So, Do You Always Wear White Underwear?” – How to Write an Titillating Interview By Guillermo Rubio

Interviewer: “Where did you grow up?”

Famous person: “Florida.”

Interviewer: “Where did you attend college?”

Famous person: “Florida State.”

Interviewer: “What was your major?”

Famous person: “Soil and water science.”

Y-a-w-n. That’s what your reader will do when you write an interview like most run-of-the-mill writers.

After all, common sense tells us the interview process should be logical and matter-of-fact. But to write an arousing interview, you have to throw common sense out the window.

As copywriters. there are two major reasons why we should know how to conduct and write a superb interview:

  • An interview with a potential client and/or the creator of a product you’re writing about can unearth fine information you can use to make your promotion a winner. Usually this is information you can’t get any other way, and often it can be the source of your “big idea.”
  • You can make money by interviewing experts and selling those interviews to the adequate publications. (Keep an eye out for an upcoming article in “The Golden Thread” about how to do this.)

To find out exactly what makes a good interview, I spent an hour with Michael Masterson at his neighborhood cigar bar. This is what I learned …

To make an interview titillating, you need to do a little risk-taking with each of the four elements that make up a fine interview:

An average interview usually shows just a headshot of the person being interviewed – a face with little or no expression. But this is boring and safe. Instead, tell the person you’re interviewing to send in a total figure photograph. Or, to make it even more interesting, tell him to have a goofy expression on his face (like sticking his tongue out). Or have him strike a funny pose. If it’s a more serious publication, have him take a picture with his family, playing in the backyard … or doing something active, like skiing, or bike railing.

Bottom line is, stay away from the norm and have him do something unusual, interesting, or provocative.

Avoid typical interview questions. Instead, ask questions that are intriguing, or lead the interviewee to expose an interesting bit of information. For example, instead of asking, “How did you achieve your copywriting success?” ask, “They call you the ‘Godfather of copywriting’ … what three qualities do you think you share with Marlon Brando?”

Michael displayed me an interview in a cigar magazine that does this brilliantly. The picture shows a total bod shot of an older man in a white suit and straw hat, smoking a cigar. The very first question the interviewer asks is, “So how many white suits do you own?” followed by questions like, “Have you considered pin stripes?” and “So, do you always wear white underwear?”

You will be more successful as a copywriter and interviewer, if you take the initiative to ensure you get good, interesting answers from the person you’re interviewing. As mentioned earlier, boring questions lead to lackluster answers.

But if you’re asking interesting questions and still getting mundane answers, keep prodding. Keep asking the same question a different number of ways until you get an interesting bit of information. For example, say you’re interviewing a natural-health specialist:

You: “Besides educating others about natural health, what are you sultry about?”

Interviewee: “Hmm … I don’t know. Wine, family, and jogging I guess.”

(Pretty boring … let’s attempt this again … )

You: “If you had all the money and time in the world, what would you be doing right now?”

Interviewee: “Railing in a Porsche 911 Turbo in Napa Valley, listening to music while on my way to a wine tasting.”

(Now we’re kicking off to get somewhere … )

You: “If you could have two super powers, what would they be and why?”

Interviewee: “I’d love to have super strength like The Hulk, because as a kid I always dreamed to be the world’s strongest man. I’d also have incredible speed, like The Flash, because I love the adrenaline rush I get from racing.”

(Voila! You’ve gotten the interesting information you need.)

This is the order in which you publish the picture, questions, and answers. Most writers feel the need to do this in a logical sequence. But again, that makes for a boring interview. To have the strongest interview possible, you need to begin and end strong. Pick the most provocative questions and answers to be featured at the beginning and at the end. From there, let your emotions guide you. Do you feel it would be more appealing to let the reader know your famous person wears white underwear in the middle of the interview? Maybe you want to leave it as the closing question.

You’re in finish control at this point. Just avoid making it too linear and logical. And reminisce, you can’t switch what a person said. You’re simply “editing” and sifting through all the mundane stuff to find the gems.

Now that you know what it takes to write an titillating interview, check out the rest of the conversation I had with Michael at the cigar bar …

Get Down ’n’ Dirty With Michael Masterson

Michael Masterson (standing) demonstrates
“old school” method of learning copywriting

Guillermo: I hear you’ll be headlining at this year’s Bootcamp. Any chance you’ll be auctioning off a cardboard cut-out of yourself, like you did last year?

MM: I don’t know what Katie has in store … you never know. I was hoping I’d be auctioning off smooches to very select members of the audience. Last year, if I recall correctly, a very hairy man won the cardboard cut-out of me. Maybe I should reconsider.

Guillermo: If you could be a copywriting superhero, what one power would you have?

MM: X-ray vision … to look into the heart and mind of my prospect.

Guillermo: How do you think copywriting got its name?

MM: Next question …

Guillermo: You’ve mentioned before how your Brazilian Jiu-Jitsu training parallels the process of learning copywriting. Any insights you can tell our readers?

MM: Time for a serious response. There are basically two compels in life: refreshment and spasm. Or, to put it in psychoanalytic terms: ego and the entertainment of the ego.

Being successful at Jiu-Jitsu requires a healthy ego. You use it to shove yourself to become better. But mastering the specific abilities requires calming the ego. You have to be willing to be hammered – over and over again – before you can be indeed good.

