Gumroad #14DayProduct Challenge

The #14DayProduct Challenge, run by Randall Kanna (Head of Community at Gumroad), is a two-week structured challenge that guides participants through creating a product start-to-finish.

This note chronicles my journey to building my second-ever information product over the course of the challenge. Please forgive any typos or errors, this is a process doc not a polished product.

While the challenge is in progress, the most recent day will be at the top, then the days start at 1 and go chronologically.

DAY 1: Just Get Started

Day One is all about coming up with a good idea for a product. Not the perfect idea, not the only idea you'll ever have, just an idea that is good enough to spend two weeks working on. The email starts from first principles and walks you to the intersection of what you know, what you care about, and what you think you can sell.

Pick a Topic You Already Have Expertise In

I totally agree with this advice, expertise is everything here. I’m a good writer and I have training in journalism and creative nonfiction. I have a liberal arts degree, I can do research and write papers. These are skills that help me write about anything.

What matters here is the definition of expertise. Having expertise doesn't have to mean that you are the world's foremost authority on a topic, only that you have earned experience and a yellow belt mentality. It helps if you can identify your expertise as the intersection of two or more topics, like I did with Writing for Software Developers.

Keep Your Scope Small

One day I will write WfSD 2.0 and it will be awesome. That will take another six months after I’ve done a while more of living and learning. I have some SaaS ideas. I have some ideas that I'll be working on for the next couple of decades.

Here, we have 2 weeks. I am spending a few hours per day on the product and challenge. Let's say 50 hours over the course of two weeks as a maximum. That is between five and ten percent of the time that it took to create Writing for Software Developers. So, it stands to reason that I can create something of five to ten percent the scope.

One important factor is that like with all things there are fixed costs and variable costs when creating products. Marginal costs are easy, editing an hour of video takes six times as long as editing ten minutes of video. Fixed costs, like setting up a product page, are a larger percent of the total investment in a small product.

Find Your Reason Why

The fact that I'm the Head of Marketing at Gumroad and I want to see this challenge succeed would be enough for me to sign up for this challenge and participate. But, to give my product the attention that it deserves, to deliver the most value possible to everyone who buys it, I need a motivation beyond that.

Motivations are often quite personal. Here are some personal details: I'm a 21-year-old college graduate, I live in my childhood home and barely ever leave it because COVID and cold, I have my dream job, and I want to build a big enough company to hire all of my friends from college and make us independently wealthy. Some stuff (work, business) is going really awesome, for which I am quite grateful. I'll leave the other hand unsaid.

It took me surprisingly little time to introspect up a good number of motivations:

  1. Challenge Myself: When I was in undergrad, I went to hackathons about once a semester. I always had fun, got a bit exhausted, and promised myself I'd never do another. Well, this is a bit like a hackathon and I'm a sucker for an intense, time-boxed challenge with a clear feedback mechanism.
  2. Create Value: I'm really happy with my first book, but I think I have more to offer.
  3. Win a Bet: Randall and I are in a race to see who can make a million dollars on Gumroad first. We are both VERY far away but right now I'm a bit behind. A small product launch could improve my competitiveness.
  4. Copy Daniel: I've seen quite a bit of success copying Daniel Vassallo's strategies. After he launched his first ebook, he created a second info product in a relatively short amount of time for a somewhat broader audience. It worked pretty well so I will try it.
  5. Launch Something: May 12, 2020, was the best day of my life. I launched writing for software developers and within 24 hours my career trajectory was altered forever. The rush from launching successfully carried me for weeks. I am not ashamed to say that I want to have the experience of seeing revenue go up every time I refresh the page again.
  6. Momentum: Like many young people living at home, it can be a bit difficult to maintain work discipline, get motivated, and continue to grow. Having accountability and community should help me establish a streak of good days.
  7. Funds: I know that it is possible to have a very profitable launch. I am hoping that in mid-November I'll be moving up to Minneapolis for an unspecified period of weeks to live with some friends. While I could certainly afford to do that as things are, I'd prefer to launch this product and then go up north until the money runs out. By associating this external factor with the challenge, I'm able to get even more motivated.

So a nice balance of motivating factors.

Action Items

Ok now we finally get to something useful. I have a small confession, which is that I did my thinking about topic a few days in advance of the challenge. This section and tomorrow's section will walk you through how I arrived at my product idea.


  • What are the challenges your audience might have? If you don’t have an audience, what is the topic you’d like to create a product about? What are the challenges that people in that niche face?
    • How do you get clients and jobs?
    • How did you get the interviews for WfSD?
    • How do I reach an audience?
    • Should I write a book?
  • What really inspires you?
    • Other people
    • The promise of an open, connected internet
  • When people come to ask you for advice or help, what questions are they asking?
    • Resume/job search from friends and classmates
    • Writing advice
    • Resources and research
    • Product Launches
  • What do you know a lot about?
    • writing for software developers, but we've talked about that
    • The creator economy
    • Finding someone who knows a lot about whatever the topic at hand is
  • What is something you can create value on in two weeks?
  • Does your product idea solve a specific pain point for your audience?
    • Overcoming fear or doubt
    • Public/online presence
    • Writing for a specific purpose

List of 3-5 Product Ideas:

  • Cold Email for Interesting People (the one I'll be doing)
  • Resume Template
  • Reading for Software Developers
  • Hire your First Developer Advocate
  • Some sort of automation for answering questions on Twitter

I'll explain as part of tomorrow's exercise why I chose Cold Email for Interesting People over the other ideas.

