Practice

Thoughts on engineering,
design, & product management
from the Postlight Track Changes podcast

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Foreword

Starting a podcast was a very useful endeavor for two co-founders in their first year of co-founding. Both of us love to talk. But this—the Track Changes podcast—required us to listen.

We made this book because we wanted to capture a little bit of the year, and share what we learned from listening. We interviewed fascinating people at the top of their fields, people coming up, and people figuring out their next big thing.

What they told us, if you listen between the lines, is that if you do the work, on bad days and good days, bad years and good years, then something great will happen. It takes a long time. Which is why this is called “Practice.”

This was a good year, and we love the work. There are many years to go. Onward!

Your friends,

Paul Ford & Rich Ziade

P.S. The following pages are taken straight from transcripts, then edited and condensed for clarity.

A few things we learned this year

  • how to launch new products for old companies
  • how to launch new things for ourselves
  • how to stop working on something that isn’t broken
  • how to advise massive companies and government organizations
  • how to hire 20 people
  • how to navigate a client bankruptcy
  • how to find and furnish a new office
  • how to draft a mission statement
  • how to listen to criticism
  • how to be good partners to a variety of clients
  • and how to do a weekly podcast.

Dean Hachamovitch

Advisor, LifeQ and Board Member, Arendt Center

@DeanHach

Former corporate vice president for Internet Explorer at Microsoft. Took a battered, neglected version of IE and pivoted it back towards being a powerhouse web browser. Worked in a world of huge teams, at massive scale.

One of the challenges, whether you’re at a really small company, on the outside trying to figure out who to connect with, or inside of a very large company, is you very quickly try to find who knows what. It’s that whole notion of knowledge management, or institutional memory, and it’s essential. You start asking around. We had some relations and we built up better relations quickly.

There’s a gentleman who sent me a piece of flame mail, saying, “I work at Microsoft, and I resent your team and I resent this and I really hate this,” and just vented, like two screenfuls. I guess it was therapeutic for him. I wrote back a one-liner, which was, “You’re right. Why don’t you come here and make it better?” He joined the team ten days later and had a great run, and made things a lot better. It was a great way to get a job, because he was factually based and he had good ideas about how to solve. That happens.

At some level, everyone in this industry got a start somewhere. It was, “Hey, I wrote a game.” “I figured out how to cheat on a game.” “I figured out how to do this.” And you just build that up. I think it’s really easy to lose track right now of how much better it is than it was before, because we can spend few hours talking about the miserable state of a certain class of tool and how many hours a week engineers lose to shuffling data from Point A to Point B.

There really is a cast of hundreds, or depending on how you want to do the accounting, a cast of thousands, making this stuff work. In terms of what I wrote, for the most part it was email and PowerPoint. It turns out that software development really is a professional activity, and there’s this amazing recurring thing around, “OK, well, it needs to work, it needs to work fast, it needs to work consistently, it needs to work with low memory, it needs to work in French and in German and in the Far East, it needs to work on a server, it needs to work on a phone.” So there’s this whole long list of what you expect.

There are these fun stories of new hires coming in. So some fresh-out-of-college person shows up and the email goes out to the team, “Oh, please welcome Joanna Smith, who’s joining us from Carnegie Mellon University,” or from Stanford, or wherever. You go by the office, just say, “Hey, welcome to the team, how’s it going? What are you working on?” They go, “Oh, I have this bug to fix. They gave me this bug. I’m all checked in, and I’m going to go fix this bug.”

You go, “Well, that’s great. You’re getting started on your first day, fixing a bug, and that’s going to be great. Just one word of advice here: don’t break the Internet.” There’s this moment of frozen, you know, “Wow. Wait. This code is going out to how many boxes? Wait. What stands between me and melting the Internet? How is that going to work?”

On the current state of the web

What you really want to do is write a service that runs happily in the cloud. Then people are going to interact with that on a variety of devices. They can interact with it on their phone, on their pad, in a browser, from their Raspberry Pi, from their Amazon Echo by saying, “Alexa, go do something.” You’ve seen these Amazon buttons, right, where you just hit the button and detergent comes to your door? That’s just a great example. There’s a web service doing the right thing.

So I don’t really see an endgame or a demise of the web. I see a whole lot of evolution.

Jon Lax

Director, Product Design, Facebook

@jlax

Worked in digital media for more than two decades. Before Facebook, spent twelve years as a partner at Teehan+Lax, where clients included Medium, Google, YouTube, GM, and Delta Airlines.

I am both participating in and getting the front-row seat to watching a business operate that has never really existed in the history of business. How many companies are operating at the scale that Facebook is? 1.6 billion people in the community.

There are a lot of different things happening out in Silicon Valley at different scales and resolutions. I would say that the things that are valued out there are big impact, global-scale, huge, huge things.

If you work in finance and you really want to operate at the top of your game, at some point you’re going to spend some time in Wall Street. If you work in film, you’re probably going to spend some time in Hollywood. It doesn’t mean that you can’t make films out of New York or somewhere else in the world, but really, I think if you’re going to operate at the highest level you’re going to spend some time out in Hollywood.

If you work in product design or engineering and you really want to work at a very high level, you probably should spend some time in the Valley. It doesn’t mean that it’s the only place to do this work, but I think right now, for this chapter of my career, it’s the place that I want to be right now.

