How to DM your heroes when they follow you
1. specific proof-of-work: “I’ve been a fan of your work and writing since the livejournal days”
2. share something specific about yourself, their influence on you: “your work shaped the way I now do X”
3. ask easy-to-answer specific question. I would try to have a yes/no component, try to make it something more nuanced than what they’re used to answering all the time, something compelling and slightly personal but not too personal. really smart move is to ask about someone *they’re* a fan of.
In my experience, if you compress all of this into about 3 short lines, in a single DM, you basically make it irresistible for them to respond, and you’ll likely become friends. This is how I’m friends with some of my mutuals who used to seem like they’re way out of my league
underlying principles are:
– these people are busy, so keep your texts simple and short
– they’re used to dealing with people being starstruck, so give them the relief of not having to manage your emotions. No “I’m sure you get this all the time” or “you’re probably not gonna see this” typa nonsense. Edit that out. A perfect ask comes without strings, like an oasis in the desert. Talk like you’re casually confident (but not arrogant!! edit that out too) that you’re already peers
– they can’t trust you if they don’t know anything about you, so tell them a little about yourself. don’t go monologuing your life story (see principle 1), but rather, tell them a detail or two that their work impacted. Creators love to
when you have a chance for an audience with a king, don’t grovel at his feet for his approval. he gets that shit all the time, it’s exhausting. don’t snark and sneer at him, he gets that too. face him as an equal and give him a kingly gift that’s superior to everything else.
I have like a mental warehouse of such gifts prepared for the top 50-100 people I want to be friends with. If I bump into any of my heroes at a restaurant, I know exactly what I would say to them in 30 seconds
“I love your work” over “I love you omg” is like a secret password. but it’s not just the phrasing of course, a lot of it is about the vibe. you want them to feel “oh my god finally a person who gets me and gets it and they’re not a fanboy or hater, I don’t have to manage them, and they ask me interesting questions too!”
absolutely do not send them your soundcloud or youtube or novel draft in the first exchange. you should have it on hand of course (always be prepared), but your job is to be so interesting that they ask you for it.
if you present it to them without them asking, you’re likely going to relegate yourself to opportunist/wannabe in their eyes. not 100% necessarily, but this is a game of odds, and you wanna do things that improve your odds and not do things that worsen your odds.
Here’s one of my beliefs that I haven’t articulated clearly yet: I think the irresistability of a great ask is almost independent of the asker and the asked. a truly fantastic ask is something that the universe itself seems compelled to honor.
a fantastic ask is not the same as a dramatic gesture, which can be imposing. a dramatic gesture is like, sending them 10 pages of DMs. it’s intimidating, overwhelming, selfish, unfair. a fantastic ask is small but perfect, like a haiku you hear once and remember forever. (in this world / we walk on the roof of hell / gazing at flowers – Kobayashi Issa)
tbc
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found an old now-deleted tweet where someone said ~”you must get this all the time but will you give me an internship?”
It’s always interesting that people assume this about famous CEOs etc. A quick twitter search suggests that around 10 people have ever asked (on twitter). I would guess that less than 1,000 have asked in total, and that less that 50 have done their homework enough to say yes to
most people who ask are asking from a place of scarcity and wishful thinking. this pretty much guarantees a non-response because you’re giving them work to do. If you’re really serious about finding a way to work with someone you should figure out how to take work off their plate.
a good way to start approaching this project is to make a list of all of the people that Famous Busy Person interacts with, and impress them.
You can actually do this entirely on twitter if you’re patient and observant
But tbh it doesn’t even really make sense to try. sufficiently high status people have professional executive assistants with years of experience, so even asking at all marks you as “earnest but clueless and uninformed”. you’re better off working in an early-ish stage startup. (patio11’s reply)