Startup Founder Michael Pryor

Michael Pryor, co-founder Trello

Michael Pryor is, together with Joel Spolsky, co-founder of collaboration tool Trello. We met Michael at the Next Web Conference 2017 to talk about the journey from engineer to CEO, success, failures and worries.

Can you introduce yourself to our readers?
So I started a software company back in 2000, with my co-founder Joel Spolsky. Joel wrote a blog called ‘Joel on Software’, which was pretty famous in the tech world. We started the company to build a place for developers to work at. It wasn’t about the product, I think most people start companies based on the product; we just wanted to build a cool place for devs to work in New York City. Back in that era there wasn’t really a great place for developers to work in New York City, like you either worked in a bank or an ad agency. There was no tech scene in New York in 2000 that was all in Silicon Valley. So we started a company, we didn’t know any better. We were naive enough to think that we could. So we just did [it]. We built a couple of different products, some were good, some were bad. We made a little bit of money, kept doing that; experimenting with different products over the years, learning lessons. We built a lot of things that were the right product at the wrong time, or the right product marketed to the wrong people.

I think a lot of people have heard of Stack Overflow, which is one thing that Joel and Jeff Atwood co-created together, and Trello is obviously something that I spent most of my time on running recently. But there’s so many failures in the wake before that, that helped shape those things and even if you look at Trello for example and you’re like ‘wow, 22 million people sign up to use Trello’ and ‘they got acquired’. It seems like that just happened really quick. For one, it took 10 years of lessons learned. And then two, we’ve been working on it for six years now. I think that’s the most interesting thing. When you tell these stories in the press and you talk about them online, it seems like it’s all roses. Like you just came up with an idea that was brilliant and then… We have a list of ideas that we’re never going to get to: It’s all about the execution. It’s all about just sitting down and doing it day after day, and building the product and thinking about the future and trying to be in the spot where the future landed. Kind of preemptively trying to… Think about AirBnB for example, Brian Chesky going around and tell people that they were going to let random strangers sleep on their couch, and everyone is like ‘that’s the most ridiculous thing I’ve heard’. You might make a couple of dollars from kooky people that want to let strangers sleep on their couch, and are hard up for some cash, but that’s never going to be a big business. But CouchSurfing was a thing, and it was this niche that was never going to be mainstream. But it did go mainstream, and now it’s taken on the whole vacation rental industry and the hotel industry. That was just about imagining a future that didn’t exist today.

What inspired you to become an entrepreneur?
I think I was just too dumb to know any better. That’s why I became an entrepreneur. When I would see things I would just do them, because I figured if somebody else can do them, I can figure out how to do it. When I first got to college, I had to get a job. I delivered newspapers at like 5 am, which is like the worst college job ever, and I was in New Hampshire so it was snowing, the most awful weather. Then I quit that job and worked at the dining hall, dishwashing; the most awful job. Then I had to get help on my computer, so I went to the Computer Center. I discovered that these people were just sitting there all day helping people with their computers, getting paid probably more than I was making, I needed to get that job. So I didn’t really know that much about computers, but I went to the supervisor and I was like ‘I can do this, I’m a hard worker’ and she gave me the job. I started taking computer science classes. And one thing led to another. I liked it so much and it just became a natural thing that I gravitate toward.

Another example is that at one point my life I decided I wanted to teach myself how to go deep sea fishing. I didn’t know anything about deep sea fishing, but I was hanging out at the shore and I saw people go out on the boats and I was like ‘I can do this’. So I went out 30 miles offshore in a boat and I had a lot of harrowing close encounters with not making it back… I wouldn’t catch anything. But eventually, you learn a little bit every time, and at one point I caught a tuna! I did it!

I think that there’s a little bit of my brain that’s broken. That doesn’t understand that you shouldn’t do things, but just assumes that I can. And that’s how I got into starting a company.

Trello’s logo

Were there barriers for you to enter entrepreneurship?
Not really. At the time that we started the company, I had just moved to New York, I’d worked there for two years as a programmer. And, you come out of school as a single person, you don’t have that many expenses, and you get paid a ridiculous salary because you’re an engineer. You make way more than you need to run your life. What happened was the dot.com bubble burst, or was starting to burst, and a bunch of my friends were getting laid off. That was depressing, work wasn’t fun anymore. My friend Joel, who I worked with, found that we should start our own company, and so we did. For many, many years it felt like we were pretending. You’re like ‘I’m running a company’, like ‘I’m the CEO’ but there’s only two of you. It somehow seems really interesting and exciting, but you kind of feel like you’re faking it. But then we hired some people, and that was when it actually started to feel like a company.

