Winning, and Losing It All — My Decade In The Betting Industry
I was born and raised in small town Saskatchewan, Canada. If you don’t know, Saskatchewan is a province in the centre of the country. It is cold, dark and outside of Canadian Football season, lifeless. I had a great circle of friends and was active in many sports. My life was very typical of any young teenager and was great, until, at the age of thirteen, my family moved to Calgary, Alberta.
Due to high rent and the cost of living, we had to spend the first three months living with my Aunt and Uncle. He was a successful engineer, and their family had a large home in the upscale Douglasdale neighbourhood. It was the first time in my life that I saw what it was like to have money.
In the small town I grew up in; people drove either a Dodge, Chevy or Ford. I did not know what Range Rover, BMW or Mercedes was. I did not know how to deal with the wealth I saw. I remember making my mom drop me off blocks away from school each morning. Our family car was an old Oldsmobile and was missing its muffler. It made a terrible noise that roared as the car bounced down the street. I was embarrassed for other kids to see me get out of it.
I never was able to fit in.
Living in the big city meant I could no longer participate in many of the sports I did back in Saskatchewan. Our family did not have enough money for me to play hockey and I was still too young to work. My family could not afford to live in the same neighbourhood as my few friends. Distance left me alone many days after school. I spent much of my time at home.
In 2006, Texas Hold ’Em was a new thing on television. A man named Chris Moneymaker just won the World Series of Poker and now everybody wanted to play.
Poker broadcast before and after hockey games in the evening. It was everywhere. I became swept up in the game. I found it fascinating. I created accounts on Paradise Poker, Poker Stars and Titan Poker. I would play freerolls in the evenings almost every day after school. I never won any money, but, the game acted as a gateway into sports betting, which gave me everything I have today.
I do not remember how I found Cappers Lounge, a small online betting forum. The second I clicked on the link, my life changed. Jeff from WunderdogSports owned the forum, and the main contributing poster was Indian Cowboy, who now works for Doc Sports. I created an account on January 21st, 2007 and my life has been dedicated to sports betting ever since.
I knew nothing about point spreads, totals or moneylines. Everything I saw was new. It was a big learning process, but one I accelerated by never stopping. I spent a couple of weeks consuming information night and day.
Like many novice bettors, I fell for a betting system. My poison was martingale and NBA. I bet a team to win the first quarter and doubled up I lost on the same team to win the third quarter. In my mind, this was a fool proof method. I applied this strategy to every big road favourite. I believed these teams were often under priced and presented value. I spent nights backtesting seasons using box scores and spread histories from Covers.
In February of 2007, I started to post my system bets under the name, Rainman900. For better — and for worse, I won several system bets in a row. The spike in clicks and views I received was enormous. My daily posts would get between one and three thousand unique clicks. At the age of fifteen and with just better than a month of betting experience, I was the hottest poster on the forum.
Another forum member messaged me in March. He was a handicapper and wanted to partner with me to sell my bets to paying customers looking for an edge. I never had a job before, and the prospect of making money for nothing was too good to pass up. He handled all the transactions and sold subscriptions at $50 each for the remaining five weeks of the season.
We did extremely well. Just shy of one hundred seventy-five people signed up for a profit of nearly $8,000. The time came to square up the money. I realised at this point that I had no ID. I was still fifteen years old at the time. I did not have any money, so I never needed a bank account. I had no way to receive the $4,000.
My partner came up with the idea of sending the cash via international mail. He purchased a pair of beige golf shorts and put the money inside a birthday card which he tucked into the back pocket. The mail came by the house each day before noon. I planned to skip school the day it was arriving to avoid my parents intercepting the parcel and finding the cash.
My plan went down tragically. Just as the mail truck pulled up to the house, so did my mother, who was stopping back at the house on her way to a meeting. Curious about the package, she opened it on the spot. I thought I got away with it when she unfolded the shorts. At the last second, she put her hand in the back pocket and pulled out a wad of forty US $100 bills. I was busted.
