On May 25, Calvin Ayre turns 50 years old. For those of you planning on attending his Seven Deadly Sins party in Dublin during the iGaming Super Show, well, we’re going to miss you. (You can’t say you weren’t warned of the dangers.) To officially kick off the countdown to Ayremageddon, the editorial staff of CalvinAyre.com has compiled a list of 50 noteworthy items regarding the man whose name this site bears. What better place to start than with these ten Moments That Made The Man.
This list is neither definitive nor complete. Only Calvin knows the whole story. (And he’ll likely add his own perspective below after he reads this.) But enough yakking, let’s put the man under the microscope.

Calvin Ayre, Halloween 1968
1. YOUNG CALVIN EMBRACES HIS INNER MONGOL
Calvin has cultivated something of a party boy image over the years, leading many people to assume that hell-raising, skirt-chasing, death-defying and bottle-emptying image represents the sum total of the man. These same people would be surprised to learn that, in his senior year of high school, Calvin was the top student in both science and math. He even won a scholarship for attaining the highest average exam marks in his graduating class. So, him brain good do… good.
Growing up on a farm near Lashburn in northern Saskatchewan (Canada), Calvin’s love of learning was fostered in his elementary school library. It was there that young Calvin first read the name Genghis Khan. Calvin was quite taken with the Mongolian conqueror, seeing past the bloodthirsty reputation and focusing instead on the man’s strategies. The Mongolians moved faster and struck harder than any force in history. Yet despite being all-powerful, they never acted like they had nothing left to learn. Whatever new society Genghis Khan encountered, he studied their knowledge and practices, then incorporated the aspects he found useful into his own bag of tricks. Speed, strength and flexibility… It was a pretty lethal combination in the 13th century and it remains effective to this day. Plus the books had some really cool gory pictures of Mongols chopping people’s heads off.
2. CALVIN MAKES HAY WHILE THE SUN IS SHINING
No matter how much Calvin loved school, he couldn’t believe his luck when his father Ken pulled him out of class in Grade Three to help with the harvest. Back at the farm, Ken hoisted his son up into the cab of a combine (for you city dwellers, that’s like a large tractor with massive rotating blades up front), showed Calvin where the controls were and took him for a test drive. The following morning, it would be Calvin’s turn.
Calvin spent the next two weeks driving up and down the fields, mowing down wheat while his father drove alongside in a truck, collecting the grain shooting out the combine’s funnel. When the harvest was finished, Calvin returned to school, but his learning had never stopped. Calvin had discovered he was capable of vastly more than he realized. Plus he had this newfound urge to ‘borrow’ the keys to the school bus.

