So start at the beginning. How did you first get into entrepreneurship and design?

I was super inspired by the Macintosh and really drawn to the design of it. My grandfather got me a Mac Plus when I was four years old. The original Mac came out in 1984, so for people like me who were born around 1980, you were old enough to be sentient and thinking, so you learned computers.

Remember that program Print Shop Pro? You could make cards and banners with a dot matrix printer. I would obsess over the layout and having everything pixel perfect. Kid Pix was great too. I was never a particularly good artist. I couldn’t draw or anything, so I gravitated towards computers.

But my first memory of really getting into making stuff and designing things with computers is spending a bunch of time making things in HyperCard. HyperCard was amazing. You opened it and there was a blank page. You could draw on and link it to other cards and script it. It was like the Web before the Web. The scripting language is the best one ever. I’m still waiting for a language as awesome as HyperScript to come along. I used it to make presentations before Keynote. I made this game called The Great Adventure, which was basically a not as good version of Myst.

I got so into HyperCard that the teacher, who was in charge of technology for the school district, she asked me to help teach a class on it to the teachers in my elementary school. So in fourth grade, I taught that class on the weekends.

When did you first get exposed to the idea of design?

I think it was my grandfather. He was an interesting character. He was a doctor and very involved in the U.S. and the international ski community. He was the vice president of the International Ski Federation (FIS). My grandfather would go to Switzerland for FIS meetings and bring me back stuff like Leica cameras, Swiss Army knives, cuckoo clocks. And all these things had Helvetica on them. He’d bring me a different Swatch every time he’d come back from Switzerland. He was also an investor in this company called Bollé, which makes sunglasses and ski goggles. He was really into photography and had all these cameras. He had a darkroom in his basement and a lot of really great art.

I come from Helena, Montana, which is a very small town. The population was only 25,000 [at the time]. But when you went into my grandfather’s house, it was completely mid­century modern, built in the 50s. It was like a case study for me. The lighting, the kitchen, it was all very purposeful and design-focused. Every gadget in the house was Braun. He had these beautiful knives from Switzerland for family dinners. One of my favorite pieces at the dinner table were these handcrafted wooden bowls. The house was filled with Swiss products.

Most of elementary school and all the way through eighth grade I literally went to their house every single day after school to build stuff on the Macintosh and hang out there. It was my favorite place. I think that has to be it. Something about the aesthetic of his house, using the Macintosh that had different fonts, borrowing his Leica cameras. I got really obsessed with fonts. I had a poster on my wall as a kid with all the different fonts. I still have it today, only now it’s funny. So I really looked up to this sense of taste and design and high quality that my grandfather had.

Were there other key experiences you had as a designer when you were young?

In high school I was editor of the school paper. I would get to school before everyone else and I would stay past when everyone left. I would be there in the dark and leave in the dark most days because I was laying the paper out by hand. I would use Photoshop and Aldus PageMaker and do things like make the text wrap around the image or cut the image out. I’d figure out how to embed new fonts.

I’ll never forget this one time, I was putting together the Christmas edition, and I figured out how to get this Olde English font. (At the newspaper I also had the poster of all the fonts above my desk.) And I embedded this new font wrong in the PageMaker file. The teacher who oversaw the newspaper took the files over to the local newspaper to print it. When she saw that the font was improperly embedded, she chose a new font for me.

When I found this out, I went to the Helena Independent Record and stopped the paper’s production. I really felt the font was a huge part of the finished product. The design had been compromised and it really upset me. I got the font put back in, re­plated the whole thing, and ran it again, despite the trouble I got in with my teacher and the school.

I think that beget my interest in the Internet. I had my own computer in my room, an old Windows 3.1 laptop. I taught myself how to program and would make things on the Web, like on AOL Hometown. I had my website there with GIFs and everything. I saw HTML just as HyperScript. And I was used to PageMaker, but on the Internet you had to do it all by hand and HTML was really crappy back then.

I also took a lot of photos for the yearbook. I probably took like 10,000 photos in high school. I also took a drafting class, which was awesome. Mr. Duff had the fastest computers in the school because they had to render AutoCAD and 3D Studio MAX. It was where I encountered keyframing, where you make this object and animate it and the program will fill everything in. I got really into that.

There was no computer science stuff in my high school at all, but there were a few of us who were self-taught.

What happened after high school?

