How would you describe what designers do and the value that they create?

The job of a designer is to provide clarity around an idea. People can talk all they want about ideas, but the designer can take all that stuff that’s up in the air and turn it into something real, even if people hate it. That first step is really, really scary. It can be difficult getting that first thing up on the wall and to create clarity around it, and then get it clearer and clearer, until it “exists” for people. I answer questions about the thinking behind how this thing’s going to work, all the details.

The job of a designer is to provide clarity around an idea.

Having your vision come through in the product is a big challenge. A lot of companies will add a shitload of features and try to let that convey a vision. We came up with a very simple language, the path is a simple line that runs down the feed and the moments are these dots that sit on top of this path.

Then there’s other things as a designer I’ve helped to do like creating a nice palette, making the whole experience warm and feel like a nice place to keep what you’re capturing. The composer was a little goofy at the time. Honestly, I thought people were going to say, “This is fucking goofy.” I was really worried about that, but people liked it.

What are some of the unique ways that you in particular contribute as a designer?

Being a designer of a product, having a software engineering background has made a big difference, and most designers don’t even think about that. It’s important to have an understanding of the how things are built, what it takes, what’s going into what you’re designing: the framework, the tools, the techniques, and the materials.

Throwing a mock-up out and having some engineers build it might work, but the result won’t truly be great. At Path, I really push the designers to have good relationships with the engineers, so that we’re not throwing mock grenades over the wall and expecting the engineers to pull it together. We sit down and talk about problems and try to come up with the best solution on both sides.

The best product designers are technical. Take the time to learn more than Photoshop and design philosophies. Dive deeper than that. And the deeper the understanding the better. That’s something I didn’t think about when I was growing up, but looking back it has helped me be a better designer.

Can you give an example from Path of how you collaborate with engineers?

Let’s use the composer as an example. I didn’t hand over a mock-up of exactly how it was going to work. We’ve got loose specs around things, but the best stuff comes out of first forming a vision for how this thing’s going to work, and then sitting down with an engineer and making it great.

So I told the engineers roughly what I was thinking and it came out and it wasn’t that good. So we talked through animations. Simple things: it springs back, and then when it goes back in, it sort of goes out and then flexes out and back in. It just takes some time to think through and iterate the design until you get it right. You have to use it and go, “It’s not feeling right. The timing’s off. The angle on these things is off. It does a little spin, it’s too much.”

Your engineers also have to respect the process and be comfortable throwing away code. So that’s another thing designers are taught. To get to the best solution possible, sometimes, you have to toss things away.

Let’s talk about your background. What were your earliest entrepreneurial endeavors?

My mom’s a graphic designer, someone who slaves over how things look, so that’s always been in my life. The earliest thing I can remember building and thinking about is how software feels,  Mac software because we only ever had Macs. If you wanted to make software, you were forced to think about how it would look because that was the environment. You had to put pixels on the screen and lay things out. This was late elementary school, and I wasn’t really thinking too much about design and design philosophy. I was figuring out how the hell to make a piece of software. I just wanted to get a button that you clicked and would do something on the screen. Back then, that required 1,000 lines of code.

Next I wanted to make something that I wanted to use. This is crazy—I tried to make my own version of Photoshop. I dove into it but never finished. I could draw on screen, create new canvases, but even though Photoshop was a lot simpler back then, it turned into this massive project. It was buggy. I didn’t understand memory management. I looked at Adobe’s software and wondered how do I make it even better. I didn’t want to sell it, just to build it and to see what it would take and just try. That’s the first time I thought about product design.

Why did you want to put that button on the screen in the first place? Was it related to your mom being a designer?

I think I wanted to make something that mattered, and it seemed like software mattered a lot to the grown-ups in my life. And I did use my mom’s work computer. She certainly let me take a lot of time on it. In early high school, they bought me my first computer. I completely messed it up. It was actually a piece of garbage. It was in Apple’s dark era when they were making Performas and the hardware was bad. Having my own computer was a big deal. I could get booted up much faster and could spend all my time on it, and I neglected a lot of homework because of it.

I also started to think seriously about shareware and that I could sell software and maybe make some money off of it. That this was something I could do with my life. I started wondering how I could start a company.

I released a small game and a couple things. It was really difficult. I was experimenting with different tools: C, Pascal, high-level tools like HyperCard. I was making interfaces: you put it in front of somebody, then they click, and things happen.

How did you have such entrepreneurial ideas at that young of an age?

I grew up in a really small town in Canada and a lot of people had their own small businesses. The biggest business up there probably employs ten people, maybe 20. Like my mom with another guy ran the newspaper in my town. So it’s the way we live.

So when did you end up starting a company?

At the end of high school, like 1998, I started a company with Aaron Sittig. There was a company called adSoft that made a Mac version of Winamp and a couple of other tools. I thought they were cool, so I pinged them on IRC and asked if there was anything I could do for them. The guy told me to work on a project idea with another guy who wanted to work on something, Aaron.

We got it pretty far. I really got into crazy programming and product work because people I hadn’t even met in person were relying on me to get this done. I learned about network programming and how to do really advanced UI stuff. It was really difficult back then to get even something small to work because you’re sending a packet over the wire. You had to do a bunch of crazy shit to send and receive information from another server.

So while we were working on this, I found out about Napster. You could just type in whatever song you wanted, and get it. But there was no Mac version. So Aaron and I and another friend Jason [Toffaletti], who was really into networking, decided to build a Mac version of Napster. We called it Macster and released a first version in two weeks or something. I learned C++. Then we spent another month or two building it out.

This was after high school?

While I was graduating and after that. My parents had no idea what I was doing: “What, you’re not gonna go to college? You should probably do something.”

