Barnes returned a third time to colead one of its Innovation sessions with David Rose, an "angel" investor (someone who puts up money for a start-up company) and founder of New York Angels, an organization of such investors.
Barnes and Rose spoke before an audience of about 50 entrepreneurs from start-ups and digital agencies.
In an e-mail, Barnes summarized his theme - that the venture-capital user experience "is broken and needs to change as the market makes it more and more clear that VCs [venture capitalists] are on the sell-side, not the buy-side."
The topic was urbane, but Barnes' attire was urban from head to toe: jeans, bright sneakers, and a graphic T-shirt that declared "BE A FOUNDER." He looked more like a trendy Brooklynite than a professional investor.
"If I'm more dressed up, I'm uncomfortable," said Barnes, who has sported informal apparel since his days as the creative director of athletic shoe company AND1. Employees wore the company's products. "It's harder to wear a suit with sneakers," he mused.
To an outsider, the relaxed vibe of the ensemble would belie, rather than suggest, financial savvy. But Barnes and Rose (who wore a suit) both meant business.
Barnes discussed how venture capitalists often take their time before decidinge whether or not to fund a project, while Rose added that if a business does not at least promise an outsize return, it may not attract venture capitalist or angel funding in the first place.
For Alex Urevick-Ackelsberg, cofounder and chief executive officer of Web developer Zivtech (also headquartered in Philadelphia), sincerity trumps appearance. Of Barnes' fashion sense, he said, "I don't care if he was dressed in a clown suit, as long as he comes across real."
Real, these days, looks a lot like hip. Even Barnes' slideshow presentation ( www.slideshare.net/PhineasBarnes) oozes casual cool, from its snappy, shorthand title, "The UX of VC," to slides with cheeky cartoons, graphics, or memes. The icon for a venture capitalist, for instance, is a man seated, legs crossed, on a cloud.
If he wore a tie, Urevick-Ackelsberg said, "people would think that I was going to court or something."
It would be easy to assume that millennials and Gen Xers are responsible for a trend that reflects the simple, streamlined aesthetic of cutting-edge apps and websites such as RoboPhone, which teaches children how to code.
Yet geography, as well as generation, may also be at work. Urevick-Ackelsberg said he thinks, to some extent, that "it seems more like a West Coast/East Coast thing." After all, laid-back surfer style, itself a cultural phenomenon, started in California.
Barnes, less sure about the bicoastal origins, said you can spot venture capitalists, management consultants, and wannabe investors donning the same uniform, a blue button-down and khakis, on both sides of the country.
At Northside, though, the impact of geography isn't exclusively sartorial. Austin and Williamsburg both have reps as hipster enclaves.
"Williamsburg has gone through this big, crazy housing boom in the last five, 10 years. When you go to Austin, there's nobody there but the people for the convention," Urevick-Ackelsberg said. "When you go to Williamsburg, it's going to be packed every night of the week. . . . You're surrounded by all this business going on. You didn't really have to have a badge."
Both SXSW and Philadelphia Tech Week, which news org Technical.ly Philly hosted in April, had, he said, a "more cohesive feel."
The Brooklyn boom also means, of course, that rents have skyrocketed, one reason Urevick-Ackelsberg left Greenpoint seven years ago and moved back home to Philly. (He grew up in Germantown.) The high cost of living in Brooklyn, he said, makes it a better place for "firmly established" entrepreneurs to live than for start-up execs.
And anyway, he prefers his hometown for its sense of community: "Philly has a bit of an envy thing with regard to Brooklyn. I think it's a little bizarre, honestly."
First Round, too, has a fair share of pride for its birthplace. "We're big believers in Philly as a city," said Barnes. "We continue to be there and build our company there and see others build their companies there."
No matter what spats over metropolitan cultural cred emerge, there is no denying the ubiquity of the tech set. "The power of the tech community," Barnes said, is that "it's both national and local at the same time," fueled by people "sharing ideas across geographies."
Philadelphia Tech Week may lack the indie/arts pizzazz of Northside, but Urevick-Ackelsberg said the quality is higher.
"The takeaway is that we've got to get better at marketing, which is always the story with Philly," he said. "We have a great thing going on here - which makes me miss Brooklyn not nearly as much as I did."
Karen Meidlinger contributed to this article.