When I got to University of Colorado at Boulder in ’99, I got this awesome computer and things were getting crazy with Ethernet. People were playing HalfLife and other games on local area networks. Then Flash came out and to me it was like 3D Studio MAX. So I’d make these cool Flash intros and things that’d fly around and 3D text and stuff. One day I got a call in my dorm room from someone who asked if I’d make a Flash intro for their business for $1,000. I was like, “Holy cow.” So I just started making Flash intros and animations for people and then someone asked if I could make them a website. So I learned Front Page, Dreamweaver, Fireworks, all this stuff. I got so into the Internet in the first couple of months of freshman year that I was like, screw it, I’m going to stop ski racing (originally I was going to ski for Boulder).

I put up this website called DMDesignStudios.com: Dave Morin Design Studios. I had a Flash intro and my tagline was “Whatever Your Mind Can Imagine We Can Create.” Flash intros were the rage back then.

I didn’t know anything about business, entrepreneurship, nothing. So I called my uncle in Helena who was a corporate lawyer and asked him to teach me how to start a business. He walked me through LLCs and Inc.’s and sole proprietorships, all this stuff. QuickBooks. I started learning about tax law. I was like, “This is how the world works.” I started buying and expensing all the best equipment. I had a cellphone, back in freshman year when nobody had cellphones or even pagers. I was running my business while I was in college. That’s how I really got into design and entrepreneurship in earnest at the same time.

This whole entrepreneurship thing—it brought incredible freedom. It’s a level of creative freedom that you don’t get any other way.

So your first business you started solo?

Well, the next important moment in my career was finding partners to work with. Because like I said, I was never the best at art, but I was getting into more and more complex projects. My girlfriend at the time introduced me to this guy Alex, who turned out to be this fantastic illustrator, designer, and artist, and he knew Flash, and I was really good at products and the way the things should work and the entrepreneurial side. So I was like, “Dude, we’ve got to join forces.” So we collaborated, and he’d do cartoons in Flash and made the products even more insane. We did this one super amazing Flash intro that had full out cartoons talking.

That was when I realized I loved design and that I could design the way the interface should work. (Back then I used to call them layouts, like how you do a newspaper layout.) I had done some decent design work myself, but with a partner who’s like a crazy epic artist you can really do stuff. We worked together on project, after project, after project, and started to get bigger projects. I also figured out that doing things with databases was hard, so I found this incredible database guy. I realized this combination of super good technology, databases, a real artist, and me being like, “This is what we’re building,” was really powerful.

Meeting Alex has informed the way I have approached business ever since. Great products and great design happens through great partnerships, through real partnerships. Alex and I were great partners. Now Dustin and I are great partners. I’m deeply product-focused now and Dustin’s deeply design–focused. It’s the partnership between us that makes this thing go. It’s truly like the ying and the yang. We’ve done personality tests and we’re exact opposites.

Great products and great design happens through great partnerships, through real partnerships… If you have a co-founder, finding the yin to your yang is really important.

If you have a co-founder, finding the yin to your yang is really important. Obviously, both Dustin and I are design thinkers, but there’s also this neat yin and yang relationship. He’s incredibly introverted and internally focused and deeply thoughtful. He’s a designer of unparalleled skill and an engineer, too, which a lot of people don’t know. He can engineer all the way across the stack. It tends to scare our server engineers when he messes with core infrastructure, which is awesome. So we complement each other. I’m much more about communications and marketing and brand and product and vision and understanding where the market is, what can be built.

After college, then you came out to San Francisco, right?

When I graduated, I went through this tragic breakup and was really upset and didn’t know what to do with my life. In Montana, “California” is like a sacrilegious word. Because Montanans think Californians ruined Montana. They come here, they buy and then ruin the land, they subdivide things. All these people have bumper stickers in Montana that say “Open Season on Californians.” And what I knew of California was from watching Baywatch and CHiPs, so I thought all of it was like Los Angeles. But then Amy, a friend from college who is from there, told me I should really consider living in San Francisco.

I was really in love with the Internet and Ball Faser Studios, and San Francisco seemed like an interesting place, and my friend was telling me I should move there. I flew out here and hung out with Amy and two other girls from college that lived in North Beach. I’ll never forget driving up over the 101 and seeing San Francisco for the first time because I’d never seen a city that big and I was scared out of my mind. The biggest city I’d seen up until that point was Denver. So my heart just like stopped. . . I was so scared. I had no idea how I was going to live in this place but I also was like, “I think I can figure it out.”

So you moved to San Francisco. Did you get a job right away?

