How did a 23-year-old manage more than $400K in revenue with his self-published books?

In this interview we’re going to find out how an entrepreneur with a habit of not finishing things actually ended up writing and finishing a book.

And more importantly, how did he turn that book into a real business that produces hundreds of thousands of dollars?

Nathan Barry is the designer and entrepreneur whose latest company is ConvertKit, which offers software that allows you to create landing pages that capture leads and it sends out automated emails. He is also the author of Designing Web Applications, Authority, and The App Design Handbook.

Nathan Barry

Nathan Barry


Nathan Barry is the designer and entrepreneur whose latest company is ConvertKit, which offers software that allows you to create landing pages that capture leads and it sends out automated emails. He is also the author of Designing Web Applications, Authority, and The App Design Handbook.



Full Interview Transcript

Hey there, Freedom Fighters. My name is Andrew Warner. I am the founder of, home of the ambitious upstart and the owner of a new shock mount. I’m actually trying out the shock mount today. We’ll see how it works.

In this interview we’re going to find out how an entrepreneur with a habit of not finishing things, how that entrepreneur actually ended up writing and finishing a book. And more importantly, for the focus of our work here at Mixergy, how’d he turn that book into a real business that produces hundreds of thousands of dollars?

Nathan Barry is that entrepreneur. He is the designer and entrepreneur whose latest company is Convert Kit, which offers software that allows you to create landing pages that capture leads and it sends out automated emails. He is also the author of Designing Web Applications, Authority, and The App Design Handbook. And why don’t we just jump right into the interview, Nathan. Good to see you.

Nathan: Yeah, thanks for having me on.

Andrew: Nathan, as a developer, do you ever feel like a fraud? As a designer do you ever feel like a fraud and say to yourself, hey, if I was so good at this stuff, I’d be creating my own software? If I’m not, then I’m selling books and becoming a marketer.

Nathan: Yeah, so first of all, I definitely feel like a fraud on other fronts. Maybe not on this…

Andrew: Okay.

Nathan: …but imposter syndrome is definitely present in just about everything I do.

Andrew: Okay.

Nathan: But I think the phrase is something like, those who can do and those who can’t teach.

Andrew: Yep.

Nathan: And I’m a teacher and so I think the implication in the question is, you know, OK, so what, you know, why aren’t you building more software? And I started out building a lot of products and I, there was a key realization that I had in there when I couldn’t get anybody to buy them. I couldn’t get anybody to pay attention to them. And short of buying advertising, which at the time I thought was way too expensive and out of my budget and all that, I just didn’t know how to get customers or to get anybody to care at all. And it wasn’t until I realized that, if you teach people, then their interested. And so at that point, I realized that to be good at marketing, I have to teach. It’s not just a function of, you know, helping people learn or something like that. It’s a method of getting attention and it’s a method of getting customers.

Andrew: I see.

Nathan: So if I want people to buy email marketing software, right – you know, we compete with Mail Chimp and AWeber and companies like that – then I’ve got to teach you how to do email marketing. The more I teach you that, the more you trust me and then after a while you go, you know what? Nathan’s philosophy at email marketing makes a lot of sense. Maybe I should check out his software. If I wasn’t teaching, I wouldn’t have any customers.

Andrew: I see. So you’re saying teaching online through blog posts helps you bring in an audience without paying a lot of money for it and allows you to then transfer that audience into your business and turn them into customers. I get that. What about the books? Why the books? I mean, the reason I ask you is this. I know that, I know the objection that some people who are listening to us are going to have, which is to say, hey this isn’t, this is a site where Andrew interviews successful entrepreneurs about how they built their businesses. What is this guy doing being an author, marketer? Is he just selling info products online? And I thought, we just handle it and handle it by acknowledging that at times you feel that way, that you’re concerned about that. Aren’t you?

Nathan: Yeah, and I definitely feel like, it’s kind of interesting. I feel like the training side of the business isn’t as substantial in some ways, even though it makes far more revenue. And I don’t know why that is. It feels a bit more temporary, even though the, you know, training side of the business makes a quarter million a year. And so I think it’s just the atmosphere that we’re in, kind of, or the environment. Everyone wants to build software and I’m definitely going that way too. But training and books and all of that are a fantastic way to build an audience. I wouldn’t be able to build software if I didn’t have a steady cash flow coming in from training products. And they’re also a fantastic way to learn all these lessons about marketing and business and sales. Because if you jump in and the first product you try to sell is a SaaS app that, say, you spent $50- to $100,000 to develop…

Andrew: Yep.

Nathan: …and that’s your first sales attempt, you’re screwed. Like, there are so many lessons that you have not learned about how to sell products online that you (inaudible)…

Andrew: For example?

Nathan: Let’s see. What would be a good one? I mean, look, just getting leads in in the first place. Teaching or content marketing, all of that. Things on conversion rates. You know, what’s going to make a landing page perform well. All these…

Andrew: I see so you need to learn all of that on smaller products before you build something that’s worth a hundred bucks a month and start right there.

Nathan: Well, and I think it’s not the hundred bucks a month that you’re charging, it’s how much the software products cost to develop in the first place.

Andrew: Yes.

Nathan: And so development is expensive. And so if you can’t build it yourself you need to put out all this money and then you’re going to find that you don’t have the skills to sell it. And so my thinking is start with the small products. Start with something like an iPhone app, like an e-book, something like that. Learn all those skills, like Jason Fried talks about how making money is a skill. His examples are like playing the piano and . . .

Andrew: Or drumming. I remember his blog post.

Nathan: Yeah.

Andrew: It was an article in Ink Magazine, actually.

Nathan: Yeah, that’s right. And so he talks about something that you need to practice. And following that example, I would see like selling a SaaS app that cost hundreds of thousands of dollars to develop. I would see that as like the huge concert in front of thousands and thousands of people, and you’re not going to start your drumming career there. You’re going to start it with practice and be like tell your buddy, “Hey, check this out.”

Andrew: Gotcha. Play the local coffee shop before going to Madison Square Garden.

Nathan: Yeah.

Andrew: All right. So let’s get into how you built this. We’ll compare a local coffee shop how you built it into a business actually producing hundreds of thousands of dollars where you sell these e-books. And figure out how the software part of your life fits into all of this. Why don’t we go back to the thing that I said at the top of the interview? You feel like a guy who had a habit of breaking habits. When it came to writing, how did that play itself out?

