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Episode 16 June 7, 2016 | 39min

From Subtraction to Adobe

Our co-founders talk to Adobe's Khoi Vinh about how to build a great design team.

Show Notes

Paul Ford and Rich Ziade sit down with designer Khoi Vinh, who is currently the director of product design for mobile at Adobe. They trace his career from his early agency years in New York City, to his years as design director of nytimes.com, to his current work at Adobe, and they discuss everything from process, to scaling, to how to build a great design team.

Paul Ford: Hey, Rich Ziade.

Rich Ziade: Yo, Paul Ford.

Paul: It’s Track Changes from Postlight, the podcast that has some listeners who like to listen to things about technology!

Rich: They give us five stars a lot, too.

Paul: Oh man.

Rich: Did you see that?

Paul: It’s pretty good. I’m just, we’re all just waking up. This is an early Track Changes podcast recording session.

Rich: But it’s worth it.

Paul: [laughter] It’s three sleepy dads in the studio, sucking down coffee. I’m Paul Ford.

Rich: Rich Ziade.

Paul: We’re the co-founders of Postlight, a product shop and web agency in New York City, and we’re joined today by a man that many of you probably know, some of you will meet him for the first time, his name is Khoi Vinh. K-H-O-I V-I-N-H, Khoi, welcome.

Khoi Vinh: Hello. Thank you. Thank you for having me.

Rich: It’s such a badass name. Can I mention that?

Khoi: Is it really?

Rich: I think so. I mean, it’s a product of design itself.

Khoi: I wish you could go back in time and tell the seven-, eight-year-old version of me that it would one day turn out to be a badass name.

Rich: You didn’t like, early days?

Khoi: It’s just hard to have a name like that growing up in suburban Maryland where those kinds of names — I’ve got two silent Hs in my name, that’s not common in suburban Maryland.

Paul: I know, but they’re silent Hs, but it’s Khoi — I mean, you’ve got two four-letter names, just like me. And it’s nice, it’s unified. You can make a nice grid with your name.

Khoi: That’s true.

Rich: Did you have a Western, like a Westernized name? You know, like my uncle, Faraj, his name is Frank, and he owns a deli. [laughter]

Paul: You’re not Kevin anywhere?

Rich: Yeah, I was going to say — are you Kenny or any of that?

Khoi: No, no.

Rich: You didn’t have any of that?

Khoi: I might have, but I just have a single syllable first name, so it seemed…

Rich: Right.

Khoi: Like I’d be adding syllables.

Paul: Well, Khoi, those little Maryland kids are living empty, hollowed-out lives —

Rich: Exactly. [laughter]

Paul: — barely able to open their mouth to pronounce words.

Khoi: Except for the ones who went to Harvard.

Paul: Yeah, that’s unfortunate, isn’t it? Like, yeah. OK. Let’s not go down that path until we actually introduce who you are and what you do. Khoi Vinh, what is your title in this world?

Khoi: I’m director of product design for mobile at Adobe.

Paul: So at your base, you are a digital designer, like a user-experience designer?

Khoi: That’s right.

Paul: And you’ve been doing that for a while.

Khoi: A while, yeah. Since the nineties.

Paul: That’s right.

Khoi: Is one way to put it.

Rich: I got to know Khoi, before I actually met Khoi, for years through his blogs, Subtraction, which I always felt went a little bit beyond design, and touched on a lot of things that influence design, impact design, and how design impacts everything else. You still write, which is good. I used to write a lot and I stopped, and most people stop, and it’s great that you continue to do it.

Paul: I think, Khoi also, I’m going to speak about you for one second, you’re of the cohort that came to the web because your interests were bigger than one specific discipline.

Khoi: Mmmm hmmm.

Paul: Like the early set of people who showed up were like, “I’m into this, I’m into this, I’m into this. Digital’s kind of a way I could bring it all together.” If I go to your website, it’s as much about culture and film and —

Khoi: Right.

Rich: Yeah.

Khoi: I mean a lot of people came to blogging because it was very liberating and exciting and a great way to talk about their interests. But for me, that was all true, but it was also a chance for me to write, and I really enjoy that process, and that’s why I keep doing it. I mostly still enjoy it. But…generally it’s about writing.

Paul: It’s interesting to think that at some point there’s going to be thirty-year blogs.

Khoi: Yeah. I’ve got like a ten-something, ten-plus year blog, which is kind of crazy.

Rich: My blog is, it’s starting to break.

Paul: This isn’t about your blog. [laughter]

Rich: No, I know. This is about many blogs. I will put forward, and I don’t want to digress too far here, but over time, it’s just breaking.

Paul: Sure. Unless you build a custom content-management system and output static files like I did!

Rich: And that’s postlight.com. [laughter] Please come.

Paul: All right.

Rich: All right, rather than running through your resume here, what would you say is sort of, give us two or three big highlights professionally for you in your career.

