Why creatives in advertising should embrace data science and data mining — an interview with Les Guessing

Elizabeth Press
4 min readFeb 28, 2023

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Contextualizing our world with data, part 1: Advertising. Les Guessing has a high school degree (barely) but has managed to find great success as an Emmy Winning Copywriter / Creative Director in Los Angeles (and beyond) in advertising — the marketing arm of Capitalism. Over the last 10 years, he has become hellbent on using data/Data Science/Machine Learning and aspects of Artificial Intelligence (especially NLP, Natural Language Processing) to make advertising creative more insightful, more efficient, more impactful, and funnier. He explains why creatives should work with data because. Among other reasons, the creative mindset enables them to look at data and see something from an entirely different perspective than data people.

Published on D3M Labs by Elizabeth Press / February 27, 2023

When did you decide you wanted to be a writer? How did you get into Copywriting?

There was a girl I had a crush on in high school, and I wrote her these very emotional love letters. That was the first time I realized you could really enjoy writing outside of just doing a school assignment — probably the best training for copywriting. Copywriting is about connecting with people.

As a poor Tennessee teen, I wanted to be Jack Kerouac (“On the Road“). I ran away to Florida and lived in my car and wrote every day. I eventually went to college and took a lot of classes I was simply interested in — radio DJ, photography, film. I ultimately wrote and shot a short film, and that inspired me to move to Los Angeles and try to write screenplays.

I got really sick during the 1984 Los Angeles Olympics and couldn’t get up off the couch, so I watched almost all of it. They had amazing commercials, and I thought that was really cool. I thought that, until I became a screenwriter, I would try to write commercials.

I took a commercial writing class at UCLA with Jack Foster, a famous LA Creative Director who wrote a book on “How to Get Ideas“. (I’m in it.) That started me thinking about copywriting. I took a couple of classes at The Ad Center with some super talented teachers (Mark Montero, Rick Carpenter, Larry Johnson), built a portfolio, and started sending it around. Got my first job at Ogilvy.

How did you win an Emmy?

I grew up in the South where it‘s mandatory to play baseball and football. so I got hired to pitch the NFL on Fox. We won it and I become the Creative Director. It was the most fun job ever. No list of mandatory stuff to say — just write funny joke promos for NFL football players. That year, we tied with W+K/Nike for the Emmy.

What is copywriting and can you explain the role of Creative Director?

Copywriting is basically writing any kind of advertising. A Creative Director manages creative teams (Copywriters, Art Directors) and creative projects. You need to be a good relationship person to manage people who are notorious for being fucked up J. A lot of creative people have some wonderful weirdness in them. They are not always the sanest people. A lot of egos, angst, people trying to get ahead.

You also have to be a strategic thinker, have a good creative sense, and be able to present and sell ideas. Being able to mine data for that strategic part, and having a sense of how that can turn into great creative ideas — I believe is the future of ad creative.

Do you want to read more about how creatives in advertising should use data science and data mining?

  • Les’ personal journey into data science.
  • How involving creatives in data can get MORE value out of data.
  • Do creatives need to learn math? And how much?
  • How are new technologies such as Chat GPT and low code/no code enabling non-technicals entry into data and thereby expanding what can be done with data?
  • Will AI destroy jobs in advertising?

Read further on D3M Labs https://d3mlabs.de/?p=1074

Who is Les Guessing?

Les Guessing has a high school degree (barely) but has managed to find great success as an Emmy Winning Copywriter / Creative Director in Los Angeles (and beyond) in advertising — the marketing arm of Capitalism. Over the last 10 years, he has become hellbent on using data/Data Science/Machine Learning and aspects of Artificial Intelligence (especially NLP, Natural Language Processing) to make advertising creative more insightful, more efficient, more impactful, and funnier.

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