The Apprentice Thread

A while back, LessWrong poster Aysajan put up a post asking to be someone’s apprentice. He talked about it with johnswentworth, who I recently confirmed via meeting him in person is awesome and does reliably interesting work, and an apprentice experiment was born

As John says, you gotta admire the chutzpah. Asking for what one wants is a known to be successful but highly underused strategy, I presume mostly because of the permanent global chutzpah shortage and the associated danger that it might result in mild social awkwardness. 

In addition to the highly successful use of chutzpah, this also points out that apprenticeships are also a known to be successful but highly underused strategy. My feelings about so-called ‘schools’ are well known, but education is great, and apprenticeship is one of the best ways to get an actually excellent and useful education. 

I’ve been an apprentice, regardless of whether it was called that, and it was awesome. At Jane Street they have a formal education process, but the core of how you get good is an apprenticeship. You learn from the best, by working with the best and asking them questions. I believe I am a natural trader, but I am good largely because I learned from working directly with three of the best in succession at three different jobs. I know Magic and game design by spending tons of time talking and working with top Magic players and game designers. 

I’ve been a mentor of sorts a few times. That’s mostly been great too, and I’m plausibly taking on another one now, although I’m cheating because he is already exceptional and largely does not need the help. 

Thus, we have two overpowered strategies here that the world needs more of: Apprenticeship and Chutzpah. Lowering the activation energy required for either or both of them seems great, as does providing encouragement.

Both can of course be overused and abused. Too much of the wrong kind of chutzpah is no good for anyone, and apprenticeship can turn into a bunch of not very useful unpaid work, or end up holding people back. In the context of posts like this, I am not much worried about either of these failure modes. 

For this post/thread I will focus on apprenticeship. In particular, I want to see if I can give social permission and a coordination mechanism that can perhaps take place in the comments (reminder that my posts have two comments sections, the primary one at DWATV and a secondary one at LessWrong). 

Replies to this post should take the form of any of the following:

  1. [MENTOR]: A non-binding indication of potential interest in mentorship. Mention that you might, at some point, be interested in taking on an apprentice. This commits you to nothing. Make sure to indicate what you’d be teaching them and what project would likely be involved, and open with [MENTOR]. You are free to include contact info, or not include it and monitor replies.
    1. Replies to this comment to indicate potential interest in being the apprentice, marked [APPRENTICE], which should include a method of further contact.
  2. [APPRENTICE]: A non-binding indication of potential interest in being an apprentice. Mention that you might, at some point, be interested in being an apprentice. This commits you to nothing. Make sure to indicate what you’re interested in being an apprentice in and learning, and an indication of what’s motivating you.
    1. Replies to this comment to indicate potential interest in being the mentor, marked with [MENTOR], which should include a method of further contact.
  3. [NORMAL] You’re free to comment as per normal, but start with [NORMAL] in the top-level for clarity.
  4. [NYCBUSINESS] if there’s some chance, depending on what it is, that you would want to do the thing I talk about below. 

Cost of speaking up is low, potential upside is high, and hopefully not too much chutzpah is now required. 

As for me: Right now, my main focus is on game design. We hired two new designers this week, both of whom I’m super excited to work with on Emergents, so for now my card is full. Depending on how much bandwidth I prove to have, I could consider mentoring someone at some point in either game design (on either Emergents or my other project), in trading (although I kind of already know who that would likely be if it happened), or someone I trusted sufficiently who wanted to work on Aikido. I might also want to be an apprentice at some point, likely in something AI-alignment related, but that would be a long way off.

I’ve also got another project potentially in the works that I’d love to work with someone on, which would involve someone taking on a likely-more-than-full-time job and a lot of responsibility, starting and running a business I want to exist. It would be hard work and require a self-starter, and all that, but won’t require you to do startup fundraising – it would be a real business, and would succeed or fail organically. It would be local to New York City. If you think you might be the person for the job, you can mention that with [NYCBUSINESS], tell me as much or as little as you’d like, and if/when I’m ready I will reach out. Again, this commits you to absolutely nothing.

This entry was posted in Uncategorized. Bookmark the permalink.

19 Responses to The Apprentice Thread

  1. Seth Green says:

    I like this idea a lot!

    [APPRENTICE] for learning how to build stuff, specifically wooden stuff. I am hiking the Appalachian Trail at the moment and I’ve benefited from lots of cool structures that people have built for hikers’ benefit, specifically shelters, privies, tenting platforms, and boardwalks. I have been reflecting on how I don’t know how to build any of that, and that even the simplest structures likely manifest accumulated knowledge that I don’t have. So when I’m done with the trail, I’d like to buy some land and turn it into a fun retreat. Would love a mentor in this!

