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Ben Thompson on how to make it in the media in 2016

"The most important article you write on your blog is the second article someone reads ... If that next article is also really good, then you've established something meaningful with that reader. You have the inkling of a relationship." — Ben Thompson

Since launching Stratechery in 2013 from his home in Taiwan, Ben Thompson has established himself as one of the smartest and most thoughtful analysts at the intersection of media, business, and technology.

Just as impressive: Thompson has also figured out a way to turn Stratechery into a viable business; his one-man operation operation were earning more than $200,000 in annual revenue by January 2015. Thompson is coy about the number now, but it's safe to assume it's considerably higher.

So getting to geek out with Thompson on the state of the media business is a lot of fun. In the latest edition of my podcast, (which you can listen to by subscribing to my podcast or streaming it on SoundCloud), we talked about a number of topics close to my heart, including:

  • Whether you can still make it as an individual blogger — Ben is showing you can, but the path has really changed;
  • Why Ben's background as a Christian conservative who was the only person around who loved technology has helped him as a tech analyst;
  • Ben's time working for Apple and Microsoft and what he learned about both companies and their cultures;
  • Why the Innovator’s Dilemma is worth reading even if you think you already know what it says;
  • How to make money as a modern media company, and why it's easiest for very small sites or very big ones;
  • How to manage the the "time-mismatch" between writers and their readers on the web;
  • Why good bloggers often repeat themselves so much, and the importance of exposing your mental models to your audience;
  • Why so few companies advertise on podcasts;

And much, much more.

This is a particularly great episode if you're in new media, or thinking of getting into it, or just want to understand the business dynamics behind the content you consume. There's a lot of advice here that I wish I had known when I started as a journalist.

A big thanks again to Thompson for taking so much time for this conversation. And for more podcast conversations — including episodes with Rachel Maddow, Bill Gates, political scientist Theda Skocpol, and conservative activist Michael Needham — subscribe to The Ezra Klein Show. For write-ups of past episodes, head here.