Chris Castiglione Co-founder of Adjunct Prof at Columbia University Business School.

How I Learned to Code with Nathan Baschez

35 min read

Nathan Baschez (Product Hunt, Gimlet Media) is one of the most prolific creators I know, having worked at half a dozen of the coolest startups I can think of, all in just the past ten years.

I first met Nathan back in 2012 while we were working at General Assembly in New York City. At the time General Assembly had just acquired Nathan’s startup Dash — an early learn to code app much like Codecademy.

Since then Nathan has gone on to co-create Product Hunt, launch HardBound (a visual storytelling app), as well as dedicate his talents to Gimlet Media and Substack.

In my chat with Nathan we discuss: 

  • How to design a career
  • Strategies for choosing projects
  • Behind the scenes of early days at General Assembly, Product Hunt, and Gimlet Media
  • Lessons learned from building Hardbound
  • Tips for staying focused when learning to code for the first time

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Nathan, how did you learn to code?

Nathan: That is a good question. So I was in college. I went to school at Michigan State University, and when I went to school, it was originally going in thinking I would do something like be a Philosophy professor, or maybe a lawyer or something, like constitutional law.

Something cool like that. I had no clue what that meant. But when I learned a little bit more about what it entailed, I realized it would be challenging because law school requires a lot of difficult and somewhat boring stuff, and I have a low tolerance for the somewhat boring stuff. And being a professor is a very hard gig. Especially in the humanities, it’s just like really, really hard.

So I somehow stumbled upon Paul Graham’s essays about starting companies and being a programmer. And I was like, this is really cool because you get to create your own thing. That’s extremely not boring. Maybe people want to use it and you can make money doing it, so if it works, obviously better, hopefully than being a professor which is like really hard.

You have to really want to do it and love your subject-matter.

I just knew I didn’t have it for philosophy. I just thought it would be kind of a cool thing to do, I guess. And so I instantly said “this is it”! I want to build companies and I want to build them on the Internet using software. But the problem was, I obviously did not know how to do that at all.

At first, I would describe myself as more of like an ideas guy and I quickly learned that that was very hard to do because you’re essentially coming up with concepts of things that you have no clue if they’ll work or not, and you have very little, if not zero ability to make them happen.

So I pretty quickly learned I need to have something I can kind of contribute if I’m going to find teammates, and it’s even better if I can create some momentum on my own and then show people that it’s kind of working and see if that works.

And so basically from there, it was a pretty quick path to buying a book called Head First HTML, CSS, and then I also got Head First PHP and MySQL. And I just kind of went through those books and learned a lot of stuff on the Internet.

I remember, I think at the time Treehouse was brand new. It wasn’t even called Treehouse then. It used to be called something else. You remember this? I don’t remember what it was called.

Chris: I used to use it back in the day. I know what you mean. It did have a different name. [Think Vitamin]

Nathan: Yeah. It was before they changed it and before it was particularly big. It was just like some blog I think started like a video series.

Chris: It was Ryan Carson. Yeah. It was Carsonified. It was this thing. I don’t know. It was like a side project. Yeah, I know.

Nathan: Yeah. Exactly. And so I don’t know, it was like the when that first started. This was like 2010, 11, something in there.

What was the first website or app you ever built?

Nathan: It was at a startup weekend. These were huge at the time. My friend, Eric Jorgenson organized it at Michigan State and I competed in it and met some people there who could write code better than I could and I was kind of like plodding along doing my best. And we built a thing that was pretty cool.

It was basically like if you have a thought or you want to save something that’s not like a to-do or reminder or writing down someone’s phone number or something that you’re supposed to remember, but like something more like creative or something that’s just like the kind of thing you want to keep more of in your life and to remember. You basically pull out this app, you write down whatever the thought is or the quote or whatever, and then we show you a random one from the past as a kind of like a reward.

So it was a cool little weird loop of programming your brain with different stuff and saving stuff and seeing stuff in a way that was kind of novel and interesting. We built that and then I was just kind of off to the races – I like building things. People actually used it. I realized that I could write code and people would do something with it and it’s fun. Yeah.

So that was the first app?

Nathan: Pretty much. I mean, I remember I did some HTML and CSS for MySpace before that, but if you want to say like an app, definitely that was the first iOS app and honestly, even the iOS app, I didn’t have anything to do with.

I helped with the front-end of the website, basically, so I had the least programmery type job of the whole thing. But yeah, I think that was the first – call it first product type thing that I built. I had definitely sort of brainstormed stuff before that and done some HTML, CSS fake interfaces of things but I had never had a thing with a database that really worked before that.

So you said you learned to code using the Head First series? What other resources were you using?

Nathan: The Head First series from O’Reilly is amazing. Where it’s like a very beginner-friendly I would say series of books and I don’t even know if they’re still up-to-date or whatever. If they have Head First Node or Rails or something, but Head First PHP and MySQL were awesome in terms of just understanding the very basics of – you have files on your computer, you run a version of a server on your computer, then you go to in your browser and you can load the file and then submit stuff to a server and the server can do something with it.

