Adam Zerner

The thinking behind the Startups In Depth podcast

Web page for the Startups In Depth Podcast:

There are currently a lot of podcasts that interview startup founders. Think about how they typically work. Episodes are about 60 minutes long. And maybe the founder has been working on their company for three years. The interviewer usually starts from the beginning and continues down the timeline until they hit the present day.

This implies covering a time period of three years in 60 minutes!

I think that's way too shallow (much of the time). What I want to do with Startups In Depth is, well, focus on depth instead of breadth. I won't settle for a wish-washy surface-level understanding of things. I want to go all the way down the rabbit holes and continue asking questions until things really make sense.


Here's an example of what I mean. 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.


Of course, not every rabbit hole is worth going down. Think of it like an investment. Maybe it "costs" 45 minutes to get a full story of why Baird started Wavve. You have to ask the question of what the return on that investment will be. Eg. will the payoff be worth it.

Actually, it's more complicated than that. You have to ask a series of questions. What's the ROI of getting the 20 minute version of the story? The 10 minute version? 5 minute version?

There are definitely situations where the short version makes the most sense. And there are definitely people out there who just have a preference for executive summaries. I don't want to imply that my extreme-depth-over-breadth approach is always correct, nor that I'll always push my way down every possible rabbit hole. It's more that it's the theme of this podcast. It'll be a strong theme, but still just a theme, not a hard rule.

Socratic Grilling

There's a blog post titled Socratic Grilling that really does a good job of explaining what I'm trying to get at here. I'd really recommend reading it, but how I'd summarize it:

You've probably heard of the Socratic method before. Where the teacher keeps asking the student a bunch of questions.

Imagine that in reverse. Sort of. Imagine a student grilling the teacher with questions. Teacher says "A". Student says, "What about B?". Teacher says "C". Student says "What about D?". Etc. etc.

What image do you have of that student in your mind's eye? Probably someone kinda smart aleck-y right?

If you do, that's a really unhealthy attitude. To actually get a deep understanding of something, you usually have to keep drilling down: "What about X? What about Y? What about Z?"

Hopefully that makes sense. That's probably the best phrase for what I'm trying to do here: "socratic grilling".

Revisiting the caveat section above, now with the concept of Socratic Grilling... Socratic Grilling doesn't mean that you dig deep into every possible rabbit hole. It moreso means that you keep asking questions until you really understand what you're trying to understand. Some rabbit holes may not be worth going down even if you are seeking a deep understanding of something.

A road analogy

Imagine that you are taking a road trip from the east coast to the west coast. You could just hop on the interstate and go directly across the country. That'll get you there the fastest.

Or, you could take some detours. Maybe you come across a nice town in Wisconsin and want to explore the dairy farms. Maybe see some cool mountains and want to do some hiking. Maybe you find a cool view and just want to stop and ponder some things.

I think that's actually a pretty good analogy for a podcast interview. Taking 45 minutes to dig into why Baird decided to start Wavve would be the equivalent of stopping at a small town for a few days and exploring the dairy farms. It's not essential to you completing your road trip. It depends on your goals. Maybe you're just looking to get a high-level overview of the country. Maybe you only have so many vacation days and don't have time to take such pit-stops. Or maybe you do have the time, but you just don't find dairy farms interesting so you want to chug along until you find something that is worth stopping for.

Using this analogy, I don't think every pit stop is worth making, and I don't think it's worth spending months at every single pit stop. I'm just going to use my judgement for when it is and isn't worth it. But my judgement is going to err very heavily on the side of depth. If I were interviewing Baird I could totally see myself spending 90 minutes exploring that decision he made.

How long will these episodes be???

About 27 to 34 hours.

Just kidding. I'm aiming for 1-2 hour episodes, with 2-3 episodes per founder. Eg. for a given founder I'm hoping that there'd be a part 1, part 2 and part 3.

That still won't be long enough to explore everything in as much depth as I'd like though. But my solution to this will be cutting down on scope most of the time, not on depth.

How do you know this will work?

I don't. It's an experiment.

Well, that's not entirely true. I do know that it's something that I personally would love to listen to, so I know I won't have zero users. That's one of the benefits of solving your own problems. I expect that there are at least some people out there who have a perspective similar to my own. How many there are and whether I could figure out how to reach them are both big unknowns though.

But even if it doesn't "work" I'll still be happy a) getting to talk to founders and b) having the learning experience of trying to start a podcast.

If you have any thoughts, I'd love to discuss them over email: