Derek Sivers

Interviews → Cold Email Outreach / Jeremy Chatelaine and Jack Reamer

Tips on connecting with people through email.

Date: 2020-04

Download: mp3



I’m Jeremy, founder of Quick Mail.


I’m Jack from

We’re very grateful to have Derek Sivers on the show today. Derek is the most creative human being that I have ever come across in my life in terms of raw output and high-quality work. We’re here to talk to Derek and how he connects with people primarily through email.

Derek, welcome to the show, man.


Thanks, Jack.


You are the first and only author I have ever encountered who actually has their email address listed on the final page of the book. Why do you include your email address as opposed to authors who link their social profiles like Twitter?


Why I don’t use Twitter to communicate? It’s similar to when you hear stories of people who lived through the Great Depression and then never again for the rest of their lives or their children’s lives ever threw out a piece of food because they lived through that.

I got online in 1994. I went through the first dot com boom and bust. Many people were completely dependent on certain companies like MySpace or Every single musician not just had a MySpace page but depended on it. They actually built their Myspace URL into their album artwork.

When MySpace crashed, many artists lost their entire fan base. So, I would never depend on a company’s platform for people to reach me. I would never use Twitter or anything else to say, “This is where you can find me,” because we don’t know what’s going to happen. Twitter or Facebook could go out of business this year.

If that happened, the way that most people connect would be gone. It’s unlikely, but it happens. That’s why I only ever send people to my website and email address because that’s a non-commercial thing that I control.

As far as why I want people to contact me? Technically, I’m retired. I sold my company 12 years ago. I haven’t done anything for money in 12 years. These days, my currency is meeting and knowing cool and interesting people. It’s my favorite part of what I do.

I love when I get an email from a guy running a banana plantation in Ecuador and the next email is from an investor in Lebanon. I always think, “How cool that I get to meet these people! I love hearing from strangers around the world.”

I was interested in doing your podcast because that’s our topic of conversation today, too.


While we’re on the subject, how do we get a hold of you?


Go to You’ll see a big link that says “Contact” and you’ll see my email address out in the open. I’m not worried about spam and I ask people to introduce themselves. You don’t have to have a question for me. Just say hello and introduce yourself.

Nobody has ever asked me about cold emailing. It’s a fascinating subject. I have so much to say about it.


You mentioned that you’re retired and that your currency is connecting with other human beings. Is it just a hobby? What do you do with those connections that you make?


I don’t think of that as a means to an end. I think of that as THE end.

If you reverse it and talk about money, you could ask,

“Why do you want to be rich?”

“So that I don’t have to do work that I don’t like.”

Money is more of a means to an end. But people to me are the end, not the means.

Rarely my connections lead to much more than an email in the inbox.

I’ll contact someone if I loved their book or music or work. I’ll find a way to contact the author or the creator and say, “Holy shit. That was brilliant. I loved it. This was amazing. Count me as a fan.”

I’ve done this about 20 times. I never got a response only once or twice, but the rest responded warmly. Many of these people have turned into friends. We actually call each other on the phone and shoot the shit. A couple of them have even turned into best friends.

Many of my current friends are people that cold emailed me after hearing one of my interviews, or TED talks, or reading my book. Most of them emailed out of the blue and introduced themselves and said, “Wow, you’re really interesting.”

Then we traded some emails back and forth and I said, “We should talk on the phone.” It’s one of the coolest things to me that I have friends around the world that I’ve never even met face to face, but we’ve talked on the phone every week or two for years now.

I have friends that live in Lithuania, Hong Kong, Australia, and many places that I haven’t even visited. Four of those have actually turned into romances. I like getting emails and turning them into actual relationships.


Relationship building. That’s what it’s all about.


You have a lot of relationships through these emails. Do you need more? We only have 24 hours in a day.


Right. [Laughter] No, I’m not a mad socialite. But friendships come and go in life. I don’t know about you, but there’s people that I was friends with two years ago that I’m not really friends with anymore. Friendships come and go, and then new ones come in.


Let’s say I just finished a book that was a fabulous read. Do you always reach out to the author via email? Do you have any type of format for how you reach out?


