How Sahil Lavingia built Gumroad, a company that allows people to sell directly to their audience

Joining me is a Mixergy fan who used to listen to me when he was in college.

By the time he quit college, he had already built and shipped about two dozen websites and software products.

Then, one of his ideas hit. And hit big. So, I invited him to tell the story of how he did it.

Sahil Lavingia is the founder of Gumroad, which enables creators to sell directly to their audience.

Sahil Lavingia

Sahil Lavingia


Sahil Lavingia is the CEO and founder of Gumroad which enables creators to sell directly tot heir audience.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of, home of the ambitious upstart. Boy, I’ve got a returning guest here, one that I’ve been really looking forward to having on Mixergy. Joining me is a Mixergy fan who used to listen back when he was in college. By the time he quit school, he already built and shipped a couple of dozen different websites and software products. Then one of his ideas hit and hit huge.

So I invited him here to tell the story of how he did it. Sahil Lavingia is the founder of Gumroad, which enables creators to sell directly to their audiences. For example, if someone out there has a collection of icons that he created, and he doesn’t want to mess around with merchant accounts, and creating pages convincing people that it’s okay and safe to buy from him. He can get rid of all that hassle by just using Gumroad and everything just works. All he has to do is focus on his customers and know that they’ll be taken care of by Gumroad.

So I invited Sahil here to talk about how he did it. This whole thing is sponsored by Later on I’ll tell you why, if you’re looking to grow you’re mailing list, you should check out But first, Sahil, welcome.

Sahil: Thanks for having me.

Andrew: Is it weird that you’re in the other office here at my office, and we’re just talking on our computers from different spaces?

Sahil: It is a little weird. I didn’t know if I was supposed to pretend I was somewhere else or not.

Andrew: [laughter] You’re just down the hall, we got you some office space. But I appreciate you doing it here. We wanted to make sure that we had a crisp internet connection, that you came across great. And you do.

Before I get into Gumroad, and how you got customers and how you look make it look the way it does… I mentioned at the top of the interview that created a couple dozen different products and shipped them. One of them was Dayta. I want people to get a sense of the way you were thinking. What was Dayta, D-A-Y-T-A?

Sahil: Dayta was an app for the iPhone that I built over the course of a week, actually. I had this need, I wanted to be able to track relatively arbitrary data points in my life. Things like, what time I woke up, how many hours of sleep I got, how many pushups I did in the morning, how many minutes I meditated, or just my arbitrary happiness score out of 100. I thought it would just be really cool to track that information and also potentially compare that to each other. Does how many glasses of wine that I drink correlate with my happiness, for example? I thought that would be pretty cool to know.

Andrew: Did it correlate with your happiness?

Sahil: I don’t even know. [??] Definitely sleep did. I thought this would be cool. The problem that I saw was that there were all these different apps in the App store that would be “water counter” or “push up counter”. They were all just the same app, the only difference is unit. Instead of glasses of water, it’s pushups or whatever. So I built this sort of universal data tracker that you put in the unit. You’d say “glasses,” or you’d say “pounds,” or whatever, or you could leave it blank in the case of happiness, for example. It would just show you graphs over time. It was very simple. You’d wake up, you’d input a number, increment it up or down.

Andrew: And one of the cool things about it is you built it in public, right? You were blogging about how you did it. How long did it take you to do it?

Sahil: I did it over the course of a week, actually. So I called it “One Week App.” Actually, it was almost stupid. I started on a Sunday, and ended on a Sunday. I really didn’t know what I was going to build. I woke up Sunday morning and had some ideas but actually hadn’t decided. Sunday morning I just picked one and ran with it. Luckily, I made it to the end. I put it in the App Store, and it got approved in a week. It was pretty successful.

Andrew: What made it a success? How many people used it?

Sahil: I think over the course of its lifetime, it’s no longer in the App Store because I didn’t want to maintain it any more, it got to maybe in the hundreds of thousands of users. That was really cool to see people use it to track things. It was pretty neat, one of the bigger things that I have built over time.

Andrew: And then at some point you came up with a photo-realistic pencil design that changed everything. What is a photo-realistic pencil design? What made it so special?

Sahil: It sounds like a movie trailer. So fast forward two years or so, I wanted to really focus on icon design. You sort of see all these cool things on Dribbble, Behance and all that stuff. So I spent four hours or so messing around in Photoshop trying to figure out how these guys did that. And I did it. I sort of figured out. This is a bunch of layers and highlights and chatters, and this is kind of cool. And sort of, the way my brain works I was just like, this took me a long time it should have taken me less opportunity I should make it really… I should give this… you know I think other people would benefit from this maybe I’ll try selling it. And so I did.

I was like, okay I have a Website I had a Blog at this point I had a Twitter account, I had a Gerbil account. I felt like I had the digital file, you know I was entirely digit so I didn’t really have to deal with it too much [??] issues a things.

And so, you know I put like buy button on a little single page on my Website, it’ like buy this icon and…

Andrew: And sell this icon you’ve created.

Sahil: Yeah, and like that’s what I wanted to do. So I tried doing it, it was actually very difficult to figure out just integrating PayPal and like a Website and that. Basically, I spent like an hour doing it, thought it was too difficult and then beyond that I felt like, I’m like a pretty good candidate to this like I knew how to code, I had a Website. I had a lot of pieces right, I just didn’t have the glue.

Andrew: I don’t understand. What’s the problem? Why couldn’t you just say, you know what I’ll go to use a PayPal buy button. And then at the end of the PayPal buy button anyone who goes through that whole process will have given me a buck and I’ll get to give them the pencil design that I created.

Sahil: Yeah, so there’s just like one I had to put this really ugly PayPal button on my site which even that just took me a little while to figure out because like they have this weird form where like you have to create these buy buttons. But they’re not really associated with anything there just like arbitrary buy buttons that you create.

And so like technically someone could sort of change the HGML and then make the buy button link to a page that will charge a dollar or two dollars. And then there’s no integration right. So basically I would get an email saying, hey someone paid you a dollar, and then I’d have to manually just send them the icon. Even automating that was difficult.

And then there’s like the validation that did they pay enough, but if someone paid less it’s just like a little complicated. And I think when you’re trying to you know selling a product to somebody you don’t want to have that experience together. You know, you want it if they’re on their phone, or you know they don’t speak English, when you’re asking for money from somebody I think it’s important to sort of give them a really, really, really good experience. And I couldn’t do that. It was just not a good experience and…

Andrew: What did you decide to do instead?

Sahil: So I decided over the course of a weekend to build Gumroad, I decided okay if I wanted to give this away for free I would have put it in Dropbox, or I would have uploaded it somewhere else. And I would have gone to Link and I would have shared on Twitter or Gerbil and I could be like, hey if you want this thing click this button and you’ll get it.

And so I was like I wanted to be that easy, the only difference would be I want to charge a dollar for it. And so that’s what Gumroad was it was just like almost like a file uploader plus a credit card form.

Andrew: I see, if I wanted to share an image on Twitter I can get a single URL and share that image. But what if I want to sell that image, then I have to have a URL that leads to this whole process. And that’s too much trouble and you’re saying I want to make it that easy. The whole idea is one URL that automatically sells, and delivers, and handles everything for the customer. How long did it take to make that?

Sahil: Around 48 hours.

Andrew: 48 hours, to build this whole thing.

Sahil: Yeah, 48 hours, and 10. I think 22 hours of actual work.

Andrew: What happened to the other hours?

Sahil: Sleep.