Put something in a database. Get something out of a database. Return a new HTML file that’s like dynamically generated. That kind of really basic stuff, I just, I had no clue about what HTTP requests were? Like that kind of stuff.

Then once I got a little bit more oriented, I started branching off on the side and trying to build my own things using the stuff I had learned so far from this book. When I would get stuck, I would either look in the book or Google something to see if I could figure it out. I also did a little bit of the video series.

Videos never for whatever reason worked as well for me. I always preferred to have something that was a little bit more self-paced and also I like to listen to music when I was doing stuff. I remember having that book and just feeling like so cool. There were these people in Ann Arbor that I had met at the Ann Arbor New Tech Meetup, is like the startup meetup of Ann Arbor, Michigan.

I would drive down there and I got to know some of those people and they were all like really good programmers, like computer science type people, I didn’t have a lot of exposure to people like that.

And I just remember this feeling of how cool it was to be able to write code and stuff and the O’Reilly book was a part of it for me because I noticed that those are the things that real programmers did, and of course they had the Unix guide or whatever. Something pretty different in the Head First series. But like whatever. It was awesome.

Chris: Yeah. Those Head First books are awesome. I’ve used them as well because they have lots of illustrations and just more fun examples.

Did you say you tried to learn to code using videos?

Chris: I want to focus in on how you said that videos didn’t necessarily work for you and I find that in myself as well, because for me, I actually have a really hard time sitting in class and videos are okay but I tend to really like books as well but I know because I teach this, I know a lot of people in my class feel the exact opposite way.

So I think when you’re starting to learn to code, it’s interesting because I guess you kind of have to find the right medium that works for you, whether it’s in the classroom, whether it’s on your own time, or schedule time. I think everybody has a different way of learning.

Nathan: Yeah. Definitely, for me it was like very motivating to have specific ideas that I wanted to build and I could kind of get over this initial hump of getting oriented or whatever with the tutorial book type approach, where you’re building something that they want you to build rather than do your thing.

But as soon as I’m like, okay I can see basically from what they taught me, how to build this thing, I can take what I learned and use it to build this other thing, and then any gaps in my knowledge I can just Google, that’s the best feeling ever.

When you’re building a thing and you basically know that you’re at the point where you know how to Google stuff and you can build the thing and you’ll get some specific answer to a specific question. That’s really helpful. So just Googling for specific questions or problems and reading tutorial books were probably half of how I learned.

The other half was just like really smart programmers that I was either friends with or worked for, basically. And so after college, I got a job at a startup called Olark, moved out to Palo Alto and that was the first time I really was like full time, to some degree, writing code.

I was more of a designer there, but I was on the code base and working with engineers, and they were very patient with me and very helpful in terms of like kind of my learning process, I guess.

It’s even better if you have a specific thing that you are running up against and you Google it and your Googling is too much of a high-level thing for Google to really know what to do with it. Much better when you have a person that can say, “Ah, you’re asking for this. But that’s not actually what you want. You have a mistaken idea that this thing is the same as this. But actually, it’s a totally different thing that you need to understand and you should Google about database indexes or whatever because that’s the reason why your query is slow”, or whatever specific thing you’re running into.

So you learn better with when a real person can guide you? Better than with videos alone?

Nathan: Totally. Yeah, exactly.

What was your major in college? How did you get from college to building Dash?

Nathan: I graduated with a degree in political theory, basically political philosophy and it was a lot of fun but not very directly applicable I would say to building software. Although, the more that time goes on, the more it does feel like it’s maybe applicable because it’s about what is the good life, how should we structure society and technology has a lot to do with that.

So I think it’s good to be thoughtful about that. But anyway, I digress. So I got the job at Olark basically because I was very enthusiastic and it was unclear exactly what I would do, but I was a good enough designer based on some stuff I had previously designed for my own projects that I was building that they were like, “Okay. We can hire him as a designer. He’s not like the best designer but he’s probably a good enough designer and we can sort of figure out the rest from here.”

It was like an internship basically, so I wasn’t getting paid very much at all or anything, it was a great sort of just like, “hey we’ll give you a chance” kind of experience.

How did you get your first job out of college? (Working at Olark)?

Chris: Did you apply via their site or via job board? How did you get connected?

Nathan: Oh, so when I was in college I started a meet up called Hackers and Hustlers, which had good meetups for people interested in technology in Ann Arbor but not in East Lansing, Michigan State and so basically one of the first speakers we got, I don’t remember who but someone that was like more kind of experienced in the tech world of Michigan introduced me to this guy, Zach Steindler, he’s one of the co-founders of Olark and lived in Ann Arbor. They were a remote company before it was cool to be remote, really.

This was before Slack and everything else. Basically, Zach spoke at this meetup and then after the meetup, he’s like, “Hey, what are you doing after graduation?” And I was like, “Oh, I don’t know.” I think at the time I was like, “Oh, I’m starting this company or whatever which was like a bad idea and it was totally destined to fail. But I ended up never starting it though because he was like, “Well, you could maybe come intern for Olark.”