In preparation for our conversation today, I prepared my top five tips. I’ll run through them quickly first and then we’ll elaborate.

1. Only ask one question. Asking zero questions is OK. 2. Don’t be too succinct. 3. Show them who’s talking and show your worth. 4. Switch to voice if it’s mutual. 5. Never ask if they will mentor you.

Now, I’ll elaborate on each point.

1. Only ask one question. Asking zero questions is OK.

When you asked how I usually reach out to people that I admire most, I find their email address and I tell them, “Oh my God, I loved your book. This is brilliant writing. I just want to tell you what a huge impact it had on me. I read a lot, and this is one of the best things I’ve read in years. I just wanted to say thanks and count me as a fan.”

That’s it. No question. No burden on them. A lot of people love hearing that. If it’s anything short of some worldwide superstar Oprah level person, most people are going to be really happy to get an email like that.

And if you do want to ask a question, then only one. I hate it when I get an email and someone says, “Hey I liked your book. I have six questions for you.”

I think, “Really? OK. This is the next hour of my life.”


I want to crystallize this to the audience out there. Derek, you’re reaching a lot of people and you probably get more of these outreach emails than anybody else we talk to on this podcast. We’re really listening when you say don’t overwhelm someone with questions.


If you’ve ever received any email from me, it was sent from my own email client that I wrote myself. I keep track of exactly how many emails I’ve received from people and how many I’ve sent. It’s all in my database.

I’ve answered something like 85,000 emails from 65,000 people over the last 11 years. It’s intense. In March, because of the start of the pandemic fun, I sent an email to everybody in my mailing list saying, “How are you? Yes, that’s a real question. I really want to know.”

7,000 people replied in two days.

I read and replied to all 7000 emails in 12 days. I’m not exaggerating. It took about 16 hours per day, but I did it. I would wake up at 6 A.M. and start typing until midnight and then I would sleep for six hours and do it again until they were gone.


Can I say thank you on behalf of those 7000 emails? I was one of them and it was really cool to hear back from you. Nobody does that. We appreciate it.


It’s fair to say that I know a thing or two about emailing people [laughter].

Let’s move on to tip number two.

2. Don’t be too succinct.

Some people try to be considerate. They dispense of all human greetings and they bark out a question.

“Hi, Derek. Love your book. What’s the meaning of life? Thanks, Dave.”

I get what Dave is trying to do. He’s trying to not waste my time, but I look at that and think, “What the hell dude?”

But on the other hand, some people email and tell me their life story. I’ll look at an email that goes on for pages and think, “Oh my God. Are you serious?”

They’ll say at the end of the email, “This took a couple hours to write, but it was very cathartic. Thank you.”

So, the best is in between. Have some personality and mention something memorable. You’re actually doing the recipient a favor. For example, “I’m writing this from a tree fort in New Mexico right now where my feet are dipped in a pond.”

Write a few words that make it different from the average email.


When I wrote to you, I said I was having a baby in a couple days.


Exactly. I call it humanizing the inbox. For example, if somebody doesn’t tell me where they are, it’s one of my first questions. I get an email from Carlos, and I’m say, “OK, I’ll answer your question, but who are you? Where are you? Are you writing from New York City or Patagonia? Give me some context.”


In the early years of my business, Quick Mail, I was travelling a lot and answering a lot of support questions. I would send people a photo and say, “This is what I’m looking at in Berlin. I’ll get back to you in two days.” People loved it because it’s so human and so relatable.


That relates to tip number three.

3. Show them who’s talking and show your worth.

Introduce yourself and show your worth. Flaunt your credentials. Successful people like knowing interesting and successful people.

First, talk about whether you’re successful or not. Have an email signature with your URL. It’s ideal if you have your own website. Even if you only have a Twitter or Facebook URL, include it because the stranger receiving your email might want a little more context.

I’m amazed at how many people have no email signature. Ideally, you could also include your location. It’s cool to see if someone is in Rome or Beijing.

When I ask people for more context about their lives, the most common response is, “I didn’t want to include any URLs because I didn’t want you to think I was being self-promotional.”


