The Most Successful E-mail I Ever Wrote

2008 blast from the past: me, Mike Wallin, and Derek Sivers, the subject of this post. (Photo: A3maven)

[Total read time: 3-5 minutes.]

Derek Sivers is one of my favorite people. He is a programmer who lost his stage fright by doing more than 1,000 gigs as a circus ring leader (!!!).

He’s also a musician who founded CD Baby in 1998. As of December 2009, CD Baby had the following stats as the world’s largest online distributor of independent music:

– 300,000 artists

– 5,339,025 CDs sold online to customers

– $200,000,000+ paid directly to the artists

Derek sold the company in 2008, and he did so in a most unusual fashion (bolding mine):

Sivers sold CD Baby to Disc Makers in 2008 for what Sivers has reported to be $22 million, bequeathing, upon Sivers’ death, the principal to a charitable trust for music education.; while alive, according to Sivers, it “pays out 5% of its value per year to me.”


I know this to be true.

Stranger still, at its largest, Derek spent roughly four hours on CD Baby every six months! He had systematized everything to run without him. Derek is both more successful and more fulfilled because he never hesitates to challenge the status quo, to test assumptions. The below guest post from him illustrates this beautifully.

Without further ado, the most successful e-mail he ever wrote…

Enter Derek Sivers

When you make a business, you’re making a little world where you control the laws. It doesn’t matter how things are done everywhere else. In your little world, you can make it like it should be.

When I first built CD Baby, every order had an automated e-mail that let the customer know when the CD was actually shipped. At first it was just the normal, “Your order has shipped today. Please let us know if it doesn’t arrive. Thank you for your business.”

After a few months, that felt really incongruent with my mission to make people smile. I knew could do better. So I took 20 minutes and wrote this goofy little thing:

Your CD has been gently taken from our CD Baby shelves with sterilized contamination-free gloves and placed onto a satin pillow.

A team of 50 employees inspected your CD and polished it to make sure it was in the best possible condition before mailing.

Our packing specialist from Japan lit a candle and a hush fell over the crowd as he put your CD into the finest gold-lined box that money can buy.

We all had a wonderful celebration afterwards and the whole party marched down the street to the post office where the entire town of Portland waved “Bon Voyage!” to your package, on its way to you, in our private CD Baby jet on this day, Friday, June 6th.

I hope you had a wonderful time shopping at CD Baby. We sure did. Your picture is on our wall as “Customer of the Year”. We’re all exhausted but can’t wait for you to come back to CDBABY.COM!!

That one silly e-mail, sent out with every order, has been so loved that if you search Google for “private CD Baby jet” you’ll get over 20,000 results. Each one is somebody who got the e-mail and loved it enough to post on their website and tell all their friends.

That one goofy e-mail created thousands of new customers.

When you’re thinking of how to make your business bigger, it’s tempting to try to think all the big thoughts, the world-changing massive-action plans.

But please know that it’s often the tiny details that really thrill someone enough to make them tell all their friends about you.


TIM: Do not miss Derek’s blog, which is full of these gems. It’s one of the few blogs I take the time to read. If you want to see how Derek and I compare approaches, here is a starting point.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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105 Replies to “The Most Successful E-mail I Ever Wrote”

  1. Dude, I love your posts, but please do not wear short-sleeved shirts! In Europe at least, it’s a definite no-go!

      1. You are right there, here the locals just wear them to stop getting sunburnt

    1. I am wearing a short-sleeved shirt right now and 50 chicks are loving it screaming and crying. As I am typing this. True story.

    2. I’m wearing no shirt and was thinking of putting a short sleeve shirt on to “dress it up a bit”.

    3. Is this an email written by Derek Sivers? This post cracked me up! Haha…

      @Chris Hughes

      I’ve also exchanged emails with Derek before. I think he’s an amazing guy and I like his down-to-earth personality!

  2. That’s so funny! 50 employees check the CD before sending it? Fantastic. Customer service to the max. Great article Tim.

  3. This is truly an inspiring post. First heard of this visionary man in Seth Godin’s Purple Cow.

    This shows me that anything is possible if you work for it.

    Thank you for the blast from the past Tim.

  4. Derek is a great guy. I read his book and have had the pleasure of communicating with him through email. He’s a true model of excellence when it comes to business. He’s also a great example of creating an extraordinary business and going above and beyond with customer service.

