Failing Fast: Why Making Your Mistakes In School Helps Your Career Take Off From Day One

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Miami Ad School grad and Lyft Associate Creative Director Brian Button on being a small fish in a big pond, getting out what you put in and how everyone looks short when standing next to Shaq.

Brian posing hard with his boy Leroy and with his main man, Shaq.

Brian posing hard with his boy Leroy and with his main man, Shaq. (For reference, Brian is 6’6″ tall.)

Miami Ad School San Francisco grad Brian Button has been getting lots of attention for the work he’s been doing at Lyft. After spending all of his career on the agency side, Brian’s associate creative director role at the ride-sharing company is part of a growing trend of brands bringing creative work in-house. It’s one of a series of developments generating new opportunities for today’s advertising art directors and copywriters. We had a chance to catch up with Brian and get his take on his Miami Ad School days and the in-house life.

Carlos Vazquez: So, what brought you to Miami Ad School?

Brian Button: I was attending The Art Institute of California in San Diego, spending all my time in the library studying advertising award annuals. I soon realized that the most-awarded students were coming from Miami Ad School. So once I got my degree, I knew that Miami Ad School was my next stop.

CV: Was there one thing you learned that really contributed to your success in school?

BB: You get out what you put in. This program ain’t cheap, so it’s important to treat it like a job. Work hard, be humble, stay curious, work hard (some more), and build your network.

CV: How did you get your first job, and what was the biggest lesson you learned there? 

BB: I got my first job (at Tribal DDB) through Jim Bosiljevac (more on him later). I learned that this industry is full of talented people and that we’re all just small fish in big ponds. There will always be people with more talent or more experience so it’s important to make an impact however you can. It’s important to work hard, be humble, stay curious… sound familiar?

“… this industry is full of talented people and that we’re all just small fish in big ponds. There will always be people with more talent or more experience so it’s important to make an impact however you can.”

—Brian Button

CV: What do you love most about being at Lyft?

BB: The immediate impact it has had on the work I create. Having spent a lot of time agency-side, I was used to projects getting pretty watered down or straying far away from the initial concept. There were too many layers and opinions that ultimately compromised the work. When I went in-house at Lyft, the work ended up getting produced pretty much the way we pitched it. Fewer opinions, more trust and everyone aligned on what makes great work. I’m lucky to work alongside such talented, trustworthy people that let me do my thing.

CV: What’s been your favorite project so far?

BB:  I’m fortunate to be able to touch a lot of projects that come out of Lyft, and we do a ton. But I’d have to say “Undercover Lyft” has been something very special to me. The initial opportunity came about pretty suddenly when we had a two-hour window with then-rookie Chicago Cubs third baseman Kris Bryant. He drove passengers around town asking them what they thought of Kris Bryant. I was talking to him through an earpiece, basically telling him what to say to all the passengers the entire time. (Check out the video below there are some scenes where he kind of subtly shakes his head because he doesn’t want to repeat the things I’m telling him.) From there we got to work with Jerry Rice, Danica Patrick, Shaq, Demi Lovato, Gronk, DJ Khaled, Odell Beckham Jr., Nick Jonas—swoon—and more. No matter how prepared we were for each shoot, they ended up being the most frenetic, stressful, off-the-script improv shoots I’ve ever been a part of, and the most rewarding. It’s been super fun to lead a project like that.

CV: For the newbies out there, what exactly does an Associate Creative Director do?

BB: The ACD role at Lyft is a mixed bag, probably like anywhere else. Some days I’m writing copy for social posts or banners. Other days I’m leading a pretty ambitious project like Undercover Lyft or an April Fool’s campaign like Lyft Mono. Mostly it’s creating and leading brand campaigns, working cross-functionally with our brand and marketing peeps, and making smart-ass remarks whenever possible

CV: So, if were to walk up to you and say, “I want to be a copywriter.” What would you tell me?

BB: Find your voice. As a student—maybe it’s not all that evident—but you’re all going through the same motions. You’re learning the same stuff, probably working on the same brands, which means you’re going to end up with the same book (not identical but, you know, maybe not that different from the next one). So the biggest differentiator is a writer’s voice, and the more unique the better. Find inspiration. Read a bunch. Study the award annuals (seriously, study the shit out of them). Know what made Ogilvy different from Bernbach. Know that Neil French and Jim Riswold were badasses who did things their way (then learn how to be more like them). Be a sponge. And write a ton. It’ll likely be garbage at first but you have to get in the habit of going through the bad to get to the good. It’ll be easier once you have a voice.

CV: What were your favorite things about your Miami Ad School experience?

BB: Learning Humility: Doing this job well isn’t easy even when you’re good at it. Starting from the bottom was tough and humbling. Looking back, I should have better practiced what every place now preaches: fail faster. It’s part of the process and there’s no place where failure is more evident than in the first year of Miami Ad School. Learn to love it.

Building a Network: I’ve met some of the most interesting, talented people through Miami Ad School. I still stay in touch with them, whether they were instructors or fellow students. I’m thrilled to see a bunch of my friends going on to be creative directors (and beyond) and at some of the top agencies winning the top awards.

“The Grind”: At the time, doing 10 ads or writing 100 headlines seemed impossibly daunting. Now it’s just the halfway point. Because I wasn’t very good, I had to work harder than most just to break even. Miami Ad School is a good place to invent, practice and hone your work ethic. Put in the work now while the stakes are low. Be relentless. Outwork your classmates and make an impression.

CV: Was there one connection you made while in school that was especially significant?

BB: Two words (and a hundred syllables): Jim Bosiljevac. He was my very first Miami Ad School instructor and made a lasting impact on me. He took all my half-thought, hare-brained ideas and helped me turn them into pretty good ads. I stayed in touch with him throughout my ad school years, sending him garbage work and asking if he thought it was any good. I may have taken him out for a beer or two as well. Apparently he thought I was salvageable because when Tribal DDB (now known as Tribal Worldwide), was looking for a writer, he put my book on top. Three months out of Miami Ad School I was gainfully employed, thanks to Jim. Ultimately he became my creative director, which led to a ton of broadcast spots, life lessons, and more than a few late-night bourbon samplers.

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