And so I did that and moved out to Palo Alto and it was an amazing decision to do that. But anyway, so then when I was at Olark, I was there for like a year and a half, almost two years, and I just kind of realized I really wanted to work on something that was more consumer-facing.

So they built a tool for websites to put in a chat box in the corner where you can ask someone live why does this thing cost more or whatever. Anyway, that was nice. It was cool to build something that makes it easier for people using websites to figure out answers to their questions and to help people who run these websites get more sales in a lot of cases, or helping customer support.

But, I just really wanted to work on something in like people using the Internet to make themselves smarter. I always loved books and reading articles and stuff like that. To me, the promise of the Internet is like, at its core, related to that. I mean there are lots of really nice things that make the world more efficient or whatever, but I was kind of thinking of the computer as this supercharged amazing book, that’s like you can learn anything and form relationships or whatever. Debate ideas.

And it all can be in formats that have nothing to do with paper but a lot of the content we consume is so much like digital copies of the paper, basically, or digital copies of TV basically. Or digital copies of radio but computers are obviously totally different things though. So, I was like “what can I create that would use the computer in a better way?” And so basically as a side project, I started working on this thing to teach people how to code where it’s like, I was thinking of the Head First books and I was like, but what if, instead of a book, it was like interactive and on a web page and you could write the code and it would tell you if you did a good job or not, you know?

And so I actually left Olark basically in an ill-fated startup attempt to do this and I was thinking of like maybe I would do some sort of discussion forum thing or whatever. I wasn’t sure what it would be but that’s kind of how I ended up working on Dash which is this project to teach people how to code.

Why use Dash to code?

Chris: I first saw Dash in 2012, right when it came out. I was working at General Assembly and I remember the day we met! We were in the kitchen and Brad Hargreaves introduced us. I remember he showed it to me and I had never seen anything like that before where you could code in HTML in the browser and then see the images appear in real time.

I think it was kind of this instant gratification feedback loop for people who are learning to code. Especially because when you’re learning to code, often installing the software can be this kind of barrier to entry. People, maybe they don’t have access to their computer, their work computer, they can’t install it or they trip something up. And so you didn’t have to do anything.

I mean I guess it’s kind of like how Codecademy is and was around the time, but there was something more visual and project-based about Dash that people got excited about.

Nathan: Yeah. Codecademy was an array – a list of things. Here, create a new function, you put in an input and you’ll return an output. And it was like the command line, basically what it was based off of.

That’s not to say it’s bad, I think it kind of starts in the wrong place for most people because I think a lot of people want something that they can understand quickly and if I’m here’s how to make a webpage, you’re used to looking at web pages, now it’s like, make one using the actual code that it takes to make one.

HTML and CSS are like just a lot simpler and more visual to understand. And then as you start getting a little bit better at that, we sprinkle in JavaScript, where you can make pretty advanced stuff with games and things.

Or we made a CSS robot to really get into how these things work. So I think you can get advanced pretty fast but it has to start from this point of like, I feel like I’m looking at something that I’ve seen before on the Internet, and if you start with, here’s a function, here’s what it does, it feels like you’re giving me a bunch of sort of dictionary definitions that aren’t super motivating.

Like it feels like you’re getting somewhere. The phrase that I always put it was like, where’s the sort of light at the end of the tunnel? If you’re telling people things and they’re kind of saying so what, then it’s not emotionally connecting. Whereas, if you’re telling people things and they are like “whoa!” then they feel like they’re getting closer to what they want, so that was what we optimized for.

Nathans vision of as a “visual book”

Chris: That’s really cool. And I mean I guess that’s part of the vision that you have of the web as being this kind of visual book that you were saying where there’s like you can communicate and invoke emotion through the products that you’re creating.

Nathan: Yeah. Also, I felt like it would kind of help to have some really low-level narrative to put you through it. So we put you as if you’re building something for a friend. Like a friend wants you to make this thing for them and so would you do it? And we’ll help you do it or whatever.

So we didn’t want to be overly gamified or story driven or whatever, but there was like a little bit of that in it and I think it helps to kind of put some conceptual wrap around it. But it’s funny because I actually was able to get in touch with Kathy Sierra (Head First author) and she gave me a lot of amazing advice and she’s the one who made the Head First series that I actually used to learn how to code, those books.

So it was a pretty cool thing to get the chance to email back and forth with her. I think we got on the phone once or twice.

But I don’t want to overstate how involved she was, it was pretty cool to kind of take it full circle of I learned using things that she made and now I’m teaching other people using ideas from her experience.

Was this meeting with Kathy Sierra (Head First author) back in the day? Or was this kind of more recently?

Nathan: No that was back in like 2012, when I was building Dash.

Chris: Oh, when you were building Dash. Yeah. For sure.That’s amazing. One of the things that I really wanted to talk to you about today is you’ve worked on so many different projects. I forgot that you had worked at Olark as well.

Nathan: Yeah.

Nathan, how do you choose what you will work on next?

