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Episode 4 March 15, 2016 | 38min

Anil Dash: From Entrepreneur to Activist

Our co-founders talk to Anil about the early web and building digital products.

Show Notes

In this episode, Paul and Rich talk to entrepreneur-turned-activist Anil Dash about the early days of the web, access and inclusivity, and the ethical responsibilities of the people who build digital technologies.  Anil describes himself as an “entrepreneur, activist and advocate working to make technology and the tech industry more humane, inclusive and ethical.” He helped start Six Apart (RIP), the company that made Movable Type. He’s gone on to cofound Makerba.se and Activate, and advises sites like Medium and DonorsChoose. Over the last several years he’s shifted the majority of his focus to social activism, working to make tech more inclusive and accessible to all.

Plus we try to settle how much you should tip on a New York City cab ride — no matter what the interface.

Full disclosure: Paul and Rich know Anil and have for years; Paul has worked with and for Anil. Anil advised on of Rich’s startups. Our world is small and insular. We welcome and accept all feedback.

Paul Ford: Hi, and welcome back to Track Changes, the podcast from Postlight; a New York City agency that builds applications and websites. My name is Paul Ford. I’m a co-founder of Postlight and I am joined by…

Rich Ziade: Rich Ziade.

Paul: Are you also a co-founder —

Rich: Comma, co-founder. Yes.

Paul: Great, great. Now we’ve created our own LinkedIn. Rich, I just heard that I sound really angry.

Rich: That’s OK. Channel it.

Paul: That’s the feedback I got. Let me try to mellow it down a little bit. Today we have a person in the studio who may or may not be angry. He’s going to tell us. His name is Anil Dash. You might have heard of him from any one of 7,000 other podcasts he’s appeared upon. He’s also an old personal friend and someone who hired me for a while, so welcome to straight-up conflict of interest. However, I’m going to use this as an opportunity to bust his chops and challenge him. Anil.

Anil Dash: Hi.

Paul: Thank you for being here.

Anil: I’m so excited to be here. I was hoping to get the chance to be angry.

Paul: So Rich, I’m going to tell you some things about Anil, and then I want you to tell me how you met him. He’s an entrepreneur. He’s an activist and an advocate working to make technology in the tech industry more humane, inclusive, and ethical. He’s wearing a pink sweater and a white shirt underneath it, probably blue jeans or slacks. And he’s here in the studio today. Rich, how did you meet Anil?

Rich: I think I reached out to him. I think I reached out to him a bunch of times and then he finally responded.

Anil: That sounds like me.

Rich: Well, you know I was a fan of … I consider Anil a blogging pioneer and one of the people … Am I allowed to say blogging pioneer?

Paul: We’re all laughing in the studio.

Rich: There are like seven to twelve people who were blogging before I think the word even really took hold, and he was sort of part of that world.

Paul: Do you remember when that word took over?

Anil: I sure do!

Paul: Sad.

Rich: You, Paul Ford, were one of those —

Anil: Oh, yeah. One of the OGs.

Rich: Anil was. Dave Winer was another that I pursued, so to speak. I had this shop in New York and I said, “Anil, I think it would be great to meet and just talk.” I didn’t really have an agenda. I just wanted to meet you.

Anil: Yeah, but you didn’t need more than that then. I think early enough on, if it was that, “Your writing is interesting” — the fact that, one, somebody found you on the internet, two, thought that whatever crazy thing you were talking about was interesting, was enough to be like, “Yeah, well, we should get coffee.”

Paul: That’s how you and I met.

Anil: Yeah.

Paul: Fifteen years ago, now. You were like, “Hey, let’s get coffee.” Essentially.

Anil: Yeah. I think an old roommate of mine was getting coffee with you and I was like, “You’re going to meet Paul? Can I pretend to have a reason to crash that?” That was it.

Paul: Cool. So we’re all in each other’s fan club.

Anil: Yeah.

Paul: That’s nice. That’s good. That’s positive. Anil, I’ve heard you on many podcasts and everybody is like, “What do you actually do?”

Anil: Yeah, yeah, yeah.

Paul: I’m going to tell people what you do.

Anil: Uh-oh.

Paul: OK?

Anil: No spoilers. I would be very excited to find out.

Paul: I want to see if I can get it right.

Anil: OK.

