Neil Utley, the colourful City entrepreneur, has been banned from working in the Lloyd's of London insurance market for two years and ordered to pay £130,000 in costs.
The 51-year-old has agreed to settle two cases of "detrimental conduct" with the 326-year-old City institution, linked to his tenure as the chief executive of underwriting syndicate Equity Red Star between 2005-2010.
Equity, which has since been bought by a United States private-equity firm, ran into difficulties due to mounting personal injury claims.
Lloyd's said Mr Utley failed to ensure there were "sufficient systems and controls" at the troubled group.
He also failed to provide its board with "sufficiently comprehensive management information" relating to its claims, the market added.
Mr Utley owns record label, Nusic Sounds, and controls part of Hastings Insurance Group, which is widely tipped to be seeking a stock market flotation over the coming months.
Nusic Sounds counts former Busted singer Charlie Simpson as its star attraction. In a statement shortly after the fine and ban was announced, Mr Utley said: "The Notice of Censure confirms that my behaviour was not deliberate, wilful or even reckless and that I did not act in a dishonest manner or make any personal financial gain.
"Lloyd's notes that this was a period of difficult conditions across the entire motor market and they state that none of the matters they reviewed caused any increase in claims or loss to policyholders.
"Having resolved all of these regulatory issues I will now be free to devote my time and attention to building on the considerable success that we have enjoyed at Hastings."