I’m not a publicist, but I’m probably the closest thing most of my friends with businesses or side projects have to one. It makes sense—In 2012, I was a junior at business school and got myself into Hypebeast. I had blogged for years, but little professional writing experience prior. In 2013, I got myself into The Globe and Mail. Between 2014 and now, I have written for HuffPost, Quartz, and Fast Company. I worked as a staff writer for Lifehacker, and I’ve even helped a few friends pitch their businesses to publications. But the best product of my pitching is probably… me.
Pitching is hard work. I have friends who spend hours building hard software products tell me they hate the pitch.
Let’s put that into perspective: they spend hours debugging or collecting user feedback, but in comparison, the hours clicking after the Send button are their own special kind of hell. It’s painful—putting yourself out there, mostly meeting with the stinging rejection of silent indifference, speaking—or shouting—to the ether.
This post will be most useful to writers, but definitely is applicable to entrepreneurs with side projects, corporate people managing by press release, anyone who wants to write and work at leading thinking, etc. I’m going to show you how I pitch, which is mainly by developing a story well enough and then introducing myself before that.
When to, and Not to, Pitch
99% of the time, I’m pitching because I want to get an idea from my computer or notepad into a publication or a blog. Good publications have all sorts of benefits—credibility, a built-in audience, occasionally a bit of cash, and backlinks. I don’t pitch every story—for example, I didn’t do it with this one.
(Note: These blog posts are for fun, and deliberately not as polished. And yeah, for anyone about to go there, I occasionally write about pitching publications for fun. Don’t get me started on Kanye West.)
I pitch the professional stuff—for example, whenever I’m writing for one of Medium’s editorial group publications, guest posts to promote my book, and other new articles for credibility or cash.
Sometimes, pitching is just about quantity and timing. Most publicists approach it like that, mailmerging mass emails with a really big media list. And it works, sometimes!
But other times, one well-placed pitch with a strong relationship can go far—for example, The World According to Kanye got into Hypebeast with one email. Then it spread like wildfire everywhere else. I will cover it another day and link back here once I do. But for now, my approach is middle compromise of the two—develop the story, and then tailor it just enough. If you’re struggling to frame your current pitches, here’s some stuff you could consider:
My Current Story Orientation
You may have learned the fundamentals or orientation in storytelling in school—5 W’s and a H (Who, What, When, Where, Why, and How). That’s probably the most fundamental lesson with pitching.
I’ve since refined the process a little more. I see pitches as atomized versions of an article—so they’re the “painted door” and not an actual door yet, to see if any editors take it up. It’s also to test if the idea is actually good enough to publish. Here are the questions I ask myself:
What makes this story relevant? Why is this a good time to talk about it?
I hate that this is at the top of the list, but it’s actually one of the most important. I do my best to tie in relevance with exploring timeless stories—it’s better for residuals if you’re writing at Medium—but if it’s your first time reaching out to a publication and building a relationship, it’s best to start with a really, really, relevant story. Best example of this is my Yeezy Gap story for Marker—I wrote this pitch in 15 minutes on a Sunday night figuring I had very little to lose:
A couple of months ago, Marker covered the decline of Gap. Then, last Friday, Gap announced that it would be doing a 10-year licensing deal with Kanye West’s Yeezy company, and stock prices spiked as high as 42%. For comparison, Spotify’s deal with Joe Rogan bolstered its stock by around 11%. Gap is betting significantly on this, saying in The New York Times, “At the five-year point, Gap is hoping that Yeezy Gap will be generating $1 billion in annual sales. For context, Gap’s brand brought in $4.6 billion in global revenue last year.”
On Friday, Kanye took to his Twitter account to announce, along with his Gap deal, a myriad of concurrent and new projects — such as Yeezy foam runners that sold out in minutes (working with Adidas and made in the USA), a preview of his new ecommerce site, and his upcoming collaboration with Dr. Dre, a new version of his most recent album.
We are witnessing a dramatic revision of how a “celebrity” can create and extract value from the market. Kanye, for years, has fought against the traditional endorsement model. Through his initial (terrible) deals with Nike, he knew he had more to offer. He knew he needed corporate infrastructure, as he went $50+ million into personal debt trying otherwise.
I want to document Kanye’s journey with Yeezy, and to talk a bit about the Yeezy value propositions to its stakeholders, and how different Yeezy is from Beats by Dre and Tidal (and possibly other sizable businesses by recording artists).
Please let me know if this sounds interesting. Thanks!
Outside of running it through these questions, I did things completely the opposite of what I usually did there—I pitched one story (usually I pitch two or three), I wrote it up quickly, and I sent it on Sunday night. But, that’s what got me into Marker! So the insight is, no process is bulletproof, and shipping today (but possibly releasing later) is usually a good idea.
What makes this story interesting to you?
This sounds really obvious, but if I’m interested in researching and writing it, readers will be interested in reading it. Plus the research writing process often takes at least 10+ hours, often 20–30, so I might as well spend it doing something that draws me in. This helps kill off more opportunistic, commodified, story ideas that I can leave to the other writers—it enables me to do something with my own perspective.
Can you make it a sweeping piece of history, with scope and ambition?
I don’t mean the question as seriously as it sounds. I just want to add context here. Why is the story important? What is the history before this story? If this story were a line on a continuum, what comes before it and what comes after? I’ve found this to be the difference between good and great articles.
Some publicists I’ve worked with before ask a variation of this question: What are you the first at? This is also a valuable question—can you hone in enough on a specific geography, community, or category to be the first at something? What makes this specific story newsworthy?
What hypothesis deserves more attention? Are you suggesting a new hypothesis? Reporting is not enough — what is your opinion?
Being a contrarian is nice, but it’s not worth being argumentative. What is the truth or nuance you are revealing here? That will be the thing worth talking about. It’s most valuable to talk about something new—bring the thinking forward, that’s what leading thinking actually literally means. Don’t contribute to the echo chamber, don’t only rejig other people’s ideas.
In other words, do the work to develop an opinion and a new, stronger, hypothesis so people might actually learn something. If every writer did this, we would have a better internet.
What actions do you suggest for the reader?
This is, historically, what I’m most familiar with, having written at Lifehacker. I put three or five actionable tactics to what the reader can actually do so that they can apply the article to their lives. Sometimes this isn’t as relevant—for example, a story covering WeWork’s resurrection—but other times, this is the story—for example, a story covering improvisational comedy.
Does this story fit into the publication’s focus? Has the publication written a “sufficiently” good post about this topic already? If not, who else has written about it, and why would they want to consider this? If they have, what new lessons are you telling them?
This is the other point about context—what makes it fit this publication? What evidence do you have? This is a positive signal to whoever is reading the pitch that you’ve done the work of seeing what they’ve written before.
Switching Up the Story Orientation
The method is modular—simply by changing the last question, I can make it flexible enough for other publications—and it also is a quality check. A good idea can make it through this process breezily, a bad idea will have some trouble and require more framing.
Sometimes, publications ask that you don’t pitch—that you submit a rough draft instead. This method is just as effective. A lot of times I find myself at 400 or so words just by filling this thing out, and then I’ll develop the story further and kick it to 750–900 words. If you read my latest work closely, you’ll see that I’m literally almost just answering these questions.
This is bound to change—consider this a snapshot into how I pitch for now, and not a permanent process. There are so many possibilities—I could probably add more characters and motive in, or challenge my own perspective more often. Plenty of work still remains, and I am still on day one of being a writer.
Good pitches require reading…
Thanks for reading this. Stay tuned, sign up for the Best of Books reading newsletter on the sidebar (three great books in your inbox every month), and see you around!