Amazon founder Jeff Bezos says he will sell another 25 million shares in the technology giant, worth nearly $5bn (£3.9bn).
It comes after the company's stock market value hit a record high on Wednesday.
In February, he announced that he would sell Amazon shares worth around $8.5bn.
That marked the first time since 2021 that Mr Bezos had sold Amazon shares.
The company's shares have risen by more than 30% this year on expectations that growing demand for artificial intelligence (AI) technology will boost earnings at its cloud computing business.
Last month, Amazon's stock market valuation topped the $2tn for the first time.
However, that is still behind other major technology firms Nvidia, Apple and Microsoft, all of which have crossed the $3tn mark.
Amazon reported robust quarterly earnings at the end of the April, that showed the company's bet on AI was paying off.
Mr Bezos stepped down as the company's chief executive in 2021 and is currently its executive chair and remains its largest shareholder.
He founded Amazon in 1994 in a garage in Bellevue, Washington, when the internet was still in its infancy.
The company started out as an online bookseller, touting the world's largest collection of ebooks.
Since then Amazon has become one of the world's leading online retail and cloud computing companies.
He also founded the rocket company Blue Origin, which in May sent six customers to the edge of space.
Mr Bezos is the world's second richest person, according to the Forbes Billionaires list, with an estimated net worth of around $214bn.
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