As a person that many people want to get in front of, I can hereby certify that this fellow would have been blocked by a bayesian spam filter by email #2.
The trouble here is his attitude. It's all about demanding and demanding and demanding. Gimme. Gimme some time. Gimme some attention. Then gimme some mentoring, gimme some money, gimme an investment. You know what? Ef you.
The solution to landing meetings with anyone you want is fairly easy and has been understood since Dale Carnegie explained it (http://en.wikipedia.org/wiki/How_to_Win_Friends_and_Influenc...) in 1936.
You have to stop demanding things from people and start doing things for them.
Comment on their blog posts.
When you find out they have a new puppy, mail them some homemade puppy treats with a nice note.
When they ask a question on Twitter, move mountains to find an answer and send it to them.
Find out what charities they work for and make a donation. Or volunteer.
Write a blog. Give freely of your own knowledge. I did that and went from anonymous to internet-famous in 2 years. When I wanted to raise money, everyone knew who I was, and I got meetings with anyone I wanted with a one sentence email. Not because I was lucky and not because I was blessed and not because I was in the right club, but because I had been making a contribution for years before I started demanding things.
Either you're doing something I want to know about or you aren't. Don't give up after one try but don't bug the person constantly either. If they're not paying attention maybe you aren't interesting.
To follow up on some of your points: I don't know how easy it would be to get someone's mailing address--in my case, even getting their e-mail address correct was difficult. It's definitely possible to help them with something on Twitter or comment on their blogs, knowing that it takes a bit longer--and you have to wonder, at what point do you make the ask? You can compliment and help someone for a while, but at some point you have to ask them what you want to ask them. I'd be interested in hearing how you transition from being nice and giving to asking.
The problem with my own advice is that it's public in a large blog that is read by lots of people. This is exactly the same advice I'd give to any person who came and asked me "There's this investor, he's perfect for what I'm doing, but he isn't responding to my e-mails for the past 3 months." I could see people skipping that first part, which I would not do--you can't just start off by saying "Hey I'm going to e-mail you every day for the next 30 days." I sent nice, well-thought e-mails (VentureBeat edited out that part because the original post was too long) and got no response. Everyone who agreed to do the interview enjoyed it though. If I'm trying to get your attention, it's not like letting you invest in my company is only going to benefit me, remember I'm going to make you rich(er) some day! At least that's what I think, and that's what you're betting on when you invest.
I doubt I'll ever see a busy person support this advice openly. This is mostly targeted to the few people out there who are trying everything and it's not working. I'd use a combination of what you've suggested to build up some rapport, and eventually do what you could (using this tactic) until you're satisfied knowing you tried everything you possibly could before you quit and give up. I can't sleep at night knowing that I could have been just a little more persistent, but I gave up instead.
I have people doing what you suggest to my mobile phone. They call every day with a recorded message offering to solve my "money problems" and telling me that the only way to get them to stop calling is to give up and talk to them. If I could control the policies on my mobile phone the way I can on email, I'd send their calls straight to the trash without passing through me, as I do to anyone who attempts your suggested email spam strategy. I can't recall any case of someone successfully spamming me into submission.
Be absolutely sure that your e-mails have real content in them (i.e. this is progress we've made, we just closed X deal, etc.) that can be easily digested. The goal shouldn't be to make contact and then explain yourself. The goal is to generate interest, which will lead to the contact.
Also, if this technique catches on and hordes of desperate entrepreneurs everywhere start spamming every VC and investor they can find, it's all over. The HN crowd, of all people, should know just how easy it is to create a filter to immediately trash messages from a specific address. This is why it's important to have excellent content in your very first e-mail.
"And he asked a question. And I was like, I’m sorry did you say you were Tom Furness? And he said yes. I said, then I would love to answer your question, but first, will you have lunch with me tomorrow? And there’s a lot in that little moment. There’s a lot of humility, but also asking a person where he can’t possibly say no."
Although, admittedly, that's after you got them to say a few words to you and you're in front of a large group of people.
 http://www.youtube.com/watch?v=ji5_MqicxSo 19:40
For those who don't know, here's the setting of this talk:
This talk is one in a series given at CMU called the "Last Lecture" series with the hypothetical setting of 'what if you had one last talk to give?'. Randy Pausch, a professor at CMU, didn't have to pretend. He was diagnosed with pancreatic cancer, and in August of 2007 (when he gave the talk) was told he had three to six months left to live.
If you haven't seen it, watch the whole talk. It's really good.
I watched it all the way to the end without losing focus for a second. The head fake at the end really hit hard.
Awful advice. Not only does it not come across as humble, it comes across as cheap flattery and obnoxious insistence on something you don't deserve.
The initial moments after meeting someone are the moments when that person has the least interest in doing anything for you (next to the point before that, when you haven't met them at all). They lose almost nothing by making up some excuse not to do what you ask of them.
It's only after they've gotten to know you a bit, and after you've proven that you're interesting and valuable in some way, that they'll have a bit more incentive to do you a favor.
You need to know what YOU are bringing to the table and what THEY are bringing to the table. You need to have the full picture in your head. If you fully, passionately, believe that value will be created for both of you through a relationship ... all you have to do is convince the other person. If it's obvious for you, it'll be obvious for them too. They will, of course, meet with you.
On the other hand, if you're just bullshitting and you have nothing and you just desperately want to meet them because you're hoping that they will figure out how value will be created through a relationship ... well, they'll know what you are from the very first hello and you'll end up in the SPAM folder of their mind.
Its like running Harvard. Yes, under-qualified students will apply and try to get in, and so you'll have to spend time filtering them out. But if you have so much demand and more students have made themselves accessible, then on average, you will have a better selection of applicants to choose from. At least that's one way of seeing it.
Which reminds me - you can properly get almost anybody to respond to you if you send them a telegram, though you will have to find a company that still delivers them, since Western Union has stopped.
I think you cross that line right about when you decide it's a good idea to email someone every day to get their attention.
Is there more of an explanation on this somewhere? That seems incredibly far fetched to me.
There are plenty of startups who began with a meagre cash investment, but bucket loads of time and effort, that turned into multi-million dollar companies, in some cases without additional funding. So it's not as far fetched as it may seem in a one-liner that makes it sound like an overnight result.
This went on for almost a month before one of her friends finally convinced her to respond. We got married a year and a half later.
I guess women are just like other super important people: An early lack of response doesn't necessarily mean they're not interested; it just may take a while for them to detect the signal in the noise.
Since Andreessen Horowitz was part of their angel round, perhaps Marc Andreessen or Ben Horowitz were one of their initial targets.