But as part of his bucket list, he decided to fork out the $10,000 fee to enter the World Series of Poker in Las Vegas - and is turning into a superstar.
The World Series of Poker is a series of tournaments held annually in Las Vegas. Sponsored by Caesars Entertainment Corporation, it generally attracts the top professionals.
But after amassing 85 million chips - the second-biggest chip stack - the semi-retired caravan salesman has beaten off competition from more than 7,200 other players to make it through to the final game.
If he beats all the other 26 players, he's set to take home $8 million, and even if he loses he'll net $1 million.
Until now, Mr Hesp's biggest win has been £785 from his local casino, Napoleon's Casino & Restaurant in Hull.
"I am having the most surreal experience of my life," he writes on Facebook.
"It would appear that I've become an international Poker superstar as people from all around the world are wanting to connect with me."
He adds: "This is something I'd quite wanted to do for a while now and when I started just hoped I could make it into the top 1,000."
Quite apart from his extraordinary success, Mr Hesp has become known for his over-the-top outfits, wearing a multi-patterned jacket, bright shirts and a Panama hat.
"This shirt and this jacket and two other shirts, which are back in the hotel being laundered as we speak, were loaned to me by a good friend who lives back home in Bridlington," he tells Poker News.
"I commented on how much I liked his shirts the last time we were here in Vegas and he offered to loan them to me for the trip this time. They so far have brought me very good luck."
There's one other Brit in the final, Jack Sinclair, a 26-year-old online playing professional, who's currently standing eighth in the competition.
The final game will end on Saturday.
Biggest UK lottery winners
Biggest UK lottery winners
Colin and Chris Weir, from Largs in Ayrshire scooped 161 million in the EuroMillions draw after several rollovers in 2011. They are the biggest British lottery winners in history.
Adrian Bayford, who won an astonishing £148m on the Euromillions with his wife Gillian, had to shut up the music shop he owns, because people targeted it with requests for money.
One British ticket won £113,019,926 in October 2010 but decided not to go public.
Car mechanic and racing driver Neil Trotter scooped a staggering £107.9 million jackpot on the Euromillions lottery in March 2014.
Dave and Angela Dawes won £101 million on the EuroMillions in 2011. It was only the third time the couple, from Wisbech, Cambridgeshire, had played the lottery. The couple are said to have since split up.
The sum was won in May 2010 but the winner kept their identity a secret.
One lucky British ticket-holder picked up a £81million EuroMillions rollover but remained anonymous.
Nigel Page and Justine Laycock from Cirencester bagged a £56 million jackpot back in February 2011. On winning the jackpot, Page said: 'I'd already checked my National Lottery account and had seen I'd won £55 on Lotto when I decided to buy two Lucky Dips for the big EuroMillions jackpot on Friday.'
One lucky winner won shy of 50 million but chose to remain anonymous.
Les and Sam Scadding from Newport, South Wales, and a syndicate of seven Liverpudlian call-centre workers shared a staggering £91 million in November 2009. Les, an unemployed mechanic, was £68 overdrawn on the day he bought his ticket, while the Liverpool syndicate only started playing EuroMillions together four months before their win.
Carrington, 22, from Stapleford in Nottingham, banked £45 million after matching all five numbers and two Lucky Stars in a EuroMillions draw in February 2012. The Iceland supervisor said she planned to marry painter fiancee Matt Topham, 22, following the Lucky Dip win.
Husband and wife Gareth and Catherine Bull have fairly modest spending plans despite their £40.6 million jackpot win in January. Speaking about what she planned to do now that she was rich, Catherine explained that she intended to use part of their winnings to replace the carpet on her upstairs landing...
Angela Kelly became one of the biggest lottery winners in UK history back in 2007, after scooping a £35 million EuroMillions jackpot. This is estimated to earn £5,000 a day in interest alone, meaning she's unlikely to ever be short of cash.
In June 2009, 74-year-old Brian Caswell got the surprise of his life when he took his lottery ticket to his local newsagent and discovered he'd won almost £25 million.
Belfast housewife Iris Jeffrey, 58, was the lucky holder of the record 20.1 million rollover lottery winning ticket back in 2004.
Jeffrey, 58, a cancer sufferer, only realised three weeks after the draw took place that she had won the jackpot after organisers Camelot pleaded for the person holding the prize ticket to come forward and claim the prize.
Stephen Smith and his wife Ida from Hemel Hempstead, Herts, won nearly 19 million in the National Lottery. Mr Smith said he would give up his winnings if he could have his health and the chance to live a longer life with his wife.