Nathan: Yeah, so excellent point. I realized that the people I admired online, the thing that was different between them and me wasn’t skill level or anything like that. It was the fact that they were teaching, they were writing, they were sharing, and I was keeping it all to myself. So I was like, okay, I want to start a blog, and I get a few blog posts out and nothing would happen.

I always had this idea that I wanted to write a book. And so I actually started three different books, and none of them made it past the outline and a handful of pages. And it wasn’t until . . . I read a blog post by Chris Guillebeau, and the gist of the post was basically it’s not hard to write, a few self-published books, a hundred blog posts, he was the all star.

Andrew: . . . he’s written and then afterwards he says, “It’s not that hard to do all this writing.”

Nathan: In one year. And I’m just going like, this is insane. And he says it’s not that hard if you just write a thousand words a day. And at the time that sounded daunting, but I was thinking, okay, a thousand words. That’s like two and a half pages or so, and I have this idea for a book on designing iPhone apps because I was spending all of my time doing. That was my job at the time, and I really wanted to finish this book, and I knew I had a habit of not finishing things.

And so I thought, okay, I want this badly enough that I can commit to writing a thousand words a day and actually finish the book. And so, of course, the first thing I did like any good developer is I built an iPhone app to track how to write a thousand words a day. So that was a little bit of procrastination.

Andrew: It was huh?

Nathan: Yeah. It paid off.

Andrew: It’s interesting actually to you procrastination isn’t going clicking around on Facebook or watching TV, it’s writing an app.

Nathan: Yeah, I definitely do the other procrastination too. You know, I have Facebook and Twitter blocked on my computer for a good reason.

Andrew: I see. If you’re honest with yourself, what would you say is the reason that when you started writing you backed away from it. What was going on in your head that made you back away from it?

Nathan: I always tied everything to my current motivation and how excited I was about the idea. And so I think of an idea for a book or a product or anything like that, and I’ve started dozens of them. And I’d get really excited, and I would channel all that energy into working on the products. And then within a few days I wouldn’t have nearly the same energy and just wouldn’t be able to sustain any kind of work on it.

And so what I started doing later is tying all my effort in the product, in this case writing a book to a specific outcome per day. And so that was a thousand words a day which for anyone who write a lot a thousand words a day isn’t really that much if you were a serious writer, two pages a day. But for me I said I’m going to, at least, show up and do this much. And I figured I would chip away at it until I finished the book. And it took me a [??].

Andrew: But was it this fear if you’re open with yourself that you start to say, “Hey, you know what was going on in my head was I was afraid that my work wouldn’t be as good as Chris Guillebeau,” or “I was afraid that I don’t know enough,” or “that I hadn’t earned the right to write this book because I didn’t create software like Basecamp yet and until then, I can’t do it.” Is it those kinds of thoughts that were going on in your head? What was going on in your head?

Nathan: You know, I’m not exactly sure. I definitely have the thoughts of, “Am I enough of an expert to write this book?”

Andrew: Yup.

Nathan: But I don’t think that’s what was keeping me from actually making any progress or sustaining motivation. I think that I was just so much in the habit of bouncing from idea to idea and relying 100% on motivation right then as my energy source for the work that I was doing.

Andrew: I see.

Nathan: And that’s just a bad way to go.

Andrew: I see.

Nathan: You’ve got to have something else driving you forward because that motivation is going to last a week if you’re lucky.

Andrew: That’s a good point. You have to just keep going, even in those moments where it doesn’t feel like an exciting thing to do, even when you don’t feel like it. All right, so you created an app that allowed you to keep track of how consistent you were with your writing and you decided that you would write a thousand words a day, and along the way you also decided that you would put up a landing page. At what point did you put up a landing page?

Nathan: So I waited, and this is something I wouldn’t recommend people do, but I waited until the book was pretty far along . . .

Andrew: Mm-hmm.

Nathan: . . . because I had . . . I wanted to make sure that I was actually going to finish the book.

Andrew: Mm-hmm.

Nathan: Because I knew my own . . .

Andrew: Did the baggage of all the past . . .

Nathan: Yeah.

Andrew: . . . projects that you didn’t finish, right?

Nathan: Yup. And so I started writing the book in March 2012 . . .

Andrew: Mm-hmm.

Norman: And I put up a landing page in July 2012.

Andrew: Okay.

Norman: And so during those months leading up to it, like I’d started a habit going of writing a thousand words a day and I’d build up . . . I’d track the days in a row. And if I’d miss a day, that count would reset, and so it would be I could get four days and miss a day, seven days and miss a day, and then once I got up to about twenty days or so, I didn’t miss a day again. So by the time I published the book, September 2012, I had about seventy-five days in a row of writing a thousand words a . . .

Andrew: Okay, and how many email addresses did you have by that point?

Norman: I had 800.

Andrew: Eight hundred.

Norman: So yeah.

Andrew: What did your landing page say that got 800 people to give you their email address and tell you that if you wanted to sell to them, they would be open to hearing your sales pitch?

Norman: I can pull up the exact page but it’s pretty basic. It had a book graphic. And so what that does is as soon as you show up to the page, you’re like, “Oh, this is about a book.” Kind of that first glance, first impression.

Andrew: Mm-hmm.

Norman: And then it just had . . . talks about in a couple sentences wanting to design beautiful IOS applications. It had an email opt-in format. It was really basic. I think it converted at about maybe 20 to 25% of visits to email addresses.

Andrew: Okay.

Norman: And then even though it had ended up on Hacker News . . . and then I started writing a handful of blog posts, like dissecting the new Facebook app that had just come out and trying to take design lessons away from that. And after each one of these posts, I’d say, “Hey, if you like this, I’m also writing a book.” And I’d also send those posts to whoever was on my list at the time.

Andrew: Mm-hmm.

Norman: The first list went out to like 40 people, saying, “Hey I wrote this post. Since you’re interested in the book, you’re going to like this post. Also, would you mind sharing it?” And some of those people were some of the first people, like, submitted to Hacker News and shared on Twitter and that sort of thing. And so it just kind of snowballed from there.

Andrew: Okay.

Norman: The next list we got would be to 300 and so on.

Andrew: I want to talk later on about all the different things that you sell in your pack-, all the things that you include in the package when you sell the book because I think that’s really clever. But the first thing that you sold was just the book, written by you, in – I guess it was iBook publisher format, right?

