How a Briefcase Full of Cash Nearly Destroyed Our Agency

If you think today’s iGaming industry is intense, you should have seen what walked through our doors in 1999. Back when the industry was still finding its feet, we encountered characters that would make a Hollywood screenwriter blush. One client, in particular, taught me the most expensive lesson of my career about who you should never, ever work with.

Let me tell you about Mr. X.

It was a Tuesday morning when my phone rang. No pleasantries, no introduction, just a gravelly voice barking: “You will make my web page and you will start right now!”

I’d handled tons of client calls by then, but nothing like this. When I started asking basic questions like “What’s your budget? What’s the timeline? What’s your casino even called?” he cut me off.

“You know your job and you must just get started and fill in the gaps yourself.”

This should have been red flag number one. But in 1999, iGaming clients were rare, and we were still building our reputation. When he said he’d fly from wherever he was to Cape Town to pay the deposit in cash, I figured it was just an eccentric entrepreneur with deep pockets.

I had no idea what was walking toward my office.

The Entrance That Still Gives Me Chills

A week later, a black Mercedes 500SL pulled up outside our modest Cape Town office. Two men in black suits stepped out, hair slicked back, looking like they’d walked straight out of a mob movie.

My Partner Ashley and I watched from the window, both thinking the same thing: What have we gotten ourselves into?

Mr. X was the larger of the two, built like a bouncer with eyes that seemed to calculate everything in the room. Mr. Y was quieter but somehow more intimidating, the kind of person who didn’t need to speak to command attention.

They walked into our office, and I swear the temperature dropped five degrees. My staff looked like deer in headlights.

“What are you going to show me? Is my website ready?” Mr. X demanded, crushing my hand in a handshake that felt more like a threat.

“But… you haven’t even told me the name of your casino yet,” I stammered.

“You think of the name. You design the site. Just have it ready.”

When I asked about his game provider, payment systems, or any of the basics we needed to build a functioning site, he waved me off. “None of your business. Just make the website.”

That’s when Mr. Y opened his briefcase.

I’ve seen a lot of money in this business, but nothing quite like watching someone dump a pile of cash onto your conference table like we were in a back-alley poker game.

“Now you can start. Will it be ready tomorrow?”

As Mr. Y closed the briefcase, I caught a glimpse of something that made my blood run cold, the outline of a weapon under his blazer. This wasn’t just an unconventional client. This was dangerous.

I tried to explain that quality web development takes time, 2-3 weeks for design, another 2 weeks for coding. In 1999, we were hand-coding everything, crafting each pixel.

“OK, just make it happen ASAP.”

When I asked what kind of business he ran, hoping to understand the brand we were building, his response was ice-cold: “I own private casinos. Mind your own business.”

Fifteen minutes after arriving, they were gone, leaving nothing but the smell of expensive cologne, a pile of cash, and two very shaken web developers.

The 2 AM Wake-Up Call

We worked frantically on their project, trying to create something from nothing. No brand guidelines, no messaging, no clear direction, just the pressure of those cold eyes and the memory of that briefcase.

Two nights later, Ashley’s phone rang at 2 AM.

“WHERE IS MY F**ING WEBSITE? How could you sleep? Get your ass up and go finish my website!”*

Ashley Adir called me in a panic. We were good kids from suburban Cape Town. We’d built websites for banks and legitimate businesses. We’d never been bullied, threatened, or screamed at by clients who treated us like employees in their criminal enterprise.

But we were scared. So we did what scared people do, we worked around the clock to deliver their website as fast as humanly possible, just to get them out of our lives.

The strangest part was when we delivered the site, Mr. X never asked for a single change. No feedback, no revisions, no “thank you.” Radio silence.

We sent the final invoice. No response. We followed up once. Still nothing.

We took the loss and considered it the best money we never earned. Some clients aren’t worth the revenue, or the stress.

The Plot Twist That Taught Me Everything

Two years later, my phone rang again. Same gravelly voice.

“Hello. I need 10 new casino websites ASAP!”

This time, I was ready. I told him exactly what I thought, that he’d never paid his balance, that working with him had been a nightmare, and that my staff deserved better.

“I’ll pay you upfront and you can double your fee.”

To call his bluff, I tripled our rates, thinking that would be the end of it.

The money was in our account that night. Every penny, upfront.

I called him back with new conditions: no contact until the project was finished, and payment terms were non-negotiable.

He agreed.

We delivered 10 casino websites in 4 weeks, working around the clock. It was some of our best work, born from equal parts skill and the desire to never deal with him again.

What I Learned About Character and Cash

Over the following years, I’d spot Mr. X at industry conferences. He always looked out of place among the tech entrepreneurs and legitimate business executives, like a shark swimming in a goldfish bowl.

As the industry matured and regulation took hold, characters like Mr. X were gradually pushed out. The wild west era was ending, replaced by compliance officers, licensing requirements, and legitimate operators who understood that sustainable success comes from building trust, not fear.

Mr. X did well for himself, apparently.  He was the first operator I know to take advantage of Overture, which is Google AdWords today.  He bought players for next to nothing,  something we can only dream of.

But unfortunately, Mr. X suffered a heart attack a few years ago and passed away, leaving behind a reputation that few in the industry mourned.

Looking back, Mr. X taught me more about business than any MBA program could. Here’s what I learned:

Cash isn’t always king. Sometimes the most expensive client is the one who pays upfront. The stress, the sleepless nights, the impact on your team (some money costs more than it’s worth).

Your reputation is built one client at a time. Every project either adds to or detracts from your brand. Working with questionable clients can damage relationships with the legitimate operators you actually want to work with.

Trust your instincts. When someone walks into your office and your gut tells you something’s wrong, listen to it. Red flags exist for a reason.

Set boundaries early. The clients who respect your process and professionalism from day one are the ones worth building long-term relationships with.

It’s okay to fire a client. Sometimes the best business decision is turning down revenue that comes with too much risk or stress.

The Industry That Grew Up

Today’s iGaming industry is unrecognizable from those wild west days. It’s run by public companies, regulated by serious authorities, and built on transparency and compliance. The cowboys and characters have been replaced by CFOs and compliance officers.

And honestly? The industry is better for it.

Don’t get me wrong, I miss some of the Wild West energy, the handshake deals, the colorful personalities who built this industry from nothing. But I don’t miss the sleepless nights, the veiled threats, or the clients who treated vendors like enemies instead of partners.

These days at Vegas Kings, we’re incredibly selective about who we work with. We vet potential clients not just for their ability to pay, but for their professionalism, their vision, and their commitment to building something legitimate and lasting.

We’ve learned that the best clients aren’t just those with the biggest budgets, they’re the ones who respect the creative process, value expertise, and understand that great work comes from collaboration, not intimidation.

Mr. X burned a lasting memory into our souls, but he also taught us one of the most valuable lessons in business: sometimes the best deal is the one you walk away from.

The Real Lesson

If someone walks into your office demanding instant results, paying in suspicious cash, and treating you like hired muscle rather than skilled professionals, run. Run fast, and run far.

Because in the end, the clients who build your reputation aren’t the ones who scare you into working for them, they’re the ones who inspire you to do your best work.

“The Power Play by Moshe Adir” is released weekly on the Vegas Kings website and LinkedIn. Drawing from nearly 30 years of experience in design and development for online gaming, Moshe shares exclusive industry insights, lessons learned, and behind-the-scenes stories from the evolution of iGaming. Stay tuned for fresh perspectives from one of the industry’s OG