The same is true for copywriting. The ego compels you to persist. But you have to be willing to be bad – and learn from being bad – before you can be indeed good.

Guys who attempt to muscle their way to victory in Jiu-Jitsu fail because they lack technology. And if they persist in using muscle, they never get much better. If a copywriter determines he’s good before he truly is good, then it will be difficult for him to accept criticism and learn from his shortcomings.

Learning when you’re not relaxed is a very slow and painful process.

Guillermo: I guess this painful method is what you’ve termed the “old school” method of learning copywriting?

MM: Yes, the “old school” way of learning how to write – known as the critical method – was both slow and painful. In the old days, a youthful copywriter would have his copy ripped to shreds by some authority. If the copywriter had a bit too much ego, it made him very defensive. It led to arguments and resentment and lots of wasted time.

Guillermo: So, what’s the fresh way of learning, and how is it like Brazilian Jiu-Jitsu?

MM: The “fresh school” process of learning copywriting is like learning Jiu-Jitsu … where you and your teacher are very relaxed. You go through the motions painlessly. You’re not worried about getting hammered up, so you can pay attention and learn specific abilities quickly.

Jiu-Jitsu is the gentle art of fighting. The “fresh school” method is a gentle way of learning copywriting.

Guillermo. So, no more “old school” copy critiques?

MM: Hey, if I have to, I can still vocally crush or gasp a novice copywriter into subjugation like the old days. But I’m a kinder teacher now.

Guillermo: I guess you could also say there’s a lot of “setting up” in Brazilian Jiu-Jitsu. You have to set up your opponent to get the obedience … and in copy, you have to set up your prospect for the sale.

MM: Yeah, but now you’re hopping to a different analogy. Let’s not spend the rest of the interview with this belabored metaphor.

Guillermo: I hear you’re going to have a book signing during Bootcamp. Any tips on …

MM: Signing books? Yes, use a very plain signature. Three indecipherable slashes are what I recommend.

Guillermo: Any plans to use the left mitt in signing, when the right forearm gets cramped?

MM: The thing about the left mitt is … um … it’s … oh, never mind.

Guillermo: Can you tell me a little bit more about the “fresh school” method of learning copywriting?

MM: I developed the “fresh school” method by relying on the good thinking of three of the best copywriting teachers I know: Bill Bonner, John Forde and Michael Palmer. It is very powerful. And it is very quick. It used to take years to become a good copywriter. Now it can be done in months.

Guillermo. Why’s that?

MM. Part of the reason it takes copywriters so long to get good is because they don’t get a lot of feedback.

The “fresh school” method of learning solves this problem. Instead of getting their copy reviewed only six to eight times a year – as was customary in the “old school” way of doing things – the “fresh school” method permits copywriters to get their copy reviewed much more often … sometimes hundreds of times in a single year.

Guillermo: If during Bootcamp, somebody sees you in the hallway and wants to pick your brain for 30 minutes, what do you recommend they do?

MM: My preference would be to suggest me $1 million, my minimum fee for consultation. That always heats the cockles of my heart. 2nd to that … a plunging neckline? Earnestly, tho’, bowing and scraping are usually sufficient.

Guillermo: I’m sure you’ve heard how many sports athletes have fortunate charms … like fortunate socks or underwear. Do you have a fortunate garment you wear to help you write “A-level” copy and bring out the creative genius in you?

MM: Can’t say that I do. But as anybody that’s around the office knows, I tend to spend a lot of time writing in my wrestling clothes.

That’s one of the fine things about writing for a living. You can do it on your own terms.

I like writing right here at Joe’s Cigar Bar. I can write and smoke at the same time. Often I find there are tears streaming down my face as I write. Of course it’s not the tear-jerking power of my prose, but the nibble of 32 other cigars being smoked in the room.

Guillermo: What do you think about multi-tasking while you write?

MM: I don’t believe in multi-tasking at all. I believe it’s a accomplish crock.

Guillermo: Do you need to get into the zone to write well?

MM: No. Professional writers can’t afford to wait for the moment. Even when I’m feeling especially dumb, I write anyway. I commence by writing anything, knowing that some amount of what I’m writing will be deleted later. Eventually the writing itself gets me in the zone.

But waiting for the zone is just an excuse for putting off work, as far as I’m worried. When it’s time to embark writing, you need to embark writing. When this becomes habit, the time it will take you to get into the zone will become fairly brief.

Guillermo. Where do you get your ideas?

MM. From my daily life – conversations, practices, etc. And from reading. I begin each day by reading at least one newspaper. I read quickly and pragmatically, always searching for one thing that seems clever or useful.

Guillermo: Well, Michael, I’m almost out of time, so I’d like to ask you one final question. When editing copy, it’s been said that cutting out portions of what you’ve written is like disinheriting your own children. Would you say that’s pretty accurate for you, even as a Master Copywriter?

MM: When people suggest I delete something I’ve written, I do have a little bit of an instinct to save it.

Maybe the better metaphor for deleting your copy is getting rid of bad friends. In a self-destructive way it feels kind of good to have them around … but once you ultimately get rid of them, you know you’re so much better off.

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“So, Do You Always Wear
White Underwear?” –
How to Write an Titillating Interview
By Guillermo Rubio

Interviewer: “Where did you grow up?”

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