Dr. Lisa Butler Grain, a retired orthodontist, comes from a family of teachers. Before pivoting to practice dentistry and serving in hospitals and public health clinics, Grain’s mother, Dr. Carolyn Lassiter, earned a master’s degree in education and taught elementary school. Grain’s grandmother was also a teacher in the Washington, D.C., public school system for more than 40 years.

“My grandmother would always say, ‘Teaching is in the blood,’” says Grain. “She died when she was 104 years old, and at her funeral, there were countless people who approached me to share how she had shaped their lives. It inspired me to continue her legacy of enriching young people’s lives.”

That’s a to-do item Grain, 60, can check off with confidence.

In 2004, she and her husband, telecommunications entrepreneur David Grain, founded the Grain Fellows program, which provides funding for SAT and college prep services to low-income students at Booker High School. The couple also covers program attendees’ college application fees, has paid to send students to summer enrichment programs, hosts seminars on etiquette and professional dress, and organizes reunions with former program graduates. Once students have decided on their career paths, the Grains connect them with other professionals in their fields.

In all, Grain says, she and David have mentored about 200 Booker High students over the years, and they do similar work at David’s alma mater, Martha’s Vineyard Regional High School on Martha’s Vineyard, where they spend part of the year.
They also support various colleges and universities, including Morehouse College and Howard University.

“Our efforts are rooted in our belief that education is a transformative tool that can change lives,” Grain says. “One of the things I say is, ‘If you see it, you can be it,’” meaning that education and higher learning can expose young people to opportunities they may not otherwise be aware of.

Grain is deeply invested in community in other ways, too. Prior to the Covid-19 pandemic, she invited local residents to attend free, nondenominational pop-up gospel services at Booker High. The effort originally stemmed from the Grains’ desire to find a church to attend when they
moved to town. However, the pop-ups grew into community-wide celebrations featuring faith leaders and musicians from around the country, including Sen. Rev. Raphael Warnock, the late Rev. Calvin O. Butts, Rev. Otis Moss, Rev. Liz Walker, Marvin Sapp, Oleta Adams, American Idol finalist and
Sarasota native Syesha Mercado and more.

“It was an open invitation for everyone to come together,” Grain says. “Our goal was to create a space where people from all walks of life could gather—from retirees and locals to young people and even visitors from out of town who’d heard about the services. We would send out an email blast and people heard about it by word of mouth. It was collective. It was joyful. It wasn’t political.” (For those who are curious, Grain says that the services will be coming back. Stay tuned.)

On top of all that work, Grain also raises money to fight pediatric cancer through Dick Vitale’s V Foundation. (A 30-year cancer survivor herself, it’s a cause she holds close to her heart.) She’s also gearing up to launch a hair care line called French
Barrelettes, which reimagines traditional hair rollers and is focused on hair health. Still, despite her high profile, she says she’s naturally introverted.

“I’m a do-er, not a talker,” she says. “I’m a listener.” So when David Carmi, who runs the popular Instagram account Confidence Heist, approached Grain on the streets of New York City last year and asked Grain to share her top tips for being confident, “it was absolutely crazy,” Grain says. Carmi’s interview with Grain wound up going viral, earning 139,382 likes and racking up 2,688 comments from Carmi’s Instagram followers.

“When he put a microphone to my face and said, ‘What makes you confident?,’ I answered with my gut and said, ‘My age,’” Grain says. “There’s a certain freedom that comes with being on this earth for a long time. You grow to realize that confidence isn’t tied to your appearance, or to external validation. It’s about embracing who you are, flaws and all, and letting that self-acceptance radiate outwards.

“What made the experience even more special was the way that people connected with the message,” she continues. “Seeing other people find inspiration in my words reminded me how universal the journey towards self-confidence is.”