If you’re about to reach out to someone you admire, how do you rationalize sending URLs?


It’s considerate to give the person you’re emailing a little more context about who you are.

You’re not self-propagating. You’re just giving me a little context of who I’m speaking with. Because in regular human physical world, if somebody’s speaking to you, you can see them and get that context.

If you’re in the real world and suddenly there’s a voice coming out of a tree saying, “I have a question for you.”


I’m thinking, “Who are you? Where are you?”

You have to understand that it’s human nature to want to know who we’re speaking with.


Any particular type of context that you like to read in an email?


Minimal involvement. Don’t miss understand this to think that you should send a video as your first cold call email. This almost never happens, but about once a year, I get some nut who will send nothing in the body of email except, “Hey Derek. I’m sending you a video for you to watch.”


Too much.


That’s interesting because for some people, video is a great medium.


Maybe it’s because they don’t understand the quantity of emails I get. I try to get through 100 emails per hour. I answer most emails in under 20 seconds each. If you send me a seven-minute long video attachment, I think, “I might as well stop for breakfast and eat a meal while I look at your video. If you put whatever you’re saying in the video into plain text in the body of an email, I could have read that in 30 seconds.”

There have been times if I’m busy, I reply, “I’m sorry I don’t have time to watch this. Can you please reply.”


You would prefer for someone to send you a small blurb and then say, “If you want more information, or if you’re curious about it, here’s a link to the full video.”


Exactly. Like I said, show your worth influent your credentials. A few URLs in your email signature are ideal because it’s not forcing somebody to watch a video or listen to an audio clip, but it’s there if people have time and want to check it out.

Lastly, if you have any accolades or credentials, now’s the time to mention them. If I get 100 emails and one person tells me that they’re the World Champion of the 2018 World Technology Award or the first person to ever climb this mountain, I’m going to pay a little more attention to that email – even if it’s the winner of a local high school backgammon championship.

Aim for anything that sets you apart from the rest.


How many emails do you get from people who overdo the self-promotion?


It’s not that big of a problem. If someone were to include three paragraphs ranting about themselves, it’s easy for me to skip those three paragraphs and get to the question at the end.


The lesson here for everyone listening is that people really don’t care about you, it’s all about them. I don’t mean that in a negative way, but if you want to capture someone’s attention and get a reply, you need to spend the majority of the email focusing on your recipient. Would you agree?


Yes. But don’t forget the previous point, which is don’t be too succinct.

I want to hear something colorful about you. Humanize the inbox. If I only get questions with no context, no personality, no feet in the pool, then it’s boring to me. It’s tedium.

When my emails turn into friendships, it’s usually because their first email to me is so jaw-droppingly interesting, even if it was totally self-indulgent.

For example, I just got off the phone with my friend who lives in Australia. She sent me a long, long, long email on Christmas Day, the day after breaking up with her boyfriend. They were travelling in Prague.

They broke up and she sent this long email that said, “I’ve been walking around Prague for three hours in the snow, listening to your voice in my headphones. It really got me through a difficult time. Thank you.”

I don’t even think she had a question. In the final paragraph, she mentioned some accolades and said, “Guess I should tell you something about who I am. . .”


Here’s my phone number and credit card details [laughter].


Very quickly she said, “I’m a scientist who happened to be in Fukushima when the earthquake hit. I’ve done some work in Vanuatu helping people there. Now I’m getting a Ph.D. in biology in Melbourne, and I’m traveling the world because I met a German guy.”

I thought, “OK now we’re talking!”

I replied, “Give me your phone number. Let’s talk.”

That leads us to point number four.

4. Switch to voice if it’s mutual.


You’ve made a really good case for talking a little bit more about yourself. I’m ready to back up on that approach of making it all about the prospect because people often reply because they like your backstory.


It’s also for your own interests. You want to be entertained. You can’t really be entertaining someone if you’re only asking them questions.

Do you answer all your emails?


Yes. Every single one.


What do you do with spam emails or emails that are obviously not taking you into consideration at all?