Khoi: I’m probably best known for being design director for newyorktimes.com for about five years, and as previously mentioned, I write the blog subtraction.com. I had a start-up called Mixel for a few years that was acquired in 2013. I’ve been kicking around a bunch of start-ups since then, and I’ve been at Adobe since last August.

Rich: OK. Let’s dive in, just really quickly, newyorktimes.com: what’s the highlight, or highlights, within that five-year period?

Khoi: For me the big story was that I got to help reinvent the way The Times thought about design, particularly about product design. That company obviously has a long legacy of great design, tons of really talented designers and illustrators and photographers come through there.

Rich: Mmmm.

Khoi: They, at the time that I joined, were just starting to get more sophisticated about thinking of the web as a platform and, a little bit later, thinking about mobile as a platform, and how to design products on top of that.

Rich: Right.

Khoi: And I like to think I was, you know, played a pretty key role in doing that. We rebuilt the design team, basically from scratch when I came in, and reinvented the way design worked with all the other teams in the company.

Rich: That’s a big deal for a company that old and that entrenched.

Paul: So I think —

Rich: I don’t mean that negatively, but.

Paul: No, I think…it’s The Times, everyone has that, its our hometown newspaper, we all have our own personal relationships with it.

Khoi: Right.

Paul: So I mean, I think this is good for the, for people to hear, right? You go in, you’re design director. It doesn’t sound like you were moving many pixels around in a box —

Khoi: No.

Paul: — when you were doing that.

Khoi: That’s correct. Like I, I didn’t do a lot of design there. Most of what I did was hiring, which is the most important thing in design. A manager of designers can do, sort of think about who we need next, trying to find the right people to fill that role, and talking a lot with other parts of the business, other parts of the org, trying to figure out the process for getting really great design done.

Rich: Very interesting.

Paul: How does one, I think this is a very general question, I don’t there’s any specific answer that applies to everyone, but I’m always interested: how does somebody who is very much a practitioner, you are, you know, reading your blog, reading subtraction.com, you were someone who was thinking about the very bare bones structure of stuff, moving stuff around, you really knew how to make and design things, for digital, and for the web in particular. What was it like when you transitioned into that management role?

Khoi: Yeah, well that preceded me joining The Times, even. I mean, in the late nineties, when I was working at dot-com agencies, I was already managing people, and then in 2001, I co-founded a design studio called Behavior with a few other colleagues of mine, and —

Paul: That’s where I first met you. You hired me. For something.

Rich: That’s funny.

Paul: I cannot remember what.

Khoi: Yeah, you were a friend of Chris Fahey —

Paul: That’s right.

Khoi: That’s how I met you, yeah. Chris was one of my partners, still a good friend of mine. And as co-founders we were managing more than we were doing design, though as a small studio we were doing a lot of both.

Paul: Mmmm hmmm.

Khoi: So the transition was, I mean, I definitely thought about, OK, I’m getting to do less and less design, and have to put more and more effort into management, but it was a lot of winging it. It wasn’t like, following — there’s actually no book out there that I’ve seen that does a great job of telling designers, specifically, about how to become managers.

Paul: Right, I mean, I find that in —

Khoi: There’s a bunch of Medium articles. [laughter]

Paul: I found that in my — yeah, there is, on everything — I find that in my own career. Like, you’re pushed into it, rather than…

Rich: Yeah.

Paul: I think on the West Coast maybe a little bit more, there’s like a path, like hey, you need to go get this training, and we’re going to get you an executive coach, and —

Khoi: Right.

Paul: But here it’s like, oh wow, things are going well, I need to hire three people, oh my God there’s a huge integration cost to having three people do something with me, I’d better get better at making sure they’re all doing the same thing.

Khoi: Yeah, that’s right. I mean, you start to learn that all the things that you think design management is about, like policing the aesthetics or the design execution or making sure that designers talk to other folks in the business really well, or, I mean, other parts of the organization in a language that makes sense for them, or setting a creative vision for everything — all of that is, well, it’s important, it’s really just a very small part of the job. The biggest part of the job is just clearing the way for designers to do their work and also being a kind of therapist/coach/ — [laughter]

Rich: It’s a tricky bunch, isn’t it?

Khoi: Yeah. Yeah, whatever.

Paul: How do you spot talent? Is there anything that’s sort of, like, rings a bell in your brain?

Khoi: I think there are a lot of different approaches. My particular approach is, you know, I look for a great portfolio, and I look for somebody who can articulate himself or herself really, really well, in written form, in spoken form.

Paul: So you kind of gotta get them into the room?

Khoi: Yeah. I mean, a lot of times what I’ll do is I’ll look at a portfolio and then I’ll ask for a phone call interview, and I will set the expectation that the phone call will be like five minutes, maybe ten minutes, just so that nobody’s, like, disappointed if it doesn’t last long. And what I’m trying to do on that call is just hear if this is a person who, first, actually did the work that’s in their portfolio, but second, is able to express himself or herself in a way that’s compelling or convincing. And I learn a lot from that call, and if there’s enough to suggest that there’s, you know, some really smart thinking there, then I’ll ask them to come in and meet them face to face.

