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Episode 11 May 3, 2016 | 39min

Gina Trapani: Coder to Lifehacker and Back Again

Paul and Rich talk to Gina Trapani—Lifehacker founder and new Postlight employee.

Show Notes

This week Paul and Rich talk with Gina Trapani, a programmer, the founder of Lifehacker, and one of their newest employees. Gina talks about her journey from coding to the technology and lifestyle blog Lifehacker — and about her decision to return to the programming fold. She also reveals why she took a job at Postlight. (spoiler: simpler tax forms!)

Paul Ford: Well, welcome back, friends, to Track Changes, the official podcast of the very official Postlight product shop; web agency; engineering, product management, and design firm in New York City. I’m Paul Ford and I’m here with my co-founder and co-host —

Rich Ziade: Rich Ziade, you’re talking weird.

Paul: Really?

Rich: Yeah.

Paul: I’m just being…I’m just doing a podcast.

Rich: It sounds…OK, there you go. Now you just fixed it.

Paul: [incoherent mumbling] …real chill.

Rich: There we go.

Paul: OK. Well, Rich, hmmm, all right, is this good?

Rich: Mmmmm, you sound very public radio right now.

Paul: Oh God. Just. All right, Gina Trapani’s on the program today.

Rich: That’s good news.

Paul: You know, she’s an interesting person. I’ve known her for a while. I knew her when we were baby bloggers in Brooklyn.

Rich: Really?

Paul: Yeah! We used to walk around Prospect Park together and talk about the internet.

Rich: No kidding. Like, early 2000s?

Paul: Like in our twenties, early twenties.

Rich: No! So that’s 196 —

Paul: 4.

Rich: Seriously. That’s what, early 2000s.

Paul: Early 2000s.

Rich: Wow.

Paul: Yeah. Like, the earliest possible days.

Rich: That’s a big deal.

Paul: So Gina is an old-school blogger and programmer.

Rich: I have this fear, can I just share the fear?

Paul: Go ahead.

Rich: That we are, we’re becoming the oldies station of tech podcasts.

Paul: [laughing] A little bit.

Rich: And so I just want to be careful with it, and I want to talk about wearables.

Paul: OK, let’s talk about wearables —

Rich: So that we are relevant and modern.

Paul: The Internet of Things, which probably isn’t even called that anymore. Anyway, let’s stop our idle chit-chat —

Rich: Yes.

Paul: — and say hi to Gina. Hi Gina.

Gina: Hi.

Paul: Rich, are you going to say hi?

Rich: Hello.

Paul: There we go.

Gina: Thanks for having me.

Paul: Well, you didn’t really have a choice, did you? [laughter] Because in between the ten weeks of us making a list of people we’d like to have come in and us sitting down to record this, something surprising happened.

Gina: Something wonderful and surprising happened.

Paul: Which is that we hired you to work at Postlight.

Gina: Yes! And this is my first week.

Paul: That’s right. We’ve already started to exploit you for marketing purposes. [laughter]

Rich: Oh boy.

Paul: So what do we know about Gina Trapani? I know that she was a blogger and then something magical happened to her in the 2000s which is that a man named Nick Denton asked her to write some Java code to create an RSS-style reading experience called Kinja.

Gina: That is correct.

Paul: I remember being really impressed because I was like, “You can program Java?!” And that was the first version of Kinja. If you’ve been to Gawker and survived you might have seen something called Kinja there today. This was a very different —

Rich: It’s still there.

Paul: It’s not this, though. This was a very different product.

Rich: Right, but they still call —

Paul: They call their commenting system Kinja. What was the first Kinja? Do you remember?

Gina: Yes, it was a blog reader. And Nick just really liked the name ‘Kinja.’ And in fact, I was in the conversation, it was four of us sitting on a couch, coming up with the name for Kinja, and when someone said Kinja, we all loved it.

Paul: Wow.

Gina: I don’t know. I don’t know. So —

Paul: This is how technical debt is born.

Gina: [laughing] I don’t believe that one line of code that I actually touched is still in the commenting system Kinja. But the first Kinja was a blog-reading app.

Paul: And the idea was like, if you were too…something to not get your own RSS feed up, because blogs weren’t on, like, automated platforms like WordPress or…

Gina: Right. That’s right.

Paul: So they didn’t, by default, have RSS feeds —

Rich: Needed the tools.

Paul: Yeah. Somebody had to make you an RSS reader.

Gina: The software did not the RSS. It used the HTML pages. Actually very similar to Readability. We had this giant parser that would pull in web pages, blogs, and then display them very much unlike an RSS reader. Back then it was like, Bloglines —

Paul: Right.

Gina: — was that, you know, inbox-y kind of feel, like ‘you have this many unread.’ Kinja was just kind of this stream of, you know. And 37signals did the design for it.

Paul: Whoa.

Gina: Yeah.

Rich: I think I remember this.

Paul: Well this was very early, this was the Gawker network was going to expand, it was like, just Gawker.

Rich: Yeah.

Paul: I think, and like maybe one or two other sites.

Gina: It was Gawker and Gizmodo, I think, at that time.

Paul: Yeah. And they were going to expand and do all this other stuff. I know we are at risk of being the oldies station of the podcasting world, but you mentioned a product called Readability, which Rich created, which parses the web and makes a nice clean version of pages. People compare it a lot to Instapaper, or to Pocket. It’s in that world.

Rich: Yeah.

Paul: And this problem has been there from the very earliest days, is that we make these pages and then we can’t really read them or do things with them.

