On Reaching Inaccessible People
Surprisingly, my answer isn't all that different from "Strategies for dealing with ADD" and they're not different from "How to prototype effectively".
It all boils down to protocols, practice, focus, and subject matter.
First, for my own personal development, since 2012 I've been making it a practice to meet with someone "inaccessible" at least once a month. I find someone who I don't have any business speaking with but (and this part is important) who I genuinely needed advice from. I don't just reach out to people because I want to say "I reached out to so and so". The point was, at a frequency of once a month, I am guaranteed to have a problem I need help solving. And if I am going to get advice, I should try to get it from the best. And then prove to them I was worthy of their advice so I can honor the time they invested in me.
Also, inaccessible doesn't always mean famous (often just famous to me). I remember randomly reaching out to Jan Paul Posma, for instance, because my life goal is to (in may respects) become more like him. He's worked with wikimedia, is a fantastic visualization designer, is extremely knowledgeable about web annotations, and is all around just a philanthropic person more people should try to emulate. Why not me? Why not ask if I can treat him for coffee and learn how and by what circumstances he got to where he is. I've similarly reached out to the head of Chicago University's institute of knowledge, and several data mining, AI, and NLP experts from whom I wanted to learn about their research.
Do your research. Sorry for my language, but one thing I learned from Oliver Yeh is: Do Your Damn Research. I think Oliver and I are both playfully competitive with each other re: rock climbing, so I can't admit it to his face, but Oliver is a great guy, a heck of a businessman, and he gave me some of the most sobering and best feedback I've ever heard. Real radical candor worth paying for.
I was sitting with him at his SensorTower office a few years back (he was nice enough to meet with me to offer advice) and I asked him if he knew any investors who I should be speaking with. In more or less words, he basically said, "Come on, you need to do your research. There's no reason why you can't go through my linked in and see for yourself who's a good fit. Why should I have to do this work". And I couldn't help but think. Frick. He's completely right, this mistake should never happen again. He was nice about it, but his radical candor was something that was a critical development for me and for which I am very grateful.
Since then, and also because of feedback and an amazing precedent from Joe Polastre, I've been keeping a list of people I need to speak with, as well as a list of the people who are connected to these people. I do research both before meetings, and before asking for introductions to make its clear why the introduction is necessary and why it needs to be the intro'er.
Apart of the research process is seeing how they write (if you've conversed with them before or read their essays) and trying to value their time. Demonstrate what about their work convinced you that your question must be answered by them. Show them what the products of your work will be once you have an answer.
Return the favor. I work really hard to connect my friends to people in my network. Because of Oliver's feedback, and to hopefully help others avoid similar embarrassment down the road, at the end of my meetings I offer people the chance to look through my linkedin and offer to connect them to people if (a) I know the recipient well enough to respect their privacy and time and (b) because there's a necessary reason.
Having genuine intentions. I think one of the biggest reasons people respond to me is because many of the projects I work on are philanthropic. I work on mostly open source projects, in a selfless capacity (often trying to protect people's freedoms), I work at a non profit, and I try not to capitalize on other people. Perhaps it's Machiavellian, or maybe it's just a positive externality; it's simply a fact that having philanthropic threads in your life can make it easier to establish foundations for strong relationships and can empower you to explore followup opportunities in the future.
Another policy which is important to me is, "anyone who is worth meeting, is worth treating". Being a generous person and earning this reputation only makes it easier to meet with others in the future. The more meetings you setup, the more you feel in your own skin when you reach out to people, and the more natural the exchange is. Also, don't be afraid to be persistent.
Be in the right communities and networks. Your job and affiliations partially determine who you have access to. If you are at an early stage startup, be aggressive and ask to be included in advisor meetings. This led to me meeting all sorts of interesting people like the former CEO of CNN, an early VPE for Facebook, strange serendipitous conversations with Ashton Kutcher and MC Hammer.
Ask questions which are extremely easy for the person you're reaching out to, to answer. In addition to "do your research". Also, "do work upfront". Figure out where peoples' offices are. Suggest locations to meet around them. Offer times they can pick. Let them answer with yes.Peer review. Ask your friends if you can read some of their emails which worked well for them. Have them read over your drafts. Try the same email you're planning to send, but to someone else representative of the person you're actually trying to reach (see how it performs).
Become exposed to that which you don't know. Look, sometimes this stuff is really obvious but unintuitive, like we just don't think about it. I remember when I was working at Hyperink (we had a perk of Friday reading time), I picked up this weird book How to Win Friends and Influence People which I could not believe existed. I was almost offended that it was on our bookshelf. And well, actually it was pretty incredible. It offered stories rather than a template and allowed me to come to my own conclusion. More than anything, it gave me a window into how people might think, beyond their actions. Understanding people and listening to people is critical to this whole formula.
In short, do your homework, have a darn good reason, become the person that is worthy of a response, prepare the field for victory (in the Sun Tzu sense), be a genuine person, and leverage the resources in your network to increase your chances. And when when there's no response, don't give up. Meet those who work for the person and ask them for an introduction. Find out who this person works *for*. Reach out to them. Figure out who the person's friends are. Get in touch with them. And if you get a no, understand why, improve yourself or your cause, and then if it's really necessary, reach back later with your updates.
