Inside Oyssey: Co-Founder Darian Kelly on Platform's Features and Where They'll Go Next
When Darian Kelly walked into a new construction sales office as a first-time homebuyer five years ago, a simple question about community demographics led to an uncomfortable silence. “The response I got was, ‘go take a walk and find out for yourself,'” Kelly recalls. This experience, combined with his background in political consulting and supply chain management, would later shape the foundation of Oyssey, a platform he describes as “the Robinhood of real estate.”
Recently making waves for its neighborhood political data feature, Oyssey has emerged as one of 2025’s most talked-about proptech startups. However, the platform’s scope extends far beyond demographics. “We were both young buyers in our early 20s,” Kelly explains, referring to himself and co-founder Huw Nierenberg. “We felt that we didn’t have the right resources when we wanted to buy… We’d wanted to bring the transparency of data to the real estate space like it’s never been before.”
Unlike traditional real estate platforms that primarily serve as lead generation tools, Oyssey distinguishes itself with a three-pronged approach: securing agent commissions, ensuring compliance with the NAR settlement, and providing secure documentation in an enclosed environment. “We’re not just a data platform,” Kelly emphasizes. “We provide a great service to buyer brokers.”
The platform’s approach to NAR settlement compliance represents a significant technical innovation. “Most people on the market don’t even realize this,” Kelly reveals. “We’re creating an individualized ecosystem for each buyer of the agent that’s visiting our platform.” The system automatically documents every property engagement through “click-wrapping” technology, adding each viewed home to the buyer broker agreement in real time.
This automated documentation addresses a growing industry concern. “Right now, people are waiting till the end of a sales cycle, putting in paperwork for a home before they sign their agreement, like the day before,” Kelly explains. “But at the end of the day, the authorities of the industry will catch up, people will get reprimanded, sued. Instead, come to Oyssey, let Oyssey help you take care of it all.”
The platform pairs this compliance innovation with a reimagined showing process. Drawing from their experience with self-guided touring technology at Pineapple, the founders are transforming the traditional open house model. The system uses automated notifications to push self-guided tour opportunities to buyers based on their search parameters, reducing agents’ time spent on showings while maintaining their connection to the transaction.
“What do agents spend the most time doing? They probably spend more time doing tours, driving around their locality, and showing people homes than anything,” Kelly notes. “We’re putting the buyer back in the driver’s seat, allowing them to guide where they want to go.” This approach not only reduces customer acquisition costs for agents but also frees up their time for other priorities.
The platform’s most talked about feature is how it provides buyers with comprehensive neighborhood insights, including income demographics and proximity to amenities, helping them make informed decisions about their future communities. As Kelly explains, “We’re providing the ease that people make autonomous decisions, not decisions shrouded by confusion, misinformation.”
Currently launching in South Florida and New York, Oyssey has ambitious plans for national expansion in 2025. However, Kelly emphasizes the importance of strategic growth. “Timing is everything,” he says. “It’s a matter of making sure that we’re moving strategically and working with local experts to ensure we’re synching up with the people who really need this tool.”
The platform is expanding its partnerships to integrate additional data metrics, including HUD and fair housing APIs, to serve various market segments beyond first-time homebuyers. This comprehensive approach to documentation and compliance could prove particularly valuable as the industry adapts to new regulations.
As the real estate industry navigates significant changes in buyer representation and data transparency, Oyssey’s timing and comprehensive approach position it to potentially reshape how the next generation approaches home buying. While the platform has garnered attention for specific features, its broader vision of empowering both agents and buyers with transparent, compliant tools suggests a more fundamental impact on real estate transactions.
