In this week's P.O. Box:
Stories from Billy Walters & Spanky
Stream roundup: We’re drafting again
Offszn Book Club: The Devil In The White City…
On my radar: An anniversary
On tap: Best Ball After Dark w/ JJ
I finished the Billy Walters book this week and the biggest thing that stuck with me was his dogged perseverance.
No matter what he was doing—playing pool, selling cars, making sports bets, flipping golf courses—he was going to outwork you regardless of what roadblocks where put in his way.
One of many interesting anecdotes from the book involved the extents he would go for early sports betting edges. Check this out:
I made a deal with the head of the crews who cleaned the passenger planes that landed at McCarran International Airport day and night—at least sixteen hours a day. Why passenger planes? Because each plane was littered with newspapers—and the local sports sections—left behind by travelers. My crew went to the airport multiple times each day to pick up all the newspapers from across the country. They got papers such as The New York Times, The Boston Globe, The Miami Herald, and The Chicago Tribune. Then we had another team of guys who did nothing but read the sports sections of those newspapers to glean any and all information on teams, players, and coaches.
What a hilarious (and smart) hustle.
It got me thinking about what it actually means to be an “edge seeker” or an “advantage player.”
We are all so spoiled with how much good information, resources, and tools we have at our disposal.
This results in there being very little information asymmetry. You might “unearth” an interesting nugget from The Athletic about the Bengals backfield that you want to press in a draft (“Chase Brown is totally gonna be the lead back, bro”), but the entire fantasy world is going to know about it in a couple hours once Rotoworld picks it up.
I think this dynamic has resulted in some disillusionment from fantasy players and sports bettors who feel like they have uncovered an edge simply because they sub to a good site or consume a ton of information.
But when you listen to what the pros are actually doing to seek out edges, it’s clear that there’s a big gap between making a couple +EV bets/picks vs. consistently hunting for info or data no one else has.
On a recent episode of The Risk Takers Podcast—a show I recently discovered and really enjoy—another famed sports bettor, Spanky, shared a story about an odds rundown he was getting via Skype from a bookmaker in a basement in China:
It reminded me of that quote I previously shared from the Shane Parrish book we read, Clear Thinking:
Doing something different means you might underperform, but it also means you might change the game entirely. If you do what everyone else does, you’ll get the same results that everyone else gets.[*] Best practices aren’t always the best. By definition, they’re average.
The truth is that actual edge seeking—like the kinds practiced by Walters and Spanky—requires both ingenuity and an insane work ethic to go where no one else is willing to.
That harsh reality can naturally clash with doing these things as a fun side hobby.
And that’s not to say you still can’t be a “+EV” or profitable player as a hobbyist, but it’s important to understand the doggedness required to maintain an edge for a long time or scale an edge in a meaningful way.
These stories serve as good reminders for myself (and hopefully others) to set realistic expectations for what it takes to consistently win and how much work is required to stay ahead of the curve.
Now if you’ll excuse me, I have my weekly Dragon Boat Racing call with my Chinese pen pal.
☕ Best Ball Breakfast Returns (My First Big Board Drafts). I blindly dive into drafting rookies I've never heard of and talk build strategy, including 3-TE/3-QB and Zero RB. Other topics discussed: Brandon Aiyuk vs. Deebo Samuel culture wars, Trey McGronk szn, pronouncing rookie names, rookie comps, late round targets, and Tank Dell.
📝 Early Big Board Strategy. Speaking of Big Board, I jotted down a few of my early thoughts in a piece for Fantasy Life:
💪 The Swolecast: Best Ball Szn Begins. The one where we debate whether its okay for Davis to wear an NFL jersey while traveling.
☣ Wild Billy Walters Stories & Phil Mickelson Beef. Me and Bric discuss crazy Billy Walters stories from his book, DraftKings removing late swap for NBA, and a continuation of the 2024 best ball meta conversations.
🏆 Fantasy Life roundup. Wrote about the Tee Higgins contract situation and Justin Fields trade rumors.
⏰ Off And On The Clock: Talking Best Ball Strat. Drafted a Big Board team with the Badge Bros and discussed what we think will be the hot topics of conversation throughout best ball summer.
Book #4 for March (20%): The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America by Erik Larson
Already hooked on this book and the weaving of stories around the 1893 World’s Fair between architect Daniel Burnham and serial killer H.H. Holmes. Larson is a killer writer:
It was so easy to disappear, so easy to deny knowledge, so very easy in the smoke and din to mask that something dark had taken root.
Also, this quote from Burnham is about as inspirational as they come:
“Make no little plans; they have no magic to stir men’s blood.”
Book #5 for March (Haven’t Started): Recursion by Blake Crouch
Book #1 (COMPLETE): Clear Thinking: Turning Ordinary Moments into Extraordinary Results by Shane Parris
Book #2 for February (COMPLETE): Chain Gang All-Stars by Nana Kwame Adjei-Brenyah
Book #3 for February (COMPLETE): Gambler Secrets from a Life at Risk by Billy Walters
I noticed that this is my 53rd P.O. Box Newsletter, which means I launched it just over a year ago:
It’s become one of my favorite things to work on each week, so thank you all for reading.
We got one show on tap this weekend for Youtube Members:
🥃 Best Ball After Dark: Interview w/ JJ Zachariason
Need more newslettering? Check out the Fantasy Life newsletter I write regularly:
