Episode 46

Designing for everyone, everywhere with Luke Wroblewski

Our latest Overtime guest, Luke Wroblewski, is known best for humanizing technology. He’s the author of several web design books, has founded several start-ups that were later acquired, and he’s now the Product Director at Google.

When I look back on the things that have been the most interesting that I've done, I really liked the web because I thought the web was extremely empowering in terms of the things it brought to the planet. The sum of human knowledge available via web browser on any desktop, that kind of thing. Instantly type a word and you're off to god-knows-where.

In this episode, Dan and Luke discuss the key ideas behind his book Mobile First and how that translates to building for devices today, why we should be data-informed, not data-driven when it comes to building products, and what he learned from his time creating and building Bagcheck and Polar.

This episode is brought to you by Wix. Push the limits of design and start creating beautiful, impactful websites that are uniquely yours at

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Luke: Well, I would like to welcome you to the show. It’s so great to have you here.

Dan: Thanks.

Luke: Thank you for making time.

Dan: Thanks for having me Luke. Appreciate it.

Luke: Yeah. You know we’re gonna keep it pretty casual today. We’ll decide what to talk about as we go. So just hang back. Have some fun.

Dan: Love it. This is staying in by the way. This is actually the beginning of the episode. We’re gonna use that.

Luke: Yeah. Perfect.

Dan: Yeah. And welcome too Luke. We go way back, for many years.

Luke: Mm-hmm

Dan: But it’s been a while since we’ve seen each other. I’m really glad to have you on the show. I don’t know. There’s so much to talk about here because your career alone has kinda taken on many stages. I’ve just always admired you’re speaking and your writing, your entrepreneurship; you’ve just kinda got all these things going on.

Luke: Well thanks. It’s all kicked off from a bullet proof CSS so thank you for that.

Dan: Yeah. I’m sure that was the–

Luke: That was the tipping point.

Dan: That was the tipping point for you?

Luke: I mean in all seriousness I did use that.

Dan: Aww, man. Now you’re too kind. That’s awesome. And likewise, you’re … back in the day when I was still talking able to talk about CSS because I was able to keep up on it, we spoke at a lot of conferences together and I was just always … you’re still doing this. You keep track of, specifically in the mobile world, you keep track of UI and data and trends. I always think in the back of my mind like okay, what would Luke do here? And what would he think about this? How do you keep on top of all of that stuff? In addition to all the other things that you’re doing.

Luke: Yeah. I mean I think it boils down to staying very curious. Right? So I’m still pretty excited and interested in it. So I naturally have this inclination to stay on top of stuff. But then I had this moment … I set up one of these hunting trail cameras, I don’t know if you’ve seen these things, but you … it’s got some motion sensors, right? And a camera and you set it up in your yard and it catches the critters that go by and these types of things.

Dan: Oh yeah. Yeah.

Luke: So I put it up over the weekend. We left for the weekend. And I came back and it only had one video on it. There’s a pretty good video of a whole bob cat family but that’s beside the point. My first reaction was to blame myself. I’m like, “Uh, there’s only one video on here. I must have done something wrong. I gotta tweak the settings. What can I do better next time.” Right? And my wife was like, “Oh well maybe the bob cat family scared off all the other critters.” So it just stuck in my head this sort of like contrast between how I think about things and the way she thought about stuff. ‘Cause my first inclination is, “what else should I do? How much more should I change? You know? What am I doing wrong?” I just jump right into trying to figure something out. And that’s kinda my natural inclination to everything.

Dan: Yeah.

Luke: Which is why I think I stay so active and interested in stuff because I’m always blaming myself.

Dan: Yeah. So that’s a good thing. Keeping yourself curious.

Luke: Yeah. In some ways.

Dan: I’m resisting going off on a complete tangent with the wild life camera. I really want to do that. That’s fascinating to be honest. I think its … so it picked up bob cats but nothing else. So you’re thinking, “What the hell’s wrong? There should be a whole bunch of critters on here.” And then your wife’s right, that’s probably what happened. Because they’re kinda at the top of the … near the top of the food chain.

Luke: Yeah. Maybe they scared off everyone else.

Dan: Yeah.

Luke: You know, I’m still not buying that. Me per– I already went in and changed like 5 settings. I readjusted the camera. I already burned an hour or two on this.

Dan: I love it. And I’m not surprised because you seem to take that approach with things. So you’re still enjoying keeping a pulse on tech and mobile and wearable and all that stuff.

Luke: Yeah. I mean when I look back on the things that have been the most interesting that I’ve done, I really liked the web because I thought the web was extremely empowering in terms of the things it brought to the planet. The sum of human knowledge available via web browser on any desktop, that kind of thing. Instantly type a word and you’re off to God knows where.

Luke: I feel like mobile takes that to 11. Because now all that stuff is with you anywhere and everywhere; for better and worse. I mean there are some good and bad parts to that. But right now we’ve got something like 7.6 billion people on the planet and 3.5 billion depending on how you count 3.7 billion smart phones.

Dan: Wow.

Luke: And so that’s a very planet scale type of thing. And there’s about 5 million mobile devices period which will ultimately become smart phones over the next couple of years here.

Dan: Wow.

Luke: I don’t know if there’s ever been anything that reaches that many people with that much empowerment. So I just have this passion about making sure that it doesn’t freakin’ suck. ‘Cause if you’ve ever used the internet or used software you know pretty quickly the places where it can really really suck.

Dan: It really does. It’s not great everywhere. Right?

Luke: No.

Dan: That’s a lot of people using … connected. That’s interesting because at the beginning of the web, I was the same way. I was fascinated by the fact that you could publish something and it’s out there for everyone to see. But it’s not really everyone at that point. But here we are with phones and the barrier to entry is much lower for people.

Luke: Yep.

Dan: And that’s exciting too. I remember when mobile was a different mindset of design. Okay, now let’s think about the mobile version. This is going way back by the way.

Luke: Yeah. Well, not that way back. Right?

Dan: Yeah. I guess it wasn’t that long ago.

Luke: Less than 10 years for sure.

Dan: Yeah. That’s true. It feels like forever. And now we’ve come a long way with I guess with responsive design and apps and everything sort of culminating. What’s the one thing that you’re most excited about I guess with where things are going. Where they’ve come over the last 10 years.

Luke: I always, and maybe this is a detriment or maybe this is a benefit, I’ve always been obsessed with the things that hit everybody and are bad. As opposed to things that just hit a few people and are good. For example, for many years, if anybody’s heard me talk I’ve talked about things, let’s log in forms, and check-out forms, and things like that. And those things seem trivial and it seems like, “Yeah, we know how to do that. You put the user name, the password, the checkbox that says stay logged in, that doesn’t do anything and you’re done.” And that’s how everybody approaches that type of problem. When you actually look at the statistics, and I’ve had the benefit of being at some of the largest internet companies in the world … the Yahoos, the Ebays, and now the Googles … I get the pleasure of seeing that actually data and just realized how much human misery at scale these things are doling out.

Dan: Yes.

Luke: To be totally honest, you don’t really need those mega stats to know that. You just have to see yourself or a family member, anybody struggle to get into their bank account or to get access to the picture gallery from their kids school, or whatever it happens to be. Every single day you can see people really struggling and just having terrible experiences getting to the stuff we’re building.

Dan: Yeah.

Luke: And so the things that excite me … and it’s been such a hard path, is something like, if you look at face ID, on the I Phone. The way it treats passwords is like, look, I see you, you’re you, okay you’re in. Which is how the real world works. If you owed me five bucks and you see me and you’re like, “Oh hey, Luke, here’s that five bucks.” The way you authenticate me is by recognizing me. And so I think it’s an awesome example of technology bending to the way people work as opposed to making people bend to the way technology works. The way technology works has a name value pair, stored securely on some server, you have to enter it, it has to be eight characters, special characters, all this stuff, so it can’t be hackable. And it puts the whole burden of all of that on you the human. As opposed to doing all the hard work so you can just act like a human as opposed to acting like a machine.

Luke: That’s very encouraging to me but at the same time it’s sort of discouraging because when this stuff came out I was super excited about it and I’d go online and try to find other people talking about it in this way and what I find is a bunch of web designers complaining about the notch. And the impact that it has on the layout of their web page in landscape mode. To me the notch is a freakin’ connect sensor shrunk down to the size of your smart phone. It does like 3-D mapping with 3,000 points of depth to recognize your face even when you wear glasses, you grow a mus– I mean it’s amazing stuff, right?

Dan: It really is. The speaker too.

Luke: Yeah. It’s stunning what you can do with this. You can solve terrible things like login and passwords. But the debate is around what a web page layout looks like in landscape mode.

Dan: Aesthetics.

Luke: Yeah. While we have all these advances I just don’t feel people look at them as opportunities because we’re so … I don’t want to use the word stuck, but you kinda get into your mode of operation and you stay there. And you think about things like how do I layout this page and therefore things become issues of layout whether you consciously know that’s what you’re doing or not.

Dan: Mm-hmm I love it. You’re right about the notch too. It is kind of amazing what’s possible in your pocket right now.

Luke: Yeah.

Dan: And the fact that we’re complaining about anything is kind of amazing.

Luke: Yeah. And not just that, like A, 95% of viewing on smartphones is in landscape mode anyway. Right? Sorry, portrait mode anyway. So complaining about the landscape thing is not–

Dan: No. Not it’s not.

Luke: I guess I’m not a “get off my lawn” kinda person with that. I don’t want to sound too angsty right? Or ranty. But I just wish more people would kind of take the broader view on some of these things. Because we still have so much to improve and we got 3.7 or 3.6 whatever it is, billion of these things active so you just fix things a little bit, like you’re doing a lot of good. Right?

Dan: Yeah. And like you said, you’ve had the advantage of being at large companies where you can see the data on this stuff. And that’s what I really appreciate about your work too is that you’re constantly sharing the data on patterns and on how this stuff can be improved. How did that start for you? Was it just … where does that come from?

Luke: Good question. The first big internet company I went to work for was Ebay in like 2001 or so. And the way Ebay worked is they had this notion of train seats. And a train seat, I know this is going to sound like wizard language but just bare with me for a second.

Dan: I like wizard language.

Luke: Thank you. So train seats … I would explain this, I went back to Ebay a number of years, many many years after I worked there, and I started explaining how things used to work and I paused myself and I said, “I’m sorry, that all sounds like gibberish wizard language doesn’t it?” Now I can’t stop thinking of it like that.

Luke: But there was this concept of a train seats which was like a unit of development resources. And so projects would say, okay this project costs 10 train seats or 20 train seats. And in order to get those train seats which was the people you needed to do what you wanted to do, you had to make a case for it. And the way you made a case, there was a thing called an NPV, net present value, and there was a spread sheet and you sort of filled that in, what numbers you thought you’d move and how much. And out would pop a number that would say okay, this project is valued at this many train seats because we think you’re gonna have this and this impact. And every single project ran through that formula.

Luke: So as a designer going in there it just sort of forced you to think about what is impact of this going to be. It made it very hard to do things like redesign the settings page because it was crappy because you could never make the numbers work. But it did instill this mindset of accountability and awareness of both what your work could actually achieve and how you should discuss and frame your work to other people. Because the bottom line is everything costs something. It costs time, it costs money, whatever. And if you live in a bubble and you pretend that doesn’t happen it’s really hard to convince others to take you seriously. Because they’re like, “Oh yeah. We can make that pretty but do you understand that I have a company of 10,000 people to run and there’s 120 million users on the other side that are trying to do x, y, and z.”

Luke: So I think that’s where that comes from. It just got ingrained in me there. And it was just such a part of the culture for better or for worse that I think a lot of people that worked there walked away with that mentality and that approach.

Dan: So you really had to diagnose that you have something you want to do. You really had to look at data, research backup your idea with some logical stuff. Right?

Luke: Yeah. You had to frame it in that. For example, the spreadsheet was like each new person who registered is worth X dollars. Each time somebody bids that’s worth Y dollars. Each time somebody makes a purchase it’s worth Z dollars. And so you just sort of estimate and start thinking about what kind of impact am I going to have and that translates into money which then translates into train seats.

Dan: Wow. I’m impressed that this was going on in early 2000s. Right? In internet years that’s pretty early on.

Luke: Yeah. There was a lot of disciplinarians there. I think they had had a really big crash in the late ’90s.

Dan: Right.

Luke: That scared the hell out of people. So a lot of very ops oriented folks were brought in to drive these big big changes on how things worked.

Dan: Mm-hmm

Luke: And again everything has some pros and cons. So there’s some really good things that happened there but there were some negative consequences from that.

Dan: Yeah. Sure. So from Ebay, what was next for you after that?

Luke: Well it was at Ebay that I wrote that book on web form design.

Dan: And I remember that fondly.

Luke: I’m sorry.

Dan: No. I really … I loved it. And I thought it was amazing and I thought it was so valuable that someone, you, took the time to focus on that because it’s so critical. I learned a lot from that book.

Luke: Well thanks.

Dan: Yeah. I really did. I think it’s one of those things where, as a visual web designer, it’s like sometimes forms for me were always like, “Oh shit, I gotta do a form again. I hate to think about forms.” You took a lot of the guess work out of how you should lay the forms out and how they should operate. So I thank you for that. That was really valuable.

Dan: … It should operate. So I thank you for that, that was really valuable.

Luke: Well I’m glad to hear it. A lot of that came from exactly what I was talking about at Ebay, right? Just quantifying stuff. And the big takeaway I had from that whole point in time was, “Hey, the way we talk about this field, the way we build the field, the way we do error messages, the way we do all of this stuff, it just has such a huge impact.” Right?

Dan: Yeah, it really does.

Luke: You could see these swings. And it wasn’t just swings in terms of money and user activity, because Ebay at the time was something like the 28th largest economy in the world. So you could see these swings, and it was like how people can actually live their lives, second businesses, make themselves independent … And you had an impact on that based on design work you did. And it wasn’t just a small impact, right? Some of these things were like massive impacts.

Luke: So that’s really where I got a lot of the inspiration and a lot of the learnings for that book, was through seeing what these UI affordances at that scale can do, and just trying to get that appreciation and respect. Respect might not be the right word, but like, awareness of, “Here’s what your discipline actually does.” And it’s not just picking a color, right? It can go a lot deeper.

Dan: Right. Definitely. And for people that aren’t working at the Ebays and the Googles of the world, what’s your recommendation on doing that same sort of thing with your own UI that you’re working on? If that makes sense.

Luke: Yeah.

Dan: In other words, if you don’t have the data of a Google or Ebay, is just the data from your existing audience enough, or do you tend to pull in from other data sets somehow?

