Start by telling us a little bit about you and how you got started in product design.
My first product I ever worked on was a wiki for the UCLA Philosophy Department. I built it because I was really annoyed that the students at that part of that department didn't really know each other. So I got on the internet, which I really had no idea about then and just started Googling wiki software. I downloaded the software that Wikipedia uses and I rented a server on DreamHost and I put it up there. I had no idea how to install software to server, so I just would go on these message boards and ask people how to do it and these people would get really annoyed with because and I was the ultimate newbie.
Eventually I just give all these people root access to my server so they could help me install this software. It’s kind of amazing that it totally worked out. Nobody hacked me or tried to rob me of all my credit card information. The great part was I actually built something and the Philosophy Department used it officially as the way for students and professors to communicate. It's like wow, you can just do something on the internet and have it work and have people like it. That was pretty cool. That was my first taste in building something on the internet. I had never been a designer. I was not a programmer. It was just if you hassle people enough and build something people want to use it will end up happening and that's the history of all the stuff I've worked on.
In other words, if you have a good idea and you push people around into helping you make it and maybe it will get made and maybe it will be awesome.
What year was this?
There's no excuse for not doing things and I think most people still think it's super crazy to do anything that's not a regular job.
This is 2004, 2005. Then I graduated from school with a degree in Philosophy. I had no idea what I was going to do so I went to live on my older brother's couch and ended up reading blogs for the first time and I came across this guy, Seth Godin's blog who's a great personal hero of mine and emailed him and I said, "I really want to come to work with you on this project you're starting." He called me on the phone the next day and we talked for 10 minutes and then he said, "I just bought you a plane ticket to New York. I'll see you in two weeks." That's how I ended getting involved in startups. Doing design, I worked as a designer intern and lots of other things at Squidoo, which became a very huge product very quickly and it was kind of miraculous, again, for me to be working as a designer on this company that millions of people used.
I don't think I took this for granted. It was always amazing to me that this was real, like people were using this kind of stuff. You look at the Google Analytics, like a million people use the thing that I helped make, which is pretty awesome. During the whole process I started to think about ideas but still didn't really have the confidence to start something of my own that wasn’t for someone else. It wasn't until I met this guy Amit Gupta who was actually my first roommate in New York that I got the confidence to build my own thing. He started this company called Photojojo and it became this super obvious to me that you have to just start things. There's no excuse for not doing things and I think most people still think it's super crazy to do anything that's not a regular job. If you run a startup and you hang out with people that run startups it's not very unusual but for most people it's a pretty bizarre thing, especially technology because technology is kind of weird still. I mean, hopefully learning to program will be legitimately cool soon, but growing up the only people who wouldn’t make fun of me for being a nerd were people in the Star Wars chart room I followed my older brother into.
So I was a freelance designer I would just tinker around with things and Amit had started this other project called Jelly with our other roommate Luke Crawford. Jelly was just inviting strangers into our living room to hang out. I started meeting all these people who were making stuff and it was almost like if you weren't making stuff on your own you were weird. You know? Then it was kind of a switch in my head, "You just kind of have to be doing this sort of stuff. It's your own life. You have to pick how you spend your time." And if I'm going to spend my time, I'm going to do something that I really care about and want to do. That's when I started thinking about actually starting my own company and just ended up doing it after saving some money from freelancing. It's one of those things where it feels insane to start a company until you do it and then it feels obvious and you can't do it any other way. Right?
It’s crazy not so much in that you have company and paychecks from it but more that you're actually doing something on your own. That's important, I think, part of the human experience is being 100% responsible for something and being responsible for other people and making something that people use. You're responsible for those people. The first company I started was thing called Boy Girl Talk with my friend, Ian Van Ness, and we launched this product Rumplo, which became the most popular t-shirt site on the internet for a little while and it was just a way for people to share t-shirts. It was kind of like early social commerce website.
Did you guys handle any of the logistics or were you just the interface for the people selling t-shirts?
