Deez Interviews: Meet the copywriter who wants you to give a shit about something

Happy Friday, Deezers! In this week’s Deez Interviews, we’ve got Cole Kennedy (of this New Yorker co-living trend piece fame!) dispelling Mad Men myths and getting real about combating writer’s block.

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The interviewee: Cole Kennedy (follow at @cdohertyk)

The current job: Copywriter at Starry

The hustle: Starry is a small company where I was the first in-house writer, so I have a lot of different projects across anything from product to marketing to writing job descriptions.

So copywriting/advertising in general is notoriously hard to get into. Tell us about how you got your first job!

Tell me about it. I feel like agency people have never heard of the chicken-or-egg thing, because almost every position has that dreaded “agency experience preferred” line — even internships. I studied creative writing in school, and my first gig after graduation was an internship in New York City at Foursquare. I was crazy lucky to lock that down, and looking back, I think what made it happen was a passion for the industry. I wasn’t just a writer; I was a writer who loved tech.

After Foursquare, I was deep in the interview process with another start-up called Handy, until I got the kindest rejection letter of all time, saying they liked my work but needed someone with more experience. I ended up moving back home, which was Minneapolis at the time, because even with a bedroom-that’s-really-just-a-closet sublet in Bed-Stuy, being unemployed in NYC is not a good idea.

One day, I got a call from a recruiter at Handy asking how my search was going, and if I’d be willing to chat with them again. Of course, I said yes. I was dying to get back to NYC. It turns out that they had interviewed a lot of copywriters after me, but none of them had the same desire to do product writing. They were all agency writers. So, I got the job and went back, and I think that speaks to the whole concept of skills-as-table-stakes. You need to be a good writer or whatever, but you also need to demonstrate genuine passion and interest in some particular niche.

How does actual real-life copywriting in 2017 differ from a Mad Men episode?

Oh Mad Men. I think in some ways, not a lot has changed, and obviously in others, Mad Men is totally foreign. We aren’t sitting around working on print headlines all day, but it’s not unheard of to spend hours going back and forth on a 43-character headline for some sign-up form buried on the website.

Maybe the biggest difference is the spread of work; you don’t get to work on one specific client, let alone a single medium. I’m constantly adapting language to different contexts; one minute it’s a marketing email, then it’s product onboarding, then a subway ad.

I should caveat that by saying that’s been my experience at start-ups, so it could be different elsewhere. For me, though, it’s perfect. I always revert to this aphorism about creative writing that it’s just the process of taking the abstract and making it concrete for people, so copywriting is an expanded version of that. One message, many channels. (I am beginning to sound like a brandspeak voodoo book.)

Any go-to ways to combat writer's block?

Just start pounding out words, the shittier the better. Treat your computer like one of those typewriters where you had to pull a lever to change the line; just crank out line after line after line of crap. Then, maybe, have a drink. I mean, unless it’s early in the afternoon.

You can’t take a nap in your office because we have open plan offices now and nap pods are a myth. I stole this from a guy on Medium named Luke Trayser who gives excellent copywriting advice, by the way. Here’s his version.

If someone wants to go into copywriting but they don't have the English/journalism/advertising degree, what's the best way to stand out?

Give a shit about something. I happened to love tech, but I wasn’t a technical person, so I assumed that I couldn’t get into the game. I was wrong — like I said before, whatever skill you have is table stakes. The rest is up to passion and savviness. I think people should be careful with websites and blogs. I had a blog in college and killed it because it was dumb, and I would be horrified if employers saw it now. I don’t care how good a student you are; most of the work you do in undergrad is not good, and you will be embarrassed by it.

I was told that the main reason I got my internship at Foursquare was because my cover letter was authentic. Don’t skip the cover letter and write something specific but succinct for each role you’re applying for.

The last thing that I can recommend is to take on a side project. I know, it takes time and energy and money, but it’ll make your portfolio way more legitimate. Don't make the mistake of thinking a slick Squarespace landing page will land you a role — it needs content. If you don’t have enough work to cobble together a portfolio, make something up. Or use your imagination — create a new brand for some garbage old company, just because it’s fun.

You've done work at a lot of early-stage companies? Do you recommend these types of places for young people to get their start?

I’ve always been interested in tech, so it feels somewhat natural to me that I wound up here. Like I said before, the agency world is nigh-impossible to break into, but true to their nature, start-ups are often more willing to take risks on young talent. Show them what you’ve got and you’ll get a good shot at getting an interview.

Once you’re there, there’s a good chance you’ll get to work on projects that have way more impact than you’d get in an entry-level role at a huge agency. Do not, however, join a start-up because you think it’s the next Facebook and you’ll get rich. If that’s your motivation, you’ll be super disappointed.

Also, the thing about snacks and beers? It’s so true. Or mostly true. That’s probably the way we’re most similar to Mad Men.

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Zayummm, Cole’s straight talk has got me feeling all mOtiVaTeD and shit now on a Friday afternoon — highly recommend bookmarking this for a day when you’re feeling less-than-inspired about being young & job hunting (say...Monday?), and keep an eye out for his work!!

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