“My father was a racehorse trainer and gambler. That was my training,” explains Christopher Dennistoun, peering over his specs and leafing through a limited edition of Jesse Livermore’s How to Trade in Stocks.

The two aspects of his professional life – “I speculate, I deal in books a bit” – have dovetailed neatly in the amassing of what is, at more than 750 titles, probably the world’s largest and most comprehensive collection of books on financial speculation. “I never set out to build anything definitive,” he says, surrounded by everything from rare first editions to even rarer brokers’ sheets, pamphlets, ticker-tape and the like. “I just wanted to read around the subject and collect some books, found I had reached a critical mass, and then the internet happened.”

Forming a collection offering a balanced overview of the history and development of the stock and commodity markets, primarily in London and on Wall Street, from the 17th century to the mid- 20th, has been “like piecing together a wonderful, enormous jigsaw”. It has taken him 20 years to amass this collection of leather-bound and boxed first editions and modern editions in their original dust-wrappers. It is on show and up for sale en bloc at Bernard J. Shapero Rare Books in London with a price tag of £375,000. “I’ve just run out of room for it,” says Dennistoun, who hopes to continue to fill the odd gap on behalf of the collection’s putative new owner.

That owner will find a wealth of hot tips and salutary tales, vitriol and humour. It all begins in the coffee houses of late-17th-century London, the source and dissemination point of political, economic and financial news. There is, for instance, an extremely rare broker’s sheet, measuring just 10in by 4in, issued by John Castaing “at his Office at Jonathan’s Coffee-house” on May 3, 1698 in a strange prefiguring of Starbucks and a laptop. Castaing’s publication was the first in an unbroken chain of published share prices and the earliest evidence of organised trading in marketable securities in London.

A year before the world’s first great stockmarket crash in 1720, Daniel Defoe wrote his famous condemnation of the broking community. The Anatomy of Exchange Alley (1719) describes in detail various alleged market manipulations and sham reports generated to push up stock prices to the advantage of the perpetrators. “’Tis a compleat system of knavery; that ’tis a trade founded in fraud, born of deceit, and nourished by trick, cheat, wheedle, forgeries, falsehoods,” he blustered.

Satirising this mania for speculation – be it Tulipo-mania in Holland, John Law’s Mississippi Scheme in France or the South Sea Bubble in England – is the fascinating if elliptical The Great Mirror of Folly (1720) an anonymous Dutch book which is stuffed with “prints, comedies and poems” and “printed as a warning to those who come after, in the ill-fated year, for many fools and wise men, 1720.” As one of those wise men who lost a fortune, Sir Isaac Newton lamented at the time: “I can calculate the movement of the stars, but not the madness of men.”

That theme of madness was taken up by Charles Mackay in Extraordinary Popular Delusions and the Madness of Crowds (1841), which is still regarded as the best book about market psychology. Mackay identifies greed and fear as the prime movers of the markets, remarking: “Men, it has been well said, think in herds: it will be seen that they go mad in herds, while they only recover their senses slowly, and one by one.”

Booms and busts dogged the 19th century, too: New York in panic in 1857; South America gripped by gold fever, and the British by railway mania. From the latter comes the first anonymous tip sheet (of the 1830s), and the first appearance of a serious City journalist: David Morier Evans, City correspondent for The Times. By now, Wall Street was a mighty force and by the turn of the century all indexes marched to the Dow. The taste for speculation even spawned a new literary genre, the Wall Street novel such as Upton Sinclair’s The Moneychangers (1908). Of the biographies, the most celebrated must be Lefevre’s Reminiscences of a Stock Operator (1923), a paean to the most successful speculator of them all, Jesse Livermore, who won and lost several multimillion-dollar fortunes before committing suicide in 1940.

A pioneer in technical analysis was Richard D Wyckoff who founded The Magazine of Wall Street and, under the waggish pseudonym of Rollo Tape, wrote the classic Studies in Tape Reading (1910), arguably the earliest work on market dynamics and analysis. Dennistoun’s researches have also revealed the long-forgotten Karl Karsten whose Scientific Forecasting of 1931 laid the foundation for the first hedge fund, talking of “the hedge” principle to describe his own long/short style of portfolio management.

In his last chapter, the prescient author discusses tide-predicting machines and anticipates the possibility of a machine to predict economic tides. What would it make of the chances of this collection ending up in the offices of one of today’s hedge-fund managers?

The collection will be on view from May 16-28 at Bernard J. Shapero Rare Books, 32 St George Street, London W1, tel: +44 (0)20-7493 0876; www.shapero.com