Reinventions: Benjamin Levy

'I hated seeing good ideas die over and over because they weren't being sold well'

Reinventions profiles people who've made big pivots. Meet Benjamin Levy, who went from award-winning New York creative director to pitch and presentation coach, on a mission to help agencies sell better ideas.

What were you before? 

In my past life I was a creative director, with a portfolio ranging from K-Y to Coca-Cola, and everything in between. It had its highs (getting choked out by an UFC belt holder on production) and its lows (less of a 9-5, more of a 9-10:30).

What triggered your reinvention?

I hated seeing good ideas die over and over because they weren't being sold well. In a pitch, it's not the best idea that wins; it's the most persuasive argument. As a creative, you're taught how to generate ideas, how to build on them and make them better. Nobody teaches you how to actually sell them.

I spent the first half of my career as the world's worst presenter. I spent the second half as a really good one. But that led to a different kind of problem: I was being asked to pitch constantly. Very flattering, but I'm just one guy. Along with those client meetings, I needed to find time to review work, write scripts, and do any one of a hundred other things (like pee).

When my early attempts at cloning failed, I moved on to the next best thing: a course for pitch and presentation skills that I could run for co-workers.

What did the first steps look like?

I sat and wrote out everything that I thought went into being a good presenter. Then I built a syllabus, picked four victims co-workers, and started teaching. It wound up working well. Really well, in fact. That first syllabus got passed around, and I started getting calls from people asking, "Can you do this for us?"

I've always loved teaching, and was tired of putting my family second to my career. It was a huge decision to make, but ultimately not as hard as I expected it to be.

What was one hard obstacle to overcome?

I wasted a lot of time trying to be perfect. I thought if I worked hard enough, revised enough, that I'd suddenly look at the business and my crippling imposter syndrome would say, "Now it's ready." But that's a myth you tell yourself. An excuse to procrastinate. I was ready before I even left my job. People were literally asking me to coach them. Clearly my business's not-quite-perfect status wasn't bothering them. 

Now I have "Don't wait until you're ready" written on the whiteboard in my office. Right beneath it is "Don't forget to pick up almond milk." Words to live by.

What was easier than you thought?

The actual coaching. I steeled myself for nightmare clients—people who wouldn't put in the work, who would argue, or who would view coaching as a punishment inflicted on them. But that hasn't really happened.

Sure, some people don't do their "homework" every time, but I still see breakthrough moments and transformations, even in those clients. On the whole, people are incredibly grateful for the coaching, and I'm just as grateful to them.

What's something you learned along the way that other people, hoping to do something similar, should know?

I'm a big believer in building yourself a personal board of directors. People you can run crazy ideas by. People who will keep you honest. People who will believe in you during moments when you don't believe in yourself.

If you don't have people like that, go find some. They can be co-workers, best friends, or people you've met only on Slack groups. They can't be stuffed animals, though. Mr. Bear is a wonderful confidant, but he's not gonna tell you you're being too cautious with your rates.

Did anyone or anything inspire you along the way?

Bruce Lee. No, seriously. He developed his Jeet Kune Do style by incorporating elements of dance, fencing, boxing, and more. Obviously the foundation of my coaching comes from my agency experience. But if you're going to pitch an idea, there are a lot of things worth stealing from the worlds of comedy, professional sports, acting … even children's books and jazz. Just because most agencies have pitched a certain way for years doesn't mean it's the only (or best) way to do it.

What has this fundamentally changed for you?

I get to help people directly now. As a creative you're helping your clients, but that's just a side effect of helping the brand they work for. Now I get to look my clients in the eye, and everything I do improves their lives directly. It's pretty cool.

Do you think you could go back/do you want to?

I don't think I could ever leave advertising completely. I love writing, concepting and solving brand problems. I still freelance when I have time, to make sure the skills I'm teaching are still relevant (especially in the era of pandemic presenting). But as far as that 9-10:30? Not sure what it would take for me to go back there right now.

Tell us your reinvention song.

It's either "The Other Side" from The Greatest Showman or "Remember The Name" by Fort Minor. That single sentence probably says more about me than all the rest of this put together.

How would you define yourself now?

I coach creatives to pitch and present better so your agency's best ideas get made. Distilled from over 15 years of creating and selling award-winning ideas, my approach has helped everyone from interns to executives. If you want to stop selling your "second-best" ideas, deepen your bench of client-facing folks, and conquer your Zoom slump, find me at

Reinventions is a questionnaire series with people who are making pivots in their lives. If you're going through a reinvention and would like to be interviewed for the series, please get in touch.

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Angela Natividad
Angela Natividad is the European markets editor at Muse by Clio. She also writes about gaming and fashion, and whatever else she's interested in, really. She's based in Paris and North Italy, so if you're local, say hi. She might eat all your food.

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