How Rolling Insights is democratizing sports data for builders

Rolling Insights CEO Steven Kenway joined The BettingStartups Podcast ahead of the Canadian Gaming Summit to unpack how his team is democratizing sports data, supporting early-stage founders, and more.

When Steven Kenway left a steady role in Canadian healthcare to start building startups, he knew two things for sure: large, mature industries guard their territory fiercely, and good data is the hidden lever that tilts any playing field.

His first foray was real estate tech—a space he jokes was controlled by a “fiefdom” that fired off cease and desists faster than brokers close deals. Today, as CEO of Rolling Insights, he’s putting those hard lessons to work in sports betting and fantasy sports, where reliable data is still gatekept by official providers with deep league ties and steep price tags.

In Rolling Insight’s mission to “democratize sports data for all,” Kenway believes startups don’t need VIP data to win—they just need accuracy, (enough) speed, and a price point that doesn’t sink the ship. 

As an unofficial data provider, Rolling Insights listens to public sources, automates collection, and pipes stats through an API at what Kenway calls “medium latency” — fast enough for most consumer experiences, and crucially, far more affordable than official feeds.

For early-stage founders deciding whether to shell out for official data or build with unofficial feeds, Kenway puts it plainly: official data buys “the branding and the name and you get a tie to the league,” but “it comes at a heavy cost.” 

That expense is often too large and premature for most upstarts and creators to stomach; at the same time, it underscores where unofficial data providers fit into the ecosystem. Kenway says Rolling Insights will see large, established companies utilizing its feeds in early product development to gauge whether or not they need the official stamp.

This pragmatic balance between scrappy and sophisticated runs through everything Kenway builds. It’s why Rolling Insights isn’t just a data vendor — it’s part data supplier, part consultant, and part startup accelerator.

Breakaway Accelerator—an incubator offering for startups—is a telling example: startups get discounted data for a year, connections to industry experts like Vela Wood and SCCG Management, and a support network so they don’t flame out before they can scale.

“It’s really positioned for startups, new entrants into the market—giving them all the ingredients that they need to increase the chance of their success.”

Kenway says the accelerator program offers mutual benefits, where more successful companies built on its data means more long-term clients for Rolling Insights. “If they're successful, they're gonna keep using our data,” he says. So far, about 30 startups have “graduated” from the program, and around 20 are actively participating in it.

As for the future, Kenway doesn’t rule out Rolling Insights stepping up to become an official provider itself someday. But for now, he’s more interested in making the data game more accessible for underdogs—and watching what happens when thousands of small, creative ideas get the same stats the pros have.

Listen to the full podcast on YouTube, Spotify, and Apple Music.