Winning, and Losing It All — My Decade In The Betting Industry
By: Adam Chernoff
Tags: Sports, Gambling, Investing, Entrepreneurship, Business

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.

Before football, I was a big hockey fan — as any Canadian kid growing up was.

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.

Cappers Lounge home page. My daily posts were the most popular on the fourm.

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.

An old post of mine on the forum.

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.

My grandmother and I on the day of graduation from grade 12. She passed away a year later.

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.

The vacation rental I found on HomeAway.

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 fit into the island lifestyle quickly.

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.

One of the many corner bookmaking operations in the Domincian Republic

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.

The infamous Danny’s Sports Bar

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.

Me by the odds board in Palms Private Members Club

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.

One of the many Paradise Games locations in The Bahamas

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.

One of my favourite work spots.

My typical setup inside BetCRIS which was formally referred to as Banca Five Star

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.

One of the first nights out with Laura

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.

We loved going out on the catamaran each weekend.

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 first day in Medellin

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.

Lee and Garvin from ASureWin

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.