This incident was the first my parents knew of my involvement with sports gambling. They knew I played poker for fun because I would often play freeroll tournaments with my dad and hook the computer up to the television in the living room. There was no harm in playing cards for fun with hopes of outlasting thousands for a minimal gain. Making sports bets for nearly two hundred people per day and receiving a cut for doing so, was a little different.
My mother, still somewhat traumatised by the arrival of the package went to Yahoo Messenger and contacted my partner, quickly putting an end to everything. He took the client list for himself, and I was done with sports betting — for the time being.
In the summer of 2007, I took a summer job at a golf course. I washed and put away members clubs for eight hours a day. As with any golf course, there is always a plenty of action anywhere you look. I was not able to bet sports online, but I bet on anything I wanted at the golf course.
I became obsessed with gambling. Between the summer of 2007 and the spring of 2009, I was betting anything I had on anything I could find. At the age of seventeen, I was in a terrible place. I started to value gambling and drinking more than anything else. My social relationships with friends disappeared, and my grades tanked. I hated everything and dropped out of high school in grade eleven with two months to go.
In a last ditch effort to avoid throwing my life away, my grandmother offered a place in her house with me back in Saskatchewan. The prospect of getting the chance to be back with my friends was too good to pass up. A couple of weeks before the end of summer in 2009, I packed up and left my parents home.
That year with my grandmother will forever be the best year of my life. She was in her mid-eighties but full of gusto. She worked as a nurse at the local hospital for more than four decades and was beloved by every person in town. Living with her was like hitting a reset button on my life. I became active in sports again. I got to spend time with life long friends and remake old ones.
All of the mistakes I made in the two years prior were made right, and I buried it all in my mind. I managed to complete a year and a half of school in one — barely — and squeaked by with grades good enough to walk the stage with my friends and graduate.
In the summer of 2010 after graduation, I took on a job with a local company in town stamping concrete. My job was to either push a wheelbarrow full of wet concrete from the truck to the job site or push a pressure washer around and spray off the non-stick residue from the dried cement. It was miserable, but it allowed me to save up a couple of thousand dollars of “real” money.
The summer ended, and I had no plan. My grandmother’s health was beginning to deteriorate, and I knew she would soon have to leave her home.
Going back to Calgary never crossed my mind. I had nowhere to go. I started searching online for travel options and came across the website, HomeAway. On a whim late one evening, I booked a small condo in the Dominican Republic and a one way plane ticket.
I landed in Punta Cana on September 4th, 2010. I was eighteen years old, did not speak a word of Spanish, and was outside of Canada for the first time in my life. I had just over $2,000 in cash and a couple $100 traveller’s cheques with a month of rent paid in advance. My goal was to see how long I could last.
I was very fortunate to end up where I did. In 2010, Punta Cana was not yet the tourist hot spot it is now. There was a small expat community that lived in the neighbourhood of Los Corales. Without the help of these friends — many of which I stay in touch with to this day — I would have never been able to settle in.
It was not long after arriving that I discovered the huge sports betting industry within the Dominican Republic. The island is home to more than sixteen thousand licensed bookmaking operations. Betting shops are on every corner of every street. When I booked my stay, I did not research this nor did I look into it. Betting was not on my mind.
I quickly learned that these betting shops provide lucrative opportunities. Each one has different branding, but the source of the lines come from just a few large companies such as Banca Real, Juancito Sport, Merengue Sport and Presidente Sport. These companies were very competitive and often were slow to move their prices or over adjusted to offer a better price than the next shop. Not having to deposit funds or wait for withdrawal made betting for a living incredibly easy to do. If I needed money for bills or food, I walked to the corner, placed a bet, and hoped to collect.
My hangout of choice was Danny’s Sports Bar. Danny’s was a popular bar and restaurant on the corner of Los Corales and Cortecito just outside of the famous Playa Turquesa residence. There was a satillite dish, and I could watch any game I bet on while drinking beers for a dollar each. There was also a pool table squeezed in-between the door and the bar. It was the ultimate beach bar.
