Why legal staffing startup Hire an Esquire moved out west

Julia Claire Shapiro loves Philadelphia. But she doesn’t live here anymore.

For about two years, the Pittsburgh native and Temple law grad built her legal staffing startup, Hire an Esquire, in what she dubbed her adopted hometown. She kept her apartment in Philly even as she found it hard to break into the local legal industry and investor community and increasingly spent more time in New York, where it was easier for her to find clients and funders.
“We got our first AMLaw clients in NYC after a few months of sales last spring, Philly is just coming around after almost 2.5 years of banging down the doors,” she wrote to us shortly after she closed her $350,000 seed round in 2014.
In early 2015, she finally moved to San Francisco.
Hire an Esquire raised a total of $2 million, largely from West Coast investors including Stanford Angels & Entrepreneurs, DCM Ventures cofounder Dixon Doll and Targhee Ventures. But she also found that many West Coast prospective clients — law firms and corporate in-house legal departments — wanted her company to have a presence out there.
“It was becoming apparent that there was little business value to being [in Philly],” she said in a phone interview last month.
It was both a question of funding and of userbase — the latter point feels unique to Hire an Esquire, as it’s focused on the legal industry, but a city with a legendary legal culture should be able to retain someone trying to shake that sector up. She acknowledged that maybe if she were focused on a different industry, her experience might have been different. (For what it’s worth, health IT entrepreneur Todd Johnson has spoken of similar problems with getting local healthcare corporations to be embracing of innovation, though there has been a push to tackle those problems.)
On the funding point, which is something you’ve heard before, she chalks it up to culture.
On the West Coast, there’s a lot of cashed out entrepreneurs who invest as a hobby, instead of say, joining a country club or buying a boat, she said. There isn’t a strong need to make money off investments, which “makes money a lot looser.”
Compare that to Philly, where it felt like money was held close: “[Investors] want to know your childhood best friend and your social security number and that you’re going to be a billion dollar company and that they’re getting in at a good price.”
“Those expectations don’t work for seed stage startups,” she said.
Still, she counts two undisclosed Philadelphia law firm partners among her investors. Maybe they’re a new generation of Philadelphia Lawyers.
When it came to clients, she said “San Francisco was very much open arms.”
Law firms and in-house legal departments were very receptive to the company and signed contracts quickly. New York didn’t move quite as fast as Silicon Valley, she said, but definitely faster than Philly, where she said she experienced a lot of resistance. She said she got a lot of “Thanks, but no thanks” from prospective clients in Philly.
“It felt like I was banging my head against a brick wall [in Philly],” she said.
But now that she’s gotten traction in other cities, Philly clients are more open and they’re also OK with the company not having a presence in the city.
Shapiro’s team out west is small (“Two-and-half people,” she said) but aims to be at four or five soon. The company also has a five-person team in New York, including COO Jules Miller.
She said she misses Philly but San Francisco has charmed her. She lives in the Castro.
“Rarely does a day go by that I don’t meet somebody amazing,” she said, noting the city’s “crazy sense of optimism.”