Chris: Olark, Dash, General Assembly, Product Hunt, Gimlet, the list goes on and on. How do you choose what you’re going to work on?

Nathan: That’s a really good question. It’s some combo. So there are lots of things that I may want to work on, but that I’m too focused on something else. So like, for the past year, I’ve been 100% Substack ever since I joined and I really haven’t had time for pretty much anything else, including, even like writing or something like that. Like a one-off blog post or something.

I try to do that to dog food our own product because Substack basically helps writers create paid email newsletters. Also you can use it without charging, so it just works like TinyLetter basically but more modern and full featured.

It’s funny. I’ve been totally focused on substack. So part of the filter is just like okay, when do I have time? And then okay so if I have time, and I’m looking for something new because I either like left a job or I’m thinking about leaving a job and I’m creating space to figure out what’s next or like same thing when I was at Hardbound, that was the company I founded after I worked at General Assembly.

It’s like I was just focused on that the whole time. But at a certain point, we ran out of cash and that did not work out, so I had to figure out kind of what was next. So there are very limited windows where it’s like, “I’m like a taxi and my light’s on,” you know?

So first of all, my light has to be on. And then when my light is on, how do I decide what to work on next? I mean, first it is sort of the practical – financially, what do I need right now? Right? Because I’m in a spot where I feel comfortable taking more risk and owning more of it but getting compensated less up front? So starting a company or maybe trying to stay kind of independent, building some freelancey type thing where the money is a little bit more risky or do I need to earn some money and I’m just looking for a full-time job?

So after hardbound, I was like completely broke and emotionally pretty tired because I had been running this thing for a couple years and it didn’t end up working out. And so, I was definitely like, I need to get a full-time job because I don’t want to manage multiple freelance type clients. And I need to start recouping some of the money that I lost while I was working on hardbound.

Now, I just recently left substack and I had had a pretty good job for about a couple years. I’m the kind of person that always wants my fingerprint to really be on what I create and to be able to create things that are valuable and I want to have a lot of autonomy and ownership over it. So I’m open to different things right now, but I’m a little bit more willing to take more financial risk to build something that I have more ownership over.

So that’s sort of the core criteria. The other thing is, I’ve tended to gravitate towards things that aspire to make people smarter. So, you know whether it’s education or media, it’s like somewhere in-between those two but once I kind of figured that out, from my experience at Olark I built Dash, which helps people learn how to code.

Product Hunt, which I ended up not joining full-time. It was just kind of like a side project with Ryan but the thing that I loved about it is, it helps people kind of figure out what’s out there and take inspiration from other cool things that other people are making and talk about what is interesting about it or what could be improved about it, et cetera.

What is Hardbound? Why did you create it?

Nathan: After Product Hunt [I created] Hardbound, which is basically like Dash except instead of just learning how to code, it was visual. Dash has a visual slideshow format to teach you how to code in addition to the like you can just write stuff and see it instantly.

It was like what if we just did almost this slideshow type format for lots of different types of content? And it can maybe be this big platform and media companies can use it or individuals can create stuff on it. Kind of like podcasts, like this visual thing that you consume while you’re looking at your phone, but like a new medium of content that’s kind of like high value.

Chris: For books, specifically, right? It was like a book.

Nathan: Yeah, exactly. For books. Yeah. Like a new visual book type thing. Although, I ended up evolving from that because books have the expectation of being really long and so these were more like shorter, basically.

After hardbound, I worked at Gimlet Media for a short while, where the podcasts that they create are all about increasing empathy and increasing knowledge of the world. And I ended up only staying for a  short period of time because they ended up deciding not to do any software stuff that I was going to do and they ended up getting acquired by Spotify.

So they just kind of wanted to totally focus on the content piece of it and let other companies handle all the technology and that was really interesting. Then most recently substack, it’s like helping writers build these independent businesses, where instead of selling their creations to someone else like a book publisher or to a newspaper type company, they can run their own business and monetize their own audience directly. If you have a thousand people paying you $100 a year, you’re making $100,000 a year.

These businesses are tough to get off the ground but once you get it to the point where it’s paying your bills, it’s like really sustainable and defensible, and it can just keep growing in a way that a salary does not grow. And so it’s great. I mean it’s like a utopian vision of what if thinkers and writers were able to make lots of money. So empirically, we’ve seen a lot of them do that, like the top writer on Substack’s making a really, really healthy living and a lot of other people are too.

Are the top writers on Substack making a living just from writing a newsletter?

Nathan: Exactly. I don’t know what publicly disclosed stats are the most recent, but if you just looked up Substack how much do people make or whatever, I think there’s press about it and it’s a pretty great model. So anyway, I’m just kind of broadly interested in that.

So it sounds like there are two aspects of making a new career move for you: financial, and passion… 

Chris: So the financial timing in your life is really important, is number one. Number two is finding something that aligns with your passion for helping make other people smarter or connecting them, I guess, even just connecting writers to their audience, this kind of idea.