We shipped it on Christmas Day. The day before, I sent an email to [email protected] to tell them we were putting out this Mac version. Don’t shut us down. A couple days later, they replied and wanted to fly us out to San Francisco because they liked what we were doing. So we went down here. This was the first time Aaron and I met Jason in person. It turned into our first actual interview.

I was a self-taught programmer, completely self-taught. So they asked crazy questions that I ultimately knew the answers to, but it was very awkward because I didn’t know a lot of the terminology they used. Anyway, they hired us. It was hilarious because our starting up salary was $40,000. To me, that’s holy shit, $40,000.

You’re 19 at the time, right?

Yeah, and I’m going to be making more money than my parents combined. This is going to be crazy. They were totally low-balling us, which was fair because we didn’t know what the hell we were doing.

So we worked on the official version of Napster for the Mac. That was big. We went from making nothing things with some friends to something with millions of users and that the whole world was excited about. We were there very, very early. There were five people and no one had heard of Sean Parker and Shawn Fanning yet.

We got paid to learn Objective-C and how to make software and design for Mac OS 10. We learned so much about engineering. I was writing a lot of code and designing at the same time.

Was Napster growing while you were there?

Yes, I think they had more marketing and business people than engineers. To tell you the truth, there weren’t designers. They relied on Aaron and me to produce a lot of the design work. Even after we grew and hired a full-time designer, a lot of product stuff came from the small engineering team.

Back then, hitting a million users was a big deal because we had no idea how to scale. The whole office cheered when one of the engineers pulled it off. We later got to many millions of users, and the company may have gotten to 80 or 100 on staff, but it wasn’t crazy.

Why did you transition away from Napster?

I left after a couple years to work on some more of my own stuff. It’s a lot of fun to have smaller projects and the freedom to build whatever you want. I moved back to Canada and did contract work for some companies. One turned out to be Flickr and another one was called imeem, which I joined and then left eventually because I disagreed with them product-wise. That’s where I met my wife.

I was back in Canada when Shawn told me he had met this guy Dave. He wanted to have a dinner and talk about some ideas we could work on together. We went through a lot of really crazy, really bad ideas, but the discussion was really good. I like Dave a lot, and I had known Shawn forever.

Finding someone to co-found with is a big deal.

You’ve got to be able to mesh, definitely. Dave is really good at product and we can talk about product all day long. We’re a pretty good pair. Dave’s really good at externalizing our vision. He can get up in front of a crowd and get the message out. I can sit down with Photoshop and the engineers and talk through stuff.

Did you start prototyping? Or did you first sign something or start a company?

I started prototyping some things and said we’ll see what happens. A lot of companies when they start have to get everything on paper first. There’s no trust there. It’s not a good sign when you talk about shares before you even know what the hell you’re doing. I don’t think that way.

We eventually came up with a few things we were interested in. But it took a while. I was in Canada for two years hacking on stuff and trying to work through different ideas while I waited for my green card. You couldn’t really start the project in earnest until we were all in the same room.

Have there be any surprises about founding a startup?

I noticed one thing recently. Early on in a startup, everything you do every single day plants a seed. A year later, those seeds are big freaking plants and trees. This startup is a mirror. You see your personality amplified and reflected in how the company behaves, so it can be scary. For example, I’m not very social, so for a while, we didn’t hang out together that much outside of work. That’s something we recognized and are fixing. So maybe you accept it or maybe you can celebrate it. When you start a company, it is going to be you, for better or worse.

Early on in a startup, everything you do every single day plants a seed. A year later, those seeds are big freaking plants and trees. This startup is a mirror. You see your personality amplified and reflected in how the company behaves, so it can be scary.

Do you see yourself as a designer reflected in the company as well?

Yeah, between Dave and I design thinking was injected from the get-go, as opposed to being stapled on later. But it was a challenge in the beginning figuring out the designer’s role and effect on process while figuring out our vision. Especially when all you want to do is prototype and build things as quickly as possible. But I’ve seen startups that are way too eager to just write some code and ship it and see what people think.

Where do you see Path going in the future?

We think it’s really important to build for ourselves. You have to be users of your own product. The easiest way to build a good product is build something you truly want. We’ve built a product that people trust to store the most real moments in their lives in an honest way, a space that’s with them all the time that they can put themselves into. That is something I’ve wanted for a long time and still doesn’t exist. People edit themselves on the Internet all day long. The most honest places right now are probably photo apps. Like iPhoto on your hard drive, but that’s not connected to anyone.

Our vision at Path has been to create an intimate, private space for sharing moments. And this connects to a very personal vision I have. Growing up, I remember being fascinated by these old photos my parents took before I was born. And it’s like, my dad looked like that? His glasses were enormous. But they only have a couple photos. There’s all these moments and stories that they don’t have anymore. They didn’t have the tools for it. It’s sad.

So first, I want a tool where I could just keep it all and trust that space. Second, if I were to have kids, it would be interesting to have a catalog of a life that they can look back on. That’s a ways out; Path has to be around for 20 years for that to happen.

Last question, what does meaningful impact mean to you?

We think about the meaning behind everything we make. I guess when I say design thinking, meaning is baked into that. For every feature we put into the product, we ask, “What is this feature really?” When someone says they want A, what are they actually asking for? What is the meaning behind the question? Why is the product currently failing them? When I think of meaning, I think of all the questions we ask, they’re all part of that meaning bucket. Every single thought we have that goes into this product has meaning baked into it.

It’s something that’s on my mind every day. Every time I use the app. When you’re a startup, it gets harder to use your software because you’re using beta builds and you’re finding bugs. You hate everything you put out there. Like, I’ll think it’s fine and I’m happy with it, but the moment it’s out there, I hate it already. That’s when you think of ten different ways it could have been better.