Jon Lax

“If you work in product design or engineering you probably should spend some time in the Valley.”

Jon Lax

Director, Product Design, Facebook

Tweet

Photo courtesy of Jon’s Twitter

It’s impressive to watch people operate at that level. I’ve worked with some really good engineers in my life, but I have to say, I work with a lot of really, really good engineers, and the things they are able to accomplish—I’ve never heard “No, we can’t do that,” ever.

Some of my designer friends who work with IT groups or engineers, they spend their whole life trying to convince the engineer that it can be done. That is not a problem that I have.

Camille Fournier

Former CTO at RentTheRunway/ZooKeeper PMC Member & Committer, The Apache Software Foundation

@skamille

Kellan
Elliott-McCrea

Former CTO at Etsy

@kellan

Two former chief technology officers (CTOs) who are also good friends and frequent collaborators. Avid students of organizational structure, and advocates for—as well as critics of—technology’s ability to change organizations.

Camille: People are hard, but I would say the hardest part at the end of the day is the executive part of the job. Dealing with the CEO, dealing with the board, dealing with the other executives.

Engineers are fragile creatures, and they want to be coddled and they have their needs and you want them to be happy because they’re so hard to hire. Also, the business has things that need to get done. You’re constantly the person that feels like they’re in between those two worlds.

That’s not all of it, but that’s a huge part of just being stuck in the middle of all those negotiations.

Kellan: There are lots of possible ways you get to be CTO, but the best CTOs are that bridge between the executive function and the engineering function. If you’re in a tech startup at least, you probably have the largest organization. You certainly have the most expensive and sort of needy organization, and you’re a major expense for the company—but you’re also the site of what differentiates the company. And you’re trying to build something special— there’s a reason tech startups are a thing. There are aspects of engineering culture that allow you to envision the future in different ways that run counter to standard business culture.

How so?

Decentralized decision making, access to information, “good ideas come from anywhere,” “failure is part of learning.” These are not your standard executive belief systems.

Camille: So yes, your team is not children. They are adults, and in fact, this is one of the things that I love about the tech culture, is that you do want them coming back to you and having a conversation, but at the end of the day, for organizations to run successfully, there have to be standards. You may re-evaluate those standards, you may question them occasionally and change them. It’s not that they have to be set in stone, but they have to exist.

Kellan: You never have enough people. I asked a friend the other day, “How can I help?” They’re like, “Do you know thirty people that can start next week?” I’m like, “I’ll send you the list.” I don’t have that list.

Then there’s running it day to day. “Is it supposed to feel like this?” It’s like, “Yes, that is normal.” Then occasionally, “Is it supposed to feel like this?” “No, that is deeply fucked. Let’s de-bug this problem.” Those are kind of the rough areas.

Khoi Vinh

Principal Designer, Adobe

@khoi

Oversees the large family of mobile products at Adobe. Previously a startup founder, design director of NYTimes.com, and agency founder.

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, where new apps get to 5, 10, 50 million downloads and have millions of monthly active users, and they don’t have to think about the ecosystem. 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.

One of the biggest lessons I’ve learned in the past five years, having been in startups and pure software companies, in contrast to the way I thought about products when I was at a design studio before: 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 that they are the direct result of the people who work on them in the beginning, during 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 of a relationship. 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.

Gina Trapani

Director of Engineering, Postlight

@ginatrapani

Programmer, the founder of Lifehacker, technology community leader, and Postlight employee.

On Lifehacker

I was an English major in college. My dream was actually to be a writer. The programming thing happened as a matter of practicality, like, “Hmmm, this seems like a sensible thing that would pay me a salary.” So I felt like, “I’m living the dream. The web has enabled me to become a writer.”

Even though on some level I didn’t think I was a real writer, because it wasn’t on paper. Which is pretty amazing, because then when I actually did publish my book, I was like, “I didn’t hear from anyone about this.” No one ever said a word. I was used to a hundred people chiming in on a post.

So I loved it. And I became absolutely addicted to the site and the growth of the site and the pace of the work. Hearing from so many people every day was great, and I didn’t sleep a lot. But I loved it.

The programmable web became the thing. Everything had an API. Flickr had an API. Twitter had an API. And I would write about all these cool things that people were making every day, and every day there was this voice in my head that was like, ‘If I had time…’ I had 15 ideas that I’d like to build.

So yeah, I got to a place where I thought, ‘You know what, I’ve done everything that I can do here and now I want to build stuff. Instead of writing about stuff that other people are building, I want to build stuff.’ So it was a very amicable departure.

On coming to Postlight

I’ve been running a two-person company now for two years, and I definitely have a little bit of lone wolf in me. I enjoy having my name on a thing and having the control and having it be up to me and getting to make the decisions, but the truth is that it’s slow. You can get so much more done when you’re collaborating with other people who know more than you do, who know different things than you do.

Gina Trapani

“You can get so much more done when you’re collaborating with other people who know more than you do.”

Gina Trapani

Director of Engineering, Postlight

Tweet

Photo courtesy of Bill Wadman

And I did get to the place where I was like, I want to learn, I want to work with other developers and learn. I was the person that was like, “This is how we’re going to do it.” But I wonder how other people are doing it.

Aaron Straup Cope

Editor at Large and creator of the Who’s On First project, Mapzen

@thisisaaronland

Programmer who works with large data sets and cultural data. Formerly of Flickr, now at Mapzen, geographical computing (“geo”) expert, building a gazetteer.