Norman: Yeah. So I wrote it in Scribner and then I designed and published it in iBook’s Author . . .

Andrew: Okay.

Norman: . . . which is Apple’s 320, which is really . . .

Andrew: And that was all there was. No audio version, just the book?

Norman: So before I launched the book, I created video tutorials to go with it.

Andrew: Mm-hmm.

Norman: And so I had code samples and that kind of thing. And all the Photoshop files that went in the code samples, that was in that first version of the book that I launched.

Andrew: I see, okay. And so you didn’t have the interviews and obviously, no case studies at the time. It was that.

Norman: Actually, I did have, I did the interviews as well.

Andrew: You did?

Norman: Uh-huh.

Andrew: Okay.

Norman: I’m trying to remember. I’ve since got, no. I did not have interviews. That was something I added with the next book. And then, when I re-launched the [??] handbook I came back and re-added it.

Andrew: Okay. So you were selling more than just an iBook design – iBook author design book. It was a book with video tutorials, which I’m assuming you did using Screenflow [SP]. Right?

Nathan: Yeah, I think I used Quick Time to record.

Andrew: Oh, the free version?

Nathan: Yep.

Andrew: So you just were recording your computer screen and including that. See, to me, that’s a very smart move. If you were just selling the book, in people’s minds, you could charge them maybe $19.95 tops. Forty bucks would be too much but if you include all these other things, you get to increase the value proposition and increase your price. Right?

Nathan: Mm-hmm, yeah, and I think that the key thing there isn’t just selling, isn’t just having one price. Because what I realized within, you know, the weeks leading up to my launch, is that I had a bunch of different people on that email list of 800 people. There were a bunch of freelancers who probably had very little budget to spend. And then there’s many people, you know, they work for companies. They had a company credit card and so I thought, OK, the freelancer might be able to swing $39. Like you said, that’s like the top end that you would pay for a book and that’s a book that’s going to help you improve your career.

Andrew: Actually, I take it back. Right, the $39 is where you sell just the book.

Nathan: Yeah.

Andrew: So that’s pretty high.

Nathan: Yeah, it is. And then, so then I did a higher package with the videos and everything, like co-examples and all of that together at $129. And the thinking there was that if you want to really save time and you want to learn in this diff way then a lot of people will be willing to pay for it. And so the people buying that, well, my thought was people buying that would be those with company credit cards and that sort of thing. Turns out, way more people buy that package than I thought. And it drove…

Andrew: It [??] cost how much?

Nathan: It was $129…

Andrew: $129.

Nathan: …at the time.

Andrew: Now, don’t you have a thousand dollar package that’s designed to be shared with employees at a company?

Nathan: Yeah. So I, now I do packages at $39.99 and $249 and then, you know, with one, like, kind of fine print package that’s, if you want to share it with your whole team, buy it for a thousand bucks.

Andrew: So where do you learn to do that, to say, I’m not, and get the nerve frankly even to say, I’m going to charge more and I’m going to find a way to get more?

Nathan: Yeah, so the multiple packages thing, that came from Chris Guillebeau. Again, I’ve learned so much from that guy it’s incredible.

Andrew: Really brilliant guy. Art of Nonconformity is his site. You’ll have a hard time spelling Chris Guillebeau if you’re searching for him but you should be out, you should search for him. Look for Art of Nonconformity. Great book. I mean, we…

Nathan: I…

Andrew: Sorry.

Nathan: I learned so much from him that I actually learned how to spell his last name as well…

Andrew: [laughter]

Nathan: Because I felt that but… and then there were two other designers who came out with design books on the same day actually and this was March 2012. Their names were Sasha Grief [SP] and Jared Drysdale [SP]. And I had thought, up until this point, I could that I could write a book but I wouldn’t necessarily be able to make money from it. It would be, you know, kind of a labor of love and might help me get consulting deals and that sort of thing. And they published their numbers and they made, like, $6,500 and $8,000 in the first 48 hours, each of their book…

Andrew: Okay.

Nathan: …and I was blown away. I thought that was amazing. And so they had an interesting pricing model. Sasha was pricing his book at $3 and he had a top tier, you know, high-price edition at $6 and Jared had $39, just flat fee, for his book. And so, based on what I’d been reading from Chris Guillebeau and watching that, I kind of combined their two pricing models where I took Jared’s base price and was like $300? Okay, that sounds good. I read about pricing things based on value and all that and so that was the base. And then I liked what Sasha was doing with the multiple tiers and so I just applied that and went up from there and it ended up being such a good decision. And since then, like, a really a lot of people selling technical books have copied that and made a lot more money because of it.

Andrew: And Sasha worked at Hip Monk, Code Academy [SP]. I forget what else. Great guy.

Nathan: Yeah.

Andrew: Interesting. And he was still underselling his work. Don’t you think?

Nathan: Oh, yeah. He totally was. But, and he’s since doubled the price on that book too.

Andrew: [laughter] Which is still very small. We’re talking about 6 and 12 bucks.

Nathan: Yeah, but it’s also a very small book.

Andrew: OK.

Nathan: It took him a couple weeks, yeah, I think it took him two weeks to put it all together.

Andrew: All right, you expected to bring in how much on the first day?

Nathan: I didn’t have a first-day goal. After hearing their numbers, I thought, okay. If this book makes $10,000 over its entire lifetime, it’ll be a success.

Andrew: Okay, and how much did it make over its entire lifetime?

Nathan: Now that it’s had multiple editions and that sort of thing, it’s at a couple hundred thousand dollars.

Andrew: A couple hundred thousand, wow.

Nathan: But it did $12,000 in the first day, and that just blew me away.

Andrew: How did you 12,000?

Nathan: So having email estimate 100 people, if you were selling it, a really cheap product, that wouldn’t turn into very much money. But when you’re selling a product at three different price points, and those are higher price points, then people are going to self-select into the different levels, and you’re really maximizing the revenue off of a small list. If people are paying you $130 a piece, it doesn’t take that many people to turn it into…

Andrew: [??]

Nathan: Yeah, whereas if I’d been selling it for 10 bucks, I don’t think that many people more on the list would’ve purchased, and I would’ve made a lot less money.

Andrew: How did you know what to include in the packages that allowed you to increase your prices?