Andrew: I see, okay.

Sahil: Sleep and yeah…

Andrew: So you had it, you tried to sell it. Did people actually buy the pencil?

Sahil: Yeah, I think I make like 60 bucks or something. So you know.

Andrew: Do you think people really wanted the pencil or they were more interested in how Sahil was selling the pencil on line using this new URL scheme?

Sahil: Probably the later to be honest. I think most people were probably like, I just want to see what this dude built.

Andrew: This is going to cost me a buck to see what this guy built, and he’s so prolific he’s always creating interesting things, let’s do it.

Sahil: Yeah, and it did pretty well I think like I don’t know 15,000 people saw it the first day. And I think people were just in general excited about like trivializing something right. Like making it so easy that it requires almost no thought to sell a product. I think people were pretty excited about that idea.

Andrew: I see how it works. One of the things we’re going to talk later on about is how you and Gumroad as a company just obsess about little designs that most people wouldn’t even know exist. But here you are telling me in 48 hours you created something. It couldn’t have had this kind of polish. In fact I know it doesn’t, it didn’t because I went to Internet Archive and saw what it looked like. What did you make… your smiling when you’re thinking about how used to look what irks you the most? Or what about it feels very unlike your design today.

Sahil: Yeah, definitely the font choice. I chose a weird font. And there was no logos like this brown big just Gumroad in rounded letters saying, I think was like [??] arrow rounded or something. I just think it was yeah, I think it worked for what it was. It was just a super simple like the homepage had the sign up form in it, you just signed up there was no JavaScript it was all like inline forms and stuff, , but it worked. That was a lot more important to me. It was did the thing just work?

Andrew: What did you leave out of it that would shock people today outside of the logo? What about the functionality?

Sahil: The craziest feature that we left out, there’s a couple. One was that we didn’t actually allow file uploads. It was so basic I didn’t have the time to even build file uploading into the service. So it was sort of assumed that you had the file already uploaded somewhere else. So it could have been in Dropbox or it could have been on your own website server or AWS if you have a sort of public bucket on AWS. There was encryption of the link, so if you got the link at the end, you could share it out with as many people as possible.

Andrew: Yeah.

Sahil: And then the other thing on the buyer side, we actually didn’t even require emails. It was so simple that you just typed in your credit card information and you got a link. The problem is then you refresh the page, it’s gone.

Andrew: I see. So by you, you mean the customer. You got your user’s email address and then you allowed your user to sell, but once your user sold to the customer, the customer’s email address wasn’t saved anywhere, and if the customer ever needed the order again, he had no way of getting it. There’s no way of getting that pencil if he bought it from you. I see. All these things were left out of it. Did it hurt you to leave it out or was it just a simple calculation, “Hey, I’ve got to get this thing out as quickly as possible?”

Sahil: Yeah, so I sort of operate on the model that most interesting things you can build in a weekend. I think that’s a pretty good filter. For something to be really successful and useful, it has to be pretty fundamentally important. There has to be some pretty core change to it. So you can think about Twitter or Snapchat or Facebook, right? The actual essence of the service, you could build in a weekend. Any of these services, you could do that. There’s a lot of nuance to get it from 1000 to 1 billion users. A lot goes into that, and there’s a lot of nuance, and you need a big team, et cetera, but I think you can sort of prove the crux of the problem in a weekend. And everything else, like the login system, the design, the logo, the domain, everything else, basically, you should save as much time on.

Andrew: What’s the one thing that you were trying to prove then with this?

Sahil: I wanted to prove that selling something could potentially be as easy as sharing it for free.

Andrew: I see.

Sahil: If you wanted to sell something or share something, the reason you share it instead of sell it is not selling it is difficult. That should be the reason, and I think we proved that.

Andrew: Were you also trying to at all test to see does anyone want to sell as easily as they share using a link or would anyone buy something that worked this?

Sahil: Honestly, no, because I think now, yes. Now it’s more a concern for us, but I think in the beginning I just assumed if it was this easy, people would do it.

Andrew: I see.

Sahil: Maybe naive of me. I was like, “I’m sure people want to sell things that was just too hard to sell,” because I had a couple situations myself. And then on the other side, for me, if it’s so easy to buy, I don’t really think that would have deterred anybody. It actually turns out that that does matter and it is a concern, and we’ve done a lot of stuff to optimize . . .

Andrew: What is a concern?

Sahil: That conversion goes down because it’s just weird. It’s just like it shouldn’t be this easy to buy a product sort of thing.

Andrew: I see. If you just give someone a link to a page on Gumroad, a site that they don’t know, and all they have to do is buy that product, it might just not be enough.

Sahil: Exactly, yeah.

Andrew: I see.

Sahil: You see crazy sort of scroll landing pages that sell you on a product, and that stuff works because you commit time and you sort of have this momentum as you’re scrolling that you’re sort of convincing yourself that you want it, and then by the end of it, it’s sort of enough to get through the wall. But if there’s nothing there, if it’s just the thing and then a buy button, that might not be enough for you to get through it.

Andrew: I see. I hadn’t thought of that that when people scroll through one of those long sales pages, even if they’re not reading every part of it, you’re saying that just by scrolling, they feel more committed to the product and the shopping experience.

Sahil: Yeah.

Andrew: Kind of like when you walk inside a store as opposed to just peeking through the door. The more you walk in, the more engaged you are and more likely you are to buy. All right. So you were testing that. Did you get anyone to actually use it, to not just buy from you, but to try to sell something with it?

Sahil: Yeah, there were quite a few people in the first 24 to 48 hours that ended up setting a product, even an icon set or a small video game they made or an album of music. A lot of people were just messing around. Most people were just testing it out and trying it out. I think someone sold some data, some Excel file they had that was a list of something interesting. But, yeah, it was mainly people playing around with it. I don’t think there was anyone that so quickly went from what is this new thing to making a thousand bucks on it.

Andrew: I kind of feel like the reason that this happened, that you go so many people to test it out and to buy for a buck just to see what it’s about is because of the kind of person who was following you. You’re actively showing your work as you build things out so the people who came to check out your blog and joined your mailing list were people who were curious about what a maker can make in short period of time. What a guy who has ideas and can see them through can build, right? Was it your sense too that that’s the kind of audience that you built for yourself?

Sahil: Sure, yeah. I think a lot of my audience are people like myself who like building things quickly and shipping things. They’re more excited about building things than they are about talking about building things. And so yeah, I think that’s definitely a part of it. I have an audience that is more prone to trying things out; whereas a lot of people could look at Gumroad and be like, “No, this is weird. This is too different than what I’m used to,” right? The portion who’s used to iTunes or Spotify. And that’s fine.

Andrew: So how did you build such an audience for yourself?

Sahil: I think I just built a lot of things and I got relatively good at trying to describe why I built something. I think that was important. I was never, “This is a thing I built.” It was always, “This is the problem that I had and this is how I solved it.” It’s always interesting to see why someone built certain things like origin stories of companies and things. It’s pretty fascinating. I also think, I never built anything to make a lot of money beyond when I was 15 or 16 and just messing around, and so I think my audience was never like, “Oh, you’re just trying to make me pay $15 for something.” It was always like, “Oh, this is some really cool thing you made because you thought it was too hard to get a browser page from your website or from your desktop pr laptop to your phone or to track your weight over time or do X-Y-Z thing.