Paul: OK, ready? Anil is a person who’s best known because he has a very, very large platform. He’s got half a million followers on Twitter, so on and so forth. When people see Anil, that’s often…half a million people see that platform and they’re like, “I guess that’s that guy.” What does Anil actually do? Well, I’ve known him for many years. What he does is, he does help an enormous number of media companies. He advises them, he works with them, he’s on the board of places like Stack Overflow. He’s an advisor, that’s one of the things he does. He actually has a tremendous understanding of technology, down to the roots. He started as a Novell NetWare guy in high school.

Anil: Wow! That’s true.

Paul: Setting up networks for small businesses in rural Pennsylvania.

Rich: Spilling the beans, here.

Paul: Yeah. This is somebody who goes deep on tech. Still knows PHP, still can hack his way around a web page. He got very into blogging early days, which meant that he met every publisher, every media person, and has really good credentials. You need to get an app strategy out, you’re a big organization: he’s one of the people you might call.

At the same time, over the last, I would say probably five to ten years, but really in particular in the last couple years, maybe because you have this platform, you’ve been trying to become more engaged with the world around you. You’ve been worried a lot about issues of access. I’m imagining maybe this is because you had a kid?

Anil: That was part of it, for sure.

Paul: And you’re trying to become more of an activist. More of an actor in the world to increase access to technology. How’d I do?

Anil: That’s pretty good! That’s pretty good.

Paul: OK. Because people talk to me about you, because you’ve got a big profile, and they’re like, “What the hell does he do?”

Anil: Yeah. Yeah.

Paul: And I’m like, “He does … stuff. He’s a person with a job who does work.”

Anil: Yeah, I do real work. But I’ve always, somewhat, deliberately been cagey about it in my social media persona for a lot of reasons. One is, if you do anything nominally about making tech or the world more inclusive, you’ll get harassed and attacked. I’d like to spare my colleagues and co-workers from that, to some degree. And also, it’s really interesting to see people project onto me, or anybody else that’s on the internet, their view of what you are. That’s been very useful to me.

Paul: I think also, one of the things I’ve noticed over the years is that you go all the way in, and you go in without irony. It took me five years to be like, “Oh, I’m talking to people on Twitter. These are real relationships that I’m forming.” You were there pretty much on day one.

Anil: I mean I think … and again, a lot us that were early to social media back when it was still called blogging, you didn’t initially think it was that. You didn’t think you were going to meet people, and then Rich invites you to coffee, and then they become real people. I had a couple experiences really early on, which you guys would be probably familiar with but most folks have completely forgotten about. One was we made a early blogging tool called Movable Type. And until —

Paul: And this would be what? 2000 …

Anil: The tool came out in 2001 and I was helping the co-founders that had built it, and then I started working on it as my job in 2002.

Paul: And we should give context to people. Blogging tools didn’t exist for the first five or six years of the web.

Anil: Right.

Paul: You had to just build pages by hand or use very, very expensive CMSes.

Anil: Right. Blogger and LiveJournal came out in ’99. They were the first wave of usable tools for normal people. Then what Movable Type did in 2001 was like, “This is the serious power tool.” That was just an interesting, and also, like, the medium itself had become interesting, so it was the tool that would later go on to be used to build Gawker, and Huffington Post, and all those early sites.

But to me, I was just sort of like, building the tools, trying to figure out, “Is there some kind of business here?” This is such a crazy thing to talk about now, 12 years later. We decided that we would charge for some versions of the product.

Paul: [heavy sigh]

Anil: If you were trying to reach a certain number of people or you had a certain number of co-writers on your site, or whatever it was. I mean this sounds nuts now, but we basically said, “Well yeah, if you have more than, like, five people writing on your site, we’d like you to pay $90 for this app.”

Paul: Again too though, for people, like: getting money through the web was hard. There was no app store. There was no nothing.

Anil: No.

Paul: It was literally you’re going, “We need that $90 now.”

Anil: Yeah.

Rich: You know what’s funny about this is…you see this a lot, and I went through it personally, actually. You start something and you believe in what it does —

Anil: Or what it could be.

Rich: Or what it could be. You’re really not checking back on a spreadsheet and thinking about the business plan. You just feel like, this is transformative. This thing is going to be —

Anil: It needs to exist in the world.

Rich: It needs to exist in the world. And then what happens is ABC calls you up and says, ”We’d like this tool throughout the organization.” Then you have no plan.

Anil: Yeah.

