Chappy's POM

I wrote this for anyone who works, builds, or spends a lot of time with me! I can be intense, direct, opinionated, and extremely systems-oriented. At my best, those traits make me a great collaborator; at their worst, I can be a lot 😅. This is my attempt to make it all explicit: how to get the best out of working with me, where I tend to get in my own way, and what you should expect from me in return. Definitely a living doc, so if your actual experience conflicts with anything here, please trust your experience and tell me so I can improve!

chappyasel.com
Last updated September 2026

TL;DR

  • My personality tests say I’m extreme in almost every direction 😅. I’m social, disciplined, comfortable with disagreement, hard to rattle
  • My strengths and blind spots are the same traits at different intensities. Systems thinking can become rigidity; high standards can make me intimidating
  • I wake up at 3:45am and work weird hours. You absolutely don’t need to
  • I trust people who act with agency, own their results + tell me the truth. I owe you the autonomy to do that
  • I’m async-first. Write first; meet for debate, ambiguity, or something personal
  • Want a fast response? Lead with your rec + the context I need + a deadline
  • I lose messages in a 100+ convo queue. Please nudge me if I’m blocking you!
  • Please disagree with me! Direct feedback makes both me + the work better
  • I take my hobbies way too seriously: natural bodybuilding + reading

My 30-Second Self-Intro

I taught myself to code at 12, built the world's #1 homework planner, then worked on the Apple Vision Pro and early Apple Intelligence prototypes. My senior thesis on the technological singularity convinced me to dedicate my career to helping society adapt to AGI. When ChatGPT launched, a weekly gathering in my living room became The AI Collective, a global nonprofit with over a quarter-million members and hundreds of chapters. I serve as chairman and am returning to what energizes me most: building from zero with exceptional people. Outside work, I'm a bookworm, natural bodybuilder, personal-systems nerd, and occasionally write and speak.

My Personal Mission Statement

To be a loving, inspiring leader who helps others self-actualize by creating environments of passion and purpose. To invest deeply in family, friendship, and enduring relationships. To think rationally and systemically, act with agency, and realize my potential through lifelong learning, broad exploration, deep mastery, and relentless ambition. To play the long game while still stopping to smell the roses. To value the experiential over the material and peak experiences over passive comfort. To live with strength, energy, and an appetite for challenge and adventure, sustained by exceptional physical, mental, and social health. To build the tools and institutions that turn AGI into broadly shared human flourishing. To make a dent in the universe.

Personality & Strengths

My Personality Profile

  • Myers-Briggs: ENTJ-A ("The Commander")
  • Big Five / OCEAN: Very high Conscientiousness (108) & Extraversion (106); very low Agreeableness (61) & Neuroticism (38). As in, top 1-5% most extreme for all four 😅
  • BIS-11: Very low impulsiveness (41).
  • In practice, this means:
    • I am a mission-oriented systems-builder energized by ambitious goals and rational debate. I thrive on turning chaos into order and driving a team toward a clear, world-changing objective.
    • I view my (very) high disagreeableness as a feature of my commitment to my mission. I believe that intellectual honesty and rigorous debate are the fastest path to the best ideas.

My Strengths

My Gallup profile concentrates in Influencing and Executing – but my impact comes from how these combine with my drive for Significance. You should leverage me accordingly.

My Blind Spots (Where I Need Your Help)

I'm working to notice and correct these before they affect others. You are always invited (but never responsible) to flag them! If you name it, I will do my best to pause, understand the impact, and repair rather than defend it.

How We Collaborate

My Time & Availability

  • Working hours: I am effectively always working (usually 80-100 h/w 😅), but my core, most responsive hours are 9am-7pm PT. You can expect me to be highly engaged during this window. (Curious? Check out Chappy’s Core Daily Routine)
  • Weekends: My mornings before 9am, as well as Tuesday and Thursday afternoons, are my protected deep work blocks (eg. coding, writing, researching, strategy). I will be slow to respond during these blocks. I work intensely on weekends, but I cherish this time for uninterrupted, creative deep work. Please respect this by avoiding non-urgent requests.

Meetings

  • Philosophy: I believe meetings are for two things: 1) high-bandwidth debate to solve a hard problem, and 2) efficient, team-wide status updates and alignment.
  • Expectations:
    • Come on time & prepared: I expect the meeting leader to arrive on time and with a clear (and ideally written) agenda.
    • Active participation: I expect everyone on the call to be engaged and to contribute. The meeting leader is responsible for creating and facilitating these conditions.
    • Pre-reads: A pre-read in advance before is a gift to everyone in the meeting – especially if it’s more of a homework assignment rather than passive read! It's by no means required, but it is always appreciated and allows us to use our synchronous time for the highest-value and most informed discussions.

