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It started with him retiring from football at the age of 16 due to injury and stepping away from the game he loved. What followed was a career in the music industry, opening his own children’s venue and a stint working as a tour guide at Stamford Bridge.
Robinson’s love of the game eventually saw him sucked back into football and in 2004 he started coaching Wimbledon’s Under-9s team.
Over the past 17 years he has worked his way up the ranks, until in February he was named head coach.
“Often it all still feels a little bit surreal, but I don’t think that’s a bad thing,” Robinson tells Standard Sport. “You never want to get comfortable and get used to it.
“This club means everything to me. My dad had certain values he instilled in me growing up and this is just a football club that never stops giving really. This club inspires me.”
Wimbledon may inspire Robinson, but his journey should fill people with the belief that anything is possible.
When he ruptured his quad muscle aged 16, Robinson was forced to leave a promising youth career at Fulham behind.
He stepped away from the game, working for the music company The Performing Rights Society and there he eventually progressed to a management role.
But deep down Robinson’s love of football was still there. He did some community coaching with Crystal Palace, while he also managed his work team.
A chance meeting with Tony Wilson, who Robinson played with at Fulham, stoked the fires further when he revealed Wimbledon needed some help coaching their youth sides.
In the end, Robinson took the plunge and quit his job so he could start a business with his wife and coach in his spare time.
“I just packed it all in really, because my passion was for coaching,” he says. “We had just had our two children so we setup a children’s venue. It was kind of like soft play meets Cafe Nero.
“It was a huge risk. We borrowed a substantial amount of money - six figures - to open the business. Most independent businesses go bust in five years, but I’ve always been that person if you want to have a go for something, you go for it.”
The gamble paid off. The venue, It’s a Kid’s Thing, was an award-winning success and Robinson’s coaching was improving, not least because of his creative way to improve his public speaking.
“I actually went and did tour guiding twice a week at Chelsea,” he says. “That was really high pressured as the tour guides there were ridiculously good.
“One was an Elvis impersonator, one was a part-time actor, one was a radio DJ and I was thinking, where do I fit into this?”
Robinson excelled with the Dons academy, taking them on some memorable FA Youth Cup runs, and eventually the top job became his earlier this year as the club fought to stay in League One.
From day one, he wanted to make the players realise this was a new era. Fans came in to paint the training ground blue and yellow, while his values (communication, relentless, ruthless and ownership) were put up on boards by the pitches.
The pitches themselves were changed too, with grids laid out as part of his plans to turn Wimbledon into a high-pressing team.
And then there was, as a nod to Robinson’s past, the introduction of music.
“It’s playing from the morning when the staff get in at eight and it stays on all day,” says Robinson, who asked everyone to pick three songs they liked.
“It brings your environment to life. But also, it’s about making the players and staff realise that everyone is different. If you come visit the training ground, one minute you are listening to rap and the next minute it’s Frank Sinatra.”
Culture is a big thing for Robinson and he has spent time with England rugby head coach Eddie Jones to broaden his horizons.
Robinson doesn’t enforce fines - “if I make someone do something then they are not doing it for the right reasons” - and instead he hammers home the values he believes in.
“All I tried to get across to the lads was, if you think the way you act on the training ground doesn’t impact your performance on the pitch, then you are very much wrong. It erodes trust,” he says.
“Little things like when we have an analysis meeting and some people don’t put their chairs away.
"You might not think that’s having an effect on your team-mates but, I’m sorry, your brain doesn’t work like that.
“He could be your best mate, but there is something in his brain telling him he can’t actually trust you. He can’t rely on you. That translates to the pitch.”
Robinson is clearly right as results on the pitch have transformed under him.
He kept Dons up last year, despite taking over when the team had gone 11 games without a win, and now they are seventh in League One.
He has revamped the coaching staff, looking for marginal gains by appointing a restarts coach and a substitutions coach, and fans at Plough Lane are loving the attacking style of play. “On the ball it is possession based, but we want to play quickly and attacking and exciting,” says Robinson.
“Off the ball we need to be really aggressive and press high, then hopefully that still feels like a Wimbledon side to fans - even though the style of play is different.”
Unsurprisingly, Robinson has blooded players from the academy and in three years he thinks the squad could be 60 to 70 per cent home-grown.
Beyond that Robinson is dreaming big, even bigger than tonight’s game at Arsenal, and he is confident the Dons, who are fan owned, could play in the Championship.
“100 per cent, without a doubt,” he says. “There is nothing more powerful than a group of people all on the same pathway, with the same vision.”
Who knows? When it comes to Robinson anything feels possible.