Rich: Like large companies give you a call and they’re like, “This is the real deal, but I need an approval process here.” There’s no way to approve what someone else wrote. Then you pause and you say, “Well, that’s not what we are. We are here to change the world in a grassroots sort of way.” But then you pause and you’re like, “Whoa! Hold on a second. These guys are willing to pay some real dollars.” Then you start backing into a plan —

Anil: Yeah.

Rich: And you have no idea what you’re doing.

Anil: Well, and there were no comparables. Now, if you’re like, “We’re going to charge for social media,” it would be like, Facebook would have zero users if you had to pay for it, right? There’s that thing. But what we were looking at, what I remember distinctly, was I was like, “Well how much does Macromedia Dreamweaver cost?” And I was like, “That’s $500. How much does Microsoft FrontPage cost?” And it’s like, “Oh, well that’s $250.”

Rich: There’s like no research.

Anil: Right! So, I was like, “So, well we’re way cheaper than that; therefore, we’re better.” It was not this complicated market analysis. And then we asked people, “Oh well, you know, how many people do you have writing on your site?” There were like, one, two, whatever. Look, if you have like five, we’re going to ask you to pay. It was like one percent of users would be affected. How could one percent of users — in retrospect, it’s obvious: people care about the potential. They all thought they were going to have a site with 500 writers on it and they were going to be super popular, and so they were like, “If you make me pay for that capability, then you’re constraining my expressiveness or my potential.”

Long story short, we changed the license on a piece of software and got probably the first-ever brand shit-storm in social media. I don’t think — because nobody else, by definition, all of our users were people that were bloggers and nobody else had had a customer base that was true for.

Paul: It’s true, I remember this was the ultimate betrayal.

Anil: Yes.

Paul: And you were charging for software on the internet.

Anil: The equivalent of Twitter trending topics, back then, was blogdex, which was Cameron Marlow’s research project at MIT around the most popular links and topics on blogs at the time.

Paul: And for people who don’t remember, that’s B-l-o-g-d-e-x.

Anil: Yeah, it doesn’t —

Paul: It probably doesn’t … When it sounds, when you said it, it was almost like mixing decks.

Anil: Yeah, yeah, yeah. ‘Dex’ like index. We were the trending topic for like a week, because there wasn’t that much going on in social media. The pattern that you actually, I think we all know really well now of like, some brand tweet some horrible thing during an awards so and everybody is like, “Oh, that was racist.” Then everybody blows up. Then they send an apology, and then they make a donation, and then the world spins.

But the pattern wasn’t set yet, and we weren’t familiar with it yet. 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.

Paul: Oh, yeah.

Anil: You know? It was an epiphany for me. I mean, it was miserable at the time. We were all literally sitting at our desks crying. Then it was like, “These are people.” They had projected relationship onto me or us, or this app or whatever. It was meaningful to them and they had felt betrayed, or, Paul, your formulation, the “Why wasn’t I consulted?” It was at emotional level. It wasn’t your features or your design, or 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.

Paul: That’s right, that’s right. Yeah. I remember that.

Anil: That was revelatory to me, because it made me understand what the internet was.

Paul: What was the internet, then? What is that?

Anil: Everything prior to 2003 or so, of the internet, was just getting set up. It was just plugging in the wires. And what switched, you know, Friendster was 2003, and blogs start to take off, and all these different things. 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.

Paul: Right.

Anil: Right? 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.

Paul: Or even finding original things.

Anil: Yeah, exactly. Right? There’s this very interesting … It’s a communications tool. And in a way, I think a lot of us that had computers when we were kids, like in the 80s … I had a Commodore computer, a VIC 20, and then a Commodore 64 for years where most of what I did was not online. What would you do with a computer that wasn’t online, today?

Paul: See, I would love it. I would love it. I want to go —

Rich: Get some stuff done.

Paul: Yeah.

Anil: What would you do? Ultimately, you want to get back on. You’re talking about flipping the switch off for a minute so you can write.

Paul: I’m not though, because —

Anil: Or, like, be on an airplane.

Paul: What I remember was that you had to find new ways to be creative with the old machines. You had to … You were like, “OK, I can draw with this.” But the drawings were really ugly.

Anil: Primitive.

Paul: You had to figure that out. Write a little program or make a little music. It didn’t translate outside of your relationship with the computer, because it was like, “Woop-woop-woop-woop woop-woop-woop.”

Anil: But for computer enthusiasts, late 80s, early 90s, the switch flips when you get a modem and you get on CompuServe, the AOL or whatever, and —

Paul: What’s the difference between 100,000 people and 100,000,000 people.

