Reel Lives: Square In The Air’s New Media Director Stewart Darkin On Gaming Entrepreneurs, Longevity, And Beavis & Butt-Head

Brett Smiley

reel lives art

Every gambler has a story to tell. And so does every person who chooses to make a living in this unique industry.

In our “Reel Lives” series, Casino Reports shines a spotlight on people working in the gaming business, from executives, to analysts, to media members, and all points in between.

The subject in this interview: New Media Director Stewart Darkin of Square In The Air, a multi-award winning creative marketing consultancy serving the sports betting and iGaming industries. Stew is a lovely former colleague of the interviewer and a former journalist, who among other things has logged thousands of air miles traveling all over the world to cover the gambling industry expo and conference circuit. Some thoughts on that and more, below!

Stew Darkin

Casino Reports (CR): Where are you from originally and in what city are you based now?

Stewart Darkin (SD): I was born in Harlow, a town just outside of London. I’ve lived all over England but settled in Manchester about 20 years ago. Best city in the world.

CR: What was your first job in the gambling industry?

SD: I joined InterGame in 2012, to edit iNTERGAMINGi magazine. I had zero experience of betting and gaming, and had just three years of journalism experience under my belt. They took a chance on me, for which I’ll always be grateful.

CR: What’s the most clever production solution your team has crafted on location at one of the gaming conferences?

SD: Good question. We filmed a great little video in Times Square with White Hat Studios. The day before, the CEO had noticed a huge Beavis & Butt-Head ad in the square and they had a Beavis & Butt-Head game due for release, so he wondered if we “could do anything with that?” Overnight, we watched webcams from Times Square to understand the ad cycle, so we’d be sure to have it in the background when filming, and the next day, we met the White Hat team there and filmed a promo that would be seen 20,000 times on LinkedIn.

CR: What’s the biggest challenge, in your view, for the industry going forward?

SD: Capturing the knowledge and experience of the first wave of rebels and innovators who set this industry alight 20 years ago — and passing this to the new generation of founders and start-ups. The online betting and gaming industry in particular continues to attract a new wave of entrepreneurs and technocrats, and while that energy and diversification is welcome, there is a reason one product is a hit and another is a flop. Short-term success might simply be a matter of front-end investment and skillful marketing, but longevity comes from a deeper understanding of what makes people tick. I worry that, as the vanguard sell up and move on, the next generation simply doesn’t have the passion for the product.

CR: If you told the 18-year-old version of yourself what you’re doing now professionally, how surprised or unsurprised would that younger version be?

SD: My 18-year-old self would be utterly bewildered. I am old enough to remember when email wasn’t on your phone, in fact it was pretty limited in use at work. Oh, and only the most wealthy had mobile phones back then. Social media? No one knew what that was. We’d barely begun to understand what the internet was and what it would do to the information and communications landscapes. So the notion that I lead a team that makes videos for something called “social media” for clients making millions in online gambling — and it all happens on the “information superhighway” — sounds like the ramblings of a mad man.

CR: How do you like to spend free time away from work? Any interesting hobbies or secret talents?

SD: I like to be outside. I know how dull that sounds, but walking the dog, cycling, or just being in the garden. I really think there’s something good for your soul in being out in the elements, whatever the weather — better still if it is warm and sunny. Any hidden talents are also hidden from me, but I’ll let you know.

CR: What’s the most memorable story you did during your journalism career?

SD: I am not sure I “broke” any big stories — the B2B media doesn’t really appreciate scandalous scoops featuring the big companies that are advertising in your magazine or website. As host of the iGamingFM podcast, we interviewed a gaming executive who’d fled her home in Ukraine the moment the war broke out in February 2022. We spoke to Anna a couple of weeks later, after she’d made her way to the border with Poland and said goodbye to her husband, who returned east to fight for his country. Sobering stuff.

Reel Fast

Artwork by Blundell Design

Another person in gaming who has my utmost admiration is …

Any trailblazer who took a risk and backed themselves when everyone else thought they were bonkers.

If you find me in a casino or on a casino app, the game/bet I’m most likely to be playing/making is …

Compiling an acca (parlay) of safe home-win bets in the Premier League on Bet365, only to see my team let the whole thing down.

Favorite airline?

We fly budget a lot, but KLM always feels like a cut above.

If you close your eyes and picture a casino the first one that comes to mind is …

An online one 😊

True or false: the U.S. version of The Office is better than the U.K. version?


Favorite sports team?

The mighty (but flawed) Tottenham Hotspur FC.

Favorite ice cream flavor? 

I’m a sorbet man, and I like orange.

First vehicle you drove?

First vehicle I drove after passing my test was actually in the U.S. and it was a c1985 Buick LeSabre. How about that?

You can follow Stew on LinkedIn here and the iGamingFM podcast by Stew and the Square in the Air team here on Spotify.

Previous installments of Reel Lives:

Fanatics Betting & Gaming’s Scot McClintic On Building Products, Quantitative Thinking, And Hockey Fights

OpenBet’s Jess Feil On Player Protection, Running An International Team, And Riding Horses

SBC’s Sue Schneider On The Interactive Gaming Council, Mentoring, And The Mississippi River

PrizePicks VP Of Communications Elisa Richardson On Dated Tech Stacks, Sustainability, And Atlantic City