omer: Love that! Okay, and finally what is one of your most important passions outside of your work?

Michael: Right now, my family, number one. My two-year old is so much fun and so being a dad is a lot of fun, but also, I am a huge saltwater fisherman and I have a 400 gallon saltwater aquarium tank in the office.

Omer: Wow! [Laughter] Awesome, great answers! Michael, it's been an absolute pleasure talking with you today. Thank you for sharing your experiences and insights and thank you for letting us get to know you a little better personally as well! Now, if folks want to find about FogCreek or Trello, they can go to : or If they want to get in touch with you, what's the best way for them to do that?

Michael: Email me: [michael AT]

Omer: Awesome! Thanks again and I wish you continued success.

Michael: Thanks Omer.

Omer: Take care. Alright. I hope you enjoyed that interview with Michael Pryor of Trello and FogCreek. You can get to the show notes for this episode by going to where you will find all the links and resources that we discussed today. If you'd like to get in touch with me, you can find me on Twitter: @omerkhan or email me at: [omer AT] And if you enjoyed this episode, then I really appreciate you taking a couple of minutes to just submit a review on iTunes. Just go to Until next time, take care. Until next time, take care.


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