The widening path for women entrepreneurs in New Haven and beyond

Photo: Elizabeth Gore (center) speaks with Alisha Crutchfield (right) and Teresa Chahine (left), director of the Social Innovation Initiative.

“I believe in you because you believed in yourself and you were persistent.” 

With that, a New Haven landlord handed Alisha Crutchfield the keys to the space that would bring her entrepreneurial vision to life. Crutchfield is the founder and owner of BLOOM New Haven, a gathering space that takes inspiration from the surrounding community to empower all those that frequent it. 

The idea that grit opens doors even when systems don’t was one of the prevailing themes for a November 4 conversation hosted by the Yale Jackson School’s Social Innovation Initiative (SII), which highlighted women entrepreneurs. Crutchfield was in conversation with Elizabeth Gore, co-founder and president of Hello Alice, to discuss their experiences navigating the entrepreneurial space as women and barriers they faced while building a business from start to finish. 

Gore helped establish Hello Alice, a financial technology platform that connects over 1.5 million entrepreneurs to capital, connections, and education, with co-founder Carolyn Rodz. The duo worked together at the United Nations, where Gore said they were the “two token women on the same panel over and over.”

After stops at the Peace Corps, the UN, and Dell Technologies, Gore continued to pursue independent research and passion projects. But one problem persisted: how hard it is, especially for women, to start a business without deep connections.

“It’s access,” she explained. “There’s complete bias, implicit bias, and systems that even the most well-meaning bankers can’t get around.”

The path to create Hello Alice faced similar roadblocks. More than 200 pitches to investors “fell really flat,” Gore said, before she found support for the idea. Her advice to potential entrepreneurs? “Ship it, get it out in the market, start getting feedback — it doesn’t matter how bad it is.” 

While Gore mapped the process of building a business from a spark, Crutchfield stressed the importance of support and guidance of community stakeholders when taking an entrepreneurial step. “It’s not nepotism,” she said, “it’s actual relationships with individuals, banks, etc., who are going to really help you succeed.” 

Crutchfield emphasized that these barriers never really go away — entrepreneurs just become better prepared to meet them as they arise. She encouraged the audience to forge a resilient mindset, investing in relationships, and staying civically present even when time is scarce. 

Both speakers reminded the audience that while the journey of entrepreneurship is hard, every step forward makes the path wider for those who follow. “We now have to open other doors and vouch and pull people to the table,” Gore said. 

This message rang true for many in the audience. Jahkeeva Morgan, director of The Lab at ConnCorp, a business incubator and accelerator advancing economic opportunity in underserved New Haven neighborhoods like Dixwell and Newhallville, said the event was “a powerful reminder that while we’re striving, we’re also inspiring.”

“What resonated most for me was the emphasis on community, being intentional about building relationships and nurturing them over time. Community and connection are the energy that sustains both business and the broader ecosystem.” - Jahkeeva Morgan

Morgan’s thoughts mirror the mission of the Social Innovation Initiative, launched at the Jackson School in 2023. The initiative brings together students, practitioners, and scholars working on social innovation to address the world’s most pressing problems, offering elective courses, advising students, and hosting guest speakers from the New Haven community and across Connecticut.

In its inaugural year, SII hosted a fall seminar series spotlighting New Haven social entrepreneurs, including Erik Clemons of ConnCORP and Caterina Passoni ’18 of Havenly, exemplifying its commitment to learning from local leadership. This semester, in addition to the event on women entrepreneurs, the initiative hosted a panel discussion on social innovation around the world with three Yale World Fellows and began a Social Innovation Stories series which invites Yale graduate students to exchange ideas on innovation and impact.