Have you been podcasting longer than Gil Alexander has? Let me go ahead and answer that for you. No, you haven’t. He jumped on the train as soon as it was built.
Gil Alexander has always had a passion for sports betting. As a DJ on pop radio though, there weren’t many places for him to talk about it. In 2005 and 2006, most of his audience was just waiting for him to shut up and hit play on that new Rihanna record.
Knowing radio and not wanting to age out of the business, he started a podcast and immediately saw people were paying attention. It wasn’t many at first, but it was enough for Gil to realize there was a future in talking about gambling.
Now, nearly 20 years later, Gil Alexander is a centerpiece of VSiN’s syndicated lineup. His show A Numbers Game is heard all over the country.
In our conversation for the Meet the Bettors series presented by Point to Point Marketing, Gil offers a lot of opinions on the numbers and how people use them. He shares thoughts on who his show is for, golf’s gambling future, and the people that hate analytics.
Demetri Ravanos I was doing a rock radio morning show at the time podcasting became a thing – 2005 or 06. I feel like the idea of podcasting got sold to us as, “oh, this is just people playing radio.” I wonder if having such a specific focus, something you absolutely could not find on radio at that time, got you to look past or ignore the way it was kind of being painted within the industry.
Gil Alexander That’s an interesting point, and one that I had not considered. That might be very true. Sports betting was such a specific thing, and my wildly innovative idea, I said I was actually going to be honest about winning and losing. At the time, and maybe to some degree now, but certainly at that time, the industry was overrun with shysters. The only voices were people who never lost and would tell you outlandish things about how they did. So, I was going to do this show where I was going to tell you when I won, when I lost, and why.
Yeah, it’s a great point. I had never really considered that it was the specificity of that topic that led me to be so passionate about podcasting.
DR So you mentioned that being honest about when you won or lost was important to your show. I want to sort of fast forward to today. Now when you are on VSiN, do you approach a topic thinking about talking about your win or loss or do you look at the show as everything you talk about has to relate personally to the listener?
GA: Well, if I’m making a bet for myself, I’m always honest about it, win or lose, right? I explain why I’m making the bets that I’m making, regardless of the sport. Tennis is more data driven. Baseball, I think, is more cerebral, but also data driven. Some of the other sports are quite data driven.
For me, every day that I do a radio show, and I’ve done so for seven years now, in addition to the podcast now, which I still do, I think my goal every day is to say something different from what everybody else is saying. I want to have a different take on something. Not performatively, but if I genuinely do, I take some pride in that. The other thing is I want the listener to recognize that the show might be smarter than most but is not so smart that it isn’t entertaining. That’s the biggest trick to all of this.
DR: I think about this a lot when I listen to your show, really all the programing on VSiN, but yours especially because it is in such a prime time for syndicated shows. You hit on it there that it’s smarter than most, but that doesn’t mean it’s not entertaining. So, who is the target audience that you are talking to? It seems to me that it is built not exclusively for sharps, but certainly educated, experienced gamblers versus something that is a little more entertainment driven.
GA: Yeah, it’s one of those answers where as it’s coming out of my mouth, I worry about sounding like a little bit of a jackass, but I would I hope that A Numbers Game is one of these things that I think is very scarce. It has the ability to talk to sharp bettors, has them recognize that they can get something out of it while also talking to the most novice better and those folks recognizing that they can get something out of it. I think that is a very small subset of people. I can give you a couple names. Drew Dinsick does it very well, Adam Chernoff does it very well.
To the extent that I’m able to do it well, I think I’ve achieved my goals on a daily basis.
A radio programmer would be like, “well, that’s terrible, because you don’t even have a target audience. You’re all over the place.” I don’t really subscribe to that theory. It’s kind of more authentic to me, and so far, so good. It hasn’t tripped me up yet. Maybe one day it will.
DR: So, for somebody that has been creating this kind of content in audio form for so long, what would you tell the people just now getting into it, especially in states where betting has just become legal about maintaining an audience? I would imagine that given America’s love of football, there is a crazy fluctuation in the amount of people that are listening in between, say, August and February versus the rest of the year.
GA: The biggest thing I would say is sports bettors are smart. Authentic sports, they can sniff out very quickly if you are not one of them. The biggest thing about that is are you actually betting. If you’re not, I would probably say that you’re probably not doing it right or you’re probably not the ideal person. If you are betting, you are, without even trying, going to become so passionate about what it is that you’re doing. For the person starting out in this kind of content creation, that’s the quickest hack to it all – you’re actually doing this.
You’d be surprised or maybe wouldn’t be, at how many people in the space probably don’t do this. Right off the top, that’s probably not a good start.
I think, by the way, that applies beyond betting. I think that applies to anything that one does. If someone asked me to do a podcast on opera, I would be a horrible choice, right? I don’t go to the opera.
DR: What sport do you think has benefited the most in terms of the expansion of sports betting?
GA: I would say that probably UFC, quite frankly. First of all, that it had its own stage all to itself during the pandemic. I think whether or not there was something in this world called sports betting that, you know, I think people wouldn’t have been as engaged as they otherwise would have been. It came to the fore during the pandemic, but to this day, I know many casual bettors who they’re not watching any of it unless they have a bet on it. If they have a bet on it, they’re absolutely into it.
I’ve said this many times. I think the sport that is most ripe for a betting revolution is golf, which has definitely benefited from legalization to date. But I think it could explode because by the nature of the fact that every tournament is over the span of four days, and it’s a pool of more than 100 players starting on Thursday and obviously past the cut then over the weekend. I think by that nature, there are so many things that one can do betting wise with that sport that you couldn’t do with other sports. This is an old offshore world sports exchange model, but you could create essentially a stock market for players each and every weekend which allows for constant betting.
DR: Well, is there anything at this point that you don’t feel comfortable betting on? Is there a sport where Gil Alexander’s base of knowledge does not include enough of x to place a bet?
GA: Oh, yeah. I think for anybody there is. I mean, your gambling dollar is finite and your ability to be expert in sports is finite. You can’t be an expert on everything.
I think for me, I have a job every day and even though it’s in the same field and I do a podcast on top of that, there’s no possible way. Like right now, for instance, I have double digit bets on the NFL draft, I handicap tennis on a daily basis and just finished the second match that I had a bet on moments ago, and I have a month-long baseball bet. Those are three sports right off the top of my head. So, if someone came to me right now and said, “hey, what do you got on the NBA games tonight or the NHL games?” Like, for me, I can’t even possibly consider the NHL, and I will only bet the NBA if something leaps off the page to me in terms of a daily thing, because you just don’t have the bandwidth for everything.
DR: It’s interesting to me because I have heard old school sports radio guys talk about gambling content very similarly to how old school baseball guys talk about analytics. Like there is this class of people in our business who believe that somebody like you is just trying to boil everything down to a number to give them an answer. And there is no real love of the game still involved for a hard-core bettor. Obviously, that’s not true.
GA: Yeah. One of the things that people who are into analytics, and I consider myself one of them, find most amusing is that people who are not into analytics find an excuse to not have to do any work in analytics. It’s an easier out not to.
It’s a sort of knee jerk reaction of ‘oh well those analytics people don’t watch sports.’ On the contrary, analytics people probably watch more sports than all of them. So, it’s like just because you’re one doesn’t mean you’re not the other. And Aaron Schatz is the creator of DVOA, which is a football analytic that he started at Football Outsiders and now is at FTN, he’s always been amused by that same thing, how those who don’t understand how to sort of make themselves feel better about themselves.
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