How much is in this gazetteer of places? How big is the world?

Well, we have a fraction of it right now. There are ballpark 3 million postal codes, probably 4 million when we factor in the things that we don’t have, probably 2, 2.5 million administrative places, so cities, neighborhoods, regions, and then venues—it will only ever get bigger. We have been importing an old open dataset from 2010 that a company called SimpleGeo released, which is business listings. And so right now, that’s 20 million venues. A lot of hair salons. A lot of plumbers. We probably don’t have the hipster bar that opened up last week. But on the other hand, if you need a plumber in Kansas or Missouri or rural California, we probably have it.

On data permanence

One of the things that we talk a lot about is we’re not the first company to try to do open geo. Other companies have tried and failed for whatever reason. I mean, the goal is to succeed. The goal is to do all the things. And hopefully we will, and maybe we won’t, and if we don’t, then the goal is for it not to be a complete reset to zero, that there will be something that someone else can pick up and run with without having to start all over again. To start with, one of the early decisions we made was that we wanted a gazetteer that was portable and robust and durable across time—

Do you print it on brass?

We’ve joked about that. In the interim, it’s text files. It’s a gigantic bag of text files, because it turns out they’re the best. I mean, there are lots of other super-efficient, very clever data formats, but often they’re proprietary, binary formats that are optimized for something.

It is all on GitHub. GitHub is more the reflection of the kinds of features and functionality that we want that Git provides right now, or does the best approximation of providing. It has some problems. Git doesn’t really do well with a million tiny files. There are lots of places in the world. But we point to Git as a way to say, this is how it should be, and we’re going to use bubblegum and duct tape of this service, and either the technology will catch up and Git will make advances and suddenly it will be fast and smooth and easy, or we will figure something out.

How long are you going to be working on this gazetteer?

As long as it takes.

Natalie Podrazik

Software Engineer, Google

@nataliepo

An iOS programmer, at a company called Byte at the time of the interview, now at Google.

So this is the part that was hardest to learn as an iOS developer: I had to listen to the symptoms and read between the lines of how frustrated the user was about the bug report to be able to actually understand what was going on. I mean, there isn’t a way to debug like there is on a backend web server — you can just read the logs.

It wasn’t like the web.

Exactly. All those errors are standardized. In iOS, it’s kind of like a feeling: something doesn’t feel good right now. Is that a bug or is that intentional?

I ask user the typical bug-reporting questions: What did you expect to happen? What actually happened? But mostly I just try to listen to their tone, of how frustrated they are, because sometimes they just want to be heard and they just want a reply that someone is listening and actively improving their product as a result.

There are lessons that I’ve come to absorb as an iOS developer, whether I like them or not, that I always bring to the other designers or product people that I’m working with. Number one, users don’t read. They don’t read. They don’t read instructions, they don’t read dialogues. They just want to do the thing. I’m speaking from a very realistic point of view—this is pretty real talk, as an iOS developer—but yeah, users don’t read.

Natalie Podrazik

“Users don’t read. They don’t read instructions, they don’t read dialogues. They just want to do the thing.”

Natalie Podrazik

Software Engineer, Google

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Photo courtesy of Natalie Podrazik

When you’re the only iOS developer you have to speak on behalf of what’s right for the user, and what Apple wants you to do. So you have to memorize the Human Interface Guidelines. You have to really pay attention to people — not just your best users, not just your active users, but open-zero users, and what they’re doing.

That’s the kind of most embarrassing, surprising part about becoming an iOS developer, is that they call it “iOS Developer” but really you’re an iOS product person. You have to know the whole package. You have to understand what people are going through when they use this product. You have to understand all the design problems, all the user-experience problems, all the data problems, all of the past versions of iOS problems, all of Apple’s intentions going forward. You just have to have a lot on your shoulders, and it’s kind of a lot, you know?

I run a meet-up called Cocoaheads, and it’s so supportive. It has a lot of Mac-developer veterans who’ve been doing this for many years, and they have very strong opinions and a very long history with Apple. They use this group not because we’re sharing technical secrets, but because it’s almost like a support group. We need to help each other make better software.

Karen McGrane

CEO and Managing Partner, Bond Art + Science

@karenmcgrane

User-experience expert who writes books, gives speeches, leads workshops, and takes on a variety of web projects with her agency Bond Art + Science.

I was due on a project up at Condé Nast, and Razorfish had put in a new CMS platform that I will not name, but I will refer to it only as “Schminterwoven.” And it was terrible, right? I didn’t mean any disrespect to the team that implemented it. It was a bunch of forms, and we had all these visions for how the websites were going to work, and “wouldn’t it be cool if you could browse this way,” and “wouldn’t it be nice if there were these kind of filters.”

And then it turned out that the team that was actually going to manage and update the website, all the journalists and magazine staffers and whatnot, hated the CMS so much that they weren’t going to use it. And they revolted, and said no. They boycotted it, basically. So that meant that in the very immediate term, a lot of things had to be torn out of the front end of the website because there wasn’t anything to drive it, and in the long term, they wound up tearing out all of Interwoven, and I think they’re still cycling through platforms over there.

