A decade before Reid Rooney began assembling a collection of fantasy-football subscriptions, Chicago sports coverage and golf data, he was a college baseball player with a wonderfully specific claim to expertise. He had played in the Mid-American Conference at Central Michigan. That did not make him the oracle of college football. It did mean he watched the MAC more closely than most people. If a stranger wanted insight on Central Michigan, Rooney reasoned, the useful expert might be the person with a narrow, lived edge - not the loudest person on television.
That distinction became the first brick in Betsperts. The platform launched in 2018 as a social community where bettors could post picks, track records and find people who knew a conference, team or kind of wager particularly well. The scoreboard mattered because the internet’s sporting sages had long enjoyed an occupational perk: selective memory. A tracked record gives boasting a chaperone.
Betsperts has since become something broader and more interesting. Rooney and co-founder Austin Harper now run a group of specialist sports-media properties: 4for4, Dynasty League Football, Bleacher Nation, Bleacher Nation Fantasy, Betsperts Golf and Fantasy National. What started as a place to prove a pick has evolved into a thesis about media itself. In an era of abundant clips, summaries and borrowed traffic, Rooney believes the durable asset is the group of people who return on purpose.
“Fantasy players and sports bettors want to be part of a community.”Reid Rooney, 2024
The baseball player and the tool cabinet
Rooney comes from Chicagoland. At Central Michigan, he played for the Chippewas and earned a master’s degree in entrepreneurship. The combination sounds almost too tidy in retrospect: competition in the afternoon, company-building in the classroom. After college, he deliberately joined a company of roughly ten people in a sales role. He wanted to see entrepreneurship without the comforting distance of a case study.
Then came the opposite scale. At Stanley Black & Decker, Rooney managed about $200 million in annual sales and met Harper. The pair absorbed a lesson that had little to do with drills and saws. A customer walking onto a construction site did not meet one universal mega-brand. The company offered distinct brands and tools for particular jobs, united behind the scenes but legible at the shelf.
Years later, that tool cabinet became a metaphor for Betsperts. One sports fan needs draft rankings. Another wants year-round dynasty strategy. A third wants Chicago reporting. A fourth has willingly surrendered a Sunday afternoon to the mysteries of strokes gained. The portfolio does not ask all of them to pretend they are the same customer.
The elegance of the model lies in what stays separate. Rooney is not trying to repaint every acquired property in Betsperts green. Each brand keeps a recognizable promise. Behind the curtain, the group can share operating knowledge, technology, advertiser relationships and a wider map of sports consumers. Out front, the fantasy obsessive still walks through the door marked fantasy obsessive.
A rollup with house rules
The acquisition run began in earnest in 2021. Betsperts acquired Matthew Berry’s Fantasy Life App, adding a large social community for fantasy players. That August, it announced a $6 million Series A led by HBSE Ventures and Verance Capital and acquired 4for4, a subscription research and analysis business. Dynasty League Football followed, then Bleacher Nation, the Chicago-born sports publisher. In July 2025, Fantasy National Golf Club became deal number five.
Rooney’s public acquisition filter is admirably concrete. He looks for profitable businesses in roughly the $1 million to $10 million revenue range, with useful traffic, tools or technology that add rather than duplicate. Yet the non-negotiable is less easily placed in a data room: a retained, engaged community.
This produces an unusual post-deal instinct - patience. Longtime subscribers have helped shape a niche property through years of requests, complaints and renewals. They possess what Rooney calls sweat equity as customers. Change the name, price and cherished features on Monday morning and a buyer can discover, with astonishing efficiency, which parts of the company were load-bearing.
There is also a useful humility in this posture. An acquirer may understand finance, distribution and code while knowing less than a ten-year subscriber about why the product matters on a rainy Tuesday in November. The regulars know which newsletter gets opened first, which annual feature starts arguments and which supposedly minor toggle prevents a small domestic crisis on draft night. Rooney’s method gives that local knowledge a seat at the integration table.
Rooney says Betsperts tries to meet power users, listen to the existing team and understand the culture before introducing operating changes. When users resist, he favors direct explanation: what is changing, why the business needs it and how it will support the product. Transparency will not make every critic cheerful. Sports fans can detect cheerfulness and stamp it out before lunch. It does, however, treat criticism as participation rather than noise.
In a community acquisition, map the rituals before the revenue synergies. Identify power users, protected features, inherited pricing and the language insiders use. The product has a history even when the spreadsheet does not.
The quiet arithmetic of loyalty
Media companies are excellent at celebrating crowds and less practiced at asking whether anyone came back. Rooney is interested in the second question. Betsperts earns money through advertising, affiliate relationships, fantasy games and subscriptions. Of those, he has spoken most warmly about subscriptions in the near term because renewals create something precious in a volatile industry: a revenue line with a memory.
Affiliate economics can swing with operator budgets, regulation and the race for market share. Search and social platforms can change how traffic arrives. A subscriber who finds a ranking tool useful every football season is different. In a 2025 interview, Rooney discussed annual subscriber retention in the 80 to 85 percent range. A smaller community with that habit can be worth more than a huge audience that passes through once and forgets the address.
His view of creators follows the same logic. Audiences often form relationships with the writer, host or analyst rather than the corporate sign over the studio. If that person moves, listeners may follow. Brands therefore have to invest in both the personality and the community around the personality, not behave as if the distribution channel produced the affection.
“We actually intentionally stay under the radar a bit.”Reid Rooney, on executing Betsperts’ plans
Under the radar does not mean without scale. By spring 2022, Rooney said the group had expanded from five employees and one app to 40 employees in five countries. Its properties had produced more than 10,000 articles and nearly 1,000 streams and podcasts in the prior year, while its apps recorded 36 million sessions. By 2025, he said the company had raised more than eight figures in capital and was profitable.
The better clue to his temperament may be the way he talks about golf. Rooney is devoted to Flossmoor Golf Club near Chicago - “no, it’s not a dentist club,” he has joked - and has praised Cabot Cliffs and Sand Valley. Golf is leisure, obsession and now a serious business vertical. Betsperts Golf began with content and proprietary tools; Fantasy National added a long-established analytics product and community, with co-founder Pat Mayo joining the expanded effort. Rooney has described an ambition to make the combination a broad destination for golf bettors and fantasy players.
A portfolio built for the return visit
Rooney’s tastes remain cheerfully Chicagoan and slightly masochistic in the traditional sporting way: the White Sox are his baseball club. Tottenham is his football club. He travels when he can, has embraced Canadian culture through his Canadian wife, and has named living in London as a life goal. These are not decorative facts. They help explain a business built on the idea that fandom is identity, routine and conversation before it is a conversion funnel.
Betsperts still cares about data. Its first product was designed to make records accountable, and the current portfolio includes models, rankings and analytics. But Rooney’s larger bet is that numbers become more useful when people have a reason to gather around them. A golf model without a community is a calculator. A dynasty ranking without argument is merely a list. Sports become sticky through the pleasure of being right together, or at least being wrong in excellent company.
The company’s next chapter is likely to contain more acquisitions, more subscription products and a patient eye on U.S. iGaming. The exact collection may change. The filter sounds settled: find a useful niche with a living community, preserve the peculiar thing that makes people care, and add enough support to help it grow.
There is a modest business idea hiding inside that strategy. The internet does not suffer from a shortage of information. It suffers from a shortage of places worth returning to. Rooney has spent eight years trying to build those places for sports fans, one specialized front door at a time.