Actual Progress

Today was more about ideation but I still got a bit done. Again, I had some advanced notice of this challenge to start thinking about what I would make, so I had a few notes that I was able to move and structure into a project document. I made the project folder and initial docs, wrote some TODOs, and figured out the process by which I would work in public.

Meta Observations

Setting up how I want to work in public was more difficult than I initially imagined. I'm balancing three platforms that I want to be relevant on while also wanting to be more continuous and comprehensive than any of the platforms really allow for. I ended up deciding to have this note on my website as the single source of truth and posting snippets from it elsewhere.

Every project I work on has a codename. WfSD was Project Snowball, the application material for Gumroad was Project Giftwrap, and so on. This is called Project Birdhouse. I decided on the codename after I had the topic. Birdhouse because before there was email, there were messenger pigeons, and if you sent a cold pigeon message, the bird would need someplace to warm up. Project codenames don't have to be particularly logical.

One definite issue is that I got started today at 3PM because I worked on other stuff first. I want my work in progress log to be a source of inspiration and answers for other creators who are attempting the challenge, but if I post it at the end of the day it is not as effective. I'll try to work on this earlier in my day.

Special thanks to Adele for today's working music.

DAY 2: Pick Your Topic and Outline Your Product

Day Two requires us to narrow down to a single idea and begin working on it with an outline.

Which Idea?

Yesterday, I highlighted five potential product ideas:

  • Cold Email for Interesting People (the one I'll be doing)
  • Resume Template
  • Reading for Software Developers
  • Hire your First Developer Advocate
  • Some sort of automation for answering questions on Twitter

Let's start with the four that I won't be doing. I might do some or all of them in the future, but I'm not afraid to talk about them publicly because the ideas aren't super valuable, the execution would be.

Resume template. Yesterday, I wrote that a lot of people I know ask for resume help and advice. I've written resumes for half of my friends at this point, always with the same template. I'm not going to turn this into a product for three reasons. First, and most importantly, I don't think I can do better than the existing products out there, and especially not in two weeks. Second, outside my immediate friend group, I'm not recognized as any authority in resume writing. Third, the scope is actually too small for this challenge. A simple template would take a day or so to create because I already have it, and I want to challenge myself to create something more substantial.

Reading for Software Developers. I wrote an entire book about how to create technical content, but there are few resources about how to consume it effectively. This idea is in an area that I have public expertise in and would serve as a clear companion to my first product. However, this idea came down to scope. Even if the book was only five chapters of three thousand words each, that still exceeds the 10% of WfSD upper limit of my scope.

Hire your First Developer Advocate. I envisioned a short guide for CTOs about when and how to hire a developer advocate for their company. There are lots of information on the market about how to become a dev advocate but not a lot about how to hire one. However, I don't have much first-hand knowledge here. I'd have to write this guide from a journalistic perspective, requiring lots of research and interviews, totally blowing out my schedule.

Twitter Automation. I couldn't write a list of product ideas without thinking about a software product. I've been turning over ideas recently for automations that would help people manage influxes of attention on Twitter. Ultimately, this idea isn't well scoped, meaning I'd likely not have anything to launch by the end of the fortnight.

The One I'm Doing: Cold Email for Interesting People. This checks all of the boxes from the spreadsheet:

  • It is a topic that I am interested in (cold email)
  • It applies to a niche market, although I'll have to refine what I mean by interesting people in the product description. The title X for Y is doubly powerful when X is both by Y and to Y. For example, in Writing for Software Developers "for" means both that the book is about how to write as a software developer and how to write to an audience of programmers.
  • I am very excited about the idea
  • I can get a product done in two weeks (less now, as we spent the first day coming up with ideas!)
  • The product idea is challenging, creates value, follows the example, and working on it will give me momentum. Good execution can lead to the launch, the money, and progress of the bet.

While I didn't make the spreadsheet, I know this product would score the highest for the reasons outlined above. Furthermore, I have some demonstrated public credibility on the topic (a screenshot of the cold email that got me my job at Gumroad has been seen over 130,000 times) and I have a good idea of what the topics to cover are.

Action Items: Create your Outline

Outlines are very important to my work. Every blog post, technical article, and chapter of WfSD started with a detailed outline. I find outlines useful for organizing and connecting my ideas.

An outline looks different for everyone. For me, it means detail where I have it and description where I don't. It is mostly about cutting the project into manageable chunks and ordering those chunks for best effect. I can also think about overlying structure and format.

