Dear Matt - How your email to me could have gotten a response

Hey Matt- 

You're trying to reach out to a lot of people and I am one of them, but you didn't say anything personal about me or our company. Nothing in the FOUR sales emails I have ignored (the ones where you said, "Don’t mean to be a bother here") was actually personalized to me. You could have at LEAST talked about WePay since it is a YC company like mine. Instead, you're using ToutApp to pester me without unsubscribe links.

It's time for us to have a talk.

Your email seriously degraded my impression of you and your company. I'm gathering mental momentum behind the idea that my success depends on ignoring you repeatedly.

It would not be charming if you snapped a picture of your billboard and emailed it to me.

image credit

You have the tools, so sending this is a much better idea:

Don't stop. You wield a holy weapon and that weapon's name is "merge field".  I want to be paid a database-driven compliment. I am pleased that you mined Crunchbase to find me.

A/B testing is just a game. You're not playing games, you're mutating grammar with genetic algorithms. You've got that black hat machine learning guy. Let's be frank, you're solving the hard problems worth solving. You invented this dark pattern (this one weird trick) that hauls 'em in.

Now for the coup de maître: automated follow up. I'm a lead, and since I didn't reply, I'm desperate to be nurtured. Squeeze me a little drip email of that sales honey.

I just wanted to follow up to see if you received my email below.

Hit me again with that madlib sugar.

I know how busy things are at    Poll Everywhere, Inc    .

Remember, you don't need unsubscribe links. This isn't a newsletter! You're just reaching out. I shouldn't be so butthurt about it. You just earnestly thought I could benefit from your product. You were trying to bring me an opportunity for partnership

Let me drop the sarcasm. It goes beyond your word choices -- the entire experience is a euphemism. You're softening your emails with a synthetic personal touch, and you do that as an attempt to avoid the unpleasant truth that you're just another bulk-emailing asshole.

. . .

The lecture is over. The lesson is that you converted me from neutral to detractor. I now dislike you and the brand you represent. I'm speaking strongly about my reaction, and most of your prospects will never tell you when they feel the same.

This blog post is a ruse. It's not actually written for you, it's written for your kind. It's a deception of the same kind you sent me. The custom message at the top will change next week when I send it to the next clever salesperson, BD-er, or "Success Associate".

I'm not opposed to personalization or drip emails. My company sends them after a user signs up to try our product but doesn't succeed. The critical distinction is that you're doing cold outreach. I haven't shown any interest in you. 

Here's the solution: I was taught how to write an excellent prospecting email. It's 3 lines that include:

  1. Why you
  2. Why you now
  3. Call to action with an open ended question

I like Rainforest. Here's the prospecting email I would send to myself:

Jeff -

I saw your last blog post about the A,B,C keywords; that gif is clever.

If you're releasing big features that fast, are you using a mechanical turk / minority report QA tool?

Who's in charge of quality at Poll Ev?


An engineer might notice that this approach is like hashcash for sales. 

I hope this helps you. Please don't contact me again, even if you feel this was helpful. Life is too short to spend time on those who are unwilling to spend time on you. Like me.

Thanks for reading, I hope to meet you soon!


*"Wait, wait. I sent that email only to you! I promise this wasn't a mass email." That's even worse because it means you totally screwed up the dress code. You came to a barbecue in an IBM blue suit.

IBM Blues

Or perhaps it's more like your email showed up with the just-got-outa-bed-hair look. It looks like you didn't put any effort in when you actually put a lot in. Impersonal email just smells like mass email.