To a passerby, Rip Cathcart looks exactly as one might expect a real estate magnate to look. At 6’5”, he cuts quite a silhouette, and it’s easy to imagine him driving a hard-line negotiation, dwarfing a cold, wooden boardroom. Today, though, the boardroom in the stylish Cathcart Properties office at The Reserve at Belvedere is occupied so I have an opportunity to see Rip Cathcart in a different context.  He invites me into his own office, a soft, comfortably sprawling space with live ivy vines lazing on the walls. It’s the first office I’ve stepped into that is a comfortable temperature, especially this summer when the air conditioning can get polar. The window is open. 

Cathcart is not, as his stature and status would suggest, intimidating. In fact, he’s downright friendly. Across his desk, he fiddles with a cochlear device, an accessory made necessary by an early-onset hereditary problem with his hearing, while he explains how he made it to Charlottesville. 

Unlike most local businesspeople, Rip Cathcart’s story is not one of homecoming. Originally from Pennsylvania, he had planned to settle in Montana, but found the distance from his family too taxing. He was looking at Asheville when Charlottesville popped up on his radar. The town was “very much an objective decision” for him, “the right business climate” that “met business needs but also personal desires, in terms of being in a smaller town and being able to have a farm.” And Rip and his wife do have a farm — 90 acres near Carter’s Bridge, where the magnate de-stresses by spending time with the birds, including pigeons and peacocks, that he raises on the property. It’s easy to understand why Cathcart’s properties have such careful attention paid to their green spaces; this is a man who really loves nature, and rather than incorporating nature into his developments, he incorporates his developments into nature.

“I have over 400 birds,” he says, “but only three give me a hug every day,” Rip says, referring to his three emus, Floyd, Mabel and Gladys. 

Rip grew up outside of Philadelphia and attended the University of Montana, where he studied geology but struggled with whether he was “cut out to be a scientist.” The men in his family were businesspeople, many in the insurance industry, but that didn’t feel quite right. And then, he read a book, Mark Haroldson’s “How to Wake Up the Financial Genius Inside You,” which describes the ins and outs of apartment investing in plain terms. Rip was attracted to the idea because it made sense and it “didn’t feel like a get-rich-quick scheme.” (He later mentions that the return on investment he sees now comes from projects started a decade ago.) If geology didn’t really play to his strengths, real estate and acquisition seemed like a perfect fit. So perfect, in fact, that the young Rip Cathcart dropped out of college. “I would have liked to have finished,” he says, “because I like the idea of finishing what I’ve started. But the reality is that I couldn’t sit still in the classroom because I was so excited about starting this… plan that I had.” 

And start the plan he did. He “mapped out what he wanted to do,” and he’s still doing it. First acquiring real estate licenses in Montana and then Charlottesville, and using Haroldson’s strategy, Rip amassed 31 units over a 10-year period from the early ‘80s to the early ‘90s, and that was the “springboard into developing.” 

Of Charlottesville, Cathcart says simply, “We’re lucky to live here.” His business judgement of the town was certainly sound; this much is obvious even to a real estate novice. The growth that the city of Charlottesville and the University have experienced since the early ‘80s is nothing short of incredible, and the Cathcart Group has been very much a part of that development. 

The plan college-aged Rip laid out never included developing, but when it came time for him to move beyond duplexes and townhomes, he ran into “stroke of luck,” disguised as a pretty major roadblock: nobody would sell him a large property. 

“I realized that if I was going to be a player, I was going to have to develop.” And he hasn’t just developed; Rip builds communities that redefine apartment living or, as he says, “redefine the high end.” The pools and fitness centers are resort style, instead of checklist fulfillers; the communities have ample green spaces, luxurious clubhouses, and friendly, attentive staff. “Our rents are the same, or a little more, but residents feel like they really get something for the money.” Their properties’ popularity with residents is pretty obvious: they’ve swept the Daily Progress’s People’s Choice awards for five years running. With three neighborhoods in Charlottesville (The Reserve at Belvedere, Carriage Hill Apartments, and Rip’s first-ever development, Lakeside), Cathcart Properties consistently deliver exemplary units and manage to make them feel like home. 

Maybe that’s what makes Rip Cathcart (and his properties) different from the standard apartment living: he’s a developer, not a bulldozer, building neighborhoods instead of concrete shelters. We chatted for a while after concluding our formal interview, and I got around to something that I’d been wondering through the whole interaction. “I have to ask — how did you end up with ivy everywhere?”

“Oh,” he said, laughing, a big hand waving towards the vine-adorned walls, “I just like to watch things grow.”