As 2006 drew to a close, Voice had been in operation nearly two years. Through their first full year running Voice , Donohue and Lewis had concentrated on the editorial side. Overseeing a small but growing staff, Donohue had enforced, in his words, a “relentless focus” on San Diego quality of life issues. He assigned reporter Rob Davis to cover environment, Kelly Bennett to cover housing and the economy, and Emily Alpert to cover education. Evan McLaughlin, who along with Donohue had been one of Voice ’s first hires, focused on City Hall and politics. Donohue himself also wrote about city government while strategizing about future investigative projects. Lewis, while maintaining his weekly column, had become the website manager.

But a different clock had been ticking. December 2008 was the end of the grace period during which Woolley could bear most of the site’s costs himself if Voice wanted to qualify as a public charity. Voice was a long way from weaning itself off Woolley, who still provided some three-fourths of the site’s operating budget. Thus far, Lewis and Donohue had largely left financial questions to the board and had only a hazy grasp of what Donohue calls “the general money-getting operation.” For example, explains Lewis, “it took us literally a year to understand that marketing, fundraising and [selling] advertising were three completely different things.” They had learned this mostly through trial and error. Lewis says:

We kept hoping, and the board kept hoping, that we were going to find this magic businessperson, this marketing person that would come in and just shape us up… But for $40,000 or $50,000, you’re not going to find the magic person that does all these things, that can come in, feel the passion of the organization and translate that into [money].

At first, the board thought Voice needed a marketing specialist

— someone who, Donohue explains, “could get [our name] out at the street fair. But then they were also expected to get advertising funds and to get fundraising dollars.” The board hired and fired two different marketing specialists between 2005 and 2006; neither had the skills or background to take on fundraising and ad sales in addition to marketing. It dawned on Lewis and Donohue that the board might be recruiting for the wrong job. Just because their reporters were successfully multi-tasking did not necessarily mean they would find someone able to market, fundraise, and sell advertising with equal competence.

Lewis and Donohue themselves had so far proven more adept at saving money than at finding new sources of it, and they knew they needed help. Though the board had brought in some additional sources of funding—mostly from local foundations and philanthropists—to supplement Woolley’s backing, Voice had no one dedicated full-time to development as the site entered its third year in 2007.

It was imperative to diversify the funding base. In consultation with the board, Lewis and Donohue determined that their priority should be fundraising, rather than marketing or an ad campaign. Concretely, this meant persuading organizations or individuals to contribute. So Lewis took charge of grants and funding drives. In mid-2007, the board hired Camille Gustafson as development director to assist Lewis in those efforts. She joined Voice with a sense, she says, that “there was some foundation money out there, and we should try to find out how to tap into some of that.” [1]

It was in some ways harder to find donors than investors, who could expect at least some return on their money. Lewis explains:

For-profits can raise a lot of investment money, and I think that we’ve been told several times that if we were… somehow able to switch to a for-profit, we could raise literally millions… But we never understood how to return that investment, how to make money on it. And Buzz [Woolley] has said, "If [ Voice ] were a for-profit, I would have walked away."