Paul: We hear a lot from people who are looking at career transitions into one of the fields, you know, product management, design, engineering, if someone’s out there, they’re smart, this is something that they’re genuinely engaged with and interested in, where do they start? Do they go to school? Is there one book that they should read before they make any decisions? Do you have any, like…?

Khoi: Well, I did write a book about making that transition recently. [laughter]

Paul: Oh! What a good question to ask then. Let’s talk about that book.

Khoi: It’s a book called How They Got There. You can find it at howtheygotthere.com. It’s interviews with fourteen digital designers, folks from agencies, from big tech companies, from independent practices, and it’s all about how they got their first big break, and many of them came from other career paths and eventually found their way to doing design, so. The big lesson for me from that book is that there’s no set clear path, and a lot of these people started working when we all, like, you know, Paul, Richard, we all started when the design industry, or the digital design industry, was young, so to speak. But I still think that the whole industry is quiet young, and, like, you really can’t trade on best practices or clearly pre-written rules for how to get ahead in a career these days, or how to make your career. Just because the technology continues to change.

Paul: Well we see it with engineers a lot, we’ll go in an organization and someone will be talking about XML and pipeline transformations when everything now is driven by APIs, which I know is a lot of buzzwords, but it’s a very, it represents this very significant shift in how work is done.

Khoi: Right. Right.

Paul: And it’s gonna take them a while to catch up. They can catch up.

Khoi: Right.

Paul: So yeah, no, there’s no path, and you have to stay current.

Khoi: Yeah, you have to stay current, you have to be open to change, or to possibility, and the bedrock principles are still being able to write and to speak clearly and being curious and driven and being willing to get out there and meet other people and build a network and create opportunities for yourself.

Paul: So those are the commonalities between the fourteen people?

Khoi: Yes.

Paul: Yeah. So —

Khoi: Very much so.

Paul: — the real bare bones, like, I was willing to take risks, I introduced myself to people, I learned how to talk about what I was doing, and I continually applied and rehearsed my talent.

Khoi: Yeah, absolutely. I mean, Erika Hall was one of the first interviews I did. She’s co-founder of Mule Design out in San Francisco. Maybe my favorite learning from her was that she said early on, she figured out a lot of her heroes, people who you would think are way too busy to talk to you, were reachable by phone or by email. She would just call them up and say, “Hey, could I take you to coffee?” And she would take them out for a half an hour and get all this fantastic advice that she previously thought was completely unobtainable.

Paul: I think that’s very real. I think that for me, what I found is, people occasionally hit me up for advice, and all you have to do is kind of come to my neighborhood, and…I don’t know if you’ve had that experience. There’s, people will ask for stuff that’s actually very hard to do —

Khoi: Yup.

Paul: — but if it’s easy, you’re gonna find the half hour because you actually, we’re all just inclined to help each other get across that hump.

Rich: Paul, do you want to share your address?

Paul: Yeah, sure.

Rich: Make it available…

Paul: I live in the, well you know what, we work in Union Square, so it’s a lot easier.

Rich: Yes.

Paul: Erika Hall, we should note, too, she wrote a really good book about user research.

Khoi: Yes.

Paul: Yeah.

Khoi: She’s been really —

Paul: Smart, thoughtful person who has a lot to add. So I mean, that’s cool.

Khoi: Yeah.

Paul: That’s good.

Rich: I want to jump ahead if possible. Two things I want to cover: one is your time at Adobe now —

Khoi: Mmmm hmmm.

Rich: What’s up, and what’s going on there? Adobe’s doing a lot of stuff.

Khoi: Yeah.

Rich: And I have to say, Adobe could have gone the way of big box software retirement.

Paul: I mean, look, it had a reputation as a kind of stubborn company with a lot of crashing software.

Rich: Yeah.

Khoi: Mmmm hmmm.

Paul: There are a lot of screenshots out in the world of, like, Adobe products imploding. [laughter] That was the experience of, like, the last five years.

Rich: But I mean, they built, and they continue to build some landmark pieces of software that are part of peoples’ every day lives. But they’re also expanding and growing, kind of branching out, and it’s actually kind of fascinating to watch. I’m always fascinated to see big companies react nimbly to what’s happening around them. I think it’s an incredibly impressive feat.

Paul: And you’re thinking about Creative Cloud and stuff like that.

Rich: Even beyond — I just, I’ve just, you know, you see the apps — a large organization like that, to put out, what I view, relatively speaking, snack-sized pieces of software, practically, isn’t easy. It isn’t easy to reconcile the brand and the image of the company, too. So it’s impressive to me, to see that happen.

Paul: I mean one question is, when you go in there, that, Adobe is ground zero for what we think of as digital design. They created, it’s born on the back of Postscript, which is the language that printers used.