    Planting crops is also of interest.

  2. Zahmahkibo says:

    [APPRENTICE] in game design and development, digital or physical. Motivated by… a lifelong love of the study of play, I guess, and the belief that I’d be more happy and fulfilled working in game design than in any other career. From a couple years of self-directed learning I have produced: some impressive Unity tooling, stacks of notebooks, heaps of half-baked prototypes, zero actual published games, and the inescapable realization that I’ll probably never work as well in a solitary environment as I do in a collaborative one. Career to this point includes several years’ experience as a programmer in mature start-ups, mostly doing backend for bookkeeping and other finance-adjacent systems.

  3. TB says:

    [NYC Business] [Apprentice]

    Am interested in learning more. Have an M.D., but unlike most physicians have a) pretty broad set of skills including some basic finance, Python, SQL, etc. and b) product-focused entrepreneurial experience (specifically, not just starting a practice or something clinical; and as external proof, have product-role offers at tech startups and not just “CMO” offers). Can support myself working a clinical weekend here and there, so taking equity rather than salary for a period of time is not an issue.

    In terms of value set, I think building things is super interesting and motivating. It has lower expected value than going into some subspecialist private practice and I am ok with that. However not making money is pretty lethal for businesses in the long term, so will be interested in the business case as well. Whether it’s a V.C. capitalize-and-grow-at-all-cost model or a small-business model is irrelevant to me, but I may have opinions on what is best for the business once I learn about it.

    Less interested in businesses where the competitive field is super wide, e.g. let’s build consumer app X, or open restaurant Y. More interested in unexplored niches or markets that require deeper knowledge / expertise. You can reach me at para dokein (at) gmail — this is my spam email so please excuse any slower replies.

    • SamChevre says:

      Are you at all interested in insurance? I could not serve as a mentor, but you’re describing something very close to the ideal skillset for someone working on underwriting design, and I have decent contacts in that field.

      • TB says:

        I’m interested in pricing risk and (in some fields like health or auto insurance) modifying behaviors to change risk. Most insurers are large companies due to capital requirements, and if I’m to work as e.g. clinical data analyst in room B-302 at a faceless insurance company X, my salary would probably have to be fairly high (as that’s not particularly more exciting or career-progress-y than my current work). But am open to hearing about anything.

  4. Steven Lee says:

    In the name of Chutzpah…
    [APPRENTICE] I want to get better at data engineering, specifically spark in either Scala or Python. I’ve done a few basic projects and they worked, but were not very good compared to what’s possible. Also, I want to satisfy my curiosity on how good I can get at data engineering. It eventually becomes extremely complex, and I’m sure I’ll find something that is beyond me. I’m also pretty sure I’m not there yet, so improvement is possible!

  5. A person who doesn't put his name online says:

    [MENTOR] This might be a little different, but I’d like to offer to mentor anyone without the cultural education to fit in as a knowledge worker. I grew up in a very dysfunctional Appalachian environment with no role models or prep for the academic and professional world. I didn’t know how to set a personal budget, talk respectfully with superiors, dress properly for informal situations, discuss finances, negotiate, etc. etc. etc.

    I failed to complete my graduate degree due to these deficiencies, but have since then had a successful professional career for about a decade and a half. So, I’m probably not a great mentor for someone who’s a first generation academic, but if you are a first generation knowledge worker, leave your contact info here. Leave a little bit about yourself and the industry you are in or will be going into.

    I would envision this mentoring process to probably take the form of weekly or by-weekly video calls, at least to start. I’ll probably recommend a small number of books for you to read for us to discuss. I promise they won’t be fascicle self-help or business books.

  6. ray says:

    [MENTOR] I will teach you software engineering, in the most literal sense. I do this professionally with some of my time, and it’s greatly appreciated by my students. What I teach will not help you get tech jobs or get promoted in your tech jobs; that’s a very different skillset which is mostly about cultural immersion in tech-job culture. What I teach *will* help you construct software in a careful and effective way; it’s best if you have some goal and you feel overwhelmed or decision-paralyzed about the path to reaching it.

    [NYCBUSINESS] I love New York. And business.

    • ray says:

      > What I teach will not help you get tech jobs or get promoted in your tech jobs; that’s a very different skillset which is mostly about cultural immersion in tech-job culture.

