James Packer raised $261 million late on Wednesday by offloading separate holdings in online employment major Seek and boutique funds group Magellan.
Investment bank UBS placed the shares in both groups to institutional investors.
The Seek holding represented 4 per cent of the company. The sale raised $125 million after Seek shares were offered at $9.28 each.
The Magellan shares were offered to investors at $10.68 each, raising $136 million.
The bulk of the funds are expected to be used to pay down debt and other investments.
While Mr Packer sold down his cornerstone stake in Seek in 2009, netting $441 million, he moved back into the online classifieds firm in recent years, building up a small stake. Wednesday's move also marks the end of Mr Packer's long connection with Magellan, the investment fund founded by former UBS Australia boss Chris Mackay and former Deutsche Bank head Hamish Douglass.
Seek shares closed up 4 per cent at $9.76, while Magellan ended up 1.8 per cent at $11.68.
The sell-down came as Seek said it was reaping the benefits of diversifying into education and international markets, after more than doubling profit in the face of a sluggish domestic jobs market.
The company's headline profit jumped 128 per cent over the year to $300.1 million.
However, this was inflated by a write-up in the value of further shares in Zhaopin, the leading employment job ad site in China.
After stripping this out, Seek's underlying profit was up 8 per cent to $141.1 million. The key drivers were strong growth across education, robust results in Seek's international arm and a solid performance by the flagship Australian jobs business, said chief executive Andrew Bassat.
Underscoring the pressure from the Australian economy, revenue from the domestic job listing business declined 5 per cent.
The number of new jobs listed during July fell 1.3 per cent.
"Seek cannot control the economic cycle but we can strongly influence our market position," Mr Bassat said. The company is estimated to have 70 per cent of the online job ad market in Australia.
Mr Bassat was cautiously optimistic about the employment market outlook and said consumer and business spending might pick up again after the election.
Seek's education division emerged as the largest contributor to revenue. Mr Bassat said the business gave a degree of "counter-cyclical protection against weak labour markets".
The division provides course-matching services to students and educational providers.