Nathan: I just thought about what would help me if I was teaching that to other people, and then I kind of had this deal going with a few guys I used to work with, where they were much better programmers than I was, and I was a much better designer than they were. We’d help each other out on our side projects and apps, and so I knew what questions they had and that sort of thing. A lot of the book I wrote specifically to them because I wanted their software. They’ll look better.

Andrew: I see.

Nathan: I knew what they got stuck in in Interface Builder, in EC code, and all these tools, and so I just tried to…I’d rather video a tutorial…Yeah, a video tutorial just to help them with that, and that’d go to the top package, somehow.

Andrew: What did you say in your email that allowed you to sell so many?

Nathan: I don’t think it was any copywrited work of art or anything like that. I think it was…I had this interesting writing style, probably because I was so timid that it was just kind of like…”I made this [??] thing. I hope you like it.”

I would just tell people and teach through the process of this, what now would call a launch sequence. At the time, it was just like, “Hey, here’s a chapter I just finished. What do you guys think?”

Andrew: I see.

Nathan: And so it came across as probably this really, really natural style that wasn’t salesy at all because I didn’t even know how to sell. It was just like, “Here’s this. If you like it, please buy it.”

Andrew: You told April in the pre-interview that one of the things you were doing on the day of the launch was refreshing your sales stats. What did you use to check those stats on?

Nathan: I was selling through Gumroad, which at the time…See, I think they’ve been out for five or six months, at the time. But I think it was the first independent author to break $10,000 in sales on Gumroad, and now, they’re amazing platform and really good friends of mine.

But yeah, I was refreshing my stats on there as sales would roll in, and I was just blown away that this many people bought it. Actually, I believe the second sale to come through was for the top package, and it was from one of the designers at 37signals who bought it.

Andrew: Really?

Nathan: I was just like, “What?” And that made my day.

Andrew: What do you think it was about your work that drew them to it?

Nathan: I don’t know.

Andrew: You must have given them samples. Those people are very discerning over at 37signals. Yes, they have a company credit card, but they have the company attitude, that if stuff is junk, they have to call it out and walk away, and there’s a lot of junk in the world. What was it, do you think, about what you communicated to them ahead of time, that told them, “This is going to be a 37signals worthy purchase?”

Nathan: I think that just sharing plenty of content in advance, not holding back. One thing that people ask me a lot now is, “If I put this out on my blog, isn’t it that I’m giving away too much?” or something like that. I just think, no. Don’t hold back the audience. Give them stuff that you think is really, really valuable. You’ll develop a reputation for that, and people will be happy to pay you later.

I followed that philosophy for a long…

Andrew: Oh, might have just lost you there.

Nathan: No, I bought your book and I read it, and I thought, “You know what, I already know this stuff.” Actually, I got this very email today. Someone said, “I already know all this stuff, but I realized that I already know it because I’ve read it all from you, in your interviews, stuff like that.” They still ask for a refund, which I thought was odd, but I just replied with, hopefully what wasn’t too snarky of an email, saying like, “Okay, here’s your refund. No hard feelings or anything. Sorry I taught you too much stuff for free.” Just about everyone is thrilled that you give away that much for free, and it’s a great way to build an audience.

Andrew: The other thing you did was, watch as people favored your tweets. What did you say on Twitter that you think spread?

Nathan: Just linking to the articles. Pass [SP], I don’t think…I guess it was two years ago. I don’t think people writing technical books was quite as common, or self-publishing technical books was quite as common then as it is now.

Andrew: Sure, it was. Don’t you think, really?

Nathan: Maybe it’s just that I’m in the world a lot more now, and so I see a lot more of it. I just found that people were so thrilled to share my stuff. Just a very generous community. It’s the sort of thing where if people see that you really put a lot of effort into it, and try to make it great, then they’re going to…Again, here’s a tweet. A bunch of people who followed me, and actually, there weren’t that many people that followed me at the time,…

Andrew: You know what I think a large part of it is, Nathan, tell me what you think about this. It’s the design. When I look at your sales page, it doesn’t feel like it’s an info product. It looks like it’s designed by someone with Apple’s perspective on design. It looks like someone will not allow an image to just show up on the center of a blog post. He has to have it stretch out from end to end, and then another image, it just takes out the right side of it. Those details matter to you. That, I think, is what came through and got people to want to buy it, because they wanted to get that perspective for themselves, too.

Nathan: Yeah. I think that’s true, and especially maybe in the world though, of technical content and training, and all of that. I think that a lot of people don’t pay attention to design. I think you’re right. That does stand out a lot, especially when you’re selling a design book.

Andrew: Yeah, that you had that…I don’t even know if it’s about what you were writing so much as just seeing the design behind everything that you did, that often has impact.

All right, so first day, we see your sales are doing well. It was what, $12,000, you said, right?

Nathan: Yep.

Andrew: Terrific. Now you’ve got to grow it from there. What do you do?

Nathan: I actually, I watched the sales decline over the next few days.

Andrew: Makes sense.

Nathan: Which was expected because all I had [??] email list. My next thought was, “Oh, I did it. I launched my book.” Then my phone, the next day, popped up with a little reminder, and it was the app I had written, which is called Commit.

It said, “Are you going to write a thousand words today?” I thought, no. I wrote my book. It’s done. I’ve broken this reputation of not finishing things and not shipping things. I thought, no, not going to do it. Then I looked, and it said, “Seventy eight days in a row of writing a thousand words a day.” I knew that if I didn’t write a thousand words today, that would reset, and so I thought, okay, I got to keep writing. I already wrote the one book. What to write about next?

Well, I spent a lot of time deigning web applications. Why not write a book on that? I just kept writing a thousand words a day. Ninety days later, I published another book “Designing Web Applications.” Took what I learned about marketing and pricing and all of that, and actually got some help with Passion [SP] MacKenzie for pricing on that one. He sent me an email. He was like, “Yeah, this is the first time I’ve seen products on happy [??] news recently that I didn’t think wow, his pricing is completely stupid.” That was his lead-in to helping me tweak the price a little more and actually…

Andrew: What did he charge?

Nathan: What’s that?

Andrew: What did he charge you to help you?

Nathan: He didn’t charge anything.

Andrew: Nothing. Isn’t that amazing? You’re not the first interviewee that he’s done that for. He just reaches out to someone, out of nowhere, and then he helps them out for free, which frankly, he should be charging. He’s telling you to charge. What did he teach you about charging?