Khoi: Right.

Paul: And so it’s as old and rich a legacy of how things should work on a computer as possible. What was it like, coming in as someone who was a very web and sort of product-specific person, coming up in that culture. Also on the East Coast, this true hot center of what represents —

Rich: I’d be interested in hearing the courtship to pull a Khoi Vinh into an Adobe. [laughter] We don’t have to go through every bit of detail, but that’s interesting in and of itself, right?

Khoi: Yeah, I mean the transformation that Adobe’s gone through in the past several years has been remarkable. And it’s part of what drew me in. I mean, if you think about, in the pre-Creative Cloud world, the whole company, this really big company that had been around for thirty years, was completely oriented around shipping box software, and everything had to work through the lens of one of their big pieces of, you know, marquis applications like Photoshop or inDesign or something like that. And then this transformation to subscription, you know, getting all your software through the cloud. I think that in and of itself is really amazing. I think now, I can’t remember the exact number, but the majority of the revenue is subscription-based now, and almost entirely removed what we call perpetual licensing.

Paul: Yeah, I would have no idea how to buy a non-subscriber version.

Rich: They’re on eBay.

Paul: Right.

Rich: You can get the boxes —

Khoi: The old version, yeah, but the new versions don’t happen…I mean, I think what was really brilliant about the transformation is it entailed completely resetting the way the company thinks about software. So now instead of having to ship every feature idea through one of the marquis applications, now you have room to create other franchises, whether they’re the numerous mobile applications that we’ve been creating on iOS and Android or the brand-new franchises that will start on the desktop but will also move to our mobile app platforms like Adobe Experience Design, XD, our new UX/UI design tool.

All that’s possible because now we don’t have to think about accruing sales specifically to Illustrator or Photoshop. Now we just think about the Creative Cloud subscription, and so long as people are continuing to get value out of it, and re-upping every year —

Rich: Yeah.

Khoi: — then we’re free to innovate in a much different way. In a way that’s much more in line with what the customer wants. They want to continue to get new value out of that subscription, and that’s what we’re motivated to do.

Rich: Sure.

Paul: So you’re walking down the street one day and you look down at your…Android KitKat device and —

Khoi: Right.

Paul: Yeah. Which I’m sure you have, and —

Khoi: I’ve got Android devices — [laughter] — that I like very much!

Paul: OK good. So you look down at your Android KitKat phone and there’s an email from Adobe one day, saying like, “Hey, we saw…we, Khoi, what’s up?”

Khoi: So in 2013, I had sort of finished the journey of my start-up, Mixel, and was thinking about what I was going to do next, and I actually, on my blog, had written, intermittently, about Adobe software, and had been sort of pointedly critical about it, and having to do that once more in 2013, but this time I got an email from Scott Belsky, he’s a friend of mine, he’s the co-founder of Behance, and at that time he was VP for mobile and community, I believe, at Adobe.

Rich: And Behance is a…

Khoi: Behance is a creative social network, it’s for sharing portfolio work. And Scott said, “Hey, I read your piece. Why don’t you, if you have time, come by, I’d love to catch up.” And he and I caught up not long afterwards, and he sort of showed me all the things they were working on in terms of mobile software, and also —

Rich: Worth noting Behance was acquired by Adobe.

Khoi: Yes, I’m sorry. I’m sorry, yeah. Behance had been acquired by Adobe.

Rich: It was an independent —

Khoi: Right.

Rich: Sort of community for designers.

Paul: Well there’s a larger point there, which is that Adobe started to acquire things that were, I think we all considered as quite progressive and pretty good.

Khoi: Right.

Paul: And not screwing up the acquisitions.

Khoi: Right.

Paul: Like Yahoo bought things we loved like Flickr and obliterated them.

Khoi: Yeah.

Paul: Delicious as well. But Behance, then Typekit, which —

Khoi: Exactly.

Paul: — in some ways, it sounds like it became the core of Creative Cloud, or became connected to Creative Cloud.

Khoi: Yeah, they did a smart thing, they gave a lot of responsibility and influence to the folks at Typekit, the folks at Behance, to bring that sort of start-up, web-based, mobile-based thinking to their desktop, big-picture stuff.

Rich: Also it’s a — Typekit is a cloud service. A lot of the thinking around, just, the product of cloud service was brought into the organization just by acquiring Typekit. So you weren’t just getting a bunch of fonts and a cloud service, you were getting a team of people who think about software in a completely different way.

Khoi: That’s exactly right.

Rich: To infuse into the culture. There was definitely an offsite before these before these acquisitions —

Paul: Oh yeah.

Rich: — started happening where the executives at Adobe got, like, croissants and coffee [laughter] —

Paul: Big Sur.

Rich: — it was at the Marriott —

Paul: Yeah.