Communication

Note on my response time: I am often juggling a very high volume (100+ of open lines. While I will see your message, it may occasionally take me 5-8 days to respond to non-urgent pings. Please do not take this personally; it is a function of my batching system for managing focus. If you need a faster response, read on!

My Communication Principles

  • Async-first: I believe the best work happens in long, uninterrupted blocks of focus. For any complex topic, my strong preference is to start with a written, well-structured document (like a Notion or Google Doc). This allows me to engage with your ideas deeply on my own schedule and it forces clarity of thought for everyone involved.
  • High signal-to-noise ratio: Be concise. Use bullet points. Get to the point quickly and put your rec or key question at the top. I trust you've done the deep thinking; you don't need to show all your work in the initial message. Minimal ChatGPT fluff please!
  • Context is your responsibility: Please ask "does Chappy have all the context he needs to make an informed decision on this?" If no, provide the necessary background docs / links. Reducing friction is the fastest way to get a response!
  • Default to transparency: Whenever possible, our communications should happen in shared, public channels within the team. This reduces redundant conversations, creates a shared context, and allows others to learn and contribute.

The Right Channel for the Job

  • For non-urgent, day-to-day comms & FYIs: Use the appropriate public Slack channel. If you need my specific input, you must @ me or I will likely miss it. I am in over 100 channels (in AIC) and rely on mentions to filter what's important.
  • To get my input on a document: Share a Notion or Google Doc with me and @ me in a specific channel with a clear question and your recommendation. This ensures it hits my radar.
  • To pitch me a new, big idea: Write a concise, one-page document outlining: 1) the problem, 2) the proposed solution, and 3) a concrete first step. Share this with me via Slack.
  • For an urgent, time-sensitive issue (≤ 3 hours): Send me a text message prefixed with "URGENT:". This will get my immediate attention. My phone # is included in my email signature and on my Slack profile.

Feedback

How to Give Me Feedback

  • I am running a thousand miles an hour and am full of blind spots. Please help me see them! Your honest perspective is a gift that helps me and our shared mission get better.
  • The method: (a Crucial Conversations framework)
    • Ask for permission: Because I am constantly context-switching, the most effective way to give me feedback is to first get my attention. A simple Slack message like, "Hey Chappy, do you have 10 minutes for some feedback on X later today?" is the perfect way to start. This allows me to switch into the right mental frame to actually hear you.
    • Lead with the facts: Start with a neutral, specific observation. (eg. "In the leadership sync yesterday, when we discussed the budget, I noticed we moved to a decision without hearing from the broader team.")
    • Share Your story: Explain the impact this had on you or the project. (eg. "The story I told myself was that we are prioritizing speed over rigor in our financial planning, which makes me concerned about future risks.")
    • End with a question: Open the door for a real conversation. (eg. "I was hoping you could help me understand your thinking there?")

How I Give Feedback

  • My philosophy: (from Radical Candor)
    • I aim to care personally while challenging directly. I intend to address the work or behavior rather than the person, but intent doesn't determine impact. If I land badly or make an unfair inference, tell me!
  • How I recognize great work
    • I believe that recognition is a critical part of a high-performance culture. My goal is to ensure you feel seen and valued for your contributions.
    • How I show it:
      • Succinct public praise: I frequently give public praise for specific, excellent work, especially in our Slack channels or team meetings. My style is often succinct and direct, but it is a sincere acknowledgment of a job well done.
      • Trust and autonomy: The single greatest way I show my respect for your work is by giving you more of it. When you consistently deliver with excellence, I will respond by giving you more ownership, more freedom, and bigger, more interesting problems to solve.
      • Advocacy: I will champion you and your work in the rooms you are not in. I will use my network and my platform to create opportunities for you and to ensure your contributions are recognized by the people who matter.

This is definitely a WIP and probably always will be! If we've worked closely together: What here matches your experience? What's missing or wrong? I care much more about making this true than making it flattering.

Hobbies

I have two hobbies and I take both of them very seriously!

Bodybuilding (Natural)

Outside of tech, I live a second life as a natural bodybuilder! I’ve trained with intent and intensity for 8+ years and occasionally compete in the INBF/WNBF natural federations. I track every set, iterate my programming, and measure what matters – I even built my own app to systematize progress! One reason I love lifting is the objective daily affirmation: I walk in, hit a PR, and know definitely that I’m the best I’ve ever been!

Reading

I am a bibliomaniac. I read 50-100 books a year, and much of my personal and professional philosophy is a synthesis of frameworks from thinkers I deeply respect. If you want to understand the "why" behind how I operate, these books are the source material!

Read my full compendium of book notes here: Book Notes