I almost never get those. The obvious ones are when somebody says, “I am a content creator and I would like to create some content for your website. Will you post my articles on”

I know those are bulk emails because if anybody looked at my website for one second, they’d know it’s very non-commercial. I don’t do that. There are no ads. So, I delete those.

But every other email I get is usually from somebody who’s read my book, watched my talk, or likes my other work. I don’t really get pure spam. I delete those because I don’t consider those personal communication. That’s not what we’re talking about. That’s a list of bloggers that blasted it thousands of emails out. That doesn’t count.


What’s your rate of actually giving your phone number to someone you meet over email?


A few times a year. I only do that if it feels like we’re going to be actual friends.

For example, Mark Manson, who wrote The Subtle Art of Not Giving a Fuck, he’s one of those people that I cold emailed and said, “Dude, I fucking love your writing. You’re one of my favorite bloggers.”

He replied back, “Oh my God, I love your writing. We should talk.”

Mark and I talked on the phone a couple times, then found out we were going to be at the same conference in Bangkok, hung out all night at a conference and have been friends ever since.

On the back of his bestselling book, there’s a quote from me, which I honestly forgot about. I was really flattered. I saw his book in the airport bookstore once and thought, “Awww, it’s Mark’s book.” Then I looked at the back cover and my name was there. I thought, “Oh right. I’m on the back of Mark’s book.” [Laughter] Anyway, Mark came to London a couple months ago and we hadn’t seen each other since before his book exploded and sold over 10 million copies.

We were talking about how he’s dealing with exploding fame. He said, “I don’t mean to sound weird. You and I both have connections to India. But what is it about people in India that are so presumptuous? Do you get these emails from Indians, too?” And right away, I knew what he was talking about. There’s a cultural thing in India. I don’t know why, but Mark and I both get emails from strangers from India all the time that say, “Hello, my name is ___. I really need help figuring out the meaning of life. Here’s my phone number. Please give me a call.” I thought it was just me. I have never heard anyone else talk about this.

When I say switch to voice, if mutual, I mean don’t cold email a stranger for the first time and say, “Call me.” You can tell when it’s a mutual beneficial thing.

The Australian woman who emailed me from a snowy bridge in Prague after having my voice in her headphones for three hours, I thought, “OK. You sound really interesting. We should talk.”


Be interesting and excite your recipients, right?


Somehow. Yes. Light the fire in your recipients.

Jeremy, you asked at the beginning of the conversation about why I email all of these people and it stumped me a bit.

I realized that there’s one other aspect to this. I keep track of where everybody is. I always ask, “Where are you?” If somebody says, “I live in Helsinki,” I’ll say, “Oh cool. Helsinki is a really interesting place. I’d like to visit someday. I’ll let you know if I do.”

Sure enough, about three months ago, out of the blue on a Sunday afternoon, I said, “I feel like going to Helsinki.” That night I hopped a plane to Helsinki from London. When I arrived, I looked in my book to see who I’ve emailed from Helsinki. I contacted about four people that emailed me and seemed to be pretty cool, interesting people. I said, “Hey, I’m in Helsinki for three days. Let’s meet up.” The next day I’m sitting in my underwear in a sauna with some dude that had emailed me.


So cool. Well, I’m in Switzerland [laughter].


I really want to go to Switzerland someday! I read a whole book about Swiss culture, but I’ve never even been there.

Back to point number 4, switch to voice if mutual means that if you can tell that there’s mutual interest here, take it to the next level. I’m assuming most of us spend too much time at the computer typing and sometimes it’s really nice to switch to the phone.


How do you make that transition to a phone conversation?


I’m usually the first to say, “Hey, let’s talk. Here’s my phone number, call me.” Simple. That’s it. Some people say “no,” or some people say, “Oh, yeah. We should totally talk someday.” But they don’t follow through. Some people aren’t phone people and that’s alright.

That brings us to point number five.

5. Never ask if they will mentor you.

This one to me is a little bit like the India example I gave. Almost every month, I get an email from a stranger. They say, “Hey my name’s ___ and I’m really trying to figure out what to do with my business. Will you be my mentor?”