It was a bad scene. And it really had a major effect on me. It was sort of a lightbulb moment, where it hit me that all my dreams and ambitions for how I wanted websites to work didn’t matter all that much if we didn’t have tools on the backend that worked well for people.

I think, for me, it’s almost like having an ability to survey the landscape and try to figure out how you can articulate someone’s pain to them, in a way that makes them recognize, “Oh, that, that thing. That’s what hurts. I didn’t even know that was what was hurting me, and you’ve just described my pain to me so perfectly that now I actually feel like I can fix that pain.”

Liza Darwin
& Casey Lewis

Founders, Clover Letter

@lizadarwin and @caseymlewis

Former teen magazine editors who launched “Clover,” a daily topical newsletter and app for girls ages 13–22.

Casey: Everyone thinks that teen girls just care about Snapchat, or just care about taking selfies of themselves. And we had this theory that that just wasn’t true, and we wanted to prove it.

Liza: And it felt like the right time, it’s an election year, big things are happening in the world, people should know about them.

A community of readers formed

Casey: They’ll ask us a question and we’ll turn it into a piece, or they’ll submit essays, really smart essays. It has shaped our content in a way we didn’t really foresee.

Liza: And no one wants to be more involved than a teen girl. They just want to be involved in everything, so that’s how we had to start an ambassador program. Now we have about 300 ambassadors who basically are our free mouthpieces. They shape the brand. They shape the content.

On fundraising

Liza: It’s been a learning experience. This is our first company, of course, and we tried to be as informed as we possibly can. We ask everyone’s advice, almost to a fault, I would say, just because we take it such to heart, and it got to the point where it almost felt like we had whiplash, because one person would say, “go to VCs, get all the money you can,” and then someone else would say, “whatever you do, don’t go to VCs.” And we read everything and we listened to everything and we finally tried going the VC route and decided quickly that wasn’t for us right now. We haven’t spent any money, really.

Casey: Meeting with some of these VCs and going to these meetings with these finance guys who don’t know media or the teen audience at all was not great. Us walking into some of these meetings, you know, we’re bubbly media girls. They’d say, “Teens don’t care about anything.” And we had some people tell us straight-up that they don’t like investing in female-founded companies.

On audience development

Liza: It was very reassuring to know that not only do teens read email, they read it every day, which has been hugely helpful.

Casey: Because these girls have really formed a community, and we want to be on the ground with them. And no one is doing events for teens in a cool way. You could do a lame school event, but you know, it’s clubs, or you know, extracurriculars. So we want to do that.

Liza: We want to maybe expand into video in the future. We’re sort of thinking lightly now, but you don’t even have to spend tons of money, but these girls have such cool stories and they’re from all over the world, and we wanna put a camera in front of some of their faces and see what happens.

Casey: They’re real girls, and it’s good for other girls to see these real girls who are not on a reality show or who aren’t Instagram celebrities, you know?

Julia Pimsleur

Author, Million Dollar Women & Founder and Board Member, Little Pim

@JuliaPimsleur

Documentary filmmaker and entrepreneur. Founder of the Little Pim foreign language-learning series and author of Million Dollar Women: The Essential Guide for Female Entrepreneurs Who Want to Go Big.

So I’m working this job, I’m there for several months, and I’m having a blast. And then one day about nine or ten months in, they take me out for coffee and they say, “So…we think you should run your own company.” I said, “No, no, I like running your company. I’m having a blast here. This is great!” And they said, “No…we actually…you need to run your own company.” And they basically fired me. We sometimes say you need to release someone’s talent back into the universe, right? This was one of those. The talent got released back into the universe.

She starts Little Pim to teach kids foreign languages

I did ultimately raise $2.1 million for my company. Which was amazing, excruciating, and wonderful, and I found some really great partners, but when I got through the eye of that needle and looked back, I said, “Wow, that was so much harder than it needed to be. How can I help make that easier for the women coming behind me?” So that’s when I started teaching this boot camp on weekends in my conference room, to help women learn how to raise angel and venture capital. And that evolved into the book Million Dollar Women. Because I just kept hearing the same stories over and over again, of the challenges we were all facing.

Look, it’s hard for everyone to raise venture capital. But then there are added layers for women that are specific to us, and so I would say 85% of what I teach in my boot camps and in my book applies to anyone trying to raise money. Women have less access to capital. We’re not growing big, multi-million-dollar businesses. And this is a place I thought I could help move the needle.

There’s nothing more gratifying than helping to fix a problem that you’ve experienced. So many entrepreneurs are solving problems they experienced themselves. I think for me, it’s helping other women have access to capital so that they can take their businesses to the next level, or just access to the right networks, the right skill set, the right mindset. You know, it was interesting when I interviewed these million dollar women across the country, women who’d built multi-million-dollar businesses, we all agreed that it’s not rocket science. You really just need three things to go big: the right mindset, the right skill set, and the right network. And basically everything you need falls under one of those buckets.

David Mendels

CEO, Brightcove

@Brightcove

CEO of the video-hosting platform Brightcove.

What’s happening inside that video rectangle on your screen?

There’s also a triangle, by the way, that’s a play button.

There’s actually a lot going on. The video player has a lot of layers of software and policy. It’s a mini operating system. It has to know what video to play, security or geo-restriction rules. There may be other user-experience things, like what’s coming before, what’s coming after, is there a bumper, is there a recommended video or an end screen at the end. It has to know whether to start pre-loading the video, so that when I hit play as a viewer, it starts instantly—or maybe I don’t want to incur that cost, in which case I won’t pre-load the video or some segments of the video.