Gina: Yeah, the semantic web was a dream —

Paul: Well —

Gina: — that somebody I know had.

Paul: Burn that down. But let’s move on from that. So you’re in there in the early 2000s, trying to make a more readable web, funded by Nick Denton, and what happened to that?

Gina: You know, we built it, and it mostly worked, and it was really pretty, and you know, we had, like, channels. We called it a mix tape. It was like a mix tape of blog posts. Like, let’s see all the blog posts about music. Let’s see all the blog posts about movies.

Paul: Because we had no metaphors back then.

Rich: Oh it’s so funny. The terminologies, like, is it a channel? Is it…

Gina: A vertical?

Rich: It’s so funny. We could debate for hours.

Gina: It was a stream, we were very philosophically excited about the idea of a stream.

Paul: I remember working on a PowerPoint deck that was exclusively about whether something should be a “hub” or a “portal.” [laughter]

Rich: Right, exactly.

Paul: It was like, ’99. It was bad days.

Rich: I’m just going to throw out the word Snapchat.

Paul: Snap — yeah. No. Snapchat.

Rich: In the middle of this discussion.

Paul: Whisper. [laughter] Yeah, we just have to get keywords in for the transcript so…Facebook! [laughter] All right, you’re programming in Java — and I remember, also, I was very, you were like using Eclipse. You were very serious.

Gina: Oh yeah. Eclipse and CVS. We were like, we were hardcore. Well Mark Wilkie, who is the recently-departed CTO of Buzzfeed —

Paul: That’s right, Buzzfeed —

Gina: Actually —

Paul: Built that platform.

Gina: Yeah, and he was really, he was and continues to be really a mentor for me. He had this whole system, and I came into Kinja as an intern, I think maybe unpaid, or very little paid at first.

Paul: Well, this is a tradition at Gawker Media in the early days.

Gina: Yes.

Paul: Yeah.

Gina: Yes indeed. I came upon Kinja because back in that time, the old time, there were a few New York bloggers, many of whom I really admired, and Meg Hourihan had posted on her blog, Megnut, that they were looking for an intern, and I had met Anil Dash, and said to Anil, “Hey, can you introduce me to Meg, because I want to interview for this internship.” And they were like, yeah. And I was like, so happy to barely get paid.

Paul: Sure.

Gina: Because I got to be in a room with these people who were like, legends in my mind.

Paul: That’s right. Meg had been one of the people who worked on Pyra, which was the first sort of serious blogging engine.

Gina: Right.

Paul: That was Ev Williams’s company as well. And he went on —

Rich: Eventually became Blogger.

Paul: Became Blogger. Blogger was one of the first times that, like, everything got serious.

Gina: Yeah.

Paul: We’ve had a lot of these, where it’s like, “Hey we’re all kind of fooling around,” and then, like, someone showed up and was like, “Yeah, we can do it this way, and everyone can participate.”

Gina: Yup.

Paul: So Kinja launches — I remember, wasn’t, like, the launch was good. I remember using it and liking it, not fully getting it, and then —

Gina: Yeah.

Paul: — it just, it was one of those products that didn’t thrive in that form.

Gina: That’s right. You know, it was a product I was really proud of, and we worked hard on, and people liked, but people didn’t love it. Like, people weren’t there, checking it every day.

Paul: Honestly, that was probably a great experience as an intern, to know that that pattern exists, right?

Gina: Yeah.

Paul: I always wonder about people who experience success out of the gate, because it’s incredibly, incredibly rare.

Gina: It’s like, oh successful people can build things that, like maybe aren’t, aren’t the hockey stick, aren’t a huge splash.

Paul: Yeah.

Gina: That was a really good lesson for me, at that point. And so during the course of building Kinja, I was having lunch with Nick, and this was like 2004, and the term “lifehacks” had been uttered, by —

Gina: and Paul in unison: Danny O’Brien.

Gina: Yeah, at ETech, in San Diego, which was also this like, mythical land —

Paul: I’m part of that talk!

Gina: Oh that’s right! You are part of that talk.

Paul: I have a very —

Gina: This is a small world.

Paul: Yeah, someone wrote me and was like, “How do you organize your life?” And I sent, like a screenshot of my text file.

Gina: Mmmm hmmm.

Paul: That I used. And that was this guy Danny O’Brien, who we all still know.

Rich: So he coined the phrase?

Gina: Yeah, he coined the phrase “lifehacks.” It was a talk he gave at ETech. It was called, “Lifehacks: The Secrets of Alpha Geeks.” Something like that.

Rich: OK.

Gina: And Cory Doctorow was in the audience and took notes in a text file, which is very appropriate —

Paul: So he was, he’s from BoingBoing.

Gina: He’s from BoingBoing.

Paul: And a sci-fi author.

Gina: And BoingBoing does this post, like, “Hey, Danny just did this mind-blowing talk about how alpha nerds script their lives. And he called it ‘Lifehacks.’” So Nick and I were at lunch —

Rich: It’s such a great term. It’s a good term.

Gina: Yeah, it was. And Nick said, “I registered lifehacker.com.” And I was like, “It was available?”

Paul: Mmmm hmmm.

Gina: And he said, “Yeah.” And I was like, “Who are you going to get to write this thing? Because here’s, like, ten post ideas that I have.” And I just started being, like —

Paul: But you’re a programmer, not a writer. You were never assuming that you’d jump and just start writing —

Gina: Oh, no, the idea of being a professional blogger, I mean, Liz Spiers was doing Gawker at that time, and like, she was like royalty. I would have never —

Paul: Right.

