207: ‘Christmas Mitzvah’ With Merlin Mann

Episode Summary

Executive Summary: The conversation centers on the durability of Markdown and the tooling/workflows that support writing, while branching into platform preferences, productivity automation, and a long political detour about Trump, prediction markets, and post-2016 disillusionment. The hosts argue that good tools should be simple, trustworthy, and adaptable, and that the same principles apply to text editors, laptops, note apps, and even political systems.

Main Topics: Markdown’s origin, evolution, and design philosophy (Priority: 5/5): The speakers revisit how Markdown emerged from dissatisfaction with raw HTML, its influences (Textile, Setext, ATX, reStructuredText), Aaron Swartz’s contributions, and the deliberate choice to keep Markdown simple, permissive, and human-friendly rather than rigidly machine-valid. Text-editing workflows and app ecosystems (Priority: 5/5): They compare Drafts, Editorial, NVAlt, Vesper, Yojimbo, Apple Notes, TextMate, and other tools, emphasizing speed, sync reliability, markdown support, and how different apps fit different kinds of content and devices. Automation and customization on the Mac (Priority: 4/5): Keyboard Maestro is presented as a way to build custom features and app-specific shortcuts, including a practical macro to route Twitter replies from the correct account without bothering developers. Device preferences, keyboards, and platform culture (Priority: 4/5): The discussion contrasts Macs, iPads, Chromebooks, Steam/Windows-style apps, and the changing meaning of being an 'Apple person.' Much of it is about how UI conventions, keyboard layouts, and app styles signal whether a tool feels native or alien. Networking, travel gear, and sponsor ads as product demos (Priority: 3/5): Sponsored segments for Away, Fracture, and Eero are woven into the show as concrete examples of useful consumer products, with detailed praise for their design, reliability, and convenience. Politics, Trump, and prediction markets (Priority: 5/5): The latter part of the episode turns to the 2016 election aftermath, the logic of prediction markets, the limits of polling, and growing alarm about misinformation, authoritarian behavior, and institutional failure under Trump.

Key Arguments: Markdown succeeded because it trusted writers to be sane and prioritized readability and portability over strict formalism. Aaron Swartz was central to Markdown’s early adoption and improvement, even if he was not the sole creator; the origin story is partly distorted by later retellings. Good software should minimize friction and let users act directly; if an app or OS forces unnatural workflows, people will avoid it or work around it. Custom automation is often better than pleading with developers for niche features, as shown by the Tweetbot/Keyboard Maestro reply-account workaround. Reliability matters more than novelty in note-taking and syncing apps; losing data is treated as a deal-breaker. A lot of modern UI pain comes from apps that ignore native platform conventions, especially Mac apps that behave like web or iOS apps. The political system is vulnerable because it assumes good-faith actors; Trump exploits that weakness and has normalized lying, corruption, and bad-faith power games. Prediction markets are useful because they synthesize information better than gut reactions or partisan wishful thinking, but people still misunderstand probability. The 2016 election felt different from ordinary partisan losses because it seemed to threaten the underlying reality-checking function of institutions, not just a policy outcome.

Data Points: Markdown public beta timing: March 2004 - Referenced as the point when Markdown was publicly released after months of private iteration First Markdown post in Movable Type: October 2003 - John Gruber described when he first switched Daring Fireball posts from raw HTML to Markdown Annual episode output: around 40 episodes/year - Used to describe the Talk Show’s typical output Episode number: 31st of 2017 - Referenced while discussing the show’s publication cadence Tweet accounts used: 3 main accounts - @Gruber, @DaringFireball, and @TheTalkShow PredictIt return on Trump: roughly 5x to 6x on some shares - He bought Trump contracts around 18% and eventually collected $1 per share at settlement Starting and ending wager size: a few hundred dollars to about $1,500-$1,600 - He described turning a small stake into a larger sum during the primaries before losing it on the general election Market odds cited for Trump at year end 2017: 95% yes / 5% no - PredictIt market status discussed near the end Market odds cited for Trump at year end 2018: 68% yes / 32% no - PredictIt market status discussed near the end Market odds cited for Trump in 2020 presidential winner market: 65 cents for no on Trump - PredictIt pricing discussed as a possible value bet Typical iPhone app storage/workflow note: 2600 text files - Referenced while discussing file syncing and text-file organization Holiday sponsor warning: third episode in a row - Fracture was described as having sponsored three consecutive episodes

Pivotal Quotes: "I don't want to know if somebody's having Typhoon. This is not part of the show because talking about Skype is like, it's like the college newspaper columnist writing about writing a college newspaper column." — John Gruber: Opening complaint about Skype and the discomfort of communications tools becoming social/ad-tech products "The secret to Markdown and the thing that drove people nuts at the beginning ... is that it trusts you, the person typing the markdown, to be to type sane markdown." — John Gruber: Core explanation of Markdown’s philosophy and why it became popular "I am apparently not the only person in this condition, but I have a Dropbox folder called Elements" — Merlin Mann: Discussing text-file organization, syncing, and long-term editor/workflow habits

Implications: The episode frames good software as simple, durable, and user-trusting, while warning that sloppy UI, brittle sync, and bad-faith politics can erode trust. Listeners are encouraged to automate thoughtfully, choose stable tools, and stay alert to institutional decay and misinformation.