Alexandra Wolfe on Overcoming Tricky Interviewees; an interview by Erin Hazelton

Alexandra Wolfe writes profiles for the Wall Street Journal. She also pens books and cover stories for Vanity Fair. A personal favorite of mine? She wrote about sitting in on Silicon Valley’s “Cougar Night” for Vanity Fair a few years ago. Wolfe reports about her night out at a hotel bar where a collection of women-of-a-certain-age congregate and attract younger men who, ultimately, indulge them. These intriguing mating rituals, and more on the specific traits of the awkwardly intelligent Silicon set, are further reported on in Wolfe’s recently published book, Valley of the Gods (Simon & Schuster). Wolfe’s writing is funny, straight-forward and insightful, which, when dealing with the core subject of her book, libertarian tech venture capitalist, PayPal co-founder and major Trump backer, Peter Thiel, is exactly what a reader wants. The publication of Wolfe’s book was incredibly well-timed and has recently been gaining almost as much press as Mr. Thiel himself, who, aside from explaining his support for our current president, has also been outed for bankrolling Hulk Hogan’s lawsuit against Gawker, something Thiel refers to as a “philanthropic effort,” not to mention the controversy over Thiel’s New Zealand citizenship and his business dealings with that country.

Finding and studying interesting subjects has never been an issue for Wolfe. Past interviewees have included Emma Stone, Sandra Bernhard, Tony Bennett, Clay Christensen, Carol Burnett, and Astro Teller.

Oh, it’s probably also worth mentioning, if you don’t already know, that Alexandra Wolfe is Tom Wolfe’s daughter.

Below, in a short interview with Wolfe, she tells us things like how she deals with difficult interviewees, who she likes to read, and what she likes to drink…


  1. How did you decide to become a journalist-slash-non-fiction writer?

Alexandra Wolfe: I interned at Dan’s Papers out on Long Island and they mistakenly entrusted me to write a restaurant review, and I broke the first rule of reviewing which is to not tell the subject that you’re a reviewer. My disclosure resulted in a dozen free appetizers, an endless rotation of pizzas and pastas and gratis tiramisu. I thought to myself that being a reporter had to be the best job around.

  1. What are you currently reading?

AW:    The Art of Racing in the Rain, by Garth Stein

  1. Are there any writers you admire?

AW:   Yes, a lot! My father, Christopher Buckley, Carl Hiaasen, Nick Hornby, among many others.

  1. You don’t have to name names, but have you ever had a tricky interviewee? And if so, how did you deal with them? Did you eventually get them to open up or did you have to write around the situation?

AW: Yes, I’ve had many subjects who have made me wonder why they agreed to be profiled in the first place. I interviewed one fashion designer who had just written a book, and every time I asked her a question, she’d say, “The answer is in the book.” I’d try to explain that I still had to fill the page, and couldn’t just replace the text with a link to the book, but she wouldn’t answer a thing. So I just looked around her office and pointed to things on the wall and asked where they’d come from, even down to the chairs. Those answers were at least much more interesting.

  1. If you could interview anyone, living or otherwise, who would it be and why?

AW:   I’d interview Eminem because I’m fascinated by the rollercoaster of his career and how he’s navigated through such colossal ups and downs.

  1. What do you do when you aren’t working on a story?

AW:   I like to exercise, see friends, go out to new restaurants and shows, and read.

  1. I know you are in the process of searching for a new topic for your next book. Any top choices yet?

AW:   I’m interested in the way drug culture is becoming more mainstream. I’m also interested in the art world and the show jumping world as a backdrop for either a novel or nonfiction book.

  1. What is your all-time favorite book or short story?

AW:   The Power of One, by Bryce Courtenay

  1. Your favorite way to waste time?

AW: Online shopping

  1. Favorite musician?

AW:   Ahmet Kilic

  1. Favorite restaurant?

AW:   Morandi

  1. Drink of choice?

AW:  Sancerre

  1. Best way to break an awkward silence?

AW:  Wait!

  1. Did your father ever edit you?

AW:   Yes, all through school, and sometimes I still send him my articles.

  1. Has he ever encouraged you to try fiction?

AW:   Not really. I’m sure if I asked him about it he would be encouraging though.

  1. If you weren’t a writer, what would you be?

AW:  A travel agent.

  1. Who makes you laugh the hardest?

AW:   My boyfriend would come in first, and Cleaver Greene from The Rake second.


Erin Hazelton is a graduate student at Columbia’s School of the Arts. Her writing has appeared in publications such as Vogue.co.ukVogue Russia and The Boston Globe. She lives in Manhattan with her husband and two children.

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