Gina: But I was like, “There’s this app that lets you mount your gmail storage as a drive on your Windows desktop!” [laughter] I mean, stuff like that.

Paul: Because that’s the thing. When we started hanging out, you were just such a nerd, and it was great! It’s hard to find true nerds, you know? [laughter] You’re one.

Rich: Oh yeah.

Paul: Deep down Rich — if you get Rich into a corner, he’s also a nerd and a lawyer, so it’s a disaster.

Rich: It’s a disaster.

Paul: You’ll get excited about like, some aspect of contractual law, and you’ll be like, “This is actually REALLY interesting!”

Rich: Yeah, it’s terrible.

Paul: Yeah.

Rich: It’s terrible.

Paul: So anyway. So you are all excited about all these different things. You’re like, “Lifehacking. I’m gonna — ”

Gina: I want to talk to this writer, because I’ve got ideas to pitch.

Paul: And then Nick went —

Gina: “Uh….do you want to write it?”

Paul: I can underpay you. [laughter]

Gina: Why not?

Paul: Yeah.

Gina: And at that time I was writing my personal blog, which was very emo. It was fashioned after a site that I read called ftrain —

Paul: Yeah, yeah.

Gina: — that I found, I was so inspired by —

Paul: There were a lot of emotions. We were all in our twenties.

Gina: It was very emotional. You know, it was like, post-9/11, mid-twenties, my friends all just got laid off from their jobs, the city’s a really sad place, I don’t know what’s happening.

Paul: That’s true. No one had any work in like 2002, 2003.

Gina: Nothing. Everyone had gotten laid off.

Paul: Yeah.

Gina: Like I watched my friends get laid off —

Rich: Everything paused. It sort of just paused.

Paul: I made like $18,000 in 2002.

Rich: Also it’s worth noting dot-com blew up about four months…like the prior nine months before 9/11, the whole bubble burst, the whole dot-com bubble, like pets.com and all that bullshit. So it had already melted down, and then 9/11 happened, and everybody just sort of…dispersed. It seemed like everybody paused until about ’03, ‘04.

Gina: It’s true.

Paul: Well what happened, from what I remember with that, is that the nerds stuck in there, because we didn’t know what else to do?

Gina: Right.

Paul: But everyone who had been attracted to dot-coms with, like, MBAs, or, like, come out of real estate to get into this new, exciting thing, was like —

Rich: They bailed.

Paul: It’s done. I’m outta here.

Gina: Yeah.

Paul: And it was this huge bottleneck where pretty much everyone started to really know each other.

Gina: Yeah.

Paul: Like everyone was hanging out and — because you’d want to go and talk about information architecture at somebody’s apartment.

Gina: Yeah.

Paul: And I’d run into you or we’d run into — it was just a tiny little world.

Gina: At South by Southwest Interactive, anyway, was also tiny, and everyone knew one another.

Paul: And I know this feels like a history lesson, but it’s important because it’s like, you make this transition from programmer to writer and then you had a pop hit on your hands.

Gina: Yeah, it was, Lifehacker was a runaway hit, beyond anything that I expected.

Paul: And no one knew that those could really happen on the internet quite like that, like the runaway blog that was very successful.

Rich: Looking back, like if you put yourself in that timeframe, it’s pretty niche.

Paul: Yeah.

Rich: It’s not celebrity gossip.

Gina: I mean, it turns out that there are a lot of people sitting at their desks at their jobs feeling very distracted by the web and all of the little things and want to figure out ways to optimize their life and really believe, and to some degree I still believe this, that they can systematize common tasks that they have to perform over and over in a way that frees them up for bigger and better things, or saves them time.

Rich: It also feels good, right? You feel like MacGyver for a second.

Gina: Yeah!

Rich: You just feel like, “Well you know what? I just did something slick.”

Paul: Or very often it’s about getting something horrible, like your email, into something sensible, like a to-do list.

Gina: Right, like every day my email stresses me out and I don’t know what to do. I’m missing emails, I’m getting in trouble with my boss. Give me a system to deal with my email. And that was like, years of just talking about, and Merlin got in on that, I mean —

Paul: Merlin Mann.

Gina: Yeah, Merlin Mann did his “Inbox Zero” talk, which is amazing, just talking about email organization strategies, which was a thing.

Rich: People still talk about this today.

Gina: Oh, yeah.

Paul: Right, so there’s this point in the 2000s, there’s a big information overload, there’s all this stuff happening with the web, and there’s a very small core of people, and it became almost like a pop culture/tech moment. And I guess it’s sort of started to reach out outside of technology, right? Now were you in the whole, there was a whole scene around the Getting Things Done approach.

Gina: Mmmm hmmm. Yeah. I read the book, I appreciated the book. I wrote a lot about the techniques discussed in the book. You know, Getting Things Done is great, and I’ve interviewed David Allen. It’s aimed toward older corporate dudes who wear suits and have assistants, so I think a lot of the work that I did was sort of translating that for, like, your run-of-the-mill knowledge worker who’s sitting in the open layout and needed to get their TPS report together.

Paul: That’s interesting. Nobody really talks about that. Like —

Rich: Interesting. I didn’t know that. Because I’ve never read it, I didn’t know it was geared towards that.

Paul: But it makes sense, it was for the executive.

Gina: It is for the executive, exactly.

Paul: You’re an overwhelmed executive, get this book and get everyone around you on the folder system.

Gina: Yes.

Paul: So you are an advocate for personal productivity.

Gina: Yeah, I would say so.