Luke: Yeah. So I have a mental model around this, which is, how do you make decisions? If you have no information, then you’re sort of like in a whole looking up … You can’t see the world, you don’t know what’s around you. So you’re making decisions based on not very much insight or information, because you’re down under here. Every little bit of insight you get … This is kind of the metaphor I use. It sort of lifts you up a bit. You can see more. Right? And not all of that information is data at scale. That’s one kind of information. Other information could be just watching people do things. Other kinds of information could be running a little usability test, or a remote thing, or doing a survey. There’s so many different ways to collect information if you will, and the more information you collect, the higher you raise your plateau of decision-making, and the more you can see. So if you’ve got a lot of information and insights, when you make a decision you make it much more confidently because you can see for miles, as opposed to just seeing like two feet in front of you, or whatever, because you’re in that hole.

Luke: So I don’t think it’s like only one kind of data, or one kind of information that gives you that lift. In fact, it’s the opposite. If you only have one kind, you don’t really get that much of a bump, you just go up like one level. So you really need a lot of diverse types of insights. And some of those insights aren’t even data, they’re experiences you have. Go out, travel the world, see how different people do things, try different stuff, talk to people who are really deep in other things … All of those things together cumulatively start to raise your plateau of awareness of what you’re doing and how you should be doing it.

Dan: Yeah. I totally agree with that, that’s wonderful.

Luke: Yeah, so don’t be scared if you don’t have ‘big data,’ because big data sometimes actually is paralyzing, right? Like, “Oh my God, one million people did this! What does it mean?” You don’t know until you go talk to somebody, “Oh, you thought that button said ‘taco’ instead of ‘burrito.’ Oh, I get it.”

Dan: Right. Yeah, and at a certain scale, one million could mean very little, right?

Luke: Yeah, it could be a browser bug.

Dan: Yeah. Right.

Luke: And I’ve seen that, right? I’ve seen these really weird changes, and you spend months scrambling around trying to figure out what happened, and you realize, “Oh, that’s because … In Firefox.”

Dan: Which is totally not related to your UI decisions or whatever.

Luke: No, there’s so many variables and factors, again, which is why just looking at this quantitative data is not nearly enough. You need to look at it from a lot of different angles. And the other thing that I hear a lot of people say is, “Well, we’re a data-driven company.” Right? “We use data to make decisions.” And I think that’s scary as hell, because then you can be like, “Well, the data made me do it.” Right? “Why did you do that?” “I don’t know, the data drove me.”

Dan: I want that on a t-shirt, “The data made me do it.”

Luke: The data made me do it. Yeah. But if you’re data informed instead, right? Then you’re still the one making a decision. The data is there to help you get that better vantage point, or understand the situation more or whatever. So it’s a small change of words, but I think it has a really big impact on how you approach stuff. Like, AB testing is another very common thing. Right? “Oh, we AB tested that, and the blue button wins over the green button.” Okay, so this AB test runs your life. Right?

Dan: Right, the green button is terrible, we’re never going green again.

Luke: Well everybody in the company is like, “Okay, that hot pink button with the unicorn is terrible.” But it converts better!

Dan: Right, so there is a danger sometimes of just relying only on the data. I find that … Most of my work is just from the gut, and I don’t know whether it’s laziness or I’m just not smart, but I find that the times when I do use data, it helps me sell the thing that I’m trying to change or introduce. Which is helpful. So in other words, maybe I’ll say, “Okay, I believe we should do XYZ,” and then if we can run a test and the data backs up that, then it’s easier for me to sell that to somebody rather than just explaining that we should do this …

Luke: Well it’s another kind of consideration, right? And what happens in that conversation, both of you walk away a little bit more informed. You’re like, “Oh, it turns out most people do this.” Okay, well that changes … It goes away from just my opinion versus your opinion, to, there’s another piece of the conversation there. Which can be very, very powerful and useful.

Dan: Absolutely.

Luke: Yeah. Like I said earlier, as with everything there’s pros and cons. All right? You go too far to the extreme, the data made me do it, you go too far in the other extreme, you may be missing stuff or unaware of very bad things that are happening because you’re not looking at any information.

Dan: Right, it’s all a mystery.

Luke: Yeah. Or, you just may be totally unaware of huge bugs or usability issues or whatever that are plaguing your site, because you look at no data or information, or … I don’t think anybody really lives in that world, because somebody will come and yell at you. I hope. If not, then what you’re doing really doesn’t matter. So don’t worry about it, you’re fine.

Dan: No, if no one cares … Right.

Luke: Yeah. No one cares, you’re good.

Dan: Yeah, you’ve got other problems.

Luke: Yeah.

Dan: So I want to talk about, too, Mobile First. And this is a book you wrote for A Book Apart … Very seminal work in terms of mobile design. Again, another book that’s super helpful, so I thank you for writing that one as well.

Luke: Well thanks again.

Dan: Yeah, it’s super great. Do you feel like … How long has it been? This was a few years ago that Mobile First was published, right?

Luke: Yep.

Dan: Okay. Do you feel like … What’s your current take on that in terms of believing that Mobile First is the right way to go, I guess is what I’m …

Luke: So there was three parts to that. One was, “Hey, mobile is really gonna take over in terms of time spent use in devices.

