Written by Jörn Peter Thiessen

Casino VIP and player development specialist with 33+ years of land based and online gaming experience, including 2,000+ players personally hosted and 120+ VIP events and roadshows worldwide.

The High Roller Chronicles are based on Jörn's first hand experiences throughout his casino career. Some names and identifying details may be changed to protect privacy.

Methodology · Updated 2026-08-20 · 18+

The VIP Legacy High Roller Chronicles

Chapter 9 — Canada: The Road Trip That Taught Me to Listen. June 13–26, 2005. Thirteen customers across St. George, Montreal, Toronto, Niagara, Vancouver, Creston and Calgary — and why the relationship kept the high roller online.

Chapter 9 – Canada: The Road Trip That Taught Me to Listen

June 13–26, 2005
St. George · Montreal · Toronto · Niagara · Vancouver · Creston · Calgary

Quick links: Chapter 1 — California 2003 · Chapter 2 — Florida & Georgia 2003 · Chapter 3 — African Safari & Cape Town 2004 · Chapter 4 — Florida Car Draw 2004 · Chapter 5 — European Roadshow & MiG-29 2004 · Chapter 6 — Meeting Terrance Watanabe · Chapter 7 — Texas & Oklahoma 2005 · Chapter 8 — Virginia & North Carolina 2005 · Past VIP events · Meet Jörn

By June 2005, our VIP road trips had become about far more than dinners, gifts and meeting high-value players.

Every trip was becoming a live customer research project.

You could sit in an office looking at spreadsheets all day and know exactly how much somebody deposited, what they played and how often they logged in.

But sit opposite that same person over dinner and you discovered something completely different.

You discovered why they played.

You discovered what frustrated them.

You discovered what competitors were doing.

You discovered what they thought about your promotions.

And sometimes you discovered that the only thing keeping a valuable customer with your casino was the relationship they had with you.

Our Canadian road trip from June 13 to June 26, 2005 became one of those trips.

We travelled through St. George, Montreal, Toronto, Niagara, Vancouver, Creston and Calgary, meeting 13 customers along the way.

Looking back more than 20 years later, some of the technology sounds ancient.

Neteller.

Casino software downloaded onto a computer.

Credit-card problems.

Loading screens.

Spinning reels that simply wouldn't stop spinning.

“Packet errors.”

“Time-out errors.”

But the customer lessons?

They haven't aged nearly as much.

Canada Wasn't One Market

One of the first things that became obvious was how dangerous it was to think of Canada as a single market.

In Montreal, we met French-speaking customers who made a very simple point:

Why weren't we communicating with them properly in French?

One customer was a writer and journalist whose wife spoke only French. He knew about our charitable activities but questioned why he wasn't seeing Canadian charities represented.

He also felt strongly that we should be creating French-language promotions.

It sounds obvious today.

But remember, this was 2005.

The industry was still learning that localisation meant much more than changing a currency symbol on a website.

Language mattered.

Culture mattered.

Local causes mattered.

Currency mattered.

And customers wanted to feel that a global online casino understood the country and community they actually lived in.

That lesson would become increasingly important as online gaming expanded internationally.

Sometimes the Customer Shows You What's Wrong With Your Funnel

Another meeting was particularly valuable because the customer was relatively new.

Before joining us, she had researched casino reviews extensively.

The good news?

She thought our support team was excellent.

The bad news?

She thought our registration and purchasing process was far too complicated.

There were too many instructions.

Too many steps.

Too many purchase options.

Credit cards weren't always accepted, yet customers weren't being clearly guided towards alternatives such as Neteller.

Internally, everyone understood the process.

The customer didn't.

That's an important distinction.

Companies often design customer journeys around what makes sense to the people who built them.

Then they wonder why customers abandon the process.

The customer sitting opposite us effectively said:

“You're making it too difficult for me to give you my business.”

Twenty-one years later, companies still make exactly the same mistake.

We Were Learning Things No CRM Could Tell Us

The beauty of meeting customers personally was the extraordinary amount of soft information you learned.

One customer loved elephant sculptures.

Another had a daughter who played golf.

One had a holiday home on Prince Edward Island.

Another suggested that we should organise a Las Vegas golf event for our players.

One customer owned trucking and clothing businesses and was heavily involved in drag racing. His son competed in mud racing.

He arrived to meet us in an enormous 9-litre V8 Ford pickup with nitrous.