Paul: Here’s what I would observe about you: I know a lot of people who talk about productivity quite a bit. From the very first days that you were on this beat, you have gotten your stuff done. Like there’s a lot of productivity books that never were finished, that were announced and never finished, which is a bad sign for a productivity book. [laughter] You’ve written two?

Gina: Three editions of the Lifehacker book.

Paul: Right.

Gina: And I did another book about something else.

Paul: What was the other book about?

Gina: It was about a product called Google Wave.

Paul: Beautiful product! Do you miss Google Wave?

Gina: [laughs] I don’t. I mean, I probably would have sold more books if it’d stuck around.

Paul: Yeah.

Rich: Let’s pause and tell everyone what Google Wave was.

Paul: Well, Gina can tell you.

Rich: Can you do it in a sentence?

Gina: Yeah. Google Wave was a product that Google released in 2009 that aimed to replace email and chat and document editing, or at least combine all of those activities, into one plug-in pluggable platform.

Rich: Got it.

Paul: Seems like we’re back there today.

Rich: Are we there today? With Slack and…

Gina: There’s so many products that have aspects of Wave baked into them. When Google Docs introduced live typing, where you can watch your collaborators’ cursors move across the page and edit, that was something they demoed originally in Google Wave and blew everybody’s mind at 2009 Google I/O. I mean, that was amazing that you could watch live typing in the web browser, and now Docs has that. We’re seeing it with Slack. We’re seeing it with Flowdock. Google Docs’s commenting features and embedding polls and things, those all come from Google Wave.

Paul: So let me ask you a question: if it was launched today, and with a modernized interface, if someone took the same feature set, launched it today, do you think it would find users?

Gina: No, I don’t. I don’t. Not without radically reimagined marketing.

Paul: Oh, OK.

Gina: I mean, I —

Rich: What went wrong?

Gina: I wrote a book, I wrote a book on this thing, and I just told you what it was in a sentence, you both looked at me like had three heads. There was just, the product never explained itself. I mean, the tagline was like, “This is the end of email.” So everyone’s like, “Cool.” But it wasn’t that. It wasn’t chat. It wasn’t document editing. It was a little bit of those things.

Paul: But you know, there’s an element to it, too — I remember using it and just, like, I didn’t have enough people in my network —

Gina: Right.

Paul: Now if you bootstrapped it onto like, if I take my Twitter social graph, or everyone who’s @postlight.com or whatever, it’s pretty easy to get into a collaborate space?

Gina: Yeah.

Paul: In Wave it was just like, “Oh, I’m here alone.”

Gina: Yeah, I mean, Google squandered their biggest opportunity, it was like, they’re launching a Google product, a bunch of people rushed in, it was invites —

Paul: Yeah.

Gina: The scarcity, people really wanted in, you felt special if you were in. But if someone sent you a Wave, you had to be in Wave to get it. There were no email notifications —

Paul: Right.

Gina: — on initial launch, so…

Paul: So you got into Google Wave.

Gina: I did. I got into it because I thought the technology was really very cool, and I got very excited to see that happening in a web browser.

Paul: So we’re back to, again, the fact that most products, I mean, who knows, you can throw some random percentage, right? Even at enormous scale, even with tons of resources behind them, and actually, you know, later we’d see this again with Google Plus, sometimes it just doesn’t work. You can put the absolute best people, the best resources, the best idea —

Rich: It doesn’t happen.

Paul: Yeah. It just doesn’t happen.

Gina: Well, and Google just has a couple of — they’re just kind of tone-deaf around certain things, particularly social, I would say.

Paul: I don’t even think that you saying that is —

Rich: Shocking.

Paul: — it feels like that’s objectively demonstrable. Google Plus —

Gina: Google Buzz.

Paul: Buzz was a —

Gina: Google Plus.

Paul: Buzz was an amazing disaster.

Gina: Google Wave.

Paul: That was like their sort of Twitter-baked-into-email thingy —

Gina: Yes.

Paul: [heavy sigh] But you know you’re right. They never got social.

Gina: No.

Paul: Do you have any sense of why? As an outside observer.

Gina: I mean I think they were chasing Facebook’s taillights from the beginning, and, I mean, I think Google’s really good at building utilities.

Paul: Right. It’s just like, Bing versus Google. Microsoft is like, “We can do that.”

Gina: Yes.

Paul: Yeah.

Gina: Right, exactly.

Rich: You just get the — you have this massive amount of resource. It’s like Microsoft, when they said they had to go into search. When you have that much at your disposal, you just walk up to the roulette table and you put a chip on every number.

Paul: Sure. Why not?

Rich: You just have to. You actually, it’s not even a why not? It’s you have to. You have to be present in this space and that space —

Paul: Well especially in lack of a — when you don’t have specific, like, Apple had that specific product strategy around like three product lines.

Rich: Yeah. Right.

Paul: And then that everything that wasn’t in there just kind of got thrown out of the company brutally.

Rich: Right. Actually Apple, I think, is kind of distinct from a company like Microsoft, where you tell them, “Look, search is taking over the world,” and you say, “Well how much is it going to cost?” And it turns out it’s only a dollar out of the thousand dollars that you have. And you’re like, “Well, go do it.” And then they have to mobilize a team of 2,000 out of 50,000 —

Paul: Right.

Rich: And they just go do it. That doesn’t mean they’re going to do it well. I think when a company is, its DNA leads right back to the core thing that made it what it was, like a Google is defined by search —

Paul: Right.

Rich: It defines it. When you say Google, you mean search. So when you tell Google to go make a car, you have to wall that off and do it over there, and —

Paul: And not even search. You’d almost say, like, accessing information, right?

