Gamble On Podcast #36: PA Sets A Date, Tiger Betting, Interview With Jeopardy Sensation James Holzhauer

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Gamble On, a weekly podcast hosted by US Bets Managing Editor Eric Raskin and Senior Analyst John Brennan, returns with analysis of Pennsylvania’s announced online gaming launch date, the betting on (and media coverage of the betting on) Tiger Woods’ Masters win, and New Jersey’s massive March numbers, plus an interview with reigning Jeopardy champ and pro sports bettor James Holzhauer covering his Daily Double strategy, changing the public image of a sports gambler, and how big a role buzzer skills play in his success.

Transcript of Jeopardy champion James Holzhauer interview

Eric: Until a couple of weeks ago, many Americans didn’t know that sports bettor could be a profession, and for those that did know, the image in their heads of what a professional sports bettor looked like was probably older and more cigar-chomping than the reality.

But James Holzhauer is changing that, quickly becoming America’s most famous pro sports bettor by going on a winning streak on the game show Jeopardy!

He’s already smashed the record for single-day cash winnings, he’s number two all-time in total winnings for a first-time run, and he’s starting to get some serious next-Ken-Jennings buzz. He joins us now on the podcast.

James, welcome to Gamble On.

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James: Hi, thanks for having me.

Eric: Thanks so much for being here. As I alluded to in your intro, you are not what everyone pictures when they think professional gambler. You’re 34 years old, you’re clean-cut, you’re poised, you don’t scream “degenerate.” Obviously this isn’t your chief motivation in going on Jeopardy!, but how important to you is representing the sports betting and gambling community positively and changing people’s opinions of what a professional sports bettor is?

James: Well, the first thing I want to get out of the way is, if you talk to the sportsbook managers here in Vegas they’re going to tell you that I’m not clean-cut. They’ve got a well-paid makeup team at Jeopardy! to make sure I look good on camera [laughs]. That’s not me.

But seriously, I hope I’m representing the industry well. You know I’ve talked to a lot of people, introduced myself and my job, and outside Vegas basically no one has ever heard of anyone with this job — they don’t know what it’s like. There are a lot of people that will ask me follow-up questions about poker, because they’ve heard there are pro poker players, but they’ve never heard of a pro sports bettor.

I’m sure some of them think I run one of those 900 numbers that picks the sure winners, but if I can help the industry at all it makes me happy.

You know, the only other pro gambler I can think of who’s been on Jeopardy! is Alex Jacob, he’s kind of a legend on the show, did really great. He announced himself as a currency trader, so I think a lot of casual Jeopardy! fans don’t know that he ever played poker. But if you watch the way he plays, he gambles big just like I do and plays exactly like a pro gambler should. I wonder if there are others of us that could clean up on the show with the same mentality.

Eric: Yeah, you and Alex both are proving that there is some crossover in the excelling at gambling and excelling on trivia game shows.

John: James, one of the things I want to ask you is that I always find it difficult to explain to people, once you cover a professional sports team for a living as I used to do, your fandom is inevitably going to go out the window.

You know, I used to cover the New Jersey Nets, for example. I got to know and to like some of these players pretty well, I mean given all the time we spend traveling to the same cities around the country for six months and seeing them as often as my family for that stretch. But I was always struck by my utter lack of empathy for them as we would talk after an absolutely gut-wrenching loss — for them. And I wonder if being a pro sports bettor changed how you watch sports as well, even with games you don’t have money on. Do you have a team or a sport that kind of remains untarnished, that you’ve kept out of the options?

James: So I think, ever since I’ve started gambling — although, it really is almost half a life ago now, so I can barely remember what it used to be like — but I watch games now and even if I have no money on them, I get upset when the coaches are not playing to maximize their chances of winning. It’s silly, it’s their exact job and they don’t do it.

You know, I like the Cubs, the Bears, the Knights, but I’ll always bet against my team if I feel like it’s the right move, but sometimes that comes back to bite me.

Back in 2016, when the Cubs got off to that amazing start, the futures market prices on them were so inflated that I shorted them really heavily. I hedged myself out of that position most of the way by the time October and November rolled around. But still, it’s always a great moment to see them finally win one, but it felt a little less good as a fan than it could have.

John: All right, well, so your favorite team is the one you have the money on.

James: I would say, though, that I never handicap soccer, because I think the best pro sports bettors in the world are doing it and I don’t know anything about soccer that they don’t. So the World Cup is always a really exciting thing for me that I can enjoy just as a fan. I don’t even know coaching strategy in soccer so I can’t get mad at the managers either.

I am still sore though about Japan blowing that 2-0 lead last year. My mom’s side of the family comes from Japan, so with the U.S. out, they were who I was pulling for.

Eric: So, getting back to Jeopardy!, the all-in move on the Daily Double is becoming one of your calling cards, and it speaks to both your willingness to gamble and your confidence that you can build your score back up if you happen to zero out.

So two questions: Do you feel that most Jeopardy! contestants aren’t playing optimal strategy with their Daily Double betting? And also, what does it feel like when you have $5,000 or $10,000 built up and you risk it all and get a question that you don’t know the answer to?

James: So for the first question, I worked out what I thought was the optimal strategy for me going in, and I’m playing as close to that as I can. But, you know, I don’t know if that’s the optimal strategy for everyone. They might not feel confident with a certain category that the Daily Double is in or maybe they can’t focus on the trivia question when they have — I’m going to do air quotes here — when they have $10,000 at risk.