Nathan: Yeah. And like using the Internet to create a better sort of system for people developing their interest and their knowledge, basically, it is broadly the way that I would put it. And part of that could mean that maybe the format is new like in the case of hardbound or maybe the economic model is new in the case of substack.

Chris: I mean, even Gimlet is really challenging the economic model of what podcasts could be, you know?

Nathan: Yeah. I mean the further I’ve got into my career, the more interested I’ve gotten in the business model side of things and the company strategy side of things where it’s not just like what product are we creating, what problems are we solving, what’s like a cool thing for the customer.

But like, how do you turn that into a defensible business that can grow and how do you kind of connect the dots between what we do and what’s in it for us and how the product works and gets used in the customers’ lives.

It’s kind of like a symbiotic relationship obviously. So the company side of the equation has become more interesting to me as I’ve grown. But the other thing I want to point out is, I don’t actually like changing things that much. I would much rather one of these things worked out really well and then I just stick with it as it becomes really big. I consider it not to be a success that I’ve worked on a bunch of different things.

I have no regrets about the path I’ve taken and I think in some ways, maybe it is fortunate that I’ve worked on a bunch of different things because I think I’ve learned a bunch of different working styles.

I learned a lot from working in different products and markets, different needs or different business models, like advertising and subscriptions versus selling courses and stuff like that. But definitely, the goal is to work on something that just works and I keep working on it for a while.

What was one of the biggest lessons you learned working at Gimlet?

Nathan: Just how different it is to be a media company than to be a technology company.

What’s the difference between a media company and a technology company?

Nathan: A lot is cultural. But also the business is a lot harder. So like it’s a really different mindset when you’re creating something that’s basically a thing that lots of other people use, it’s just got this unlimited kind of tool value, you know?

Very different to create that, than to create something that’s fundamentally consumable where it’s like, imagine if all the work you go in to creating a software product, then the people use it and then basically there’s very little value left in the thing because people have consumed the thing and it’s kind of over and done with.

That’s really hard. So you’re on this and you’ve always got to create more content. It’s hard to create that content. It’s like people simultaneously want something to be amazing and for all this energy and effort to go into it. I mean, think about how much it costs to create a book, or think about how much it costs to create Game of Thrones, right? Think about the fact that you can get Game of Thrones for like, what is it? Like $15 a month for HBO or whatever?

Chris: Sharing someone’s HBO password.

Nathan: Yeah. Exactly. It’s insane, right? And HBO makes a lot of money off of that but it’s just like, it’s really, really hard to make that stuff work because you could create that whole thing and it could have just not worked out. Like they could have canceled after season one and lost millions and millions of dollars if not that many people watched it. So it’s very risky and it’s risky with a different kind of upside than technology companies get, it just makes it harder.

I think also just culturally maybe working in a place where most of the employees are like journalists and reporters, everyone is like much more skeptical and pessimistic, I would say in a way that’s like part good, part bad.

I mean, I don’t know, what do you expect? You have a company that has an all-hands meeting and they’re like, “we just raised X million dollars or whatever” At a tech startup, everyone’s like high fiving and stuff. At a company full of journalists, everyone’s like, “wow what does this mean?” How they’re very tuned to the downside perhaps in a way that’s probably good, right? It’s probably better. It’s probably good to be attuned to that but it’s just very different than what I was used to, which was kind of funny.

What were you working on at Gimlet?

Nathan: Well basically the idea was, and I probably shouldn’t go into too much detail, but Gimlet from the beginning has primarily obviously focused on creating podcasts, right? And secondarily, focused on creating ads for the podcasts. That fuels their ability to make the podcasts.

But the big problem is that they create all this great stuff, but the content and the ads goes into apps that they have no control over, that report back very little data and give them no room to experiment with new forms of content or ads that might make listeners happier.

Are you saying that Podcast makers cannot tell who is listening or if they are listening?

Chris: So just to contextualize, you mean that this podcast, for example, is on Spotify, and I don’t know, whatever, iTunes, all these places, and the way the podcasting market is right now from my understanding and I think what you’re saying is, it’s very hard for podcast makers to know who’s listening or if they’re listening. It’s just kind of these really vague statistics. This is the problem you’ve mentioned?

Nathan: Yeah. Whereas if you were developing an app for this, and people were using your app, you would be able to know a lot more about how people are using it and improve it based on that data, and like, sort of … when I say improve it based on the data, I mean it could improve in two ways.

One is just like the mp3 file could improve. But two you can improve the form itself. Maybe you find that what people really want from this podcast is like these shorter bites where people tap on a specific question or whatever and then you have a collection of stories that are like answering their specific question or whatever.

So it’s just kind of like is there room to create something in addition to, because Gimlet’s always going to produce the normal podcast thing that goes in normal podcast apps but is there room to create something that does something different and does something that could get people to want to go to a separate app? Not everyone necessarily but just like combining Gimlet’s ability to create world-class audio with an ability to create software in a way that could do something unique.

