Like a lot of people who are concerned about the future of journalism in the digital age, I’m still wondering what we’re supposed to have learned from the demise of Chi-Town Daily News last month. So I called one of my favorite editors of all time, Jacqui Banaszynski, who sits on the nonprofit’s board.

Turns out Jacqui is struggling with the same question.

The need to raise money to replace Chi-Town’s start-up funding from the Knight Foundation was well understood by the board, she told me. But what could have been done differently to keep Chi-Town going? That’s much harder to pinpoint, she said.

Among the headwinds Chi-Town and founder Geoff Dougherty faced were the severity of the economic downturn, she noted. It also “was trying to keep the geography in journalism in a new digital and citizen-choice environment. No one has yet figured out the pay model for that.”

But she also wonders, as I have, whether the skill set of a journalist necessarily translates to that of a nonprofit executive. As Jacqui said, “I’d hate to be judged for my success as a businessperson and fundraiser when what I really am is a journalist.”

She suggests that foundations such as Knight that have invested so heavily in Chi-Town and other startups take an extra step — help them develop the kinds of expertise they will need to sustain themselves. While ProPublica did get a $1 million Knight grant to get that kind of help, the rest are pretty much on their own.

“So if there’s a cautionary note here, maybe it’s to make sure new ventures are a partnership of people who know how journalism works and how money works,” she told me. “Maybe the gracious foundations who are out front in their efforts to protect the vital role of journalism in society need to dedicate part of their funding support to develop business acumen while these start-ups find their footing.”