There are levels of engagement that you can have with somebody. If marriage is at the top, mentorship somebody is a little below marriage. It’s not for a stranger to ask coldly in an email.

Could you imagine? “Yes, stranger, you are now beholden to me. You will follow my guidance.” [Laughter].

I have no interest in mentoring. But if you ask me a question by email, I will answer it. When people ask if I will mentor them, I say “No. But what do you want to know?”

Ask your question instead of making this some weird official mentorship relationship.

On that note, before you ask a public person a question, it’s really important to read through that person’s public output first. That’s common decency. The answer to your question may already be out there in a book or an interview. And it’s not the recipient’s obligation to provide you with the answer that you’re too lazy to go find out for yourself. It’s your job to find it, not their job to repeat it to you.


I wrote this post once about how to find a mentor.



That’s the one. Thank you. Seth Godin and I are somewhere between friends and acquaintances. He published my first book and we’ve hung out and talked a lot. But when I have a question for Seth, it’s tempting to email him my question.

But every time I think about doing this, I stop for a second. I think, “Seth’s a busy dude. I’m sure he’s probably mentioned this somewhere he’s writing.” Now it’s my obligation, even if it takes me an hour or two to go skim through my Kindle books or search his blog to see if he’s answered my question.

Almost every time, sure enough, he’s already mentioned this or something close to it. I end up not emailing him after all, except to say, “I just wanted to thank you for your ongoing inspiration.”


Very cool.

At what point do we want to keep following up if we don’t get that initial reply from a cold email? What’s your take on following up?


Follow-up is counterintuitive because persistence is polite. If you’re in high school and you have a crush on somebody and you text them and they don’t text you back, take a hint. They’re not into you.

We learned that lesson painfully as teenagers. If somebody doesn’t reply, that means they’re just not into you. Let it go.

But in a professional world, when people are busy and swamped in communication, especially if you’re emailing them, which is less personal than a text or a phone call, being persistent is polite.

Imagine these two scenarios:

Scenario one, you email somebody, and they never get back to you. For the rest of your life, you curse them as an asshole. You decide that they’re a jerk and mean you’ll tell anybody that will listen that that jerk never got back to you.

Scenario two, you email somebody, and they never get back to you, but you give them the benefit of the doubt. A week or two later, you email again saying, “Hey, I emailed you a week ago. I never heard back from you. I have this question. It’s really important, if you don’t mind.”

If they don’t reply back a second time, maybe you try one last time or find another way to reach them. Maybe they don’t check their email, but they check their Twitter. Try one more time because it’s considerate and polite to assume that they’re busy. Give them the benefit of the doubt. That’s generous. It’s polite to persistently follow up.

I’ve been on the receiving end of that. When I was at my busiest running CD Baby, there were a couple of times where somebody emailed me, and it took them four times to get in touch with me because I was just swamped. I really appreciated that that person didn’t take it personally and kept following up.

By the time they said, “This is my fourth time, I’m still trying to get in touch with you.”

I’d say, “Ah, right. Sorry, I’ve been swamped. But you know what? You’re right. This is your fourth time trying to reach me. I’m going to stop what I’m doing right now and give this my full attention.”

I thought that was really sweet and polite of them.

I have another fascinating story about this. Years before my CD Baby days, I was a musician in New York City promoting myself. I went to go hire a publicist. The publicist that I wanted to work with was like the hottest publicist in New York City at that time. Everybody in the music business wanted to work with her.

The only way I could even get an appointment with her is because I contacted the local music magazine and asked if I could do a freelance story for them about her and they said “yes.” So, I contacted her as if I was employed by the magazine.

That’s why she said “yes” and agreed to meet with me.

I did actually do an article on her for the magazine, but that’s how I also got in her office and able to find out how she works.

I asked her, “How does a musician get your attention?”

This was before everything was digital, so people were still sending physical packages. I’m referring to an inbox as a physical thing.

She showed me three big boxes in her office and she said, “Everything that comes in the mail gets put into the first inbox over there. We don’t even look at it. When somebody follows up and says, ‘Hey, I’m following up to see if you received my package,’ then we take that package out of the first inbox and put it in the second inbox and continue to ignore it.

