Cuneo reflects on Observer’s journey from idea to print

If Charlie Cuneo had not volunteered his leadership, the Weston Observer might still be in the planning stages.

“We’d still be working on it, I think. We would have tried, but I don’t know if we’d be through it yet,” said Joan Heilbronner, incoming president of the Observer board of directors.

Cuneo, who moved from Weston to Baltimore late last year, is stepping down as board president at the end of February.

He is more modest about his role.

“We were very lucky that all of the pieces that we needed to get the paper going were in amongst the volunteers and if not, we recruited people to join the volunteers,” Cuneo said.

That team included Joel Angiolillo, who was in charge of technology, and Katie Phaneuf, who shared her skills in project management and organization. Tim Armour lent his fundraising expertise to the effort and marketing and development consultant Ali Dorman Fernandez, former director of partnerships at Emerson College, took on branding and outreach. Marion Packs acted as board treasurer and Sandy Kendall helped design and write background literature, according to Cuneo.

“We had some business background on our team, and we had some tech background. [Cuneo] really had the background we needed to move beyond … our vision,” Heilbronner said. “He was able to actually tell us what we needed to do to execute.”

Cuneo was managing editor of the Yale Daily News and director of finance and administration at The Conversation, an online nonprofit media organization. He has also run several technology businesses.

Angiolillo said Phaneuf, Packs and Heilbronner were instrumental in starting the paper, but “Without Charlie, I don’t know where we would be. You can have all the ideas in the world, but they are just ideas unless you can put them together in a real business.”

Starting out

The idea for a local newspaper originated in 2023 when Heilbronner, Phaneuf and Packs discussed the difficulties of getting news about the town after their children had graduated from Weston Public Schools.

“You start to feel a little disconnected from this town that you’ve spent 30 years in,” Heilbronner said. “Additionally, you realize how hard it is to communicate with people in town.”

Shortly afterward, Heilbronner ran into Angiolillo and found he shared their beliefs. They attended a news forum at Regis College, which gave them the push they needed to start the paper.

Packs created a survey in January 2024 to gauge interest; 600 people responded.

“People were very enthusiastic about the project, so … we decided we were going to give it a go,” Heilbronner said.

Cuneo joined the team in November 2024. In January 2025, the team began work on the Observer website, a style guide and an interim fundraising website, according to Angiolillo.

“All through 2025, we had to build up all the parts,” he said.

In April 2025 they began interviewing candidates.

“This was Charlie who said we needed professional staff, we can’t do this with volunteers,” said Angiolillo.

Bringing people together

Once Cuneo established a budget, it was full steam ahead.

“[The volunteer group has] a great set of skills and experience. Their idea was that we would form a news organization that was unbiased [and] provided information serving all the needs of the residents of Weston,” Cuneo said. “They really had the vision of bringing the community together by sharing a common source of information and news.”

Cuneo was initially skeptical they would be able to fund a printed paper, believing an online platform was the way to go.

“The volunteers really felt that having a newspaper that was delivered to every household would help really unify and inform the town in a way that a website … would not,” Cuneo said.

It turns out they were right.

“A printed paper has been a good way of getting people up to speed on what is happening in town and making people aware of everything that is going on,” Cuneo said.

Advertisers like it too, he added.

The Observer is also bringing people together, he said.

“We recruited as our managing editor a woman who believes very strongly in making this newspaper into our town square, where people would have a voice and we would host a variety of different perspectives and organizations,” Cuneo said.

“We’re not letting him go that easily”

Cuneo may have moved, but he will continue to serve on the board to ensure the paper remains solvent.

“What I’ll be involved in is making sure that we have a ramp toward being more sustainable – stronger sources of revenue [and] a committed reader base that is willing to contribute donations,” Cuneo said.

Heilbronner said she will rely on Cuneo to create a strategic plan, and she knows she can call on him for help if she needs it.

“We’re not letting him go that easily. Charlie has such a great sense of humor,” Heilbronner said. “He’s really a very thoughtful leader. He’s attentive to everyone’s opinions and he’s so knowledgeable. He’s a really likable and funny man, so I’m so happy to have met him.”