Andrew: You’re also a good promoter though, right? You didn’t just say I’m going to blog over the next week. In fact, let’s take it a step back. You didn’t just say, I’m going to launch an app within a week to see if I can do it. You said I’m going to launch in within a week and blog about it within a week. And you didn’t even stop there. You said others need to know that I am doing this so I get that kind of engagement. In fact you told me, this is our second time recording this because the first time we had tech support issues so the recording was hard to even hear. But I do remember in that first attempt at this interview, you told me that you went after the Apple blogs in a certain way. That’s what it was. How did you do that?

Sahil: Yeah, I basically just cold emailed. This is a strategy that works to this day. I made a list of maybe 100 people, 100 blogs that were probably going to be interested in this sort of thing. Either they had audiences that wanted, of app developers or, here’s an interesting consumer story too. These apps that people use on a daily basis, how are they made? They just appear on your phone. I had no idea how Facebook existed. I assumed some big company built Facebook. I didn’t realize it was a bunch of college kids or not even. So I thought that was interesting, right? So I basically spent, I think about two or three weeks before the week that I decided I emailed just like 127 or something blogs being like, “Hey, I’m doing this thing.” I built a little website called that had a little put it in your email and I’ll email you when it starts. I got, I don’t know, 2000 or 3000 emails through that, and then MacWorld wrote about it. I just think there was no real financial incentive.

Andrew: I don’t get that. You said a moment ago, “I used to build things without trying to get rich off of them.” I don’t get that mentality. You’re telling me that you were growing up building stuff and you didn’t think, “Look at all these guys who are making a lot money. I think I could do that too. Look at all these guys who are getting to do things because they have money. I need to make money also in addition to being creative.”

Sahil: Yeah, I think I’m sort of 50/50 on that. I mean money is cool and important and it’s a really good way to figure out if what you’re making is valuable to a lot of people, and I definitely, like with Gumroad I think it’s incredibly important to give people ways to, we pay you basically, right? But I also think there’s an incredible amount of value in just building 1. Your skill set and 2. Your audience, right? And it’s this sort of model of, a lot of people call it give, give, give, ask. It’s like you give things, I think you do a phenomenal job that’s, you basically help people with very little incentive that’s sort of on this one to one basis but then when you have a premium product that you’re trying to sell or whatever, then you have a massive list of people that have been . . .

Andrew: That have been following along and getting all that benefit, and now they’re much more open to buying from you.

Sahil: Yeah, and I don’t think it’s dishonest. I think it’s actually the most authentic thing you can do. It’s like, “Hey, I really like doing this. The absolute best thing is if you pay me directly for doing this, and then all I can do every day is this thing. I don’t have to do this for fun and then work a night job to make money.” It’s the same thing, which I think is pretty cool.

Andrew: All right. Let’s continue with how you built up Gumroad. And by the way, how big is Gumroad now? What kind of sales are you guys doing annually?

Sahil: We don’t disclose that yet. I can tell you that we have other 10,000 creators that have sold products through Gumroad, which is pretty cool.

Andrew: How much money has Gumroad processed?

Sahil: A lot.

Andrew: Is it tens of millions of dollars?

Sahil: It’s at least that, yeah.

Andrew: At least $10 million. Is it more than 30?

Sahil: No comment.

Andrew: Really. Okay. What are you waiting for before you can say what the numbers are?

Sahil: I don’t know. I feel like at some point, when we’re a public company, we’ll have to disclose those numbers.

Andrew: Oh, you’re thinking going public as an IPO, and at that point, you’ll have to disclose. Let’s wait for the connection to catch up with us. It’ll take about a moment. Yeah. Are you thinking IPO, and that’s when you’re going to talk about it?

Sahil: One day. There’s basically two options. There’s multiple, but the two main options are we get acquired by somebody or we IPO, we stay independent forever. And for what I’m trying to build, I think it’s important that we focus on the latter target. I don’t think we want to be acquired. No one at the company is excited about Gumroad because they think it’s an acquisition target. Everyone really believes in what we’re building and that we can build it ourselves independently of anybody else and do a really a good job.

I think what Kickstarter does is actually really awesome where they have a stats page. They don’t have super granular insight into it, but you can sort of see how much money they’ve processed over all time and things like that. And I would love to do that at some point. I just think that right now there’s not a ton of benefit to doing it and it’s sort of this asset that we can sort of hold close to our hearts and then when we’re ready, we can potentially use it as a way to grow or whatever.

Andrew: For every $10 million in sales you guys do, you get half a million I think it is in commissions plus $0.25 per transaction, right?

Sahil: Exactly.

Andrew: Your fees are 5% plus $0.25 per transaction. Let’s get then into how you grew. So now you have this thing that people are using. They’re spending a buck, they’re getting your design, they’re testing it out to do things like sell spreadsheets. What’s the next step. What did you build next in it?

Sahil: Yeah, so we have this pretty simple question actually that we’ve started using to sort of validate what we should build next, which is what are creators doing every month that they shouldn’t be doing?

Andrew: Related to selling.

Sahil: Exactly. Right. So there’s two categories. There’s things that they’re doing to make things, and then there’s things that they’re doing to do everything else. And we want to sort of do as much of the second category for them as possible, automate everything, just remove as much time and hassle and stress and expertise required so that they can focus on what they love to do, which is . . .

Andrew: Mainly create. And you said that in the first version, anyone who wanted to use it had to have an account with AWS, which a lot of people don’t have or even know to upload the file to Dropbox and then tell you where the Dropbox. So today that’s not necessary. They can just upload it to Gumroad. Gumroad will give that product to the customer. What was the first step then that you took towards getting that kind of automation, that kind of level of support for creators?

Sahil: Yeah, we just basically drew a picture. I think at Gumroad we sort of pitch it as we’re for all creators, but I think when we’re building products, it’s useful to frame it around a certain more granular use case. So for example, there’s a musician that wants to sell an album to 30,000 listeners through SoundCloud. That’s where their audience lives. They want to sell their first mixtape, their first album. What goes into that process up until the sale?

And part of that is making the thing. I don’t think we’ll sort of get into music production for a while, but then it’s packaging it up, generating these mp3s, taking all these mp3s, putting them in a zip file, maybe having some artwork as part of that, uploading it somewhere, taking that link, giving it to use. Then on the consumer side, you get the zip, you download the zip, you download this zip, you double click it in our archives, you have the things, if you want to listen to it on your phone, you can sort of copy them all, drag and drop it into i-tunes, sync it to your phone, and then you’re done.

Andrew: You know what? And then you’re done? That’s a big process. You know what. It seems natural to me. I can imagine doing all that, but I can see now that you described it like that, that’s a big pain in the butt. And so you will sketch it out, you literally write it out step by step and say what can we eliminate here for them?

Sahil: Yeah, exactly.

Andrew: You do?

Sahil: Yeah.

Andrew: We do it on white boards.

Sahil: On white boards? I see. So that’s a lot of steps. How do you prioritize? How do you know which one of those steps you should eliminate first?

Andrew: Typically, it’s the first step, right? And so I always think about the first part because I think no one will get to the second step if the first one isn’t really easy, right? And so always work on the first thing and so for example, for us, that was like first of all let’s just get the uploading to happen because that was just annoying. Like with those that required another service and all of this new insight into how hosting works and those sites doesn’t make sense and so the first thing we did was to upload this zip file to governor, right?

So we did that, then we realized the whole zipping and unzipping on either side we can solve because if we can say instead of uploading these zips, upload all of your files separately, just say upload all of your mp3s, the alpha merits, etc. And then try first on the fiery side and he can just download them separately or what have you and so we did that, then we said okay, this is great but on the consumer side you still have to download, what if you buy a podcast you just want to listen to once and that’s it or a movie and want to stream it so we built that in line, right?