Rich: Yeah. Exactly. They went to, like —

Paul: They had to drive up a really windy road to get to —

Rich: Exactly, yeah. And they’re like, “Guys, how are we gonna do this? Three days together — ”

Khoi: It’s almost like you guys work there. [laughter]

Paul: It always pains me to praise a very, very large organization, but…but like, acquisitions like this are typically very destructive.

Khoi: That’s right.

Paul: Just typically like —

Rich: Totally.

Paul: “Hey we got these, we want the cool new thing, and like, somebody was like, ‘my daughter uses that,’ or ‘my son’” — and it’s just, and they go and they buy it and no one knows what to do and the team doesn’t get a leadership role and everyone’s egos are —

Rich: And then there’s that friction of the existing incumbents and the, just, all the pain of humans interacting…

Khoi: One of the reasons I joined is I saw how high the retention rate was at Behance, who are here in New York. I mean, they did not —

Rich: Yeah.

Khoi: Go through really painful massive attrition.

Paul: It’s actually something fascinating, right, because large companies are not mindful of the signal that sends out to the larger community?

Khoi: Right.

Paul: They’re like, oh hey, we gave these annoying young nerds all this money, and now they’re ungrateful, and we’ll go get another one. But it’s actually this spiral, where everyone starts to recoil.

Rich: Yup.

Khoi: Yeah.

Paul: And you’re no longer cool, if you get acquired by a bad company.

Khoi: Right.

Paul: Like, all these weird social dynamics going on.

Khoi: Yeah.

Rich: Takes a certain level, I mean, just as a large organization, of humility and maturity to just leave that organization alone and not swoop in and say, “Well, we’ve got an idea of how to optimize this.”

Paul: We’re also hearing another story, which is that Khoi was a critic of the product, and that they were like, “OK, look, we’re going to welcome that criticism.”

Khoi: Yeah, I think, I mean, it partly, it was through my friendship with Scott, but also, like, the whole organization, folks who had not been part of the Behance team even were very welcoming and were really human about owning up to past flaws and thinking critically about how they could course-correct going forward. So that really impressed me.

Paul: So they, you reached out, started to have coffee…

Khoi: Yeah, so actually Scott asked me if I had learned anything from my experience with my start-up, Mixel, which was an iPad app for creativity, if I’d learned anything that might go into a new app on top of Creative Cloud for Adobe, and I went away and wrote up a bunch of thoughts about that, and sent them back over to Scott, and he really liked them, and he basically put together a little team and we prototyped for a while and eventually in the spring of 2014, 2015 I think, we officially released an app called Adobe Comp, which is a layout app for iPad and iPhone, and soon will be on Android. It’s a very, very fluid mobile-native way of combining images and type and assets that you create art drawing, and photo apps together, in a sort of next generation Illustrator or inDesign-type of fashion.

Paul: That’s out now? I can go get that in the app store?

Khoi: That’s now, and you can actually get a free Adobe ID and download the app, and try it out.

Paul: What was it like going from, I mean, The Times had global scale, but ultimately, it was a lot of pages, like a lot of web pages.

Khoi: Mmmm hmmm.

Paul: What was it like to go from a start-up and relatively smaller software projects to something that was going to be completely global, global marketing campaign.

Khoi: Yeah.

Paul: Almost by default millions of users?

Khoi: Yeah, so that’s a big part of what I think about today, because we have all these apps on Creative Cloud that run on mobile, and they have an audience of millions of folks, and the interdependencies of the component parts of the software are really advanced and complex.

Paul: Mmmm hmmm.

Khoi: So a lot of my job is thinking about how to make the experience consistent across all of our apps. When you’re sharing stuff, when you’re importing stuff, when you’re accessing our type tool, or doing this or that. At the same time, I’ve got to balance thinking about each individual app on its own merits, and trying to really get it to the next level of engagement, of discoverability, and really trying to turn it into the next big franchise, so it’s, it’s a tough balancing act.

Paul: But you’re actively thinking about that scale? That’s what you’re telling us.

Khoi: Right.

Paul: Like we have an idea, and we talk a lot, a small shop building a product on day one, we can think about an MVP, a min viable product — I’m looking at Rich as I say this — we can throw away so many concerns. We don’t have to think about —

Rich: Yeah.

Paul: — how it’s going to do in China, stuff like that. And it sounds like that has to be there, maybe not from day zero, but a product doesn’t go to market in any way unless a lot of boxes get checked off.

Khoi: That’s true. When Adobe starts a brand-new product, that product benefits tremendously from being part of the ecosystem, from having the Adobe brand on it, maybe the biggest benefit, and there’s a lot of foundation work that the app has to do in order to integrate into that ecosystem. But at the same time, we try to keep in mind that we’re competing in a world, especially on phones and tablets, in a world where new apps get to five, ten, fifty million downloads and have millions of monthly active users, and they don’t have to think about the ecosystem, an ecosystem, right? They’re building on their own merits, and they’re fully aligned with what their customers or their users are trying to do. So we really have to balance these two ideas, the one of being part of an ecosystem and the other of competing in a marketplace that is full of really nimble players. It’s tough.