In the case of a commercial media company like Time Inc., it’s then going to start by calling out to an ad server, like Google’s DoubleClick perhaps, or there are others out there, and get an ad. It has to then stop the video, play the ad, stop the ad, play the video, and there’s a lot of technology in how that all works.

Meanwhile, that same rectangle, if you will, is a piece of code. It is emitting beacons of analytics, which are going in multiple directions. So you’ve got analytics that we provide on viewership, on geography, on platform. They may also be integrated with third-party analytics like Omniture or Google Analytics, or they might have created something custom with a service like Mixpanel. They might be using other analytics like Nielsen or Comscore. So there’s a whole range of things that can be plugged into that rectangle that add different kinds of value for a company like Time Inc.

What’s happening is that video is the most powerful medium that humans have created, and combined with the open Internet, the two together enable this incredible proliferation of new forms of communication. And so it’s just going to keep going.

The challenge is, how do we continue to improve the quality of the experiences that people have consuming these things? And in order for this to really happen, we have to continue to make it easier and much lower cost. If we instantly said, let’s take all of broadcast video and put it over the Internet, we’d break the Internet today, and it wouldn’t work. So there’s still a lot of technology and things that need to get developed over the next five or ten years for this to work.

Elizabeth Spiers

Founder, The Insurrection

@espiers

Calls herself a “digital media nerd.” The founding editor of Gawker. Became a central connector in the growing world of digital media, serving as a “launch consultant” for many new brands. Now moving into virtual reality.

What is VR today?

It’s so new right now, it’s difficult for a lot of people to really understand what the implications are. But there are what I think of as gateway drugs to serious VR, and 360 video is one of those. You know, I think it was smart for The New York Times to start there. But there are kinds of VR that you see in everyday life, but you just don’t think of them that way.

For instance, Snapchat filters. That’s augmented reality, and they’re putting a lot of money, as an institution, into augmented-reality R&D. But if you asked the average Snapchatting 13-year-old whether they have ever experienced augmented reality, they would say no. Because it’s seamless, and you don’t think of it that way.

One of the challenges of 360 video and documentary format is that it’s realistic enough. There’s a really beautiful landscape, there’s something happening narratively over here, and you’re looking up and down and exploring it, while these people are talking. You almost feel rude, like you’re somebody who walked into somebody else’s conversation.

I think it’s really easy to do whimsical high-concept stuff in VR, in a way that you can’t do with anything 2D. There are so many things that just cross genres. On the Vive, there’s a game called Job Simulator. It’s hard to define: is it a game or is it a comedy? It’s intentionally animated in such a way where the animations look blocky, like they were made in AutoCad. I in 1988. But it’s entirely comedy-driven. There’s nothing you can really win. You just pick a job and they show the most, almost Office Space-y, abysmal version of doing it. And it’s just really funny.

Future plans

We’re actually launching a publication on Medium called “There Is Only R.” It’s a reference to when people talk about the difference between virtual reality and augmented reality and mixed reality. You know, for the user, if they’re at all convincing, it kind of doesn’t matter, because there is only reality.

Jeffrey Zeldman

Founder, Studio.Zeldman

@zeldman

Web designer and web design ethicist. The proprietor of Studio.Zeldman, a design studio focused on web design for content sites. Founder of HappyCog, founder of A List Apart, co-founder of A Book Apart and An Event Apart.

On client work

Yeah, at times we’ve been guilt tripped about it too, I think. Design goes through this period of, a real designer just does product, just does their own product, is just an entrepreneur and client services is so 1999, or whatever. I mean, design without a client, it’s not really design.

You need client services. New York is a client services town. One reason: Silicon Valley made its own industries. It was like it was a new place, there was nothing going on. There were some banana farmers, and peach farmers, and then they started making computers. But in New York: Grey Advertising was formed here in 1802, before the original New York Times building burned [Ed. note: Grey was formed in 1917 and the Times building did not, best I can tell, burn.] I mean, there’s just this ancient culture. There’s rich jerks and then there’s people working for them. That goes back forever.

Jeffery Zeldman

“There’s rich jerks and then there’s people working for them. That goes back forever.”

Jeffrey Zeldman

Founder, Studio.Zeldman

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Photo courtesy of Jeffrey Zeldman

On the next act

If you go to the site, studio.zeldman.com, currently it’s a microsite, which is a one-page site. OK, so it’s a one-page site that is an app because it has an “estimator.” A thing that helps you sort of figure out if you want to work with us and qualify yourself a little bit.

And when we launched we didn’t have a portfolio, for complicated reasons. But we’re launching that in a few days and we’re launching an “About” section. So we’ll actually have a navigation bar with two items on it, which kind of makes me sad. Because there was something so pure about it.

Matt Haughey

Senior Editorial, Slack Technologies, Inc.

@mathowie

The founder of MetaFilter, a collection of sites and communities that is one of the real success stories of the web. Started at Pyra Labs, today is a writer for Slack.

