About 5 years ago, a popular online entrepreneur and I had dinner. His name is Tim Ferriss.

I had a good idea who Tim was at the time, but I really wasn't aware of what an insanely popular figure he was in the world of personal development and lifestyle design. 

I was living in San Francisco when Tim first came onto my radar.  A coworker of mine mentioned him offhand, referencing a book he had recently written on health and wellness......something about losing weight by immersing yourself in an ice bath. "Umm, come again??"

Curious to learn more, I checked him out online and saw that he wrote a previous book called The Four Hour Workweek; based on the reviews, I bought it a week later on Amazon. I enjoyed the read, and I got a lot of great ideas and inspiration from it. A week after that, I found Tim's website - again, I liked his his content and he seemed like someone I'd enjoy meeting.

So I sent him a carefully crafted cold email. A few days later, I heard back from his assistant. A few days after that, Tim and I traded some text messages and we eventually met up near Hayes Valley in San Francisco. We ate at a Thai restaurant and had a great conversation that lasted upwards of two hours.

My point with this post isn't to show you how cool I am for having secured a meeting with Tim. And it isn't about what we discussed. It's to drive home the point that most of us have the ability to connect with people who are seemingly out of reach. This is especially true now more than it has ever been. We are living in an age where accessibility has never been greater. And there is a spirit of generosity among the "New Rich," as Tim refers to them.

So here are a few tips on how to do it:

1.    You have to be excellent. Sorry, but there’s no way getting around this one. And I know what you are probably thinking: “But, Jon, I’m not a former FBI Counterterrorism Agent - you can throw that around and people are going to naturally be interested in you.” Well, yes and no.  You’d be surprised how many times I’ve cold-emailed people and gotten crickets.  Folks are busy.  They have their own stuff going on.  Plus, here’s a shocker, it’s likely that I may not be as cool as I think I am.  To be sure, it’s good to have an interesting professional background, but lucky for you, even if you don’t have a job history that sets you apart from the masses, you still have a shot at breaking through. See, I think many people don’t give themselves enough credit for the cool things that they’ve done in life.  In your heart of hearts, you know that there is something that makes you awesome. Me?  I hiked to the top of Mt. Whitney a few years ago and before that I ran a marathon in San Francisco.  I realize that Mt. Whitney is dwarfed by the likes of Denali, Kilimanjaro, and Everest, but I’m proud of this feat nonetheless.  I know that many people have completed marathons and that 26.2 miles is nowhere near as hard as an ultra marathon.  Someone out there is always going to be a little bit better and cooler than me. And I'm ok with that - constantly playing the comparison game is futile.

But here’s the thing - maybe you know a little bit about the person you are reaching out to (because you’ve done your homework) and you can share a similar accomplishment or experience or something interesting about yourself, all in an attempt to pique their interest. You have to be creative and ask yourself, “If I were a high-level person, what would compel me to reply to someone?

2.    List your greatness.  This goes along with number one, but you’d be surprised how many people don’t do this.  You have to let them know that you are the kind of person worth responding to, and you can only do that by gently highlighting your worthiness. There is a fine line between doing this and coming across as a braggart. Let your intuition be your guide.

3.   The power of name-dropping.  If you have a connection, mutual friend, distant relative, or anyone at all who is more connected to this person than you are, then be sure to work this in early within your email. This is very important.  I don’t care if someone recently became one of your Twitter followers, you can use this as a connection.  Having a connection instantly qualifies you because the person you reference establishes your credibility. Be creative and "think outside the box" (even though using that hackneyed cliché makes me cringe).

4.   Flatter them.  No one ever gets tired of hearing about how great they are.  Please make sure it’s a genuine sentiment and it comes from the right place.  

Advanced ninja trick:  If you have a blog, write a post and link to their website or Amazon page where they are selling their book; then, when you email them, you have license to mention that you recently linked to their site in one of your recent blog posts.  Again, if you do this, please make sure that you are coming from a genuine place.  Are we noticing a theme here? Your blog post/mention/etc. must be grounded in a sincere interest in giving the person credit for their awesomeness (see if you can find my example about how to do this further down).

5.   Cut to the chase.  Ask the person what you want, and keep your email short.  If you are contacting a high-level individual and you’ve managed to get them to open your email, you’ll need to keep it brief.  The goal is to get them to read the entire message instead of giving up halfway through. Keep it pithy. Maybe you ask them to answer a very short question to start a dialogue, as Tim suggested in The Four Hour Workweek. (I didn't do this with Tim, by the way.)

6.   Add value.  High-level people will always ask themselves, what’s in it for me? Whatever it is that you think will benefit the other person, be sure to say why.  Do not assume that the other person will be able to read between the lines.

7.   How to locate email addresses.  "But Jon, I don’t have their email address.  How do I even write them in the first place?" This one is easier than you think.  If you are targeting someone who works within a company or organization, it is likely that they won't have their email listed anywhere on the website (That is to say, anywhere that is visible on their public pages. More on this in a bit). Making their address public would assuredly bombard them and likely overwhelm their inbox. Interestingly, I have found that you can search the organization's website with the embedded search tool and often times you’ll get an email address rather quickly. The search formula looks like this: ["Jack Welch email"].  Done.

If the person is not affiliated with a company or organization, the first person to read your email will likely be a gatekeeper....

8.   Gatekeepers.  If someone is ultra high level, they'll likely have a secretary or assistant screen their emails.  This will be apparent if they list their email address as being something like MaryBeth@TigerWoods.com. Similarly, something more subtle to be aware of is something like info@PeytonManning.com, or there may just be a "contact us-style" submission form on their site.  I have found that prefacing the email/message with something like, “This message is intended for Mark Cuban” or “Please pass this business proposal to Mark Cuban” can be effective. Your goal is to get the gatekeeper to forward the message to the high-level person you are targeting.  It is likely that the gatekeeper has been instructed to forward all interesting proposals or inquiries, so they will not want to let anything slip through the cracks.  So what gets passed along?  Anything that adds value.  Anything that is out of the ordinary. You have to stand out.

9.   Subject lines.  These are huge.  I can’t say much here that hasn’t already been said.  Jocelyn Glei, writer and founding editor at 99u, suggests something along the lines of this formula:  [Organization/Person you are targeting] + [Your name], followed by a question mark.  Example: Jon Tasch + Burning Man?

I wish I could come up with something more effective than this.  But really I can’t, so there’s no use in reinventing the wheel.  All credit to Jocelyn for this very effective idea. I've used this a lot and it seems to work.

10.  Cast a wide net.  Remember, this is a numbers game. On numerous occasions, I have sent cold emails to people and gotten crickets.  Sometimes, though, I hear back from them and we secure a meeting.  I don't get down on myself if I don't get a response.  I just use it as a way to get better and move forward.  Cast a wide net and see what you get back.  

Who are three people with whom you'd like to start a dialogue, who are seemingly out of reach?