Mark Warburton is fearful other clubs won't take a risk on hiring him due to his past in the city.
The Brentford boss will leave the club at the end of the season and is insisting he is yet to be contacted by any other clubs.
And he admitted that, due to his background, owners may prefer to go down the former player route, which, by and large, is considered the conventional way.
He said: “My personal fear is that people still see me as a risk. I hope I've proved myself as four and a half years is a very long time in football now.
“There are certain skills that you have to transfer. I don't care if you're in charge of 50 builders on a building site you;re managing people.
“If you're in charge of 30 guys on a desk in bank you're managing people and a changing room of players in there is no different to a dealing team in the City.
“So, for me, you look at the transferable skills and then what value you add on top of that. That's the challenge to the players and staff, add value beyond your role and responsibility.
“The fact is there are not that many jobs in football and there are someone really good people. You never wish anyone ill.”
Warburton's Brentford are in the richest competition in football; the Championship play-offs with a prize being a place in the Premier League which is worth over £130million.
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That figure, though, is peanuts to what the Bees boss was used to dealing with.
He added: “I've made hundreds and thousands £130m deals. It wasn’t my money or a club’s money – it was a different game there.
“But you would walk out every night being up 100 grand or down 200 grand. It was a casino-type world, albeit very structured.
“If you ever work in the City it sounds like Monopoly™ money. But my individual turnover every day was between £1.5-2bn. Every day. And there would be 10 guys round a desk doing that.
“It sounds absurd outside, but that is what the financial markets are like. There are maybe not so many players now with all the regulations now but the amounts of money that are transferred are trillions. And that is just the markets.
“What was bizarre was when I was sitting there with the academy budget at Watford and it was being slashed week by week. I was sitting there thinking, I am quibbling over £25 for a set of football cones here. This time two years ago…”
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Warburton has taken players to see the trading floor and his previous life and also used his experiences to address the players.
He said: “I have used that in terms of the players here because I have not got the playing background of a David Weir.
“I use it to show the players that I have been in their situation before. Maybe not out there on the grass but I have been there in terms of dealing with things in that pressured environment. So don’t think I am talking you from a non-experienced perspective.
“This is the richest game in world football and everybody recognises that. I was here last year and it is a fantastic atmosphere. 85,000 people in the national stadium and it is a really huge and passionate game.
“It is great for football and fantastic memories for the players and the staff. But like anything, you have got to earn it and you have got to embrace it and hope you take your chance.”
Warburton earned the trust in the City and hopes to have earned trust in the football world.
He explained: “It is the same as football – you have got to do your apprenticeship. I went in as a clerk the first job we had to do every morning was unlock the telex and the last job you had to do was lock it back up again. The ticker-tape and everything else.
“It was doing the apprenticeship and learning your craft and then building up the trust of your work colleagues and showing you were good enough to do it.
“I was allowed to trade in half-million dollars, then a million dollars, then it was a big day when you were allowed to trade in five-million dollars.
“Trifling sums for the market – huge for these guys here. It was not my personal money but they associate it with your personal money.
“It is the same here. You have to earn their trust and respect. Show that you are good enough. Work hard every day. Be reliable.
“Get here in the morning, because if you were late in the City, you were letting people down. You're taking orders from the far East and if you're not in you can't get it done.”
He added: “At the time, from 1985 to 1999-2000, it was a really competitive environment. If you liked sport and you liked competition, you’d have really loved it.
“It was tin hats on, two phones and it was intense, highs and lows, frustration. But you enjoyed it. The beauty of it was that if you worked hard, you got recompensed.”