On Pyra Labs, creator of Blogger

I’m telling family I’m going to a startup in San Francisco. Well, it doesn’t make any money, but it’s going to be great. Yeah, the weird part was knowing in my heart that Blogger was going to enable the planet to communicate. I had that, and I knew that was our end goal, and yes, Pets.com was happening. Everything was happening around me, and the garbage pile was flying through the skies, and people were being fired every day on the same street I was on, but I knew this Blogger thing is the greatest idea imaginable.

He bought a book, Philip and Alex’s Guide to Web Publishing, by Philip Greenspun

It tells you the entire world of programming is just four things: put stuff in a database, take stuff out of a database, display it on a page however you want…Well, that’s three things — that’s it! That’s the entirety — and so I could go to any language, and just ask, how do I put crap in a database? How do I read it out of a database? How do I format it on the page? And that’s ColdFusion, PHP—I sort of picked up just doing that.

I wrapped my head around it and went, this is amazing — this is within everyone’s grasp. I did not know it was so easy. It was great. And it was philosophical, there was hardly any code in the book. You go look up syntax later.

The early Internet came out of the academic world. All the early bloggers were grad students or were just coming out of college, and they had free webspace. I came from the academic scientific community, which asked, “What do I need to know to get my work done, and then how do I tell everybody about it?” But that was an important aspect.

I think all the early internet, 1999–2005 Internet people, they had an academic bent, because there was no money, so it’s like, well I discovered this great thing and made this great thing, I just want to tell the world so they can do it, too, so we can all have great things.

Anil Dash

Activist

@anildash

Activist “working to make technology and the tech industry more humane, inclusive, and ethical.” Helped start blog pioneer Six Apart (RIP), makers of Movable Type, one of the key blogging platforms of the 2000s. Advises organizations like Medium and DonorsChoose.

At Six Apart we were getting death threats because we had said that we might charge some users for the software. People calling us horrible names, people who we thought of as our online friends. It was an epiphany for me. I mean, it was miserable at the time. We were all literally sitting at our desks crying. Then we realized, “These are people.” They had projected relationships onto me or us, or this app, or whatever. It was meaningful to them and they felt betrayed. It was at an emotional level. It wasn’t your features, or your design, or that you redesigned your website. It was, “You’re my friend, and you didn’t even think to ask me about pulling the rug out from under me.” That was what they felt.

Anil Dash

“We were getting death threats because we had said that we might charge some users for the software.”

Anil Dash

Activist

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Photo courtesy of Anil’s Twitter

That was revelatory to me, because it made me understand what the Internet was. Everything prior to 2003 or so was just “getting set up.” It was just plugging in the wires. And then Friendster was 2003, and blogs start to take off. What changes then is, we realize that all we had been doing prior to that was clearing our throats and getting ready to talk to each other.

The Internet was for people to communicate. The main thing people do on the Internet today is send messages to each other. That’s the most popular thing. Then the second thing is sharing things that other people have published. And then way, way down below those is writing original things.

On the power of technologists in culture

As geeks, we won. Tech is the driver of major mainstream art and culture. And music, and films. Look at the apps and the tools and the tech that you use everyday. You’ll instinctively know, if you think about it for 30 seconds, “Boy, they’re screwing up in this one way.” Or: “Well, this doesn’t work with the screen reader, and blind people can’t use it.” Or: “Gosh! If this takes off all over the world, it would completely undermine the entire worker economy.” Or: “This is spelled wrong.” Whatever it is that you can find those fundamental flaws in the tools and technologies we use everyday. Take a look at it and tell them. Hold them accountable. First, go to the company. If they don’t fix it, then go to the world. Take seriously that the things we used to think of as bugs, as flaws in our software, are increasingly becoming really significant weaknesses in culture and amplifying the worst problems and flaws in society. If we can see that those things are connected and hold people accountable appropriately, then we are all helping do the work we should be doing.

Rex Sorgatz

Founding Partner, Kinda Sorta Media & Contributing Editor, Medium.com

@fimoculous

Media strategist, writer, technology and product leader. Grew up in rural North Dakota without the Internet, in a town called Napoleon.

On his essay “Netflix and Ch-Ch-Chilly,” about going back to his home town of Napoleon, North Dakota (population: 792)

I had gone back to Napoleon for a high school reunion a few years ago and I started thinking about what has changed about the place in 25 years. And it was amazing to me, when I started thinking about it: Nothing has changed. Most places, there’s some sort of gentrification or un-gentrification, or there’s a Walmart that opens, or there’s the big company that opens or closes — something happens to the place. But Napoleon was exactly the same. Nothing big had moved in. Nothing had left. It’s still graduating 20 kids. It’s trapped in time. And so it started to get me thinking, “I wonder if I could fake a scientific experiment here. If everything else is equal, what is the control that I can say has changed against it and can we study that?”

And so the thing I try to study is what has technology and information done to Napoleon and, in a grander sense, to these small, rural communities? And so my essay just sets up this idea that if I go back and I find kids like me , today, and just sit down and talk to them, how different will their lives be? Because everything else is the same, except that they can pull out their phone and listen to any song in the history of recorded music, which would’ve blown my mind.

I was a very information-thirsty kid, but had no information to consume. We didn’t have cable TV until I was a teenager, and even then it was 11 channels and none of them were the good ones. I didn’t have MTV — I didn’t see MTV until college. And my major outlet for media was the high school library — there was no real library in town, there was just a high school library , which  had five magazines.

Do you remember which ones?

