In order to finance World War I, the British government sold war bonds to millions of investors and savers, thereby prompting a wider interest in financial securities including stocks and shares during the interwar period. Faced with a large intake of investment newcomers, the City of London was anxious of ‘amateur’ involvement in the market. The largest securities market, the London Stock Exchange, restricted access to small investors where possible, which pushed much of the new retail activity to the market fringes. Here, ‘outside brokers’ and ‘bucket shops’ catered for investment newcomers, the more gullible of which fell prey to fraudulent share pushers. Scholars have entirely overlooked this vibrant grey market for financial securities. But it was here—and not just at the organized exchanges—that ever more people made their first experiences with the ups and the downs of the stock market, most prominently in the great crash of 1929. This new perspective brings a sharper contour on some fundamental challenges that Britain’s financial landscape was facing in the interwar period: a large intake of new investors, a resurgence of financial fraud, and a new struggle over the distinction between speculation and gambling. The City’s response to these challenges can be described as financial paternalism. After a surge in political democratization, there was very little appetite to enfranchise ordinary people in the stock market. Instead, institutions like the Stock Exchange deliberately took a conservative stance on the ‘democratisation of investment’.