Because really the connection between the people who create the audio and the actual software format is like totally modular. It’s basically like you got an mp3 file and you’ve got some metadata, like what is the name of the episode, what is the description. Like that’s it. Let alone if you want to throw in any pictures or anything like that, no chance, right? So, what could you do if you integrated that more to solve for making it more interesting for listeners and to maybe build community? Like what are the different things we could do?

There’s a lot of different ideas of what it could be and it’s something that the company had thought about for a long time, but never done and they got to a certain stage where they were like, maybe we do this, maybe we do this, maybe we do this. And then I knew Matt Lieber, or know him still obviously. But I had known him pretty well and when I told him that I was having to shut down hardbound because we ran out of money and I was kind of figuring out what’s next, he was like, “Well, maybe you could come to Gimlet and we could figure out what kind of technology we product we may want to do”, because we’ve been thinking about it for a while.

And so at first it was just like a consulting thing where I was like, I’ll help you think through these ideas. And then it was like, oh, we’re actually going to build these ideas. And I actually ended up leaving pretty quickly, more quickly than I wanted to because at first, they were going to do the ideas, and then decided not to.

It was just kind of the question of like company strategy that had a lot to do with how fast Spotify is growing. So they ended up getting acquired by Spotify and they ended up sticking with just doing content which makes total sense. I think it’s the best decision for the company, but it was cool to be able to be a part of it and to help them think through well what if we do software.

And we did some pretty cool stuff when I was there. We made an Alexa skill. We redid the website. We did a lot of data stuff and came up with a bunch of cool ideas for apps that maybe someday, someone will build something with that.

How do you build an Alexa skill?

Nathan: You know it’s actually pretty easy technology wise because you basically just have to set up when someone says this kind of thing and you give it a bunch of examples of like it should trigger this action where they say stuff like this, then just return this response or whatever.

So it’s very pure like kind of HTTP, you don’t even need to play any audio file or something like that, it is like you don’t really need to have any audio or anything like that. It’s all just totally like optional basically. So you can just return some text and Lady A will just speak the text to you.

To make an Alexa skill, do you have to know how to code?

Nathan: The way we did it is, we actually partnered with a company that makes Alexa. And they created the first version of it and that helped me kind of figure out what it did and then I kind of took over from there to finish it up because it was mostly done but I was kind of the one who’s like maintaining it and making sure that any little tweaks we wanted to add, we could add.

Nathan: But really it’s just like, basically a JavaScript thing where you just you have some functions that you define as like standard things of like listen on the Alexa response received event or whatever. If it’s this thing.

And you have to define some stuff in their interface where it’s like that’s where you set up the examples of the … I’m forgetting all terminology because it’s been a year. But basically, long story short, once you learn a few kind of domain-specific things, it’s pretty much just writing JavaScript.

For Echo, did you guys think about how search rankings might work and marketing Gimlet podcasts?

Nathan: Yeah, we did. I mean, a huge part of it was like making sure we had a good relationship with Amazing and that’s one of the sort of advantages of being a part of a company like Gimlet that’s been able to build a brand already in a separate space and then we could take it to Amazon and we had enough credibility where they were willing to chat with us and we could have people there that we talked to and stuff like that.

We’re able to work out some good stuff around the launch of it to make it extremely frictionless. The thing was called Chompers, and so you basically say, “Alexa play Chompers.” And you don’t even have to have the app installed or anything like that. It knows what to do. Thanks to our partnership with Amazon.

It plays this cool thing for kids that’s basically like a toothbrush timer except it tells you stories or sings songs and has jokes and all sorts of stuff. So the basic problem it’s solving is if you’re a parent, it’s very hard to get your kid to brush their teeth and it’s basically impossible to get your kid to brush their teeth for two minutes, which is how long they’re supposed to.

Dentists recommend it and kids tend to get cavities and stuff if they don’t brush their teeth, but it’s very boring for kids to do that so it’s a big pain. And so, basically we turned it into like a treat where it’s like, in exchange for brushing your teeth you get this fun content.

It’s a pretty cool thing and we partnered with Oral-B who is like the main sponsor of it and they just sponsored the overall thing. There wasn’t like a lot of advertising or anything like that in it because it’s a kids thing. But it won a Cannes Lions so that was pretty cool.

And yeah, I helped a lot with figuring out how the product should work. The fun kind of game mechanic type thing we put in was streaks, so at the end of it, it gives you like a reward telling you oh, that was one and do this tomorrow to get two in a row. Then we just keep kind of incrementing the counter basically.

So as a developer (or user) you can write data to Alexa/Echo and keep it in their database?

Nathan: Oh yeah. You can have a database. I mean it’s just kind of like a Node app, or Express app where it’s like you get something for Amazon that triggers stuff to happen but then what happens after that is like you can have database.

What is Gimlet’s Chompers app? Is it a podcast or an app?

Nathan: Yeah. Well it is basically a podcast designed for Alexa and I don’t know if it’s on Google Home yet or not, but that was in the works when I was leaving. But basically, it’s just a different form of a podcast where it’s like a two-minute thing that you activate through your Alexa that we create.

But the process of actually creating the content had a lot in common with the process of creating like a 40-minute episode.

