The Outline (Part 1)

The Outline

Context

Before Microstartup Stories I tried my hand at the Startups In Depth podcast. The idea was basically to apply Socratic Grilling to interviewing startup founders. Let me try to explain.

Consider this excerpt from the Socratic Grilling blog post:

Teacher: Many diseases like the common cold are spread by germs, when one infected person contacts another.

Student: But I got a cold a few weeks ago, and I never touch anyone except my family members. And none of them were sick.

Teacher: You don’t need to actually touch someone. Sometimes it can spread through mucus droplets in the air.

Student: And one time I was camping in the woods for a month, and then I got a cold, even though I hadn’t been around anybody.

Teacher: If it was spring, you might have gotten allergies. Allergies can feel a lot like a cold, but they aren’t spread by germs.

Student: It was fall.

And:

...to a hostile observer, it would sound like the student was challenging the teacher. Every time the teacher tried to explain germ theory, the student “pounced” on a supposed inconsistency. When the teacher tried to explain the inconsistency, the student challenged her explanations. At times he almost seems to be mocking the teacher.

The conversation basically took the form:

Teacher: X works like this.

Student: That doesn't make sense to me. What about A?

Teacher: No.

Student: That still doesn't make sense to me. What about B?

Teacher: No.

Student: That still doesn't make sense to me. What about C?

For whatever reason, in our culture, someone who does what Student did is usually seen as being contentious and argumentative. I don't think that should be the case though.

And more to the point, I think that it gets in the way of interviews of startup founders. When I am listening to podcasts like Indie Hackers that interview startup founders, I'm often feeling like Student. "Wait, that doesn't make sense. What about A?" or "Wait, I understand A1 but that doesn't really give me a good picture. I still want to hear about A2, A3, A4 etc. before you move on to B."

I don't think I'm alone here. I think listeners have the same questions and thoughts. It reminds me of when they tell you in school not to be shy about raising your hand and asking a question, because if you have the question chances are at least a few other kids in your class also have that question.

Here's an example. I was listening to an episode of the Indie Hackers podcast earlier today featuring the privacy-based Google Analytics competitor Plausible. I am somewhat familiar with Plausible myself. That's partly why I wanted to listen to the episode.

They briefly described what Plausible did in the episode (although I think they could have been more clear and went into more depth). But they didn't really address the question of why it is a better product than its competitors. After all, they did mention that it is a crowded market. I feel like that is an important thing to understand, and is something that deserves a bit of socratic grilling.

It's possible that the answer to that question is that they're not better, or that they're marginally better, and they just win through marketing or something. If that's the answer, that's ok! But it's still important to know that. Maybe there are some lessons to be learned about the importance of being a clearly better product than your competitors. At the very least it would be a data point. One of the reasons I like to listen to these interviews is to collect these sorts of data points.

There's a lot of other sorts of things I would want to go into more detail on. Here's another example. Consider the Indie Hackers podcast episode with Baird Hall of Wavve. At 3:27 Courtland starts asking Baird about why he quit his job to start his first startup. Baird spends a little bit of time explaining that it was a mix of a gut feeling and seeking some sort of creative outlet (check out the transcript).

Courtland follows up by asking a related question of why he started a tech company as a non-technical person. Baird spends about 70 seconds answering the question, saying that 1) he worked as a salesperson at a tech company so his head was in the tech space, 2) building an app was how to scratch the itch he himself was having, and 3) he had a technical cofounder.

And then that was it. From there they moved on to a new topic.

Two minutes and 32 seconds is not enough time to explore Baird's experience in deciding to start a company! I've started two companies myself and I know that there is a lot more to say. You could easily spend a full hour discussing it. When I was listening to the episode, I found myself wishing I could interject and ask a bunch of follow-up questions.

The obvious issue with this sort of approach is that most podcasts want to be like 60-90 minutes, and if you did a deep dive into each and every question like this it'd turn into a Joe Rogan episode. But maybe that's ok. I suspect that it is, and it's a hypothesis I want to test.