The outline is in markdown, which I use for all writing, but I especially appreciate its flexibility when outlining. I can use different headers to determine how to subdivide my ideas and have lists and tables of information. Then, when it is time to actually start writing, it is easy to copy over and fill in the outline rather than starting from scratch.

Here is the product outline exactly as I wrote it today. I almost guarantee that the finished product will have major differences, but I feel confident it will be easily recognizable as the result of this outline.

The outline has very estimated word counts. These counts are for how long I think the first draft will be and are for planning purposes only. I can write 2K words on an average day, 4K on a good day, 1K on a bad day, so it is important that I keep the total word count of the project down to give myself time for revisions.

# Cold Email for Interesting People

This product is composed of three parts: a short ebook 
describing the main principles of writing a cold email, a 
document showing line-by-line breakdowns of successful cold 
emails that I have sent, and a video series explaining some of 
the deeper concepts behind bothering busy people.

## eBook

The eBook will be organized chronologically along the timeline 
of deciding to send an email through sending it.

### Before you Write (1800 words)

1. Your reason why (just do it) (400 words)
2. Pick the right person **IMPORTANT** (800 words)
3. Where to find contact info (400 words)
4. Timing matters (200 words)

### Write and Send (3800 words)

1. What email address to use (100 words)
2. Format/medium matters (text, call, DM, LinkedIn) (200 words)
3. Personal and well researched **IMPORTANT** (800 words)
4. Specific, unique ask **IMPORTANT** (1600 words)
5. Social proof (400 words)
6. Eliminate back-and-forth (400 words)
7. Shorter (100 words)
8. Signoff (200 words)

### After the Send (1600 words)

1. It is a volume game **IMPORTANT** (800 words)
2. Followups (400 words)
3. Handling rejection (200 words)
4. Delivering on success (200 words)

Other potential topics:

* Avoiding being a spammer
* Laws around email
* Own your email address
* Applying these skills elsewhere
* Psychology of cold contact

It is important to have examples to follow for style. The model 
text for this book is *Rework* by Jason and David of Basecamp.

## Example Email Breakdowns

So this is hopefully going to be some kind of two-column layout,
though I should think about what that would look like on 
various screen sizes. Obviously, I can't publish lots of private
correspondence, but I feel comfortable publishing the first
email from my side of various conversations, especially with
information redacted where appropriate. Some emails, like to one
to Sahil, are already public.

Historical (6)
* First consulting client (client name redacted)
* Query Publisher for WfSD (got a helpful phone call) (publisher name redacted)
* Average outreach for WfSD
* Specialized targeted email for Patio11 for WfSD
* Emails that got me onto Software Engineering Radio (youngest guest ever)
* Email to Sahil to get my current job

It would be cool if, during the course of the challenge, I sent
some more cold emails using my strategies. I might not get
responses, but it would be a good source of more examples, which
could be explained or stand alone as an exercise for readers to
break down. This segment of the second product is a stretch goal.

Potential emails I'd be interested in sending:

* Emails to podcast hosts requesting an appearance on their shows.
* Start interviewing for WfSD second edition (although the book is ~18 months out)
* Recommending WfSD to professors and bootcamps.
* Reaching out to interesting creators and discussing their funnels and monetization strategies.

The model text for this section is the case studies included in Authority, 4th Edition by Nathan Barry.

## Video Course

I'd like to match or exceed Daniel Vassallo's twitter course in length and polish. I'd say that is my model text for this section, although clearly it is not a text.


* Film on my iPhone 8 with my phone tripod and mic
* I have a couple of locations around my mother's house with good lighting, sound, and backdrop
* I'll edit in Final Cut Pro although I might as well be editing in iMovie given my rudimentary skills. Still, it should be enough for decent autocorrection to sound and color, titles, stitching together clips, etc. 
* I'll think about if it is possible to simply export or re-edit the video course as audio for people who want to listen on the go. This is definitely a stretch goal and not central to the main product. If I do that, I might also try to do a reading of the first doc as well.


* Intro & My Story (5 Minutes)
* For Interesting People (10 Minutes)
* Cold Email (10 Minutes)
* Who is providing value? (10 Minutes)
* ... I'd like to think of at least 6 other ten-minute subjects, perhaps taking some advanced topics from the "other potential topics" list above
* Recap (5 Minutes)

The hardest part will be differentiating the content between the
book and the videos and deciding what goes where. I'll
essentially divide it based on how the audience will use them.
If it is mostly inspiration, advice, emotional, and concepts,
I'll put it in the video. If it is reference material, directly
actionable, facts and stats, it goes in the ebook.

Finally, one of today's action items is to post on social media about progress thus far. If you are reading this, then you know I have done so.

Special thanks to Lana Del Rey for today's working music.

DAY 3: Staying on Track

Day Three is where the real work begins. We have a product idea and an outline. There are twelve days left in the challenge. It is time to start drafting major chunks of the product.

