This week Eliza interviews freelance copywriter and regular Bold Italic contributor, Drew Hoolhorst. Follow Drew on Twitter via @drewber and on his blog, Rocket Shoes. 

You, Drew Hoolhorst, are a master storyteller. Who do you consider your earliest influences, and how has your storytelling evolved over the years?

Thank you, interview question, that’s incredibly kind of you. Ready for the hokey answer? My grandfather was the best storyteller I’ve ever met in my lifetime. Since I was a tiny babe, he would tell me the most grandiose Big Fish-esque lies you’ve ever heard and I just couldn’t get enough. There was sort of something great about it…his “art” of lying, really. I know that sounds horrible, but I loved how he could lie to me and tell these tales of absolute grandeur and even when I knew they were lies or at least stretches of truths, I just loved hearing them. The man just knew how to make you feel like you were the only person he was talking to, or had EVER spoken to, and that’s an art.

I’ve always tried to mimic that in any form of writing or storytelling: say things that readers and listeners feel like are just for them. In the best writing, that’s there, really. You are speaking to a million people, but if it were just one you’d tell it just as personally.

Some would say you are well known for your contributions to The Bold Italic. How would you breakdown your creative writing process?

It’s simple: come up with a great idea when you’re talking to people you care about. Laugh with them about it because you all agree that this is something you all feel and could talk about for hours. Every time: that’s where you start. The best stuff comes from conversations with people you care about, because when you’re just shooting the sh*t, that’s when you say the random Seinfeld-esque stuff that really sticks in your head… everyone’s head. After that?

Get a deadline, wait until the last minute, panic and then write. Don’t ever write ahead of time. You’ll write a huge piece of shit. Panic, man. It brings out some wonderful stuff, in my opinion.

Having worked as a freelance copywriter for SF advertising agency EVB, how do you gauge what style of writing will be the best suited for a particular audience?

In all honesty, you just listen to the client and then (in my case, because I’m small fry) you don’t wait to hear what your CD’s have to say to you, you listen to what they say to the other important people in the room that are just like them. Basically: what bosses say to bosses? Write for that audience. Because that’s when everyone’s really being completely honest, and that’s when people say the off the cuff stuff that tells you exactly what we all think we should be writing or concepting to.

As a freelancer what is your best self-motivation tactic, and what advice would you give to professionals considering freelance work?

Freelancing has been a funny thing. In the beginning, it’s like sex: you have no idea what you’re doing and you just lie incessantly to get everyone thinking you’ve been doing this for ages. I try to always remember that beginning part because after each job, you’ve sponged up a little more knowledge from some really amazing creative people and you’re that much better than you were when you walked in their door. Basically, every time I can’t self motivate, I remember that I used to have no idea what I was doing, and if it’s this much fun now, how much fun will it be if I keep my ass in gear? You can always get better, and I try to just remember that.

If you’re considering freelancing, just remember that it’s like getting a new job all the time, always. It’s hard, but it’s also incredibly fun to get a new uniform every month or so.

You worked as a social media strategist for the creative agency Mekanism back in 2006. What has surprised you about the evolution of social media, and do you have any predictions about how it will change in the future?

What’s surprised me is how far it’s come since then. I mean, I remember explaining to senior creatives how “the youtubes and the tweeters” worked back in the day and how strangely slow they were to grasp it and/or take it seriously, and it’s just really funny how now all of them add you on a social network every other day like a parent trying to add their daugther on Facebook (I say in jest, my bosses at the time were incredible people.) I think things like Vine have jumped the shark a bit, where it’s really awesome but…I don’t know, do we really have to have THAT short of an attention span? I like what companies like Medium are doing in trying to Goldilocks the blog/twitter conundrum a bit, and I think service apps are only going to get more amazing. Not a bold prediction, I know, but I think people are going to back off of the hyper short attention span stuff and focus more on making a service that’s “food delivery for blank” for every last thing on the planet.

You have a self-proclaimed ‘black belt in feelings’. What exactly do you mean by that?

It means I was raised by a single mother and have an extensive shoe collection and am happy to talk about feelings until both of our ears hurt. (I’ve just always been the sensitive guy my whole life, guess it just sort of stuck.)

What are your favorite events and communities in SF?

I love Noise Pop and Outside Lands to an almost unhealthy degree, and I’m so happy that OSL is finally getting to the level of Lollapalooza and what not. We deserved to have something like that here in SF. We’re a bunch of “neener neener” artisanal fans, it’s only right we get to see bands that no one’s ever heard of yet.

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About our contributor // Eliza Dropkin is a lover of live music, good food, and beautiful places. Connect with her on Twitter via @elizadropkin.