Built on CareExploring and celebrating the place we all love to call home.
VOL. 307 / Built On Care
Meet this week’s guest editor, Penny Simpson Stein. As co-founder of CARE360, a Virginia-based social venture rooted in Richmond and Charlottesville, Penny is helping empower leaders to navigate a rapidly changing future shaped by AI, sustainability challenges, and social transformation. Through CARELab, CARE360’s educational initiative, she and her team are helping prepare the next generation of leaders, innovators, and changemakers through responsible AI, creativity, and human-centered leadership.
After a career leading innovation and product development teams for a Fortune 100 science and technology company, Penny shifted her focus toward building organizations and initiatives that create meaningful community impact. Her work has ranged from helping revive a woman-owned small business, to building a STEM program for a startup school, to supporting the Science Museum of Virginia and its growing environmental and educational initiatives.
After several career pivots, Penny thought she and her husband were entering an early “second act” focused on family, travel, and leisure. But as the mother of three next-generation children, she found herself drawn toward a bigger question: how do we help prepare young people to thrive — not just professionally, but as thoughtful, ethical, and deeply human leaders in an AI-driven world?
That question gained momentum after Penny met her cofounder, Dr. Ira Kaufman, at a local Encorepreneur event, where they discovered a shared passion for helping the next generation navigate a rapidly changing future. Together, they cofounded CARE360 and CARELab — an effort Penny often describes as a kind of love letter to the next generation and the future they will inherit.
CARELab focuses on helping late high school and college students unlock AI as a strategic thinking partner that expands creativity, innovation, and problem-solving. Students work alongside entrepreneurs, business professionals, and civic leaders to tackle real-world community challenges while strengthening the human leadership skills needed to guide technology wisely and create positive impact.
This July, CARELab will host two immersive summer studios, one at the University of Virginia and the second at the University of Richmond, for students interested in leadership, innovation, responsible AI, and social impact.
We’re excited to have her join us this week to share a few of her favorite Richmond discoveries.
Take it away, Penny…
The Green at the Science Museum of Virginia
If you work or live near the Science Museum of Virginia, I highly recommend taking a lunch break or afternoon walk around The Green. Let’s face it — Scott’s Addition is one of the coolest and fastest-growing parts of Richmond, but it has limited greenspace. In a world increasingly shaped by screens, speed, and constant stimulation, these kinds of community greenspaces are becoming more important than ever.
The Science Museum has already transformed portions of former parking lots into vibrant public greenspace and ultimately plans to convert more than 20 acres of its campus into native landscapes, gathering spaces, outdoor learning environments, and places for exploration and connection. Best of all, it’s free and open to everyone — you don’t even need a museum ticket to enjoy it. I honestly imagine The Green becoming something like Richmond’s own version of Central Park.
One of the things I love most about Richmond is that innovation here often starts at the grassroots level. I’d encourage Richmonders to explore our growing community composting movement through organizations like Compost RVA, which provides residential and business pickup services and community drop-off options across the region. Many people don’t realize how much food waste can be diverted from landfills and transformed into nutrient-rich compost that supports local gardens, farms, parks, and greenspaces.
Did you know that food waste makes up about 24% of material in landfills and is one of the largest sources of methane emissions — a greenhouse gas far more potent than carbon dioxide in the short term? Richmond’s composting movement is a simple but powerful example of circular thinking in action: turning waste into a community resource while strengthening our environmental ecosystem. I love that Richmond is embracing this kind of practical, community-driven innovation!
Vitals: Compost RVA / Residential + Business Composting Services / Community Drop-Off Options
Experiences That Prepare Students for an AI-Driven Future
One of the best investments we can make as a community is helping young people prepare for a world being rapidly reshaped by AI and technological change. We’re entering what I often think of as the AI-Humanity Paradox: as technology becomes more powerful, uniquely human capabilities like empathy, ethics, creativity, collaboration, and critical thinking become even more important.
That’s why I’m passionate about programs like CARELab, which help students strengthen leadership, adaptability, innovation, and purpose-driven thinking alongside technological fluency. This summer’s CARELabs at the University of Richmond and University of Virginia will bring together students, entrepreneurs, business professionals, and civic leaders to tackle real-world community challenges while exploring responsible AI and human-centered leadership.
CARELab partners with the University of Virginia Contemplative Sciences Center and the University of Richmond Innovation Studio to provide immersive, intergenerational learning experiences for late high school and college students. Through the program, students work alongside entrepreneurs, business professionals, and civic leaders while developing leadership, collaboration, strategic creativity, and responsible AI skills. Students also tackle real-world community challenges provided personally by city mayors.
CARELab studios combine human-centered leadership and mindfulness, entrepreneurship and innovation, responsible AI and prompt engineering, sustainability and social impact, design thinking, and team collaboration and public speaking. Students leave with stronger confidence, expanded leadership capability, and a deeper understanding of how to use AI and innovation to create positive impact in both career and community. Limited partial and fully sponsored seats are available!
