Afterthoughts: Anything You Want by Derek Sivers

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Afterthoughts: Not Overthinking Podcast

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Derek Sivers outlines the purpose of the book on the first page: it is 10 years of experience in one hour. He offers 40 lessons for a new kind of entrepreneur which were all picked up in his 10 year journey growing CD Baby. CD Baby was a music distribution platform for independent artists. Sivers started it in 1998 and sold in 2008.

The best part of this book is that it was all highly actionable. In many ways it reminds me of how James Clear writes Atomic Habits. The explanation of each lesson was concise, but informative enough to illustrate the point. 

Much of what he talks about is tactical business advice that you will find in most business-related content. But some of what Sivers is contrarian in nature. For example, he suggests your goal should be trying to keep your business as small as possible. The bigger you get, the more fluff you absorb, and you ideally you want to stay small, focussed, and lean. I understand where he is coming from, but frankly, I had never considered this perspective. Another controversial thing he suggests is to not care about common overhead process like financial analysis e.g. projections, annual statements, etc. At least not until they become necessary. The focus in not on adding superfluous systems or processes, until it becomes unsustainably painful.

Sivers approach optimises not for profit, but for the wellbeing and satisfaction of his customers’ core needs. This goes against traditional business thinking. He believes businesses should be willing to fold or be sold if they are no longer the best at serving their customers.

The customer alone is the priority. In terms of within the business, he believes in bootstrapping and picking yourself up by your heels. This is best illustrated by his persistence on coding up CD Baby himself, learning from scratch to do so. At the core of his message, he tells us it should be fun. He started CD Baby for himself, so he could sell his music. The fact that it kept growing was never his intention or his desire. He only continued to do so because of how much of an impact he was making on other musicians. 

While Sivers’ message is bold and refreshing, I can appreciate that it can be seen as idealistic. Survivor’s bias is definitely a concern for his CD Baby story. Having said that, I love the spirit in which the book is written and this new-age business philosophy he is promoting.


Highly Recommended. A snappy read that packs a punch. Derek Siver’s philosophy on business is contrarian, forward-thinking, yet practical. It’s left a lot to think about, and no doubt one I’ll reread before too long. The book can be found free here.

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