Unintended Consequences with Paul Orlando – The Newsletterers – The Tim Show – S02E05

In episode 5 of The Newsletterers I spoke with Paul Orlando who every week publishes  Unintended Consequences about how second order effects play out in the systems we live in. Paul has spent the last 8 years in the startup and entrepreneurship world in innovation hotspots including his current role as a professor of entrepreneurship at University of Southern California (where he also runs the on-campus startup accelerator). As a lifelong writer this newsletter represents the first time he has dedicated himself to producing output over time.

Paul the shared origin story of his blog and newsletter, how he identifies topics to write about, and what drives him to do it at all.

In around an hour we covered:

  • the primary considerations in deciding whether to produce every issue (it must be fun, a learning opportunity, and provide value a reader)
  • why Paul didn’t associate his name to the project for a long time
  • the pragmatic reasons to adopt a weekly cadence
  • a cheat code to generate content ideas
  • the importance of feedback and validation and good luck
  • not trying to go viral (especially if it happens accidentally)
  • learning about your audience by reading your list
  • how producing a newsletter project is like jazz (improv within bounds)
  • getting over imposter syndrome to be comfortable sharing what you’re working on
  • deciding between hot takes versus lasting insights
  • how many readers you need to start a reader’s forum (i.e. Slack, Telegram, etc)
  • and more!

If you aren’t already, please consider subscribing to both this podcast and my newsletter. I also have the twitter, and would love to talk to you about this episode there.

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