What interests you now that you’ve left Substack?

Nathan: Yeah. From what I learned at hardbound I think there’s a lot of potential value there. The thesis of hardbound was basically like if you can create really good content in a new format where you sort of integrate the content with the format to create a much better experience than what you can on just sort of writing on the Internet or having video or podcasts, that it could create a different and special enough thing that people would actually really like that. And a lot of people have done this.

I would argue Headspace and Calm are examples of this where they could be a podcast, but instead, they created an app. They sort of built it into tracks. The way they structured the thing sort of integrates software and content in a way that solves a problem which in their case is like learning meditation.

It’s funny, Sam Harris just launched one too for meditation called Waking Up. So it’s like you can get pretty deep in it, and then the other thing I kind of learned with substack is like these sort of subscription content businesses can work really well. Like you can keep costs pretty low, and you have a pretty defensible business and it’s a lot of fun to make if you like creating that content.

I have no clue what I’m going to do next. Open to lots of different things but part of me is interested in doing something like that. There’s different parts of hardbound that I can imagine a version of that’s like take everything I learned and then give it another go. Because we did even get it to the point where like if I were the only employee, we could have gotten pretty close to the point where it was paying my bills. But it’s just really expensive and hard to create a lot of that content and so it just wasn’t feasible to do in the kind of bootstrap model.

But I think I can figure out another version of it that’s more bootstrappable.

Chris: Yeah. I mean, I think the examples you gave are really novel, really interesting and that maybe are underappreciated as far as the success of Headspace, which is from what I understand a pretty huge company now as well as Calm and if you look at the content that they make, I mean I don’t want to undercut it, but it’s mostly audio.

At least Calm, which is what I happen to have. And yeah, it’s fairly scalable, I guess that’s maybe one of the things you’re looking for in the next project that you work on. Something that can be maybe less intensive time wise or money wise to grow.

Nathan: Yeah. And to me, one thing that’s interesting is nobody really knows at the outset of one of these things how big it should be. So like it’s in this weird space where it’s like maybe some of the more ambitious ideas, if they work really, really well would be great candidates for venture funding. Like theSkimm is a great example of this. I mean it’s an e-mail newsletter, but it’s also a lot of other things now and it’s a huge business doing amazingly well.

There’s another similar one called Shine. It’s a text message, then they built an app, so what you do is, you anchor on one thing and then you reinvest and you sort of extend it.

And some of them might end up being just pretty good, like lifestyle businesses. Some of them may end up being really big, great venture capital investments. And the problem is, upfront it’s sort of hard to tell usually which is which. And it’s not just for subscription content businesses, it’s also like lots of things, right?

So another thing I’m sort of interested in is, initially the way you would get funding for something is venture capital and then that was kind of like thesis right? So the antithesis was stuff like or there’s other examples of specific funding companies that aren’t trying to be giant unicorns. They just want to build a real business and it’s going to be not necessarily that big.

But I think it’s kind of rough because you don’t actually know what it’s going to become. From the outset, you’re not necessarily setting out to start something that’s a giant or something that’s small and intentionally not trying to be big and you’re just going to like, instead of ever reinvesting in the company, you’re just purely going to squeeze all the profits into your own pocket.

I think the more realistic approach is like an entrepreneur upfront knows that they want to do something. They think it has a really good chance of achieving some success. They have no clue how big that level of success could be. If there’s lots of ways to reinvest into the business to make it grow more, they definitely want to do that, but also they don’t want to kill the company like over nothing just because it doesn’t look like it’s on path of becoming a unicorn.

And so I think it would be interesting to try and come up with some model of funding early-stage stuff that’s helping people who aren’t already rich to quit their jobs, work on building things that seem like it’s got an amazing chance of being at least a good business and in that case, it could work out okay, and it could have more of an type model of taking dividends or something like that. But also if it becomes bigger, it would work like you have equity in the thing and so you end up making returns that way if you want to.

What is And why do you like it?

Nathan: is basically this guy, Bryce,who used to work at O’Reilly AlphaTech Ventures I think. I don’t want to put too many words in his mouth, because I don’t fully know the motivation but from what I understand of it, it’s basically like a model for funding companies that are real revenue generators and could use additional funding in order to grow but don’t want to do the venture capital model of selling equity and you’re trying to become this giant thing and you’re willing to do kind of crazy stuff, long shot bets that probably won’t work out and will kill the company if they don’t work out, but if it does work, could make you a unicorn.

So the idea is like, instead of buying equity and getting paid whenever there’s a liquidity event like the company gets bought or IPO, something like that, you make a loan invest in the company and then they pay it back to you over time in the form of dividends.

So, I don’t exactly know the legal financial structure, but it’s basically a model that works for companies that aren’t trying to get bought or IPO or something like that.

Chris: Yeah. That’s really interesting and I have that with a lot of people that come to me and want to start to build something and I think what most people don’t understand about venture capital, which you hit on there, is that you’ll tell them your idea, you’ll get money. And there’s only like two ways that the investor is going to make it, either IPOs, which means go to Wall Street and become huge, or you get acquired.

