How to Email Pornstars (Or Anyone)

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NOTE: This isn’t a guide to finding anyone’s email address. This assumes you already have it. For a good walkthrough on how to find anyone’s email, refer here, and here.

I just about shit my pants when I opened up my inbox and a rather prominent pornstar, writer and digital-piracy activist — in this case, Siri (link mostly SFW)— had responded to an email that I had sent her a few days earlier.

I wasn’t expecting a response — most of the cold emails I send out, I never expect a response, because I’m just a random nobody. I don’t even have a bed frame, true story.

A few weeks prior to that, my connections have included, but were not limited to: Brad Feld, a thought-leader in the tech/VC world and easily one of the brightest minds in the Denver tech community; James Altucher, one of my favorite writers and someone whose candor is absolutely one-of-a-kind; Ben Horowitz, co-founder of one of the most prolific VC firms in the world, Andreesen Horowitz, and writer of the book that I’m going to give everyone in my network a copy of, The Hard Thing About Hard Things.

(And you’ll see a pattern here: for my current projects, entrepreneurs and thought-leaders in the tech industry are typically the folks who I reach out to. I connect with women, too. Fret not. More on that in a bit.)

Was I grabbing lunch with any of them? Not yet, but it was a start. After all, these were individuals who regularly received upwards of 50-100+ inbound cold emails a day from random strangers, so the fact that I was even getting a response was quite the anomaly.

And whether you’re doing sales, building your network or simply seeking advice from an expert in a field you’d like to someday move into, email is easily one of the most efficient ways to connect with some of the smartest people in the world.

Here’s what I’ve done, the steps you’ll need to take and some templates/ideas that you can ultimately use to do the same.

Oh, and if you just want to skip to the emailing pornstars part, you can Click here to get instant access to the exact templates I use.

Step 1. Be a Fan of Their Work.

This is often where people get lazy, get stuck in the loop of paralysis by analysis and ultimately never go anywhere (or they’ll send out a terrible sales email that won’t get a response because who wants to respond to a fucking email that says HEY JUST CHECKING IN ON THAT THING THAT I TRIED TO SELL YOU LAST WEEK WANNA BUY WANNA BUY WANNA BUY!?).

The easiest way to almost always ensure a response from somebody is to become a fan of their work — chances are, the people you’ll be reaching out to have been interviewed, write a lot and are likely thought-leaders in their respective industries (and maybe they’ve written a book, too, so start there).

Read those things. Understand what makes them tick, what causes they’re passionate about and some of the things that they love talking about. Just 15-30 minutes of research will likely . For example, see the email I sent to Brad Feld regarding an article I’d written:

Screen Shot 2015-09-02 at 9.24.29 AM


First, you don’t have to be a prolific writer (like I’m not), a big deal, a thought-leader or anything else to get the attention of somebody who might be a few rungs above you in the world of business (although, to be honest, Brad Feld is a super accessible guy and a really cool dude). Why that email worked:

  • I wrote about a cause that was near-and-dear to Brad’s heart (and something I’ve written about a lot). I knew that because I’d read a lot of his work. In this case, depression and what causes people to commit suicide. Not for the faint of heart.
  • I indicated that I was a fan of his work, and mentioned how one specific post really resonated with me. (And it did. And I’ve written about that for other publications, here.)
  • Bad:  Didn’t have a clear ask. Still, if your cause/idea/writing is powerful enough, you’ll find that people will probably go out of their way to tell you (and share it). Sometimes expecting nothing is the best way to get something. Oh, and try not to have grammatical errors, too.

Step 2. Make it Easy to Say Yes

This is where a salesperson (i.e. me in a former life) will wrongly assume that an action is trying to get them to buy your shit, or setup a meeting with you or allow you to vomit into their ear-drums for 30-minutes. That’s not an action, that’s a pitch, and people hate pitches because they’re complete and utter bullshit and a product of the paleolithic era. Don’t be that guy/girl.

An action shouldn’t be a sales-pitch: it should be a simple question or proposal, that would cost them more time or energy to ignore than to respond to.

In my email with David Cohen, I invited him (and his team) at TechStars to an event that I was co-hosting (as of a few weeks ago).

It was a simple, but sweet offer (and something that he ultimately looped his team in on).

But here’s a better idea: offer insight/ideas totally for free.

Mel Robbins is a speaker and has a TEDx talk that went viral years ago about activation energy. Immediately after watching her talk I decided to reach out to her.