Paul: And when you say a small team is prototyping a new mobile product, how big is a “small team”?

Khoi: So when I started working on Comp, it was just myself and one prototyper.

Paul: OK, so just two people, sharing emails.

Rich: Fun.

Paul: That is fun.

Khoi: Yeah, that was really fun, and it was just, rapid prototyping, just, you know, throwing ideas back and forth for a while.

Paul: So the prototyper is mostly a programmer, or…?

Khoi: Yes, he’s a programmer. He is based out west but came to New York for a little bit of time. We did some work and then when he went back out west, we continued to do stuff over email or chat or what have you.

Paul: What are you saying to him? Are you saying, what if I double-finger-touch-it and move to the left?

Khoi: Yeah. Exactly.

Paul: OK.

Rich: And he’s building out these sort of mock versions of the app?

Khoi: Yeah, so I started with some, you know, wireframes or schematic drawings of how I thought the interface would look, and lots of descriptions about how I thought they should work, and he would build those up and we would look at a prototype or a build and decide what was working, what wasn’t working, maybe new ideas to throw in there, or other ideas to chuck out. And we just did that in rapid succession for a number of weeks, until we got to a point where we felt that the features were in good enough shape, I mean still very, very rough, but in coherent-enough shape that we could put it in front of some users.

Rich: Yeah.

Khoi: And we did some user testing, and got some feedback, and when we sat down with the folks at Adobe to go over the feedback, lots of things didn’t work, and there was, you know, lots of stuff that obviously we didn’t know the answer to yet, but the team at Adobe were still enthusiastic enough to actually make the team bigger at that point, add a bunch of folks —

Paul: And they kind of speak software, right? So they’re see —

Khoi: Exactly.

Paul: Yeah. We were —

Rich: OK, so there was a dating period. Essentially they hired you as sort of an independent contractor —

Khoi: Right.

Rich: — consultant, that’s how they got to know each other.

Khoi: Right.

Rich: That’s worth noting, in terms of his —

Khoi: Yeah.

Rich: — transition into Adobe, is they dated for a while.

Paul: The thing that I’m hearing is we go, we offer that to our clients a lot. We’re like, “OK, hey, you just came in and you said you want this really big thing, really fast?”

Khoi: Mmmm hmmm.

Paul: “And the way to do that is we’re going to give you one or two people, and mess around. We’re gonna build — ”

Khoi: Right.

Rich: Don’t make the big bet just yet.

Paul: And just like, they immediately recoil, because they don’t see that as cutting their risk. And so it’s, it’s just worth noting, like a big —

Rich: Yeah, it’s that throwaway.

Khoi: Yeah.

Rich: Is usually their reaction.

Paul: A big software company is really comfortable with that, like that’s part of the process, and actually part of the process whereby you decide that you are, you’re somebody that they’re going to continue working with.

Khoi: I’ll tell you, one of the biggest lessons I’ve learned in the past five years, having been in start-ups and been in pure software companies, is in contrast to the way I thought about products when I was at a design studio before, basically the little agency, or a big agency, or at a big company, it’s very difficult to pre-determine what a product is going to look like or feel like or even do from the beginning.

And maybe the biggest truism that I’ve discovered about software products is they are the direct result of the people who work on them in the beginning, those very early formative stages. I think a lot of companies, especially big companies that say, “OK, we need a social network to do this,” or, “We need a big app that does this” — they don’t understand how important the people are, and they will write out a list of goals for the product and then just go and find whoever’s going to sign up to do that, and essentially it’s a bit like trying to determine the outcome, to use the metaphor you used a moment ago, Rich, of a relationship. Like, you can’t know where two people are going to go, or three or four people are going to go, in the way they relate to each other or what comes out of what they do.

Paul: And we see it a lot with media companies, like, it’s just hard for them to go, “OK, go figure it out.”

Khoi: Mmmm hmmm.

Paul: Because they have a real preconceived notion, and often they’ve only been able to get the budget to get something built —

Khoi: Right.

Paul: — because they can say, “We’re going to do this to compete with this other organization — ”

Khoi: Right.

Paul: “ — and we can cut our risk that way.” And they come to us and we’re like, “Well, you actually should go for a little more risk right now,” and it’s, everyone’s shoulders get tense, and then it becomes a conversation, but I see that, and then the flip-side is that it’s intolerably expensive to do this. To work this way is actually quite costly, you’re not quite sure what you’re getting.

Rich: Maybe. I mean, I think —

Khoi: A lot of times companies will put a big team on a project before a line of code, even prototyping code, has been written. And that’s incredibly expensive as well, and in many ways —

Rich: And uncertain.

Khoi: Yeah.

Paul: I mean, they spend more on paper towels than they do on this project [laughter] but because the outcome is unclear and it can’t get reported back in a sensible quarterly way, they’re like, “What are we doing here?”