So next to every tower depending on a specific cost and type if it’s a video you can watch it, there’s a watch button, if it’s an audio file, you can listen to it, if it’s a book, you can read it, we poked all those things, right, then we realized this is awesome but if you’re on your phone, certain times it won’t work right or you might be offline or you might have a bad connection, you want it available on a plane so we built that, we watched it actually last week where you could actually sort of sync purchases you bought on the web with your phone and then you have them locally on your web with your phone and then you have them locally on your device and you can consume them however you want.

So we sort of just always have been thinking about what does it create an app to do to give their users an amazing experience and how do we bring that as a part of the government experience? It might happen. I’ll be editing and stuff and zipping half the tubs so the government says how can we own that? How can we sort of be part of that? And then because we’re a part of that to do it better than they’d be able to do it.

Sahil: I personally overlooked something that seemed obvious, but isn’t, which is how you get that list of steps? Always when I publish something I assume that everyone is going to download it the way that I do. Everyone is going to through the same experience that I do, but they don’t because they’re not me, because they don’t understand the site the way that I did. How did you know what the steps that they were taking were and where their major frustrations were?

Andrew: Honestly in the beginning I had no idea. When I built it, my goal was to be done. The goal was to take what the creator put on our service and then give to every consumer the same thing, right? If you uploaded a zip, you got a zip and that was it. And it actually turns out, you hit a wall. That works for people who are creators and consumers that are relatively tech savvy but that breaks pretty quickly so as we grew and it didn’t happen all at once like “Oh crap! It’s all falling apart. People didn’t know they could download things and it’s all crazy.” It was just over time, we had like this ring, a small ring of tech savvy people and then as we got bigger and bigger and bigger the fringe of people didn’t know what unzipping was so we had to solve that problem they didn’t know how to even though it was already unzipped. They didn’t even know what downloading was.

Sahil: How did you know that? I imagine the first really tight circle you know because you are them, you are that creator. When you go beyond it’s unfathomable to be that people don’t understand what zipping and unzipping is but as you say that I realize that of course they don’t know. Many people will say upload when they mean download and not understand the difference between the two. How did you know this was a problem someone has. What do you do to do that?

Andrew: And the connection, yeah, what did you do? We’ll give the connection another chance.

Sahil: We have all of these creators over millions of buyers and so we did a great way for us to get feedback because they’re really compassionate because they make money through us so when three or four people email us and say i bought it on my phone or on my tablet and I don’t know what to do or hey I bought this form to get my movie. They don’t know how big it is, they just say I bought a movie about your thing, and I can’t watch because I’m on an Android Tablet and I’m in the middle of X,Y,Z and it’s like, I have terrible internet. In like [??] movie I’m never going to be able to watch this thing, right. So it’s 16 hours of manning or whatever.

And that was a great way for us to filter feedback because it was coming through like this sort of tiered approach of like really not tech savvy people would email creators for you know… and now we do a better job sort of trying to get in front of that and actually just doing the support directly.

And then creators would be like, hey you know I have 30 people out of… you know it might even be like a small number, they might have sold a 1,000 copies and four people emailed, but it still hurts. It’s still like crap, four people had a bad experience. And so that’s sort of how we do it, is we just wait, we just sort of try to figure out, okay these are like sort of the top concerns, and these are the problems that creators have sort of hacked. That’s I think really measurable.

Is if you use like, oh wow like every single person that sells a movie sells like in the download list has like the top HD version, but they also have like the 360 P version and then they have like the really small version, mobile friendly version, and it’s like wow a bunch of people are doing that we should automate it. Like just upload the highest quality and we’ll do for you.

Andrew: I see, and the reason I’m spending so much time on this, is because we do have blind spots, frankly me included too with the problems that our customers have. But if we start eliminating all the problems that they have one at a time for most important, to least important. We keep giving them a better and better experience and keep drawing them back in.

And so that’s how you do it. That’s your process. You even told me I think last time that there’s a spreadsheet where you will keep track of the issue that people come in. How does that work?

Sahil: Yeah, so we basically we have our Google Doc, a Google Sheet that sort of contains sort of a unique sort of distinct, sort of request we call it, we call it a feature request doc. And so say someone says, hey I really want, I don’t know, like an Android app for example we are working on one it’s not live. We have an Android app thing right, and then we basically every time someone emails about the same thing we increment the number next to from one, to two, to three to four.

And then if there’s a unique feedback associated with it, like oh this guy has a really good idea on how to do like consumption because Android has this special hook that you can use that iPhone doesn’t. We’ll note it, in on the right, so you’ll have the notice to deal with the feature request.

And then when on a weekly or monthly basis I’ll be like okay I think like it’s going to be really important for us to focus on these things. I’ll look at it and I’ll sort of inform me like okay these are probably areas that we should think about more heavily. Like people are starting to use Gumroad to sell sort are tutorials and like it’s not a great experience for that. And the cool thing is like they hack Gumroad to do it and like that’s awesome because it mean if we do it properly hopefully it’s going to be a much better experience.

Andrew: Do you have an example of something that came from a complaint or a frustration, or a pain that one of your customers had that you didn’t know about, but once you fixed it the business grew?

Sahil: I would say the film streaming one was a really good example.

Andrew: What is the film streaming one?

Sahil: Yeah, so when you sort of before the right Gumroad work is, you’d upload the MP4 for example and when you bought it, it would just take you to the MP4. And on most modern browser you know assume we’ll know it’s a movie because of the [??] and some of the data, the headers and stuff. And then you’ll be able to watch it. Like so far he has this name player in Safari.

And so like I never thought of that as an issue. But then people didn’t know that, like some browsers don’t do that and like if you’re on your phone it does some weird and different and there’s no way to save it. And there’s all these issues.

And so we got a bunch of feedback from film makers being like, hey I really want to use Gumroad but you know if you use Netflix, if you use Netflix, you go on Netflix you’re in the thing and it just start playing and you never have to think about what’s happened. You just hit play and it plays. You know if you’re on a bad connection it will still play it will just be lower quality and then once you’re on a good connection it will go up. And if you start playing it on the computer you go somewhere else and play it, it will work just perfectly it’s great. You never think right it’s a sort of brainless experience. It’s great.

Andrew: But on Gumroad it used to be you downloaded on some browser, other browser it just plays within the browser if you want to save it for later. You don’t know how to do it, it won’t remember your place etcetera.

Sahil: Yeah, you know if you’re a creator and you upload a weird format that you know, just like you might upload a 3DP or something, you know very well and then a person downloads it and is like I double click it, and it opens in terminal like I don’t know what’ happening. Then that’s not great, that’s not a good experience.

Andrew: So you’re getting complaints from creators saying, we need an easier way for our customers to view the videos that were selling through Gumroad

Sahil: Exactly and [??] have to think what the type of file that creator most costumers are going to watch. It’s not the end of the day, depends upon consumers what they are looking for. And Ideally I think it’s like a little like there is a bunch of imports going in to Gumroad and there is a bunch of output going to each consumer. And so creator might upload a weird thing. We will take it take turn it in to a thing and then we know this person wants this file we will send them back the version of the file. So, basically the content is the same. I think we never changed the video, it’s the same video. But It’s the container format has changed sort of be right for that consumer. And I think that’s an incredibly powerful

Andrew: How do you think that it worked out? How do you know that helps your business grow? And that it helped a handful of loud consumers and now they are not talking anymore.

