If MySpace.com founder Brad Greenspan gets his way with Dow Jones Inc. — and admittedly, it's a long shot given he's up against the likes of Rupert Murdoch, whose Fox Interactive Media paid $580 million for MySpace in 2005 — he may ultimately go head to head against YouTube Inc.

On Wednesday, a Greenspan-led group offered to pay $1.25 billion for 25% of Dow Jones’ shares at the $60 per share level that Rupert Murdoch’s News Corp. has bid. The group would invest an additional $250 million "to accelerate the expansion of its high-growth potential Internet/online/digital/broadcasting businesses," explained Greenspan in a letter to the board of directors. Within 18 months, Greenspan’s group would launch an ad-supported video network, with original content designed around The Wall Street Journal, MarketWatch and Barrons, as well as licensed video and user-generated content.

Sounds like YouTube, all grown up — and monetized. While YouTube is certainly the most popular video-sharing Web site on the planet, it has yet to make a profit. Nevertheless, many investors are betting big on video. Two of the best-funded privately held companies in Tech Confidential's special report on convergence in this week's issue of The Deal are online video companies. Online video distributor BrightCove Inc., which Wednesday won Fox Entertainment Group's Web video business, has raised $81.2 million from investors over three years, and Joost Operations SA, the peer-to-peer streaming video site, has raised $45 million in a single round. —Mary Kathleen Flynn

See June 20 story on TheDeal.com
See Greenspan's letter to Dow Jones board of directors
See story June 18 on TheDeal.com
See story on ScreenPlaysmag.com