When it comes to publishing on Gumroad, Philip Kiely is an open book.

Since he published Writing for Software Developers, Philip has detailed every step of the process, from writing, marketing, and selling the product, to building the landing page and transcribing audio interviews. His radical transparency offers a blueprint for other creators, and his habit of sharing metrics mirrors the philosophy of Gumroad itself.

This week, Philip published the Audiobook version of Writing for Software Developers, a free addition to the existing product. We asked Philip to reflect on his journey, and here’s what we learned.

“I Bet There Are Other People Out There Who Fit That”

At Grinnell College over the past four years, Philip majored in Computer Science. “But even though I’m a CS guy,” he said, “I have a background in writing: I come from a family of writers, I’ve done stuff with the school newspaper, and I took a lot of English classes on top of my CS course work.”

Eighteen months ago, he read Nathan Barry’s book Authority: A Step-by-Step Guide to Self-Publishing. After reading the book (and discovering Gumroad), Philip started writing articles for clients. Within months, he was successfully pitching his work to respected technical magazines, including FloydHub, CSS Tricks, and Smashing Magazine.

“That was super cool to me because I was just some college kid, and these are the biggest names out there in tech publishing in terms of 2,000-word tutorials. I was getting a 50 percent and higher success rate on cold pitches to giant publications.”

Reflecting on that experience, Philip said, “It turns out the reasons for this is there’s just a massive demand for how to do X in Python, how to do Y with JavaScript, AngularJS, React, and a lot of developers don’t feel super confident about writing technical tutorials, or writing anything for that matter, and so there’s a supply-and-demand issue.”

In September 2019, Philip received an email from the person who hired him for his first technical job, an internship during his sophomore year. The email said, “Hey Philip, I see you’ve been doing all this writing stuff, can you teach me how to do that? Can you teach me how to get published?”

In response, Philip wrote a short ‘how-to’ guide and charged a small consulting fee. “Then I got to thinking, hang on: A. This guy has ten times more work experience than I do, and he’s asking me about this; and B. He’s willing to pay for it. I bet there are other people out there who fit that.”

By Thanksgiving Break, Philip was standing in his kitchen telling his Mom about his idea for a book. By the time the semester ended in December, he had the book outlined. He worked on it over Winter Break, got back to school and started taking it more seriously so he could get it done before he graduated.

“COVID hit, my school shut down, I moved home – my classes moved online and became not difficult at all. I just turned this into a full-time-plus job.”

Adding Interviews and the Power of Cold Email

“The book that I outlined originally was much less ambitious in scope. I was planning on writing it just over Winter Break: ten thousand words, put it out, maybe even for free, and just start to build some audience. Then I realized I had a lot more to say on the subject than the original outline.”

After Philip added everything he could, he realized he didn’t know everything there is to know on the topic, or even the majority of what there is to know. “Even if I did, people wouldn’t necessarily believe me. And it’s not that I want to be believed for the sake of being believed, it’s that I want to be believed because the information is legitimately good, and I want people to use it.”

Philip is a huge fan of cold email. He sent 100 personalized notes and got 11 interviews for the book from prominent and knowledgeable experts in the field, including Patrick McKenzie, Tracy Osborn, Courtland Allen, Daniel Vassallo, and Chris on Code. “A cold email is so easy if you don’t overthink it. My template is ‘Hi, then one sentence about them and why they’re cool, then the minimum number of words to explain what I want, then just making the ask as small as possible. That’s it.’”

Launching the Product

“Over the course of a couple of months, I cranked out the book, had it professionally edited, got the cover art, and got everything put together.” Throughout the process, Philip kept the interviewees up-to-date, and a few of them contributed a lot to the launch.

Philip thought about publishing the book himself, but the writing and editing went down to the wire. As he put it, “It wasn’t worth trying to build it myself. I set it up on Gumroad and it took only a few minutes.”

And with that, Philip launched his first product six days before graduating college, at 21 years old.

Soon after, he posted a link to Hacker News. “It’s 8am Central Time, I post everything, I’m sitting there waiting, I’m just super tense for fifty minutes, then I sell my first book, and then another. I’m screaming to my family, ‘I sold a book, I sold another.’ Philip made $1,000 in the first hour, $3,000 in the next three hours, $10,000 in eight hours, and $20,000 in the first 24 hours.

In the three months since publication, he’s sold 700 copies, earning a Net Income of more than $25,000.

Enabling Inverse Multi-Generational Family Businesses

To this point we haven’t highlighted a central figure in Philip’s creator story: his editor, Robin Bourjaily, who happens also to be his Mom. Robin subjected every sentence of Philip’s draft to multiple edits, helping him structure the draft and ensure it was copy-edited to a professional standard.

Now the tables have turned. “A super powerful way of generating wealth is multi-generational family small businesses. Gumroad is enabling these kinds of businesses — and this kind of wealth creation, which isn’t a thing yet but I think in ten years will be. The idea of entrepreneurial people in my generation figuring out ‘online,’ and then passing that information back up a generation. My Mom is about to launch stuff on Gumroad herself, selling fiction books.”

Robin has been selling her work on a different platform. Now she’s porting that book and one brand new book to Gumroad.

Four Levels of Abstraction — In Philip’s Words

Philip thoughtfully reflected on a universal problem worth noting:

This is not a Gumroad-specific problem, but the best way to make money online is to teach people how to make money online. And this is something I’ve thought about a lot because my book does approach the line. On the one hand, it does teach an exact skill, not a meta skill: this is how you sit down and you turn knowing how to code into other people knowing how to code. But a good portion of the book is dedicated to the art of monetizing that afterwards. I felt comfortable publishing something like this because it was about a real skill. That’s not to say there isn’t value to this meta material.

At the same time, that’s another reason I go for transparency in my metrics and why I make all these blog posts.
First and foremost I’m a software developer. Then, there’s second level of abstraction: I write articles for clients about how to code. Then there’s a third level of abstraction: I have a book about how to do the second thing, which teaches people how to do the first thing. And then these blog posts are a fourth level of abstraction: it’s about how to do the third thing, that teaches you how to do the second thing, which teaches you how to do the first thing. And it can be really attractive to just keep piling on top of those.
Someone has to be at the top of all this, but it’s important as I do this stuff, and I think about what my second book is going to be, or what my next projects are, that I don’t just keep building up abstractions. It’s important that I stay focused on what happens in my daily work as a software engineer: what clients and readers are looking for every day when they’re trying to learn new things; what fundamental skills programmers need to know. It’s important to keep that as the focus of my work rather than chasing any kind of meta-content for its own sake.
Links:
Writing for Software Developers
Philip's Twitter
Philip's Website

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