Passersby were puzzled when Clark shed the glasses and the fanny pack, ducked into a phone booth, emerging moments later dressed as Superman.
3. CALVIN EXPANDS HIS HORIZONS
When Calvin was 12, Ken sold the farm and moved the family south to Salmon Arm, a town of 10,000 in British Columbia’s picturesque Okanagan Valley. Calvin later confided to his father the move was the best thing Ken could have done. As the eldest son, it would have been natural for Calvin to ultimately take over the family farm. Freed from that possibility, Calvin’s future was now whatever he chose to make it.
The move to a new community also allowed Calvin the opportunity for a total reinvention. As far as his new community was concerned, he was who he said he was, provided he was prepared to back it up. In short order, Calvin impressed his teachers, made a name for himself on the local hockey team and met lots of pretty girls… especially now that he no longer went to school with pig shit all over his boots.
4. DOING DRUGS IN PURSUIT
OF HIGHER EDUCATION
One afternoon, when Calvin was still an adolescent, Ken took him aside, sat him down for a serious father-son talk. Ken told Calvin that it was better to be poor and running your own business than to be rich and working for someone else. Then Ken told Calvin to finish mowing the lawn.
Years later, as Calvin’s freshman year of university came to a close, he had a problem: no money for next year’s tuition. Instead of spending the summer flipping burgers, Calvin took out a small loan, rented a U-haul trailer and stuffed it full of fresh Okanagan Valley apples, cherries and peaches. Then he swallowed half a bottle of his sister’s diet pills and drove 20-hours north to Lashburn in a single go. (He had no choice — it was summer, and the trailer lacked refrigeration.) Before starting out, he’d phoned a few old friends in Lashburn to spread the word, and ended up selling the entire trailer load within a couple hours of his arrival.
These initial interactions with customers – his customers – taught Calvin a lot about running a business; how to convince people to trade their money for his wares. He also noticed how intrigued people were by the story of his Mad Max-style trek north just to bring them fresh fruit. People liked a good story, it seemed. Calvin made multiple runs that summer, earning enough to further his education and – even better – doing so on his own terms, and on his own schedule.
5. CALVIN LAYS SOME CABLE
Years later, after Calvin received his MBA, he got wind of an opportunity to take over a failed office services company occupying two floors of a downtown office tower in Vancouver. This was Calvin’s first real business, with proper accounting, structure, etc. By fate, coincidence or sheer bloody good luck, Calvin’s new office was right across the street from Simon Fraser University, then the only high-speed internet hub in the city. Calvin promptly worked out a deal with the SFU administrators and laid some cable across the street. Just like that, Calvin was now proprietor of the hottest office space in town. Tech companies came flocking, transforming his fledgling office services company into a proper little tech incubator. Over the next few years, Calvin was exposed to all sorts of early internet entrepreneurs. Their successes and/or failures taught him much about what did and didn’t work in the realm of online commerce.
6. CALVIN SEES THE LIGHT
One day in 1994, Calvin was reading a newspaper article about some guy in the Caribbean making a good living by taking sports bets over the phone. The light bulb above Calvin’s head blazed to life. If sports betting worked over the phone, it would probably work even better over the internet. (To be clear, Calvin doesn’t claim to have invented online betting. While he conceived the idea on his own, numerous other entrepreneurs independently arrived at the same conclusion.)
To Calvin, gambling appeared tailor made for the internet, because there was no product to manufacture, warehouse or transport. Gambling’s product was entirely digital; it was eCommerce before that term existed. Plus the world was not going to run out of sports fans/bettors anytime soon. Best of all, the online gambling ‘industry’ didn’t yet exist, meaning opportunities were there for the taking. The gold rush was officially on. Calvin pulled up his trousers, washed his hands and got to work.
7. WHITE LINES, BLACK HATS
When Calvin originally set up shop in Costa Rica, it was as a tech provider. In those early days, the operators were mostly street corner bookies who’d either been chased out of the States or just got tired of snow. Beyond a ‘fuck you’ attitude and a spirit of adventure, Calvin had little in common with these guys. Few, if any, had ever run a proper business like Calvin’s Vancouver tech hub. But because the online gambling industry was so new, there was room for error, and these cowboys made a lot of errors. Perhaps, being business neophytes, they assumed cocaine was a legitimate expense. Perhaps that computer monitor really did deserve to get shot. Perhaps filling a school bus full of hookers for a weekend of nude volleyball and debauchery at your beach house really is how one traditionally marks the end of football season. Who’s to say?
At the risk of stating the obvious, Calvin enjoys a good party. But however liberal Calvin’s own off-hours behavior may have been during those Wild West years, he never let it interfere with his staunchly conservative business approach. This is Calvin’s ‘work hard, play hard’ ethos in action. Many people find this duality hard to reconcile and even harder to duplicate. But it’s the way he rolls. And while his cowboy contemporaries were falling off, Calvin was watching and learning from their mistakes. When it was Calvin’s turn to make his move, he had an advanced degree in how not to run an online gambling company. And a hangover. But only the knowledge stuck around.
8. CALVIN FALLS FOR A REAL BITCH
By the time Calvin was ready to hang out his own shingle, the market had swelled dramatically. There were easily over 1,000 outfits, almost all of them with a name containing the words bet, betting, gambling or sports or combination thereof. Calvin needed something that would cut through the clutter, but he also wanted something more flexible. With a 14-point checklist in hand, Calvin narrowed his choices until a suitable candidate emerged. Bodog was perfect. It was less than six letters, it had optical symmetry (look at it!), you knew how to say it when you saw it and you knew how to spell it when you heard it… Perfect.
But when Calvin ran the name by his team, they hated it. Their primary concern was that it didn’t mean anything. To which Calvin replied, exactly. It was a blank slate onto which he could project whatever he wanted. It was also flexible enough to be attached to non-gambling activities, much in the way Sir Richard Branson’s Virgin brand served as a prefix for everything from soft drinks to airlines. This Dog would hunt, provided they imbued it with the proper attributes.
9. LIFE HANDS CALVIN LEMONS, SO HE REACHES FOR TEQUILA AND SALT
In spring of 2006, Calvin was filming the second season of his Calvin Ayre Wild Card Poker series in Costa Rica. The poker itself had been filmed at a studio in downtown San Jose, leaving only a staged party at the Bodog Compound to get on tape and they could call it a wrap. Everything went smoothly until 75 Costa Rican cops – convinced there was illegal gambling (or something) going on – surrounded the Compound, then charged in, guns drawn. Calvin knew that the cops (and their drug-sniffing dogs) were barking up the wrong palm tree, so he played it cool and waited for the cops to turn red with embarrassment. Which they did… eventually.
Now it just so happened that the 2006 Forbes billionaires’ issue – the one with Calvin on the cover – was set to come out later that same week. Most businessmen would probably have tried to keep a lid on the Compound raid story, lest it unnecessarily tarnish his moment in the sun. And Calvin…?
Calvin is a big fan of the movie Scarface. When the videogame was released, Calvin appeared as himself in a non-playable character role. (First you get the money, then you get the power, then you get the videogame roles.) So the morning after the raid, Calvin went on a media blitz, telling any reporter who’d listen how impressed he was that the Costa Rican police would honor him by restaging the final scenes of Scarface solely for his guests’ enjoyment. News of the raid went around the globe, with each article or program mentioning (a) Calvin’s name, (b) his company’s name, and (c) what services his company offered. The mental image of Calvin’s Compound under siege by a small army of police put a big fat exclamation point on the ‘bad boy’ persona Calvin had been cultivating through Bodog’s marketing campaigns. Even better, the cops had footed the bill.

Drink Hendricks Gin with Calvin at the Seven Deadly Sins party in Dublin, May 25, during the iGaming Super Show
10. CALVIN RETIRES, GETS BORED,
BECOMES MEDIA MOGUL
Following passage of the UIGEA, a nasty encounter with a domain-thieving patent troll and a few more epic hangovers, Calvin found that he’d had enough. He’d spent a decade building Bodog into an industry leader, with little time for much of a life outside work. So he relinquished control of Bodog.com, threw some sacks of money into a Hummer and roared off into the sunset. After about a week, Calvin’s entrepreneurial instincts overrode his urge to play nude shuffleboard with the other retirees, whereupon he set out to turn himself into an online media mogul. And here we are…
So there you have it. Ten moments that made the man. In the coming weeks, we’ll be bringing you other lists spotlighting other aspects of Calvin Ayre’s life and his lasting influence on the world of online gambling. Stay tuned…
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