Cheltenham pro gambler on the dos and don’ts of betting on football. 

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James Mckeown tells Sport and Life about how he’s built a successful career betting on football, why emotions matter as much as stats, how to tell if someone has a gambling problem and why he co-founded social club Ocho in the heart of Cheltenham. 


Watch the full interview with James Mckeown below: 

Hard work not luck 

I know lots of people who make hundreds of bets on football every year. They’ve done it for decades. But they’ve never broken even. Let alone produced a profit. To put it bluntly they don’t seem to have got better at it.

In contrast, Cheltenham’s James Mckeown has made a living from betting on football for more than a decade. But he says there is only one way to get good at gambling – hours and hours of prep.  

“Where it all began, I was really just a typical student, like most guys into football and a friend told me to put on an accumulator,” Mckeown toldSport and Life. 

“I worked out quite early on that I had a knack for it. There’s maybe thousands of variables with with every football match that will affect the outcome.  

“The pitch conditions, what the manager will do with the substitutes, how motivated the players are, whether they’ve been on a bus for six hours to the game or whether they flew there. 

“My coping mechanism is always to work harder. For twelve years I was working sixteen hours a day. There were times when I wouldn’t leave the house for a couple of weeks.” 


Value in obscure football 

James is a Manchester City fan, but doesn’t try and find any value betting on his team. 

He says he realised early on that if you want odds that work for the punter you need to focus on lower profile football. 

“Most people know the Premier League really well. You’ll know Pep plays his tiki-taka. I know football in Bolivia, in Peru, in all these different countries how managers play their football.”


The intangibles 

We live in a world where people love to frame data as the answer to all questions. But Mckeown maintains stats don’t give you the full picture. 

Football is a tribal sport fulled by emotion – emotion that influences fans, players, managers, and crucially, results. 

“There is a lot of intangibles. The mood of the fans is a big part of it. There are so many variables. It could pour down with rain and the pitch is flooded and I’ll bet on a low number of corners because the ball isn’t going to roll as far.”


How not to do it 

Being a successful professional gambler involves adopting lots of positive habits. But what are the don’ts? Above all Mckeown says you shouldn’t chase losses and you shouldn’t judge a bet according to whether it wins or loses. 

“Good bets lose. Bad bets win. I only beat myself up when I missed a bad bet because of maybe impatience or I might be having a bad day, an argument with a friend. All of these things can affect how I perform. 

“It’s very easy to lose a lot of money very quickly. It’s an addictive thing and you’re behind a screen. The best idea is not to start.”


How to spot addiction 

It’s increasingly documented that gambling can be addictive. Like some people enjoy the odd  alcoholic drink, some people can enjoy the odd flutter. But some people can’t stop drinking and some people can’t stop gambling. 

If you’re concerned that someone in your life might have a problem Mckeown believes there’s one big tell. 

“I would say not being honest in terms of your gambling is a big, big read flag. If people are hiding losses, I would say that is number one. 

“Most people don’t like to say they’ve lost. But with gambling it’s impossible not to lose. The odds are against you. I would never advise anyone to start gambling.”


Club Ocho and giving back to Cheltenham

Mckeown’s established himself over years of long days locked away studying football. But in recent years he decided he wanted to get out into the community. 

Hailing from the suburbs of Gloucester and having lived in Cheltenham since coming to the town as a teenage student he also wanted to create something for local people. 

And so off the back of his successful career, he’s funded and overseen the development of Ocho, a members club near Imperial Gardens in Cheltenham. 

“I wanted something high quality that I could contribute to in my town where people could be social, they could network, where they could have fun partaking of really cool events that aren’t provided anywhere else locally.”


Mirari restaurant open to all

Ocho is open to membership applications. But you don’t need to be a member to enjoy a meal at the club’s mediterranean restaurant Mirari. 

“We’ve worked really hard on the quality of the food and the offering in the past few months. We’re in a really good place and props to the Italian chef Simone for the quality of the dishes.” 


This article was written by Teddy Draper, not AI. 

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