cold emails to hot people

In 2005 I've started my first entrepreneurial quest. The idea was to build a bracelet with LEDs for sports fans, these bracelets will all be switched on and off through a central wireless system, making each one of them a pixel in a giant "human screen".
I called it Masstie.

It was about 8 months before the 2006 Football (Soccer) World Cup in Germany. Deutsche Telekom was the main sponsor of the event so I've decided to email them and ask if they'd like to sponsor Masstie.
I looked at their website, found the relevant email address and sent a short email, describing my idea.
A day went by and they answered! they wanted to have a call with me. We talked over the phone and I explained my concept. Unfortunately that's all I really had back then - a concept in my mind, nothing else - no marketing material, no videos and no product. The fact that they answered my email, took me seriously and were really into my concept was very encouraging.

I've started my first ever fund raising roadshow. Back then I liked to read [Guy Kawasaki's] (https://twitter.com/GuyKawasaki) blog, so what did I do? sent an email, asking him to invest.
People like Guy Kawasaki don't usually publish their private email address, they have a public one and their assistants screen these emails for them. The particular assistant that got my email was probably not the sharpest tool in the shed, as he somehow managed to do "reply all" to my message, adding Guy's private email and saying something along the lines of "Hey Guy, what do you think about this Goofy idea?".
Now I had Guy's direct email address and he owed me an apology for his assistant's insult. I've emailed him directly and we had a few email exchanges about Masstie. I was not able to convince him to invest but, Hey, Guy Kawasaki was answering my emails!

Later on I was working on a new concept, Stadeom, a website where sports fans can interact with each other while watching a live game.
I loved reading Fred Wilson's blog. He invested in Twitter, he showed interest in sports and I thought he might get Stadeom. I wrote a short email "As an avid reader of your blog I came to the understanding that you like sports & digital-social-communication...". Fred answered and we started exchanging emails about my idea. He thought Twitter is a good answer to what I was trying to build. From the way Twitter is used today some people may think that he was right but I still think Twitter is not the best tool for two way live interaction, maybe one day I'll write my thoughts about that.
I kept emailing him from time to time about different issues and usually got an answer (albeit short), and this is someone who writes regularly about the huge amount of emails he's getting and the difficulties he has managing all of them.

2007 was the "year of the widgets", me and my friend built a really cool one. We called it LinkedInAbox and it was a little widget that could be embedded on any blog to expose the blogger's LinkedIn data through a minimalistic UI. When I was done with coding and the product was ready we sat down and wrote an email to editor@techcrunch.com who back then was Michael Arrington.
Later that evening we went out to a party, convinced that no one would read our email. On our way back home I've checked my emails and there it was! Michael Arrington wanted to confirm a few details and soon after our reply he [posted about it] (http://techcrunch.com/2007/02/21/passionate-users-jumpstart-creativity/) and this post not only sparked more articles about LinkedInAbox but also made the people at LinkedIn notice us. They contacted us. We wanted them to buy LinkedInAbox but it was the wrong timing for them since they've just started to build their API and thought that buying us would send the wrong signal to other potential developers.

The next year I've built another widget, this time I called it MyBefia.
MyBefia was like Alexa or Comscore but for iPhone apps.
It was, once again, an embeddable widget where the publisher could set up to 3 different iPhone apps and it would display a graph showing their App Store ranks over time.
I emailed Michael Arrington again. This time I've added a little strategic move - I knew Michael had a sweet spot for Loopt - so in the example I've sent him I had Loopt and its competitors and the graph was showing that Loopt is getting more traction while its competitors are loosing some.
So, then again, Michael posted about my widget, and traffic soared.

When I was running BeeTV I've sent a few emails to Steve Jobs, trying to convince him that my company is the future of Apple's TV strategy.
Sadly he never answered me...

There are many great articles about how to write a good cold email (like this one).
Many of the cold emails I've sent were not masterpieces and still were able to help me move forward.
So my advice is - just try! send your cold emails, there's nothing to lose right? and sometimes, you'll get big wins.