So my very good friend Kelly and I actually moved out to San Francisco together and tried to figure out how to get jobs at Apple. Kelly had been an Apple campus rep and I used to love Apple, but the computer sucked at the time. That’s when there was this blip in the universe and Macintosh wasn’t awesome anymore when Steve was gone.

So she asked me to talk to her boss because I knew about the Internet, so she thought I could maybe help Apple. I got to know her boss, and then I talked to her boss’s boss and her boss’s boss’s boss. And when we got to San Francisco, I continued interviewing until I was pitching John Still, the VP of Education at Apple, on the idea that they should sell more iPods and computers to students and that there were some different ways we could do it. I got an offer and accepted.

Back then we literally couldn’t even give away a computer to kids on a campus because they were like “Dude, I want a Dell.” My first year at Apple, we gave iPods to every student at Duke to convince them that putting their content on it was a good idea. So I spent a bunch of time at Apple and learned a lot there.

So after Apple you worked at Facebook, but I’d like to skip ahead. Can you talk about starting Path?

The reality of building a company is that you think of every idea that could ever be built within the first six months. So you have to pick an idea space to go after. We were all about mobile. We were looking at all of this data at the end of 2009, right before I left Facebook. Mary Meeker had published her annual Internet report, and there was this one slide that showed that mobile Internet would be bigger than desktop Internet within three years. So having worked on the Facebook platform, I knew it would take three years to get a company up and running to the point where you can have influence in the world.

The really crazy thing about the chart was that desktop Internet started to decline. It was like, “Oh my God, I spent 10 years building web stuff for the desktop and for the web browser, and all those skills will be worthless in three years.” So I said alright, I have to think about and learn how to design interfaces on mobile.

The reality of mobile is that the screen’s so small. There are 17 sensors. It’s like another planet. You have to think differently about use cases, about the actual physicality of the UI, about the different data that you can access. It’s a totally different platform.

That was a big piece when we got started. We realized that there were things that didn’t exist in the mobile world. So early on, Dustin built this little app called Small Rule. (This was January or February of 2010. Dustin might have built it on the weekends or like in a week or something.) It was a stream of photos that looked like a filmstrip going down a web page. You could put photos on it and every user had a follow button and that was it. I’ll never forget, we showed it to Aaron Sittig and he was like, “I’m not sure anyone would use that.”

Dustin and I talked a lot about photos and sharing photos. At this point, there was no Flickr for mobile. There really was nothing interesting going on in mobile, just a lot of singular utility apps. We started talking about how we really liked this way to share photos with our family on our mobile phones. Dustin’s family’s in British Columbia and mine’s in Montana.

The other thing that people did a lot that year with mobile phones was checking in. So clearly people want to collect stuff about their everyday life with their phone, but the incentives were still off on things that were out there. It seemed there were also problems with social networking paradigms because they don’t really map to mobile very well; the more popular ways to do social and mobile were communications apps, like texting.

What else drove you and Dustin’s direction besides mobile?

We also thought a lot about how no one was building the Apple of our generation. Dustin and I looked at each other and knew we wanted to build a company. What bonds us together more than anything else, more than the product we’re working on, is this idea that companies in our generation aren’t going long. Besides Facebook, who else in the Valley is building a big, lasting organization? In our parents’ and grandparents’ generation, there’s all these cool companies, GE and IBM and Apple.

So our whole thing was that we’re going to build a company: we don’t want to build things to sell, we want to build an Apple. To us, Apple means design and innovation over time. So 30 years from now, you will have accumulated successes and failures and invented technologies that ten years ago weren’t useful and now are, and it will have played out over a long-term time horizon and been done in a way that always put design first. We looked around the Internet and didn’t see any other company doing that.

So our whole thing was that we’re going to build a company: we don’t want to build things to sell, we want to build an Apple. To us, Apple means design and innovation over time.

How does that tie into Path today?

That is Path at the highest level. We want to design products that make people’s lives happier and better, and we want to do it through design. We want to run a completely design-first, design-driven, design-led company. So that keeps us going here.

We want to design products that make people’s lives happier and better, and we want to do it through design. We want to run a completely design-first, design-driven, design-led company.

We’re working on a lot of our next products right now. We’re more than 50 people now, so we’re big enough that we can do multiple things at once, which is pretty great. I’m really confident that each of our teams will come up with breakthrough designs. We’re trying to make a breakthrough in simple interfaces.

We built some interesting innovations with Path 1. We did some cool design stuff with how photos open and closed and how we fit more information onto each screen. We also messed up some stuff trying to get people to add too much to each piece of content.