Was that when you starting making revenue?
We first started with consulting, and supported the development of the software through the consulting gigs. We were building the software but were not really selling much of it. But what happened was that the dot.com bubble just totally burst, like the stock market crashed. And the first expense that most companies cut is outside consultants, because they don’t work for the company. That meant that all of our gigs just dried up, and we had these two guys that we had just hired a couple months ago. That was a really really difficult time. We told them, look, we have enough money to pay you for another month or we could spend that month trying to find more jobs. And they were like, let’s find more jobs. And we got to the end of that month, but didn’t find any jobs. We found them both jobs though, and one of them we hired back later.

We started over and we rebooted, and then you start making a $100 one day, and zero the next day, and then $204 another day. Little by little. Although it didn’t seem to go fast, if you add all those steps up, together they make a long distance. So that’s how it started.

“Work is not a means to an end, it is the journey.”

What does success look like to you personally?
The very reason that we started the company was to create a place where we wanted to work. Success was part of the journey.

We tell people, look, we want you to have the best tools that you need to get your job done. I tell everyone to buy a really good mattress because you spend a third of your life in bed, or buy a really good chair at work because you’re going to sit in it most days. Work is not a means to an end, it is the journey. So it has to be fun. You have to enjoy it. It’s this huge portion of your life, the people you work with. So when I think success, I think from the first day we started to now, there’s been ups and downs but I’ve got to work with amazing people and build cool things.

Even if you go down to the product level, one of the coolest things is when you go somewhere and you meet someone that uses your product and they’re like ‘oh I love Trello’ or ‘I love Stack Overflow’. You can’t capture how cool that is. It is the coolest thing, and I kind of feel bad for people that build like oil and gas software or something like that because how often would they run into someone saying, like ‘Oh I use your insurance software program, and I love it’?. But when you build tools that a lot of people use it’s really cool to meet them in real life and talk to them.

It’s all about people. Life is short, and you can make a lot of money, you can be successful, but that’s not really going to do it: It’s about the people that we work with, the money that we made we have profit sharing through the company to help their kids being sent to school. All those things are what make it worthwhile. That was always our motivation. The people.

What does a productive day for you look like?
It changed over time. Because my role changed over time. In the early days, I was a programmer so a productive day would be like not being interrupted, I built these features, I tested them.

Taco, the cartoon version of Joel’s dog and mascot of Trello

When I became the CEO there were three things I worried about: don’t run out of money, that was the first thing that I had to care about. Two, was keep the vision. Be the person that continually tells the story both outwardly but also inwardly to the company to keep them focused. And the third one was recruit great people because if you don’t have the team you’re not going to get the product. I think about a lot of the things that are in Trello today, the things that people remark about like the little things. It wasn’t because I told somebody to do that, but because the programmer that was building that feature was a talented creative person and they had the the freedom to just build it in that way and express themselves. For example, if you go to log in into Trello, there’s a little login box in which you type your email and it has this little example text. That changes that changes and it’s like these subtle inside jokes that every once in a while people take a picture of it and tweet it, because they’re like ‘it’s so funny’. Most people don’t even notice it, but the fact that people remark on it, it’s super valuable and it’s like those little things throughout the product — You can never tell somebody to do that. Like the mascot for Trello, this Taco dog, the logo. My co-founder Joel, his actual dog is named Taco, and Taco is a husky so it’s a real dog. I actually told I wanted the mascot for Trello to be this manatee, a cute cartoon manatee, and I even had shirts made up of the little manatee. And then the designers at the company didn’t really see anything in it. I never said then you need to come up with a new one. But one of them was really into Joel’s dog and made it, and that’s how the cartoon husky came to be. And it just became part of the soul of what that app was. And the cartoon nature of it showed that it was fun, and it set the voice and the tone for the app. So I think it’s all about recruiting really great people, make sure you don’t run out of money so you don’t disappear. And you just keep telling that story.

