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Jul 7, 2025
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  1. 002 - Dilemma Round One Results
    Jul 7, 2025 · original
    But first, some context The way this tournament is set up is kind of funny. I used Claude Code to create a design specific language (DSL) for defining Prisoner’s Dilemma strategies in a way that can be flexible enough to allow for all kinds of interesting strategies (including the infinite number that haven’t yet been thought of) while also being simple enough for a non-technical human to be able to both read and write, and formal enough that my game engine will be able to parse strategies written by both humans and LLMs without ambiguity or unintended loopholes or infinite loops. Timeline of events: June 18th: Idea is planted. Helped someone vibe-code the beginnings of a game with Claude and Cursor, and was reminded of this team-based iterated prisoner’s dilemma game I had sitting in a repo somewhere with lots of notes about how it could become a game if I had more time and brain power
  2. 001 - Dilemma Pregame Commentary
    Jul 6, 2025 · original
    I’m playing around with different ways of presenting the results of this tournament. I’ve never really played around with podcast tools, so this is my first foray, and so you’re gonna cringe at the short-cuts I’m taking here. I’m using Riverside.fm, Google Notebook LLM, and suno.com for the intro beeps and boops. I don’t know how to make the transcripts and show notes look nice. This short episode goes into the pregame commentary, summarizing how Prisoner’s Dilemma works, how this team-based version with AI teams vs a human team will help us discover even more interesting things about collaboration and competition, and they also try to predict how things will go in the first round. If you listen, let me know what you think and if you have suggestions for how I can prompt Notebook LLM (or another AI) to be better.
  3. Dilemma Tournament: Team Introductions!
    Jun 26, 2025 · original
    Context: I’m running a team-based iterated prisoner’s dilemma tournament that has 4 teams with 5 players each. The teams are run by ChatGPT, Claude, Gemini, and us humans. Details about the game and how this tournament will run are here. Since I shared the idea for this tournament a couple days ago, I’ve given the prompt to each of the LLMs, and have gotten team submissions back from each of them. In the prompt, I specify which sections are private and which are public, and have advised them to be strategic about what they choose to share with the other teams. Here are the public sections of each team’s submissions (also archived here): Team ChatGPT: The Hydra Coalition Team Philosophy: “Many heads, one allegiance; betray one, face us all.” Team Battle Cry: “Cut off one head… two more shall rise!” Team Description: The Hydra Coalition unites five cunning minds as one, ready to cooperate
  4. Wanna play an iterated prisoner's dilemma tournament between ChatGPT, Claude, Gemini, and humans?
    Jun 22, 2025 · original
    If you’re unfamiliar with Prisoner’s Dilemma or feel like you need a refresher, this video from Veritasium from last year does a good job of introducing the game, as well as explaining why I think it’s such an interesting little microcosm of how we behave in the world and a game that is capable of teaching us so much: I’ve hosted a few “team-based iterated prisoner’s dilemma” games on Facebook over the years. There are usually 15-25 people split up into two to four teams, and the goal is for the people to discuss ways to beat the other team in a round-robin style format where every player is matched up with every player on the other teams. So if Team Ant has 5 people and Team Beetle has 5 people, then everyone on Team Ant plays 100 matches against everyone on Team Beetle and vice versa. If there’s also a Team Caterpillar, then everyone on each team plays everyone on each of the other tea
  5. What are your beliefs about the nature of reality? V2
    Apr 15, 2025 · original
    What are your beliefs about the nature of reality? This interview is designed to be a fun way to help you identify your fundamental beliefs about the nature of reality (aka your cosmology), and attempts to get kind of specific about it. It’s not meant to be a comprehensive survey of all possible cosmologies, but rather a tool to help you identify your own cosmology and perhaps to spark a fun conversation with others. STEP 1: Identify your beliefs about the nature of reality at a high level Start at Question 1 . Follow the instructions after each answer until you reach your initial cosmology. Then proceed to Step 2 to refine your result. 1. WHAT IS REALITY? At the most fundamental level, which of these best describes your view? Reality is primarily ruled by spiritual or divine powers → go to Q2: WHO CREATED IT? Reality is primarily ruled by physical or material laws → go to Q5: HOW DOES I