Rich: Right. Exactly.

Paul: Microsoft is about corporate productivity.

Rich: Exactly.

Paul: Apple has been about experience from day zero down to the wire.

Gina: Yeah.

Rich: Exactly. OK so let’s go back. So you became a writer. Did you stop programming?

Gina: Uh…

Rich: I mean, Lifehacker explodes, you’re in the middle of it.

Gina: Lifehacker explodes. I was the solo, the sole blogger there for a while, like the first nine months, and yeah, I stopped doing anything except writing posts, it was like twelve posts a day. It was an incredibly fast pace.

Paul: Right. That was — it was bulk. I mean, that’s the thing.

Gina: It was. And I’m a perfectionist, so like every typo would just kill me a little bit inside, so I would go back and fix it, and —

Rich: So you stay on this as a writer.

Gina: Mmmm hmmm.

Rich: See my recollection of Lifehacker, I just imagined, I wasn’t visiting it every day. I would get links. And I imagined it was ten writers.

Gina: Yeah, I mean, at some point it probably was. I think at our largest we were like, seven people. So it was —

Rich: OK.

Gina: You mean like four —

Rich: So you started out —

Gina:; — or five bloggers, a couple of copy editors, some community people once we got comments, community moderators became very necessary, so we grew pretty fast. At the end of the first nine months, I was like, “I need help.”

Rich: So wait. You jumped on this — because at any point you could have said, “This is great. Congratulations. I’m a coder.”

Gina: Yeah.

Rich: “Like, this is really great. I’ll help you get this on it’s feet, but — ”

Paul: Well wait a minute —

Rich: “ — I need to go back to my craft.”

Paul: There actually wasn’t a ton of great work for programmers, like, floating around at that exact moment.

Rich: Mmmm.

Paul: And this was interesting. Like, I mean —

Gina: Yeah.

Paul: — it wasn’t like somebody was sitting there like they are now with a huge sheaf of cash, going, “Hey programmers!”

Rich: Also, you loved it. I mean, this was — you didn’t do someone a favor here.

Gina: No.

Rich: This was something that was your own.

Gina: I loved it, and Gawker had set up this, you know, they’d really sort of gamified the whole thing for you, because I became, or like, addicted to the attention.

Paul: Oh, that dopamine rush.

Gina: I had the site meter chart embedded at as a widget on my Windows desktop so I could see the traffic build through the day, and we got paid, like, at one point, there were many different pay structures, at one point we got paid based on page views, and you know, Digg, like, “We got on the front page of Digg!” And there would be this huge spike in traffic! And I derived a great deal of satisfaction from the idea of, like, thousands of people looking at my stuff every day. It was totally this, like, ego thing.

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.

Paul: Isn’t that amazing? Yeah.

Gina: Which is pretty amazing, because then when I actually did publish my book, I was like, “I didn’t hear from anyone about this.”

Paul: No. No one ever —

Gina: 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, you know, the pace of the work and hearing from so many people every day was great, and I didn’t sleep a lot. But I loved it.

Paul: So it’s just you. Twelve posts a day.

Gina: Yeah, at first. Mmmm hmmm.

Paul: How many years did you do that?

Gina: So that was like the first nine months, and then we started hiring people.

Paul: OK.

Gina: I hired a team, over time —

Paul: Even there, like, having a team on a blog was a big deal.

Gina: Yeah, yeah.

Paul: Because blogs were supposed to be one person.

Gina: Right, well BoingBoing was a group blog.

Paul: That’s right.

Gina: And MetaFilter always called itself a community blog, I never —

Paul: Yeah.

Gina: I always saw it more as a forum. But right, group blogs were uncommon. But you know, at this point Gawker’s rolling out their whole stable, right? Like they’ve got, like, Gawker and Gizmodo an then Lifehacker and, you know, iO9 and Deadspin. Lifehacker launched on the same day as the travel site, which didn’t make it.

Paul: Gridskipper.

Gina: Gridskipper! Yes. Me and Andrew…Krucoff? That’s right. Andrew, I’m going to apologize if I mispronounced that.

Paul: Hi Andrew! How are you doing?

Gina: Yeah, so they were growing out their stable and there was lots of cross-posting and all that stuff.

Rich: OK, so there’s a point in time when you decide, well, I don’t know how it goes, they could have said, “Oh my God, I can’t believe you posted that, Gina. We need to let you go.” [laughter]

Gina: That’s not what happened.

Rich: OR it could have been, “All right, I think I’ve done my gig here, it’s time to move on, etc.” So how does Lifehacker end for you? Lifehacker’s still around. That’s worth noting.

Gina: It’s still around. Doing great, yeah.

Rich: Very successful.

Gina: It was just this, like, very fertile time where people were building, like, little apps and releasing little apps and stuff was coming out —

Rich: What year is this? Sorry to interrupt, but.

Gina: Well, Lifehacker started in 2005, so like, before the iPhone, before Firefox, before apps. And things like Delicious were getting launched by, like, you know, regular programmer types that were like, “I’m going to throw something up on the web.”

Paul: Joshua Schachter.

Gina: Joshua Schachter. And then —

Rich: Exciting time.

Gina: Very exciting time. And then APIs started to become — 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 fifteen ideas that I’d like to build.

So yeah, so 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. And this was in 2009, and I was a feature — I was like a weekly feature writer there for a while. Adam Pash, who was my senior writer, took over, and he did great, and so, yeah, it was all good.

Rich: Very smooth.

