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

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.

At what point did you get interested in data and AI?

I had seen a funny, powerful hypnosis act while I was in college. I started studying hypnosis and NLP (Neuro Linguistic Programming). At the heart of NLP is the idea of building mental models (especially with language) of how people who do things well, do them.

A buddy of mine teaches [1] stand-up comedy. We used to talk about how we could model comedy. Think about it, how does an entire audience, of all ages, simultaneously recognize something is funny? There must be underlying algorithms of some sort.

I had an epiphany one day and discovered/modeled/wrote about 80 algorithms for how jokes work. That got me interested in how I could use an aspect of AI called NLP (Natural Language Processing) to make that possible. (I’m currently writing a book and working on using pre-trained Large Language Models to implement those algorithms. For all its awesomeness, ChatGPT ain’t fucking funny.)

Around 10 years ago, I was part of starting a Meetup group called Data Science Los Angeles. I would go to meetups and conferences and shoot video. I took a LOT of classes. Learned a ton. One person I was fortunate to interview was Hadley Wickham from R Studio.

Why should creative people work with data?

Creative people should be working directly with data, because their domain knowledge and creative mindset enables them to look at data and see something from an entirely different perspective than data people. Their creative perspective is what they bring to writing prompts for LLMs like ChatGPT. (I recently had ChatGPT write some advertising-related, tramp stamp tattoos for me.)

For instance, I had a class assignment to use the 2010 Census Data to do a project. It’s a LOT of data (income, number of children, religion, whether you own a gun or not.) I proposed a project, “Which Religion Is Most Likely to Shoot You.

How will the “creative” perspective help get more value out of data?

Data is really just specific, recorded observations about the world. Think about Jerry Seinfeld’s comedy, it’s specific information about the world. He looks at information and thinks “You ever notice…“. It’s not unlike comedy improv. Instead of asking the audience for suggestions (“name something in your kitchen“, “name a profession“) you’re asking data to prompt you.

What mindset needs to change for creatives to get into mining data? Right now the data world and the creative world are usually very separated.

The way things are set up now is that there are the data people and the creative people. They don’t like each other very much, because data is so often used to kill their work. If ad creative people were working with data on their own, they could do the opposite – use data to inspire their creative and to SELL it.

Many creative people are intimidated by Data Science. It’s hard. I’m not a great programmer and I’ve been at it a long time – taught myself to code in Python, R, SQL, Excel (The world’s most popular functional programming language) HTML, CSS, jQuery and some JavaScript. There’s a ton of great MOOCs and YouTube teachers out there – a lot of it free. That wasn’t true when I started learning to code.

The world of Artificial Intelligence has been exploding and getting more complicated all the time. Yet, it’s also getting more automated. A creative person could probably learn enough SQL in a weekend to do real work with it. HuggingFace.co can allow you to write a state-of-the-art Transformers app (Landing Page?) with about 10 lines of Python. There’s also a number of great Low Code/No Code solutions out there.

With Amazon Sagemaker, you can upload massive amounts of data and it will preprocess it, run hundreds of Machine Learning algorithms to determine the best one(s) for your goal, then make it easy to deploy in production.

If you learn about the ever-exploding number of AI capabilities, you can use them to create great advertising with.

You call yourself a “Zombie Data“ Hunter. What is that?

Haha. It’s an idea from the book “Infonomics“ by Douglas B. Laney. The book talks about how companies have extensive financial inventories about their equipment, people, real estate, etc. But often, don’t realize the value of their data or their ability to monetize it.

A lot of data was collected for some other purpose and then just sits “dead“ and unutilized in companies. It can be worth thousands, even millions of dollars. One of my long-term goals is to hunt that data down and find creative ways to bring it to life – to use it to help companies make money. (ZombieDataHunter.com)

For instance, I found 5 years worth of customer comments hidden away on a client’s website. I wrote a Python script to scrape it all off and used an NLP tool (NLTK) to analyze it and turn it into a creative strategy and ads. I’m currently working on a project for an investment company that collected over 200 hours worth of Zoom videos with potential investors during Covid. They were doing nada with it. I’m in the process of transcribing it and mining the text.

Will creatives have to learn math in the future?

Other than some high school level statistics, there‘s not a lot of math in what I do. In NLP, there is a lot of language knowledge – a copywriter’s forte.

The Math does scare people off though. When I talk with ad creatives about mining data,  people tell me you need a PhD in math, but that’s not true at all IMO.

Is ChatGPT a game changer?

Absolutely. It’s incredible for things that are structured. It’s a godsend for an “okay“ coder like myself (along with GitHub CoPilot). I am trying to use pre-trained LLMs like ChatGPT for my comedy algorithm project. ChatGPT can’t write good love letters, because it’s not personal. It’s just doing math over letters. It doesn’t have the shared experiences that we as North American speakers have. But it’s really useful as a writer’s assistant. I think of it like an appliance, like the invention of the microwave – it made made cooking easier and more efficient, but it didn’t stop people from wanting to be great chefs.

The thing I find most human about ChatGPT is that it will give you a wrong answer, but then lie and try to cover up its lie. That is so wonderfully human, haha.

You have a creative agency staffed by robots. What can’t robots do?

Haha. I created a robot agency website as a joke, ShartificialIntelligence.com, about 5 years ago using Python, Flask, and a crude algorithm called Markov Chain Text Generation.  People got mad at me, they‘re scared of AI taking jobs.  And LLMs could take the jobs of some really crappy writers. In the past few years, there has been a small industry of people writing boring copy that is basically like copying somebody else‘s homework. ChatGPT can do that.

What has been the secret to your success?

I agree with therapist and Auschwitz survivor, Victor Frankel. “Success ensues.“ – pursue what you love and success will follow.

Nobody would ever suggest that you go live in your car and write every day as a strategy for success. Some people call me a “data dilettante“ and have been telling me I was goofy for studying this stuff for a long time.

I try to pursue things that I’m interested in and hope I can make money from it. So far, that’s been working for me.

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.

Other Blogs in D3M Labs Series „Contextualizing our world with data

Part 2, Customer Relationship Management: Nurturing the customer relationship with data – an interview with Sarah Carr.

Part 3, Public Relations: On the communication front with the Ukrainian PR army – an interview with Liuka Lobarieva. 

Part 4, Journalism: Solving the experimentation dilemma and growing the New York Times- an interview with Shane Murray.

Related links

The prevelance of AI and the importance of engaging in dialogue – A blog by Varsh Anilkumar

Beyond AI, the realities of operationalizing AI – A podcast interview with Elizabeth Press

Why the public needs to know more about AI – An interview with Varsh Anilkumar

What is the future of AI adoption?

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