Back in 2016, when first I set out to tell this story, I quickly encountered a problem: the narrative kept changing at every turn, as the fate of the two startups at the heart of story hung in the balance. Writing a book on events occurring in real time was difficult enough, but there was another challenge: the business of gambling and fantasy sports can be impenetrable to anyone who doesn’t speak the language of overlays, rakes, stacks, fades, and contrarian plays. I thought of what the great Michael Lewis has said: if his mother can’t understand what he’s writing, maybe there’s no point in writing it. To write a book about gambling and fantasy sports that my mother—a Taiwanese artist trained in brush painting—could understand and also want to read might well be impossible, but I tried my best to explain a complex world in a way that might be compelling to anyone. To do that, I had to write a story with rich characters at its center, characters who were also trying to understand this complicated world in which they’d found themselves. The only way would be for those individuals to tell me their stories and, even though they had little to gain from talking to me, they did—much more, in fact, than I expected. I’m blown away, still, at how raw and candid they were about what was, in many cases, a harrowing time in their lives.
This book is the result of more than 100 interviews with those individuals but also many others whose names do not appear in these pages. I’m grateful for the countless hours they spent with me, for all of their insights and their willingness to explain the story underneath the headlines and, yes, the ads.
My agents, Scott Waxman and Jeremy Bell, remained unwavering believers in this project when none of us knew exactly where the story was going to take us. Without Jon Wertheim’s encouragement, this project would not have gotten off the ground. Nathaniel Posey and Ashley Lopez offered wonderful support and advice along the way. I have no idea what this book would be without the guidance of the relentless Will Green, who was instrumental in laying the foundation. Craig Williams read early drafts and offered brilliant thoughts on how to shape the narrative. Jeremy Fuchs was there to track down every last query, until the very last hour. Jill Jaroff made the book dramatically better—and saved me from myself—with her keen eye.
Thank you to Susan Canavan, for her exceptional guidance, enthusiasm, and zeal. I couldn’t have asked for a better editor for my first book. I am also grateful to everyone at Houghton Mifflin Harcourt: Heather Tamarkin, Megan Wilson, Brooke Borneman, Lisa Glover, and Mary Cait Milliff, without whom I’d never have reached the finish line. Cynthia Buck’s perfect touch is on every page.
I had the help of countless others as I grappled with the subject. Scott Gramling and Zach Cohen set me off on the right direction. At various points, Nick Dunham, Charles Chon, Paul Zimmerman, Dan Back, Lee Asher, Stephen Murray, Jonathan Joseph, Art Manteris, Cal Spears, Vic Salerno, Tom Willer, and Robert Walker were invaluable guides through the DFS and gambling jungles. Since October 2015, I relied on the excellent reporting of many terrific writers who have covered the industry, including Michael McCann, Ryan Rodenberg, Dan Barbarisi, Chris Grove, Dustin Gouker, Daniel Roberts, Dan Primack, and David Purdum.
The seeds of this project were planted in the fall of 2014, after I pitched a magazine story on a peculiar little industry to Adam Duerson at Sports Illustrated, and I’ll always be grateful that he said yes. I’m indebted to Chris Stone and Steve Cannella at SI, where I’ve had the pleasure of having spent my entire career working with them and many of the most talented writers and editors in the business. I am also lucky to call them my friends and would not have gotten here without their support: Richard Demak, Gabe Miller, Hank Hersch, Larry Mondi, Stefanie Kaufman, Ryan Hunt, Mark Bechtel, Sarah Kwak, Stanley Kay, Jack Dickey, Trisha Blackmar, Ben Reiter, Marguerite Schropp, Taylor Ballantyne, Prem Kalliat, Chris Chambers, Larry Burke, Ted Keith, Jim Gorant, Emma Span, Scott Price, Mike Rosenberg, Greg Bishop, Tom Verducci, Joe Lemire, Eric Single, Stephanie Apstein, and Gary Gramling. I certainly wouldn’t have been qualified to write this book without Dave Hogue, Jeff Sussman, Mike Merrill, Noah Monick, and the rest of the degenerates from the League of Ordinary Gentlemen, of which I am a three-time champ (alas, over the span of, well, a few decades).
My wonderful friends and family have been my most important source of support: Irene Chen, Ronald Chen, Fiona Griffiths, Steve Yang, Alex Woo, Whitney Friedlander, Kayleen Schaefer, Alex Chung, Greg Kirschling, Julia Chang, Sara Isani, Ryan Martin, Ryan Mauban, Liz Mauban, Lew Gleason, Sandy Chung, Michelle Umali, Tommy Craggs, Marc Pomplun, and Andrew Gurman.
The biggest thank you to Yud-Ren and Jing-Jy Chen, who with their wisdom, grace, and unconditional support have taught and inspired me from the beginning.
Finally, this book is dedicated to Leo Chen, who makes my heart grow each day, and Andrea Woo, who over these last three years put up with way too much, experiencing every high and every miserable low, every step of the way. I don’t know how she makes it all look so easy, only that she makes me the luckiest of all.