Gina: But yeah, I decided that it was time. I had had my taste of, you know, million-pageview posts, and I was, like, ready to now build something. That’s not a web page. And not worry about page views every day as a measure of my success.

Paul: You really did represent significant traffic at a moment when there wasn’t a ton of significant traffic. Million-pageview posts are now just, sort of like a normal Buzzfeed day, for like something mildly viral.

Gina: Yeah.

Paul: But that was colossal.

Gina: Yeah.

Paul: And weird! It was weird that it was about nerd stuff. That’s what I remember, just sort of being like, oh wow, what’s happening in this world? Is this actually pop culture now?

Gina: I mean, like, an article like “How to Jailbreak your iPhone” would just do, and we were great with SEO, because that’s exactly what people type into the Google search box —

Paul: And they became evergreens. Like —

Gina: Yes.

Paul: — they would just hang out.

Gina: Mmmm hmmm.

Rich: But you also did stuff like how to get that stain out of your shirt, right?

Gina: Yeah, I mean, you know, we would do these household tips.

Rich: Yeah.

Gina: Somebody made a joke recently that, she was telling her mom about Soylent, and the mom was like, “Isn’t that just SlimFast?” And the woman was like, “Well, but it’s made by men for men, so it’s technology, and it’s called Soylent.” [laughter] Well Lifehacks was like, here are like, the household tips that you would have found in women’s magazines for decades, right?

Paul: Right.

Gina: But it’s called Lifehacks, and it’s for guys, so this is new and innovative technology.

Paul: Oh my God.

Gina: So ‘how to fold a shirt’ and ‘how to get the red wine stain out of your shirt’ or ‘how to open a beer bottle with a piece of paper,’ these were really exciting, big, popular posts.

Paul: So you went off to make things.

Gina: I did.

Paul: And what have you — do you want to talk about the things you made? Do you want to talk about the things you learned? What did you learn about making things. [laughter]

Rich: Let me ask about that first, I mean, you’ve been away for a bit.

Gina: Mmmm hmmm.

Rich: See I —

Gina: Yes.

Rich: — I’ve been more or less either driving product groups or running businesses and telling myself I’m going to come back to coding —

Paul: Since you were eleven years old.

Rich: Forever. And if I go back now, I’m going to feel…there’s this sense of being a novice, coming back into the world.

Paul: Nobody wants you programming.

Rich: Nobody wants me doing a lot of things, but yes, but the thing is, it’s, you know, that satisfaction of building.

Gina: Yeah.

Rich: Is unique, right? And somehow that experience was, I mean, coming, deciding all right, you know what, I’m going to roll up my sleeves, we’re going to do this.

Gina: Well I had, during Lifehacker’s, the course of doing Lifehacker, I had managed to squeeze a budget, a programming budget, out of Denton, to be like, hey, there are little bookmarklets and maybe Firefox extensions, maybe a Bash script here and there that we could release right here on Lifehacker —

Rich: Funny.

Gina: — that would be, you know, an exclusive download, and he was like, “All right.” So Adam Pash and I both, like, I was building little one-off things —

Rich: OK.

Gina: Like a bookmarklet, or a Firefox —

Rich: OK, so you were exercising a bit.

Gina: I was exercising my muscles a bit. I released a script called Todo.txt, which is a product I still maintain, and that the community contributed to. So I had kept the wheels kind of greased. But listen, I’ll tell you, my first week, I was enchanted with Twitter at the time, the Twitter API was getting a lot of, you know, I was hearing a lot about that, and went out and bought the O’Reilly book, like, the getting started with the Twitter API, you know? And I copied and pasted code, which was in PHP, and used the XML version —

Paul: Mmmm hmmm.

Gina: — of the, which was a sad choice.

Paul: Gina: made eye contact with me when she said “XML.”

Rich: Yes.

Gina: I did, I did.

Paul: [XML-related sigh]

Rich: I just looked down. I didn’t want to be involved.

Paul: No.

Gina: And I started from there, right? Like I copy and pasted a bunch of code, and then I started messing with it, right? This is — real programmers do this, like I feel like people are like, “I’m not a real programmer, that’s how I work.” That’s how real programmers work too, so.

Rich: Yeah. They just go.

Paul: I mean the concept of “real” is disaster in all of our lives.

Gina: Yeah no, but I did, I got really rusty, like during that time, like, JavaScript became the language. And I missed that. Like I was stuck in the Python, PHP time, and then I was like, writing Lifehacker, and then suddenly I came out of Lifehacker and was like, “Oh, everyone’s writing JavaScript everywhere? This is the thing?”

Paul: Well the reality is when that happened, everyone who had been around for a while was like, “Really?! JavaScript!??!?!”

Gina: Yeah!

Paul: Because it was, it was so bad for so long.

Gina: Yeah.

Paul: And so difficult to work with, and you had to know a little bit, and it just broke in every possible way.

Gina: window.open.

Paul: Yeah.

Gina: That was the extent of my, yeah, like how do I pop this window without any Chrome. OK.

Paul: And it was just a bad, ugly situation —

Rich: There was inconsistency, it was just…

Paul: Oh yeah.

Gina: Yeah.

Rich: Browsers all line up now, but there was a day where it was, you’d have to have all kinds of separate logic for different browsers. Ugh. It was unbelievable.

Paul: It actually just goes to show the, like, people want what they want. They wanted the web browser. JavaScript came with it. And then, I mean, how many billions of dollars now have gone into making JavaScript better?

Gina: Yeah.

Paul: And how many millions and millions of person hours? So…

Gina: Yeah. I mean, if you include the frameworks —

Paul: Madness.