Dan: Yeah.

Luke: Pretty confident-

Dan: Boy, you were right.

Luke: Pretty confident in that one, right?

Dan: Yeah.

Luke: The second one was, working for the small screen forces you to prioritize and rethink, and get down to some of the core basics of what you’re trying to do as opposed to cramming all of the stuff you’ve been-

Dan: Yes.

Luke: For so many years.

Dan: Yes. Yeah, love that.

Luke: I love it too, but I still think it’s really hard for a lot of people to do. Right? So I don’t necessarily see that mobile has led to a world of much more simplification. There are definitely services that have done that, which have thrived on mobile. Right? And many of them have not necessarily been ports of existing experiences, they’ve been new things that have bubbled up, like the Instagrams of the world if you will. Right?

Dan: Right. True.

Luke: That’s a nice example of that kind of thing.

Dan: Yeah.

Luke: And then the third one was, “Hey, these devices have all this crazy technology. We really should be using this instead of just relying on form fields and buttons, and what have you.”

Dan: Right.

Luke: And there it’s a bit of a mixed bag too. A lot of that technology is available, and you have really amazing things like the Lyfts and the Ubers of the world if you will that use your location, and where other things are, and paying with your thumb print-

Dan: Right.

Luke: And all that. There’s certainly things that have really pushed that envelope and done great stuff with it. But then again, you still have all this stuff that’s just ported over and never even thinks about it. Right? So also a bit of a mixed bag there. So cumulatively, out of three, maybe it’s like 1.4.4, something like …

Dan: Yeah.

Luke: 1.8 out of 3 or something. Not too bad.

Dan: Yeah, and I love your second point about, whether you’re designing … You take a device out of the picture and try to simplify your UI and your product that way. I think it’s brilliant, and I think that’s, like you said … That one’s harder for the greater public to grasp, but that was a big takeaway for me in terms of … And I think it goes along with responsive design as well, where you’re … Does this work in a small screen versus a medium screen, versus a large screen or whatever it is? And one easy way to do that is, let’s simplify it so that it does work perfectly on the small screen, and then go the opposite way. Start there, and then expand as the screen gets larger. I think that was really … That’s just a really important viewpoint. So thank you.

Luke: Yeah, what it does make me think though is, there’s these legacies, right? So the whole notion of layout, if you go back to a lot of things that we’ve been talking about here, whether it’s the forms or the mobile design, or some of these new opportunities, right? The notion of the layout permeates so many things. Because when we talk about making things work on mobile, a lot of people’s approach is, “How do I make it look good?” And then I make it look good on the next screen, I make it look good …

Dan: Right.

Luke: And they’re still in this kind of layout mentality. And don’t get me wrong, right? Making things look good viscerally, aesthetically, brand, all that good stuff is great. Having a good personality, making things attractive, I love it. But, when that is your core consideration, I think the trouble a lot of people have is shifting from that mode to this mode of, “How do I get people the right things at the right time?” Which is a different mode of layout, right? It’s not, “How do I fit all of these things on the screen to look good,” it’s, how do I bring in things at the appropriate moment so that they’re contextually useful for people based off the tasks they’re trying to achieve, and they guide people to what they need to do next, and how can they actually achieve their goals? And that’s this mental model, this approach switch, and I think a lot of people struggle to make that leap, if you will.

Dan: Yes. Exactly.

Luke: It’s still ‘layout,’ but your mode of approaching it differs, because you’re really focused on the person’s task, and enabling that, and making it more efficient and what have you, versus just trying to fit a bunch of stuff in an appropriate way on some kind of canvas.

Dan: Right. It’s like we started trying to replicate magazine and newspaper-

Luke: And still do, right?

Dan: Layouts. Exactly. And that might not be the right approach for every experience, right?

Luke: Well certain things force you to get away from that. Although voice interactions have their own issues … There’s an example where you really have to get out of it. Right?

Dan: Yeah.

Luke: We stretched the whole mobile first idea pretty far with a startup I did a little while ago where what we did was, the first thing we built was an API, and so the first user interface for the product was a command line user interface. And it was awesome, because it really forced you to think about the object and the actions, and how are they inter-related, and what sort of sequences and steps, what are the options in those sequences and steps … Because you’re basically making a Planet Fall. I don’t know if you’ve played Planet Fall or any of those kinds of text-based adventure games …

Dan: Yeah, sure. Right.

Luke: That’s the kind of UI you were doing.

Dan: Yeah. That’s the UI.

Luke: So a ‘know UI’ approach to your UI just naturally makes you act and work like that, as opposed to biasing you with the things that wire frames make you do, like layout boxes, right?

Dan: Yes. Exactly. Well this is brilliant. So was this Polar?

Luke: This was Bagcheck.

Dan: Bag Check. I’m sorry, that’s right. So Bagcheck, right. And I remember this, and this was … You were later acquired by Twitter, is that right?

Luke: Yeah. Got it.

Dan: Yeah. So if you started another product like that, would you start with the API again?

