When John Gruber first started writing Daring Fireball in 2002, he was just one man with a computer and a lot of opinions about Apple products.

Today, over 20 years later, Gruber is still one man with a computer — and plenty of opinions — but his decades of prolific, perceptive, and pithy writing have firmly established Daring Fireball as one of the internet’s eminent sources for information on the world’s most valuable company.

His influence extends far beyond his writing. In 2004, Gruber released Markdown, a coding language for writers that’s become widely-adopted by some of the internet’s most prominent platforms.

John Gruber has been able to shine as a writer thanks to his pioneering experiments with monetizing Daring Fireball (explored in detail below as a free sample of Gold’s Guide Advance). After much iteration, Gruber ended up on his now-staple weekly sponsorship model, with one sponsor featured per week.

Because he only accepts sponsorships from products he would actually use, readers have a unique sense of trust in the sponsors that appear on Daring Fireball.

Compared to the absolute deluge of ads that I’m inundated with on most websites, Daring Fireball’s thoughtful and minimal ads stand out as being actually memorable. The simplicity of this business model is strikingly effective, and I’ve bought many of the products myself.

Compared to other websites — which are mired in a swamp of display ads, chumboxes, and pop-ups — Daring Fireball feels like a breath of fresh air.

Ironically, the fact that there haven’t been any major redesigns or updates to Daring Fireball is an innovation in-and-of-itself.

Throughout it all, Daring Fireball has remained virtually the same, like a lighthouse standing tall amongst the tumultuous, ever-changing tide.

On the surface, Daring Fireball is about Apple, design, and technology — but if you ask me, it’s really a living documentation of one man’s personal definition of excellence.

HTML undergirds the entire internet, but it’s also incredibly frustrating to read and write it as code.

That’s why in 2004, John invented Markdown, an easier-to-read and easier-to-write text format that cleanly converts to HTML and is one of the most popular syntax languages on the internet.

Markdown has become widely adopted as the internet’s default file format for prose, aka text that isn’t code. It’s even spawned multiple variations that attempt to improve or standardize the original principles.

If there’s one thing (besides SaaS business models) that mainstream enterprise apps like Slack, Notion, and Github share in common with open source publishing platforms like Wordpress and Ghost — it’s that they all support Markdown.

Despite its ubiquity, because Markdown was released under an open source license, Gruber hasn’t earned a single penny from the product. This “I made it simply because I wanted it to exist” sentiment is increasingly elusive on the modern internet.

Table of Contents

Products | Content Analysis

Origin Story | Understanding Apple

Competitive Advantages

Products

Content is published on Daring Fireball in two text formats:

1. Full articles — columns that can range anywhere between a few hundred and 5,000 or more words, usually consisting of sagacious opinions on recent news or in-depth reviews of the latest Apple products.
2. Linked list — brief remarks on content from across the internet. The headline links out to the source material, usually with a short quote or a quippy remark. Sometimes, the quip is the quote itself.

Longer articles reviewing or editorializing on Apple products or the company’s broader business strategy are the main attraction, but Gruber only publishes long-form columns only when he has something to say (or when a new Apple device is released).

Linked list posts are prolific and cover everything from Gruber’s interests in martinis to Star Wars to the latest tech meme of the week.

The Daring Fireball website is self-hosted in classical open source fashion. While Gruber frequently advertises all-in-one publishing platforms like Squarespace, he has always controlled his tech platform, using Linode for hosting and the venerable Movable Type as his CMS.

Gruber hosts two podcasts:

• The Talk Show is 3x-monthly long-form conversation with tech reporters and app developers. The podcast was previously co-hosted with Dan Benjamin, but Gruber has been hosting the show himself since 2012.
• Dithering is a paid podcast co-hosted with Stratechery founder Ben Thompson that publishes two episodes per week about the latest news in tech. Each episode is exactly 15 minutes in duration, “not a minute more, not a minute less.”

Content Analysis

As emphasized by the site’s minimal design, Gruber’s main focus is on his writing. As of the 14th of December 2023, Daring Fireball had approximately 1,560 articles listed in its Archives.

When we sum-up and plot everything out on a chart by month, we can see a noticeable downtrend in output between 2011 and 2016, which seems to have coincided with a surgery that Gruber underwent in 2015. For reference, the iPhone 6s was released in September 2015. Output picked back up again in 2016.

September is the most popular month for new content on Daring Fireball — not surprising considering that’s when Apple releases new iPhones.