The Devver Blog

A Boulder startup improving the way developers work.

Using Ruby to Send Update Emails to Our Mentors

At, we send out weekly email updates to an awesome set of mentors. We do this for a number of reasons. First and foremost, we get valuable feedback and advice from our mentors on a variety of issues. But it’s also an easy and effective way to keep us on track and even maximize our chances of success. As Paul Graham says in How Not To Die (he was talking directly to YC teams, but you’ll get the idea):

“For us the main indication of impending doom is when we don’t hear from you. When we haven’t heard from, or about, a startup for a couple months, that’s a bad sign.

Maybe if you can arrange that we keep hearing from you, you won’t die.

That may not be so naive as it sounds. … [The] mere constraint of staying in regular contact with us will push you to make things happen, because otherwise you’ll be embarrassed to tell us that you haven’t done anything new since the last time we talked.”

Foodzie started emailing their mentors early in the summer. We actually borrowed (stole) their email format and best practices.

One thing we’ve tried to not do is send out a completely generic email to all our mentors. Depending on the content and the interaction we’ve had with a specific mentor, we’ll adjust his email accordingly. We begin each email with their name and send it directly to them (in other words, we don’t put a huge list of addresses in the To, CC, or BCC fields). We do this because we can tailor it and it helps elicit individual responses from each mentor (it’s easier to ignore a question if it’s sent to a group).

But, of course, sometimes the emails to a few mentors can be identical. In this case, my not-so-well-kept secret is that I just use a simple Ruby script to send out a duplicate email that appears to be hand-crafted (or at least copied and pasted).

I’ve been told that Outlook can perform this functionality easily, but I don’t know of any way to do this within Gmail. If there is, let me know so I can feel a little silly (in any case, the Ruby code was fun to write).

To run this code, you’ll need to install the highline gem. You’ll also need to add your Gmail account, recipients, subject message, etc. Finally, you’ll want to put your message inside a separate file within project directory. That way, you can easily modify, spellcheck, and format to your heart’s content before sending.

You can get the entire gmailr source code (all two files!) at Github. Please use this script for good, not evil – no one likes a spammer. Enjoy!


Written by Ben

January 20, 2009 at 3:46 pm

One Response

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  1. Borrowing is not stealing as the RIAA wants us to believe.

    Instead of: Borrowed (stole) you should write Borrowed (copied) or Borrowed (used)


    January 21, 2009 at 1:12 pm

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