Golf and grandkids are two fine pillars of retirement, filling plenty of days with leisure and excitement. But for career veterans used to chasing trends, closing deals, and staying in the know, two pillars alone won’t hold. At least, not according to longtime Richmond businessmen Stan Maupin and Gary LeClair, who built a Boomer-focused speaker series around the motto: “Golf and grandchildren are not enough.”
From Boardroom to Boomerhood
When he retired, Maupin, now 75, “wasn’t going to just stay home and not do anything,” he says. A business consultant for Richmond-area entrepreneurs for more than 30 years, he often worked alongside LeClair, a corporate attorney. Together, they founded the Richmond Venture Forum and the Greater Richmond Technology Council.
“We’d always been out there on the evolving edge of things,” says LeClair, 70—and that wasn’t about to stop just because they were getting older. As they neared retirement in the early 2010s, the question turned to: “What’s next?”
That phrase nearly became the name of the group they formed to help Baby Boomers stay connected, informed, and fulfilled in post-career life. Over the pair’s periodic lunches, the idea for their breakfast speaker series gradually took shape, and they eventually landed on the label “Encorepreneur”—a fitting name for a second act (credit to Maupin).
Encorepreneur Takes the Stage
Their first meeting in 2013 was held in Richmond’s Corrugated Box Building, an office space reimagined from a 1920s warehouse in Manchester. Matt Thornhill, founder of the marketing research and consulting firm Boomer Project, was the inaugural speaker. About 60 people attended, but it wasn’t the number that impressed Maupin and LeClair so much as who showed up. Sitting in the front row was Jim Ukrop, Richmond business icon and former CEO of Ukrop’s Supermarkets.
“I thought maybe there’s something to this if Jim Ukrop takes the time to come,” Maupin recalls.
Since then, Encorepreneur has hosted 138 events with speakers of every stripe. One of the largest drew 475 people for a virtual talk and U.S. Capitol tour with former U.S. Representative from Virginia, Abigail Spanberger. Among the most memorable was the late Bruce Heilman, a former University of Richmond president, World War II veteran, and Harley-Davidson rider. He spoke about Iwo Jima, yes, but also about crossing the country on his motorcycle in his 80s.
“He spoke with such quiet confidence and reverence that he got two of the eight standing ovations we’ve had during our time,” Maupin says.
Heilman’s two appearances remain a favorite for both Maupin and LeClair, but truly, the list of standouts is long. There’s Rojai Fentress, wrongly convicted of murder at 16 and freed 24 years later, and Richmonder Camille Schrier, who you may know as Miss America 2020. Topics have ranged across life experiences, religion, health, current events, business, technology, the arts, and broader questions of “what’s next”—whether that’s artificial intelligence, cryptocurrency, or reality TV.
And still, the well hasn’t run dry. “I’m an ADD guy, procrastinating and so forth, so usually at the last minute I’m trying to find somebody,” Maupin admits. “After 130 speakers, you run out of your friends, and you really are stretching, but it just happens.” Ideas come from associates, suggestions, or simply walking down the street and noticing the world at work.
Beyond the Podium
From the beginning, Encorepreneur has been about learning—and not just from the speakers. Maupin recalls advice he once got: Take a different route home now and then, just to see your environment from a new angle. He carried that idea into the group, holding events at nearly 70 venues across Richmond and its suburbs—mosques, funeral homes, synagogues, theaters, libraries, police academies, high schools, arts centers, even Tang & Biscuit, a short-lived Scott’s Addition biscuit joint (because Maupin had been eager to try). Only the pandemic’s Zoom stint put the tradition on pause. These days, he says he gets more venue recommendations than speaker ideas.
At one early meeting, LeClair encouraged attendees to download the navigation app Waze—a small act that foreshadowed big possibilities.
“Baby Boomers are not a finished product,” LeClair says. “We’re continuing to evolve. Part of that is getting out of your comfort zone—physically, mentally, spiritually, work-wise. Learning to download an app, going to a location you’ve never been before, walking into a room with a couple hundred people that you really don’t know.”
Colloquially, Encorepreneur might be referred to as a networking group, but LeClair disagrees. “It’s really not networking, it’s more friendship. There’s no handing out business cards or that stuff—most of us are long over that. If you go, you’ll see a bunch of hugs.”
Those friendships have fueled adventures far beyond monthly meetings. In spring 2024, Maupin chartered two buses to take members to South Carolina for the solar eclipse. They’ve staged an art show for Encorepreneurs-turned-painters, and Maupin is eyeing the possibility of a Battle of the Bands for musically inclined retirees dusting off old guitars.
Crucially, LeClair says, “it’s an open community.” While the group is geared toward Boomers, people of any age or background are welcome. All that’s required is a name tag—“in very big print because we can’t see very much,” LeClair jokes—and a willingness to listen and learn.
“Life gets better every year if you continue to learn,” LeClair says.
This article originally appeared in the December 2025 issue.
