He most probably helps the two get jobs usually just to get them out of his hair: in one episode he send them out into the desert to sell cakes, whilst in another he specially ensures that the Chuckle Brothers remain in a basement room so that they do not damage his priceless china collection that he is moving. His views on the Chuckle Brothers range from benevolent to downright antagonistic - in "Kidnapped", Dan is heard yelling in fury on the phone when his secretary tells him the Chuckle Brothers are there to see him, whilst at the end of the episode he sends the Chuckle Brothers up in a rocket to get rid of them for ever. At the end of "Bringing Home Dan", he chases the brothers furiously after Barry hurts him. In "Do as You are Bid", he makes Paul and Barry stand outside his car window while talking to him, and does not even slow the car down, forcing them to run to keep up with him. In "The Real Dan the Van", he Often however, Dan just tries to avoid the brothers. In "Kidnapped" he instructs his secretaries to tell the Chuckle Brothers that he is unable to speak with them and they should come back in 2 years' time, whilst in "The Real Dan the Van", his replacement explains that Dan rarely goes out in public because he is plagued by two "hooligans" - Paul and Barry.
He also knows Jimmy which probably explains why he is always their manager (in "Steeple Chucks", Jimmy says that he knew Dan ever since Dan was "a trailer"). In Series 13's "Dim Waiters" and Series 18's "Sushi and Sumo", it is revealed that Dan has two nieces named Evadne The Van and Jan The Van. Although they are both in their 30s, Dan also has a gran who isn't that old, which therefore makes his age hard to pinpoint accurately. However, in fact, Dan is the same age as the Chuckle Brothers: in "The Real Dan the Van", Paul and Barry state that Dan went to school with them and was in the same class as them. In "A Change in the Weather", Barry states that he and Paul were invited by Dan to his gran's house for tea, thus suggesting that they were friends, even though in "The Real Dan the Van" he reminds Paul that Dan had a rule never to take Paul's advice.
In "Costa Lotta", Dan tells the Chuckles he has to lie low until the heat dies down meaning he could be a Mafia boss, whilst in the Series 14 episode "Do As You Are Bid", his mumbling could be a parody of how The Godfather speaks. In addition to this, during that scene Italian music plays in the background and one of his partners in business is named Don the Con, a parody of Don Vito . All his employees wear suits and sunglasses, shown in Bringing Home Dan, just like members of the Mafia in a film like the Italian Job. In "The Real Dan the Van", Barry says that in the class photograph Dan is selling exercise books, suggesting Dan is some sort of Mafia businessman. In keeping with The Godfather, everyone is scared of Dan: in "Dim Waiters" Paul, Barry, and Jimmy are terrified of Dan, as he can "get a bit nasty" if he is annoyed. Paul says that the last time he and Barry annoyed Dan, he had them thrown into prison in Mexico, even though they were arrested in England. At the end of the episode, Dan is so angry that he asks "how their Spanish is", suggesting he will jail them all in South America. In "Steeple Chucks", when Paul and Barry ask Dan what he would do if they refuse to follow his orders and blow up a chimney. Dan has them hung upside down in a cellar as a punishment.
He is extremely strong - in "Bringing Home Dan", he takes on 6 police officers and a waiter in one go, and knocks them all to the ground. He has many friends in business like Maxi the Taxi, Rab the Cab, Jeff the Chef, Brie the Tie, Rosie the Posy, Jake the Cake, Reg the Hedge, McDowell the Trowel, Don the Con, Dot the Yacht, and Sam the Pram, his little brother plus many others who all have rhyming first and last names. He employs various assistants, such as his secretary in the episode "Kidnapped" and his chauffeur in "Bringing Home Dan", and he is protected by armed guards in "Steeple Chucks".