They are in their 50s, have been in investment banking for more than a generation and, with plenty of cash in the bank, are seeking new challenges.

Some of Europe’s most senior dealmakers such as Simon Robey, Yoel Zaoui and Carlo Calabria are using their decades-long experience to reinvent themselves outside the investment banks in which they built their careers. Leaving behind an investing banking sector hobbled by heightened bureaucracy, pay cuts and regulatory scrutiny, they will join an existing group of independent advisers.

Dealmakers such as Simon Robertson and Mr Zaoui’s brother Michael in Europe and Michael Klein in the US use their highly prized Rolodex for their own ventures – often armed with no more than a small office and a secretary.

“It’s an option for senior bankers who’ve left the Street already to continue to advise their long standing clients while staying on the periphery,” says Joseph Leung, founder of executive search group Aubreck Leung.

But the question is whether such one-man-shows can prevail amid a shrinking M&A deal market and intensifying competition between investment banks and fast-growing boutique advisers alike.

The latest banker to set up what one seasoned dealmaker calls “advisory kiosks” is Simon Robey. After spending almost half of his life working for Morgan Stanley, the 52-year-old recently announced he was to step down as co-chairman of global M&A in January next year.

Mr Robey’s plan is to set up on his own an independent “small and discreet” advisory venture, which is likely to be fewer than 10 people, according to people close to the situation.

Morgan Stanley has arranged for Mr Robey to continue advising key clients, including those still embroiled in dealmaking such as oil group BP. After January 2013, if Morgan Stanley clients want Mr Robey to continue to advise them, he would be able to even though he would be independent of the bank, said a person with knowledge of the plans.

Similarly, Yoel Zaoui gave up his position as co-head of global M&A at Goldman Sachs earlier this year with the aim of finding a new venture. Mr Zaoui, who was touted as possible chief executive for French conglomerate Vivendi, is considering his various options which could include setting up in partnership with his brother Michael, who after a career at Morgan Stanley has already been acting as independent adviser in recent years to companies such as GDF.

William Vereker, one of the City’s most respected natural resources M&A bankers who last month stepped down as Nomura’s global co-head of investment banking and into a vice-chairman role, is believed to be considering a similar move as one option among several.

Bankers and recruitment experts say that people such as Mr Robey and the Zaoui brothers are among a handful of European dealmakers who have the skillset, experience and depth of relationships to set up on their own.

“You have to be an absolute go-to banker to be able to do this,” one senior City headhunter says.

“If a FTSE 100 chief executive wants to talk about a large deal he will always call the same handful of bankers: people like Simon Robey, Karen Cook [at Goldman Sachs] and James Leigh-Pemberton [at Credit Suisse],” he adds.

Unlike a number of dealmaking stars in the US such as Ken Moelis, Roger Altman or Robert Greenhill, their European peers mostly have no desire to build global boutique advisory firms with hundreds of employees – a task that would also be harder to achieve amid Europe’s scattered markets.

Bankers say the move into freelance advisory has its roots in a generational shift as much as the aspiration for a higher level of freedom, but also a deep-rooted disenchantment over the diminishing sway of M&A advisers at large banks.

Advisory and underwriting revenues at the 10 largest investment banks globally have dropped from 27 per cent of overall revenues 10 years ago to 23 per cent last year, according to data by Thomson Reuters. In the third quarter of this year, the total value of global M&A deals has fallen to a level that was only lower on two occasions in almost nine years.

“Deal advisers have become less and less important in the way they are perceived internally. Many are starting to lose their sense of belonging,” says one senior dealmaker who left this year to set up his own company.

Another banker who set up his own M&A related company says: “If you are good at your job, do you sit in a bank today? No way. Bankers who might have made $10m or $20m dollars a year from M&A are now getting $1m and even those bonuses are getting regulated away.”

Other bankers become freelancers out of simple desperation. “It is also an opportunity for some bankers to ride the market out while staying in front of clients and waiting for the hiring at the banks to pick back up,” says Jason Hanges, managing partner at recruitment firm Quest Group in New York.

But many discover that the balance sheet and product expertise of their former employers have been more crucial than they thought.

“If you have been used to carrying one of worlds biggest investment bank business cards, you realise it’s not as easy to get the next job when suddenly you are not,” says one senior dealmaker who also left a large investment bank.

Tactics change for new rainmakers

Right time, right place. That, for some of banking’s best-known rainmakers, is the simple truth. Over the past two decades they were in senior roles at banks to witness, and enable, some of the biggest and most dramatic deals in corporate history, writes Anousha Sakoui.

While the removal of these stars will allow younger dealmakers up the ranks, they will not have had the same blockbuster megadeals to cut their teeth on.

With M&A volumes at multiyear lows, analysts at Thomson Reuters are only forecasting in 2013 a “modest uptick expected in M&A compared with last year – led by the healthcare sector”.

M&A has been a training ground for star bankers since the 1970s, when Robert Greenhill – who founded his own advisory boutique – launched Wall Street’s first M&A department, then at Morgan Stanley.

The ’80s, ’90s and 2000s saw blockbuster after blockbuster – with each deal developing new tactics. Bankers such as Mr Robey were in the mix from the early ’80s onwards. In the US, the $30bn takeover of RJR Nabisco made history as the biggest deal on record in 1988 – retaining that crown until 1995.

In the 1990s the Zaoui brothers were in the thick of the oil merger wave. In 1999, the two brothers, drafted in by French oil group Elf Aquitaine to defend it against a hostile takeover from Total Fina, its rival, devised the first “Pac-Man” defence in France, whereby a target turns on the bidder by making an offer.

The 1990s and early 2000s saw other industry defining mergers such as BP and Amoco, HP and Compaq, Arcelor & Mittal, Vodafone and Mannesmann – still the biggest deal on record at $202bn.

These bankers had the ear of the world’s corporate leaders, who would maintain long standing relationships with chief executives on behalf of their institutions. “These are some of the last of the relationship bankers,” says Scott Moeller, director of the M&A research centre at Cass Business School. Some observers argue that banking relationships are today more focused on transactions.

However, the next generation of bankers are working in a new dealmaking environment. “The reality is that while someone out of business school in 2007 won’t see the same deal flow as someone who started in 2000, what it takes to close a deal has changed,” says Mr Moeller. “What worked in 2007 will not necessarily work today – for example before the crisis the battle was all about price and speed. Now governance for example is more important.”

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