Nathan: He said he really liked the tier pricing and that sort of thing, but he thought my prices were too low. He thought the $39 package was just fine, but that the top end package needed to be higher priced. I think it went up from $129 or $150, something like that, up to $249, and that’s…

Andrew: [??] come up with that? How did you know that that was the right number?

Nathan: I can go back to the email that he sent, but basically what he said is, there’s no difference for someone with a credit card between $150 and $250. I led a software design team at a previous company, and I’d been that person with a company credit card, plenty of times before. It took him saying that for me to really internalize it. I thought, “Yeah, he’s absolutely right, so I just bumped the price up, and so, I can actually do the math on what different tier pricing has had on each product watch, and on the first book, it doubled the revenue. So I’m actually in a book, using tier pricing, doubled the revenue, and then after Patrick’s little tweaks and some things I changed on the sale page, tier pricing tripled the revenue on the next book.

Andrew: How can you tell that it’s triple? Are you saying the higher priced items brought in twice as much as the lower priced item?

Nathan: So what I’m saying is, if you have a certain number of people that are going to buy the book, and you only give them one option, they’re all going to pay you $39 because-

Andrew: I see, got it.

Nathan: -they decide to buy, and the person who has a $500 budget to spend on training can’t give it to you, even if he loves your stuff, because you didn’t give him a higher priced version with more value or anything like that, and so based on the number of sales and all that.

Andrew: All right, so a second book isn’t going to get you to hundreds of thousands in revenue. You had to do more to market it. What did you do that was new?

Nathan: On that one, I reached out to a bunch more people. So I’ve written guest blog posts, a few, when the first book came out, and so I wrote a whole bunch more for this one, and I also tried interviewing other people. I think I had been too shy to reach out to other people to interview them, but after seeing success with the first book, I had some confidence and so I did all these interviews and added them in with the top packages on the new book, and that did really well, and then cause especially the people that I interviewed shared the book when it came out.

Andrew: You interviewed them, as each interview was going to be a separate product, except for video you were including with your package. I see, did you pay them anything for it?

Nathan: No, I didn’t, and I don’t think most of them would have done it if I tried to pay them.

Andrew: Why do you think that?

Nathan: Because, well the example I’d like to use is, there’s all these developers who spend a ton of their time building open source software for free. And so imagine, you know, maybe you’re using this web based plugin that some developer spent hundreds of hours on, and you say ‘Hey, will you make this one tweak for me? I’ll pay you 5 bucks.’. Well, they’re going to be pretty upset with you right then, they bill out their time at 200 dollars and hour, they’re a top tier consultant, and all this stuff, and you offer them 10, 5, 10 bucks, whatever to make this change. That’s offensive, but if you ask them ‘Hey, you should add this to your software.’, they’ll be like ‘Yeah, we’ll do that.’, as long as you don’t get money involved because this plug in or whatever is their hobby, and they’re happy to help, they want to make the internet a better place, that sort of thing. So I think once you bring money involved, you can’t pay people what they deserve. It just screws up the whole relationship.

Andrew: They just accept it as a favor. If you can’t pay Chris Gilhool what he deserves to get paid to do an interview that then becomes part of the product that you sell for one of your top tiers, might as well just pay nothing and accept that you just did him a favor, sorry, that he just did you a favor, and you owe him a favor, and somehow the world will even itself out instead of saying ‘Can I pay you 100 bucks, because this is going to be an hour.’.

Nathan: Yeah, or like imagine if I tried to work out a revenue share agreement with Jason [??], and say this is one of many interviews in the book, so what if I pay you 2% of gross sales? He’s just going to be like, ‘This is stupid.’, and he’s never going to take the interview.

Andrew: I find that people don’t want to be paid, I think I wanted to make that point because I’ve ever had anyone once say “I want to be paid for doing an interview.” What I have had, strangely, people say is “I will pay you for this interview, and in their minds the thinking is ‘I’m going to plug something really aggressively and Andrew’s going to help me because he’s going to get a share of the commission and so it’s worth paying him money so he plugs it really aggressively with me.’, and I say no to that. I know others are cool with it. So more blog posts, guest posting is what helped you?

Nathan: And growing a bigger e-mail list. See, what I learned is since I was writing on a related topic, those 800 people I have for the [??] handbook, they didn’t go away. I never had to start from scratch on this next product. As you built an audience, you never again start from scratch. Even if, like Andrew, if you were to start a new project that maybe only had 20 to 30% overlap with the audience from [??], you still don’t have to start from scratch, a bunch of people are going to come over and follow you there.

And so that made a big difference. So I launched the book, “Does Anyone Know About Patience,” to an audience that was three times as big because I kept going on the same practices but did some more guest posts, got the people I helped interview to help promote it, and had some improved pricing. And it ended up making $26,500 in the first 24 hours.

Andrew: Really?

Nathan: So more than double what the last book had done, and then by the end of three weeks it was just that book was over $50,000 in sales.

Andrew: Really?

Nathan: Yeah.

Andrew: Guest blogging, promotion from people who are in the book who say, “Hey, I’m in this book, and it’s a great book. Go get it.” Wow. And your own personal list that just kept growing.

Nathan: Yeah, so I should add, the guest blogging. I since figured out how to make that effective. It’s something that I put a fair amount of time into for those launches, but it was not effective at all.

Andrew: So what did you do?

Nathan: I wrote blog posts on my web designer Depot or Six Revisions or any of these sites, and they drove back a tiny bit of traffic, but it didn’t return in sales. What worked a lot better was giving away some kind of like writing something in the [??].

Andrew: Let’s wait for the connection to catch up with the conversation. Let me see. I thought we lost you there for a moment. You’re saying, writing something and what? Tying it back to something else.

Nathan: Oh, so [??] was a comeback to get something else from me for free and sign up for my email list. That’s what worked. Sending people that never heard of me straight to a sales page, it doesn’t work at all.

Andrew: Give me an example. You do a post where and what are you offering to people who come back to your site?

Nathan: So the biggest success with this I’ve ever had was a post I wrote for Smashing Magazine, and it was like a 4,000 word post on product launches.

Andrew: Okay, uh-huh.

Nathan: And so it’s really, really in depth, and this was after the books and everything.

Andrew: You just had a profit from selling “Digital Products Part One?”