  5. Derek Sivers is amazing… few years back, I didn’t know who he was and had signed up for his ebook, unknowingly that he was the founder of CD Baby. He followed up with me personally, asking me what I thought about the book and what I was doing musically. We exchanged a few emails and then I later found out who he was. He truly cares about Indie musicians like myself and because of that, after about two weeks of trying to figure out the best distribution company for my needs, I chose CD Baby yesterday, fully aware that Sivers didn’t own it anymore, but because his DNA was in the company and for that I trust them. Tim and Derek… couple of my most favorite guys… learned a lot from both of you! Thank you sincerely!

  6. It’s the small things that make up the big win. Derek never got stuck “in” his business— he was always on it. As I’ve read before, he is one of the guys who never considered himself a business person. Instead, he needed to do something (sell cds online), did it, and his friends wanted him to do it for them… then their fiends.. then their friends.

    It wasn’t rocket science. It was taking action and continuing to improve how the service worked. This email speaks to who Derek is and how his company reflects his beliefs. He looked at how things were done and asked (continuously) himself how he would like it done… then he did it.

    Awesome. Pick up his book “Anything You Want”

    (free for prime members)

  7. Derek,

    Totally didn’t expect to see you here. I like the sense of humor in the email that lead to thousands of new customers.


    Looking forward to your new book in a few months.


  8. Hello good people,

    I definitely agree with Justin above, Derek’s book “Anything You Want” is gold!! I read it right when it came out. Actually a lot of this post is right out of the book. The book is pretty short and offers great insight, I definitiely recommend it to anyone interested in how to think different about creating a company and making it “your own little universe”.

    As far as Derek goes and as a fellow musician, I really appreciate his artistic taste and creativity. Seems like a great guy!



  9. Unspoken here is the power of continuous testing of approach. I bet an A/B test between the old thank you email and the new one would show higher lifetime value for the customers that received the fun, humorous email. Not to mention the additional value of all of the new customers from the online conversations about the email. I’m sure there are a lot of attempts at being humorous that crash and burn (especially if your customers don’t get your sense of humor), which is why it’s always important to structure a test around those bold ideas. All in all, great stuff!

  10. “Our packing specialist from Japan lit a candle and a hush fell over the crowd…” That’s awesome.

    Tim, what’s up with the 4HWW forums? It looks like they are locked. Have a desperate need to ask for advice and share what I’ve learned with others!

  11. Derek Sivers is easily the friendliest person on this planet. He is very approachable and down to earth and I love his blog. His tips are super actionable and relatable. Thanks for being awesome Derek (and thanks for posting this Tim!)!

  12. Haha! Love it!

    I love when people (and certainly businesses) don’t take themselves too seriously. Life is serious enough. Let just have some fun! We are all in this crazy ride together. Why not enjoy it?

  13. I absolutely Loved Derek’s Book Anything You Want. It was less of a book, and more of a shot of philosophical-espresso and wisdom.

  14. Great, I didn’t know this guy, but bought several times on CD Baby. Thanks, he’s got really good posts on his site!

  15. Great advice. I have used humor to great effect in my emails as well. Making people smile and laugh is a great way to get them to emotionally connect with you.

  16. Nice to see a nice guy making money and giving back. Loved reading this article as Derek mixes great business intelligence with humour, enthusiasm and good ethical principles, another inspiring article.

  17. Wow. Did Derek work any more than 4 hours for a certain period of time while starting the company and getting it rolling etc? if so for how long

    wait, and he wrote a book? name of book please!

  18. Namaste Tim and Derek!

    I am a true fan of derek. Every post he writes makes me think about my life philosophy. There are very few entrepreneurs who lives his lifestyle. Truly down to earth guy and who also loves to strengthen relationship with anyone who makes a move. I keep on reading your interview at Derek’s blog and which i think everyone needs to print out and read when they feel how to design life style. You both guys really rock my world.

    I would like to request everyone to read Derek’s blog and go through the interview section, you will know more about derek.

    Tim and Derek: How about having one great Podcast interview on entrepreneurship, life philosophy, productivity and other interesting topics?

  19. I guess it’s the way he differentiated himself from everyone else that made him successful. Not just making it a business, but being creative, and making it his own made it go viral. And the idea to make that goofy email came from following his intuition.

    I’ve been using a technique called EFT(Emotional Freedom Technique) to clear all the blocks to listening to my intuition to guide me in my own online business/blog. We all have the knowledge, the business intuition within us to help us become rich, it’s just as simple as clearing the blocks to hearing our intuitive, right brain compass.

  20. Love Derek Sivers! I met him at a conference when I was 14 and that’s what got me started on a path of psychology and business books that ultimately led to The 4-Hour Workweek. I’m 18 now, and his blog and your blog are the only ones I follow these days. Thanks to you both for contributing so much to the way I see the world!