You tend to remember the customer when they arrive like that.

Another customer had British roots.

Another regularly visited a land-based casino in Ontario.

Others wanted promotions specifically designed for Canadians rather than seeing American customers apparently winning everything.

Customers wanted to transact in Canadian dollars.

Some wanted money paid directly into their bank accounts.

Others simply wanted somebody to explain the payment process properly.

None of this appeared in a standard deposit report.

But all of it mattered.

Then There Were the Spinning Reels

If there was one phrase that followed us across Canada, it was:

“The reels keep spinning.”

Customer after customer mentioned it.

Games would load endlessly.

Reels would spin for minutes.

Players would be kicked out.

Sessions would time out.

One customer's favourite game repeatedly displayed “loading” before eventually removing her from the casino.

Another experienced the problem virtually every time he played.

To the technology department, perhaps this was a software problem.

To the customer, it was a trust problem.

That difference is enormous.

When someone is playing with real money and a game freezes, the customer doesn't necessarily think:

"There must be some latency between the server and my computer."

They think:

“What just happened to my money?”

And when it happens during a winning session, suspicion grows very quickly.

One Customer Nearly Deleted the Casino

One of the most memorable characters on the trip was a successful businessman with a large family.

He loved the new Keno game.

He clearly had the financial means to be a very valuable customer.

But he had payment problems.

Two cards were registered, but one wasn't working correctly. When he attempted to register it again, the system wouldn't allow him to.

He contacted VIP.

Nobody seemed able to solve it.

Previous answers had already frustrated him.

By the time we met him, he had almost deleted the casino entirely.

Think about that.

Acquisition had done its job.

Marketing had done its job.

The customer liked the product.

He had the ability and desire to play.

And we were potentially going to lose him because nobody could fix a payment problem.

The road trip allowed us to identify it and escalate it.

That experience reinforced something I've believed throughout my career:

A VIP host who cannot solve problems isn't really a VIP host.

Consistency Matters

Another customer raised a completely different problem.

Comps.

She couldn't understand how they were calculated.

One day she might receive a certain amount after a particular level of play.

Another day the relationship between her activity and the comp seemed completely different.

From the customer's perspective, it felt arbitrary.

That is dangerous.

VIP customers don't necessarily expect everything to be identical.

But they do expect things to make sense.

If two similar situations produce completely different treatment and nobody can explain why, trust begins to disappear.

Even worse, she had called support asking what machine she should play and received questionable advice about certain types of games.

It was another reminder that the people speaking directly to customers needed better information, better training and more consistent guidelines.

Customers Were Giving Us Our Marketing Strategy

Another fascinating part of these trips was how many ideas came directly from customers.

Why not have country-specific promotions?

Why couldn't a certain proportion of prizes be allocated to Canadian customers?

Could customers buy into larger slot tournaments?

Could they bring additional guests on a cruise?

Why not organise a Vegas golf event?

Could VIP hosts know which games had been popular or performing well recently?

Why weren't there more Canadian charitable initiatives?

Why weren't promotions available in French?

Why couldn't customers transact more easily in Canadian dollars?

These weren't ideas developed in a boardroom.

They came from conversations.

Some were practical.

Some weren't.

Some would have regulatory or operational complications today.

But that wasn't the point.

The point was that customers were telling us what they wanted.

Our job was to listen.

Then Came Toronto

Towards the end of the trip, I met again with one of our most significant customers.

We had dinner in Toronto.

Afterwards, we walked to the new condominium he was having built in one of the city's most expensive areas.

We met some of his pilot friends and walked through one of Toronto's fashionable neighbourhoods.

The apartments we were looking at started at around $1.8 million.

But the conversation over dinner was much more important than the surroundings.

He was becoming increasingly frustrated with online gaming.

Packet errors.

Time-outs.

Disconnections.

He felt these problems seemed to happen particularly when he was winning, which naturally made him suspicious.

He was seriously considering shifting more of his future gaming back to Las Vegas.

And then he said something that stayed with me.

The Relationship Was Keeping the Customer

He had experienced problems with competitors as well.

The difference, in his mind, was how quickly we responded.

When he raised issues, we came back to him.

When he discussed meaningful rewards with another operator, he felt they took too long and never properly answered him.

We responded.

That mattered.

It wasn't necessarily the software keeping him.

It wasn't the latest bonus.

It wasn't the website.

It was the relationship.

This was 2005.