Anil: Yeah. Yeah. And it’s their communications tool. That was the thing that was like, “Oh, the internet.” I’d been learning HTML and I knew web pages, and I could make the little whatever thing, doohickey move around on the screen, but all of that was just leading up to this becoming a communications medium.

And so, like, that switch flipped, and realizing there were real people on the other end. There was that one thing with the, you know, we made the software change and a bunch of people got mad. Then the Iraq war was around that time and I had sort of weighed in, as one might expect, on that, and got targeted by a site, somebody who was vehemently pro-war. And they — you know, again, the kind of pattern that you see all the time today, but they called my employer and harassed me on the phone at home, and they published my address, and they did all these things that we see, whatever, Gamergate or somebody do today, but in 2003, 2004 it was shocking.

Paul: It was. I remember I had a weird stalker back then. You just couldn’t make sense of it.

Anil: Yeah. It was like these worlds never crossed. There was no such thing as IRL intersecting with online, and in such a visceral way of like, “These are real people.” These two examples I know about people being angry. There was also like … somebody sent me a spatula off my Amazon wishlist, which is still the spatula I use today. There was all this evidence of actual humanity on the other end, and all of it really quickly changed me into, “None of this is a joke. None of this is casual.”

And we ended up — I remember, I was working on Movable Type, and I was working for a woman named Mena Trott. She had been the founder and CEO. I guess this was ten years ago, now. She did a TED Talk, before TED was the TED it is today. They weren’t on YouTube yet and there weren’t videos online or whatever, so it was for that cabal of people that were old-school TED people. She did this talk about, essentially, civility in the blogosphere, which is what we talk about of harassment in social media today.

And it uncannily echoes Monica Lewinsky’s talk last year about being targeted online by people, and how people get harassed and abused. I don’t know how it was received in the room, but in the blogosphere it was a lead balloon. People were like, “What are you talking about? What do you mean? Strangers on the internet are going to harass you? Why are you even worried about this?” It was utterly dismissed. Utterly dismissed.

Rich: Interesting.

Anil: You have a young, I don’t know … Mena, legally, would qualify as being Latina. I don’t know how she personally identifies. You have this young woman in her early twenties who is telling people, “I built this technology and I know how people can misuse it, and we need to work on fixing this.”

Paul: At that stage, in that world, she may as well have been an extraterrestrial.

Anil: Yeah.

Paul: There’s just —

Anil: And you had the most powerful people in the world at TED, and they were like, “This doesn’t matter to us. We don’t care.”

Paul: No. I mean, it’s a young woman talking. She’s talking about harassment in the “blogosphere”. Culturally we just don’t understand that.

Anil: No.

Paul: We still don’t. We’re still having a lot of trouble with it.

Anil: Right. Right. It’s an interesting conversation for me to have of … I’m pretty politically liberal and generally agree with a lot of the policy proposals for Bernie Sanders, and yet, his adamant supporters who refuse to be called Bernie Bros came after me on Twitter and … I don’t really care about it, and it wasn’t real harassment, but it was annoying. And it was still explaining 101 concepts to them.

If I would have said to them, literally, a decade ago, we’re having this exact same conversation about when a bunch of people swarm on somebody and publish their private information, and do these behavior or these things, it’s bad, and you shouldn’t do it, and it has real costs, or real impacts, on people’s lives. I’m in a good position where it’s not going to affect me too much, but when you do this to ordinary civilians they’re going to be troubled by it. And I realized there’s no — I mean this is true broadly. There’s not medial literacy broadly, but there’s no literacy and fluency about it; because the tech industry refuses to learn the lesson.

Paul: It also won’t acknowledge new users. There’s no FAQ capacity anymore.

Anil: No, there’s no onboarding.

Paul: There used to be this sense, if you joined the community you’d read the rules.

Rich: Yeah. There’s a separate goal; which is, “Lower the barrier as much as possible.” Get you on Instagram in 0.3 seconds.

Anil: Yes. Everything has to be friction-less, right?

Rich: Exactly.

Paul: Friction-less.

Anil: Friction’s really good. It’s really good. Having barriers up makes people behave better. It makes them want to do better. You see what you get … If you’re like, “We just want to reduce any kind of obstacle to anybody showing up, with no sense of norms or values about what this place is,” you get what have. Even if you wanted to learn the lesson. This is the thing I think about. Let’s say you were a product designer at Instagram, at Facebook, at Whatsapp or whatever, and you’re like, “I want to make this a happy place.” You go to Stanford. You graduate at the top of your class in CS. You’re like, “I want to make sure all the products I make make the world better and everybody who uses them is happy.”