We made a lot of mistakes that don’t matter on the Web. On the Web, you can put people through a five-screen flow and it’s no big deal. They still put content in. On mobile, if it’s more than one click, people are like “screw this,” and won’t do it.

Can you give an example of how you approached designing for mobile?

For Path 2, one of our biggest innovations was figuring out how to allow people to contribute the types of content that they want. We saw that people were uploading screenshots of different apps, like of their iPods and maps of their runs.

People were taking photos of movies in movie theaters and photos of menus at restaurants. People clearly wanted to contribute these different kinds of data to their Path. We initially forced people through a flow of take a photo, then are there people, places, or things in your photo—it was not working. So, how do we incorporate single-use posting and make the whole process super delightful, not get in your way, and eliminate the cognitive overhead?

We went through 20 different interfaces of the exploding composer or radial menu that we have now in Path. We started with wanting people to contribute six different types of content. How do you think about that when you start designing the interface? You make a six-box grid, and you try it horizontally, vertically, and you put text in the box, an icon in the box. We did all of that and it sucked. You see it in a lot of applications actually. When you open up the interface, you push a button and get all these options. Immediately, the cognitive overhead goes through the roof. And we knew there had to be a better way. So we kept going and kept going and kept going.

At one point, we designed it so that the content options were in a text box, almost like a search field. When you clicked on it, a menu would drop out with all the different post options, and you could search. It could scale infinitely, and we could have all these different composers. But it sucked. So we kept going. Like, can we get it down to single icons? It’s a touch interface, so when your thumb hits the screen, maybe something can explode out. We kept going until we found the interface that we have now. If we weren’t led by design, we wouldn’t have been able to get there.

What does “led by design” mean to you?

Having worked at Apple for a long time, listening to Steve and Johnny, and just being part of the Apple ethos has impacted how I approach design. We had this saying at Apple, “That doesn’t suck.” Because Steve would look at an interface and say, “This sucks,” “That sucks.” So at Apple, we’d work until something didn’t suck anymore.

I think you have to look at design and especially at user interface that way. Any time something in your hand is not right, you have to have the guts and the courage to throw it out and do it again and again and again until you get there. We try to do that pretty relentlessly here; it’s a big part of how we think.

The reality is, it takes a lot of time. It doesn’t happen in a weekend hack session. To crack open these interface problems, it takes 20 iterations, using it for weeks, thinking through what we want. We spend a ton of time to get to the right level of simplicity. We probably take more time than most companies and than most venture capitalists would like us to, and we’re not afraid to do it because it produces a higher quality product.

The reality is, [good user interface design] takes a lot of time. It doesn’t happen in a weekend hack session.

And that’s especially important for mobile applications because people expect them to work, unlike web apps where they expect them to be busted. And you can’t fix mobile apps overnight like you can a web app, so it’s has got to be pretty good when it goes out the door. So you have to take extra time with mobile apps.

What are some challenges you’ve faced?

Simplicity and saying no to things and focus is hard. Choosing to do these three things and nothing else, and ensuring that we’re focusing on the right things at the right time. I look at my role as editorial. I consider Steve Jobs the greatest editor of all time and that the best entrepreneurs are the great editors.

We have had thousands of ideas, and we’ve probably already thought of most of the ideas that we’ll ever do. So the question is which one should we do now? It can be incredibly scary because deciding what we’re working on means you’re betting that six-month period on doing just that one thing.

It’s a big gamble.

And the other ideas you are trading it off for are probably also good. Steve Jobs used to say, “There’s no virtue in saying no to the things that are easy to say no to.” Saying no to the hard things is what really makes a company.

We say no to a lot of really interesting ideas here, and so that plus saying yes to a few key ideas is the hardest thing. You get better at it over time, but we didn’t know if Path 2 would be good. I don’t know if what we’re working on now will be either, though I think it is. It’s hard to know until you put it into people’s hands. We just released version 2.5, and some of it worked really well and some of it didn’t work at all.

Every single idea in play takes up space in your mind and takes up space in the user’s mind

It’s also really important when you release something (a) not to dwell on it for too long and (b) if it’s not working or not getting traction, edit it out. Every single idea in play takes up space in your mind and takes up space in the user’s mind.

We try to be pretty relentless about that. For example, when we launched Path 2, we had six buttons in the composer. No one has even noticed that we only have five now, which is really funny.

What did you take out?

