My caller ID read: “Gay Talese.”
The byline I had once pinned on my wall was now flashing across my phone.
Just one day earlier, I’d emailed his publisher on a whim—I’d been rereading Talese’s iconic 1966 Esquire profile of Joe DiMaggio, the former Yankees star and husband to Marilyn Monroe, on the subway ride home. I’d forgotten how good it was—the way Talese casually drops details that build entire worlds, like that DiMaggio, who still holds the longest hitting streak record in baseball, “used a broken oar as a bat” as a kid. Or that when fishermen like DiMaggio’s father stepped out of bounds, they’d often find “gasoline poured onto their fish.” Or that the first thing the Yankee did upon waking was light a cigarette.
When I got home, I opened my laptop to search for his publisher. I figured out her email address and began writing a message for Talese, now 91, which I never expected him to see.
“People don’t write like that anymore,” I typed. “I don’t write like that—but I want to.”
The next day he called me. He sounded energetic yet transactional, almost like a bank teller.
“I know this is sudden,” he said. “Would you like to come over this afternoon to talk about writing?”
He told me to jot down the address to his Upper East Side brownstone and meet him there in about three hours.
As I sat there, stunned, I reminded myself: this is why you cold-email your heroes. Because sometimes, and more often than not, they respond.
For as long as I’ve been literate, I’ve been writing to strangers. Sometimes it’s to people I admire; other times it’s to someone who has something I want. That was the case in first grade, when I penned a note to a woman in my neighborhood, asking if I could see her backyard, because I passed her property every day on the way to school, and always wondered—what was that red thing in her woods?
Turns out it was a pagoda. I know this because a week after I placed my letter in her mailbox, she invited me into her home.
By fifth grade I was writing fan mail to my favorite authors, including Catherine Forster, a paleontologist specializing in the link between dinosaurs and birds.
When I checked my family’s mailbox a few weeks later, I was stunned to see her name in the top left corner of an envelope and my own handwritten on the front.
I waited until dinner that night before revealing it to my family, running into our kitchen and presenting the letter with quivering hands.
“Do you understand what this is?” I squealed. “This is like a letter from God.”
Over the years, anytime I’ve felt lost, I’ve written to my heroes for advice. In my 20s, when I was still sore from a breakup, I reached out to the queen of lonely hearts: Ashley Iaconetti, a former contestant on The Bachelor. In 2015, she became an overnight meme when she wept on national television over her crush, Jared Haibon. I wanted to know: had I found my Jared? I consulted Ashley.
“I would try to get a hold of him,” she emailed back. “I don’t know if that’s going to open the whole can of worms again, and if that does happen you could hurt all over again, but I think the risk is worth the possible reward.”
And it was, kind of. Until he ghosted me.
Today Ashley and Jared are married—and so is my ex.
Then, in 2018, I fell in love with a stranger at a party while in grad school—he was there with another woman, laughing by the fireplace in a turtleneck. Two years later, I couldn’t shake that memory. So, I googled what I remembered about him—his first name, that he worked in film—until I found his Instagram. When I messaged him cold for a date, he said yes.
The date was less exciting—he lacked the charisma I had envisioned. That’s when I learned that not all cold emails lead to success, but they’re still worth sending if it comes from the heart. If you treat your words like they’re powerful, you’ll usually get a response.
Ask my enemies. Whenever corporate America has wronged me, I’ve gone straight to the top.
We’re hosting our first live debate on September 13 at the Ace Theatre in Los Angeles! Has the sexual revolution failed? Come argue about it and have a drink. We can’t wait to meet you in person. You can purchase tickets now at thefp.com/debates.
In 2021, when my internet provider could not log me in to my online account, I wrote to the CEO.
I titled the email: “Re: Q3 Earnings Report.”
And in the first line of the body of the text, I wrote: “Sorry, I made that subject line up just to get your attention. I’m actually emailing about a really frustrating customer service experience I had.”
Forty-five minutes later, I got a call from corporate headquarters.
The problem was solved that day.
These days, everyone says networking is the route to success. But I’ve always been a strong believer that any door can open if you score the right invitation. My advice? Don’t ever ask to “pick” someone’s brain. The trick is to get inside their brain. Start by googling them, or rereading or relistening to their work. Why do you like it? Tell them that. Make them know they matter. A good cold email is not unlike a good love letter. It should make you feel vulnerable. Cathartic.
June 18, 2022, was one of those days. I was racing to a yoga class, listening to Bari Weiss’s podcast, Honestly, when I heard an ad at the end.
“We’re looking to expand our team,” Bari said, before giving out a general email.
I put in earplugs and began typing immediately, forgetting all about my class.
And for the next three hours, I wrote. It was the worst case of the cold emails I’ve ever had (or possibly, the best case)—a state somewhere between mania and clarity.
I emailed Bari, a journalist I’d been listening to for the past six months, about how I was bored—and maybe even a little disgusted—with mainstream media. I had worked for Politico and NPR affiliates, I explained, where “reporting” often amounted to calling the Democrat to get the bad quote about Republicans, and then calling the Republican to do the same. I was sick of it—and in fact, I’d started spending my free time not writing news at all, but essays.
Each essay started with a personal confession: “I dated Casey Anthony’s former fiancé’s brother,” “I get Botox,” and the one that weighed most heavily on me, “I’m afraid of being cancelled.”
That last one is the essay I sent to Bari.
Two days later, one of her staffers called me about a job. He told me my letter stood out among the thousands of others who wrote in that weekend.
A month later, I got a call from Bari herself. Eventually I was hired full time. At last, I had my first-ever writing position after years in radio and podcasting.
When your letter gets you your dream job, you write a lot more of them.
So when the spirit moves me, I act on it, like I did last month after burying myself in Gay Talese’s story on the subway. That’s how I ended up in his basement studio, surrounded by boxes of his notes, each one decorated with a collage of his muses or story subjects.
“It’s the first thing I always do,” he shrugged, showing me the box for his reporting on Dr. Nicholas Bartha, a man who blew up his New York City townhouse in 2006 to avoid selling it. “While I’m making them, I’m just thinking about the story. It helps me get into the mindset.”
Talese, like his longtime friend, the late writer Tom Wolfe, is a formal man. He might have dropped a few f-bombs for emphasis but he was buttoned up in a khaki suit, even quickly taking off his fedora when entering his home (Talese’s father was a tailor). There are no windows downstairs, he explained, but amenities include a shower, a “napping space,” and a kitchen stocked with instant oatmeal.
We spent an hour talking about why politics is “boring” to cover, and how he’s never owned a pair of blue jeans (“Why would I need those?”). When I remarked that cancel culture is stifling journalism, he agreed—and I felt an immediate kinship.
I lifted my fist. “Pound it,” I said, beaming.
He raised his fist to touch mine.
Before I left, he passed me a copy of his upcoming book, Bartleby and Me, set to come out next month. In the top left corner, he’d typed out a tag that said, “To: Olivia Reingold” and “From: Gay Talese.”
Beneath it, he had squeezed in his signature, in blue ink.
“If you want, I’ll see you again,” Talese said as he waved me out the door.
I’m already planning to stretch his half-invite into a full one. I just have to find the right words first.
Olivia Reingold is a writer for The Free Press. Read her last piece about America’s new homesteading movement here.
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