Gina: Yeah.

Paul: It’s madness. I dive in there every now and then and I’m just like, whoa.

Gina: It’s like, what happened.

Paul: That’s a big surface.

Gina: Yeah.

Paul: OK, so you’re out there, back in the world. You got Todo.txt, which is an Android app?

Gina: There’s an Android app, an iOS app, and a command-line app.

Paul: OK.

Gina: And actually a bunch of community web-based versions, and desktop-based versions. It’s an open-source app, so a bunch of community members have made Sublime Text plug-ins. It’s really spawned —

Paul: And I can go download that now on my phone?

Gina: Yeah, yeah. Todo.txt, mmm hmmm.

Paul: Still has a community going?

Gina: Yeah, yeah. I admit I’ve been a little bit absent. So some folks have taken over, but just because it does everything I needed it to do.

Paul: This is worth talking about: what happens, because I have this, I started this thing accidentally one night called Tilde Club.

Gina: Yes!

Paul: I just booted up a Unix server and told people they could have accounts, and there’s like 1,000 accounts on that.

Gina: That was crazy, Paul!

Paul: It was really fun, and people made web pages, and it was old-school, and it was cool, and it’s still kind of out there, running, and I can’t, like, what happens when you lose interest in your own product?

Gina: You know, when I see people come into the Todo.txt mailing list, like, “This is the coolest idea ever!” I’m like, “Yeah, you are mentally where I was ten years ago.” It’s ten years old —

Paul: Right.

Gina: This June. And I appreciate that, but I do not, just, I just don’t have that enthusiasm about it anymore, you know?

Paul: OK.

Gina: Because I’ve seen it through, and it’s tricky, I’m still trying to figure out, like the iOS app has really, sort of fallen into disrepair, and now it’s just, like, kind of embarrassing, like, I have this app out there that I’m clearly not maintaining, so. I think it’s a graceful thing where you just have to kind of hand it off to a community member who has the energy.

Paul: The tricky part is that if your situation is like mine, there’s no single point of communication where you can go, “Hey everybody, I just thought I’d check in. This person’s gonna be deputized.” There’s no process for that. You can’t just, like, run out and be, “I better let the iOS people know and the Android people know” and so on.

Gina: Right.

Paul: These projects and these ideas get spread all out, and to get the clarity that you need, you can’t simply issue a press release.

Gina: Yeah, that’s true.

Paul: And nobody undertakes to start a project and leaves channels whereby they can resign.

Gina: Right.

Rich: Well also I think you consciously want to move on, like, it was fun, but the high of —

Gina: The highs, yeah.

Rich: — launching it and it working, it goes away pretty fast. I mean, obviously you could have an insane roadmap of something very ambitious, but very often, you’re kind of done. There are features you want to add to it, but you’re already thinking about the next thing you want to do.

Paul: You just, you can’t muster the enthusiasm.

Rich: You can’t.

Paul: And there’s no external carrot, there’s no…

Rich: I mean that’s part of the genius of GitHub is it isn’t just organized storage, so to speak, but it’s also a communications means that allows it to be, you know, managed, because there’s consistency in how things are put away. Versus like, oh it’s just over here, in box.com, or whatever. Box.net.

Gina: And you can fork it, and do a thing…

Rich: Exactly.

Gina: What you want to do with it, yeah.

Rich: Exactly. There’s a set of actions that are consistent across projects.

Paul: So you built a few fairly big things?

Gina: A couple.

Paul: What were those?

Gina: Lots of little things, and a couple of big things. Well, when I bought that O’Reilly book, I started writing a PHP script which eventually turned into an app called ThinkUp, which I then, my co-founder Anil Dash and I turned into software as a service, because it was this web app that you’d install on your web host, similar to WordPress.org. As it turns out, not a lot of people have web hosts these days, and, you know, you’d have to get a bunch of API keys to run it. So we launched it as a service, software as a service, under our company, called ThinkUp as well, and that’s been a subscription service for a couple of years now. We did —

Paul: I’m a subscriber.

Gina: And you —

Paul: I like it!

Gina: — you are a subscriber, yes. You are. You’ve been a big supporter.

Paul: So yeah, ThinkUp is good.

Gina: Mmmm hmmm. And then we built this site called Makerbase recently. This was one of Anil’s ideas. It’s like an IMDB for apps or websites, it’s a user-editable director of projects and people. And in many ways it’s like an homage to this time where people would just hack on a little thing on the weekends — it’s meant to, unlike something like CrunchBase, it’s mean to encompass art projects and side projects and just kind of little, you know, Paul and I spent the weekend together hacking together a Chrome extension, and like, here it is.

Rich: It’s the movie model. You don’t have to start a company —

Gina: Right.

Rich: — and do all the housekeeping around…

Gina: Right. There’s actually no companies in Makerbase.

Rich: Four people can get together and do a thing.

Gina: And just do a thing. Yeah, it’s about collaborations.

Paul: And now —

Rich: — you are here.

Gina: Now I’m at Postlight.

Paul: How did you prepare yourself to go back to full-time work. And this is not to say you haven’t been working — you’ve probably been working way, way more than full time.

Rich: Gina: works hard.

Paul: No, but I mean, when you’re working for yourself —

Gina: Yeah, you’re just basically working all the time.

Paul: It’s kind of always working. So now you’re, we’re not quite 9–5 but we’re actually very close.

Gina: Mmmm hmmm.

Paul: How did you prepare yourself?