When they follow up a second time and say, ‘Hey, I really want to work with you. I’m following up again to see if you’ve had the chance to listen my package.’ Then, we pull it out of the second inbox and put it into the third inbox.

When we have time, sometimes we go through the third inbox. But usually, people have to follow up a third time to say, ‘This is my third time following up. I’ve contacted you three times before. Have you had the chance to listen?’

Then, I feel that this person showed me that they’re worth my time, that they’re persistent about what they really want, and that this means enough to them to follow up.

A lot of people spam everyone and don’t care enough to follow up, which means they don’t care enough about you if they really, really, really want to work with you.”

Granted, she was the hottest publicist in town. She was completely drowning in people wanting to work with her, but it was an interesting way to see how she dealt with that. It gave me a lot of empathy for people in her situation.


Do you have any tips for people that want to be persistent but are worried about being annoying?


It’s human nature. Give somebody the benefit of the doubt. Don’t be mean or cranky that someone is ignoring you. Tone is important.

If you’re gentle, understanding, and compassionate, politely send a second or third email and don’t get upset about it. Persistence pays off.


Is there anything else about persistence that you’d like our listeners to know about?


Use your instincts to know when it’s a dead end and don’t get too upset about it. Try not to feel rejected because there are times where people are going through crazy life events.

Some of my actual dear friends that are also famous sometimes don’t even reply to my texts. I could get bent out of shape about it, but then I think, “OK, he’s just swamped. Poor guy. He’s too famous.”


You mentioned that it may be helpful to find a different approach when contacting someone. Let’s say you’ve tried emailing three times. Maybe they’re more active on Twitter or maybe you have better luck on Instagram or LinkedIn. Mix up the channels at a certain point before giving up. That’s a good piece of advice.


Exactly. Thanks for mentioning that. I only log into see my Twitter DMs about once a year. When I do, there’s usually a collection of DMs from people that asked me a question nine months ago. Even though it says right there in my Twitter profile that I don’t check my DMs. Please email me instead.

You never know what medium someone is using these days.


That’s a good thing to keep in mind so that we don’t take it personally when someone doesn’t get back to us.

How do you deal with rejection?


I don’t really ask anything of anyone. But if I do get rejected, I don’t let it stick to me too much. I’m a little pessimistic and I never put too much weight onto any one person.

We usually think of rejection more in terms of romantic rejection. If this one person means a lot to you, your expectations on this person are as high as can be. If that person rejects you, that hurts. But if it’s somebody that you were looking forward to talking to and it doesn’t happen, oh well.

I cold emailed one of my favorite authors of all time out of the blue and he replied. I thought, “Oh, my God. Oh, my God. I’m talking to my favorite author!” We exchanged back and forth. I was living in New Zealand at the time and he said, “In fact, I’m coming to New Zealand in a couple months. We should try to meet up there.”

I said, “That’d be great. What day did you want to try and meet up?” He never replied.

He said he was going to be in New Zealand for the book fair, so I knew what week he would be there. So as it got closer to the date, I emailed again and said, “Hey again. Do you still want to try to meet up when you’re here?” He didn’t reply again.

I sent one more tiny email that said, “Hey, I know the book fair is going on. I’m here if you want to meet up.” Never heard back.

I thought, “Eh, whatever.” I hadn’t really thought about it until right now, since we’re on the subject. Maybe I should email him again. It’s been a couple of years.

Don’t take it personally. Assume that people are swamped. I’m on top of my inbox but most people aren’t.

I have a friend and it freaks me out when I look at her phone. Her email icon says 6,000+ unread emails. I think, “How do you how do you look at that number and not get upset by it? Can’t you delete them all?” She says, “Whatever, I don’t even look at it.”

I’ll even email my sister and never hear back. I think, “Why hasn’t she gotten back to me?” She’s bad with email.


I’m hearing that this comes natural to you. Maybe you’ve never put so much weight into getting a reply from one person.

What would you tell a listener if they say, “I really put a lot of time into messaging this person. I followed up properly and I still haven’t heard back from them.”