We were just the marketplace, the middleman between the people who made stuff and the people who wanted it. Before then if you wanted to find cool t-shirts you'd Google t-shirts and you'd see Threadless and a bunch of really horrible companies like Pacific Sun selling bad t-shirts. If you spend enough time on the internet you'll find really amazing artists making really cool t-shirts but it's really hard to find them. It's like if we could make a place where all these t-shirts from all over the world can be found in one spot that would be pretty cool. Sort of like Amazon is to books as Rumplo is to t-shirts. we didn’t actually do the fulfillment, We would just link to the shops where the t-shirts were being sold.
For us it was kind of an experiment. We didn't really particularly care about t-shirts, but we wanted to do something and had to start somewhere. Luckily it became kinda popular. It's still the most popular thing I've ever made actually.
What happened to it?
We have to start making money off this so we started selling ads but we did it in this really crazy way where we would make and design every ad that was on the site.
We built it and it was really cool. A lot of people sort of copied it and we started getting traffic but we were sort of our own worst enemy in the sense that we didn't know how to improve it, we just endlessly futzed with it.
For example, I decided that we didn’t want any ads on the site and ads are really the only way for us to make money. We played around with affiliate fees but that was super onerous and it didn't make any money. We were just like, we were just really happy that we made something and we didn't really think about the business of it. For six months it didn't make any money and we sort of burned through all of our savings and then we were like, shit. We have to start making money off this so we started selling ads but we did it in this really crazy way where we would make and design every ad that was on the site. So if you were a T-shirt company and you wanted to advertise on our site you couldn't just put an ad and pay us, you’d have to wait for us to design an ad for you.
Crazy right? I would email so with American Apparel and say you guys should be advertising on our site and they were like like “Yeah, that sounds awesome. How many visitors do you have? A million? Cool, ere's a bunch of money.” And then I was like, oh, by the way, you can't just use your regular ads. We have to make an ad because we feel very strongly that your ads suck and we only want really cool ads on our website. And they were like, “okay…” It turned out our ads performed really, really well but it was just a shit ton of work to make every ad that went our website and we only wanted t-shirt companies to advertise on it. We didn't want The Gap advertising on it. We didn't want Viagra ads on it. We just wanted t-shirts on it. We thought that would be really cool.
It worked in the sense that we were able to support ourselves for a little while but it was not making any money for real and it wasn't like a company and then after a year of doing that we basically stopped working on it so we could work on this art marketplace. We thought we’d finally figured out how this stuff works. Now we can do the thing that we always wanted to do. It turned out to be a huge disaster in the sense that we knew nothing about art. We thought we could make the first art marketplace where every piece of art in the world would be available to view and buy on one website. I walked to Chelsea and into all the big galleries and said, "Hey we're going to do this thing. We have this other really popular site. You guys should put your art online for the first time on our new site.”
A lot of them were like that sounds awesome. And we're like, really? All these galleries put their art on the internet for the first time and then then the day that we launched all these galleries were on there and it was really amazing but then all these artists from around the world who were selling their stuff on Etsy and Craigslist and all these sorts of weird places were also posting their art to our site, which was exactly what we wanted.
And the galleries were apparently very surprised by the fact that not every piece of art on our website was up to their standards so the day after we launched all these galleries took their art down from our website, which was a huge disaster. Now we only had the very low end of the art market, which could potentially be huge but for us it's not really what we wanted to build. It was kind of an interesting thing because we always thought we were successful because we knew nothing about this art world and we always believed in this certain naiveté and thought if didn’t know something about an industry you can go in there and do something nobody else would ever think to do because we're so stupid. A lot of tech people talk about that as sort of one of the golden rules of starting a startup. Do something stupid. I think that's pretty stupid. We knew nothing about the art world and one question would have saved us six months' worth of work. All we had to ask was, “Oh, would you galleries mind if your art is mixed together with some horrible art?” They would have said, "Get the fuck out of my gallery.”
How did you guys react to that?
It ruined me in the sense that it's really hard to work for other people now. Making stuff you want to make is awesome, even if it doesn’t always work out.
It was a bummer. We spent all this time. We made this beautiful website. We took all the stuff we learned selling t-shirts and applied it to this totally other thing and we did build the best art marketplace on the web. The fact that people could go in there and browse all these different ways, they could look by color and price and country and all this cool stuff but if you don't have the support of people who you want to support, if it's not mutually beneficial then you're kind of screwed. For us it was like we're going to take over this industry by being really stupid but it turned out we were just stupid. After that we were like I don't know what to do with this company anymore so we sold it to these Australians and that was the history of that.