    I’ve noticed that you do a great job at finding interesting people to write guest posts. You’re a very interesting person yourself. I understand that you’re busy writing a book right now, but it would certainly be nice to see some more posts actually written by you! The same goes to Derek, actually. I would like to see more posts from both of you, because when it comes down to it I am a selfish person.

    1. Thanks for the comment, Andrew. Once the book is done, I’ll have far more posts written by yours truly. In the meantime, I’ll scour the web (and world) to find the best guest authors to provide great content.

      All the best,


  21. Sounds like great advice. That’s something I have to work on for my sites, less sterile, more fun. I’m going to go change my automated sign-up emails right now! Thanks for the inspiration!

  22. Great post to read first thing on my 27th birthday. I’m a musician and hope to be able to educate the world musically with my success as well. Thanks Tim, you get it.

  23. Makes us wonder why other companies don’t adopt that playful, cheerful approach to their customer service

  24. I have a business thats doing very well however, when I read about how this guy built such a huge revenue machine taking himself out of the equation almost completely it reminds me how much I’m still doing wrong. I need to be a free man by 2013.

  25. Hey Tim,

    Another great example of how small tweaks can make a big difference. Love it! I find these examples really useful and try to make notes of them to replicate in my own businesses. Other good ones I like are Grove’s “Happiness Policy” and some of the quirky, fun and to-the-point emails sent out by clothing line ASOS – they even managed to make their return policy a bit fun.. quite an accomplishment in itself.

    Great example and I’ll be checking out Derek’s blog.



  26. I love synchronicity.

    I (and a number of others) were a part of the review process for Derek’s book. When the book was released Derek sent us all digital copies as part of the thank you. I’d always meant to purchase a hard copy and finally got around ordering one a few weeks ago.

    Yesterday I decided to craft my own version of “The Most Successful Email” for a client and set it up with their automated invoicing system. When I returned home the same afternoon, I found a nice surprise in the form of “Anything You Want” waiting at my doorstep. Today, a new guest post by Derek on Tim’s blog about the same email!

    For those of you who haven’t read the book I highly recommend it (and a visit to Derek’s blog); lots of great content much like Tim’s. I’ve also had the pleasure of meeting him and experiencing his hospitality. Never have I known a more genuine, inspiring, down to earth, and passionate person; a true old school gentleman.

    Sorry Tim, I’m sure you are as well but I can’t comment on that! Oh and it seems your blog’s copyright is out of date by a couple of years…

  27. Great read Tim/Derek. Thanks for sharing this with the community. There is definitely great joy and benefit in a.) taking the time to think about the right details and b.) having some fun with it while you’re at it.

    We get knocked-around a bit for doing it. But every time we do a gift giveaway or something fun for our community, we actually write quirky hand-written thank you notes personally thanking folks for sticking with us and being apart of the “tribe.” Some folks even take photos of the package upon receipt and share them on our FB wall. That’s really cool for us. It feels good to know that folks appreciate our quirks and humor. It really is the simple/small things that can have the biggest impact, sometimes.

    Thanks again,

    Mack Sabbath

  28. Great seeing so much personality coming through in such a common bland interaction.

    If I remember correctly, CD Baby also generated a unique reply email using the customer’s name. The little touches really add up!

  29. Very goofy but definitely a much better approach then the boring standard email most companies use in similar scenarios.

  30. Tim, this is great – Derek is actually how I first discovered your book. I met him at a songwriters conference way back in 2003. Total inspirational guy. His latest book was freely distributed at a dev conference I spoke at recently. Can’t remember the title, but it has a kids face poking out of the sand – lol

  31. Interesting way to create a happy customer, but doesn´t Derek take them for a fool/ plays them a big story which in reality is of course totally different? I´ve worked as a consultant for an online shopping website, and their fulfillment contractor was not working like Derek describes in his mail to the customer – and actually no one in fulfillment does; not even in luxury goods 😉

  32. I know I have a habit of thinking I have to do some grandiose thing to make a difference in my business and in my personal training business. It is often the little things that matter. I remember what really got my clients talking about me was a small change in sending them a handwritten thank you card. In the age of digital somehow that stuck out. It helped me to grow my business from $5,000 to $300,000 a year because people really felt like I cared. And it is because I do. Great story and tip and useful.

  33. In a Germany an email like this is prohibited by law. The text is very nice but simply not true. And in over regulated Germany this is unfair competition (“Unlauterer Wettbewerb”).

