The Most Genuine Person on the Internet

Being genuine on the internet is hard.

Part of the difficulty is that it’s easy to fall into the status game trap. Additionally, publishing anxiety is real and we are our own harshest critic. When we do see authenticity on the internet, it stands out like a flower growing through concrete.

Derek Sivers is one of those people. He’s one of the most genuine, accessible, and generous people on the internet. I’ve been following him for a few years now and he’s done nothing but impress me. Here are a few examples:

He cold emails people with small audiences (this was pre-gumroad Sahil) expressing his gratitude without expecting anything in return.

Here it is! Sent 11/11/2010: Sahil, LOVED your posts about wearing a mask, and now nil-nil. Really well done. Insightful, non-obvious, and succinct. Just wanted to say thanks for your writing.”

— Derek Sivers (@sivers) December 11, 2020

He announced his book, sold all copies, then a few weeks later announced that he’s giving all the money away.

I’ll admit, it made me ridiculously happy to make $250,000. I was expecting way less than that, so it was a big surprise. I had a spring in my step for days.

Then I thought about what to do with the money. There’s nothing I want to buy. Should I put it in an investment account? Eh. For what purpose? I don’t want more money.

So, I decided to donate it to charity.

He sends emails like this.

Subject: James - are you real?

Hi James -

You signed up for my private email list at

… but since you’ve never replied, I can’t tell if you’re a real person.

Please reply to this email and say anything, ideally something about yourself like where you are in the world. Or feel free to ask any question.

(I read and reply to all. This part isn’t automated. It’s just me.)

If you don’t reply, I’ll assume you’re not getting this, and delete this email from my system.


Derek is truly one of a kind.

For me, he’s a north star on how I want to be as an internet citizen.

May 6, 2021

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