Nathan: [??] I’ve done more recently.

Andrew: Okay.

Nathan: I think this is the post which was How to Launch Anything.

Andrew: Okay.

Nathan: And so I write this really long post and then at the end, instead of just relying on a little link in the author file, I actually timed the end of the post. And some editors may not let you do this, but I did it really naturally. And said, “You just read all this stuff on product launches. You obviously care about it. I don’t know your education in here so I put together a brief three day course on mastering product launches and go sign up, it’s free.”

And, I think, the editors at Smashing Magazine, they wanted to take a look at the course and make sure . . . Hey, can you send us some sample from . . .

Andrew: Make sure it’s not all nothing, not all promotion.

Nathan: Right. And they were thrilled with it, and people loved that course, but that one blog post with a link to the email course got me over a thousand email subscribers.

Andrew: Really? Wow.

Nathan: Which I would since tie back to, at least, 50 grand in revenue.

Andrew: Fifty thousand dollars from this one post because you also linked it back to your site and offered people a free course. And then at the end of the free course you said, “No, I don’t want this to end If you want to purchase by. Wow.

Nathan: What I found is when you have a handful of products at the right price points and that kind of thing, email addresses are really worth a lot of money.

Andrew: Mm-hmm.

Nathan: So we’re not talking with the first sale. People who buy multiple products and really they’re part of your ecosystem. So, yeah, it ends up being worth a lot. That’s why I put so much energy and attention into growing an email list.

Andrew: What about that the course gives away so much for free and why would anyone want to sign up if you’ve given away all of your best stuff?

Nathan: Books are long enough that even if you give away a ton of stuff free there’s still lots more great stuff in there. And a lot of people want to, if they learn so much from you, they want to support you. Yeah. I think generally the approach is demonstrate so much value that it makes the purchase really easy, and if some people feel like, you know, there’s 70% of new content in the book isn’t enough, they’ll ask for a refund and, you know, you always get some people asking for refunds. That’s fine. Don’t get upset over it, just issue the refund and move on. But, yeah, I’d say if you get people to trust you and if you help them they’ll be happy to pay for it.

Andrew: Do you use any affiliates?

Nathan: I have done a few random little affiliate things, like I consider App Sumo an affiliate, tech thing. We’ve done that three or four times, but otherwise, [??] didn’t have any affiliates at launch. A few people have been like, “You’re missing out on so much revenue” and all this stuff. I don’t know. I’ll figure out affiliates someday. It’s on the list.

Andrew: What are you doing with…Is it Tapity?

Nathan: Tapity, yeah. That was just last year. It came time to update. iOS 7 came out. My book was quickly going to become out of date. I moved on to lots of other things, where I had an email marketing company that is growing, I’d written a couple more books, and yes, [??] was my worst selling book at the time. We’re still doing just fine. It’s doing maybe $3 or $4,000 a month without much promotion.

Picking time to update the book, and I didn’t want to write more about app design this time. It wasn’t an interesting topic to me because I was so focused on all things marketing and that’s what I really cared about.

A couple of friends at my mastermind group, basically cut through my whining about this, and said, “Okay, you have a couple options. Basically, you either suck it up and rewrite book for iOS 7, which is a huge rewrite. You find a co-author, and they gave me a date to find a co-author by, but it was like seven days later. I said, “Will you take the book down from sale?” I wouldn’t have missed that couple thousand dollars a month in revenue very much.

They laid out those choices clearly of focusing on the things or what to do, and I decided to find a co-author, and I ended up coming across Jeremy Olson. He read my other book “Authority.” He was interested in building an audience around app design. He’s a fantastic designer, had won an Apple design award. He’s actually better qualified to write a book than I am, so we ended up partnering up. We split the revenues from the new edition.

Andrew: He rewrote the book and you marketed the book.

Nathan: Yeah. Now, I’d say the content is about half mine, half his.

Andrew: I see, and Tapity is his personal blog.

Nathan: Tapity is his consulting company.

Andrew: Consulting company.

Nathan: If you need fantastic designers to build you an iPhone and iPad application, they do amazing work. Yeah, we wanted to break into the training and publishing space and it worked out really well.

Random facts about Jeremy is, he and I are born on the exact same day. I’m not talking we have the same date, but I mean…

Andrew: You are the same age, exactly.

Nathan: Exact same age. I’m not sure who’s older, but whichever one of us is older, it’s by a couple of hours. Anyway, random thing about Jeremy. He’s been a fantastic…

Andrew: I didn’t realize that was his site. I saw him on the cover of the book on one of the pages, here, one of the open tabs, but I didn’t realize that that was his site.

By the way, as a designer, now I’m clicking around your site. I love your design. What do you think of this? Does this look great on camera to you, that I have this big cage around my mic? Because I don’t think I really need a shock mount. It’s not like there’s so much shocking movement in here.

Nathan: I think it’s just fine. I don’t think it intrudes any more than [??].

Andrew: I wanted to intrude just a little bit to send the signal to the guest, “Hey, this is a real professional interview, but not so much that it distracts.”

Nathan: Right.

Andrew: And you think that that we’re doing okay there.

Nathan: Yeah. If I had my recording set up, then I’d have a shock mount coming into the screen as well, but right, I just have a little microphone.

Andrew: Really. That’s the blue snowball that we’re hearing? Usually, that mic is just a little too quiet.

Nathan: Yeah. I don’t know. It’s what you’re hearing.

Andrew: Yeah. That does sound like a really, really good mic there.

Let me see what else we want to talk about. Oh, I should say this. Anyone who’s listening who wants to follow up and says, “Hey, you know what? All this guest post sounds interesting, all this marketing automation sounds interesting. We got a couple of courses that I’d like for you to check out.”

The first is with John Morrow. I know the course is about growing an email list, but John is fantastic at doing guest posts and converting those guest posts into members of his mailing list and then selling products without being a pushy salesman.

Well, he did a course on Mixergy that I urge you to take. It’s called Grow Your Email List. He’s fantastic. He’s clearly an experienced speaker, who knows how to tell stories, who backs every step that he gives you, the audience, with a specific thing that you could do, and with examples of how he did it. He’s not just pontificating he’s showing you.

