Philly Builds is a guest post series profiling local founders and sharing why they chose Philadelphia as the place to launch and grow their startups. This edition is by Erin Feeney, VP of business transformation at Cotality and co-organizer of the workgroup Philly Tech & AI Alliance.

When Jake Stein talks about Philadelphia, he does not sound like someone settling.

He sounds like someone choosing.

That distinction matters. Stein has built multiple companies, gone through Y Combinator and spent time in the kinds of startup circles that often pull founders toward Silicon Valley or New York. But he keeps building in Philly.

At first, the decision was practical — though not at Common Paper. When Stein cofounded RJMetrics nearly two decades ago, Philadelphia made financial sense. The team was bootstrapping, had limited savings and was building in a city where taking an early-stage swing was more economically realistic.

“One of the really fortunate things is a lack of an echo chamber.”

Jake Stein, Common Paper

By the time Stein and cofounder Ben Garvey launched Common Paper and raised a seed round, Philadelphia was already home. 

“The very short answer is I really like it here,” Stein said. “Now when you ask the question, ‘Why am I still here? Why do I keep working on startups here?’ I think a lot of it is about community.”

For Stein, that means both life and work. He went to college in Philadelphia. He met his wife here. His family is here. Professionally, he has spent about 20 years building relationships in the city and, in some cases, building companies with the same people more than once.

That kind of continuity is part of what he thinks outsiders miss when they reduce startup ecosystems to a numbers game.

“Sometimes people think about an ecosystem, and they try to judge it on a single dimension, like size,” he said.

Instead of an echo chamber, a mixed community

Philadelphia may not win on sheer volume. But Stein believes it offers something many larger startup hubs struggle to preserve: a healthier mix of voices and viewpoints.

“One of the really fortunate things is a lack of an echo chamber,” he said.

In some startup communities, he said, founders are surrounded almost entirely by people chasing the same trends, speaking the same language and reinforcing the same assumptions. Stein sees pros to that kind of density, but also real downsides: groupthink, trend chasing and an overemphasis on what matters right now.

Philadelphia interrupts that pattern.

Here, he said, founders are just as likely to spend time with lawyers, chefs, accountants and barbers as they are with technologists and investors. That broader context can be an advantage, especially for founders trying to build companies that last.

At Common Paper, the company Stein now leads, long-term thinking shows up clearly in the product. The company is reimagining how contracts work, based on a simple but pointed premise: contracts should behave more like APIs than “pictures of pieces of paper.”

That same mindset is shaping how the company approaches AI.

Stein is not interested in bolting AI onto a product just to satisfy the moment. He is focused on what will matter over the next decade, not just the next release cycle. He pointed to a line from Common Paper cofounder Ben Garvey that captures that view: Building for AI agents today is like building a website in 1995. 

Stein also talks about what the region already does better than many people realize.

One example: data.

Stein mentioned what some people call the “Philly Data Mafia,” a shorthand for the city’s outsized influence in data and analytics. He points to RJMetrics, the company he cofounded with Bob Moore, as one contributor to that story. Alumni from that orbit went on to help build breakout companies including dbt Labs and Omni.

“There is just a critical mass of that talent and experience here,” he said.

‘There’s no reason someone else should beat us’ 

Asked what he took away from Y Combinator, Stein said what stood out most was the shared understanding among founders that they could be candid about what was not working, the hard challenge, the embarrassing setback, the personal doubt and trust the room enough to ask for help.

That culture created a kind of healthy pressure; not performative, but motivating.

YC did not make startup life easier, Stein said. If anything, it made it harder in the best possible way. Being surrounded by smart, ambitious founders making fast progress raised the bar. .

That is one of the things he would most like to see more of in Philadelphia.

“I wish more people had the assumption of just sort of like, we can,” he said. “There’s no reason someone else should beat us.”

That may be the clearest expression of Stein’s challenge to the local ecosystem.

He is not arguing that Philadelphia should try to become Silicon Valley, he said. In fact, much of what he values here comes from the fact that it is not. But he does think the region could use more of the opposite of imposter syndrome: more founders who assume they belong, more companies that aim at category leadership and more people who start from the belief that the biggest outcomes are possible here too.

If he were pitching investors outside the region, Stein said he would describe Philadelphia as an undervalued market. For firms that talk constantly about proprietary deal flow and less competitive opportunities, that should be appealing. The inefficiency, he suggested, may not last forever.

After everything he has seen, across startups, across cities and inside one of the best-known founder networks in the world, Stein’s optimism about Philadelphia still comes back to the same thing.

“It’s really the people,” Stein said. “There’s so many amazing people that I trust, that I like, that I admire, that I learn things from.”