What’s the best way for beginners to get their feet wet betting on college basketball when March Madness rolls around? 105.7 The Fan’s Jeremy Conn recently chatted with PressBox about his tips for beginners, his favorite March Madness betting story and more.
This has been edited for content and clarity.
PressBox: What’s the best way for beginners to get involved with online sports betting before March Madness starts to get comfortable with what they’re doing?
Jeremy Conn: I’m a FanDuel guy, have been forever. I endorse them. But I tell everybody this: I would download all the apps that you can. All you’re doing is getting free stuff initially, and then you decide which ones you like better. If you’re a recreational gambler, you might just pick the site that you’re most comfortable with, that’s easier to navigate, and to me FanDuel is definitely that as opposed to the other sites. I think DraftKings is fairly good, too, if you’re navigating it. Some of the other ones are very convoluted. They should make it easier on the eyes in how to work it and get through it, but with March Madness you want to try to get as many freebies as you can, whether it’s same-game parlays, whether it’s a couple hundred dollars in free bets. It doesn’t matter what site you win it on, you can still cash it out. I’ve been telling everybody I would download everything you can.
PB: How can beginners ease their way into betting on March Madness? Should they stay away from in-play betting?
JC: I remember talking about it when UMBC had their huge upset over Virginia [in 2018]. There were a lot of people going, “Oh, Virginia’s going to come back,” so they wanted to live bet them even though they were down like 18 points, figuring that they were going to come back in the game and pull it out. Live betting basketball can be very difficult because more so than any of the other sports there’s consistent scoring, so you almost have to wait for a timeout or just be all over it and ready to place that bet because there’s a chance you hit “place bet” and then all of a sudden the line changes. And then you hit it again and the line changes. It can be frustrating for basketball, but for other sports like baseball, football or if you’re betting basketball during a timeout, there are some advantageous positions to be in if you think a favorite is going to come back, if you thought they just played poorly in the first half. Some people, instead of live betting will just bet the halves or the quarters. That’s fine, too. In actuality, you’re just looking for an advantage.
PB: Should beginners stay away from parlays? Or are there some simple, fun parlays they can do to increase their potential payout?
JC: The thing I would say is teasers are sucker bets and parlays can be difficult because everyone sees these people winning big money with parlays, so they want to put these 20-bet parlays together now that you can play player props, and they’re very difficult to win. … Things can happen in games that change [outcomes], no matter how easy the line looks. I do like parlays. I like round robins. Round robins will take all of your parlay bets and parlay them together. … That may not be up some other people’s alleys, but I’ve won a lot of money parlaying all my favorite bets together.
PB: There are 32 games throughout the first Thursday and Friday of the NCAA Tournament. How should bettors look at the board without getting overwhelmed?
JC: There are a couple different things I always tell people to look at. Everybody’s going to do brackets, but you always look at the point spreads to see how close [teams are regardless of seeds]. You always have the proverbial 12 over 5. … It can be overwhelming looking at everything. You don’t have to bet the entire board. Find the games you like and then bet those. If you want to parlay games, then you do that. But there’s a lot going on. There are a lot of games to choose from. I would definitely look at the point spreads. Everything’s baked in. These are neutral sites, but remember the underdogs have an advantage because if they start to play well, the crowd usually turns against the favorites and all those other people start rooting for the underdog.
PB: Are there any websites that you use to help you pick games?
JC: I say this all the time — I’m a contrarian when it comes to gambling. That doesn’t mean I’m going to fade everything the public likes, but it does mean I won’t be betting on anything the public is all over most of the time. There are easy ways to get through it, so I like to see where the money is going and fade it. My line of thinking, which some people will laugh at, is the house never loses. They always win. Why wouldn’t I want to be more in line with the house than anywhere else? That’s something that I routinely go to. I look for the reports that are going to tell you where all the money’s going. Consensus reports you can find [on] scoresandodds.com [and] wagerline.com. It’s kind of an easier way to give you an idea where the money’s going. You can always go to different companies that source all this stuff out.
PB: What is your favorite March Madness betting story?
JC: When Virginia won the national championship [in 2019], I had parlayed them in 35 different parlays and I ended up winning over $100,000 just off of that one game. It was crazy because … I just got hot in that first round. I went 16-0 on the first Thursday and then I went 15-1 against the spread the next day, which I’ve never done in the history of my life. I’ll never do it again, I don’t think. It’s so difficult to hit that many bets in one day. That Texas Tech-Virginia [national championship game], it was so ridiculous because I didn’t think Virginia deserved the ball back [late in overtime] after the ball was knocked out of one of the player’s hands and they went to an instant replay. I’m pretty sure I passed out from exhaustion after they won and I didn’t realize how much money I had actually won. It was just crazy.
PB: Have you been in a sportsbook for March Madness?
JC: I have never been in a sportsbook for it. … I’ve seen videos of it. It gets pretty crazy in there. You’ve got people rooting for opposite sides. And now with live betting, it even gets weirder. There are just so many options. But going to a sportsbook, I would tell everybody they should do it at least once for a big-time game or a big-time event.
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