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Interview
Bryan Bailey
The Industry Watchdog
by Ian Sherrington
June 2025
Series – The Online Gambling Industry
The Paperwork – Jurisdictions, Legal and Compliance
Bryan Bailey Interview Post Summary
Bryan Bailey, founder of Casinomeister.com, reflects on his journey from an English professor and translator to a pivotal figure in online gambling industry.
Bailey’s transition into the digital realm began in the mid-1990s while teaching at San Diego State University. Fascinated by the burgeoning internet, he taught himself HTML and web design, creating his first websites using Notepad and early versions of Photoshop.
Bailey’s foray into online gambling was serendipitous. While working at a translation firm, he encountered online casinos through clients like World Gaming. After experiencing non-payment for translation services, he recognized the industry’s lack of accountability.
The legendary Casinomeister.com
This realization, coupled with discussions with a reputable San Diego-based casino seeking an online presence, inspired him to create a platform distinguishing trustworthy casinos from dubious ones.
Thus, Casinomeister.com was born in June 1998, aiming to guide players toward reputable operators and warn against rogue entities.
Casinomeister quickly became a cornerstone in the online gambling community, offering resources like the “Rogue Casinos” list and the “Pitch a Bitch” (PAB) complaint resolution service. These tools empowered players to voice grievances and seek redress, fostering a culture of transparency and fairness. Bailey’s efforts earned him industry-wide recognition, including a Lifetime Achievement Award at the iGB Affiliate Awards in 2022.
After 26 years at the helm, Bryan retired in 2024. Bryan’s legacy endures through the standards he set and the community he cultivated, solidifying his role as a seminal figure in the evolution of online gambling.
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Series Introduction
The Online Gambling Industry
A Series of Articles
Ian Sherrington, July 2024
In 1996, a small sportsbook in Austria accepted the world’s first online sports bet: a $50 gamble that Tottenham Hotspur would beat Hereford United in a third round FA Cup replay.
Since then, the rise of the online gaming industry has been meteoric. From humble beginnings, in seedy apartments and dimly lit basements, visionaries and programmers created computer systems that would form the foundations of a remarkable industry.
This transformation has extended gambling opportunities in unprecedented ways. As each new system or service came online, it gained popularity and momentum, leading to rapid growth.
Today, the industry is worth a fortune, with a turnover calculated in the trillions of dollars. It pays significant taxes, contributes to worthy causes, offers investment opportunities, and provides employment to many.
This first article in the series “The Online Gambling Industry” outlines the origins of the industry; looking at the key innovations that contributed to the beginnings of the online gambling industry.
We will explore how these early developments set the stage for the thriving online gambling landscape we see today.
The following articles in this series will delve deeper into the evolution of the industry, revealing the pioneers and their ground-breaking contributions. Join us, as we uncover the fascinating history of online gambling!
A Note from the Author
Dear Reader,
I’m Ian Sherrington and thank you for your interest in this fascinating topic. As a programmer, I played a key role in the early days of the Online Gambling Industry. On January 17th, 1996 the first online sports bet was accepted by the new Intertops website which I had conceived and created. Intertops has been online and accepting bets ever since.
I’ve stayed in the industry and continue to innovate and contribute in various ways, not just technically. During my time I’ve witnessed the evolution of the industry first-hand.
I always wanted to write about the industry and how it came to be and uncover the innovations and the innovators, many of whom I have met, and their invaluable contributions.
Now I have the chance to do it so now I’m investigating .. Who did what, when and.. why?
Huge thanks to Paul and all for your patient editing!
Let the Series begin!
Ian Sherrington, July 2024