I'm planning the product assuming that I have a couple of hours per day to write and document, but knowing my working patterns, schedule, and the scope of the product, I know I will also need a couple of days where I invest large chunks of deep work to make major progress.

Action Items

I wrote the entire todo list for the product. This was only possible because I've created an info product before so I know how I like to do things. Here is the order of tasks for the ebook section:

  1. Topic Sentence Outline
  2. First Draft
  3. Beta Read
  4. Respond to Beta Comments
  5. Second Draft
  6. Developmental Edit
  7. Third Draft
  8. Proofread
  9. Read-Aloud Edit
  10. Formatting

Italic steps are ones that I don't do myself. Ten steps may seem like a lot, but even over a short period of time I'm committed to a certain level of quality and polish for my products. I really wouldn't feel comfortable launching with fewer than three rounds of editing involving at least three people. The steps for the email breakdowns and the videos are similar, although each has fewer rounds of editing than a text document.

You can divide your project as far as you want and map progress at each part. My ebook, even though it will be very short (less than ten thousand words), is divided into chapters, which are themselves divided into segments. As I mentioned in the outline, the model text is Rework, which means I have a good basis for my organizational structure and didn't have to make many decisions. I can track progress on a segment-by-segment basis to make sure I'm getting enough written every day.

I also outlined some basic todos for the product page and launch plan. Fortunately, the 14 day challenge will cover these topics in the daily tasks.

Actual Progress

I put the cart before the horse around lunch to do some early promotion of the product related to a podcast episode that recently launched and tagged me.

On the product itself, I did step 1 for the ebook. I hope to work on it a bit more tonight but I also have to do a bunch of stuff for Gumroad.

Part of today's writing is finding the tone, for which I again turn to my model text. Rework has an informal but informational tone and relies heavily on the second person, but not the first person. I can use as many contractions and bulleted lists as I want. This is similar enough to my default style that it is workable.

Style Sample:

"Hang on," you might think, "the last however-many-pages said that great cold email relies on specificity, research, and customization. Now suddenly it is up to volume?"

The first draft of the ebook is, by word count, 5% done. The ebook is 40% of the project, making the project 2% done. Not great for 3 days in, but the power of a topic sentence outline means I'll be able to turn on the faucet for word count once the ideas have solidified.

Special thanks to Lorde for today's working music.

DAY 4: Creating your Product

Day Four asks participants to think carefully about the format of the product and the tools needed to get there.


Will your product be an ebook or a video course? What is the format of your product?

I described the format on previous days: a short ebook (20-30 pages), six annotated example emails, and a short video course (60-100 minutes).

What is your MVP? An MVP is your minimum viable product.

The video course is important but perhaps not strictly essential to the launch. I could realistically launch the six annotated emails for free as a lead gen and then finish the rest of the product outside of the challenge. But, the ebook is important for discussing exact tactics and the videos are important because there is an emotional side to cold email that is easier to explain with the benefits of facial expressions and speech patterns.

How will you create your product? What applications will you use?

I'm drafting everything in Markdown. For WfSD, I did the layout in Microsoft Word, but I no longer have access to the software because my access was through my college. I could buy a license, and I suppose I will at some point, but the Microsoft word experience wasn't fantastic anyway, and the layout needs of this ebook are simpler. So, I'm going to try Apple pages, mostly because it natively supports exports for PDF and EPUB (and I can do EPUB -> MOBI with Calibre), whereas with Word I exported to PDF but made the EPUB with Pandoc from Markdown. Just trying to make that build process a little easier.

I'm not sure what software I will use to layout the examples as I'm not exactly what the layout will look like. Hopefully I can also use Pages for this.

For video, I'll record with my iPhone, with an external mic. If I have a screenshare component, I'll record that with quicktime. Edits will happen in Final Cut Pro X. It will be very basic, low-budget editing.

Will you outsource some work?

Absolutely. Yesterday's ten steps to write an ebook involved a beta read, a developmental copyedit, and a proofread. Several of my friends will be the beta readers, and my mother will do the copyedit and proofread, just like she did for WfSD. Fortunately, the microwave at my house just died, so my pattern of trading minor appliances for professional editorial support will continue.

Also, my sister has helped me with cover design (spoilers for a future day) and I might get more help from her or another friend when it is time to do design for the cover of each product. I might also need help from someone skilled with layout software for the examples. I also imagine I'll get her help with hair and makeup when it is time to record videos.

Finally, I will rely on the generous help of my professional network and my audience when it is time to launch the product. I imagine I could get a few dozen sales from my own launch efforts but another successful day like WfSD will be entirely contingent on other peoples' interest in the product's success.

Action Items / Actual Progress

In terms of actual progress, working through the questions made me realize the importance of the breakdowns of successful cold emails from my career. Even though it is the smallest part of the product, it is the source of the rest of the insights. Accordingly, I set aside the ebook draft and worked on the examples.