Sahil: [laughs] Yeah, they are still talking, don’t worry.

Andrew: [laughs] Right.

Sahil: I think we saw numbers grow up. We saw support drop. And a lot of it honestly I think especially at an early stage company, relatively early stage company, its anecdotal, you know. We talk to our viewer all the time that we anecdotally notice something start happening. We don’t really need like we are not super like we are only going to work on things that have hundred feature plus. At the end of the day like that really like you know like volume doesn’t necessarily mean its [??] or not.

So I think it’s sort of our job sort of fast the horse thing. It’s our job to take the feedback and turn it in to a solution that we think is going to work everybody right. And so you know we might have gone like hey, I bought a book but I wasn’t able to view that thing. Or hey, I have got a weird movie and I wasn’t able to do it. I got a weird audio file and it sounded weird or it is like three minute long MP, AICC and it was like 600 MB. That doesn’t make any sense. And if you just compress it ahead of time, it would be 4MB.

And so things like that we should just do. You know we can a lot of these things that are [??] we can compress that. We should do more and more and more of that over time. At the end of the idea, if we solve the problem, no one notices it. Like no one says, oh my god that file was so small. No one. That’s great. We don’t want people to think about that stuff. That’s not we are trying to do.

Andrew: You know what, when I first come in to conversation I kept looking for everything to be so data driven. It’s not. In fact the first time we recorded and it didn’t exactly come out. You said to me Andrew, sometime we just work on what we think is the most fun that if we think it’s meaningful for us to build it then we might be willing to spend some time on that. How do you know that doesn’t get too out of control that you are not just spending time on fun cool designs?

Sahil: Yeah, it’s hard honestly in order to. I think one it’s a little easier to get away with, because we are a small company. We are all in one room. Right and so I think that I get excited personally when I know I am going to build something that’s going to impact a lot of people, right. If I had the choice between [??] that’s going to help 1000 people or six p [people. I am going to choose a 1000, if it’s the same, everything else being equal. And so I think that’s how most people approach it. You were to govern because you want to have a meaningful impact on a bunch of people. You don’t want to work something small feature of Facebook or whatever you have right. And that’s what have been spelled here and the ideas are being [??].

I think in general people already have that bias. I am sure you want to work on a combination of what’s exciting and fun and impactful. And I think in general if you let people sort of make their own calls they are going to lean towards that anyway. We haven’t had a big issue like I am just working on this because it’s really fun. Because if that’s true, like you wouldn’t work at Gumroad. You would work at a place where you had more freedom and flexibility to just work on things. At the end of the day every single person at Gumroad what they decide to work on is going to change the future of the company because everyone is a big part of it. And so like you know it’s sort of self.

Andrew: Do you have a metric that you keep around the office so that everyone can see how many new sellers you have, how many new customers, how much revenue , is there something like that that you are all gearing towards improving.

Sahil: Yes, we do have a number on our dashboard internally in the office which is how much volume we have processed from the creators in the last 24 hours minus refunds and charges and things like that

Andrew: And that’s the number you are all working towards improving.

Sahil: Exactly like that’s right now that’s the number one, there is actually two metrics one is a little harder to track. But I can talk about that too. Yes, it’s how do we increase that number? A lot of it is not how do we increase that number because at the end of the day the only way to really directly increase the number is to like go on to Gumroad and buy stocks. And so it’s more like this is over time it should grow and it’s going to grow [??] for the product that’s very useful for a lot of people. And but it should at the end of the day there should be .

Andrew: Fair to say that holds you in check so that if you all start going towards just creative things that don’t increase that number, that number will give you that feedback, hey we’ve been stagnant for a few weeks or we’ve been going down for a few weeks.

Sahil: Yeah. That’s, yeah, exactly.

Andrew: What’s the other metric?

Sahil: The other metric is how many, and this is a very, it’s a long-term metric, it’s how many creators are making their livings through Gumroad.

Andrew: I see. I see [feedback]. And that’s not an easy one to go into the dashboard and see, but you . . .

Sahil: Yeah . . .

Andrew: . . . can tell.

Sahil: . . . it’s probably because that number, one it’s, they’re just inherently are going to be smaller, because to make a living on Gumroad, you’re making a significant amount of money, right?, which is, and we’re relatively young. And it’s, it’s not a, it’s quite a nice number, but yeah, and we also know it’s harder to sort of say it’s, it’s, it’s a very consistent number. It never goes down, right? The people that are, basically, if you’re making a living on Gumroad, you’re never going to leave.

Andrew: How do you get that number?

Sahil: So what we do, is we just, we do just very basic, if you’re making three to five, depending on where you are, $5,000, let’s say $5,000 a month on Gumroad. Assume . . .

Andrew: Then you assume this isn’t a living. Gotcha.

Sahil: Sorry.

Andrew: Alright. I, I’ve been clicking on something on your site that I have to bring up in the, in the interview. I want to talk about this guy Alex, who works at the company, and I want to know how you got more sellers. But first I have to live up to an obligation to a sponsor. And Sahil, pay attention to how I do this promotion. Your guy who sells subtly but clearly, tell me how I’m doing as I, as I try to get to be a better salesperson in this interview.

“So I’ll tell you the problem that I’m trying to solve. A lot of us have people come to our sites, and the first time they hit the site, they don’t find what they like and they say, “You know what? Alright, this is not for me. It’s a great site.”, and they move on and forgot about the site completely. Or, especially if you’re a blogger, you have people who come to the site, they see the latest post and they say, “This doesn’t speak to me. I’m gone.” I know, certainly for me at Mixergy, some people use to come in and say, “Oh, he’s only interviewing funded entrepreneurs. This isn’t for me. I’m gone, because I’m a boot strapper.”

So what we’ve decided to do at Mixergy is, say, the first thing they see when people come to our site, tell them what the site is about, it’s about interviews and courses taught by proven entrepreneurs. And if they’re interested, they need to register by just giving an email address. And once they hit submit, they get to see the site. That way, if the first thing they see isn’t great, we have another opportunity to introduce to what else is coming. It’s was this little, s-, little idea that my friend Noah Kagan gave me once, as we were walking, and I told him I had this problem. I put it up on the site.

It’s been the best thing to, to happen to Mixergy, and helped us grow, and grow, and grow, to know what, seventy-five, eighty thousand people on the mailing list, who are all interesting in what we’re creating. Well that page has done incredibly well at converting, and so I want to make it available to some people in our audience who have the same issue that we had and want to try to increase their, their conversions, increase their stickiness, by inviting people come to their site, to give their email addresses and join the mailing list. So if you’re that person, you can just go to and get it, and get it.

And don’t worry if you don’t have a site fully developed, or you’re not a coder yourself, it’s all powered by a, a company called that knows exactly how to make sure that this stuff stays powered, connects to whatever system you use, [??, Weber, Infusionsoft, Soft, whatever. And then it just will work because it’s their job, that’s what they do. So if you’re interested in this, go to” Sahil, what do you think?

Sahil: That was good. That was solid. I do like, I do the same thing, where, like, before I pitch a solution, I say what the problem is. It’s super important to say. This is . . .

Andrew: That was the new [??] direction I’ve been going in.

Sahil: Yeah.

Andrew: So what would you pitch and say the problem, problem, offer your solution and say what worked out great?

Sahil: For your product?

Andrew: No, for yourself, or actually, even for mine. How do you, how would you use this?