What would you tell them to take some of the weight off of that?


That’s the wrong approach to life in general. You can’t put too much weight onto any one thing.

Without the obvious example of your kids, you can put a lot of hope into your baby. That’s allowed.

There are even some friendships that you might lean on too much. You can’t put too much weight onto any one person. It’s healthier not to place all your weight on one project or one expectation.

You have to understand that other people have different priorities than you. They are different people than you. They have different values and different things going on in their lives that are more important to them.

Even in terms of business and projects, you have to loosen up and let go of it.


There’s a book that I read called the Four Agreements, and it’s a self-help book.

One of the agreements says to never take anything personally because you don’t have a say in what that person has gone through up until this point that caused them to act in that way. There’s very little that we can actually blame on ourselves for how someone else is behaving.


Rejection is a big part of life.


At, you list all of your book recommendations and summaries.

Are there any new books that you’ve been really enjoying that have helped you recently?


I’m sorry if I’ve talked about this a few times publicly already, but I’m going to do it one more time. I love the book, The Courage to be Disliked. It’s one of the most interesting books I’ve read in a long time.

There was a contemporary of Sigmund Freud named Adler. He didn’t get as famous as Freud, but his ideas on relationships and interactions are fascinating. A Japanese author dug up his work and and turned it into a pseudo-fictional, nonfiction book.

He set up this book as a conversation between a teacher and a student. The title, The Courage to be Disliked, is not really what the book is about. It’s just one of 20 topics inside of the book.

It’s a fascinating book with radically different and interesting ideas on how we relate to the world. It’s the single most interesting book I’ve read in a couple of years.


You personally have a new book that’s on the horizon too. When can I get my hands on it?


I have three new books on the horizon. I have one that is called Your Music and People, which your listeners might actually be interested in, even if they’re not musicians. I’m not saying this to sell a book because I don’t care, but a lot of the topics we talked about today are topics that I’ve talked to musicians about for years.

I was in the music business for 20 years. A friend of mine who’s a direct marketing business person read Your Music and People and thought it was a great marketing book.

He said, “This is totally a marketing book. I have no interest in music, but this is great advice.”

That book is finished. In fact, as soon as we’re done talking, I’m going to finish up programming the store front on to sell my books directly.

My second book is also done. It’s called Hell Yeah or No. It’s a collection of articles about what’s worth doing. I called it Hell Yeah or No because it’s all about the recurring theme of deciding what’s worth doing.

It’s a collection of all the best articles that are already on my site but compiled together with a theme.

I’m still writing my third book. It’s called How to Live. It’s 27 one-sided arguments and one conclusion, all answering the question, how to live.

So that way, you know how to answer those Indian messages now.


[Laughter] Exactly. The meaning of life? I got that down.


You schooled us on the right way to do outreach [laughter]. So, reach out to Derek and use all of these tips that he has kindly shared.

How can our listeners contact you?


Despite everything I said, don’t overthink it [laughter]. Isn’t that the rule with anything?

Learn the rules and then try not to forget them.

Go to, send me an email, and say “hello.” I like hearing from people. It’s fun. I have a mailing list that you can get on, too. You’ll be the first to hear when new things are launched, or you’ll hear from me with private messages like asking if you’re alive.


I was one of those cold emails and I asked you a business direction question and the advice you gave me was really freaking helpful.

Know that you’ll probably be pleasantly surprised with Derek’s reply if you actually reach out and engage with him.


Thanks for telling me that. The sweetest thing I hear by email is when somebody tells me that.

Every now and then, I get somebody that will say, “Four years ago you wrote an article encouraging us to learn programming and specifically to learn JavaScript. I followed your advice and read the books that you suggested. I learned JavaScript, which helped me quit the dumb job I was doing. I got a job as a programmer and now I’m making six figures a year and I’m so happy. It’s all because of that one article you wrote.”

That is the coolest compliment ever. So, hearing that my email advice concretely helped you in some way, that’s really awesome.


Thanks so much for stopping by the show and talking cold email with us.


Thanks, Jack. Thanks, Jeremy. That was really fun.