That gave me the confidence to continue to do new things, though. It ruined me in the sense that it's really hard to work for other people now. Making stuff you want to make is awesome, even if it doesn’t always work out.
One of the things that I did recently was I started a studio with five of my friends though. The whole idea is there we'll do work for other companies, which to me is always a weird thing. After I finish with that company, Rumplo and the art site, I just told myself I'm never going to work for anybody else ever again. Immediately after that I went to work for somebody else. It took me a month to remember that working for someone else can really suck and it was a huge disaster. They really didn't want to build new stuff, they just wanted to do the same thing over and over again. Once you work for yourself its really hard to go back. But now it’s a little easier because I think we can help companies make new stuff, and that’s where it gets interesting, if we can actually accomplish that.
What ever happened to Rumplo? Why couldn't you have just gone back to working on that?
We could have but it wasn't making enough money to really be a company. We couldn't hire people. We could barely pay our own rents with it. I think it was just a thing like we were burned out on it and we thought it's better to just go do something new than continue to be burned out on something like that.
Do you ever regret continuing to start new things rather than just keeping something going?
And my expectation was that maybe it is something I could work on for 10 years but it didn't work out.
Yeah. One of the other things I really admire about this guy Amit Gupta is his company Photojoto that he worked on for, I don't know, almost 10 years, something like that. I always thought it's amazing because every year Photojoto gets bigger and better and more interesting and more clever. That's really kind of amazing to me. I've always thought that's something I want to do, work on something that I'm so passionate about, I care so much about and love working on every day that I could work on it for 10 years. We started this other site CollabFinder I thought maybe that would be that. It was like, okay, we're going to raise funding for this, we're going to be a real company. We're going to have paychecks, we're going to have an office, all that sort of stuff. And all that sort of stuff happened. And my expectation was that maybe it is something I could work on for 10 years but it didn't work out.
What made you think you could work on CollabFinder for 10 years rather than Rumplo or Print Society?
I think the difference was that there was a certain maturity in the process of building CollabFinder that I didn’t have with the first company. It wasn't just building something for the sake of building something, which I think Rumplo and Print Society pretty much were. It's like we wanted to build something and after our launch and we got press, we're like, "Okay, great. Let's move on to the next thing." It wasn't really an intentional... We didn't even really understand, I think, or at least I didn't that once you launch something, you're at like the first 1%. It felt like we were 90% done when we launched the first company. We thought he confetti would come down, and the checks would start rolling in, and that would basically be it. We didn't, or I should say, I didn't, think that was the first baby step in a long marathon. We sort of felt let down like, "Okay, we've done all the hard work. Now where's the confetti," but nobody's going to throw confetti for you.
One of the best things I learned from Seth Godin is that nobody cares about you. every day I got emails from people who tried to sign up for CollabFinder. We only allow Facebook login and they email us and they said, "You asshole. You're so obnoxious." I'm like I made something for free you could use and you're calling me an asshole. It's really because they really don't care about me and they only care about themselves, which is totally natural. Maybe it’s universal rule. When you start to delude yourself and think people really care about what you built, because they care about it, you're deluding yourself. I was deluded enough to think that people would care about what we built rather than us doing more and more stuff for them continuously. Amazon really gets this. They call it customer first culture or something like that.
Amazon completely appreciates that people only care about them because they're the cheapest, the most convenient, the best at customer service. They know people do not give a shit about Amazon. They'll buy something anywhere else in a heartbeat if the experience is 1% better. We didn't appreciate that at the first company. We thought we're going to build this cool thing and people are going to want to come hang out with us and buy us beers. That was the biggest, silliest thing I ever thought. It took me having the experience of nobody caring about us and emailing us to tell us that we suck because we spelled something on the site for me to get that. “Why don't you allow me to log in with Twitter?” they’d yell at me. It's nice to know people don't care about you and then you're forced to focus on the things that are important. If you're going to run a business you should run a business, not a startup where you're doing it for the sake of running a startup.
