“Wise men speak because they have something to say; fools because they have to say something” —Plato
His business card says, “Sportsbook Operations Manager” and this 33-year-old youngster has these really crazy ideas about how a sportsbook should operate. He has this notion that a sports betting operator should be transparent in its processes and work to ensure that the player understands these processes. Can you imagine?
And the craziness does not end there.
He thinks a sports betting operator should work to generate ever-increasing play by welcoming all comers, and not going adversarial with the sharp play. He thinks every aspect of the book’s operations should be focused on the player and offer excellent service, always putting in the extra effort to ensure this happens 24 hours a day, 365 days a year.
He also believes players should be educated about betting markets and provided with advice on staying away from lame plays. He also is a myth buster when the 90-day wonders of the betting world start spouting nonsense on social media.
His name is Jeffrey Benson and he has something to say.
Jeff is an old soul, and to paraphrase Mark Twain, he has the calm confidence of a Christian with four aces. He also has the unusual ability to admit when he makes a mistake. How weird.
To be fair to Jeff, he did not come up with all of these off-the-wall ideas on his own. He is surrounded by this curious group of people, many of whom learned the betting business initially in the strangest of ways—by being bettors. This group includes Matthew Metcalf, Christopher Bennett, Drew Mikluscak, Jeff Davis, Nick Bogdanovich, Glen Herzog, and others. The ringleader of it all is Derek Stevens, a man so confused he thought a good business model was to assemble some of the smartest people in betting on the planet, give them the most amazing betting environments on earth, and allow them to do their thing.
Now, it is important to understand they do not know all of the intricacies of betting. They have not yet learned that 25 percent of the players on the offshore market never get their money, and that must be true for I heard it from an iGaming CEO.
Nor do they inform their players when they cannot take five dimes on a bet but will take one grocery dollar and thirty cents ($1.30) of action on the play—a move that is so petty that it should embarrass and shame anyone affiliated with betting.
They also do not try and mislead players on the value propositions contained within bets, which seems to be a thing. Further, they have this funny policy of working to return players’ funds in a frictionless manner. In other words, they are swimming against the tide as to what is going on in the betting space in America.
These guys are so goofy that even Spanky and Captain Jack respect them, and trust me, you will find softer spots in a brickyard than Spanky and Captain Jack.
One of the fascinating things I first discovered about Jeff was that he has “casino eyes.”
Back in the day, when two bosses would discuss things on a casino floor, they would do it side by side, looking in opposite directions. While they were talking, they were surveilling who was in the store, checking for anything that didn’t look right, and just generally monitoring what was going on.
Bill Harrah had amazing casino eyes. The dude should have been a sniper for when I worked for him in the early 1970s, he could spot an employee without a name tag 100 yards away on a crowded casino floor. When Mr. Harrah was in the casino, he was looking at anything and everything.
One of the first non-casino people I noticed with casino eyes was Rod Wright, who was the senator heading the committee that oversaw gambling in the California legislature. I was at a fund-raiser with him in Sacramento and he was tracking everything that moved in the room. I mentioned my observation to him about him having casino eyes and he laughed and added that he always wants to be the first person to notice the money when it walks into the room.
Well, Jeff has casino eyes. When you are in the book with Jeff, he is looking to see it is clean (he bent over to pick up a small piece of paper off of the floor), and that the employees are attentive (he greets the folks behind the counter when he arrives), and that the room is right (he stopped to adjust a sign on the way to the Stadium Swim).
He is also always checking to see what players are in the room, for players like to be recognized, and in a 10-minute interval with him in the front of the book, he waved or said hi to a bunch of folks. Jeff is totally old-school in this sense. And when he isn’t doing all of this, it seems he spends about 80 hours a day on Twitter, answering questions from across the United States, countering the nonsense, and generally having fun.
Jeff is also smart—scary smart. In the betting space today, there are a lot of comical people who have never worked in the space who will tell you how smart they are about betting. Jeff has lived the space and does not bother with such silliness—he just proves it with his words and actions. The fact that he works with some of the smartest betting people on the planet is important, but what is really important is that he learns from them.
Who knows why Jeff is as good as he is, but I would suggest that three things are certainly important. One, he is presently hanging out with a who’s who of betting. There is more betting IQ on both sides of the counter and through their app at Circa than on most continents. Two, Jeff started as a bettor, and that gives him an added perspective by knowing both sides of the counter. Finally, when he decided to go behind the counter, he started as a race ticket writer and did that for 16 months at a local book in Las Vegas. I am sure he was not thrilled with that at the time, but what a person learns writing low-dollar race tickets for 16 months can never be taught.
I think another thing that made Jeff, and his colleagues at Circa become so damn good is that they did not have billions of dollars to piss off while they tried to figure out the business. They knew the business and just set out with a model to grow it organically. I keep waiting for someone in the VC community to figure out a way to take this act to scale in the digital world. The rest of those folks operating in the space would just need to pack up their bags.
I started in the gaming business in the early 1970s, so it is only natural that I see Jeff as a youngster, while he is, in fact, very much an adult. One of my favorite conversations with him was when I asked him what he wanted to do when he grew up.
His answer was immediate. He said he was doing it.