How did you experience that shift from programmer to CEO?
For most of the history of our software company, my co-founder is actually much more the face of the company. He was the CEO, he wrote the blog; people knew him. I was quietly in the background running the finance piece, or this piece, or that piece. Even for Stack Overflow when we spun Stack Overflow off, I was doing a lot of the finance in the early days, and we got to this point where we knew that we wanted to spin off Trello and we were going to take VC funding for the company and we were like ‘okay, well who’s going to be the CEO?’, and we actually thought really hard about trying to find somebody and we kind of went around and around and couldn’t find anyone. And I was like I guess I could do it, but I almost didn’t. I’m not sure that I knew I was capable of doing it. But there wasn’t a better choice. And so again I was like I guess I’m just going to do it, and I’ll just wing it and that’s still what I’m doing today.

I think a lot of time society tells different people you know you can’t do this, or you’re this type of person, or you’re only capable of these things. The trick with entrepreneurship is that we’re like ‘**** it, I’m just going to do it’. Every mistake is actually a lesson. And sometimes you might not even see it at the time, and yeah, it can be soul crushing and sad, but it’s part of the journey. You’re not going to learn how to surf because you’re going to get out on the waves and end up on the board and be like ‘look at me’. It takes hours, and you’re going to fall on your face, and probably on your knee. And get cut by the board and. All these things are going to happen and that’s just that’s part of the process.

“Assume that the whole world is your audience”

What would you recommend aspiring entrepreneurs to do?
If you’re building a product today, you should from day one assume that the whole world is your audience. Or in your market. Well, for a technology product. There’s no reason you can’t build something that everyone can be a part of. So that has implications around how you build it, and the way that you start to think about purchasing: not everyone uses credit cards, so are you thinking about this? Are you using the right tools? Then later if you want to add in some other way to pay is it going to be easy or going to be hard? When you build your app, are you assuming that everything is in English? Are you just putting all in English into the app? That might later be a giant pain in the butt when you have to pull out all those strings and translate, like fine maybe you don’t do the translation. But you build it in a way that later you can and you don’t have to rip it apart and build it again. And make use of all the SAAS tools that are out there, that are not part of your core competency; outsource it, pay somebody else to do it. It’s easy and cheap to do that now. Build on top AWOS or Azure or Google Cloud and start from there from day one. Use like Stripe or BrainTree. There’s all these tools out there to run a company. That used to be a hurdle, because you can’t do all that stuff and also build an amazing product. In some ways is harder to run a company now, because anybody can buy all those things. It so easy to build a product that does an idea. That’s not the challenge anymore. So you’re going to be competing with anybody else who has that idea, because the bar to create something is going to be so low nowadays.

The thing that’s going to set you apart is: are you building human software? Before, it used to be enough if you could write a program that talked to a database presenting the user with fields and values from the database and then stored them in the database and that was magic. It’s nothing like that today. Today, it’s about the design, the interaction, is it available on all these devices, is it available at all, can I use it in every other language, how is it being marketed? All these other things are new problems that people have to face. That opens the playing field up to so many more people and so many more ideas. But it also means it’s more competitive.

It’s so much harder to stand out in the crowd. People ask Joel, what’s the secret to success? Well go back to 2000, start running a blog when no one else is blogging. Back then it was really easy to build up an audience. You can’t tell someone today to go out there and blog, and think that that’s going to be easy: It’s not. There was a time when just writing a blog meant that you and 40 other people that were good writers were on the Internet. Everyone read it. Now everyone is able to do that. You go to Medium, click the link and boom, you have a blog. So now, it’s about distribution. How are you marketing it? That becomes a lot more important.