The oldest email in the examples is from February 28, 2019. It was a Thursday, I was bored in class, and I was poking through the internet looking for opportunities. I found a website offering professional services whose business model was interesting, but their copy was grammatically flawed. I didn't think they were a scam site just because of bad copy, so I poked around a bit and discovered that the site had been ported from Russian by founders hoping to expand into the larger English-speaking market. I fired up my email and sent the following message:

Hi [Redacted],

I am an American programmer and writer, and I am currently researching [Redacted]. I came across your site and found it well-designed, but I was put off by the frequent grammatical errors in the text of the main website and FAQ. When I realized that the site was originally in Russian, it made sense, as one of my best friends is Russian, and the errors are similar to those he makes in writing.

I could re-write your information in concise, precise, native English. As a programmer, I would be able to re-write it directly in your code base, meaning you would not have to take the time to integrate these changes. As a student, my rates are low, so this would be a low-cost, low-effort solution for you.

Why does your site need to have its copy re-written? Easy: native English speakers pay a lot of money for services we trust. The cost of the re-write will quickly pay for itself in increased sign-ups from the English side of the site.

Some examples of what I would change:

[Redacted: Sentence written in poor English]


[Redacted: Sentence rewritten in correct English]


[Redacted: Sentence written in poor English]


[Redacted: Sentence rewritten in correct English]

If you are interested, please let me know and we can negotiate a schedule and rates.

Philip Kiely

The founder replied during the same class period, saying that they actually had an English copy rewrite on the roadmap that he was dreading and he would like to have me do it instead, and by the time the class was over we had finished negotiations. This was the first freelance job I ever landed and accordingly had a major early impact on my career. This was not the first message that I wrote looking for a gig, and it was far from the best, but it was the first that worked.

So for the product itself, after giving context like that, I go through line by line and talk about what was good about the email and what was ineffective. For example, in this email I did a good job of demonstrating the value that I provide (although I have to redact it to make the site harder to identify) and directly connecting my work to something the recipient cares about (increased signups from english-speaking users). I also add bits of credibility (American programmer, native english speaker) that highlight my useful intersection of skills. Finally, the personal connection, while very minor, arises naturally and unforced, I really was thinking about my buddy's speech patterns when reading their copy. Downsides of this email is that I undersell my rates (though I was paid very fairly for the work, I recovered later in the negotiation) and the email was longer than it needed to be, it took ten sentences to get to the example fixes.

Hopefully tonight I will return to drafting the ebook and video scripts.

In a slight change of pace, special thanks to John Green's book-signing livestream for today's working background noise.

Day 5: A Compelling Title

So the working title I've been using is Cold Email for Interesting People. This title matches the pattern in Writing for Software Developers; the first half describes the action while the second half can refer to both the actor and the target. In this case, it implies that both the sender and recipient of the email are, broadly defined, interesting people.

I don't have a subtitle for this product because the title itself is long and descriptive. No single other bit of context strikes me as more important than the others. So, rather than elevating any phrase to subtitle, I'll focus on education on the product page.

One of my favorite ways to educate customers is with a FAQ. Now, I've never actually been asked any of the questions on the FAQ because I write it before the product launches. Instead, I anticipate what questions people might have and answer them.

For this product, here are three FAQ entries based on the title. The copy of course would need to be cleaned up a bit before I use these.

What is a cold email?

A cold email is sending an email to someone who you do not know, or do not know well. The "cold" in cold email doesn't refer to the tone (which should generally be warm, friendly, and professional), but rather to the lack of previous relationship.

Am I an interesting person?

I think so! Whether or not someone is interesting is quite situational. For example, Tom Brady wouldn't be interested in hearing from me with ideas for plays to run, but a developer advocate might be interested in hearing from me with ideas for technical content.

Who is this course not for?

This isn't a course about copywriting for mass emails or other bulk outreach. It isn't about generating leads or making tons of LinkedIn connections with some boilerplate message. It is about thinking deeply about how to connect with individuals about mutually interesting things.

Action Items/Actual Progress

I'm exactly where you don't want to be in a short challenge like this one: behind. I'm going to need to make serious progress over the weekend when I have fewer work responsibilities to get back on track. The later half of the production process depends on other peoples' timelines, so I need to leave time for that as well.

I was talking to someone today who I met on the internet and the product I'm working on came up during the conversation. I got a better sense of the correct place to divide the content between the ebook and the videos. We also talked about how some of the value of the product is in encouragement.

Special thanks to Ariana Grande (new album) for today's working music.

DAY 6: Covering Images

Day Six asks participants to create a cover image for the product. I have a rough sketch and some assets selected but haven't actually made the graphics yet, that will come later in the project.

Cover Sketch

The cover image is horizontal so it doesn't take up too much room on the Gumroad product page and will include a representative image of each of the three parts of the product, along with the product's title and the PK&C logo.

Actual Progress

If you get stuck, lower your standards and keep going.

The six examples are all set up and resolved, in about 2k words without the emails or footnotes. They will definitely need some serious editing in the next week but at least they exist.

Sample (context, not emails yet, stay tuned!)