So I sent her this (admittedly long-winded, probably a little obnoxious) email:

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And then, from her assistant, I got this response:

Screen Shot 2015-09-03 at 8.13.06 AMBreakdown:

  • My subject line kicked ass. It’s from her TEDx talk  — in that talk, she suggests marrying an action, and immediately after watching her talk, I did just that. It worked, obviously.
  • Sometimes unsolicited advice/tips work, especially if you know what you’re talking about (sometimes I do, most of the time I’m talking out of my ass) and they have a clear pain point, and you seem like somebody who could potentially address it.
  • Make the notion of talking to you/hiring you/consulting with you easier to implement than the suggestions you just gave them. And make sure your ideas aren’t complete garbage. In this case, hiring me likely would have been much easier (and probably less expensive) than implementing the changes themselves. (And we didn’t ultimately work together, but, that wasn’t the point, as I admitted to her assistant. No, I’m not a Squarespace developer.)

Step 3. Start Small (And Expect Nothing)

I recently read the amazing, totally mind-blowing book about the difficulties of entrepreneurship by Ben Horowitz, The Hard Thing About Hard Things, and I immediately knew I had to send him a note.

So I sent him an email with the subject line ‘Holy s**t that was good’, sounding off about how shit-your-dick awesome I thought his book was, and how I wanted to give signed copies to pretty much everyone I knew.

Not a huge ask — in fact, most people would be totally flattered by the request — but he’s an extraordinarily busy guy, I’m sure, and is probably bombarded by emails from aspiring entrepreneurs on a daily basis who ultimately want his time or his money or tiny pieces of his soul.

Here’s the email:

Screen Shot 2015-09-02 at 9.27.14 AMBreakdown:

  • If they’re a published author (and you legitimately enjoyed their writing), ask for a signed copy of their book. Easy enough. Most people have copies on-hand at their office, and are likely more than willing to send you a few if you have a good enough reason.
  • Start small (this one is more medium-sized). In this case, you’re goal, initially, is to start a relationship. To create a dialogue. If you want funding/a contract, first get them to trust you.
  • Expect nothing. Easiest way to avoid getting sad/depressed when people don’t get back.

I’ve packaged these templates together in one convenient spot (too long for this post): Click here to get instant access to the exact templates I use.

Other Important Things to Consider

When connecting with people, there are a few super important things to consider that will ultimately determine whether or not you get a response to your message:

1. What volume of messages does this person get?

Some entrepreneurs, celebs and super-famous people that you’ll be trying to connect with get way more than a few emails a day from strangers. Siri estimates that she gets in the hundreds. Brad Feld, a ton, too. Mel, I’d imagine, gets dozens a day just from her TEDx talk. James Altucher, between his LinkedIn, email, Quora, Twitter and the rest of his social media channels probably gets hundreds, too.

Simply put, the higher the volume of inbound messages they receive, the less likely they are to respond to a question or request from you. Keep that in mind when writing. It might take them a week or two to get back to you. They might never. Don’t get dissuaded if you don’t get a response. 

2. How big is your ask?

There are two sides of the spectrum you want to ultimately fall on: either a relatively small ask — i.e. answer this one question for me? — or a huge, gargantuan one (that’s extremely valuable to them). Asking them for 30-minutes of their time is a pretty huge ask — most of these people are busy as is. Now, asking them for 30-minutes of their time so they can sound-off about a cause they’ve written about and is pretty close to their heart so that they can ultimately help you raise a shit-ton of money for said cause, that’s a lot better.

3. WIIFT (What’s In It For Them)?

If what you’re sharing with them isn’t enlightening in some way, aligns with something they’re passionate about, is an opportunity for press (and you’re not a baby media-mogul like me) or a chance to connect with some awesome people in a community that they’re an active member of, chances are the answer will always be no.

Even if it is: most of these people are way too busy to say yes to everyone; they don’t know you, you’re a random nobody; you still sleep with your mattress on the floor and you’re 25, grow up, etc.

Don’t take it personally if they say no. Or they don’t get back to you.

Just reach out to more people.

Lastly, my exact templates/examples of other emails: Click here to get instant access to the exact templates I use.

  • Wow, I love that you included the actual messages in this article. It’s always easy to tell someone these are the steps for a successful email, but you show it in action. You’re connection with Mel Robbins was my favorite and I really want to try this now for my day job. Thanks for sharing.

    • Mike Kilcoyne

      Thanks bro!