Sahil: Yeah, normally I’d say, everyday people go to my website, and a lot of people find things that they log and that they’re excited about, and then they, they go through the work manually of clicking my little twitter link, and then going, following me, and that’s sort of a way for them to keep connected with me. But a lot of the time, especially people are finding my content all, through different ways, it’s not like they have any context on who I am or whatever. They might see a post that I wrote about something, and they’re like, “Oh, I don’t like this.”, like I, I ,and they don’t know, they don’t even know that I was, my past background, or if I’m an engineer, designer, or what.

Andrew: …this box comes from the top, drops down and just centers itself. If I hit the X, this box goes down the screen. It doesn’t just pop up, it doesn’t disappear, it goes down the screen, it has like this gravity. If I click the button again, the box that allows me to register comes right back from the bottom of the screen to the center because the first time I clicked X is dropped to the bottom. That little bit of flourish, that little bit of design gets me so engaged with a button that I otherwise would ignore. You have other examples of how you’ve done that, right? This is a part of your culture. How else have you done it?

Sahil: Yeah, I think in general, well in that case, it just made sense. One, in real life things don’t just fade in and out, right? That would be weird. Things come in and out and leave and stuff so yeah, I always try to approach things with what’s the physical version of this. And in that case, it comes down from the top and when you hit dismiss it sort of falls like it would in real life if you dropped something. It would be like [sound effect]. It would be sort of like meh.

Andrew: Yeah, a little bit of an angle as it comes down.

Sahil: Exactly, and then when you drop it and it comes down, it doesn’t go like this and then fall again, right? It comes back up. So yeah, we just try to think about how, in general models they’re not real, right? It’s not perfect, but I want a little bit of this is the realistic, this is like if you had to guess at what would happen, what would happen. And we try to do this all over the place. With the credit card form we talked a little bit about you go to the credit card number field and then you go to the C.V. code, the little card icon in the corner will flip, but only, it’ll flip in all cases except if we know because of the card number you typed it’s AmEx because on AmEx cards they’re on the same side.

Andrew: It’s on the same side so the card icon will not flip over. That little bit of thought, so I’m curious about, I know how you do it because it’s part of who you are and you’ve had a lot of experience doing it and this is your sensibility that’s now being magnified by all the people at the company and the growth of the business. What I was curious about is how do you do that? How do you hire someone who can carry that forward? And it’s not like you sit down and you say, and this is what I thought at first, you say, “All right, we just designed something that’s functional. Now let’s think about how we can make it more whimsical and more interesting.” You said that’s not how it works. It starts with how you hire people. And I thought we can talk about Alex, a guy who works at your company. What does Alex do there?

Sahil: Alex is a product designer, well he does everything, but he’s primarily a designer at Gumroad.

Andrew: Okay, and what’s Alex’s last name?

Sahil: Alex Hertz.

Andrew: Alex Hertz so when you were hiring Alex Hertz you said that’s one of the things that you were looking for. So how did you find it?

Sahil: So I found him, how did I find him? Probably on Gerbil or something like that I saw some of his work. He might have signed up to Gumroad. I’m not sure. But he was a musician, designer living in New Orleans, and I just liked his work. I thought it was interesting so I sent him an email asking if he’d ever thought about moving to San Francisco and if he just wanted to chat about what it was like. There’s a migration of a lot of people moving to San Francisco so if you have any questions, I’d love to talk to you about Gumroad, or not, it doesn’t really matter. I would just love to give you more information. So he was kind enough to accept, we talked on the phone for maybe like an hour about San Francisco and design and how this world works and is, and he was excited enough to take our design challenge which is basically like pick a feature that doesn’t exist or does exist but you don’t think is perfect on Gumroad which is probably most features and then design a solution, right? And it’s really open ended.

It’s not like this is a wire frame, make it visually completed. It’s just like, for example with Alex, it’s like, hey, we really want an invoice feature. A lot of people have been getting, and I try to frame the problem as broadly as possible and I don’t say this is a metric we’re trying to improve, as I mentioned we’re not super data driven, it’s more like this is a general problem that we need to solve. And in that case it was creators are doing support to sort of send these invoices out to buyers, especially buyers in Europe that needed a more formalized invoice than our really simple receipt, they need a way to get this thing.

So they’d email the seller or the creator and the creator would be like, okay cool, I’ll go make an invoice with your information. Hey, to do this I need your business address or I need a full name or I need whatever. And then they’d email them back the pdf. So how do we make this simple, right? Ideally it’s really simple, really easy, you sort of do get a sense of using Gumroad. That’s what we aim for.

Andrew: And you gave them a specific task, and you do this, I guess, as part of your hiring process — everyone gets one task that they could, or one aspect of the site that they could either invent or reinvent. You always pick it for them?

Sahil: No. I give them an option. I actually — I suggest two or three different ones. And then I’m like, “But if there’s anything else that you’re more excited about, you can go pursue that,” right? So if you think, “Oh, I really think it’d be cool,” — because a lot of people walk toward Gumroad because they believe in a certain vertical in Works or in Help [?? – after the word people]. Like filmmakers, for example. Or comics, right, you might get excited personally about that. Or video games. So you might say, okay, I really think rentals would be really cool. Right now I could just buy a product in Gumroad, and download it, and that’s it, but if there as a way to do film rentals, for example, you know, on iTunes and Vimeo and things you can do that, that might be really cool, right? And so, I always say, “These are recommended, but feel free to do, if you’re more excited about something”-

Andrew: So you told Alex a couple of suggestions, and then a third suggestion, which was create an invoice process for us, and you explained why you need an invoice process, and then what did he do with it?

Sahil: Yeah, so he killed it, to be honest. It was great. He sort of showed a little bit of his work, I think it’s always nice when — I don’t ask for it, I actually just ask for the solution, but I think people will try and show their work, they’ll be like, “These are some ideas I tried and didn’t work, and then this is how I got to the solution.”

Andrew: You do want to see their solution, but not necessarily all the approaches that they took. Right?

Sahil: Exactly.

Andrew: Okay.

Sahil: And I’ll try to encourage people to be as high fidelity as possible, right? So wire frames are nice, but I always like seeing the visual, done thing. Because I just think, to me, that they’re the same. It’s really hard to build a product in wire frames and know that it’s going to work and be functional, because I haven’t seen the visual design for it, and vice versa, those things to me are so…it’s like designing a building without knowing the engineering behind it or something.

Andrew: All right. Okay, so you’re then asking them to create a feature for you that you could end up integrating into Gumroad — that’s a lot to ask for someone! You’re basically saying, “Work for us for free, and we like it, then we’ll hire you; if we don’t, then so long.”

Sahil: Yes, basically. That’s exactly what we do.

Andrew: All right, and so what was it about his finished design that made you say, “Yeah, this works for me, I like it”?

Sahil: Yeah, I mean, I think he approached it really well. He very quickly was like, “I don’t want to-“…the goal, the perfect solution, will mean no time on the creator side, right? Because that’s just a fundamental thing that we believe in, that if we can save the creator time, we should.

Andrew: Okay.

Sahil: So I think he got that immediately, it was like, okay, we’re just going to put it on the buyers, how do we do this, right? And so — Gumroad is such a simple service, there’s really only two places that you could make this functionality live that would make sense, right? One would be on the web receipt, so you buy a product, it’s like, “Generate invoice right away,” and then one is on the email receipt. The email receipt is the little sort of receipt thing that you get that has share buttons and the download link and the price, and it sort of acts as your, you know, receipt.