“This is what I did, here’s a screen shot of how I did it, here’s how you can do it yourself.” Great, great course and then there’s also another one that I wanted to recommend and I just now forgot it because I was so busy gushing about John Morrow. So I’ll tell you what instead of forcing a second one or forcing myself to try to remember it, I’m just going to tell you John Morrow is that good, I could forget all my other guests when I just look at his work. It’s really good and I urge you guys to take it.

Nathan: I’d stay that guest posts, if you do them correctly, are one of the best ways to grow your email list.

Andrew: So what else can we do correctly? He also says don’t just leave it as a guest post with a standard bio, the standard link from the bio to your site. he says make sure that you give people an incentive to come back to your site otherwise they’re not going to do it. You said it, what else?

Nathan: I like to tell stories in my posts because one thinking is that, so the people who don’t come back to get that incentive and come on my email list, I want them to at least remember me and so instead of just being like very robotic, here’s how to design a website or whatever the post is about, I like to tell personal stories that tie into the post. It makes the writing more interesting but it also means they’re going to remember, “Oh, yeah, there’s that Nathan guy.” I don’t want them to ever get to the end of a post and not know who it was written by.

Andrew: And associate the great quality writing with Smashing Magazine as opposed to with you. You want them to know it’s you.

Nathan: I want, to have a distinct style, I want to be recognized and I don’t want them to think this is just another post on whatever site.

Andrew: So how do you tell a story?

Nathan: That’s something I’m constantly learning but usually it’s as I’m writing something whatever pops into my head, it’s some anecdote. I have a lot of stories of failed design projects and that kind of thing from my start up days when I worked on a design team and so just try to launch into one of those.

Andrew: Here’s what I learned maybe this will help you realize some of the things that makes you a good writer. One of the things I was told, one of the things I try to do, if there is a point I want to make I think back to my life where I experienced either doing it well or failing at it, and then one of the big lessons that I learned from Dale Carnegie was, we always used to teach students there to jump right into the action of the story. No backstory. So, if I want to tell you about the time that I bought my dog a muzzle I start out by saying, “I bought my dog a muzzle and as I logged on to Amazon I thought to myself, this muzzle better really protect him because”, and then I give the back story that way. But you start with the action and then you try and keep it active as much as possible.

Nathan: That’s good.

Andrew: What else, what have you got?

Nathan: Now I’ve got to follow that? I think being vulnerable in stories, it’s really easy and especially after I had a handful of successes to tell people about, it was really easy for me to tell stories that just made me look good. But I found the ones that resonated with people were when I told stories of failures or maybe it was eventually a success but it didn’t make me look amazing all the way through the story, and so I think vulnerability is really, rally important to get people to connect with you.

Andrew: All right, and speaking of vulnerability you broke the streak. The one you were so proud of, the one that finally got you writing a book, the one you kept track of using your own app, the one that you talked about on your site. You broke it, how did you break it and what happened?

Nathan: So, as you mentioned I was amazingly proud of this streak. It became a huge part of my online identity that I had written 1,000 a day for 500, 600 days in a row. And I don’t actually even know how long the streak was when I broke it. It was somewhere in the 675 range, something like that.

Interviewer: So a little over two years, or roughly two years.

Nathan: Roughly two years, not quite. And, you know, life at some point just kind of fell apart. I think it started with my second son was born and that was challenging. And I went through a couple of week period where basically both my kids stopped sleeping, I had a two year old and a two week old at the time. And so that went poorly and then I ended up just with all these health issues. What I came down with I got shingles, which was, I later found was stress induced, it’s amazing how much bad things will happen to you because of stress. And so everything…

Andrew: All right, so instead of going into all the things that broke apart because of the stress, I’ve got to push you and ask you, what happened that was so stressful? It looked like you were doing well at the time. You were on a streak. You were making money. You were doing what you loved. But underneath it was a lot of stress. What was the stress from?

Nathan: The stress was from all things outside of the business. So it was that we just bought a house, and we were remodeling it. It was a brand new kid, all that kind of thing. And then it just all built on itself. And so then after breaking that streak and realizing it, it was actually like a couple months that were . . . I just couldn’t find the motivation because my first thought was once I broke the streak I’ll get it right back.

That was over two months ago, and my current streak of writing a thousand words a day is at eight days in a row.

Andrew: Wow.

Nathan: It took me a long time to get it back, and for the last three months or so it’s been a constant struggle of motivation, depression, focus.

Andrew: Depression.

Nathan: Yeah.

Andrew: What’s that about?

Nathan: So I think I tie a lot of my personal identity and self-worth in what I accomplish. And more that I have accomplished, writing three books in a year, that kind of thing, the easier that it is to do that. And so I went through a couple of months getting very, very little done. I started to fall into that rut and then feeling less and less motivated. And it was actually a comment on Reddit, of all places, that really got me thinking, and it was just a one line comment that somebody said. “Depression doesn’t feel like sadness. It feels like apathy, that you just don’t care anymore.”

And that got me thinking that, “Oh, maybe I’m actually depressed. And then it’s been . . . I think I read that a month and a half ago, and so it’s just been kind of a journey of getting rid of all the stressful things, getting health back in line, and trying to feel successful again. So I started picking one thing each day that when I accomplished that the day was a success.

Andrew: Have you considered suicide at all, honestly?

Nathan: Not recently.

Andrew: No. Why did you?

Nathan: That was something back in high school. I think that’s fairly common, but, yeah, not recently.

Andrew: It’s not part of this depression cycle. This depression cycle is just plain apathy.

Nathan: Yeah.

Andrew: It’s not . . . You said earlier that you feel like a fraud in everything that you do. I wrote that down, “In everything I do I have imposter syndrome.” Why?

Nathan: I think there’s always someone more qualified to do it. There are plenty of designers who are way better than I am. There are plenty of business people who would grow a startup and a company way more effectively than I would. You know, every time I do a product launch, even though I have this past success, this one might be the one that flops. But you know what? Even the people I talk to who are deploying businesses way bigger than mine a lot of them feel it too.

And so it’s something that I’ve come to accept that I’m always going to feel not qualified and not ready to do what I’m about to do. And I’m trying to remember who told me this, but basically if . . . I wish I could give them credit, but oh well. If you do feel ready and fully prepared for what you’re about to do, then you’re probably not shooting high enough. You’re working fully in your comfort zone, and you’re not going to improve and make progress.