Luke: I think it depends on who I’m doing a project with. Right?

Dan: Yeah.

Luke: Because you kind of have to have a partner or a collaborator on the engineering side who is also interested in that type of thinking.

Dan: Yeah.

Luke: Not everybody’s brain goes that way. I had an awesome co-founder, Sam Pullara there, who, credit to him, he basically just started making an API, because he knew we were gonna need an API eventually.

Dan: I see. Right.

Luke: And then the two of us just gradually started building the product based off of that. Right?

Dan: That’s great.

Luke: And for a bit there he actually was asking me for pictures … And I’m like, “No, hold on, this is actually working better. Let’s not make any pictures, let’s just continue down this path.” And a really funny story, which maybe I shouldn’t say publicly, but screw it … Our CO at the time was Bryan Lamkin, who was an SVP over at Adobe, and he was the one responsible for bringing over Macromedia and Flash to Adobe.

Dan: Oh wow. Yeah.

Luke: So we had built this text-based API version, this command line version of the UI, and one of the things that we were doing was entering information into this system. And during his downtime when he was in the office, he was entering some of this info of his command line interface. And he would go and hit Flash pages where he couldn’t just copy and paste text, because it was all flash, and you have to manually type it out. And I always thought of that as a pretty interesting-

Dan: Yeah.

Luke: Reflection of fate, right?

Dan: Yeah.

Luke: Yeah.

Dan: Yeah. Right? Flash. It was destined to … Yeah.

Luke: That was one of the big things about Flash, right? You couldn’t get to the content, right? Because it was all just locked objects.

Dan: Yeah.

Luke: And then you see first-hand how much of a pain that is when every single day you’re encountering those trying to … Put them into a command-

Dan: I just want to copy and paste, man.

Luke: Yeah, copy-paste this.

Dan: That’s, oh man, flash.

Luke: Good times, good times.

Dan: Good times. It had its place, but unfortunately, rest in peace. That’s awesome. Starting with API … I love getting as far as you possibly can without even thinking about boxes and layouts and brand, and it’s sort of like what does this functionally do, right, first?

Luke: Yeah, totally. And that was a really cool way of doing it, because it actually did things, right?

Dan: Yeah.

Luke: It did have, and the other part that was interesting about it, you sort of had to associate actions to objects. Like okay, I have this object, what can I do to it? What does it do? And how does it relate to the other objects? Is it a child, is it a sibling, is it … Who knows? So it just made you think about the stuff that makes up your software in a different way.

Dan: Yeah, I was going to say, like your database is probably far less like database re-jiggering, right?

Luke: Mm-hmm.

Dan: Going that way, rather than … without even realizing you need to change the model and-

Luke: And at the end of the day, the right thing was everything ended up being an API, so that made making front ends a lot easier because you don’t have everything tied to one front end, and you end up with business logic stuff inside of that front end, and like-

Dan: Right, right.

Luke: So that was another big benefit too. You could really churn out, once you make the command line UI, you’re like oh, let’s make a web UI, let’s make a native app UI. You build it all on top of the same thing.

Dan: That’s great. And Twitter acquired that. And then what happened from there? What did they end up doing with it?

Luke: Well, Sam went over there and we had to, as part of building that, we had done a bunch of things, or he had rather, done a bunch of things from a technology perspective. And if you recall when this was, this was like what, four, three, I don’t know, seven years ago or something like that. So that was the days of the fail whale?

Dan: Oh, sure. Right.

Luke: And there was a lot of need to get rid of the fail whales, if you will. So a lot of the systems we had built really went into addressing some of those things.

Dan: Aha. So we have you to thank-

Luke: Oh, not me.

Dan: … and Sam, well, Sam. We have Sam to thank for fixing Twitter.

Luke: Well, that’s an exaggeration, right?

Dan: I mean historically.

Luke: He certainly went there and worked on some of the problems for a while, yeah, and stayed on it.

Dan: The fail whale was pretty common for a long time.

Luke: Oh, yeah. Yeah. People think that-

Dan: It was just one of those things you put up with at the time, so it was a big deal to fix that. I mean, it’s kind of amazing to talk about the scale, how they’re handling that, like-

Luke: Oh, yeah. Today’s systems are so much better. Actually, i can’t remember ever seeing the fail whale on Twitter in the past. I don’t know, maybe they got rid of the whale, actually.

Dan: Well, I was just thinking that too. Yeah, I haven’t really seen … I mean, hats off to them for that, right?

Luke: Yeah. That’s been a while, right?

Dan: Yeah, and obviously they’ve grown and grown and there’s just more being posted every day to it, so I can’t even imagine. Okay, so that was Bagcheck, and then there’s another start up you did called Polar. And that was acquired by Google. And I think this is how you got to Google, where you are today, right?

Luke: Yep, which brings us to today.

Dan: That’s right. See how this is all the story. The story of Luke. Tell us about Polar and how that story went.