      (I think the commenter above me is offering this, if you want a job.)

  7. ogennadi says:

    [APPRENTICE] I’m up for it. My email is and I’m first-generation software consultant wanting to learn how to “adult” and how to play well with others at client sites. Please send me an email and I can give more details. Thanks.

  8. Jackson says:

    …in game design in particular (would love to help in any way with either of the referenced projects).

    I’ve felt some of my most intense emotions deep in a great game (in particular during the 13th hour of a diplomacy game back in college). I want learn to learn how to create beautiful systems that can inspire feelings like those. I’m working on this alone right now — roping family and friends into zoom playtests — but I want to pursue this with others, because I think that could help me move from interested and passionate to excellent.

    To quickly flesh out a bit of background, I currently work at a global macro hedge fund, my academic expertise is in game theory, poli sci and compsci, and my favorite games are Twilight Imperium, Avalon, and Diplomacy.

    email is!

    As an aside, though a mentor-mentee relationship is likely more effective, I’d also bet a cohort of “apprentices” sharing ideas and feedback would be more effective than us all hacking it alone. It looks like there are a handful more more folks in this thread in the NYC area who are interested in game design than there are potential mentors. Whether or not we can all find mentors, I’d love to talk and brainstorm with anyone working on games or interested in strategy more generally in a mentee-pool, so to speak. My personal projects currently include a couple political/voting games, one that is more traditionally structured, one that would serve as 24/7 roleplaying life “overlay” for a cohort of friends.

    • rossry says:


      Commenting to pin interest in a game-design-focused workshop/playtest group.

      I’m a quantitative trader and research economist based in Hong Kong, and I adore games that require rapid communication and thinking on your feet (bughouse, deck deckbuilders with “bullet” time controls, figgie and other trading games), as well as strategy games with puzzles to solve (Magic).


  9. Massimo says:

    [NORMAL] I’ve always been interested in all aspects of game development, with a focus on independent videogames, though I feel a little caught in the middle with regards to all this. My skills are at the point where I can barely work professionally and could probably help out someone with zero experience in stuff like games programming or game design, but I would probably still benefit a lot from working closely with someone who has 7+ years under their belt in either of those fields. If that sounds like you (someone interested in games programming with no experience or someone very experienced who would mentor me in game design or programming) do reach out, but there is one field I’m interested in where I definitely feel a mentor would go a long way:

    [APPRENTICE] Music Production, specifically I want to learn this so I can compose and arrange tracks for my own games. I don’t know any instruments but I do want to learn to play piano in service of this goal. I’ve experimented a tiny bit with this in the past but it always felt unintuitive and frustrating doing even the simplest stuff, and since it wasn’t a critical skill I never forced myself over that initial hump. I’m hoping a mentor can help the early learning experience go smoother and motivate me to practice.

    My contact info and portfolio can be found on my website

  10. DM says:

    [APPRENTICE] Looking for a mentor in data science. I’m currently leading a team of 10+ analysts and I feel like there is so much I don’t know. I’m good at general BI, requirements gathering, data manipulation, database design and passable at ML (just deployed a pytorch NN model). I know almost nothing about statistics, descriptive and predictive modelling. Generally I feel myself heading toward management without ever having built a solid technical base, which scares me.

    Contact info:

  11. scmccarthy says:

    [APPRENTICE] Looking for a mentor in machine learning. (To be clear though – I’m not a machine.)

    My background: I have a lot of software engineering experience, and some game design experience. I’m interested in doing things that give lots of value to people, so am currently employed in (non-game) software. This is also why I’m interested in ML/AI – it seems like the moral character of people and teams that build AI will impact the future, and being moral is something I think I’m good at.

    I realize there are resources available for learning about this, and I haven’t used them, so maybe my level of motivation for this is just too low right now? But I’m posting this, so it’s close, at least… In any case, you can let me know if you’re interested in talking further.

  12. Kenny says:

    [NYCBUSINESS] I’m curious!

  13. AT Natenshon says:

    A cool idea and very relevant to my type of work
    [MENTOR] For people interested in vaccine or drug development and curious about what kinds of skills are needed for overseeing a product through the development pathway, as well as the kinds of credentials that help put you in a place to get this kind of role.

    [APPRENTICE] I would be interested in learning more about trading, investing, and probabilistic games and decision making.

  14. CC says:

    [NYCBUSINESS] Would love to learn more about this

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s