Andrew: You understand what it feels like when you feel like a fraud, and for me it’s things like, if I’m about to create a page explaining something that I’m going to launch it’s a vision of may Chris Guillebeau and how pretty his pages are. Today it might be yours. I’ve studied yours so carefully in preparation for this interview.

In my mind it wouldn’t feel like an imposter, it would be more like, how could you allow this page to go out when Nathan respects you and Nathan created all these beautiful pages and he cares about the background to such a degree that there’s even a grid on the background of one of his pages? So it looks like graph paper. He’s paying attention to things that you don’t even know how to identify. What is it like for you?

Nathan: For me it’s more looking at people above me than, I guess, the people in my audience. There’s a thousand times . . .

Andrew: Who? Who’s the other person who comes to mind sometimes?

Nathan: It depends on the category, but Chris Guillebeau and all writing things blogging on all awesome software . . .

Andrew: Rob Walling on anything software.

Nathan: Yeah.

Andrew: When you were creating ConvertKit did you think of Rob Walling and say he would do this so much better?

Nathan: Yeah, to some extent. Now there are a lot of other people. I have Amy Hoare [SP] in my head every time I’m writing a sales page or something like that. I have this tendency to want to jump in and design a sales page before writing it. I think oh, Amy would be telling me no, no, you’ve got to write all the copy and pay attention to the written word before you jump into design.

Andrew: Interesting.

Nathan: I have all these little…

Andrew: Those are helpful, though. Is there a voice that’s not helpful?

Nathan: I don’t know.

Andrew: Okay.

Nathan: I think the voice for me that’s not helpful is that you’re not qualified enough to do this…

Andrew: It’s who are you to [??]…

Nathan: …just that…

Andrew: …You’re not qualified enough to do this.

Nathan: Yeah. Who are you to write a book on designing iPhone apps? You didn’t design the Facebook app or Foursquare or something like that.

Andrew: Did it hurt when I started this interview with that comment?

Nathan: No, because you warned me that it was coming.

Andrew: If I didn’t warn you it was coming, how would it feel?

Nathan: I would’ve been taken off guard a little bit, but I think it’s something that I deal with and think about enough that it’s an easy thing now to answer.

Andrew: Okay. I want to end it with this. I tried to see what ConvertKit’s landing pages look like. I don’t see anything about it on this site. Your designs are so beautiful. I just wanted to go see what is the design going to be that you would create for me if I were to use ConvertKit to create landing pages for myself. All I see is the course. Is that intentional?

Nathan: It’s just a fact that the landing page functionality came out three weeks ago. For a long time ConvertKit was just creating drip courses.

Andrew: It was email software that allowed you to create drip courses.

Nathan: Right. What we realized is we need to make it as easy as possible for people to capture as many leads.

Andrew: I see.

Nathan: So, we need to have landing pages as well to do that. That was the reason for adding that functionality. It just hasn’t made it on a refresh of the marketing site yet.

Andrew: Okay. We talked about this before we started, that I really like the way your software lets publishers organize the email that they want to drip out. It looks like… I don’t know how to describe it. It’s just logical. You could easily see this is the first email, and if you click it here’s what goes in it. You can see on the left all the other emails in a row, and you can sort them by just dragging and dropping where you want them to go. Drip email is so powerful, but for some reason it’s incredibly complicated on other software packages.

Nathan: Yeah.

Andrew: On some, like AWeber, it feels like an afterthought.

Nathan: And on MailChimp as well. I came into this from MailChimp where I got into email marketing.

I’ll be the first to say that I was amazingly late to the game. I told one of my Internet marketing friends, like, did you know how well email marketing converts. He’s like, yeah I’ve known that for a decade. I was very late to the party there, but I learned all these techniques that worked really well like auto responders or drip email.

Then, when I’d go to set it up in MailChimp or another program it was such a pain that I just wouldn’t do it, even though I knew it would make my business more money, because I was so frustrated with it. Then, my thought was if other people are just as frustrated as I am then I should solve that problem. That’s what got me back into software.

Andrew: Who coded it for you?

Nathan: I’ve had a handful of different developers working on it. The current guy is a guy named Mark who’s been in my audience for quite a while. I will say that if you have to hire developers, having a popular blog read by software developers is like the ultimate hack for hiring people. It makes it so easy. You just say hey, I’m looking for a developer, and then you get like 20 people who say pick me who already know what it is that you’re working on and that kind of thing. I would say having an audience is a hack for all things online business.

Andrew: It really is for all things online in general, and for just making it in a brand new country. If you just happen to be in town you want to know what’s available, boom, you go to your audience. You say I’m here in this new country, and they know you, they know what you’re about, and they can recommend good things.

I remember being in Patagonia and the founder of a vineyard, a winery there, emailed me. Michael. Why am I not thinking? The Vines of Mendoza. He emailed me. He just happened to hear that I was in town, and I got to go and have an asado – a barbecue – at his place. It was beautiful.

Nathan: Wow, yeah.

Andrew: You don’t get that kind of experience if you just walk into town and you try to figure things out for yourself. Yelp isn’t going to do it for you.

Nathan: Right. Yeah, I’ve been taken out to lunch in Costa Rica before, because somebody saw I posted on Twitter that’s where I was. They were like hey, I’d love to meet up. So much good stuff comes from the audience.

Andrew: You know, I should say this, that by the time this is up if anyone wants to they can learn a little bit about how to do interviews the way that I do by just going to I really urge you to do those interviews, because they’re a good way of getting to know your heroes, and then publish them online so that you build that audience for yourself. And, when you are in Mendoza maybe the founder of The Vines of Mendoza will reach out to you, too.

All right, Nathan. If people want to follow you, I told you before we started there are too many places that I could suggest that they go to. How about we pick one and say this is the place where you can go if you want to connect with Nathan or see a sample of your work.

Nathan: Yeah. I’d go back to that. We talked about it earlier, the email course that I put out for the Smashing Magazine readers. It’s If you sign up there you can reply in the first email that comes out, and that’ll come straight to me. You’ll have my contact info. Also, if you’re into marketing and launching books and all of that, I think you’ll really love that content, and it’s totally free.

Andrew: Cool. The form there, and the whole landing page, is that created by ConvertKit the way I see on the bottom?

Nathan: Yeah, it is.

Andrew: So we can see a sample of what your landing pages look like there. All right. Thank you so much for doing this. Thank you all for being a part of it. Bye, guys.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.