Khoi: Exactly.

Rich: Yeah.

Khoi: Exactly.

Rich: I mean, I think people, they can’t help but sort of drive their thinking through comparisons that they understand, and if I walked into an architect’s office and said, “Play around a little bit. I need this to be better.”

Khoi: Yeah.

Rich: That’s an open-ended sort of…there’s a lot of unknown there. And you don’t know when it’s going to stop, and you don’t know if there’s anything even viable that’s going to come out of it, and I think that’s what most don’t get about product, is how dodgy it really is.

Khoi: Or how organically it evolves.

Rich: And how organically it evolves.

Khoi: Yeah, it’s not a linear — it’s very rarely a linear progression —

Rich: Exactly, exactly.

Khoi: — from the first line of code to shipping code.

Paul: I think another thing too is people always assume that costs will increase, which is often true, but sometimes if you just let this go, someone will come back and go, “Actually, we figured out that we can do — we can have a million less lines of code.”

Khoi: Right.

Rich: Yeah.

Paul: “If we just put this rectangle here, the users get real excited, and things can save money or increase the level of engagement or whatever, whatever.” But it’s just that it’s a real puzzler, but what’s interesting is that Adobe and these big software companies are —

Rich: Creating spaces to allow that kind of play to happen?

Paul: Managing that risk is how they thrive?

Rich: Yeah.

Khoi: Some of it’s geographic, too. I mean, Adobe is located in San Francisco. They have an office in San Jose, too. They’re right at ground zero for this kind of development, this kind of thinking about products. In New York here, I think, we’re not as exposed to this approach.

Rich: Definitely.

Paul: It’s a subject that we as, trying to build products in New York City are completely…it comes to us every day.

Khoi: Yeah.

Rich: Yeah.

Khoi: I bet.

Paul: It’s not the Bay Area.

Khoi: Right.

Rich: I do have one more question.

Paul: OK.

Rich: And I just need an — he’s been casually showing them, I follow you on Twitter.

Khoi: OK.

Rich: You bought — I guess you bought an Apple Pencil with iPad Pro.

Khoi: Yes.

Rich: And he’s like, “Check it out, I just sketched a little thing!” And it’s pro —

Paul: Khoi is a good illustrator.

Rich: No, wait, that’s just you, sort of playing around?

Khoi: Yeah. I mean, I actually went to school not to study computers or to figure out what org charts look like, I went to school for drawing and painting. I went to school because when I was in high school I spent all my time in the art room.

Rich: Got it.

Khoi: And so I had a passion for making marks on flat surfaces with pens, and I had put that on the back burner, the way back burner, for many, many years while I created this career in design and software. But Apple Pencil and iPad Pro, just, sort of, finally dovetailed those two and —

Rich: What are your impressions, by the way? I mean…

Khoi: Apple Pencil is an amazing achievement in many ways, because when I draw with a pencil, in some apps that sort of mimic real-world media, and sort of see the substrate or the texture of the virtual paper you’re drawing on, sometimes I feel like, “Why can’t I actually feel like the roughness of the paper through pencil?” Because the line is so accurate and the responsiveness is so true that it’s really great, and with —

Paul: Jony Ive was there with the shock collar —

Khoi: Yeah. [laughter]

Paul: Making sure that — [electronic zap noise]

Rich: Yeah.

Paul: More like paper!

Khoi: But also in some ways it’s better than drawing with a real pen a pencil, or on paper, because, like, and not that I want to become a total shill for all things Adobe, but their vector-drawing apps, like Adobe Illustrator Draw, which essentially give you infinite resolution, you can zoom in as far as you want and still have the pencil to create incredibly fine detail or zoom out, and…

Rich: Yeah.

Khoi: And stuff like that.

Rich: Oh, this is an iPad app?

Khoi: Yeah, this is an iPad app, yes.

Rich: Called Adobe Draw?

Khoi: Yeah. Adobe Illustrator Draw, yeah. It’s —

Paul: Well you know, there was software like this in like, the early nineties, like a lot of infinite zoom and a lot of early tablet stuff. It sometimes takes twenty years for those ideas to percolate.

Khoi: Absolutely. Yeah, and I think it’s really come together with the pencil and some of the software that’s available out there.

Paul: Or like Amazon Echo with speech. Suddenly there’s a product pattern there where everyone’s all excited and happy about it, in a way that they’re not, even with like, Siri.

Khoi: Yeah, yeah.

Paul: Where it’s just like, it comes together as the product.

Khoi: Same with smartphones, too. Like, smartphones were kicking around for x number of years before iPhone came out, so…

Rich: Yeah.

Paul: God help us with what’s next. I have no idea.

Khoi: Virtual reality.

Rich: It’s the future!

Paul: VR, yeah, it might be VR’s turn, but…

Rich: I don’t know, man. We’ll see.

Paul: [sigh] Do you own a pair of Occulus Rift goggles?