What has been your biggest failure?
We’ve built a product called Copilot, somewhere in 2005, 2006. Before those apps that remotely control your PC were available. It wasn’t easy to do that. Remember how your parents would call you and you’d be like ‘What do you see on the screen’ and they’d be like ‘I don’t know, it’s a box’ and ‘read me the text’ and it was like a super pain in the butt. We wrote a program that let you share your screen, like go to this web website — type in this code and boom I can see your computer, and made that sort of seamless. It was super successful and we marketed it to customer support people, because that’s what we were using it for. We were trying to install another software product that we had on people’s computers so we felt this pain, because we would be talking to them and they’d be like I have an error, and you’d be like read it to me. If you could see, you could move the mouse, fix it, and it would take five minutes to talk to them instead of an hour. We built this product to serve our own need, and then we marketed to those people. If you think about the success of ‘log me in’ and ‘go to my PC’, they didn’t market it to customer support rep, they marketed it to everyone, and got in through IT people that understood the market for this product and that was much bigger than what we were going after. We built it and grew it, made a bunch of money off of it, but it never became a billion dollar idea. Even though we were executing on it before someone else just made it a billion. So I think who you’re marketing to is a big lesson.

We’ve built a product called a bug-tracking product called BugBox, which we still sell, and my current company Atlassian built a product called Jira, that competes with it. Many years things were neck and neck in the size and scope of our companies. Atlassian just took off and became this huge multinational corporation. Some of the lessons there were that we got a head start very early on because we had Joel’s blog. That was a great marketing avenue for us to talk to developers because he was writing about technology and software and building a software company and so the people were reading that. And that was great content marketing. So we’re great, we’re fantastic content marketers. We weren’t doing any other kind of marketing because that was all we needed to do. And so that was a crutch for us. Whereas Mike and Scott you know they did they didn’t have a blog like that. They had to start and do all the marketing themselves and they got really good at all the other ways of marketing. That was another lesson.

I think it’s actually interesting because in both of those lessons I’m talking about marketing and I think figuring out your market and how you reach them is probably the biggest problem for developers because you know we say execution is everything, even if the idea’s kind of worthless but that’s a 100 percent true. You’ve got to have the right idea; you got to do the execution, but then you have to get people to hear about it and everyone asks ‘well, how do I do that?’ But there is no easy answer for that. That is the hardest part. That’s where growth hacking and all these things and flicks come up, and data analytics. Just try to understand that it’s more and more complicated, there’s more and more competition, and more and more voices to be heard. How do you stand out above the pack? Every day it’s getting harder. The answer is that it’s just a lot of sweat. Grinding it out day after day. You also have to have the right idea and execute on the product in the right way. And then also you have the market it.

What makes you worry?
I think technology is changing the world so fast: How do you handle that at a society level? What I said, like let’s build an app for the entire world, make your entire world your market; there are people that are doing that. There’s a lot of wealth being driven in technology and that kind of stuff. And then there’s a lot of people that are part of that story, they’re going to their job and their town, but they’re not part of this global economy or this global workforce and they resent it. Look at the election in the U.S. and all the stuff that’s happening in Europe, I think that a lot of that has to do with not being a part of this success. The ‘What about me’- type of scenario. And the resentment toward the ‘other people’, like those who are not benefiting from this international world and don’t like it. That conflict worries me because it’s going to happen more and more.

When you think about self-driving technology, it’s obvious that in 10 years most cars just can drive themselves, like trucks on the highways delivering goods. That’s a whole industry that will disappear. Or think about the implications for police departments that make much of their funding from writing speeding tickets right. It’s the revenue that pays for these jobs for police officers. If the revenue disappears, it means now there’s not enough revenue for these jobs. What happens to these police officers? What will they do?

When that shift happens slowly you know a new generation can come in. But if things speed up, and are happening in this cycle that’s like five years, it’s just boom boom — how do you retrain people? That becomes a huge problem for society. That’s my worry. Stephen Hawking said that world we only have 100 years left on the planet. There’s a lot of people worried about that. But there’s also a lot of people working on that.

Who is your favourite super hero?
Elon Musk. Definitely. He’s like that thing, he’s doesn’t know any better. You can’t send rockets to Mars, and Elon is like ‘yeah, I can, I’m just going to do it’. And he still might fail. The reuse of rockets, he proved it. That is solved. The fact that you can build a car, that is an electric car that people want. Done. That’s happening, it might take a few years but it’s inevitable. He sort of proved what he set out to do. Most people who come up with an idea like going to Mars, they spend a lot of time coming up with a plan. He works backwards, so in order to get to Mars, the cost of travel needs to be really low, which means we have to reuse these rockets because they’re so expensive. So that’s his first step, how to get to reuse these rockets?


Challenges expressed are in no way meant to solicit commercial acquisition.

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