Ashton works part-time as a bartender at Port City Brewery, but he also runs a freelance video production company called Sequioa Pictures. “Mysterious Prison,” his low-budget feature about homelessness in D.C., was a finalist in a D.C. television pitch contest, Pitchfest, while his most recent short film, “A Celebrity,” screened at last year’s Alexandria Film Festival, as well as other regional film festivals.

Since “A Celebrity,” Ashton had a major project fall apart while he was searching for funding. Amid the fallout of this failed project, Ashton had time to think about his next move. He ultimately decided to return to an idea that he’d been wanting to make for years.

“For a long time, I’ve wanted to tell a story that was a multi-generational story about two people connecting,” Ashton said.

The initial inspiration for what would end up becoming “The Legacy Sessions” was Ashton’s relationship with his grandmother, who died from Alzheimer’s Disease about five years ago.

Ashton recorded conversations with his grandmother – and even ended up using some of her quotes verbatim in the script – and observed how Americans often fail to value the elderly.

Ashton further developed his idea after learning about the real-life Legacy Sessions, a program in Virginia Beach in which Ashton’s sister was involved.

“This high school basically connected with a local retirement community and each student got paired with a senior and got three meetings or sessions,” Ashton said. “It culminated with [the students] performing a monologue as the person they’re paired with.”

“The Legacy Sessions” film brings together two women, Darby and Flora, who couldn’t be more different, through a fictional version of the same program.

Darby is a teenager grieving after the death of her mother. Flora is 95 years old and content with the life she’s lived. Despite their differences, the two women both find themselves marginalized by a society that devalues and misunderstands them – Darby because of her youth; Flora because of her age.

For Julie Kashmanian, who was cast as Darby in September, the story bridges a generational gap that has, recently, become even wider.

“I feel like people that I talk to, or the culture that I’m in, there does tend to be this patronizing idea that generational gaps are not worth bridging a lot of the time,” Kashmanian said. “… I’ve always hated that kind of outlook. I think we should all at least just try to understand each other. I hope that people can at least come away from this film with the idea that there is value in trying to reach across that divide even if it takes a little work.”

In Darby and Flora, Ashton parallels the experiences of two “seniors,” both of whom are isolated for different reasons, Ashton said. The dynamic between the withdrawn and sullen Darby and the enthusiastic Flora – partially inspired by the mismatched relationship in “Midnight Cowboy” – makes for an unlikely budding friendship.

“[Flora’s] very expressive, and the characters are so different because her character is so expressive and mine is so withdrawn. It’s interesting to find that dynamic,” Kashmanian said.

After the frustration of trying and failing to secure funding from angel investors for his last project, Ashton turned to crowdfunding for “The Legacy Sessions.”

Ashton assembled his creative team and launched a campaign on Seed & Spark with a funding goal of $17,700 for the production budget. He started contacting everyone he knew in hopes of building a network of loyal, invested supporters.

The project needed to reach 80 percent of its fundraising goal by Nov. 24 in order to actually receive the money from donors. The project reached the benchmark earlier this week. As of press time, it had raised $14,925, or 84 percent of its funding goal, with 165 contributors.

Depending on how much money people donate to “The Legacy Sessions,” donors can receive rewards ranging from a movie poster or digital download to a custom soundtrack cassette or billing as an executive producer on the poster and in the credits.

(Read more: 13th Alexandria Film Festival brings record numbers)

“The best thing about the model is that it involves the community,” Ashton said. “It’s literally funded by family, friends [and] people who are local who want to see a project like this. It allows them to be invested in the process from start to finish, which is really cool.”

Since starting the campaign, Ashton and his team have already cast all six of the major roles. At every step of the process, Ashton has emphasized local talent and authenticity, he said.

The film will shoot in a Virginia Beach retirement home and the actual high school where the Legacy Sessions originated. Retirees and students, some of whom were involved in the Legacy Sessions, will act as extras in the film.

Paying tribute to his local roots, Ashton is putting together a soundtrack of songs from D.C. area punk rock bands including Infant Island, Park Snakes and Rabid Flash Mob.

Kashmanian, originally from Arlington, is a senior at George Mason and beat out about 300 other actresses for the role of Darby. Jacob Glasser, the actor cast as Darby’s best friend, recently graduated from T.C. Williams High School.

Meanwhile, Bonnie Jourdan, a 95-year-old actress with more than 25 years of experience performing at the Little Theatre of Alexandria, came out of retirement to play Flora. Her career may have started late – Jourdan only started performing at the LTA after she quit real estate at 72 – but she said she’s finally ready for a starring role.

“It’s such a wonderful opportunity for me, and I think this is probably my swan song,” Jourdan said with a chuckle.

Jourdan has become inextricably linked with project: Ashton rewrote the part to better fit her and ended up using some quotes from her in the script, much like he did with his grandmother.

“In the early drafts, the character was much more sarcastic and irreverent whereas now she’s a much sweeter character, more soulful, I think, just because that’s who she is,” Ashton said.

“He sat me down and talked to me for a long time and I said, ‘I see a lot of my lines in the [script],” Jourdan laughed.

The transition from theater to film acting has been a learning experience for the veteran actress. She no longer needs to project to the back seats. Instead, Ashton is asking her to bring her performance down a few notches.