If I hadn't done this, I would have never flown to San Francisco with [[Stephen Balaban]] after being rejected the first time around by YCombinator and then (nearly) demanding (after 3 additional emails) that we deserved another shot. After our talk w/ PG (rejected again and accused of saying "innovative" a lot), I wouldn't have had the idea or the confidence to reach our to Kevin Gao and Matt Lee to discuss collaboration. I would have never connected with such amazing advisors and mentors. I wouldn't have had a chance to learn from Oliver. I wouldn't have been able to reach out to open access institutions and grow Open Journal Foundation to over 20 organizations. Or had the audacity to believe I could also rally troups to protect net neutrality. I wouldn't have met Jan Paul Posma. I wouldn't have had the guts to reach out to Entelo and become one of their early tech advisors. I would have never gotten VC meetings with the likes of David Hornik, Michael Neril, and Simon Rothman. I wouldn't have connected with over 250 artificial intelligence phds who became the @Hackerlist, Inc network. In short, I wouldn't be who I am today if it wasn't for the support of a lot of people who were willing to click reply and invest a little bit of faith in me.
In the words of the late great Randy Pausch, "Brick walls are there to give us a chance to show badly we want something"
On Reaching Even More Inaccessible People
From https://www.facebook.com/michael.karpeles/posts/10103670889584710 on February 27, 2019
At some point, a person may become so busy or in-demand, "reaching" their sensibilities through the art of messaging is insufficient -- one must delve into the art of physically acquiring their time and attention.
Persistence & Escalation. A common approach for contacting a busy person is to try respectfully messaging them via multiple mediums. As it pertains to respect, it's valuable to have a sense of what "escalation" means for a recipient. If your message is not necessarily time sensitive (first off, you should consider choosing your timing well to maximize the chance of your recipient seeing it -- e.g. likely not sending a message at 4am when it is likely to be superseded below anything which arrives at 7am, as the recipient may be waking up), don't blast recipients all at once with a message to all their emails, twitter, facebook, etc. Give them some time; consider sending followups, each time escalating onto a channel which may feel a little less appropriate / too personal for the context of the message, but not unjustified by the importance of the message (where importance in many ways 𝒊𝒔 influenced by an art of messaging). I often send an email (especially if I don't know the person well) and then tag on facebook or twitter alerting them of the email and a few works of context, e.g.: "Hey Annie, just sent you an email, heard there's a criminal in your area -- checking that you're ok. Are you ok Annie?". It's possible your message + ask get watered down as you escalate, i.e. compromising as you re-align based on how much availability you perceive them to have (something is better than nothing).
Don't make me think. When you do send a message, less is often more, try not to ask multiple things (decision making is a scarce resource -- Brad Rubenstein, author of "Risk Up Front" and one of my Open Library mentors). Less can be more -- why give people concerns they don't have (great advice from David Hornik, when I was talking to him about Hackerlist in 2014). Try to do work for people to reduce the effort to decide + respond (e.g. "do you want to meet at (a) stanza [link to map] or (b) atlas [link to map]?"). These points, though, all assume (or optimize for after) one has acquired someone's attention (which was the focus and assumption of the original essay).
Interrupts. One of the most effective and disruptive (by definition) ways to reach someone is unfortunately via an "interrupt". For many people, this is a phone call. Some people don't respond to calls. For others, this is asking a friend to deliver the message in person. Or, to deliver the message yourself in person. This does raise an important question: Is what you have to say worth an interruption (from the recipient's perspective)? Many people become desensitized to interrupts and create obscure protocols for allowing them to be interrupted (which they share with people in their inner circles). e.g. Maybe you've had a professor (notorious for receiving lots of mail) ask you to put "IMPORTANT:" in the subject/title. A grey-hat approach may be to compile a list of these common approaches (calling from a # which uses their same area-code, adding IMPORTANT to email subjects) and A/B test them to create your own "rainbow table" or library of interrupts. Which is (often in a less rigorous and uninformed way) what spammers and phishers often do. And this probably isn't how you want people you respect to perceive you, so use with discretion (and have genuine good intentions). Many people only answer phone calls from known numbers. So, getting to know people well enough that they have your number (for other reasons) is [unfortunately] a great Machiavellian approach to preparing for a future ask and is the essence of "being connected" (sorry, I know this is common sense stuff, these are notes to self).
If one's interrupt doesn't meet another's bar, one risks damaging the relationship (or more specifically, losing one's trust that their interrupting messages should be considered). You may think about it as "the boy who cried wolf". This quality of people trusting your interrupts can be influenced though. For instance, your close friend who you've known since childhood is likely more willing to answer your phone call (even if they are Bill Gates) because friendship is one such force which behaves as a weight which can serve to prioritize your interrupts. This is one reason also why being intro'd via 2nd connections is such an effective mechanism.
Be creative. People will often be less pissed off and inconvenienced with your ask if you put time and creativity into it (as an expression of appreciation/gratitude and apology). Send 200 roses to their workplace and say, "search your inbox for: I MISS YOU LETS DO LUNCH FRIDAY -- your secret admirer mek".
Making interrupts ok. Interrupts tend to be appropriate when there's something time sensitive -- e.g. "I'm at your place, are you home?!" or "I got hit by an enormous avocado and need help now". You can make anything time sensitive or employ all sorts of practices from e.g. Robert Cialdini's book Influence (or others like it). But a la Aristotle's Rhetoric, it's pretty easy to tell when someone is employing such a tactic against you. It feels bad and you should use your discretion and moderation. These tactics are also weights and can be effective, so long as they are employed with some level of tact and don't treat the recipient as if they are an idiot. Which brings me to don't:
Don't. Don't stalk people, don't spam people, don't make people uncomfortable, don't treat people like they're dumb. Don't treat people like tools. Be good and do good. And everything will be fine.
-  https://openlibrary.org/books/OL8157377M/Don't_Make_Me_Think
-  For most people, this should all be intuitive, trivial, and is the topic of any and every "I don't have any specific qualifications, but look at this book I wrote a book about networking" book. But, it's amazing how often I forget (and find it useful looking at my notes), and unfortunately for you, these essays are actually written for me (so I can work through and organize my thoughts, even if the majority of these thoughts end up not being useful or eye-opening).