All roads lead to Silicon Alley, or so it seems these days. You have your Wall Street quant to founder to investor route, your hedge fund to VC route and the Goldman Sachs to seed stage variant. There’s the standard McKinsey analyst to cofounder path, and then the rarer pivot from real estate sales to serial entrepreneur to co-working impressario. We’ve watched the leap from TV news producer to founder. What’s to stop them when even tech bloggers with big swagging … talent at picking companies are crossing the table to get to the other side.
One path you don’t see very often, however, is public relations to angel investing, which is a trajectory Dorothy Jean, vice president at Brew Media Relations, is choosing to pursue with the launch of Liberty City Ventures. Over macaroons in the Flatiron District last week, Ms. Jean–a familiar, smiling presence in startup circles–told Betabeat the fund has raised an undisclosed sum from private investors and already made a couple of investments.
As we noted in our profile of Brew founder Brooke Hammerling last year, the boutique tech-focused public relations firm attracts clients like WordPress, One Kings Lane and NetSuite, in part through Ms. Hammerling’s sizable network. (WordPress founder Matt Mullenweg came on as a client after he met Ms. Hammerling on a Charity Water trip to Ethiopia; Ms. Hammerling knew Zynga founder Mark Pincus–husband of One Kings Lane founder Alison Pincus–from her dotcom days in the Valley. Indeed, Brew once represented Zynga as well.)
The firm, which is headquartered in Soho, has also served a number of New York City darlings, such as the ever-expanding urban campus General Assembly and GroupMe*, which was acquired by Skype last August.
“Last year, three of our clients actually were acquired, so we’ve seen a lot of exits lately,” said Ms. Jean, who has worked closely with GroupMe, Adaptly and Bluefin Labs. “Being surrounded by so many startup companies, it’s hard not to get bit by that passion and want to start something on your own.”
Ms. Jean, who has been working in tech PR for eight years, will be a partner at Liberty City Ventures, along with her fiancé Andrew Chang, COO at Condition One, which offers technology for playing immersive video. Prior to joining the startup, Mr. Chang was an associate at TechStars New York, which incubated Condition One as part of its most recent class.
UPDATE: Ms. Jean revealed that Liberty City’s other two partners in the fund are Emil K. Woods and Charles Cascarilla, the cofounders of Cedar Hill Capital, an alternative investment firm. The pair are both helping to manage and personally investing in Liberty City. Businessweek describes Cedar Hill as a privately-owned hedge fund founded in 2005. Mr. Woods is an alumnus of SAC Capital Advisors, a group of hedge funds founded by billionaire Steven Cohen. Cedar Hill boasted huge returns in 2007 and 2008 by betting against the subprime market, only to have returns dive the following year. Last month, Mr. Woods donated a $1 million gift to his alma mater, UPenn’s Wharton School, to help student entrepreneurs through the Wharton Venture Initiation Program.
Switching gears from PR to investing isn’t an unprecedented move, Ms. Jean pointed out as she tore open the wrapper on our dainty bag of pastries. “Look at Margit Wennmachers at Andreessen Horowitz. Not that I’m anywhere near her level, she founded Outcast PR.” Ken Lerer of Lerer Ventures also started his career in communications with his firm Robinson Lerer & Montgomery. Somewhere in between the two, of course, he co-founded the Huffington Post.
“We’re not raising a full-fledged round,” Ms. Jean explained, “because to start we don’t want to be limited to the pressure or obligation of allocating a certain amount of funds by a certain amount of time, so we can be pickier and more disciplined.” She declined to specify the size of investment beyond the “typical range” for seed stage. Despite that easy smile and girlish laugh, she’s seasoned in her craft, cutting off our question with, “That’s as far as I’m going with that.”
Liberty City Ventures–a name meant to reference New York City, by way of Grand Theft Auto–will focus on local investments in digital media, as well as consumer web and mobile startups. “There’s so much more that can be done in the way we consume and distribute content and create it, especially in New York,” said Ms. Jean, adding, “I think there are still a lot of traditional industries that can be disrupted by technology.” She pointed to BaubleBar, another Brew client. “I think all the middlemen are being cut out and e-commerce is still going like crazy.”
Besides those parameters, Ms. Jean said she will gravitate toward startups where her skill set can help her investments. “A lot of early-stage startups shouldn’t be paying for communications. They should definitely be dedicating their resources toward building their technology and their product,” she explained. “I’m not pushing anyone to be out there and make a noise about themselves before they should, that’s not the point, for sure. But I think a lot of good companies do struggle with who they are and what they represent, and going through the exercise of ‘How you would describe yourself to other people?’ can be really helpful. Not saying that that’s going to determine your business model or what you’re going to do, but it can certainly help.”
Like a typical angel fund, Liberty City’s partners will only be devoted to the fund part time. Ms. Jean will continue consulting in PR on the side. In her role at the fund, she said, she will be vetting potential investments. “There’s a lot of that kind of more rigorous financial detail that I’m learning and that some of my partners bring to the table. Fortunately, otherwise I would not be able to do this,” she acknowledged.
However, she reasoned, her experience at Brew has helped her get a lay of the land. “Brew famously doesn’t pitch business because there are so many opportunities that are coming our way. So we’ve gotten to kind of that habit of vetting companies and trying to pick the right horse,” she said. “Being in PR, trying to stay on top news and trends and how I can insert my clients in the news—I’m keeping an eye on everything that’s going on. All of that put together helps me feel like I have some sense. Nobody knows for sure what’s going to win.”
Brew itself as been expanding both here and in its West Coast office. “While we are GUTTED (I say that b/c I’m in Europe and that’s what you say) she’s leaving, I’m blown away by the team and yes we are indeed growing like a weed,” Ms. Hammerling told Betabeat by email, adding, “We are excited to see her rock it.”
As for what advice she’s gotten from fellow New York angels, Ms. Jean said, “Some are pushing you to be more aggressive. If you’re new and early, you can get elbowed out.” Others, she said, offered tips on “when it’s right to get in the way, when it’s right to stay away.” For now she’s “approaching it as any entrepreneur would. Nobody knows exactly what they’re doing when they’re starting a company,” she added with a laugh.