Sharp Sports Bettors Reveal What It Takes To Beat The Books


It’s all right there if you believe social media. The cash, the glory, the elevated social status, all within your grasp, tantalizingly so.

All you have to do is be good at sports betting. Make your picks, publicize them to the world, show your winnings, admit your infrequent shortcomings, and vow to bounce back as you keep making those winning picks.

And, oh yeah, not go broke doing it.

It looks easy enough. I was a contributor at Inside Hook for the 2020 NFL season and hit at a 56% clip during the regular season before getting my ass handed to me in the playoffs, “highlighted” by a goose egg in the Super Bowl. I did not have a particular model or algorithm, rarely did deep dives of analytics exploring specific statistical matchups — I often just squared teams up, examined a broad spectrum of themes, and made my plays.

The postseason exposed the shortcomings of my limited decision tree. They also showed the chasm in talent, sweat, luck, and many other additional factors between myself — an average bettor and novice handicapper — and those known as “sharps” in the industry.

While the common folk strive to eclipse that 52.5% winning percentage to break even, the sharps are the ones pushing ever higher, finding the slivers of information that matter when it comes to making picks. Equally important, those pieces of data or gossip can lead to walking away from one play to find a better one elsewhere.

Over two separate panels at BETFEST, Bill Krackomberger, Warren Sharp, Rufus Peabody, and Frank Betti discussed various aspects and angles of the rarified air of being a sports betting “sharp” and all it entails.

You’re going to rack up losses along the way

Krackomberger is decisively old school. He is the guy you want at the steakhouse to regale the youngsters with stories of big wins and near-misses while he drops tidbits of knowledge along the way. A constant presence on the Las Vegas scene, Krackomberger has his own sports betting app — KrackWins  — and noted it was a lengthy process to evolve from what he called being a “square” to being a sharp.

“How did my career evolve? Lots of trial and error,” he said on how he became a sharp. “I didn’t wake up one day and say, ‘I’m going to be a sports bettor.’ It started out with losses. I was a losing gambler for many years before I became a winning gambler and don’t let anyone tell you different, that’s just the way it is.”

Krackomberger also recognized his limitations, which led him to seeking out those who make his service better. He originally reached out to Sharp to help draw him out to Las Vegas. Krackomberger is, in some ways, like the general manager of a sports betting franchise — evaluating talent and finding those who are good at what they do in building a team.

“If it was easy, nobody would work,” he said. “[I] stay close to the real people who live, eat, and breathe this. It’s so difficult to go across the many sports and win throughout the year. I’ve been really successful the past 25-plus years, I surround myself with the best guys in the business.”

Sport-specific focus may be the best play vs. the house

Sharp, who founded Sharp Football Analysis and serves as a consultant for NFL teams, is also self-made. His background in civil engineering included computer modeling, which he incorporated into his pickmaking — making him a pioneer of sorts when it comes to utilizing analytics for sports wagering. Sharp is a household name in sports betting when it comes to the NFL and pointed out there needs to be some grit to help create the glamour.

“People think it’s glamorous to do what we do, but it is a ton of work and very little sleep during the course of the season, but we’re good at it and we love doing it, so it’s definitely worth the effort,” he said. “At the end of the day, we want to have success, but we love it when other people have success with it. We’re selfish, we want to win and make money doing this, but if we can bring on thousands of people to win with us, too, and beat the sportsbooks at our specialty, it’s super rewarding.”

He felt that specializing in one sport provides a sharp an advantage — for the moment — because sportsbook operators are not dedicating like-for-like manpower against those sport-specific bettors. Sportsbooks have teams of oddsmakers that span across all sports to create betting lines versus having one or two people focus on the NFL to neutralize his knowledge base and potential advantage.

“My focus is only on the NFL and there is no chance a sportsbook and their oddsmakers are going to be able to focus as much on the NFL and incorporate advanced analytics into their process of coming up with a line as I am because this is all I focus on,” Sharp said. “This is why we haven’t had a losing year on my totals. We are always going to have the upper hand, in my opinion, there is no chance any bookmaker can put out lines and totals that we’re not going to beat, and I firmly believe that.”

Peabody, who recently teamed with Jack Andrews and Dan Fabrizio to form Unabated, which will launch this summer, struck a similar tone in his betting process, narrowing his focus to counter the ever-evolving market efficiency in the industry.

“I got my start with baseball, did baseball, football, and golf. I stopped doing baseball last year,” he explained. “There’s not enough time. Ten years ago I could do four sports and do them well enough to make good money in all of them. As markets get more efficient, I realized I have to specialize more.

“There’s not enough time in the day to do everything well, and my best work comes when I’m completely consumed with something, and it’s really hard to juggle a lot of sports.”

Models, analytics? Yes. Human intelligence? Also yes.

Just like teams have intangibles that help rate them higher or lower, so do sharps. Krackomberger referred to being able to mix the elements of human intelligence and analysis as “the secret sauce.” As he put it, “Analytics can get you there, but in order to cross that finish line, you have to have that human element, the off-the-field stuff, the late injury, even weather-related.

For Peabody and Sharp, some of that comes in the way of recognizing the limitations of what their statistical models can provide in terms of output. Peabody cited an example from last season that his model overvalued the New Orleans Saints because it did not properly account for their struggles in the deep passing game offensively, and he had to adjust accordingly. Sharp cited his experience as a bettor in knowing when to push some plays harder and when to back off others.

Peabody also made the observation that even machine learning has its shortcomings because it is sometimes too slow to adjust, saying, “If you don’t understand what is driving your output, how do you tell when it’s broken or when there’s something new that it hasn’t encountered and comes along?”

Looking down the road

Scroll through #GamblingTwitter enough, and you will invariably come across stories of bettors who have had their wagers reduced — sometimes substantially — by operators or claims of in-game wagers held up because operators had to approve them, and by the time they were approved, either the limits were reduced, the odds had changed, or it had taken so long the play was moot.

Frank Betti, a professional sports bettor, seized on this antagonism that creates a needless adversarial relationship between operator and sharps he feels needs to be addressed.

“It’s a lack of uniformity of established rules that apply to everybody, a minimum standard of bet limits, how to handle disputes,” Betti said. These things occur with about all of [the operators] that have entered the U.S. market. There’s going to be a time in the not-too-distant future when books from offshore enter the market, and they have a market-maker model that is really only being used in the U.S. by Circa.

“Once that happens, you’re going to see the bigger bettors will be gravitating to the [Bet]Cris, the Pinnacles, the Circas, and then everyone else is left for all the others. The lack of transparency can be solved by just having a set group of rules of what everybody knows what they’re allowed to bet.”

Peabody added that the relentless marketing and advertising by operators also creates a negative effect on those who are trying to become sharps.

“They’re spending all these marketing dollars saying you can win, you can make it big, but what they don’t tell you is that if you actually get good enough to make it big and win, then you can’t do it anymore,” Peabody said. “It feels distinctly un-American in some way. If more people knew that, not even winning bettors, but aspirational sharps, people that aspire to be sharp bettors — if they knew that was what they had to look forward to if they actually succeed, I feel they would be a little pissed off.”

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