There's still time this summer for a road trip, with a twist. Whether you're seeking mountains or sea, Richmond sits in close proximity to some the best day trips in all the land. We recommend picking a spot with Richmond roots. To get you started, we've rounded up three unique destinations just out of town that were inspired by fellow Richmonders.
Windswept Experience & Supply Co.
Many Richmonders know Craig Dodson, the former executive director of Richmond Cycling Corps, for operating the nation’s only competitive cycling program for youth living in public housing and his dedication to breaking young people free from the cycle of systematic poverty. Today, Craig can be found in Irvington where he has channeled his love for bikes, adventure, and community into Windswept Experience & Supply Co. He recently revamped an old garage into a one-of-kind space for curated apparel, bicycle sales and rentals, bike service, paddle-board sales and rentals, long board skate sales, vintage accessories, and more. We recommend making the short drive from Richmond to check out Craig’s new venture, rent a bike or paddle board, and explore the bay, river and creeks. Irvington has two nationally recognized inns, beautiful creekside rentals, gorgeous sunsets, and some of the best eats around at nearby Adrift.
In 2015, Richmonders Ted and Katie Ukrop opened Quirk Hotel, a 74-room boutique hotel (plus art gallery, restaurant, and rooftop bar), in downtown Richmond in an Italian Renaissance building that once was a department store. Today, they’ve expanded their concept to Charlottesville, just an hour drive from RVA, where Quirk occupies a space built around two historic homes on West Main St in the downtown area. Just like the Richmond flagship, Quirk Charlottesville is styled in minimalist contemporary design and art from local artists can be easily spotted around the hotel’s pristine grounds. And like its sister property, the Cville version of Quirk boast an impressive rooftop bar and lounge. Not to mention an expansive barrel aged spirits bar, Bobboo, featuring private reserve and locally distilled whiskeys and spirits. Schedule a stay, stroll the nearby Downtown Mall, rent a kayak from Rivanna River Company, and get inspired at Ix Art Park.
Skip the crowded beaches and head straight to charming Cape Charles on the Eastern Shore where Richmond’s very own local entrepreneur David Gammino, along with co-owner Kathryn Gammino, has lovingly renovated a historic building within walking distance of Cape Charles Beach into what is today known as Hotel Cape Charles. Chesapeake-facing Cape Charles is ideal for those seeking a relaxed pace, small-town vibes, and coastal beauty. We suggest booking a room facing the courtyard at Gammino’s boutique hotel and renting an electric golf cart form the front desk (the entire town is golf cart friendly) right away! Once you’ve settled in, consider an eco-tour to the wildlife refuge just a few minutes away, grab some freshly baked goods and sandwiches to-go from Coastal Baking Co, or take your cart for a spin to Cape Charles Brewing Company where you can sit outside sipping on local brew while enjoying live music.
Represent Richmond when you're on the road with our comfy cotton t-shirt emblazoned with a hand-drawn design. Yes, that's Richmond's airport code. We consider this tee perfect attire for traveling over the holiday weekend or enjoying a lazy day off. Trust us — it's so super soft, you'll be wearing it everywhere.
Meet this week's guest editor, Paul Trible. As many Richmonders know, Paul is the co-founder and CEO of Ledbury, a luxury shirtmaker and menswear brand that has been on fire since 2009. A Virginia native, Paul launched Ledbury in Richmond with his good friend, Paul Watson, after apprenticing under a master shirtmaker in London. Together, the two set Ledbury's businesses strategy, leading to rapid growth and loyal customers here in the River City and far beyond. Paul is joining us today with three tips for venturing out while social distancing. As he puts it, "trying something new might make you feel right at home again...but not at home...again." Take it away, Paul!
Hardywood Virtual
Tasting Panel
Each weekend, our friends at Hardywood Park Craft Brewery host a virtual beer tasting panel. Even though you’re socially distant, you can still drink great beer with your neighbors. Sign up for a weekend session, and beer is dropped off on your front stoop. Who doesn’t want to try a Bourbon-Barrel-Aged Belgian Quad blended with an Apple-Brandy-Barrel-Aged Imperial Stout fermented with figs? No tapped kegs or socially distanced lines. This is one Zoom meeting you will want to attend.
It’s a Ledbury tradition to host our Hunt/Gather Field Party at Orapax, a beautiful hunting preserve just outside the city. It’s a special place as it gives you the sense that you’re in the hills of Charlottesville, without the drive. There’s a fully stocked pond where you’re able to fish from the shore or rent a boat. It’s the perfect place to fish (think 7-lb bass), hunt when in-season, or take your family for an afternoon picnic on the hillside.
As of today, Virginians will be mandated to wear a mask when in public spaces. We at Ledbury have always tried to make your wardrobe fit better and feel better, so our masks follow "suit." Buy one, and we'll donate one to non-profits in Richmond to protect our city's most vulnerable. We recently released our "Love is Why We Wear Them" video featuring friends and family from the neighborhood. Check it out (you might see someone you know), and help our community spread the love, not the virus.
Hand-illustrated letterpress charts detailing flora and fauna native to the Commonwealth of Virginia by The Wild Wander now available at Grid Supply Co.
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