Back in the day, I covered Winebaum closely, first during his stint as the go-to Internet guy at Disney and after he left there to strike out on his own with serial entrepreneur Sky Dayton. It was all very glamorous then.

But some of what they attempted, especially an “incubator” to build Internet start-ups from the ground up called eCompanies, did not work out as the hype swirling around it then promised.

Nonetheless, you only need a few hits to cover up all the misses, and it looks like Winebaum might have one soon, after toiling in relative obscurity since then in the less-exciting business-to-business space.

Business.com, which is essentially a highly targeted search-and-directory site, is being looked at by several companies, including Dow Jones (owner of this site, too), as well as News Corp. (likely for its new business cable channel) and the New York Times Company.

The price? A cool $300 million to $400 million.

That’s a lot, of course, and a sweet price being bandied about, especially since both Winebaum and Dayton were widely mocked–including by me–for paying $7.5 million for the domain name in 1999.

Now that it looks like News Corp. might be buying Dow Jones, it is not clear where the deal to sell will land, but here’s a video of Winebaum talking about the site:

In its first incarnation as a business portal, with lots of content, it almost went belly up, but Winebaum refocused it as a search service for business–and gave it the most dull, but useful, interface you might find out there. In essence, it links buyers of various business goods and services with merchants.

Another interesting part of the business is its related Work.com site, which solicits and vets content about various business issues from users (often consultants looking for business) and posts them.

“I found we were spending 80% of our money on the part of the business that brought in 20% of the revenues,” said Winebaum, speaking of Business.com’s first efforts at heavy original editorial content, which resulted in major losses. “And when it was clear that the search and directory was exactly the opposite, it was obvious what we had to do.”

Since then, helped by another $10 million round of investment a few years ago, the business has been throwing off cash, about $15 million in earnings before interest, taxes, depreciation and amortization.

Perhaps not as glamorous as working for the Mouse, but not bad.

Well, look who’s laughing now. Business.com is up for sale and some say it could fetch anywhere from $300 million to $400 million from media companies in need of some online growth–Dow Jones or the New York Times, for example. That’s quite a bit of money for what’s essentially a directory of sponsored listings. Still, it does make money–$15 million a year or so. So, a $350-million acquisition price would be 24 times current revenue. Not bad for an initial investment of $7.5 million and some beads …