More than two decades later, I still see companies underestimate this.

High Rollers Don't Necessarily Want More Promotions

Our conversation then moved onto rewards.

And this was where things became particularly interesting.

He wasn't looking for another small promotion.

He wanted a challenge.

Something meaningful.

We discussed the concept of a high-roller slot tournament.

Imagine 50 players buying in for $2,000 each.

That's a $100,000 pool before adding anything else.

He wanted bigger jackpots.

Bigger objectives.

Bigger experiences.

He also wanted recognition for his historical value to the business.

The message was essentially:

“I've been valuable to you for years. Show me that you understand that.”

That is very different from sending another generic weekend promotion.

What Does This Particular Customer Actually Want?

We had previously discussed major tangible rewards, including luxury cars.

But rather than simply repeating what had worked before, we started thinking about his life.

His new condominium would soon be completed.

What about a top-of-the-range sound system?

Something for the new home?

Perhaps artwork, knowing that art was an interest within the household?

The important lesson wasn't whether we ultimately bought a sound system, a painting or something else.

It was the thought process.

Instead of asking:

“What promotion can we give our VIPs?”

Ask:

“What would mean something to this particular person?”

That is one-to-one marketing.

Looking Back, There Were Warning Signs Too

Reading my notes from 2005 today is fascinating because the industry has changed enormously.

There were customers whose personal circumstances should have made us think carefully about how we managed their gaming activity.

There were conversations about significant losses.

There were customers playing with amounts that, viewed through today's responsible-gambling framework, would require much greater scrutiny.

The regulatory environment and our understanding of gambling-related harm are very different today.

And that's important to acknowledge.

Modern VIP management cannot simply recreate the practices of 2005.

The relationship principles remain valuable. The safeguards must be much stronger.

Knowing a customer should never be used simply to encourage them to spend more.

Knowing a customer should also help an organisation recognise when something isn't right.

If you or someone you know needs help with gambling, start with our responsible gambling resources.

Thirteen Customers Taught Us More Than Thousands of Rows of Data

Only 13 customers were personally met during this Canadian road trip.

From a modern acquisition perspective, that sounds tiny.

Thirteen.

Today marketers talk about tens of thousands of clicks, millions of impressions and enormous databases.

But consider what those 13 conversations uncovered.

A difficult registration journey.

Payment friction.

Language problems.

Localisation opportunities.

Currency preferences.

Technical failures.

Inconsistent comps.

Security concerns.

Customer-service problems.

Event ideas.

Golf opportunities.

Promotional ideas.

Product feedback.

Competitor intelligence.

And perhaps most importantly:

Why some customers were staying and why others were considering leaving.

How much would a company pay today for research capable of producing that level of insight?

We got it by sitting down with our customers.

The Waterfall Starts After the First Deposit

Looking back at Canada in 2005 also reinforces something I've written about recently.

The gaming industry has become obsessed with acquisition.

Clicks.

Registrations.

FTDs.

CPA.

But acquisition only gets somebody through the door.

One customer on this trip researched us extensively before registering.

Another nearly left because his payment method didn't work.

Several were frustrated by technical problems.

One significant customer was contemplating abandoning online gaming despite his value to us.

These customers had already been acquired.

The real work started afterwards.

Twenty-one years later, with acquisition costs dramatically higher, that lesson is even more relevant.

The Canada Lesson

When I look back at those two weeks in June 2005, I don't remember the spreadsheets.

I remember the people.

The journalist asking why we weren't speaking properly to French Canadians.

The customer telling us our registration process was too complicated.

The businessman arriving in his outrageous V8 pickup.

The golfer planting the seed for a Vegas golf event.

The customers complaining about endless spinning reels.

The customer questioning inconsistent comps.

And the dinner in Toronto with a high roller openly telling me that one of the biggest reasons he remained with us was the relationship we had built.

Those conversations shaped how I thought about VIP management.

Twenty-one years later, technology can tell us almost everything a customer does.

AI will take that even further.

But there is still one question that technology doesn't always answer very well:

Why?

Why are they frustrated?

Why did they stop playing?

Why do they stay?

Why do they trust you?

What do they actually want?

Sometimes the best way to find out is exactly what we did in Canada in June 2005.

Go and meet them.

Because behind every account number, every deposit, every FTD and every line on a CRM report is a human being.

And if you're prepared to listen, they'll often tell you exactly how to build a better business.