Gina: Well it’s actually very fortuitous that my start date was right around tax time, because I was reminded about how annoying it is to do your taxes when you are, like, have a company and a bunch of freelance gigs — like I’m so excited about the idea of —

Paul: It’s the worst, yeah.

Gina: — like, a uniform paycheck on a regular schedule, with all, that’s going to be amazing.

Paul: I’m glad.

Rich: Give us a minute though, Gina. [laughter]

Paul: No, but I’m also —

Gina: That is part of the deal, that was part of the deal, right?

Rich: [laughing] Yes.

Gina: The regular…

Paul: That’s definitely a reason to take a job, for everyone who’s out there, like, just one piece of paper at tax time. That’s our recruiting strategy for engineering. [laughter]

Gina: On a very practical level, there’s that, but on a bigger philosophical level, is, you know, I’ve been running a two-person company now for two years, and I definitely have a little bit of lone wolf in me. Like 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. It’s slow. You just, 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. And I did get to the place where I was like, I want to learn, I want to work with other developers and learn. Like, I was kind of the person that was like, this is how we’re going to do it. But I wonder how other people are doing it. You know, like, when Mark and I collaborated on Kinja, that was, that was an amazing collaboration for me, where I grew so much.

Paul: I’ll admit to a moment of true pride, because Gina was in our chat software Flowdock and just asked, “I’ve heard there’s some people here in this chat that can help me get up to speed on Node.js, which is a JavaScript server-side programming environment. And I just read the thread, there were, you know, a bunch of people just jumped right in and they were like, “Here’s the stuff. Let me get you some links.”

Gina: That was amazing.

Paul: “Andy over here is also learning.” And just for me, like, that was, I was really hopeful we’d hit that kind of culture.

Rich: Yeah.

Paul: And I think that you’ve built environments like this in the past, but it’s the first time where I’m like, this is a company that can figure stuff out as it goes.

Rich: Yeah.

Paul: And it also requires a lot of vulnerability. You just showed up and you’re a pretty serious senior engineer in our organization.

Gina: I thought about that.

Paul: Yeah.

Gina: I felt pretty vulnerable. And I didn’t, no one, everyone was like, “OK, here’s, you know, this is where you should start.” There was not judgement, there was lots of helping, like right away. It was great.

Paul: That’s good. You’ve got to be able to come in and learn the new stuff. Because it’s such an enormous, ridiculous industry.

Gina: It is. I have, I really have accepted that, I used to feel worried, like I can’t call myself a real programmer because I don’t know all the new things. I’m never going to know all the new things. And that’s OK.

Rich: You’ve got to embrace that. I mean, you have to be OK…

Gina: Knowing what you don’t know, yeah, just knowing what you don’t know is cool. I was totally fine with being like, you know what, I don’t have any experience with Node. And let me tell you something: Node’s pretty cool. I just spent the last day or so working with Node, and I feel, you know, like I know what’s going on.

Paul: Ah, there’s 36,000 amazing frameworks that you’re going to get to learn.

Gina: Yes. [laughter]

Paul: Well anyway, we hope you’re happy.

Rich: We will do a happy check-in in podcast #28.

Paul: Yeah, exactly. [laughter]

Rich: Should we end every podcast with, “Is Gina happy?” [laughter]

Paul: Uh…that’ll go — other employees will love that.

Gina: Yeah. Yeah.

Paul: That’ll be really…

Gina: Yeah, let’s cycle through the teams. It’s a team effort.

Rich: You know what we should do?

Paul: Do you already feel like there’s a little bit of a target, you know? Because you’re the new person, you’ve got your shoulders hunched a little bit? Hi, hi! [laughter] Well, Gina, you’re here, you better get back to work. [laughter]

Gina: I’ll do that.

Rich: We should probably get back to work. [laughter]

Paul: We should get back — everybody needs to get back to work promptly.

Rich: Yes.

Gina: Awesome.

Rich: But thank you for doing this today.

Gina: Thanks for having me!

Rich: Awesome.

Paul: It’s great, you went from guest to employee, that’s never happened before.

Rich: Yeah.

Gina: I know, that was a pretty good trajectory.

Rich: All future guests of this podcast —

Gina: Will eventually become employees?

Rich: Will eventually become employees.

Gina: Do you need to hire them before they appear?

Paul: Ah, you know…

Rich: We haven’t thought it through, frankly.

Paul: This is a marketing vehicle. We can throw certain ethics to the sidelines.

Rich: Yeah.

Paul: Just kidding!

Rich: I think we’re — you know, this is good enough stuff that we need to stop apologizing for it being a marketing vehicle. I think it’s the real deal.

Paul: I like to just remind people that we’re a company that they should give money to [laughter] rather than their podcast entertainment.

Rich: Fair enough, fair enough.

Paul: Gina: thank you so much for coming on our show.

Rich: Thanks, Gina.

Gina: Thanks a lot.

Paul: And onto our team. We’ll check up on you in GitHub later.

Gina: Cool. See you then. [laughter]

Paul: Thank you.

Rich: Thanks.

Paul: Well, Rich:, that was cool.

Rich: That was great.

Paul: Yeah.

Rich: Enjoyed it. Again, I have a fear that we sound like oldies radio, so I’m just going to say the word SpaceX.

Paul: SpaceX is real good. Uhhhh…what else are kids really into? Buzzfeed.

Rich: Are kids into Buzzfeed?

Paul: Uhhhh…..YouTube stars.

Rich: Minecraft Mods.

Paul: Flash games. Thanks for joining us!

Rich: Buh-bye.

Paul: That’s the worst outro ever. [laughter]