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Juggling Jester is the Fool Monty!

Everyone in Round Table knows all about juggling…that balance between work, family and Table. 


However, for Solihull Tabler Matt Gupwell…juggling IS a way of life, along with stilt walking and unicycle riding as by day he is better known as The Fool Monty Jester. 


The school careers officer would certainly not have approved, which is why it was only in 2009 after a string of dead end jobs that Matt took the plunge. 


“I had more jobs than you could shake a stick at,” said Matt, who learned at 19 that there was good money to be made when he was busking on the streets of Solihull and Birmingham. 


“My parents thought customer service was the way for me and so I had jobs from cabin crew for British Airways to hotel restaurant and reception management to managing entertainment and history at Warwick Castle, which would come in very useful as a jester, to sales jobs. Frankly aside from British Airways, Warwick Castle and restaurants I was pretty rubbish at most of them and ended up being fired more times than a human cannonball! 


“Becoming Monty wasn't so much a decision as a necessity born of 15 years of umm-ing and aah-ing. I'd been sacked from a sales job I hated and had nowhere to go options wise. I had a wife, two young kids and a roof to keep over their heads. 


“We'd gone away to friends for a weekend as I was spiralling into depression and my wife and best friends all sat me down and said ‘now is the time to do what you love as a job, you've got everything to gain and literally nothing to lose’.  


“I'd sold all my juggling and magic kit so had to beg, steal and borrow what I could to start again. 


“That was 2009 precisely one month before the first recession hit. But I secured a contract with Warwick Castle based on my friendship with the Jester I'd employed there in 2004 and her brilliant idea of a Jester double act. 


“At that moment Monty and Jingles the Jesters were launched and I got the best springboard and advertising platform I could have wished for.” 


Over the past five years Gupwell has performed in front of thousands at Warwick Castle and expanded the business to the Jesters Academy – teaching and entertaining kids and adults some of the tricks of the trade. Monty has also become a firm favourite for children’s parties and his tomofoolery and magic is also in demand at weddings! 

And then there is Round Table. 

Having dismissed the notion, based on the usual misconceptions, he was finally persuaded by a persistent Craig Smith to go along to a go-karting night with Solihull Round Table knowing that Matt’s weakness was go-karts. 

“Craig is a good friend and had been sending his daughter to my early morning circus skills club at school for a couple of years.  


“He would mention Round Table to me and I have to admit to thinking it was a bit Masonic, all funny handshakes and regalia so I'd not done anything about it. 


“But Craig knew that another of my hobbies is go-karting with my sons and when the Table night happened to be go-karting he told me I was going along and as it was all for free I couldn't pass up the chance. I went and had a brilliant night and realised that I was wrong about RT so decided to give it a go.” 


After joining Table he was left to arrange his own ‘new boys night’ and it wasn’t that difficult and option! 


“It could only have been a circus skills night. I invited the guys to the school I run my clubs at and we had a couple of hours where I taught most of them to juggle three balls and one of the guys got up to four. I got them walking my not so high wire and trying a variety of wheeled stuff including unicycles. 


“It was great to see them all getting stuck in and I'm now planning a balloon modelling night for this year as a tester for other tables as well.” 


If you fancy a go at any of these…Monty is available. For more information go to or call/text 0770 946 9815 


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