With CollabFinder I think we learned a lot and I thought we should do build something and then every month we're going to make it better and focus on being a business and not just launching a startup and getting press and that kind of thing. We tried to do all these things. Every week we would have a big meeting. We'd talk about what we accomplished that week and we'd look at the metrics and say how do we improve 1% in the next week and this and that. How do we start bringing in more revenue? That was great. We learned a ton from that process and the product was better because of it but the idea wasn't sufficient to warrant a whole company. It became the opposite problem. Just having that knowledge of how to build something well doesn't mean what you're building is going to be great.
In other words, if You start out with a bad idea or your process is going in the wrong direction you're not going to end up successful. There's no confetti either way. To have the confetti you have to have a really good process and be humble enough to build something for other people and not focus on yourself and then also have a good business.
As a product designer how do you wrestle your time and your energy from working on products that you jreally want to work on and those that you think might potentially be a business? How do you balance the two? How do you decide what to pursue?
If you're developing a product you have to do user testing, you have to get feedback from strangers, you have to know whether or not what you're doing is working rather than just thinking it works.
I think it's learning to have a list of potential ideas that you explore thoroughly, not just working on the first idea that comes to you. I’m working on a new product now and I have a much different process for building it than I did even with CollabFinder. Every day for six weeks I would tweak this product and then I would take it out into the world and I would show a complete stranger and I would see how they used it. That's the first time I've ever done that. As a designer we tend to talk about the design process of the details a lot, but not the process of how to pick products to work on. If you're developing a product you have to do user testing, you have to get feedback from strangers, you have to know whether or not what you're doing is working rather than just thinking it works. You have to get some data behind it. It was actually the first product I built, including CollabFinder, where I would take something, I would test it in the real world and see who's likely to use it, and then improve it, and the next day repeat that process again and again. That was so incredibly fun and interesting and it makes it a lot easier to know whether you should persue an idea or whether an idea can become a business.
After trying this process out I thought: A, it's really fun and awesome. B, you actually have a sense of confidence about what you’re building that you would never have if you just trust in your gut. A lot of designers who've never done this think that's how it's supposed to work. Trust your gut. You're a designer.You're supposed to follow a gut instinct like you're a genius. Having feedback from the people doesn't mean you're not a genius, though. It just means you're smart and empathetic. For me, this has been a really interesting new development in the way I try to do products. You build something and you take the very first version that you built in an hour or two and you start showing it to people. Rather than asking them what they think about this you just see how they use it.
The three metrics I used for determining whether an idea I'm building is any good are: 1) how often do people smile when they're using it? Or do they throw the phone across the room in the first 60 seconds? 2) When I ask people to describe what it is, can they describe it? Can they describe what it is and why they want to keep using it in a sentence? And 3) Can I see by the way people are using it with their fingers that they get it. People can say all sorts of stuff to make you go away while they’re testing your app, whether they like it or not, but their fingers don’t lie. If they do the right thing in each of those things, you maybe have something that's worth spending more time on. If people very clearly frustrated with my idea, and they don't smile at all, and they want to give the phone back to you very quickly, then this is probably not something that... You have something that's definitely wrong. The biggest difference in the way I develop products now and do product development is every single day I take something, put it in front of people, and get real data from people's faces and how they use it and watch how they use.
And, in the end, you have to be honest enough with yourself to accept when something you make sucks based on that feedback. You have to be honest enough with yourself to accept the fact that changing the colors and layout and styles isn’t doing product design, its just messing around for fun. If you can’t actually change what you’re building based on how people interact with your prototyping than you’re not doing design. I futzed for years, so I know what its like!
How much does having a marketing plan or a growth plan or ideas around that play into how you design the product?
I think that's still a mystery to me. I think it sounds like a good idea to have marketing built into the product design. Seth Godin talks about building something that will spread. Why would you build something if people aren't going to talk about it and share it? If nobody talks about it and nobody shares it, it's dead on arrival. You have to design something with marketing built in in the sense that people would want to share it with their friends. The easy way to talk about this is you just put share buttons everywhere. That's the most superficial approach to that. One of the reasons that the second metric in my testing my mobile app with strangers is can you describe what this is? How would you describe it to your friends is usually how I put it. If you're going to tell your friend about this app what would you say?