## A Standing Invitation

I have been a Patrick McKenzie fan for years. When I first imagined adding interviews to Writing for Software Developers, his name was at the top of the list. However, I didn't email him first. I asked him near the end of the process, when I was more confident in my skills and chances. However, due to the high volume of email he received, I knew I would have to do something special to stand out.

One thing that McKenzie and I have in common is that we are attentive readers of Matt Levine's newsletter, Money Stuff. Levine was one of the first people who I interviewed for the project. So, I knew I had a useful bit of social proof to pique his interest. 

McKenzie maintains a [Standing Invitation]( on his website. It is extremely helpful when the person you want to contact provides explicit instructions on how to do so. However, there was a single line from the document that had em worried: "I don’t like telephones. If you want to speak to me by telephone, marry a McKenzie." I hoped that there was an exception for interviews (rather than sales calls or individual questions) but that was a major roadblock to overcome in the message.


As luck would have it, McKenzie was available, interested in the interview, and a fantastic source of information for the book. He also amplified my launch efforts, materially boosting sales. His help was absolutely worth the personalized effort, and even worth the sighs and eye rolling from my friends as they put up with a solid week of fanboy glee after the interview.


When I had an outline and a plan for Writing for Software Developers, I did what I thought you are supposed to do: I looked around for a publisher. I'd already read *Authority* several times, so I knew that self-publishing was an attractive possibility, but I figured that a traditional publisher would lead to a more successful book. I picked my first choice of publisher and sent them a query and follow-up. While these emails didn't land me a book deal, they impressed the executive editor enough that they scheduled a long phone call to answer some of my questions about the publishing call, a rare gift from a very busy person.


Even though this email failed at its primary objective, I'm including it because I got something far more valuable. After the conversation, I had a clear understanding of the steps that a traditional publisher would take to ready a manuscript for publication. Thus, I was able to confidently self-publish knowing that I was following the same steps as the pros. Like most successful self-published authors, I most likely made far more in revenue from my own launch than I would have in royalties with a publisher, and I certainly wouldn't have my current job if I'd convinced a publisher to take my book. Cold email can lead to serendipitous unknowns, opportunities that you didn't even know existed.

I spent way too long (more than 2 hours) trying to get the layout of the document to work in a two-column format before realizing that said format would be unreadable on a phone or other small screen, and that footnotes would do the job just as well. These are the kind of detours that you really can't afford when working on a time-boxed project. Eventually, a friend snapped me out of it by reminding me that CSS exists and I know how to use it, so I can try the formatting again later with code instead of an application if I want.

Special thanks to Fall Out Boy for today's working music.

DAY 7: Build an Audience

You can't just post a product on the internet and hope people find it. The more audience building you do before launch day, the less work and more fun launch day is.

I'm just not ready. I absolutely agree that this is the stage where I should be putting together a landing page, collecting emails, and beginning to drum up hype for the launch. I'm far enough behind on the product itself that I have pushed my projected launch date from Tuesday Nov 10 to Thursday Nov 12. Even with that, I have to spend my energy on creating the product itself. In a perfect world, I'd do everything at the right time. Sometimes you don't get everything done and you hope the launch is successful anyway.

Fortunately, this is my second product, so I have a small audience already built up. I hope that people with larger audiences choose to share the product, and I think the best way to improve the chances of that happening is to focus on creating the best possible product (because I already have a small audience and a personal/professional relationship with the people I'd ask to amplify) which is an advantage many creators don't have but to succeed as a creator you have to use all of your advantages.

When I am ready to build an audience for this product in particular, I'll give away something valuable for free. The most valuable thing I have is my time, and I imagine that I will, probably Nov 5 but possibly over the following weekend, give my time away by inviting people to send me cold emails that they are considering sending to other people for me to give feedback and encouragement on.

Actual Progress

The Six Annotated Examples are drafted at 7400 words, counting the length of the original emails themselves. Three of the examples actually are a pair of emails, so there are nine primary sources. Still figuring out exactly what to call that component.

Will focus on the ebook component tomorrow and use Tuesday as a beta reading day because I am working 6AM to 10PM at the polls in Iowa.

Special thanks to ERB for today's working music.

DAY 8: Pricing

Ah, pricing. It is a hard issue. I seem to have hit the mark on Wrtiting for Software Developers, people called it underpriced (which you want, your customers should feel like they are getting good value for their money) even though $36 was a decent premium over the 25-to-30 dollar average price of similar books. I also had a single, simple tier, a 100-dollar extra charge for a corporate license. Fifteen sales at this tier netted fifteen hundred dollars of bonus revenue.

