Jacob, or “Jake” Hamilton grew up just a few blocks from where he now lives with his wife, Claire, and their beagle, Greg, in the heart of Del Ray. His childhood was marked by a knack for enterprise. “I started mowing lawns for the Yates family before school and eventually subcontracted snow-shoveling jobs to my friends,” Jake would recall with a grin. In 2009, Jake and his siblings launched a lemonade stand that not only outshined others in the neighborhood but also won ‘Best Lemonade Stand in America’ by Inc Magazine. “We had the most popular stand on the block,” he said, a hint of pride in his voice.

As a teenager, Jake juggled work for several Alexandria businesses, but his favorite job was with Brett Rice at Arlandria Floors. (*) “That’s where I first learned the value of craftsmanship and a hands-on approach,” he explained. Jake opted to skip college, choosing an entrepreneurial path that would shape his career in real estate and remodeling. By the time he founded Character Companies in 2019, Jake had already gained years of experience in property speculation, remodeling, and investment. “Helping homeowners make smart remodeling decisions is the core of what we do,” he said.

Jake’s personal life took a turn in 2021 when he met Claire on Hinge, a dating app. Claire had just graduated from the University of Virginia and moved to Alexandria. “Our first date was at Vola’s in Old Town. We talked for hours,” Claire shared. A few months later, Jake spotted a fixer-upper house while driving through Del Ray and placed an offer on it. By 2022, the couple moved in together and began renovations. “It wasn’t just about the house,” Claire said. “We fell in love with our neighbors, too. It felt like home right away.”

The couple tied the knot in November 2024 at King Family Vineyards in Charlottesville. “There’s a tradition in Virginia where you bury a bottle of bourbon at your venue to guarantee clear skies,” Claire explained. “Jake’s a bourbon fan, and I’m a planner, so we couldn’t resist.” The tradition worked. The chilly November air and clear skies made for stunning wedding photos. “Our first dance was to ‘Sun to Me’ by Zach Bryan,” Jake added. “It’s one of our favorite songs.” Their beagle, Greg, served as the ring bearer, charming everyone by napping at the front of the aisle during the ceremony.

For their honeymoon, Jake and Claire ventured to Thailand, a first-time trip to Asia for both and a major bucket list item. They spent two weeks exploring Bangkok, Chiang Mai, and Krabi. “Feeding elephants at the Elephant Retirement Park was unforgettable,” Jake said. “They’re such gentle giants, and they loved the bananas and pumpkins we brought.” Claire’s favorite moment was snorkeling at Chicken Island near Krabi. “The water was crystal clear, and the fish were so vibrant,” she said. “It felt like a dream.”

Back home, Jake and Claire are planning to stay in Del Ray as they begin their next chapter: starting a family. “This neighborhood is special,” Jake said. “I’ve watched it evolve since my childhood. I remember when Pork Barrel BBQ used to be a gas station and when Yates Corner was being built, I watched it get constructed from my middle school classroom window.”

Claire agreed, adding, “Del Ray is perfect for families. It’s walkable, friendly, and vibrant. We love bumping into friends and neighbors while walking Greg to the dog park or one of Jake’s construction sites.” Their backyard fire pit has become a gathering spot for neighbors to share wine and cookies. “It’s moments like those that make this place feel like home,” Claire said.

Character Companies Inc. has made it a priority to support the Alexandria community in meaningful ways. From volunteering to help elderly neighbors in Del Ray with small handyman projects to sponsoring the Alexandria Little League team, the Turkey Trot, and ACHS Athletics, their involvement shows a genuine commitment to their neighbors. It’s clear they value building connections as much as they value building homes.

As Jake continues to grow Character Companies and Claire focuses on coaching at the [solidcore] in Old Town, they are building a life rooted in community and shared dreams. “We feel so blessed to be growing our roots in Del Ray,” Jake said, looking at Claire. “And we’re just getting started.”

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