If they say it's this weird app that lets you do this weird thing they're not going to tell their friends about that. Part of it is just building a product that people want and if people want it their friends will probably want it too and they'll tell them. For the most part that’s the only layer of marketing I understand, I never really know how to understand a lot of the other stuff people talk about. All I really think about is do people who use this want and if they do want it they'll probably tell their friends and that's all you can really expect. I don't expect people to Tweet their praises of these products but maybe they'll tell their friends if it's good enough. That's one of the things we measured with CollabFinder. Do people who sign up Tweet this? We make it very easy for them to do those things, and provide incentive for them to do that, which is smart. It was always a pretty low percentage though. We were like we're putting so much time and effort in getting people to talk about it rather than actually building something super amazing. That's an important metric to know. If people aren't sharing your thing on the internet then maybe it's not the right thing.
What is your design aesthetic and how do you go about designing product?
The ideal product flow in the future will be designers will code and they will prototype. There will be no designers who just take a Photoshop mockup and hand it to an engineer and say, "Add the interaction."
The ideal product flow in the future will be designers will code and they will prototype. There will be no designers who just take a Photoshop mockup and hand it to an engineer and say, "Add the interaction." The interaction is the design! People who don't see that is very confusing to me. So for the things I design, it's mostly with interaction in mind, not really the top visual layer.
Another way of putting it is like this. It's so clearly true that what color you pick for your website is unimportant. If you spend a lot of time on that, that's time you're not spending on the interaction, which is what people really feel when they use something.If they are using an app and your app is slow... As a designer, you should know it's slow. You should be using the app as you're building it and you should know it's slow before it gets released. A lot of designers are like, "Oh, I made this app," and you see them use it and they're confused by the interaction or the fact that it's slow and laggy. They didn't expect it to feel that way. And for me, that's totally crazy.
So those are the two big things. The third thing is working with the designers I’ve work with. The first designer I ever really worked with was this guy, Khoi Vinh, who's sort of a design hero of mine. This is sort of a random segue, but almost all the products I've built and the stuff I've done is just because I emailed strangers.. Everything that's good that's happened to me in my life happened because I talked to a stranger, and that's true of everybody. Everybody you meet was a stranger once, but we tend to think that strangers are weird and you're taught as a kid, "Don't talk to strangers," which may be the single worst piece of advice a parent could give their kids growing up is don't talk to strangers. Strangers are amazing. You should talk to everybody you possibly can.
So I developed this habit of emailing strangers and one of those strangers was Khoi Vinh. He was kind enough to hang out with me and have lunch, and I watched him do design and ended up doing some projects with him. And I think a lot of the stuff people see in my design they think of as a rip-off or an ode to Khoi Vinh, which I totally appreciate.
I did a website for the city of New York and somebody Tweeted, "This site is Khoi Vinh as fuck," and I thought, "Yes. I'm doing good work if it's Khoi Vinh-ish!"
The other people that influenced my design thinking are Seth Godin and one of the other cofounders of CollabFinder, Gil Hildebrand, who’s always very thoughtful about design.
That's cool. You've built a lot of products and now you've started this new design agency called Supercharger, but you're still working on your own things. How is your product design different when you're working for a client than when you're doing your own thing?
I think I try to make it the same and I think, and I think that’s because I understand that working on someone else’s good product is better than working on my own bad idea. The thing that's changed compared to when I first started doing design as a freelancer after I left Squidoo, and I did work for Myspace and a bunch of different startups. I think then I had this sort of groveling approach to design where you really want to please the client and that's the most important thing. They'll tell you they want something that way and you'll immediately do it. You may say, "Are you sure you want to do that?" You won't really push back. Now it think it's as somebody who's built products and businesses and stuff like that you get this whole experience. Part of that is actually knowing the whole design business stack. That’s one of things I learned from this guy John Borthwick who runs Betaworks.