You know, I really just think of those as points on the scoreboard until you actually win the game and that goes to your bank account. But, they call them dollars on the show and I think there is a real psychological barrier for some people. And if you don’t think you can answer a question correctly because you are being distracted by that, you shouldn’t be betting that much.

For the second part of the question, there’s already been a game that aired where I had $8,400, I lost it all on the first Daily Double, but I kept my composure. I built up, I think it was $7,200, bet it all on the next Daily Double because I knew that it was the right move, and I came back and won the game. And I really feel like, if you have faith in your analysis, that one single loss should not shake your confidence in yourself.

John: James, playing off that Daily Double strategy, and also the fact that you mentioned you get frustrated when a coach doesn’t make the right decisions, in what ways do you see casual sports bettors leave money on the table?

I don’t know if that frustrates you too, but I imagine you are not a big fan of parlays. Are there other betting mistakes that kind of make you cringe when you see that, either the same bettor makes the same mistakes over and over or such a large pool of players are always making the same mistakes?

James: You know, I think there is a bit of a stigma attached with parlays that doesn’t need to be there. There is nothing inherently wrong mathematically with betting a parlay — unless, of course, you’re the type of person that always hedges the last leg. You know, if you’re going to hedge the last leg of your 10-team parlay, just bet a nine-teamer instead.

But, of course, most people who are betting at the sportsbook aren’t winning players, and no system is ever going to overcome the house edge for them. I would say that much bigger mistakes are people who buy picks from touts, or the type of people who bet a team, and if their team gets out to an early lead, they’ll automatically try to middle in-game. You know, if you really believe that your side is the right one in this at the start of the game, just because they are up 10-0, you shouldn’t have to change sides [inaudible].

Eric: You of course aren’t allowed to go into detail about your future with Jeopardy!, as keeping this interview spoiler-free is part of the deal. You are however, allowed to talk about the future of the sports betting industry, and I’m very curious of your thoughts on that.

Where do you see the state of regulation in a year or two, and, might we see you leave Las Vegas and move to another state anytime soon as more states offer sports betting options?

James: You know, I’m not a legal expert, so I can’t really say a prediction for the direction that is going, but I think they are trending the right way toward more states legalizing. And it makes me happy to see more states legalizing, but you know, I love my home, and even if another state offers the opportunity … I don’t think it would be enough to get me to relocate.

What is making me jealous, though, is seeing some of these crazy promotions in New Jersey sportsbooks where I can’t bet right now, it’s just wild. I know some people that have been able to take advantage of that, you know, good for them.

Eric: Right, well you know, even if Vegas is your home, you did mention other day on the show that some of your winnings might go toward traveling the world with your wife and staying in your 12 favorite cities for a month each. So even if not a permanent relocation, it sounds like some temporary relocation is something that appeals.

I’m curious, do you know what the 12 cities would be?

James: We have kind of a general framework, places we’ve been to already and liked — Kyoto, Barcelona, Rome, the island of Crete we really liked. These are all just kind of a general framework, but the interesting thing about my job is we keep having these conversations about when we should take this trip, and I keep thinking, if all the sportsbooks 86 me, that would be a great excuse to go travel the world for a while. But they never tell you in advance when they are going to do that.

John: James, I want to wrap up with, it’s kind of a lighthearted question, but I just know a lot of listeners to the podcast are thinking it, some I’m going to ask it. I mentioned on last week’s podcast with Eric that, while I have enough aptitude to be at least able to get an audition, with an expired Mensa card in my wallet, no kidding, but I’m certain I’d be defeated by that damn buzzer, though.

I mean, is there an art to that and does it have anything to do with your success?

James: I’m not the best buzzer in the history of the show, that’s definitely Ken Jennings, but it’s a big component of success on the show for sure. I actually bought an e-book by a former Jeopardy! champion before I went on, he has some, he’s done a lot of research with his own practice buzzer on what the best techniques are for how to buzz in the fastest and things like that.

But I really think, you know, every interviewer has asked me, “Oh, how has your betting career prepared you for this job?” and I really think maybe the most important preparation was all those years I spent playing Guitar Hero, mastering the rhythm, pressing the buttons at the exact time.

John: Yeah, I have no rhythm and I think I’m a slow-twitch guy, so the book wouldn’t even help me, but I’m glad it worked for you [laughs].

Eric: Well, John, it’s not too late to start practicing on Guitar Hero, maybe that’s the key.

John: Yeah, that’s not my talent either [laughs].

Eric: Well you mentioned there, James, Ken Jennings is the best ever at the buzzer, but you know, like I said when we introduced you, you are perhaps beginning to close in on him there and I certainly think we all look forward to the possibility of you maybe squaring off against him in a Tournament of Champions, or something like that at some point. And if you do, I plan to place legal pre-game and in-game bets on you [laughs] to beat him if I can.

James: I would be very interested to see where society goes if they are allowing betting on taped TV shows.

John: Well, in New Jersey, of course, you could bet on the Oscars this year, which is the only state to do it, and they are betting in the UK on Game of Thrones, which is amazing to me. That’s crazy, but they do it.

Eric: Yeah, I think for a Jeopardy! Tournament of Champions or something like that to be bet on, it would have to be live or like a poker 30-minute delay or something like that. I don’t think it can be taped weeks in advance to allow legal betting, but, we’ll see.

But thanks so much for coming on the podcast, James, and good luck however much longer this incredible run continues.

James: All right, thank you.

John: Thanks, James.

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