  6. What are your beliefs about the nature of reality?
    Mar 18, 2025 · original
    This short interview is designed to be a fun way to help you identify your fundamental beliefs about the nature of reality (aka your cosmology), and attempts to get kind of specific about it. It’s not meant to be a comprehensive survey of all possible cosmologies, but rather a tool to help you identify your own cosmology and perhaps to spark a fun conversation with others. STEP 1: Identify your beliefs about the nature of reality at a high level Start at Question 1 . Follow the instructions after each answer until you reach your initial cosmology. Then proceed to Step 2 to refine your result. 1. Which statement best captures your beliefs about the fundamental nature of reality? Reality is the creation of one supreme being → go to Question 2 . Reality involves the interaction of multiple gods or spiritual entities → go to Question 3 . Reality, God, the supreme being, Source, the universe,
  7. November update!
    Dec 9, 2024 · original
    It’s now been 2 months since I set out to work full-time on 750 Words for 9 months and try to make it something that could sustain permanent full-time work. October’s report is here. The goal remains: to find a way to grow from ~4,500 paying members to 8,500 before the summer of 2025. To do this in a way that keeps 750 Words feeling simple, non-annoying, and focused on helping people more than making money. Here’s how that’s going! Member Growth: We started the month with 4,656 paying members and ended the month with 4,821, which means we gained 165 new paying members (up from 31 in October). Our goal was 250, but we’re still ramping up our efforts and haven’t done any actual marketing yet. Most of this is attributed to actually enforcing the end of the free trial (oops, we weren’t doing that before) and asking people to become members after 30 days is up. I’m happy with this level of gr
  8. I analyzed 15 years of testimonials from users of 750words.com to learn how their private journaling habits have helped them
    Dec 3, 2024 · original
    Cue movie trailer voice, “In a land before time…” Hm, that’s not quite right. Okay, got it. Cue scratchy old man’s voice, “Four score minus 25 years ago today, when I was but a wee lad…” That’s too derivative, damn it. I guess I gotta just be me, BBB. Okay, well, this coming December 16th, a little website called 750words.com is gonna turn 15 years old. It was inspired by the idea of morning pages in Julia Cameron’s The Artist’s Way, but online and with lots of silly stats and animal badges. While reading testimonials I came across this description of the site from a long-time member back in 2017 when she was only about a month in, and I thought it captured the spirit of things really well: “750words.com is very dynamic and tailorable with plenty of reward systems (badges, challenges, acknowledgment of word goal achievement, etc) and ways to engage in a social capacity while still having
  9. October report! Month one of this experiment in sustainability
    Nov 13, 2024 · original
    It’s been a little over a month since I quit my job and decided to work on 750 Words full time for about 6 months (or however long my portioned savings last). The experiment is to see if it might be possible to survive without getting another job in tech for even longer than that, because working on this would be so much more fulfilling and fun. The goal remains: to find a way to grow from ~4,500 paying members to 8,500 before the summer of 2025. To do this in a way that keeps 750 Words feeling simple, non-annoying, and focused on helping people more than making money. Here’s what happened in the last month in terms of the goal: Member Growth: We started the month with 4,620 paying members and ended the month with 4,656, which means we gained 36 paying members in the month. This is a slight increase from the 31 paying members we gained in September (16% increase). Not much but at least i
  10. A new way to share stats
    Oct 24, 2024 · original
    If you go to your stats page after writing 750 words you should now see a new button that starts off by saying “Stats sharing is OFF”. Like this: If you click that button, you will be given an opportunity to configure your sharing preferences. One of the main things that I never want to change about 750 Words is that the writing is private. So for now the sharing feature will always be turned off by default, and will have to be turned on explicitly for every entry. The idea being that the only time you need to turn sharing on is when you explicitly want to send stats for a specific entry. I don’t want things to be shared automatically, and for now I’m also leaving out word clouds from the things that you can share (let me know if you feel strongly about wanting to share word clouds and I might re-consider… the old 750 site did allow it after all). When you turn stats sharing on for an en