He talks about the stack of Betaworks as software, like real-time and social, and he means it literally like the software stack has to be real-time and it has to be social, and the business has to be real time and social. He's not talking about the business stack like how we typically approach business. I think when you have the ability to go through all the layers with a stack when you're designing a product, which is the marketing, the visual design, the interaction design, the product design, the business design you're able to talk to a client in a much more useful way than just saying, "Do you like green or blue or red?" When we work with startups it's often like help us understand your business, where you want to be in five or six months. Tell us about what apps you like. Tell us about many, many things. There's many more questions that I ask now than I would when I was a freelance designer who had no experience building his own products.
Businesses appreciate that quite a bit. It also just helps me build better things, which makes me want to do it more. Whereas when I was first doing freelance design I hated it. I was spending all this time working on products I didn't really care about. I was doing design that wasn't very good. I thought this is not a fun way to live my life. Now I'm like if I really want to spend my time doing design for clients I want it to be amazing. I don't want it to just be blah, give them the cookie cutter design. This is something that I've been thinking a lot about recently, but if you're just a freelance designer you're kind of ruining your own life in the sense that you develop all the worst habits. There's this woman in New York called Zephyr Teachout. She said this really amazing thing about politics and the corrupting influence of money in politics that ties into this.
She said the problem with financing politicians through private donations means forcing politicians to spend 50% of their day calling up donors, which means they learn to grovel to these donors in power and for a human beings it's very hard to live two lives in your own head, one as a politician working for the good of the people and one as a suck up to people with money. In one life you're groveling to these people in power and doing what they want because they have the money, which you depend on. But they also be independent, cerebral people who do really good work. It's very hard to be both of those things. For her the problem of money and politics is not outright bribery. It's just that forcing politicians to continuously grovel to people who run businesses is not what you want from them. Nobody can do that. You want them to focus on doing really good work for the people alone.
I think the same thing is true being a freelance designer. If you spend your entire life being a freelance designer you develop the worst habits of design. You tend to be very superficial. You work on stuff much too quickly. You don't appreciate all the layers of the stack that you would see if you were just somebody who's worked at a startup or built product from scratch and done this research again and again. I think that's a roundabout way to answer your question but that's something I think is pretty important for us to take all the stuff we've done in our lives as entrepreneurs and business people and people who have had many hats and put it into the work we do for other companies as designers and not just do work for other companies our whole lives.
Cool. I want to come back to something earlier that you were talking about. You said that you can never not work for yourself again because you always have all these ideas. How do you ultimately choose which idea that you want to work on or how does it choose you?
Just working for yourself is not enough. Working on something important and good is best. If you can, the ultimate best is working on your own, a person that's very good and very few people can do that.
I think the thing about not working for other people is just really that, well I think one thing is definitely true. It's much better to work on somebody else's good idea than your bad idea, as I said earlier. I have a lot of respect for people who have that sort of wisdom and can work for other people and do good work. I think I've learned that over the years. Just working for yourself is not enough. Working on something important and good is best. If you can, the ultimate best is working on your own, a person that's very good and very few people can do that. I think that's one of the reasons people love working at Google is because they're working on really good stuff rather than just stuff. I think that's a really important part of people's live, working on something that they respect. For me that's one of the reasons why I'm trying to do both at the same time, to work on good ideas from the people and also having the experience of trying to build something from scratch on my own.
The process for, I think, picking which products to work on is really just saying being able calculate the opportunity cost of not working on your own stuff. Can you actually come up with a good quantifiable opportunity cost for your life? If I'm not going to work on my own stuff because any number of reasons what am I actually missing out on? If you can't actually pinpoint the things you're missing out on then why worry about it? What I try to do is make a list of things that I think I would really be missing out on if I wasn't working on my own stuff. When I have an idea for a new product I spend an hour tinkering with it, building it, prototyping it, and then just taking it out into the world and showing it to people. And if someone feels like a really good product and something people really respond to positively, then it becomes a real opportunity cost. If I'm not doing this, I'm missing out on something really interesting.
So whenever those things come along, I try to actually work on those for a month. Is something coming out of this that's positive? Is this the kind of thing that I can actually do? Maybe it's a good project and I'm just not the right person for it or maybe it's a good idea and it's ahead of its time. There's any number of things that can derail an idea but learning how to quantify it makes it so much easier to know whether you should be working on something or not.
Thank you very much.