Daniel Thomas was the owner of the bar. Dan’s brother, Kris, at the time, worked for Amaya, one of the biggest gaming companies in the world. His job was to install wifi which would hook up to their gaming software installed into televisions inside rooms. He would often bring clients to the bar to get away from resort life and experience local culture.
One night in November of 2010, I was inside Danny’s when Kris arrived with a couple of clients. One of the clients was Richard Williams, the owner of CGS International. Unknowingly amidst the packed crowd in the bar for Wednesday Karaoke, I ended up sitting next to Richard at the bar.
He and I chatted for a while before getting into what we did for a living. As fate would have it, Richard was looking to start a sports betting operation inside his two casinos in Trinidad & Tobago. I sold myself as a sports gambler, and he took to me. He left me his information, and after meeting once more, he invited me to fly to Port of Spain and help start his sports betting operation. On December 5th, 2010, I left Punta Cana and travelled to Port of Spain, Trinidad & Tobago.
I immediately started up the operation at Palms Private Members Club in the neighbourhood of Marivale. Sports gambling was not something that existed in Port of Spain or Trinidad. The budget for the operation was limited, and I elected to run things the old fashioned way, by hand, on paper. I displayed betting odds on whiteboards located throughout the gaming floor. If players wanted to bet, they would find me, tell me what they wanted; I would quote odds on the spot and hand write them a receipt.
I did everything I could to make the operation work, but there was just not enough players to make it successful. I lasted just over three months in Port of Spain and left in March of 2011. Little did I know at the time, I would soon return and make an impact greater than I could ever imagine on the island.
For the next couple months, I settled back into betting for a living. I ground out profit and did quite well for myself. One night at Danny’s Sports Bar in September of 2011, I received a text message. The message was from a man named Kevin Knowles a friend of Richard’s. Kevin lived in The Bahamas and owned Paradise Games, a lottery company. He was just launching a sports betting platform on his website and needed someone to run the odds daily. He reached out to Richard for a connection, and he suggested me. At the time, I thought the offer was bogus. But, within two days, I was in Nassau, Bahamas meeting with Kevin and associates.
I was picked up by Kevin at the airport in an armoured vehicle. I knew a few minutes into our relationship that he was a powerful and wealthy man. It was to my surprise when we arrived at our destination, which was a women’s clothing store in the slums of Nassau, just before the bridge crossing over to Paradise Island. We walked to the back of the store and went through a door. Inside was an office, no bigger than 20 feet by 20 feet. This room was where they housed the servers for the website. It was a necessary cover given the crime rates in the city of Nassau. I found it fascinating that a company that brought it so much money ran everything out of a women’s clothing store filled with lingerie and dresses.
Inside this office, I learned the ins and outs of DGS Software. Digital Gaming Solutions is an industry standard for sportsbook software throughout the Caribbean and Central America. Based out of Costa Rica, DGS works hand in hand with DonBest to provide an all in one solution for sportsbook operators. Some of the biggest sportsbooks (BetCRIS, 5Dimes, BetPhoenix, BetUS, Bookmaker, Bovada, MyBookie, The Greek) use this software.
Kevin made me an offer after two days. USD 2,400 a month to set the odds on all American Sports, move them throughout the day, monitor player activity and grade each bet after the games finished. I accepted on the spot, shook hands, left the Bahamas and flew back to my home in Punta Cana.
I was spending $550 of the $2,400 I made each month on a condo to live on one of the nicest beaches in the world. I did my best to spend the other $1,850 on cheap beer. Life was great.
I started in September of 2011. At that time, the operation was lucky to book $10,000 in bets per day. Within September of 2012, I grew the average day to $50,000 in wagers. During football season, we would book between $2,000,000 and $3,000,000 a month.