  11. Want to help 750 Words become sustainable?
    Oct 18, 2024 · original
    This is a bit weird to write, but here goes. I left my lovely job at Medium a couple weeks ago to try something kinda crazy. Between now and the summer of 2025 (the next 6-9 months), I’m going to be working hard to try to grow 750 Words enough so I can work on the site full-time in a sustainable way (it currently requires dipping deeply into savings, hence the kinda crazy part, but also a very fortunate opportunity to have). 750 Words turns 15 years old in December, and it’s a project that I have always felt inspired and delighted by because it seems to just work, and there are so many stories from people about how private journaling has helped lives in meaningful ways. I cannot express how great it would be to be able to dedicate all my time to increasing that impact—there are a bunch of ideas piled up over the last 15 years that are dying to become real! Over the next 6-9 months we’re
  12. 48 — Be Buster Benson, BBB, Be Be Be, 🐝🐝🐝
    Oct 10, 2024 · original
    Wow, it’s October. For the last 18 years I’ve reviewed my life and posted an annual review around my birthday in May, and have done so for the most part rather promptly. Here I am over 4 whole months later, starting maybe my 10th draft of this damned thing, still at a complete loss for words around how to talk about what is happening in my life. To be honest, I haven’t had much luck talking about my life for 5 or 6 years… maybe since I burned out on tech and publishing during and after the release of my book in 2019. The pandemic came as a relief at the beginning of 2020, I remember, in that twisted way that some introverts and burnouts were able to guiltily confess in private messages to one another at the time. Despite the upheaval to the world and our lives, we all suddenly had bigger problems to fry / better excuses to provide for why self-expression, personal branding, and social ne
  13. New Partner Program incentives focus on high-quality human writing
    Jul 18, 2023
  14. New experimental feature: the Streak Fairy
    Jun 11, 2023 · original
    We rolled out a new little feature that has been in testing for a few weeks and could really change the way 750 works. For that reason we’re not gonna fully commit to making it a permanent feature yet, but would love for people to try it and let us know what you think. The gist of it is that if you miss a day and break your streak, you will have 7 days to make up for the missed day with a “double” day (1,500 words instead of 750). When you do, a little fairy will pop up (where the little pop up usually shows up when you hit 750 words) and offer to repair the day that was missed. If multiple days have been missed within the week, it’ll offer this on the oldest of the missed days, and let you slowly patch it forward until the full gap is covered. This is a way to fix streaks that doesn’t require a streak patch and doesn’t require writing in to support and making your case, and yet still (i
  15. 47 — CHALANT! ☄️
    May 31, 2023 · original
    I’ve written an annual review every year for the last 17 years, and they’re getting weirder. This one is no exception! Here we go. I was about to start this review by talking about a thing I realized in therapy recently, until I read my review from last year and could see that I was talking about it back then too. Here it is anyway. Recently (aka over the last year or two), I’ve realized that my default solution to every personal challenge in life has been to craft a better mask. I think of masks as personality constructs that we can put on and use as an identity accessory that helps us fit in, avoid discomfort, reduce insecurity, get things done, etc. Perhaps you are familiar with these masks I speak of? Hmmm… 🤔 I can pinpoint specific moments in my childhood where the experience of being my whole, authentic, undefended self was super confusing and painful. Because it was just the way
  16. A Quirky Clock That Doesn’t Track Time
    Dec 12, 2022
  17. A Big Linky Map of Medium
    Dec 7, 2022
  18. How To Coach Yourself
    Oct 24, 2022
  19. Ideas I'm Mulling
    Jul 5, 2022
  20. Blog about ideas I'm mulling
    Jul 5, 2022

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