And you’re like, “Is there any prior art or prior history of how building social tools affect people’s lives?” And they’re like, “I don’t know.” Since the beginning of history, nothing’s ever been done before? If you want to know the history, every single detail in every line of code of the compiler for the C language, you can can see the entire history back to the original version, right?

Paul: Right.

Anil: It’s all open source. Documented to day one. And if you’re like, “Well, has anybody ever made a tool for photo sharing that people have abused to stalk each other?” You’re like, “Never heard of it. I don’t know. There’s no prior art.”

Paul: Yeah, I’m trying to think. There was a social patterns community, a little bit; like Christian Crumlish —

Anil: Sure.

Paul: There’s some stuff out there; but no, nothing that —

Anil: Right. You and I with encyclopedic recall of the most obscure corners of social software —

Paul: One or two things.

Anil: Can recall one or two things from people who are not part of the conversation anymore.

Paul: Right.

Anil: Brilliant, wonderful people who I love and respect who are not part of the conversation. And the people who do lead on this, Paul Graham at Y Combinator, or Marc Andreessen at Andreessen Horowitz, are willfully illiterate in it. Not, like, they can’t even claim, “Oh, I never heard of these old software.” They helped fund it. They were around then. And they’ve worked to erase the lessons learned about how you treat people well in the name of, “We need to onboard people faster.”

Paul: It’s a barrier that the hyper, hyper, hyper, hyper, hyper, hyper —

Rich: Growth and unicorn and how do I reach a billion… I mean, Instagram’s success is defined by the fact that they eliminated steps.

Anil: Yeah, sure.

Rich: There weren’t any tools where you could take a picture over here, bring it over there, store it here, and then push it up there.

Anil: And to their credit, Instagram’s credit; Instagram’s not the worst place in the world. It’s generally a happy place for people. There’s not a ton of abuse.

Rich: For the most part. I have to say, I am by no means a Facebook expert; but I feel like they were very wary of where this could go south. I don’t even think for altruistic reasons. I think they were wary of it for business reasons, frankly.

Anil: Yes, yeah. Absolutely.

Rich: But yet this is a place that seems to somehow, in very subtle ways, keep its act together in terms of what can happen on there. I think this was one of the arguments for the whole upheaval of Twitter. They just weren’t on top of this part of the whole thing. Facebook really was, and Facebook is a whole other scale. I think they’re thinking a whole lot more about it now….

Anil: Yes and no. There was a happy intersection of Facebook’s business interest with some practices that reduce the worst kinds of abuse.

Rich: Mmm hmmm.

Anil: That’s great. I don’t think it was intentional. I don’t think they were like, “We want to prevent abuse at all costs.” I think they were like, “If we made it possible to search a equivalent of a hashtag all across Facebook, that’d be really hard and expensive, so, we’re not going to do it.” I think a lot of it is this very pragmatic, “We limit the conversation to you and your friends, because that’s actually a lot easier to do.”

Rich: Yeah.

Paul: All right. We’re talking about harassment online. You’ve received it —

Anil: Sure.

Paul: — steadily. You’re at an inflection point. It sounds like you’re going to go hard on being an advocate for people.

Anil: Yeah. What I realize is as geeks we won. Those of us that make software and technology had thought, “Tech can change the world.”

Paul: When do you think we won? I think we got to pin this down.

Anil: That’s a good question. Probably 2007.

Paul: OK, I was thinking a couple years later. 2007, what happened?

Anil: It might be 2008. The iPhone.

Paul: Oh, OK.

Anil: The science fiction moment of a computer in your pocket that you touch the glass and it can give you access to any information anywhere in the world.

Paul: Steve Jobs as a pop culture figure.

Anil: It will not just be about accessing database. It is the driver of major mainstream art culture, right? And music, and films. If you are a creator in any endeavor; if you write books, if you make films, if you make music, if you make albums, you still have to bend to the person who made the piece of glass with all the information in it. Culture, broadly, society is basically fenced in by three pillars here. One is technology in its own sake. The second is arts media, culture, and entertainment, right? And publishing. All those things. That’s the grist for the mill. The thing we talked about, it’s how we express ourselves. And then there’s policy, and politics, and governance, right?