  34. I definitely think that by thinking outside the box and doing things differently like CD Baby did can really be a very good business move for most businesses. Customers will feel more like your friends than your customers which is exactly what you want. Nice job, and great post!


  35. Very cool, very inspiring — you’ve given me ideas on how to improve my customer contact points at my company. Time to hone the emails!



  36. Thank you Tim for you interesting post. I am professional classical musician, and was wondering about the bad situation of classical orchestras today all over the world (also in the us). What solution can you offer to them?

    What can they learn from this experience?


  37. What a great little e-mail. I’m just getting started with creating my on-line business but will be sure to follow this blueprint. Anything to add a bit of positivity and humor to the day is a good thing! Nice touch.

  38. When I first read “CD Baby” the first thing I remembered was getting that first email. I can’t even remember the name of the artist or CD, just the email. I remember that I even forwarded it to my friends.

    So glad to hear that he continues to do so well.

  39. I actually like Derek Sivers. Not because of his work, but he is one of the few very authors who actually answer emails. And that is why I can say for sure, that this post is completely worthless. If you are fascinated by stories, you just got jibbed.

    In the email I received from from Derek Sivers, he confirms that his financial success was a complete “accident”. He agreed that his book is just a few of his blog posts stitched together because someone asked him to, a “quickie” as he described it. In fact, he said he didn’t even know who can relate to his book and that it does not have much meat and bones to it. Derek Sivers attest to the fact that what he did was “total luck” and cannot be replicated.

    The same can be said about this “successful email”. Nothing described here can help your emails to be more “successful”. It’s pure luck because Derek Sivers says it was pure luck.

    *A copy of the email from Derek Sivers can be provided by requests from legitimate parties.

  40. Loved this! We all want to feel special, we all want to laugh and we all sit up and take notice when something is different – Derek achieved all of these with his email, Customer service at its best!

  41. I see a lot of your readers haven’t been doing their homework, Tim. Derek published this story in his short book “Anything You Want.” It was good to hear it again, though. I keep it in mind whenever writing copy for my site.

  42. Another great example of creating a unique customer experience that people feel compelled to share with others.

  43. Tim, I loved this last blog post because it went’ back to an essential lesson that you first touched upon from the 4 Hour Workweek. One that inspired me to shorten my work week and explore my internal musings:

    That we ought to value the time we have to spend doing the things we love over the zero’s in our bank accounts.

    Derek Sivers (and I believe you as well) seem to really get it. Thanks again for reminding me of the true quest we are on in both life and business!



  44. Great email and very inspiring story! I love the personal touch in the email, that is terrific. Congrats on all of your success!

  45. Haha! Love it.

    I also noticed that whenever I’d send playful, colorful emails, people loved them and responded warmly, so I started doing that as a regular, normal thing.

    It’s simply being human, playful and engaging.

    Makes us think why we EVER are NOT in our “work” stuff.

    Thanks Tim. Love your stuff.

  46. Ramit Sethi did an interview with Derek that I found really inspiring. The big takeaways that I recall was about how to challenge assumptions about how things like getting an education or running a business “should” be done and how you can be a person who looks for opportunities to create value instead of seeing only obstacles. I’ve listened to it a few times and I definitely recommend it.

  47. As far as the short sleeves shirts: why not?

    Never heard this before. I’d be more against the European jeans+jacket look. Can’t stand it.

    The email has its unusual touch, always inspiring to hear such stories based on an original yet simple idea…

    Tim, are you going to cover an omnipresent monthly subscription model? I’m intrigued by all these subscription companies mushrooming everywhere.

    And of course shameless plug 😉 –

  48. Tim,

    Really enjoyed the interview with you and Derek. You always get me thinking in new directions. Thank you.

  49. I completely agree, it’s these little things that make the world more personal, we live in a world of proforma statements and standardisation although we are all more connected the mass-communication aspect has dumbed down the richness of the message.

    As another example, I bought some t-shirts from a uk website called truffleshuffle and they had sent me small packets of sweets as well in the order bag, I was almost more surprised and excited about that than i was about the t-shirts i’d ordered!

    Derek has chanced upon an enduring meme for his service which is great as people look for and appreciate it I suppose the trick is really making the impersonal seem personal but how to sustain it?

    It’s a bit like the ‘barnum statements’ employed by psychics in cold reading, creating the illusion of something direct. But ultimately how long does that last before people see through or get bored by it, if you get the same message or treat each time it will lose it’s impact and even cycling through a set of messages/treats may only last a few order cycles, depending on the frequency of your customers.

