Billy Decastro Speaks

Billy Decastro Speaks

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Billy Decastro Speaks
Billy Decastro Speaks
Why Ask? (Museletter)

Why Ask? (Museletter)

Recount #4

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Billy Decastro Speaks
Jul 25, 2025
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Billy Decastro Speaks
Billy Decastro Speaks
Why Ask? (Museletter)
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I have been called many things during these 23 years – some flattering, some not – The one I mention here is the Master Questioner, which I don’t officially use, as it smacks of (as we said in my era) “Biting.”

Listen to the Musecast Version

An alternative perspective to that viewpoint is that of the reggae culture I grew up in, where one takes on part of the moniker of their father or brother, whether that be physical, or in the sense of being ‘raised by’.

The above numen is a spin-off of my mentor's appellation…

Ian Dunlap The Master Investor.

Listening to him (both interviewing, being interviewed, and synchronously reverse-interviewing his interviewer), as well as some other greats, I began to wonder – and will now, I think, begin to investigate – the motivation of the very best interviewers.

Not the ones they might have developed over time, but the initializing, galvanizing reasons that undergirded their natural inquisitiveness from the very outset.

Journalism (i.e., being a 'reporter') seemed... seems, too constrained.

Although that particular characteristic is evolving, due in part to platforms such as Substack, journalism always came across to me as overly… rigid.

There are 'rules' to all writing, sure, but journalism class, in my amateur opinion, appears to add some over-the-tops. Might just be me. Probably is.

I just like to write whatever I feel to write. It's my personal, inner view – my Insider view of the world, having stood apart from it, yet literally within its very bowels – fostering a very different perspective… I digress. Contrary to the trending ‘truth’ I don't craft designer questions in a quantum laboratory. I simply ask what I want to know.

I ask – and I think this is vital – the questions I want to answer, myself. Meaning, I put Q's on the table, the answers to which I am both seeking for, and would like to be asked if I were interviewed myself. Views I would like to put across, which therefore incites my curiosity of the would-be response of those I admire, respect.

The curiosity of this, makes me further curious, as to if the most renowned interviewers experience this same phenomenon.

So, Boom – Time to Lock In

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The best questions, I've come to finally overstand, are those that everyone else also really wanted to know the answer to but didn't realize they wanted to know, because they never thought to ask. One can almost effortlessly swineback off of someone else's amazing question.

A Shout out to Bloomie Nichole! 🙏🙏🙏

That initial banger, though? The one that makes the interviewee excited at the challenge? The one that makes them feel they can't wait to respond? That's what I consider a great question. As in all things, though, consistency. That's the takeaway. Because plenty of people can drop one off sometimes. Like everybody's got a good joke here and there. Hell, even I'm funny once or twice a week!

The question is can you come with the heat week after week, night after night? Now, there's a great question! Me? I've rolled out a cooker or three in my time. But consistently? You'll have to foreman the jury on that one. What I can say in my defense, is that I'm always on the stove, working to chef up some cuisine for gourmet thought. Here's hoping you enjoy this eclectic dining experience.

That being said, I leave you with a question:

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