Ari Saperstein on Writing for The Cut
and perfecting your pitch game.
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Ari Saperstein on the importance of a good pitch and writing for The Cut
I’d say about 25% of the story ideas I pitch out haven’t gotten placed somewhere, but I don’t find it frustrating because I almost always have another idea that I’m writing or developing.
Ari Saperstein understands that pitching is a numbers game. But it’s one you can’t win without a good story.
The journalist and radio producer has only been pitching freelance articles since early this year, and he already has bylines in The Cut, The Boston Globe, Shondaland, and more.
This article about Cate Blanchett’s sunglasses was not easy to place. Ari tells me he pitched it 15 times before finding the right outlet. In a time when many of us might worry that our stories need news pegs, or that our expertise doesn’t align with everything that’s happening in the world, Ari has successfully placed stories that are unique, irreverent, and refreshing.
So let’s hear from Ari on his approach to finding great stories and writing pitches that land bylines.
What is one of your recent articles that you really loved writing and why?
I wrote a profile for New York Magazine about an artist named Ashley Lukashevsky. What made it such an enjoyable piece to work on wasn’t necessarily the writing part. It was the interview. I spoke with Ashley in-person, at her home in Echo Park, and it was so easy to talk to her. I didn’t have a list of questions I was reading off of — I was fully present, engaged and naturally in dialogue with her. That is such a challenge for me. I’m always editing in my head during interviews and it takes a lot of work for me to be genuinely in the moment and not checking off a list of quotes I feel that I need to get. And of course when it came to writing the profile, it never felt forced. And I think it comes across when you read the piece, too.
You've landed some really impressive bylines after just a few months of pitching. What do you think has been key to your pitching success?
I was definitely starting in a place of privilege by working part-time at KPCC, the NPR Los Angeles station. I think being associated with a place like that has probably helped me get responses from editors quicker than I might have otherwise.
Equally helpful is the fact that KPCC owns LAist.com, so I’ve had the chance to build up a couple of bylines by writing editorial versions at the outlet of reported stories I’ve done.
Undoubtedly, those two things helped when I decided to make a bigger push on freelance writing — but even with those advantages, having good pitches has always proven to be more important than good credentials.
You mentioned that you sent the Cate Blanchett pitch to 15 outlets before considering the pivot to fashion magazines. Has this been a typical success rate in pitch attempts vs. assignments? Could you share an example of another story and how many times it was pitched before you received a yes?
I’ve found that approximately 1 in 5 editors reply to a pitch. Sometimes that response is a “yes” and sometimes that comes sooner in the process than other times, and sometimes it takes a while. When I’m pitching, I think to myself: “If I want another response, then I should find 5 more people to pitch it to”.
Here’s a little look behind the curtain: I have four story ideas I’ve been pitching out in May. Two I got accepted and two I’m still working on getting placed. Here are the numbers for the outreach and replies on each pitch:
PITCH A: 16 emails, 4 replies (not placed yet)
PITCH B: 14 emails, 2 replies (not placed yet)
PITCH C: 15 emails, 3 replies (written and published)
PITCH D: 30 emails, 5 replies (written and published)
As you can see, 15 queries has often been the golden number. But that last one, Pitch D, with 30 pitches -- I was really adamant about it. I knew it was a good idea but I just needed to find the right outlet. Much like with the Cate Blanchett piece, after not getting traction initially I just had to sit and think about what possible verticals my pitch could fit into.
Editors are becoming increasingly difficult to reach as freelance budgets are being cut at so many outlets. What motivates you to keep pitching when your ideas are being rejected or you're not hearing back? When do you decide it's time to try a new angle or move on to a different story?
Every example I wrote about in the last answer is a scenario where I have an idea and I’m looking for somewhere to get it commissioned -- and for that approach, yes, it’s definitely a bit more challenging now that a lot of publications have frozen their freelance budgets.
Another approach is responding to calls from editors looking for articles on specific content. I know that’s been great for a lot of freelance writers at this moment, and it is a great approach for those starting out. I, personally, don’t do it as much because what motivates me is being really excited to write an idea, whereas it’s rare that a niche prompt from an editor generates an idea I’m as excited about.
