He also circumvented the authority of the Lord Chamberlain’s powers in 1958 when he opened the Raymond Revuebar strip club as a private club in the former Doric Ballroom in Soho’s Walker’s Court. He had been unimpressed with the first legal strip club in Soho, believing he could do better. Within two years, Raymond’s Revuebar had 45,000 members. He also bought the freehold of his venue for £14,000 within a year or two, the beginnings of his property portfolio in Soho.

According to Raymond’s biographer, Paul Willetts, Raymond’s Revuebar initially attracted a “chic clientele”, including the actor John Mills and comedian Peter Sellers. The seedy reputation of the club led to regular clashes with the authorities about show content. In 1961, his club was called “filthy, disgusting and beastly” by the chairman of the London Sessions when Raymond was fined £5,000 (then about $12,500) following a magistrate’s decision that permitting members to ring the Ding Dong Girl’s bells constituted running a disorderly house. There was also the issue about an onstage snake charmer who it was ruled should not have swallowed the snake in public.

Raymond first moved into publishing in 1964 when he launched the men’s magazine King, but it ceased publication after two issues. In 1971, he took over the adult title Men Only; his other magazines eventually included Razzle and Mayfair. Among the models featured in his magazines was Fiona Richmond, who became Raymond’s girlfriend. Jean Bradley was married to Raymond from 1951 to 1974, divorcing him over the relationship with Richmond and received a settlement of £250,000; she died in 2002. Richmond denied breaking the marriage in August 2008.

On 22 January 1967, Raymond was initiated into the Grand Order of Water Rats for his contribution to entertainment in the UK.

In 1974, he purchased the lease on the Windmill Cinema and returned it to the original name, the Windmill Theatre, though he relinquished it in 1986. Other theatres controlled by Raymond included the Whitehall Theatre (acquiring its lease in 1968) where the sex comedy Pyjama Tops ran for more than five years along with several sequels, and the Royalty Theatre. When strip tease began to decline, Raymond let his Boulevard Theatre within the Revuebar in 1980 to The Comic Strip team and others pioneering the new “alternative comedy” of the time.

Around 1990 Raymond began to hand over control of his empire to his daughter Debbie (Deborah Jane Raymond, born 28 January 1956), but she died from an accidental heroin overdose on 5 November 1992. Debbie served as the editor-in-chief of the company’s titles, as well as becoming involved in its property concerns.

Raymond diversified, investing millions into buildings and other property, especially in Soho starting in the 1970s, through his company, Soho Estates. During 1977, when many sex shops and strip clubs were closing because the police were active in closing them down, he was able to buy them cheaply. In that year, he was buying one Soho freehold each week, and also acquired property in Chelsea, Kensington and Hampstead. Raymond owned about 400 properties in the Soho area. He was a frequent name on lists of the UK’s wealthy reportedly with an estimated £650 million (at the time about $1.3 billion, in the 2007 Sunday Times Rich List) One associate claimed the estate was worth billions, though public records of assets overseas did not exist. Forbes also placed him on its list of US dollar billionaires.

A recluse in his last years and living in a penthouse near the Ritz Hotel, he died of prostate cancer and respiratory failure in 2008, aged 82. His granddaughters Fawn and India James inherited his estate once estimated at £600 million in The Sunday Times Rich List in 2004. He had been estimated as worth £1.5 billion in 1994, overtaking the Duke of Westminster as Britain’s wealthiest man. Fawn announced her intention to commit to charity work in 2010. Their combined wealth was estimated as £454 million in The Sunday Times Rich List of 2015.