Luke: What we were trying to do there was I had observed in a bunch of places where people were hacking at the tools they had to try, and get other people’s opinions, and so I would see things like my wife texting her sister, “This dress or that dress?” Right? And I just saw a bunch of those types of things happening, and said okay, there’s got to be a better way of doing this.

Luke: So we started out, it was this very social, like I just want some quick opinions, and how do we make it as fast and easy as humanly possible to get those opinions. So we didn’t really do any text based questions or any of those kinds of things that you would associate with a typical survey. We really tried to be, as an example, things that suck, right? Given a survey, how happy are you? Not happy, right? You don’t want to fill out that survey. It sucks. And those days haven’t changed over the years too.

Luke: So we’re like, okay, people do want other people’s opinions, obviously. We are those types of creatures. But the ways of getting those opinions really, really bite, so can we do better? We addressed that and we took this mobile centric approach, saying well, what does the mobile device do? Well, it’s got a camera, right. It’s got audio, it’s got all these things, and we sort of landed on these visual poles where it wasn’t like a form type thing, it was this or that, this picture or that picture, or something with really lightweight interactions, and tried to optimize how quickly it took people to make a question, and how quickly it took people to answer a question.

Luke: So I posted some of these videos. What we literally did was one hand, one thumb, and in under 30 seconds you should be able to create a question, get images for it and post it up to get … If we couldn’t hit the 30 second bar, right, then we weren’t doing any better than anything else out there. And that was what drove that. And we started with this friend to friend stuff, but ultimately what we actually learned was, because people were so quick at answering these questions because they were so lightweight and easy, we found that we would get a ton of volume when we posted a question. There was this aha moment where I put up a bunch of questions between Apple’s old icon and new icon, when they did iOS7, and I just did all these posts to this icon versus that icon, and we ended up getting a million-

Dan: Yeah, I remember that. That’s amazing.

Luke: … we got a million comments, or a million votes, right, within a day or two. So what happened was a lot of tech press wanted to post those results and put them up on their pages because there’s a million people’s opinion on which icons were better or worse. So at that point we realized we should really shift to enabling some of those use cases. What I mean by that is, allowing a site like, okay, this sports website is asking who’s going to win this game, well why don’t they just put the question right then and there? Or who’s going to be the better QB in this game, or what have you.

Luke: So we moved from running this singular app where people would go and talk to their friends only, to putting these things in context. We were going down that path and that was when Google came in, said they were doing similar things. And it’s been fun to see, actually, a lot of people’s interpretations of this simplified visual survey idea, because Twitter’s got polls now, right? Instagram did it not too long ago, Amazon has them, Facebook. All these companies. So it’s been cool to see, not that we were necessarily the drivers of any of these things, but that many people had this notion that there’s gotta be a better way to hear what other people think.

Dan: Yeah. But in a quick way of being able to generate it and vote, right?

Luke: Yeah. Again, making a survey sucks, taking a survey sucks,

Dan: Yeah, you made it fun and easy and quick. I can see, and i remember the Apple icon post, and it was perfect. It was like the planets aligned.

Luke: Yeah. That was a good use case for us. So they just need to redesign their icons all the time, and we’re good. Which, thankfully, they do.

Dan: They do. They do, actually. Yeah, that’s the thing. There’ll be more coming. Now you’re at Google, I have to mention, because I follow you on Instagram and whatnot, and you’ve been building, this is a side project, or maybe it’s not a side project. Maybe it’s your main project, but building a bike track on your property, right? It’s been fascinating following that because, well, for many reasons. Tell us about that. How did that start, and how do you balance that with everything else you’re doing?

Luke: Well, the thing I always think about that project is how much it mirrors every other type of project. The way a lot of people approach things is I get these emails and they’re like, “Hey, can you help me make this app? I want this …”. And what they see is the end state, and they don’t recognize all the things that go into it. So there’s a bike track that I built in my yard. It’s a two year project, and if you count how long it actually took us to find a property where it was possible, and it was just this niggling notion in the back of my head, then it’s a four year project. So it was two years to find the property, right?

Luke: We finally got a property where this was possible. And that wasn’t the only consideration, but it was always top of mind for me. Then it took me six months of trying to find a crew who could actually help me build this thing, so I was on LinkedIn traversing people’s job descriptions, and finally I got ahold of some guy in Scotts Valley who came out, who connected me with some other guy, who connected me with a crew in Colorado, who came out. Then we had loose ideas of what we wanted to do, we sketched things out, we gradually built it. After we built it, a whole bunch of rain fell and destroyed it, so I was in maintenance mode for a number of year.

Dan: Oh, no. Aw, geez.

Luke: It actually reminds me of building a product, right?

Dan: Yeah, I was going to say it’s very similar, yeah.

Luke: It’s totally. It’s 100% like that. As soon as you launch, that’s when the hard work begins, right? Woo hoo, we’re done. Oh crap, it rained and how I gotta go pound dirt for two weeks.

Dan: And also like finding the right people to work with, right? I mean, it comes down to that sometimes.

Luke: Totally.

Dan: You have this vision you want to do, but you really need the right people that get it to help you build it.