Every day the popularity compounded. I was extremely confident with the DGS Software and knew the program by heart. I would simultaneously run dozens of markets per game. Our superior offering of wagers allowed us to become the biggest sportsbook in the country within two years.
In February of 2013, I was taking a couple of days off after the conclusion of the football season. I was at a party, and near the end of the night, a blonde girl caught my eye. I went over to speak with her. I introduced myself and did my best to make clear conversation with my alcohol aided thick Canadian accent.
Laura became the first thing more important to me than sports gambling in several years. I was completely infatuated, and luckily for me, the feeling was mutual. We started dating, and everything else in my life became secondary.
In October of 2013, my third football season with the company, I moved with Laura from the Dominican Republic to her home town of Medellin, Colombia. Leaving the island was bitter sweet. Before arriving on the island, my had no direction. Since I came, I built everything and made a name for myself. I was fortunate to get a great job doing what I loved and met a fantastic woman. Leaving all that behind was sad, but I knew my future was with her.
The tourism slogan of Medellin is “Magical Realism”. From the moment I landed in the mountain city of Antioquia, I felt it every second of my time there. There is no way to describe the energy. It is motivating beyond belief.
My wife found work as an elementary school teacher, and I continued to run the daily sportsbook operation for Paradise Games.
In November of 2013, the partners of Paradise Games split. Leander Brice and Garvin Newball left to start ASureWin. Kevin Knowles and Dave Tunnicliffe continued with Paradise Games. Both companies could make a lot of money from lottery operations, but, without me, the sportsbook product would suffer.
I received offers from both sides, the same $2,400 per month, as well as a 5% commission. My work load might have doubled, but my guaranteed salary did too. The 5% fee was a big bonus on top of that.
In the summer of 2014, I had more money in my bank account than I have had before. I decided to ask Laura to marry me. She said yes, and we planned our wedding for the weekend after the Superbowl.
After finishing my fourth football season as an oddsmaker, all of my family and friends came to Colombia to celebrate with us. I saved up all year to pay for our big day. I bought plane tickets for my parents. I booked Brulee, the top rated restaurant in Medellin for our party and all of their service staff for the night. I did not cut any corners.
The day after the wedding, everything changed for me again. I did not have any desire to continue with my job. I had been in Medellin for eighteen months and never been outside of the city. I worked twelve to fourteen hours a day and even more on weekends. Laura worked during the week. Our schedules clashed and the majority of our time together was her watching me watch football.
In the spring of 2015, I left both Paradise Games and ASureWin and walked away from sports betting.
It did not take long for me to begin working on my next idea. Working in Medellin was not an option for me. I knew that I could make far more money doing something on my own in the gambling industry. I just did not know what.
Later in the summer, I flew to Santo Domingo, Dominican Republic to meet with Lee and Garvin from ASureWin. They were looking to expand their business and wanted me to scout a potential acquisition for them. I was paid to go and consult, but, I managed to learn about their lottery operation in the process. The education turned out to be infinitely more valuable than the fee I earned.
I returned to Medellin determined to create a lottery application. I reached out to Richard Williams in Trinidad & Tobago. He heard out my idea and was quick to offer space inside his two casinos.
I found a developer in Medellin and poured all of my savings into the app. By the end of September of 2015, I launched TTPlays inside Jade Monkey Casino in Tobago and Jackpot 7’s Casino in Trinidad.
I call what I built an application, but a more accurate description would be a mobile management platform. The government facilitated the game which we took bets on. They drew four numbers per day ranging from 1–36, just like roulette. Winning bets earned $24 per $1 staked. I saw this as a significant opportunity. My management platform allowed for anyone to book bets on the game and payout at different rates. Inside Jade Monkey and Jackpot 7’s, I offered customers $33 per $1 staked, significantly better than the government.
I rented space in the entrances of casinos and the business exploded.
