Some poker players, like Phil Ivey or Phil Hellmuth, are to be feared and revered. Others, like Taylor Caby, are to be admired and envied. At the ripe young age of 25, he began planning his retirement from the game with millions of dollars in earnings—all of it from poker, but only a portion of it won at the tables. His story is certainly one worth noting.
“Like Everyone Else”
Taylor “Green Plastic” Caby was born in Illinois in 1983. As a boy growing up in a Chicago suburb, he couldn’t wait to turn 14 years old so he could join in the holiday poker games that had become a tradition in his family. In a 2009 interview with BusinessWeek Magazine Caby said, “The first year they let me play they bought me a poker book for Christmas, and I was so excited that I went and read literally every poker book in the library.”
During his high school years, Caby started playing with some friends and they helped each other improve their game. By the time he entered college at the University of Illinois, he was proficient enough to try his hand at playing on the Internet. “A friend of mine, Andrew Wiggins, and I were playing a lot online,” Caby told Chicago Now in 2010. “I think we were like everyone else. Around 2003 poker was really popular, with the World Series boom on TV and everything…. So we began studying with each other and became winning players from there.”
Of course, 2003 was the year Chris Moneymaker became a worldwide celebrity, turning an Internet satellite win into multi-million-dollar victory in the World Series of Poker (WSOP) Main Event. Emulating the champion’s success, Caby deposited $35 on Full Tilt Poker, quickly amassed a sizeable bankroll and soon gained online fame by playing and beating high stakes games. Between 2004 and 2007, he went on a run worth over seven figures.
From Player to Innovator
As news of Caby and Wiggins’ success spread, they were often asked by fellow students for tips on strategy, how to play and win. That’s when the light bulb went on over the undergraduate’s head—the idea of a training website that people could use for poker. The two friends went into a process of development for about a year and were eventually able to launch the web site they called “Cardrunners” in 2005.
“It literally started as a project between me and Andrew, managed in a fraternity room,” Caby explains. They uploaded training videos, contracted with pros to teach lessons, created active poker training forums and marketed the site until it caught the eye of the business mavens at Full Tilt, who had noticed some of the top players on their site were pros for Cardrunners.
“In 2007, we were approached during the World Series by Full Tilt,” says Caby. “They were looking to see if we’d be interested in a partnership so that both sites could promote each other. We thought that was great because we thought it would not only open Cardrunners up to a new audience, but kind of give some of our top pros some recognition.”
How well did the relationship work out? By 2010, Cardrunners had expanded to 52 people working full time out of an office in Chicago. They acquired a few additional sites and grew their library to over 2,000 instructional videos featuring more than 80 professional players. By one estimate, Cardrunners is easily worth $5 million.
Going Beyond Poker
As the web operations became more and more successful, Caby found himself playing poker less and less. He managed to cash at the 2007 and 2010 WSOP but, according to Hendon Mob statistics, his tournament game has never been up to par with his cash game. A $50,000 prize for a seventh place finish at the 2009 Full Tilt Poker Million VIII was his apex.
According to Caby, “At this point (poker) is a job like anything else.” What really motivates the Chicago University graduate with a degree in finance is building businesses. One of his instructors at Cardrunners, Cole South, turned into an excellent source of venture capital, taking stakes in several of Green Plastic’s new enterprises, including the poker analytics software known as “Hold’em Manager” and a fantasy sports site called “DraftDay.”
Since Black Friday shut the door on most Americans playing poker online in April 2011, Caby has slowed his pace a bit. He enjoys playing basketball and learning racquetball when he isn’t managing his online businesses. He’s also joined DeucesCracked founder Jay Rosenkrantz as an executive producer of a documentary film project called “BOOM!”—a retrospective of the poker boom of the past decade. It should be out well before his 30th birthday.