So, I think he understood very quickly, and he actually showed me a couple approaches that were a little different…Well, you don’t really need a receipt right away, it’s more like, “Oh, I bought this thing, and I’m filing this, and I need the receipt now.” And the web is very sacred, because it’s all synchronous, it’s part of the same experience, but an email you could get, and then look at, ten hours later — it’s not a big deal. And so he went with the solution where the receipt on Beam A Receipt [SP] would contain a button, a generate invoice button, you click it, and then that button is linked to that purchase, and so if you’ve already given us some information, it’s already auto-completed, and then you just have to fill in the rest, and then you hit “generate invoice,” and we’ll just…we already have your email, because we-

Andrew: What else do you need to fill in, if you already have all that information?

Sahil: Potentially, if we have all that information, nothing. If we have all that information, they could just be like-

Andrew: Is there something that’s usually left out that you need to create an invoice?

Sahil: Mailing address, business address, yeah. Those are the two.

Andrew: I see, okay. And what you liked about him was that he shared your philosophy of: take away as many steps as possible, automate what you need, and only make it visible where it’s necessary. And he figured out that you don’t just send an invoice to everybody, because some people don’t want it, you do send a receipt to everyone because almost everyone wants it, and so, let’s put the button on the receipt, and when people click it, the invoice is as created as possible and asks for as little…I see, and that’s how you understand that he has the philosophy that you have. Do you also look in there for any of these flourishes that we talk about, like-

Sahil: Yeah. Yeah, for example, in his thing, I’m pretty sure, as part of that when you are sort of filling in information there is like a little in just HTML like a little page under those form and as you type your information it would fill in the form.

Andrew: I see .You get to see what it looks like while you are typing it in, what the finished product looks like

Sahil: Exactly and then when you extend I think it sort of I think may be like that little paper that slides. It’s like we are sending literally that thing created to you. And so.

Andrew: Are you still in touch with what your design philosophy is that you know it when you see it and you know why you know it’s right or it’s just a feeling that this guy somehow thinks like me.

Sahil: No I think it’s not just a feeling I think. I don’t have it strictly written down. But yeah there is a value, I think I created a cultural value at a company, you have these sort of almost like laws right simpler easier smoother faster more intuitive. And I think there is a little bit like I think pretty quickly you can be that good a designer. That’s not. You know I have this thing, my designs are pretty functional like they are very like pixel [??], you can do a lot with little and that’s like it’s like hit as many as birds with one stone as possible sort of thing. And I think Alex will use the same thing. You know, if you don’t need a thing, we should kill it, right.

There is this principle in Engineering called dry ( Do not repeat Result), which is if you have two blocks of code that are like 10 lines are look identical except one number is change, like ideally you can abstract that, right. You can sort of put in one place and then reference that with a different number. And so, put it somewhere else and reference the thing. And so I really believe in that design. For Example, if you have a primary button that primary button should have that code that style defined in one place and everything should reference it. It’s a very common Engineering principle less so in design because it’s new one, a new sort of thing that’s being applied to it.

And he felt that and he really believes in like okay, there are already places in that app where we asked for someone’s address and someone’s name when you buy a product, especially if the user is asking for that already, we should use the same UI. We shouldn’t reinvent the wheel. We shouldn’t have a slightly different address one. And so I think that consistency is really important to us and I think he embodies that pretty well.

Andrew: You know I was curious about how you did it. Because I do see it everywhere. In fact a friend of mine John Crocker when he said he went to a book event with Chris Gillabough [SP] that you guys just hosted. And he said this one is so beautiful. They made it feel like an old fashioned salon. They made it feel like, what was the design of that event?

Sahil: Honestly like I just [??] your credit for that. That was all.

Andrew: I know that’s why I am curious. Because it’s easier if it’s all you designing and it’s a lot harder if it’s you designing a company that designs it.

Sahil: Yeah. I think a lot of it is just you know trust like saying yeah Hai Ashiq [SP] I call it jokingly delegation by [??] which is like I am busy I am lazy, you do it. I am not going to do it.

Andrew: But you can hand it off to some people and their stiff just stinks on and you have to accept that because you handed it off or you can hand it off to people who can do better than you would and carry through your philosophy. Am I right to say, Sahil, that the reason that came about and the reason that other features that come about is because of the way you hire or am I missing something that’s it.

Sahil: I think you are right. I think it’s a combination of hiring the people and giving them the right kind of feedback.

Andrew: So How do you give feedback that allows you to communicate your philosophy on design to people?

Sahil: one, there is a couple of things I have learnt. One is ask a lot of questions. Right. So don’t and this is something that I am sure I still do I am try to get better at. I think the first time you give a negative feedback like yeah, you should have done this. You should have, that was bad this was good, right. That’s not good. No one likes to be told that they are wrong.

First of all you need to stop doing that. Second one, typically you have a different set of data. The reason they made this decision and the reason you made the different decision because you have two different sets of data. Right like, so it’s like I think there is a term like check the inconsistencies or something like that. Figure out what that is. Figure out what you disagree on that led to a different decision. Don’t disagree on the decision because that’s useless. You are not going to learn anything. But then you thought that 600 people are going to show up and I thought 50 people are going to show up. And so I invested less and you invested more. [??] That’s a made up example. But, it really about why not the what

Andrew: So if you said to someone you know we should do is we believe in content creators we believe in education, we are going to have some kind of event some kind of series and someone puts it together and you go and say this is just not a pleasant experience. It’s really uncomfortable and it looks too cheaply thrown together. How would you say that? Instead of saying, “Hey this look really cheap, it misrepresents our brand.” Using the philosophy you just articulated.

Sahil: I would say, “Was there a reason that you decided to not invest a lot of money in the atmosphere of the place?”. Because there are conflicting values. We might have a value that, just as we shouldn’t design things if they don’t need to exist, we shouldn’t spend money if they’re not actually going to add value. So, it’s like, “Oh, I thought you wanted me to be super frugal, so I didn’t put any effort into it.” It wasn’t effort, it was just that I didn’t want to spend any money.

That’s why I don’t like to say, “You shouldn’t have done this.” Because I don’t know the reason. This idea of behavior versus intention. I love this idea, and I think it’s one of the most valuable things I’ve ever learned. It’s the difference between behavior and intention. When you judge yourself based on what you’ve done, you’re judging yourself based on your intention. You don’t say, “I crashed the car. I’m an idiot.” It’s more like, “I didn’t mean to crash the car.” No one really means it. Versus when you judge somebody else, you’re judging them because you don’t know their intention. You can guess. But, you’re judging them based on their behavior. For example, I wake up late, and I need to catch a flight to New York. So, instead of taking the BART, I take an Uber. I know exactly why I did that. But for some reason, if I see someone else I think, “Hey, this person took an Uber for no reason.” I have no idea, but immediately I think, “They took an Uber. They shouldn’t have done that. They should have taken the BART.”

Andrew: I see. Until you understand the intention, you can’t pass judgment on the action.

Sahil: So just ask why. Be like, “Hey, why did you do this?”. “I did this because…” “Oh, I didn’t know that, that’s awesome.”

Andrew: [??]

Sahil: Then I think, “Oh, if that’s why, then maybe this is a better way to do that.” Maybe you can get the same value without the same amount of effort. I think that just helps a lot. If it’s a really thrown-together event, I think that would probably be a bad hire. Honestly, we shouldn’t get that far. Luckily that hasn’t happened [??]. As you said, the even was amazing, and really well put together. People care too much. The cool thing with Gumroad is that everyone is an ambassador to Gumroad. If you’d rather be there with an engineer, and you’re talking about work that you do, you’re 5% at least of the company. You’re a huge advocate for the company. In general, you want to do a good job, even though it might make you sleep 4 hours tonight. People are judging you based on what you and your company are producing.