Khoi: I don’t. [laughter]

Rich: I want a deep-dive into why, what are they called, Google Glass?

Paul: Google Glass, yeah.

Rich: Why that failed. I think that’s a fascinating story.

Khoi: Yeah…that’s…

Rich: I think it’s just because you look like an idiot.

Paul: It didn’t help.

Rich: Yeah, and now VR is around, and it’s, “Oh look, on the F train, there’s somebody who’s — ”

Paul: I think it was also —

Rich: “ — giggling at, while there’s a VR on their face.”

Paul: It was also just slow and not that fun.

Rich: Headset, yeah.

Paul: It just…these things are fun. What Khoi is telling us it that he loves to draw and he hasn’t had time for it, but it’s really, it hits that part of his brain and lights it up.

Khoi: I think that’s right. It really is fun, and it…

Rich: It’s really cool.

Khoi: It makes you keep wanting to do it. It’s not that it’s, you’re doing it because you’re consciously saying, “OK, I’m trying to figure out the future.” You’re just doing it because you’re enjoying the moment.

Rich: Yeah. Very cool.

Paul: So people who want to know how to become Khoi Vinh [laughter] or one of fourteen people like Khoi Vinh in interviewed should go get a copy — I’m assuming they can, what’s the website called?

Khoi: howtheygotthere.com.

Paul: Good website. How They Got There: Interviews With Digital Designers About Their Careers.

Khoi: Right.

Paul: Can I get that as an ebook?

Khoi: You can get it in a number of electronic formats, and you can also get it in hardcover.

Paul: Exciting.

Rich: I want to close this by asking Khoi what he does really badly. That he’s really ashamed of. [laughter]

Paul: Oh yeah, what are you terrible at?

Rich: Yeah.

Khoi: What do I do really badly that I’m ashamed of…?

Rich: Do you have like, lower back problems?

Khoi: I definitely have lower back problems since having children. [laughter]

Paul: That’s just being a dad and lifting babies.

Khoi: Yeah, yeah.

Rich: How’s your singing?

Khoi: My singing is terrible.

Rich: All right! Cool.

Paul: OK, that’s good.

Khoi: My singing and dancing and ability to play musical instruments is terrible.

Rich: Nice.

Khoi: Yes.

Rich: All right.

Paul: Do you see yourself returning to, just, ever just designing things?

Khoi: Well I do a number of projects on the side that sort of scratch that itch, so —

Paul: Because it never goes away, right?

Khoi: Yeah, I mean, one of the things I really enjoyed about co-founding a start-up or being in the start-up world is that every day is different, and some days — actually I did quite a bit of design when I was at the last start-up I was at, it was called Wildcard.

Paul: Mmmm hmmm.

Khoi: But then another day you might be thinking about, like, an investor meeting, or you might be thinking about a partnership or something like that, whatever.

Rich: You do it all.

Khoi: It’s just having the variety, I think, has been the thing that’s kept me interested in my career going forward. If I were designing every day I don’t think I would be really happy. If I were purely managing, whatever that is, every day, I don’t think I would be happy.

Paul: Well on that note, thank you so much for coming in and talking to us.

Rich: This was great.

Khoi: Thanks.

Rich: Really enjoyed it.

Paul: Khoi Vinh, and subtraction.com.

Khoi: That’s right. That’s my blog.

Paul: Excellent place to find Khoi and find all things Khoi-related. Appreciate it. See you soon.

Rich: Thanks, Khoi.

Khoi: Thanks, guys.

Paul: That Khoi Vinh is a bright young man.

Rich: He is. He’s going places.

Paul: I think he’s going to do something in the design industry. I can’t wait to see what happens.

Rich: Yeah.

Paul: It’s interesting to see a specific cohort, like a specific group of human beings who’ve been doing it for a while, like, the giant companies and those people, which kind of includes us, like we work with big companies too, and we work with small companies —

Rich: Yeah.

Paul: As you get older, it all sort of starts to mush together a little bit.

Rich: Yeah.

Paul: So it’s just…I don’t know, it’s just an observation.

Rich: It is mushing together, yeah.

Paul: Yeah. It’s…the software’s figured out where the web is, and the…I don’t know. Look, hey. I think that’s enough.

Rich: Yes.

Paul: OK.

Rich: Wonderful podcast.

Paul: [long sigh] We’d better get back to the office.

Rich: Yes.

Paul: All right, this is Paul Ford.

Rich: And Rich Ziade.

Paul: Hey, can you bring the energy level up just a little bit?

Rich: AND RICHIE Z!

Paul: YEAH! [laughter] Perfect. All right, we are the co-founders of Postlight, a product shop/web agency right here in Manhattan.

Rich: And if y’all have questions —

Paul: — send an email to:

Rich: [email protected].

Paul: That’s [email protected]. Rich, good show, talk to you soon.

Rich: Have a great week. Buh-bye.

Paul: Bye.