Within two months, Richard and I were booking more action than we could afford. My advantage was I offered customers physical tickets. Other street lottery operations did not have ticket in ticket out capabilities. Ours acted like a layer of trust between the players and myself. Coupling trust with high payouts, money poured in. It got to the point where we had too much money to move out of the country.
We tried everything. Foreign exchange, shipping containers (not filled with cash, but as a way off the island), Bitcoin – you name it. There was just too much profit and we out grew ourselves.
Technology is my weakness. I can not code, and I struggle to deal with servers. I put confidence in these to the developer. In December of 2015, he betrayed that trust and took my application hostage. He demanded a large sum of money to restore access and hand over the coding. With the future of the company in his hands, I was forced to comply and deal with the circumstances.
I was furious but determined never to have that happen to me again. Instead of hiring out, I hired within my own family and signed on a cousin who worked as a software engineer.
In December of 2015, he was working full time and earning a hefty salary, which I guaranteed each month. My only caveat was that the program had to be running and stay running at all costs.
Business continued to flourish. Each day we grew. I had more money than I could ever imagine. My wife and I moved into one of the best apartments in all of Medellin.
I took numerous trips to different countries with my wife as we relished in the profits of the lottery company. Life for my wife and I became a vacation.
It was silly at times. We went to Peru for four days first class, just to eat. Another time we staked out a spot on a private island in San Andres. I even flew our fathers to come with us on a couple of them too. Money did not matter. Life was grand.
In June of 2016, for reasons beyond my comprehension, my cousin was not happy with our arrangement. He got greedy and demanded more money despite earning a significant salary each month to work from home and not answer to anyone. When I did not comply, he took the site ransom.
This time, I was not as lucky as the first hostile takeover. Out of spite and selfishness, my cousin took everything down and deleted it all. The next morning when customers showed up, I could not book their bets, and I could not verify what their account balance was.
For damage control, the entire operation shut down immediately. I was forced to pay everyone out. The reputation ruined and the opportunity wasted. Everything I had built fell apart in minutes.
Many of the players went to the authorities claiming they had more funds in their account than I was honouring. It was the first time in a year of operating; I had legal issues. My bank account with RBC was frozen.
It was all over. I was devastated.
My cousin cost me my business and cost all of the employees their jobs.
I was left broke.
My wife and I sold everything we owned in Medellin and used that money to fly to Canada, so I could get a job and earn enough money to support the two of us.
In December of 2016, I started working with a large casino operation in Western Canada. I oversee the slot operation and gaming floor at night managing the staff and nearly one thousand machines.
Strangely, working this job has been one of the best things that have ever happened to me. The salary is meagre and fractions of what I was making, but the education value is extremely high. I have learned so much about regulated gaming, policies, procedures and different gaming machines.
I can confidently speak about, disassemble, assemble and repair machines from ten major brands. Managing hundreds of thousands in cash per night, I have grown to understand proper count and budgeting procedures. Every day I go to work and learn something I feel I could have used in the past and can apply in the future. I get better every day and understand more about gaming.
This job has helped me learn about the legalised industry ten fold. Everything I did was illegal in the past. There was a big knowledge void I had in my mind on how things really operate.
Arguably the most significant advantage of the job has been the chance for me to relax and exhale. For the first time in a decade, I am not selling something or depending on a result to live.
I shut down my paid handicapping operation at the end of April. I can be me and interact with everyone else, with no expectation of return. It just feels better.
My life has slowed down considerably, and I could not be happier. I have a sustainable lifestyle with no stress and can provide anything that my family needs. I am not going to say money can’t buy happiness. It bought me A LOT of it. But, at the end of the day to me, I learned to enjoy other things.
I found my passion in writing and producing content. I love sharing my experiences and talking with others about sports betting and gambling. The response in the past year has been tremendous and is extremely motivating.
I have no idea what opportunities the future holds. Whether I pursue a job in regulated gaming long term, or do something on my own, I am not sure. But, time is on my side, and I have a lot of it. For now, I am just enjoying the moment.