Andrew: I don’t think I’d ever directly say it to anyone. But often when you have coffee with someone or drink with someone, you don’t say, “I had drinks with Steve Blank.” You’d say, “I had drinks with the guy from Gumroad.” Maybe that’s part of our culture here.

I want to ask you two more questions, and I know we’re close to the end here. The creators are the ones who really help you grow and get the end customers who bring the revenue that allows you to take care of the creators. So what’s your best way of getting sellers?

Sahil: Honestly, the best way is to help build an awesome, I mean everyone says it…

Andrew: But they don’t know about it. How about promoting it to them so that they know about it? Going back to where we started at the beginning of this conversation, where you didn’t just create good things, you knew how to tell people about it. What’s your best way of telling people about it?

Sahil: Honestly, we’re still trying to work it out. I think we have a good product. Part of Gumroad is sharing it with your audience. So we have Nathan [SP] Berry will sign up to Gumroad, and he’ll let his entire audience know that he now uses Gumroad. A lot of our new users come from him and other similar creators. There is a sort of network effect. Like if 5 of your friends in this community of comic writers or comedians, and all of you start using Gumroad, it’s interesting and you pay attention. There industries we work with are a lot smaller that you would think. People talk a lot. Launching a big new album, what do you do first? Are you saying, “Hey, I saw that you did this thing? Was it good, or not?”.

Andrew: You know what I’d like more of? I get how that’s true, that when Nathan uses it, other people know that he’s using Gumroad. If he trusts Gumroad, then we will, too. But, I’d like to see you talk in public more about your design and creative process that I want to know how Gumroad gets to where it is, kind of like you used to do when you were starting out. I think you have something here in the way you create that would allow you to do for your design philosophy what Jason Fried did with his, which is teach others and allow them to follow in your footsteps. And frankly, for you, it’s more important than Jason Fried because all your people are designers who are hungry for this stuff. I’d love to create a PDF that has your feel to it. I’d love to know how to do that to that level, especially if I’m selling it on Gumroad. Does that make sense?

Sahil: That’s really good feedback. I will take it and think about it.

Andrew: All right. Give it some thought. Maybe other people will now chime in and say the same thing. I’m looking at your blog, and your blog is good, but maybe that’s a place where you can do more of your, I hate the phrase, but thought leadership. Actually, it’s more like teach us your process. All right.

Sahil: Yeah.

Andrew: Before I ask you a last question, anyone who’s heard this interview and has gotten this far has got to go and watch our first interview. And to do that, all you have to do is just type in five letters into the search box on Mixergy, which is just S-A-H-I-L. That search box just keeps improving, and I’m urging you to try it, especially with this interview. Sahil, just type it in and you’ll see our first interview. It’s fantastic. Dude, the way that you were thinking back when you were in college. I remember emailing Mark Suster and saying, “You got to get with this guy. You’re in L.A. He’s still in L.A. Talk to him before he leaves L.A. because he’s the kind of mind that we need or L.A. needs. And unfortunately, L.A. lost you. San Francisco’s just too much of a fricking draw. All right.

Here’s the final thing. You told you more in private about where your revenues were, but you said, “Andrew, I do not want to obsess about the revenues. I know you’re going to ask, but I don’t want to obsess it.” So we asked you in the pre-interview what do you want to talk about, and you said, “We prefer stories.” So there was one story that you mentioned that I think we should close with, which is the story of Kyle Webster. Why is he indicative of what can be done on Gumroad and how big Gumroad is?

Sahil: Yeah, I think he’s a great example for a few reasons. One, I think it was scary for him to go out and do this. He had these brushes for Photoshop that he already.

Andrew: These are software tool brushes or software tool that you incorporate into Photoshop, but you have to grab them from someone, and he was making them.

Sahil: So he made them I think just for himself, and then he was like, “Oh, I could put this out there,” so he did. And he made $2,500-$3,000. If you go to, you can download a case study that’s really dense and detailed around his entire story. I’m not doing it to promote Gumroad, I really think it’s so interesting and people could learn a lot from it. He did this and then he kept doing it. His audience slowly grew, and his audience have their own audiences, so they sort of shared it.

Now he’s made over $200,000 just selling these things that if you asked me two years ago, I’d be like, “No, that’s crazy. That’s insane.” He makes more than some famous published authors do or some famous published musicians do just selling Photoshop brushes. I think it’s a good example, one, because it’s not easy. It shows that he had to go out and do something different and new, and that’s scary. Hopefully, we made it easier for him, but we didn’t totally trivialize. Two, I think it just shows why Gumroad is interesting. We’re not building a marketplace. We’re not building a thing for musicians or filmmakers. We’re building a thing for creators. And by this sort of blanket approach, I think it’s hard. It requires a lot of time and effort for us, but it means that we can build a thing that might work for musicians, might work for filmmakers, but it also works for Kyle Webster. No one would build a marketplace or a tool for Photoshop brushes. It would just never make sense.

And I think that’s just a really cool part of Gumroad. And then I think the other really cool thing about Gumroad and his story is that so many Gumroad creators have bought his brushes. We’re not a marketplace, we don’t connect people with each other, but it happens organically because designers follow each other on Twitter and Dribbble and all these services. I’m a designer. I buy his brushes so I can use them. We actually, coming up, have a post on the Gumroad blog which will talk about the Gumraod products that we’ve used internally to build Gumroad, which is going to be pretty fun I think.

Andrew: Yeah, that’s the kind of stuff I want to see.

Sahil: Yeah. And he did it because he loved doing it. He wasn’t like, “Okay, I’m going to wake up and make 200 grand, and this is how I’m going to do it.” He had these brushes he had already made, and I just think it’s really cool. There’s this trend of turning from a service provider to a product maker and creator. You detach an hourly rate from how much you make. It’s not about, oh, I need to work 10 hour this week so I can make a thousand bucks or whatever. It’s separating yourself from that. Just like what I did with selling apps back when we did the first interview and before that, I just wanted to make something. Then I was like, “Oh, I could also make money doing this.” And that was really cool.

Andrew: I got the case study. It’s another example of how you guys could have just given me a case study that looked like a Word doc, but it looks great. I like how you explain why things worked for him like bundles. Bundles worked for him. Apparently, his mega pack bundle produced about half the revenue of all the other stuff, and bundles in general produced more than 50%.

So by taking all his different brushes and instead of selling them individually, creating packages where people can buy multiple brushes, he increased. But it’s all beautifully done. All right. I’ll just tell people that’s where my mind was. I know sometimes people will see me look all over the screen. It’s usually because I’m checking stats to make sure everything is what it is, what we hear in the interview. In this case, I was just going to, and as soon as I entered my email, I didn’t even have to go to my inbox, you just gave it to me. All right.

Thank you so much for doing this interview now a second time. We have a crisp, clean time. Thank you for going into the office to record. And congratulations, dude. I’m telling you I remember before even Data, when I think we were talking via email, and of course I’d see you online, and I’d watch your progress. I when I hear people talk over and over about Gumroad and use it as an example, I go, “I know that guy.” It’s amazing to see how far you’ve come. Congratulations.

Sahil: Awesome. Thank you so much. Thanks for having me.

Andrew: You bet, and thank you all for being a part of it. Bye, everyone.

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