Si Newhouse, CEO of Advance Publications

Looks like Condé is starting to put that $500 million digital war chest to good use. Today, the media conglomerate purchased grocery list and recipe organizing app ZipList, to the tune of $14 million, reported AllThingsD.

As we previously reported, Condé is no stranger to the woes of the print-to-digital transition. But since last year, the company has been bragging about a multimillion dollar stockpile of cash it'll use to help bring the stodgy old print biz up to tech speed. The ZipList purchase appears to be one of the first moves representing Condé's tentative foray into the digital sphere.

It may seem like an odd pairing, but Condé actually already owns Epicurious, a community for "people who love to eat," so ZipList should fit well alongside that property. The company also invested in Moda Operandi, a fashion startup, last September.

Oh, and ZipList fans--don't take to Twitter to voice your disgust over the acquisition just yet: AllThingsD says the Virigina-based company will continue to operate separately. Sorry, Buzzfeed.

Mr. Newhouse

Startups must be in this season, because it looks like Uncle Si is starting to pivot. Advance Publications, the Conde Nast parent company owned by the billionaire Newhouse clan, is "quietly" making a departure from the glossies, newspapers, and cable companies on which it built its empire. Keith Kelly at the New York Post reports that Advance, "armed with a $500 million war chest," is looking to invest in both the digital and startup world--both realms the company has struggled with in the past.

Earlier this month, Mr. Newhouse spun reddit out from under Conde Nast and into an independent company under Advance, perhaps hoping to better capitalize on high volume traffic, which in the case of some sub-reddits is basically as large as if they were "their own websites, ” reddit general manager Erik Martin has told Betabeat.

As Mr. Kelly reports:

"The digital investment fund, which has probably spent less than 20 percent of its capital so far, came fromthe $500 million divestment of Advance’s preferred stock in the cable channel Discovery Holdings in late 2010 and has been gathering steam since Andrew Siegel was hired fromYahoo! in January."

The fund goes beyond leveraging Conde brands. For example, the company's latest deal: a secondary investment in a Boston-based video analytics startup called Visible Measures. DAG Ventures led the $13 million round. (Partial equity is a departure from Advance's usual "all or nothing" acquisition approach. Rather, Mr. Siegel told the paper, he's making deals “anywhere from $100,000 for seed ideas all the way up to multiple tens of millions for startups that are a little further along.”  Part of that diversification strategy apparently involves a stake in Trigger Media Group, the new digital media fund with ties to McKinsey and Bob Pittman, the former president of AOL and founder of MTV.

Mr. Kelly also reports that "sometime in the next week, the Conde Nast unit of Advance is expected to announce that it has taken a major stake in Moda Operandi, the fashion startup co-founded by socialite Lauren Santo Domingo.

We wouldn't be surprised. At a startup party hosted on the Gawker rooftop in late June, Moda's other co-founder, Áslaug Magnúsdóttir, fresh of off hiring the company's CTO Matt Pavelle, shied away from talking to Betabeat for fear she would spill some big news. No need to be scared, Betabeat can keep a secret.