Simon Nixon, the co-founder of price comparison site Moneysupermarket.com (LON:MONY), has sold £56mln worth of shares in the company.
The entrepreneur, who set-up the business after dropping out of university in 1999, sold 20mln shares on Monday night - around 3.7% of the company - at 280p each.
Nixon has now made close to £400mln from the company, including the £100mln he made when the business listed in 2007.
He offloaded an 18.5% stake worth £200mln in June 2013 and sold a further 10.6% of the company - worth £129mln - in March 2014.
The latest sale comes after a u-turn in March, when he announcing plans to sell a £100mln stake in the business before cancelling the sell order just 15 hours later.
Nixon still owns around 12.8% of Moneysupermarket.com following the placing, the company said today.
His stake is now below a 15% threshold where he is entitled to nominate an executive director to the board, although Nixon has never taken up this right.
Last month Moneysupermarket said it had enjoyed strong growth in the first quarter of this year, with revenues more than tripling to £77mln.
Shares hit an all-time high last week of 303p, but have since fallen back to 294p giving the company a market value of £1.6bn.