    Actually being personal would be the best solution but that comes at a cost. Maybe you could employ a scheme where you encourage a customer to provide a message to the next customer and so on and so forth which would only require more infrequent input centrally to kick things off or give the hula hoop another tap. That could help build community around your product or service and be self sustaining.

  50. Nice post Tim, Thanks for introducing me to Derek and his work. I have just spent 30 minutes reading his blog and his story. Wise man indeed. Great musician too!


  51. Respected Sir,

    Read your book on 4hour work week….loved your idea of winning that martial art competition…that knockout loophole…Great things are not done by impulse, but by a series of small things brought together.

    George Eliot

    Thanks for writing such a great book and maintaining such a great blog….



  52. I love how Derek overcame his fear by doing hundreds and hundreds of ringleading gigs. It’s amazing the power of just taking something you’re afraid of and doing it so many times it becomes old hat.

    I think it has to do with reaching a stage where you’ve seen all the things that, before all that experience, were unknowns to fear. You have probably encountered every category of challenge you’re likely to face so you know you’re prepared.

  53. Just finished the 4 hour work week and just wanted to say you inspire me to be better than I am. Thank you for all the info you put in the book and keep writing. Justin

  54. Totally inspired! This post, the post about starting a business with no money and your interview with Noah Kagan last year about testing clearly defines the road to success. I’ll be testing my design product this weekend using Adwords and Google insights. No more fine tuning on my product unless I can prove the market. Thanks, Tim!

  55. I love the imagery that this email conjures up. There’s something about lighting a candle and sending a CD via private jet. I think the business lesson here is also much needed – we can all stand to have a little more fun in our businesses, and so can our customers!

  56. Awesome post, as usual, but for the record…

    ring leaders are in the Mafia, ringmasters are in the circus.

  57. Derek Sivers is a natural-born businessman! Thinking out of the box and write a silly email that turned out to be a hit.

    Few people possess such talent and they all founded the most successful businesses there is today.

    For Sivers, who worked 4-hours/6 months selling CDs online, KUDOS to you! Such talent should be shared and serve as an inspiration to others!

  58. Wondering when you will have a post on finding a marketable product beneficial for the current market.

    I always hear how you should find something you are passionate about and work with that to discover a product. But, what if your passions are too high tech for beginner design?

  59. I appreciate those companies who really make an effort to ensure that their customers would have fun with them and not only think of the dollars they would make after every transaction. Although the the things Derek Sivers wrote on the email is imaginative in reality, its nice to know that they want their customer to enjoy doing business with them. Normally customers would not read the entire email a company would send them but just look for relevant information. Such email is very interesting and fun, any customer would enjoy the entirety of it.

  60. Tim, I have a problem with eating within 30min after waking up. I feel nauseous. Can only get something in my body after about 3 hours. I think its a blood sugar problem, but don’t know. Is there something I can do about this. I can’t find anything in your book.

  61. Hi Tim

    Just wondering, if, for instance, I have my cheat-days on saturdays, which day during the week should be my weigh-in day?

  62. “It’s the little details that are vital. Little things make big things happen.” ~John Wooden

    This is something that Sivers and yourself have done (and continue) to do very well! Great post!

  63. Love this. It has inspired me to write better automated emails for my business… it just goes to show that a little personal touch can really go a long way.

  64. This was inspirational, just to think that from one email (and some other thing) you were able to create this huge company! I will be doing something along these lines after we complete a roof cleaning, just a short email saying, we hope your happy with your clean home! See you next time! Great little article here!

  65. thats awesome! I just read the blue area where he said that he changed up the confirmation sale email that lets you know it will be shipped to your home. Brilliant idea, I will be trying to incorporate that into my business!

  66. Cool article. I am a musician (mainly guitar but some ukulele also), and I’ve heard of CD Baby. I now have a new profound respect for a company that treats their customers with such class.

  67. I’ve been struggling to get a new biz off the ground for a year or so, and now since reading this post I think I’ve got a fresh idea about how to approach customer service. Thanks Derek and congrats.

  68. Great story. I visited his website and looks like he lives in a few different places over the years. Currently NZ. Nice! Also did the math and 1.1 mill aren’t too bad for a yearly payment from a 22 mill pay day. Inspires me to write a cute little email like that.

  69. Just came across this post from another blog. Loved it! I must use a variation of that email. Thanks and again….great post

  70. LOVE! What a simplistic way to reach into the soul with one master email. Made me laugh out loud with appreciation. Just…Genius!