Sports Illustrated. US News and World Report. Newsweek. TIME. And People. Those were my five magazines. Imagine everything you knew about the world was from those five magazines.

What he found in Napoleon today

Unlike me, they have a very keen sense of the outside world. They understand politics information in a way that would’ve blown my mind. And so I was curious if they were more aspirational than I was, because I was definitely not an aspirational person. I was inquisitive, but I didn’t have any dreams of making it big. It was the last thing in my mind.

I was surprised to find that every kid I talked to has a very strong awareness, has visited other cities, gone places, and when you ask them what they think their lives will be in 25 years, they all said, “I’ll probably be back here on the farm, having a family, and I just love it here. I love my community.” They said the word “community” over and over again. Almost like someone was drilling it into them or something. But I was surprised that there was not a strong desire to get out. I even used the phrase “get out” with some deep hesitation, because I don’t really think of it that way. I think their lives are really interesting and great.

They’re going to be on the farm with unlimited access to all the world’s information.

And to me that sounds great, you know?

Virginia Heffernan

Author, “MAGIC AND LOSS: The Internet as Art”

@page88

A critic, cultural commentator, writer, and editor, published everywhere.

At Dartmouth College, John Kemeny, who wrote BASIC, or co-wrote BASIC, had come to be the president and save us from our colonial ski town. It was literally Luddite in the sense that we had wood stoves and we put colonial stuff on our doors. So Kemeny came and he put a giant sighing, heaving, rattling mainframe in the middle of town, and agreed to teach the school children BASIC. We learned BASIC, and I took the road of pretending to code for a minute and a half using BASIC, which probably doesn’t even count, and then instantly got into the chat side of things, the avatar creation and the fantasy game, the D&D-style game that we called “Excalibur,” because why not?

’79, ’80, ’81. Finally my friends called it computer dating and started singing “Desperado” and when I walked around, you know that burning, burning, burning feeling you have when you’re teased and you’re 11? Just like, fall down to the center of the earth, I can’t go on?

When I first heard Hallie sing “Desperado” to me, I was just like, “I’m going to freaking change my ways. There is no question I’m going back anywhere near that poisoned thing that’s going to wreck my life.” And so I went off for a long time and when it resurfaced in Compuserve, I told myself I had to be really careful, the “Desperado” side was going to come back if I wasn’t careful. You know, I was pretty careful for a while, but you guys know this. You see networked computing and something in you trips and you just….You can’t let it go.

What is she learning?

I have really embraced, very much against my nature, anti-abstraction and material culture. So I’m trying, for instance, to not use a GPS. I’m perpetually disoriented. I’m trying analog tools. The Navy is, for fear of cyber attack, training on sextants again. And compasses and so on. And even celestial navigation. So I’m trying for once to look around me at 3D objects and actually sit in a room with flesh-and-blood people and—

[Much later in the conversation.]

We have this idea that our brains are stunted because this canon of neuroscience that keeps telling us about all the brain damage done by cultural objects, by computers, by whatever, by headphones, by connectivity — we believe we’re stunted because who wouldn’t believe they were stunted in the face of this monstrous, god-like thing. Yes. It’s official. Even Faust can’t know as much as Google.

Virginia Heffernan

“Even Faust can’t know as much as Google.”

Virginia Heffernan

Author, “MAGIC AND LOSS: The Internet as Art”

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Photo courtesy of Virginia Heffernan

So you go get a sextant.

I mean, a compass, just look at a compass. Isn’t it pointing to some magnetized part of the poles? You know, it took me a while to think, this code looks magic, this app looks magic. But then I saw a compass and was just like, this is magic. The poles of the earth exert such a magnetic pull, is this right, that the compass thing quivers in relation to them? Right here in Manhattan, in the city?

I just sat down with a bunch of chemists, Harvard chemists, and wow did they have way-out beliefs. I mean, one of them says he does all his chemistry for the greater glory of God. Ad maiorem gloriam Deum. You know, I didn’t meet an atheist among them.

Michael Bierut

Partner, Pentagram Design

@michaelbierut

Jessica Helfand

Senior Critic, Yale School of Art

@jessicahelfand

Michael Bierut is a partner at the design firm Pentagram. Jessica Helfand is a senior critic at the Yale School of Art. Both have résumés a mile long.

Michael on Pentagram

Pentagram is a design company based on an unusual sort of model. It is a partnership among creative people. Right now there are 21 partners in 5 offices, and each one of the partners runs a smallish design group within the overall structure. So it’s been around since 1972, a long time, and all of those partners are creative people. We all manage everything by consensus, there’s no managing director, there’s no business person, it’s just a bunch of art school graduates who sort of banded together, partly for fun and partly for mutual protection.

What I’ve seen happen a lot of times with design businesses is that quite rightly, a designer will go into a partnership with a business person, or sometimes there’s a three-legged stool, there’s the person who’s the creative designer, there’s the operations person that makes sure the rent is paid and the lease on the Xerox machine is up to date and everyone is registered for health insurance, and there’s an outside person who sells and is the public face of the place.

Usually, the more successful those latter two people are, the bigger the place get. The bigger the place gets the more kind of vaguely tortured the creative person is, because that person then is spending all their time doing what they don’t want to do, which is administering a large firm with a lot of activity. And so a lot of times, the creative person leaves. Then the two remaining people decide they’re never going to make that mistake again, they’re just going to hire more malleable people who are willing to take orders, and commoditize sort of the design/creative part of the operation.

