Music Magpie-founding entrepreneur and successful businessman Gleeson, who lives near Bridgnorth but is a lifelong Villa fan from Small Heath in Birmingham, got Telford pulses racing on January 1 when he purchased the remaining unallocated shares of the New Bucks Head club.
Gleeson – whose company Highclear Investments has fronted the investment – has lived in Shropshire for 30 years and is a passionate football fan. He has been a big supporter of local sport, particularly football and has invested in the youth and grassroots game. He is also involved in the University of Wolverhampton's racing team, based in Telford.
His venture into football was not planned. It was somewhat 'off the cuff' – certainly an initial meeting with Bucks chairman Andy Pryce, brother Steve and Ian Dosser – the Telford board members who "hit it off" immediately with Gleeson after a meeting arranged partly by professional football coach Cutler, who also lives in Bridgnorth.
The pull of applying his significant business profile to football was too much to ignore. The 'interesting' element of supporting even a part-time football club from a financial and business acumen perspective was too much to pass up.
Gleeson tells the Shropshire Star: "It just happened, a friend of mine Neil Cutler – who knows Andy – he's the goalkeeping coach at Villa, he said to me the one day 'you want to speak to Andy Pryce at Telford and invest in the club'.
"I thought 'that's an idea, isn't it? I've never done that before'.
"Neil arranged for me to meet with Andy, Steve and Ian and we hit it off straight away, I could see where they wanted to stabilise the club, what they wanted to do with the off-field activities to make sure the club is on sound footing.
"I thought 'I like that, I like people that are sensible about business'. They aren't looking to throw a load of money at the team to get promoted, but then find the club goes bust again.
"That's really quite heartening, when you speak to people like that."
During this 20-minute interview, it was Gleeson's passion for the game and ambition he feels from the Bucks' board that stood out more than anything else.
The millionaire businessman, who saw electronic resale firm Music Magpie floated on the stock exchange for just shy of £210million last year, was quite clear that this investment would be done properly. Conducted like a well-run business. The football club would be secured, sustainable, eventually profitable and successful.
There was no doubting the significance of Saturday's draw against York that secured National League North survival – a sliding doors moment, fans will hope. Gleeson was there at the New Bucks Head, among the boosted gate of 2,621, living every second.
"I was kicking every ball in the stands there, I had to keep moving away from the window because I was convinced I was going to kick the glass in at one point!" Gleeson smiles.
"It would've been, absolutely (a lot harder to achieve targets with relegation) – but that passion would still be there, as has been alluded to, the backroom staff, they really care about the club, from the catering to the trainers, everyone really cares and has a passion and wants the club to do well.
"That came over to me before I got involved, when I came and met the guys at the back end of last year I really bought into that.
"It's all well and good putting some money into a venture, but when the people running it really, really care about it, and have an aim to get the club on to a really steady footing so that nothing happens to it again going forward, that's where I really saw the passion.
"That's why I wanted to get involved, to help the guys deliver that."
Gleeson, who held a board meeting with Bucks chiefs on Tuesday to discuss plans moving forward, revealed a big challenge for the club came in tackling revenue streams.
He adds: "The term is used quite a lot 'sleeping giant' and I think that is very much the thing with the club. Telford's got a big catchment of people that could come and watch really good, competitive football here.
"That's one of my challenges to the board – we need to attract more people. How do we do that?
"What type of promotions can we do? If you get people in and they enjoy it then they'll come back, so it's very much one of the topics around the board table.
"We should be getting capacity gates here but it comes back to performing on the pitch. It was a big step staying up.
"With Paul having a full season ahead, to get with the players, we should hopefully have a better season."
The shareholder said he and his marketing team have ideas to put in place to help bring a bigger footfall through the turnstiles and turn that catchment into booming crowds.
It was only a handful of years ago AFC Telford's future was hanging in the balance. Gleeson admits ensuring finances are secure is a key priority.
"That's exactly it, to make sure the club is stable, generating income to cover the overheads and costs, and then even that it's making some profit," he adds.
"That can then be given to the manager to invest in more players. It's all about getting the basics right first, and then little steps to them go forward.
"Initially I've been trying to understand the mechanics of a football club, it's all new to me, I'm trying to understand that a little bit, the revenue streams, how critical each one is and where the levers are we can pull to develop.
"It's an interesting thing, things you don't usually have to deal with as a business that you have to deal with as a club, it is quite eye-opening, yes, and exciting!
"It's interesting, it's great, stuff I've never done before and I always like doing new things and learning things.
"It's really quite interesting, it's not challenging in any way, because the guys have done such a great job getting it to where it is already.
"It's not like a normal business where you sell widgets and make a profit and that's great, it's down to those 11 players on the pitch delivering a result and you're very much in their hands because you can't do anything about it, you can't get on and they wouldn't want me on the pitch anyway!"