And in the same time frame, 2007, 2008, you have technological sophistication and superiority being a primary decider of political power: who has it and how they manage it and how they collect funds, all the things that they do. Even starting when we had the earliest inklings of tech dominating policy decisions by routing around them. Uber starts then, right, and they’re like, “Our solution to a regulation we find inconvenient is to ignore it.

Paul: Sure. Or litigate it away once we get enough money and power.

Anil: Right. So, if you control policy, and you control media, and you control technology, you control culture. And tech took over the other two pillars. So this moment arrives and you win. “All right. We can shape everything. We can influence everything. What are we going to do?” First we’re like, “We adamantly refuse to learn any lessons about social responsibility.” You know, if you want to get — you’ve got a law degree. You have to have an ethics class when you’re taking getting law degree.

Rich: There’s an ethics exam.

Anil: Right! If you’re in journalism school, you have an entire course on journalistic ethics. If you are in business school, you take business ethics. Most CS programs have no ethics curriculum at all. If they do have one, it’s probably a perfunctory oversight and has no insights to bear on, like, well what are the implications of this big data solution you’re coming up with? There’s complete abdication of any ethical training, any civics training, any context of social impact of the work we do. At the same time, we’re maximizing our ability to control society. That’s a problem, I think.

Paul: Fair enough.

Rich: Do you think it’s just because it’s early days? I mean, I don’t think there’s a secret plot.

Anil: No, I don’t think there’s a secret plot.

Paul: I think people don’t like when anything gets in the way of their personal hyper-growth.

Anil: Yeah.

Paul: I think it gets ’em real upset.

Rich: I also think we carbon copied the word engineer here to keep going, because we didn’t know what to call it. Essentially, it’s a hard skill.

Anil: It’s a bad analogy.

Rich: It’s a hard skill.

Paul: It’s a trade.

Rich: It’s a trade. You could sit here and say these same things about carpenters, maybe? No. So, why… I’m playing devil’s advocate for a second.

Anil: Yeah, but it’s not in that way.

Rich: It’s, you know, I’m an architect, or I’m an HVAC guy. Do you think I should take ethics training?

Anil: So actually, yeah. People who design cities, people who design buildings absolutely have ethical obligations that they teach each other about.

Rich: Yeah.

Anil: Here in New York, we have buildings that are trying to have a separate entrance for their rent-subsidized tenants, which is, like, “Here’s your poor entrance, here’s your rich entrance.” People are rightfully objecting. Boy, if you’re an architect, you probably shouldn’t be part of that. So, there are absolutely architectural decisions that impact society.

Paul: The ethics are baked in. My wife works in construction. The ethics are baked into the conversations she has. There’s a lot of unethical stuff in construction any moment.

Anil: Yes.

Rich: Right.

Anil: But you can shift it. I was working broadly in the construction industry when the ADA passed. You know, people were crying, “Oh, we’re going to put a ramp on everything, and it’s terrible.” And it’s like, we wouldn’t have the rolling luggage industry if the ADA hadn’t put ramps everywhere. There’s all these great benefits. Our strollers got bigger, and heavier for our kids. Now we have SUVs we push around. That stuff all happened because ADA genuinely made things far more accessible for more people.

The construction industry was not saying, “We’re going to actively break the regulations.” They were like, “Look, there’s an inspector. They might come and see if we don’t build the ramp. We got to build the ramp.” It wasn’t more complicated than that. Meanwhile, if you’re like, “We want to inspect whether Uber is complying with taxi laws,” they’re like, “Of course we’re not.”

Paul: What’s the goal here for you?

Rich: Disruption.

Anil: Yeah.

Paul: What do you want to do?

Anil: I want to re-rupt, re-rupt instead of disrupt.

Paul: Re-ruption.

Anil: Yeah, re-ruption.

Paul: Anil Dash, re-ruptor.

Anil: Boy, that’s a branding triumph. I think it’s very simple. I think we need to understand that choices we make in technology, features in our software, in our hardware, in our devices, directly affect society.

Paul: What? Like what feature?

Anil: There’s a lot of examples. One of the ones I’ve really gotten obsessed with, because of the tech industry’s really weird relationship with labor, is Postmates, which is like a ‘push a button and make humans do things for you’ app.

Rich: Yep.

Anil: Had a delivery service where they would bring you, I think, food and stuff.

Rich: Anything.

Anil: But I think this was particularly in the food feature that we’re going to talk about. They had tip menu where you could choose how much you were going to tip the poster, whatever the person is.

