Issue #26: My Changed Belief on Interviewing

One closing question I ask podcast guests is, “What’s a belief you used to hold strongly and have since changed your mind on?” I like this question because it shares some insight into how their views have changed with time and experience. Well, when it comes to the podcast, there’s a belief of my own that has shifted since starting the project. From my 2019 annual letter on being an interviewer:

“I’ve also tried to talk less during episodes and keep questions as short as possible. Sometimes if the answer makes sense on its own I’ll delete the audio asking the question so we can hear more of the guest and less of myself. I want listeners to feel like the guest is talking to them, with me being their voice and a conversation guide.”

The core belief in this statement is that I as the interviewer am unnecessary and serve only to encourage the guest to continue sharing. I believed by removing myself as much as possible, even deleting the audio of my question, the listener could feel like the guest was talking directly to them and feel more engaged as a result.

During the editing process with Greg Geronemus on our episode, he pushed back on this idea and urged me to keep myself more in the conversation. As he heard the first draft of our podcast with some of my parts removed, he noted how it didn’t flow as smoothly as the real conversation had. Without my full questions, the podcast was harder to follow and didn’t feel as natural. And he was completely right.

As I replaced the audio I had deleted, I realized another key point. You don’t put the listener in the conversation by removing yourself as the interviewer. The listener gets in the conversation through the interviewer. As a listener, I can’t ask questions so if there’s nobody asking questions within the podcast I feel less engaged and can’t relate to the discussion. Therefore, I need someone to represent me to truly feel a part of the episode. My original belief was the interviewer was an unnecessary part of a podcast episode. Today I believe the opposite and see the interviewer’s role as crucial to a great podcast episode that is engaging to listen to.

If there’s anything else you can think of I can be doing better regarding the project, please don’t hesitate to reply to this email or reach out. I’m always excited to chat.

Capital Notes

  • Permanent Equity wrote about the use of debt in a business in their weekly newsletter.

  • Chenmark’s newsletter this week about finding great leaders for small companies was fantastic.

  • Patrick O’Shaughnessy’s episode with Ben Thompson was super interesting from a tech and media perspective, my favorite section being a discussion on local news and how journalists can build local news models through platforms like Substack.

  • This was a great article about Judy Faulkner, founder of Epic Systems which makes electronic medical record software, and her decision to donate the vast majority of her wealth. It’s not a recently published article, but I did a little digging on Epic and this was one interesting link I came across.

  • Scott Miller wrote his quarterly letter for his fund of funds called Partners Fund and outlined new investment ideas from a few fund managers they invest with.

If you found an interesting article, podcast, or interview that I missed, please let me know, I’m always looking for interesting stuff.


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I’m always looking to connect with folks interested in this space, don’t hesitate to reach out.