For this product, I have to start from scratch. There are a few different pricing models to consider: fixed price, fixed price increasing, variable price minimum, and variable price no minimum. Each pricing model could be further complicated with tiers. The product I'm creating has three components, meaning I could have one, two, or three tiers, depending on how fancy I want to get. Here is the breakdown:

  • Fixed Price: The simplest model. I charge $X for the product. With tiers, I charge $X, $Y, and possibly $Z for various components of the product.
  • Pros: Easy for the customer to understand, lots of control
  • Cons: Have to pick a price
  • Fixed Price Increasing: Similar to fixed price, but I start the price low and raise it after every N sales until I reach some final price.
  • Pros: Reward early supporters, give a sense of urgency
  • Cons: Extra work, still have to pick a price
  • Variable Price Minimum: Let customers pay what they want with a minimum price. For tiers, the minimum price per tier can vary.
  • Pros: Price discrimination, guaranteed minimum value per sale
  • Cons: Suggested and minimum prices anchor customers, negating some flexible pricing benefits
  • Variable Price No Minimum: Let customers pay what they want or download for free. With tiers, some tiers could have a minimum price.
  • Pros: Simple, perfect price discrimination, market discovery
  • Cons: People might just download for free, makes tiers complicated (as having min price tiers puts price anchoring and decision making back in the mix)

For this product, because it is relatively small, even with the multiple components I don't think it is a good fit for tiers. After a lot of thought, I've decided on variable price no minimum without tiers. If I was spending 6 months on this project, I'd do fixed price with tiers, which if done right is the best pricing strategy, but I'm willing to take a risk with this product because of the relatively small time investment behind it. Besides, I can always change the pricing strategy later.

Let's go through the pros and cons of the strategy that I've selected. First, pay-what-you-want is simple, both for me and the customer. More importantly, it leads to perfect price discrimination. Rather than trying to use tiers to estimate each customer's willingness to pay, they let me know exactly what that number is. Finally, rather than having to guess what price the market might support, I'll get valuable data from people telling me what they think the product is worth.

Addressing the cons, they actually aren't a big deal. Sure, people can get the product for free, but they can do that with WfSD too (either through the refund policy or the free copy upon request policy). Plus, free distribution will increase my audience size and reach. The product is too small to really benefit from tiers, all three components work together to complete the experience. Again, with more time I'd do tiers, but its ok to launch things that aren't optimized.

This pricing strategy is a big risk. But, I have a key insight that makes me more willing to try the experiment. Gumroad used the pay what you want feature to launch this 14 day challenge. Despite it being offered by Gumroad, not an independent creator, and the product page explicitly saying the product was free, almost ten percent of participants chose to pay for it. (I offered those people refunds and we will be giving the remaining funds away.) This gives me confidence that if I ask people to pay, they will, and generously.

While I've spent a few hundred words talking about how I'll avoid price anchoring, I do plan to include some suggested prices buried deep in the FAQ to help indecisive customers make a purchase, any purchase.

Actual Progress

Today I'll be working on the ebook and video scripts.

Special thanks to Taylor Swift for today's working music.

DAY 9: Break

I was a poll worker from 6AM to 10PM.

At times when it was slow, I did various things, including occasionally noting down ideas for CEfIP.

CEfIP poll notes

DAY 10: Formatting and Editing

As you've seen in previous updates, I wasted tons of time on formatting and went for a more basic look. The editorial process hasn't started yet.

Today was a catch-up day at work because I missed yesterday as I was working the polls. At this point, I'm doing the days a bit out of order, but I'll be back on track tomorrow with a sales page (for collecting emails).

DAY 11: Creating a Sales Page

I could talk for hours about sales pages, but instead, I always tell people to copy WfSD. For this challenge, I took my own advice. I know that the WfSD sales page is effective, converts well, and is based on optimized pages with proven success. Also, the code is already written.

Sales copy is some of the hardest writing around. You have to be laser-focused on your audience, and the market for this product is broader than my first one, so that was difficult. I don't think the copy is particularly finalized, and the page will be modified for the actual launch. The landing page will evolve into the sales page.

Here is the page.

What is a pain point that your customer has?

They are in the same situation I was in a couple of years ago: they have something big that they want to accomplish, they have been working hard on their own, but they need access to people and resources, opportunities and ideas that aren't available to them. They need to expand their network in meaningful ways.

What will your product do for them?

My product will teach people how to formulate a specific and effective cold email. It will teach them who to write to, how to find them, and what to say. Some of the advice will be a bit counterintuitive, some will go against traditional wisdom, but all of it is hard-earned and worked on my machine.

Why should they buy from you?

Early on, I don't have any testimonials for the product itself, but I got permission from Sahil to use one of his tweets, which is a bit of social proof to people familiar with my story. The product itself has social proof built in with annotated examples, and free samples will build credibility (of course, the whole product can be had for free as well)

Tell them exactly what they’ll get if they purchase a copy.

My presale page is collecting email addresses rather than pre-orders. I tell people that I will notify them on release day. I also let them know that this is a general email address collection field but they will receive at most one email per month and the emails are easy to unsubscribe from but I don't know why you would because the emails are packed with value.

I also describe the product itself, but the descriptions will be much longer on the actual product page. I will set up a Gumroad product page when I'm ready to actually start selling.

Actual Progress

I filmed what will be, after editing, at least 15, possibly 20 minutes of video.

