Football cost Mark Goldberg his fortune but on Saturday the FA Cup will give him a pleasure that is priceless. When his 19-year-old son, Bradley, runs out for Hastings United against Middlesbrough in one of the more lopsided battles in the competition's history, Goldberg Sr will savour a pride that he was never able to feel during a harrowing reign as chairman of Crystal Palace, the club he supported as a boy and which could have ruined him as a man.

"Bradley takes the piss out of me about it all the time," chuckles Mark, sitting with his son in Hastings's modest clubhouse as the pair reflect on how the father recovered from the loss of £40m and how the son's side might survive an FA Cup clash against a team 153 places above them in the football pyramid.

Mark was in his mid-30s when, in 1998, he took the millions he had made from an IT recruitment business and ploughed them into Palace, whereupon every penny disappeared into a demented vortex fuelled by the very worst football economics. He paid Terry Venables £175,000 just to talk about taking the manager's job, then appointed him on a salary worth several multiples of that fee. He was burned by agents and players and a crucial flaw in his initial purchase was that his £22m deal did not include Selhurst Park. After eight months he had to call the liquidators into Palace and he was forced out. His marriage collapsed. He was declared bankrupt.

He started to build a new recruitment business – not as high this time – and also took charge of Bradley's under-nine side, Bromley. In 2005 he was appointed manager of Bromley's senior team in the Ryman League, winning promotion to the Conference South. He is still in charge of Bromley now.

"There's no doubt financially football affected the family for a while but to a certain extent football has helped us get through it all, too," says Goldberg Sr. "Our love for the game has been our escape. After losing my position at Palace and what I had built up over the years, when I watched Bradley play and score in the under-nines, all the other stuff went away. The fact that we've been able to share so much, from the under-nines up, it's safe to say I've had much more fulfilment through football than I've had disappointments, even though I lost £40m through it."

It was a subsequent Palace manager who coined the term bouncebackability but Goldberg personifies it well. "It's really question of not dwelling on [the loss] because if you do, you become ill … I found that I was as happy driving my dad's old family car, which I still drive, as I was in the Porsches and Range Rovers that we used to have. I'm as comfortable in the dugout at Bromley as I was in the boardroom at Palace. I'm as comfortable in a caravan site for a football tournament with the Under 9s as I was in 5-stars hotel in Florida. I feel a lot wealthier because of the loss. I know that sounds really strange but I found out who my friends are and what's important."

Bradley has had to bounce back, too. When he was 16 Charlton Athletic offered him a two-year scholarship. He went to The Valley full of dreams but instead got another reminder that football can turn nightmarish. Charlton released him at 18, explaining to father that his son "wasn't man enough".

"These things happen all the time in football and it just motivates me to prove people wrong," says Bradley, who has been doing just that at Hastings. Before joining them he played a few games for Bromley's senior team but suggestions of nepotism convinced him it would be better to go elsewhere.

Hastings signed him on the recommendation of Steve Lovell, one of the Charlton coaches who saw the player still had potential, and he has justified the faith by scoring 15 goals in 24 games. "Now all the Bromley fans are saying: 'Why the hell is he with Hastings and not at Bromley?'" says Goldberg Sr. "But that's great because they have recognised he's a player in his own right, he's not there just because he's Mark Goldberg's son."

Most of Hastings's young team can tell similar stories, at least insofar as they are playing in the Ryman League after being told at swisher clubs that they could not cut it. Those dents have not broken their ambition and all see the match at Middlesbrough as a chance to show they can make the grade.

Not one of them is under contract, all being paid modest wages or just expenses on a week-to-week basis. They all have other occupations: the forward Zac Attwood sells ice-cream from his mother's sea-front kiosk; Josh Jirbandey is flying to northern California after the Middlesbrough match to start a four-year soccer scholarship; the first-choice goalkeeper Matt Armstrong-Ford supplements his income by working as a naked butler but a knee injury (suffered while playing football rather than while butlering) has forced the club to borrow Liam O'Brien from Barnet.

The chairman, David Ward, says he does intend to give the players some unspecified reward for generating £77,000 by setting up by far the biggest game in the club's history. Before this season the only time Hastings had made it past the FA Cup qualifying rounds was in 2002, when they lost in the first-round proper to Stevenage.

This season Hastings may be toiling in the league – they have won three of 17 matches and drawn their past seven – but they won their first-round tie against Bishop's Stortford and then beat Harrogate in a replay in front of just over 4,000 spectators – 10 times their usual home gate.

They expect to take 1,000 fans to the Riverside, including one who would normally be managing Bromley but would not wish to be anywhere else in the world than Middlesbrough. "If you have kids and enjoy watching them progress at what they do, whatever it is, there is no greater fulfilment," reckons Goldberg Sr.