I’m OK with rejection and blind emailing and doing deep dives for contacts -- but for others, those things can be big turn offs. It’s a question everyone has to answer for themselves: is it worth my time? For me, yes, because when I do the “work-for-hire” approach, it often results in writing that is subpar, kind of forced and not genuine, stuff that I wouldn’t want to include in a portfolio. But for other writers, going off really specific calls and prompts is great for their writing. To each their own!
For me, occasionally calls from editors line up with an idea I’ve been mulling over or they do prompt something I’m excited to write, but it’s rare.
I’ve found that having multiple stories that you’re pitching out simultaneously is extremely helpful. If you’re putting all your eggs into one basket, so to speak, then it can be a bummer if it doesn’t pan out. I’d say about 25% of the story ideas I pitch out haven’t gotten placed somewhere, but I don’t find it frustrating because I almost always have another idea that I’m writing or developing.
It's refreshing to see that you had success with something completely unrelated to COVID-19, at the height of stay-at-home orders when it seemed as though every story was about the pandemic. Can you offer any advice on how to come up with fresh story ideas that aren't pegged to current events? What's your process when you're trying to come up with a new story to start pitching?
What makes you excited? What’s something you know a lot about? Starting with those questions is a great place to begin. You want the editor to be as excited as you are about the pitch -- if you don’t believe in your idea, it’s hard to sell someone else on it.
I also find that making a headline is very helpful early on in the process. Can you simplify your idea down to its core? Making a headline helps me as a sort of a guiding point of reference as I start writing, a thesis statement to remind me what is exciting about my piece. And of course when it comes to pitching, a headline helps to capture an editor’s eye in the email and helps them to envision the end product.
There was always going to be an over-saturation of pandemic think pieces, and I think we’ve hit that point. In addition to the remarkable reporting being done by so many news organizations, we also all need a break from COVID-19 coverage from time to time.
So in this moment, another helpful approach for generating pitches is thinking about what’s been on your mind and what you’ve turned to for comfort over the past few months and why. I’ve been doing a lot of writing about film -- in no small part because that’s been my escape during this time.
It seems a lot of people are drawn to audio stories lately. I'm personally listening to podcasts like crazy—it's so nice to take a break from screens and listen to a story while I cook or go for a run. As a radio producer, can you share any storytelling lessons you've learned in audio that you think have benefited you as a writer?
In radio, when we make reported pieces, we’re always reading a script but doing our best to not make it sound written. I often think about how I can make my writing sound more like talking -- so I read all my pieces out loud. I overcomplicate my writing a lot, with overly formal language and run on sentences… which is such a bad habit because I want everything I do to seem like I’m talking to the reader, not like I’m giving a lecture. There are things you catch when you hear the words versus just reading it on the page.
What is one thing you wish you had known about the process of pitching, writing for a publication, and then having your work edited and published, before you got started with freelance writing?
Keep your pitch emails as short and clear as possible. Put yourself in an editor's shoes: Imagine you’re getting dozens of pitches a day, in addition to emails from your co-workers and office and ongoing projects you have to coordinate. How do you get that person's attention? And if they open the email, what are they seeing that will make them want to read the whole email and give it their attention?
I put my credentials in the first sentence -- “Hi, My name is Ari and I’m a freelance writer. I’ve written for publications like X, Y, Z” -- and then bold my prospective headline. And the headline changes the most from email to email. I always edit the email header and the prospective headline so that it best matches the editor and their outlet.
And my pitch itself is never more than a paragraph. So my format for pitching is: two intro sentences, a headline, a paragraph pitch, and a sign off. But that definitely took some trial and error to figure out.
There have been so many layoffs in journalism lately. Are you concerned about the sustainability of professional journalism? What gives you hope?
Honestly I am really concerned. We’re living in a time of uncertainty. It’s been heartbreaking to see so many journalists, writers and media professionals lose their jobs as massive layoffs are being announced at so many companies. It’s a scary time for everyone.
With regards to the sustainability of professional journalism… we are undoubtedly going to see major fundamental changes to so many fields over the next few years to cope with the effects of the pandemic.
Hopefully the pandemic is forcing people to confront systemic issues that have long existed and shown the importance of having better protection, benefits and severance for employees.
That’s all for today, friends. I’ll see ya next week.
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