Special thanks to 2Cellos for today's working music.

DAY 12: Launch Plan

Planning a launch is a lot of fun. It is easy to let your imagination run wild, thinking about views and upvotes, sales and retweets. This can be useful as motivation, but it is also easy enough to get distracted. Have a solid, simple plan, and then execute.

Writing for Software Developers launched about six months ago and did better than expected. Two things that made it work:

  1. A clear value prop precisely communicated to a large but niche audience on a concentrated platform (Hacker News)
  2. Public support and signal boost from prominent members of an online community (Indie Tech Twitter)

So even though I didn't do a bunch of stuff that usually helps with launching like building a mailing list, accepting preorders, building an audience, and so forth, I was able to borrow credibility to launch (and the lenders got a strong return on investment). So, after that success, it is reasonable for me to want to run the exact same playbook again. For the most part, I'm doing that, but there are slight adjustments because the product is different, I have a small audience to launch to, and I have a stronger network to access.

Before the Launch

Nov 5: landing page to collect emails built. (done)

Nov 6: post on twitter inviting people to send me cold emails to beta read before they send them to the final recipient. Spread landing page along with the message. Basically, give away something valuable for free to raise awareness. It is the sprint version, the midnight cram session version, the 2-minute drill version of audience building. I'll probably run another one after the launch.

Launch Day

This is where the money is made. November 12th, 2020, starting 9AM EST and ramping up around Noon. Prime time but might as well compete in the heavyweight division. Only Tuesday at the same time slot is more contested, and Tuesday the 10th has an Apple event that I don't really want to compete with.


  • Email to every Gumroad follower (from landing page)
  • Email to everyone who bought WfSD (pitching it more as a freebee)
  • Individual emails to people who I know


  • Show HN post. Probably not going to do as well as WfSD as it is for a different audience but the HN dice are always worth rolling. Run the exact same play as I did six months ago.
  • Product Hunt. Last time I launched on PH and HN with HN as the focus. This time, I'll be directing people to talk about the product on PH over HN as I think the content fits that audience better. Getting into the PH newsletter is the pipe dream.
  • Indie Hackers. I'll definitely be launching here, there are a few people on the platform who I have good relations with and hopefully they will see it there.
  • Circle. I will of course post to the appropriate channel in Gumroad's community (currently in private beta)

Social Media:

  • Twitter. I will post, and this is where I hope to make the most sales. I have a small but decently engaged following on Twitter. Really, I'm once again banking on signal boosts. They will be from a different group than WfSD, but if the people I have penciled in as "they will see this and choose to retweet" combine to about 100X my following and the reach group beyond that doubles the previous amount. Of course, if people choose not to signal boost it, which is entirely possible and no hard feelings whatsoever if that is the case, then this channel will be less effective.
  • LinkedIn. WfSD went straight nowhere on LinkedIn, but I also have a relatively small group of connections there (~600) and it is not a very developer-heavy group. A more general product like CEfIP has the potential to do better on LinkedIn.


  • My baseline expectation for launch day is 5000 views, 250 total downloads, of which 50 are purchases. I'll be disappointed in myself if I don't achieve that and will have to seriously re-evaluate my strategy. My middle-of-the-road goal is to double each of those numbers, and my reach goal is to double them again.

After the Launch

After the launch I'll focus on content to promote the product. I'll write some nice cold emails to podcast hosts to see if I can get on some shows. I'll open up the product to affiliates a couple of weeks after launch. I'll post some interesting threads on twitter and probably repeat the beta-read cold email offer.

I also have five pieces of blog content I'm planning for. Each will connect to cold email in some way, and two explicitly about the product (launch retro and 14 day challenge summary) while three others are tangential (working in public, something called The Acolyte's Manifesto, and publishing my business plan publicly). Promoting each of these pieces of content is like a mini launch day for the product.

If there is something I've learned about sustaining sales, it is that smooth sales and a bunch of little spikes hit the bank account the same.


Today is all about that handbook. Word count, run up the score.

Special thanks to Jay Z for today's working music.

DAY 13: Last Minute Tips

Sent the annotated examples into editing. Went to edit video but realized I need to reshoot all of it due to low quality. Launch date uncertain. Will try again tomorrow.

I did find a great analogy for the different parts of the product. The handbook is the recipe. The video course is the cookbook explaining ingredients and key skills. The annotated examples are the episodes of The Great British Baking Show. They are all useful at different stages but ultimately only you can bake the cake.

4 full days until launch. I'm feeling really good about the annotated examples and not nearly as good about anything else.

DAY 14: Are you ready to launch?

Ha, nope!

But hopefully I will be on Thursday morning!

Everyone needs an editor. Here is a screenshot of one page worth of edits on the most recent draft of the six annotated examples.

6AE WIP screenshot

This is the last daily update you'll see on here for a few days, I'll update on launch day and afterwards with a retrospective.

Day 18: Launch!

I launched Cold Email for Interesting People at 8AM central time on Thursday, November 12th, 2020.