I think that’s a very sensible business choice. But the Pentagram model has successfully inoculated us against that by having it be over its entire 40-plus year history run entirely by creative people. So a lot of times, our financial model is really simple, and I thought that was based on some sort of commitment to rigor and clarity. Now I realize it’s because almost the entire partnership, to a person, stopped taking math classes after 8th or 9th grade.

Jessica on artistic identity

There was a man who was the dean of the School of Art when I was a grad student. He happened to be the father of a friend of mine—I grew up across the street from him as a very small child. He’s now 84. he’s a painter. He’s retired from Yale, where he was dean for many years. And he hasn’t shown his work in a long time—40 years.

If you google him, you won’t find anything. But this man goes to his studio every day and makes work. And he’s having a very small show, and asked me to write something for the catalog, and I said to him, “David listen, you have to understand something, I only write about people who are dead so they can’t disagree with me.”

Jessica Helfand

“I only write about people who are dead so they can’t disagree with me.”

Jessica Helfand

Senior Critic, Yale School of Art

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Photo courtesy of John Dolan

It sounds funny, but it’s true. I’m very thin-skinned as a critic. I said, “But if I was ever going to make an exception, this is the time.”

And so what ensued—this was last spring—and I made about half a dozen studio visits to his studio. It’s in the basement of his house on a cul-de-sac in a rural bedroom community of New Haven. And then I went off to write this essay, and the privilege was so huge to me, to see someone who’s a generation ahead of me, as I try to figure out the next chapter of my life as a maker, right?

So I’m a teacher, I’m a writer, I’m a designer, I have a studio, I’m a mother. We all have these different identities that we have to bridge. But there was something about seeing this person who has this incredible discipline and love of what he does, that he goes to the studio every day, and I didn’t realize when I set out to do this, what an incredible journey this was going to be for me.

He said something really great to me one day. I said, “David, you know, I have a painting studio, the book that just came out has paintings in it, I feel kind of betwixt and between painting and design, I don’t have a practice with employees anymore, should I be having a different kind of art practice?” And I was just really flummoxed about the entire identity personhood of me.

And he said to me two things. First of all, he said, people like us are going to make stuff. That’s what we do. We make stuff. And then he said to me, and I thought this was such a great line:

“The thing is Jessica, it’s not what you have to do. It’s also what you get to do.”

I realized that he saw that studio as this kind of seed bed of opportunity. A lot of what he does, like, from one week to the next, is just move things around on the wall, and it’ll become a whole new juxtaposition of a set of situations that become fodder for a conversation or a drawing or a painting. And I thought there was something great about that. Totally devoid from technology.

This was just about idea, mind, form, making, process, sketchbook, understanding, you know, from one day to the next. 100 days, another 100 days. Building a body of work over time.

The Co-founders

Paul Ford and Rich Ziade

Rich Ziade is co-founder, Postlight, an entrepreneur, and an expert in managing large, complex software development projects. As the sole founder of Arc90, a pioneering software firm in New York City, he oversaw product development for large, multi-year projects in education, publishing, and insurance, among other industries. Under Rich, Arc90 simultaneously incubated numerous experimental web products, including Readability, which in 2016 is a wholly owned subsidiary of Postlight used by partners to power hundreds of millions of “readable” views of web content globally every month. After steering Arc90 to a successful acquisition in 2014, Rich served as Chief Product Officer of the Beatport platform, managing millions of high-quality audio tracks for an audience of millions of active music lovers and professional producers.

Paul Ford is co-founder, Postlight, and in addition to a career as a consultant and software developer has been a noted writer on technology and culture for publications like The New York Times Magazine, New York, The New Yorker’s website, the New Republic, Harper’s Magazine (where he was an editor for five years), Elle, Wired Magazine, NPR’s All Things Considered, and dozens more. In 2006 he brought the 160-year archive of Harper’s Magazine to the web and developed archive projects for Bloomberg, Condé Nast, Thomson Reuters, and other firms. From 2010–2015 Paul was a Director at the media digital strategy firm Activate. Paul’s single-issue essay of Bloomberg Businessweek, “What Is Code?” won the National Magazine Award in 2016, and he also contributed a regular column called “Big Data” to the New Republic through 2016. Paul is an advisor to the web publishing platform Medium, advises the White House on digital strategy, and teaches in the MFA program in Interaction Design at the School of Visual Arts. He frequently speaks and lectures on technology around the world and in the media.

About Practice

These interviews were adapted from Track Changes, the weekly technology and culture podcast from Postlight, hosted by Postlight co-founders Paul Ford and Rich Ziade.

Tom Meyers produces and edits the podcast. Paul Ruest and Noriko Okabe record the podcast at Argot Studios in Manhattan. Elizabeth Minkel coordinates, researches, and manages the podcast, as well as writing the show notes and transcripts. Matt Quintanilla designed the podcast logo.

To produce this book, Chloe Olewitz collated and edited down the full transcripts of the podcast. Paul Ford edited that collection into the final form. Elizabeth Minkel proofread.

Director of Product Design Matt Quintanilla designed the book, Product Designer Silas Burton designed and built the web version, and overall coordination was provided by Managing Partner Meredith Franzese.

Made by Postlight, a digital product studio in New York City