Paul: The post-mater.

Anil: Your mate.

Paul: Ugh.

Anil: I don’t know.

Paul: So, tip your mate.

Anil: Right. I don’t know how they brand their humans, but they have the person that was going to do the task for you. They change the default on the tip to essentially be zero. It had been twenty percent, they made it zero.

Rich: Mmm hmmm.

Anil: The average person who was working these tasks lost thirty percent of their income when that one menu screen change. I would assume most of the people who made that app and were responsible for making those decisions probably went to very good schools, had computers at home, went to top universities, probably went to Stanford —

Paul: We don’t even have to assume that though, do we?

Anil: We can check and —

Paul: People made this decision.

Anil: Right. What I’m saying is they had never had an experience with a job that relies on tips.

Paul: Whoever the cohort who made that did not feel the need to protect that.

Anil: That’s right. I want to point out how they got there, because I don’t think it was malice. I don’t think they were like, ”I don’t care about these workers. I think they literally don’t understand the condition of working for scale plus tips.

Rich: It could very well be that the engagement numbers weren’t very good.

Anil: Sure. It could have been —

Rich: “What the hell” —

Anil: If you have to choose a tip amount, there’s a tyranny of choice and it’s going to slow down the transaction .

Rich: It’s not even just that. It’s twenty-one bucks, and now it’s twenty-five. People are just starting to get the interface that I have the option to dial it back down to zero. They’re saying, “What? This is a hell of a fee you’re charging me here.” Postmates is a startup. It probably raised a couple million bucks —

Anil: Probably.

Rich: And they’re trying to survive. This is sounding like —

Anil: You’re giving me a view into the beast.

Rich: Well, I’m trying to frame this, because I don’t think it was, “To hell with the delivery guys.”

Anil: No, I don’t think it was malice at all.

Rich: I think it was, “The numbers aren’t great. We got that meeting next month with the board.”

Paul: “Where can we cut?”

Rich: How do we get — you know Seamless made a big change with tips by the way, recently. And if I’m not mistaken, it went from a free-form field to —

Anil: Percentage.

Paul: Yeah, 15, 20.

Rich: Percentages, and there are selections.

Paul: It’s more work to put in a custom tip than to select —

Rich: To select. The default select, if I’m not mistaken, is a lot higher now than it used to be.

Anil: New York City taxis did the same thing. They have a thirty percent option, and I’m like, “I love taxi drivers, and I’m Indian, and I’m not giving you thirty percent.”

Rich: Oh my — $8…Used to be … you used to pay with cash. New York taxis pay with cash.

Paul: Yeah, and you just round up.

Rich: Eight dollars. You gave ’em a dollar. You give him a ten, you ask for a dollar back. That was —

Anil: Wow, you’re a monster.

Rich: No, I mean, this is how —

Anil: I never asked for a dollar back.

Paul: Yeah.

Anil: I’ve never tipped anybody less than $2 on anything.

Rich: We never processed —

Paul: What the hell? Who are you?

Rich: — the percentages —

Paul: Give him the ten!

Rich: I guess what I’m getting at here —

Paul: If it’s a dollar-sixty, it’s $9.60!

Anil: You’re just trying to gloss over the fact that you gave dollar tip.

Rich: Hold on a sec.

Paul: Why don’t you ask him for forty cents back.

Rich: I guess what I’m getting at here is that, defaults — this is to your point, but on the other side of this is, your ADA example is an interesting one, because it’s an independent third party that is advocating for particular a position that can’t even get in the room.

Anil: Mmm hmmm.

Rich: They either needed laws, or they needed press, or they needed something that was really going to force a hand here.

Anil: Good regulation.

Rich: Good regulation, that’s right. Ultimately, these are young businesses that are probably going to fail. The great majority of them will fail.

Anil: They’re in the process of fail.

Rich: They’re in the process of fail. They are just … it could well be, probably unlikely, that they just though….user experience person further down the line made this change, and nobody really thought about it.

Anil: Sure, but what they’re doing is they’re externalizing their risk, right? What you do in these cases is, those people who can’t survive on their tips are going to be supported by a safety net that’s paid for by the rest of us, not by their VCs.

Rich: You’re right. You bring up a great point here, but I’m going to go four degrees over and argue that Postmates needs to be careful, because the army that they’re sending out there to make Postmates successful will turn on them.

Anil: Yes. Yeah. If they’re empowered to.