Luke: Yeah, absolutely. It’s so many parallels, right? Exactly. You have this vision, and as we were talking about earlier, would you do this API thing again? Well, it really depends on who I’m working with, right? And the people matter so much, you gotta allocate time to find the right people, no matter what kind of project you’re doing, because they have to align with what you’re trying to do, they probably need to bring some core skills that you don’t have, or they should bring core skills that you don’t have.

Luke: To give people a little bit of context, this is what they call in the bike industry a flow trail. It’s almost like a downhill roller coaster-y thing. Really big banked turns, jumps, and things like that. The ideal state for something like this is you can ride it down without pedaling and without brakes-

Dan: Ah, I see.

Luke: … so there’s a lot of geometry and physics involved in getting [crosstalk 00:48:29].

Dan: You only go downhill on it, then.

Luke: Well, there’s a climbing trail back up to the top, yeah, but a big chunk of it is this downhill piece.

Dan: Ah, okay. Cool. Wow, this is even cooler than I thought.

Luke: So what you have to do when you actually build it, you sketch out a line, “I’d like it to do this,” but you build a little, you have to ride it, you build a little, you have to ride it, so you maintain that “flow” going through the trail. That means altimeters, checking the elevation, the slope, that means a lot of hand shovel work to get the angles right.

Dan: Like an engineering project.

Luke: Oh yeah, it’s a crazy engineering project. Totally. It gets built by the foot. There’s a lot, and again, parallels with real work, right? There’s people’s notion of oh, it’s just a bike trail, right? What do you do, rake out some dirt. And then there’s the people who know what they’re doing and they understand all the nuance and the subtlety. And the end result is a totally dramatically different thing.

Luke: I think again, coming back to the parallels, because this is what goes through my head, those are the people you want to work with and learn from, right, because they bring an appreciation and understanding of things that you probably don’t have, and they expand the way you look at a problem, and the end result usually turns out a heck of a lot better when you find people like that to work with.

Dan: So true. So true, and I think that it’s always great to keep in mind when you’re up against something that you have the urge to build or create, and you don’t really know how to get there, often the answer is people.

Luke: Oh, yeah.

Dan: Getting people involved that can help you do it. Everything you just said there, it brings a new core skill to it and all that. So crucial.

Luke: Like when I was trying to make web pages, and I picked up your CSS book, right, to bring it all the way back to the beginning. Bringing in people with core skills I didn’t have, so I can level up a bit. Full circle, full circle.

Dan: Yeah, man. I owe you. Do you have a podcast, by the way?

Luke: This is it. Didn’t I welcome you to it earlier?

Dan: That’s true, you did. It’s now yours. I’m going to just hand it over, because that was brilliant.

Luke: Thank you.

Dan: And not just because you’re mentioning my book. That was really nice.

Luke: I know you’re going to pay me for that later, so it’s okay. We’re good.

Dan: Yep. Venmo. Venmo you. Or PayPal, or whatever.

Luke: Whatever the kids use these days.

Dan: Whatever the kids use. I think Venmo’s great, but the name just, I don’t know. It could be better.

Luke: Venmo Me?

Dan: Yeah, Venmo Me exactly. It’s not a-

Luke: It doesn’t work as well. Back in my day, we PayPalled people.

Dan: That’s right. It’s more like a verb. PayPal Me. Well, Luke thank you so much for being on.

Luke: Oh, thank you. It was fun.

Dan: Yeah, totally fun. I mean, so many things to think about, to talk about. Working, what’s next for you? What are you working on these days?

Luke: That’s a good question. Right now it’s a little bit more of the same. I got a whole bunch of stuff I’m doing at Google, which has eaten up a lot of my time. Needing to do less talking. Public speaking, that is. I think that’s good because I got some young kids, family, good times to spend with them.

Dan: Yeah. Do they bike as well? On the track?

Luke: Yeah, they try. It’s not necessarily a seven year old material.

Dan: Well sure, yeah, it could be dangerous. That’s right, too.

Luke: Yeah, but they’re getting there. We bike up in the yard and all those other things, so we make up for it.

Dan: Yeah. It’s funny, the one last thing on the track. We could do a whole episode on the track, right? But the one thing I always thought was, does it snow there? Probably not.

Luke: No.

Dan: Where you are? No? Okay. Because I was initially thinking, man, if this was in my back yard and it snowed, it’d be an amazing bobsled track, right off the bat.

Luke: Or snowboard track, right?

Dan: Yeah, yeah. Snowboard, exactly. Oh, man.

Luke: Ho, we don’t get the snows.

Dan: Yeah, no snow there. You’re better off.

Luke: We like to drive to it when we want it.

Dan: Yes, exactly. Well, that’s the … yeah, California. Man.

Luke: You get what you pay for, right?

Dan: I love it, I love it. Yes. Well, thanks again Luke, and keep rocking. Thank you for all the sharing you do, because honestly, it’s huge. I know it’s invaluable for a lot of people.

Luke: My pleasure, and I thank you a ton.

Dan: Yeah, thanks, man.