The button that says who you’re with. Only 3 percent of our users ever touched it, so clearly it wasn’t working. We could have turned it into something else, but you know what? Just cut it, and go do something else. So we did movies and books instead, and people love that. Designers always say don’t be afraid to edit out ideas that aren’t working.

Besides your editorial role, what else is part of your role at Path?

My job is to create an environment of design and where the culture feels as absolutely creative as it possibly can. Also one where people feel ownership over their creativity and over a product. To say, the market’s going in an interesting direction here. Or that this is something our users might want. To provide a framework for, “I think this is a good place for us to go,” but then also to hand it over to people in the company to generate thousands and thousands of ideas.

I make sure that we think big enough and drive our values into everything that we do. So we obsess over things here that a lot of people don’t. We really care about quality, about simplicity, about intimacy and the meaningfulness of the information.

We obsess over context and also over stories. How do we add one little bit of information to make this a better story? So, for example, our sleep product lets people add to their Path when they go to sleep and when they wake up. It started out based on the idea that people want to know when their mom’s in bed so they don’t call and wake her up. We also have a writer on staff who is incredible, and we designed with her in mind. Like what if we built her a logical tool where something happens if she ate dinner at 9:00 p.m. and went to bed at 2:00 in the morning? Because clearly then she’s been out having a crazy night, so maybe the sleep story adds commentary on her day. We try to take creativity in context and storytelling to a different level.

I also see it as my job to challenge people to do things more creatively than they would have otherwise or to work with somebody they wouldn’t have considered. Or like asking engineers how do we do that? How do we tell that story? Which is part of turning engineering into a story, rather than engineering for engineering’s sake.

What other advice do you have for designers starting companies?

If we succeed here, our greatest product will be this company. So Dustin and I spend a lot of time on designing the organization, which is pretty new to me at this scale. I managed some smaller teams before at Facebook, but this is the biggest organization I’ve managed.

One of our guys here from Google always says, “engineering is easy, people are hard.” So designing the company, how we work, what our expectations are, what our values are, standing up for our values—those things are a whole other level. What information people read, how we think about things, how we share information.

Can you give examples of what you do to design the company or of cultural hacks you use?

We invest a lot in spaces and objects that are inspirational. For example, we have this incredible office. We’re in the top of a tower in SOMA with a view. I really subscribe to the idea that well-crafted spaces elevate us. People need to be surrounded by beauty if they’re going to create it. If we worked in some grungy warehouse, perhaps our product would be less beautiful. So you need a well-crafted space and a beautiful view or beautiful art.

Whatever it is that inspires you, have it around. You have to walk the walk, not just talk it. That’s hard for some startups and some companies, but we’re not afraid to invest systemically. Our office was designed by Lauren Geremia who mostly designs bars and restaurants. I got in touch with her after I noticed the amazing light design in a bunch of the restaurants in town like Umami and Salt House and Coffee Bar. I also liked her general aesthetic. I wanted our office to feel more like a home. Bars and coffee shops feel warm and like places you could hang out for a while. Now, there are other startups like Causes and Lookout that are in the tops of all the towers and working with Lauren to design their office spaces. So these things make a difference. You can’t see it in your growth rate or in the numbers, but you ultimately feel it. You feel it in the brand, feel it in the experience.

As far as real culture hacks—we fail at a lot of things. We’ve really fallen down at times, in terms of communication and transparency. Not on purpose, but as you grow, some people get out of the loop. You have to decide what tools to use and why. We tend to choose the best designed ones. We use Trello and send a lot of email around here. We try to keep things simple, not too much complexity, but enough that communication works pretty well.

Last question, what does meaningful impact mean to you?

The word “meaningful” is deeply embedded in our brand. Personally, I want to make products that help people live happier and more meaningful lives. Both of those concepts are important. Happiness could be defined as having no discomfort in your life. Achieving meaning in your life is feeling fulfilled. Sometimes they’re at odds, and there is a tension between them, which is really powerful. If you’re chasing too much meaning, you might work yourself into the ground, and then you’re not happy because your personal life’s falling apart.

If we’re helping to drive forward products and ideas that help people have more happiness and meaning in their life, then that’s probably pretty good.

I tend to focus on that and not anything else, but sometimes, we get lost in the forest while we’re looking for it. This morning, my sister’s husband is having surgery and that’s really hard. She’s posted to Path and my family is supporting and mourning with her and that’s bringing her a deep, deep, deep happiness.

We want to give that feeling to everyone. If we keep doing that, and stay focused on people, then we get to keep doing what we’re doing. If we get lost, then this place will implode.