There’s really only those two ways but there’s not a way to just grow a company. Like very few people will just invest in you for dividends, or at least that’s not the Silicon Valley kind of story, rags to riches story everybody’s telling. Whatever that is.

But there’s something really pure and nice about just building something because people use it. It’s a viable business and I’ve definitely been at companies where they’ll kill the thing and I think that’s what you’re talking about. If you’re not going to become huge, it’s like why are you even trying? Which is like really self-defeating.

Nathan: Yeah. I agree. Gimlet and General Assembly, were both companies that raised a lot of money and it limited certain options. I don’t think that they both had good exits and it was a good outcome I think for everybody including the investors, but they didn’t really have the option of just growing as best they could but not like killing themselves to be giant or something like that, you know?

And so I think the other model of funding is pretty good but it also kind of presumes that you’re not going to end up being really big. Because the way it funds it is like, it’s like first of all kind of the signal and the statement that it makes of taking funding from those sources and then second of all, the actual legal and financial structure.

So I think it’d be really interesting to start something where it’s just unclear and just admitting it’s unclear at the early stage if this is going to be a lifestyle business or a giant unicorn.

And as a founder, you just want to build a real business that works and makes you happy and makes customers happy and there’s different ways that you could make money off of that. One way is being really profitable and issuing dividends. Another way is being giant and selling the company or IPO or something like that and you just in the earliest phases, don’t know.

I think you could engineer some form of investment vehicle to enable that for people and that could be good. So I’m kind of interested in that too, although I’ve never invested in companies and I don’t know. But it just seems like maybe there’s a need for that because the reason why I thought of it is because that’s actually what I would want right now because what I want to do next I have a specific idea of what it would be but I don’t know how big it would be.

I think it could be really big but I don’t want to lie to a VC and be like, “Oh, I’m definitely going to make a really giant thing. I think there’s an amazing chance of it being real, and a just maybe slim okay chance of it being giant. And it’d be nice if there was a way to make money either way where it’s like, as long as it’s kind of profitable then that’s good.

Chris: I love that third option. That’s really cool. I mean, this isn’t at all a solution but the first thing comes to mind is like maybe between Kickstarter and Crypto there’s like a way that you can crowdsource the money and get people excited. I don’t know. Just random thoughts. But yeah.

Nathan: That is an interesting idea. Yeah, yeah, yeah. Totally. I don’t know, I’ve got to think about it a little more. I literally thought of that earlier today on a phone call with one of my former investors from hardbound who I was talking to about what I would want to do next. And so that’s a very fresh, unpolished thing. But yeah.

What resources or websites do you use to stay up to date on technology?

Nathan: Oh man. You know, I don’t really focus on staying up to date on technology. I know how to build basic things in like Rails and Node, React and Express and like I’ll use different things for different kind of purposes.

For me, the default is probably Rails because it’s just so fast and I know the basics of it so well that if I want to spend something that’s probably the answer for me. And so, I think about what kind of thing I’m trying to build and then if there’s like a thing where it’s like, oh, I need to learn how to do this thing probably using like Canvas, how do I do that or whatever? Then I’ll Google how to use it in Canvas and there’ll be some stuff that’s like new and I can use and there’ll be some stuff that is old and I can use, and it doesn’t really matter as much when it came out. Yeah. I don’t try and stay up to date on technology.

Are there any tools or hacks at the moment that really save you time or you use everyday, or you think are exciting?

Nathan: I would say maybe my biggest time-saving hack is to not worry as much what is cool and what people are using. Substack uses Node and Express and React and I thought it was really powerful and nice and React’s pretty good but it’s just so much easier to use Rails.

And I know it’s not as cool but it’s just so much easier and so I worked out a little thing for fun right now, and I just turned back to Rails because I know there’s not as many developer jobs in there. It’s not as fast-growing but frankly, for what I need right now, I need to save myself time and to build thing this faster and Rails let’s me build it faster.

Chris: I love it. I think that’s the best advice because there’s always this noise, there’s always more in trends and I always tell my students when we talk about what digital literacy is, I think it’s just knowing the right tool for the job and there’s a lot of noise out there. So you just gotta do what you think is best.

Nathan: Yeah, and if you want to be the kind of software engineer that is like on top of all the latest stuff in the JavaScript world, then it’s awesome. It’s good for you to learn the fine points between Babble and Webpack and gulp or whatever. You know what I mean? Like all the different stuff. And I just know that’s not ever going to be my thing, and so I just don’t worry about it. Yeah.

Chris: Hey, Nathan, it’s been so great having you on the show. Thanks for chatting today.

Nathan: Yeah. Thanks so much for having me. It’s been awesome.

Is there any place that people can go to learn more about you that you would like to send them?

Nathan: Twitter, I am @nbashaw. I need to update it to be my new last name.

Chris: Love it.

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How I Learned to Code with Nathan Baschez
How I Learned to Code with Nathan Baschez
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Chris Castiglione Co-founder of Adjunct Prof at Columbia University Business School.