New Email Inspiration:
May 25, 2020 - Interviews

How Derek Sivers answered 6000 emails in 10 days

Derek Sivers (@sivers) is an author, musician and entrepreneur famously known for founding CD Baby. What started as a hobby, turned intro an independant music juggernaut helping over 150,000 musicians sell $100m worth of music.

This interview was taken from my Yo! Podcast interview with Derek Sivers:

[Rob] Is it true you recently answered over 2,000 emails in 48 hours?

[Derek] Yeah, and 6,000 in 10 days.

[Rob] Wow. So I’m fascinated by this firstly because of the personal human connection here is incredible. When I told people you were coming on the Yo! Podcast, they replied, “Oh, rad, Derek emailed once back in the day.” But secondly, I’m fascinated by how the hell you did it. For context, for the listeners out there who don’t know what went down, Derek sent a simple text-only email to his mailing list at the start of the pandemic simply asking, “Are you okay?”

[Derek] I did.

[Rob] …and you received 6,000 emails back. Have you coded your own email clients? Are you using brilliant macros?

[Derek] Well first, yes to both. I did write my own email client in the PostgreSQL database using Ruby and Sinatra on the front end. But I’m a nerd like that.

And then yeah, I do have 25 macros for my top 25 most used sentences, I have them mapped to keys [using the backslash]. So that’s with my right pinky. And then usually I’m able to answer most emails in under five seconds. I just kind of quickly read, send.

So that’s how I’m able to answer hundreds a day. And I enjoy it. I really love the connection, I love hearing from people. I spend a lot of time in solitude just writing, so it’s exhilarating to connect with 500 people in a day, and have 500 people’s lives and words coming through my screen, through my eyeballs, into my mind.

Because with every one, I have my email client set up like a [Customer Relationship Manager]. For every email that comes in, I also see on the right hand side of the screen, who this person, where on earth they are, their first email ever to me. Just my history of this person on the right hand side of the screen.

So every email that comes up, even if they’re just sending me a sentence like, “Hey, man, good to hear from you. All is well,” sometimes I look and it’s like, oh, whoa. That was an email from the second guy that ever sent me his music to CD Baby back in 1997. Cool, Dennis, how are you man?

[Rob] …and they’re blown away?

[Derek] Yeah, but I am too. Because it’s like, whoa, blast from the past. Yeah, by sending out that email, I was hearing people that maybe I met a conference once in 1998, or slept over at my house in 2005. That’s why I was sending this email to everybody. It’s like, these are my people. I know a lot of these people. I mean some of them are just anonymous people who signed up to my mailing list, or left a comment on my site. But a lot of them are people that I have a connection to. Yeah, it’s worth it to me.

[Rob] Incredible. You mentioned, on your website,, there’s no analytics?

[Derek] Oh, God, no.

[Rob] So do you have any data from these email sends? Are you tracking list open rates, click rates, what emails are working, what aren’t?

[Derek] No, no, no, no, none of that, no. No, there’s no hidden trick. I don’t send HTML emails, there’s no little hidden pixel or anything. No, it’s just plain text.

[Rob] What are you using to actually send the list?

[Derek] My server.

[Rob] Wow, amazing. I know that in that send that said, “Are you okay?” you started with your first name in the email subject, and I reckon that hit a heartstring.

[Derek] Well to me that’s just good manners. Like once a year, I get somebody who’s offended by that. Like, “It’s not really okay of you to use my name. It’s not like we’re old friends or something.” But to me, it’s just good manners.

[Rob] I thought it was classy, serious.

[Derek] Thank you. I’ve been doing that since the ’90s, like to all my CD Baby customers. Actually I got a whole chapter on that in my book, about how I used to do these things. Because I was sending the emails directly from the server, I would actually munge the from address, so if I were sending you a CD Baby confirmation email, it would say that the from name was “CD Baby Loves Rob.” And Tracy would get one that says the from was, “CD Baby Loves Tracy.” And I thought well, come on, it takes one line of code to do that. It’s fun. It’s funny. Why not?

If you are enjoying this conversation, don’t miss the rest of the Yo! Podcast.

Much love,

Twitter: @robhope