Rich: If they’re empowered … Well, there are going to be other apps. I think there are fifty of these delivery apps. I think what they have to be careful … I think that is the better case you’re going to make to Postmates, frankly.

Anil: They’re going to choose another app?

Rich: No, I think when you’re in that room and you get to be in front of that board, I think telling them that you never worked for tips and you don’t understand what they’re struggling with here is not going to fly. What will fly is, “Listen, you better be real careful, because that army that you need to be successful will flee.”

Anil: Those are the same thing, and those are parts of the same argument. For me —

Paul: Who are you going to try to convince? Are you going to try to convince capitalists, or are you going to try to —

Anil: There’s an interesting thing here, because I think the crux of what you’re saying is, ”Well, if you make the economic argument, they’re going to be more persuaded by that.

Rich: It may not…yeah.

Anil: One of the choices I’m trying to make more frequently these days is to deliberately not frame ethical choices based on the economic argument. For example, diversity and inclusion in tech. I think we make more money and are more profitable in companies where we’re more inclusive and we have a broader range of people working for us. The data are there. The evidence is there. That’s fact.

Nevertheless, I don’t ever want to make the case for diversity and inclusion in tech based on the fact that’ll it’ll make the people who are against inclusion richer. That is not interesting to me. That is not the framing … I’m not willing to concede the ethical and moral underpinnings of the argument. The same is true for these workers. Screwing them out of their tips because it makes your user interface simpler is wrong. It’s also bad for business, but I don’t care about your business. I care about you doing something wrong to people who don’t deserve to have something wrong done to them.

Rich: Would you agree that that’s not going to fly, to a company?

Anil: Yeah. Yeah. Especially if we can give tools to the workers to organize with each other, where they can pass the word that Postmates is going to screw you —

Rich: Maybe you are organizing that ADA. Maybe you are creating —

Anil: I hope to.

Rich: — that third-party organization that is going to, essentially, provide either guidelines, at the most extreme, laws that they have to stick to.

Anil: I think anything short of laws, they haven’t responded to. Even in the case of a lot of these companies, the laws they didn’t respond to either.

Rich: Right.

Paul: What is a day, then?

Anil: That’s a good question.

Paul: I know what you do. I think I’m the only person in America who actually knows what you do. What are you going to do now?

Anil: The goal is that the folks who are building, whether it’s the founders of a startup that are building something cool and creative, or the industry leaders who have the money and are writing the checks, to independently be thinking, “Boy, did we anticipate how this impacts the most vulnerable people, the most marginalized people, because, either now we’ve been reminded enough times that we know that’s what we should do, or boy, are we going to get the shit kicked out of us on the internet if we don’t.” Either way, carrot or stick, I’m OK. As long as they are thinking, “You know what, there is no way we’re going to be able to get this thing out there in the market and fulfill the potential of our technology to change the world without us thinking about the people who have the least, and have the least access, and who we typically haven’t served in the past.

Paul: OK. How are you going to do that on a Thursday? What are you going to do?

Anil: I’m very fortunate now, with the size of my network and the people I’m connected to. I get a lot of inbound, a lot of people saying, “Boy, here’s a thing. You got to go fight with this person.” People call things to my attention that they want to get amplified and they want help on. Ninety percent of the time I say, “Here’s the person who runs it. I’m going to introduce you and connect you, and I think they want to do the right thing. Let’s help them. If you need resources, I’ll help you get them.” Ten percent of the time, somebody stonewalls. Then we bang the drum. That’s pretty fun too.

Paul: Somebody wants to help you.

Anil: Oh, gosh!

Paul: What do they do?

Anil: Don’t help me, I’m fine. Look at the apps and the tools and the tech that you use everyday. You’ll instinctively know if you think about it for thirty seconds, “Boy, they’re screwing up in this one way.” “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.

Paul: All right. Come back soon and tell us how this is going.

Anil: I will. Thank you so much for having me.

Rich: Thank you, Anil.

Paul: That was Anil Dash talking about his new life as an advocate for social change by critiquing technology. Anil is many things. You can find him at dashes.com and you can also see him at @AnilDash on Twitter, where you’ll be one of about a half million people keeping an eye on him. Anil, thank you.

Anil: Thank you, guys.

Paul: Thanks for listening everyone. Rate us on iTunes and let us know if you need anything. Just send us an email. Contact at postlight.com. Check us out on postlight.com, our website. We’ll talk to you soon.

Rich: Bye-bye.

Paul: Bye!