Cal Spears, CEO of Gambly – iGaming Interviews

Cal Spears, CEO of Gambly, is a seasoned entrepreneur in the iGaming and daily fantasy sports space with a track record of building and scaling influential digital platforms. He currently leads Gambly, an AI-powered sports betting platform focused on streamlining the journey from idea to wager, while also co-founding Third Planet Affiliates, which operates major industry sites such as Props.com and CasinoReports.com. Previously, Spears served as CEO of Better Collective Tennessee, overseeing a portfolio of leading betting and media brands, and earlier co-founded RotoGrinders and PocketFives, both of which became major communities in their respective niches. His career reflects deep expertise in affiliate marketing, product strategy, and user acquisition within the evolving digital gambling ecosystem, with multiple successful exits and leaderships across the industry.

Gambly is positioned at the intersection of AI and sports betting, building tools that simplify and accelerate how users discover, compare, and place wagers through natural language interfaces and real-time odds integrations. The platform’s focus on reducing friction and enabling instant bet execution reflects a broader shift toward automation and personalized betting experiences. This strategy is further strengthened by its recent merger with Unabated, which adds professional-grade analytics, modeling tools, and deeper market data capabilities. Together, the combined approach enhances both accessibility for casual users and precision for advanced bettors, highlighting how AI and data infrastructure are reshaping the future of digital wagering.

You’ve been building in this space since the early days of online poker and daily fantasy sports with platforms like PocketFives and RotoGrinders. Looking back, what lessons from those early communities most shaped how you approached building Gambly?

In many ways, Gambly is the opposite of the earlier projects. My previous co-founders and I had a significant amount of our net worth tied to those businesses.  That made taking chances more difficult, such as bringing on new equity partners or making a significant investment in a new vertical.  Those previous projects and the exits afforded me the chance to take a more collaborative, higher upside approach with Gambly.  

After scaling and exiting multiple platforms and leading operations at Better Collective TN, what made you confident that AI—rather than content or community—would be the next major shift in sports betting?

Bales and I shared a belief that the affiliate model should shift more to retention and incrementality tied to specific bets instead of new player CPAs, especially as the rate of new states adopting sports betting slowed.  We wanted to build a platform capable of sending millions of deep-linked betslips.  AI was the obvious choice – at first, natural language chat focused on betting markets, and soon after, image-reading technology that allowed us to seamlessly turn social parlays into deep links.

Gambly is focused on moving users from the idea of a bet to a placed wager almost instantly. What were the biggest friction points in the traditional betting journey that you set out to eliminate?

Being able to quickly find obscure bets – both odds comps and deep links – was our initial driver.  I remember a friend texting me before the 2023 NFL draft to take a tight end to be the second tight end off the board.  Finding that bet in the DraftKings app took forever, and then I had to do the same on FanDuel to see if they had a better number.  Just asking an LLM for that bet using natural language made much more sense.  Pasting images, articles, tweets, etc., into the chat and getting a contextual betslip was also a secondary driver, but ended up being where we found all of our early traction.

The natural language interface is a major departure from how sportsbooks typically operate. How do you see conversational betting evolving, and what will AI play in shaping that experience?

All activity, including betting, is evolving in thatection thanks to AI.  Sports betting is a particularly good fit.  You can already ask Siri to “text Gambly to give me a betslip for Bryson to win the Masters on Fanatics” and we’ll serve it right up, with an odds comp.  That’s a massively better experience than digging through their app or clicking through filters on popular odds comp sites.  

Gambly has seen strong adoption, from SMS-based betslips to widespread use across Discord communities. What do you think drove that level of traction, and what does it say about how bettors want to interact with tools today?

Converting images of social parlays into deep-linked betslips was instant traction for us.  There are millions of parlays being tailed from hundreds of influencers.  Many of these slips are 10 legs plus.  Before GamblyBot, a follower would have to find each of those bets on whatever site – it could easily take over five tedious minutes to tail a single bet.  With Gambly, the follower just needs to paste a betslip image into chat or call the bot in a reply, wait 20 seconds, and receive a deep link to that exact bet on their favorite site.  

You were already working closely with Unabated before the merger. What made this the right moment to combine forces, and what gap does this partnership solve that couldn’t be addressed independently?

I’m mostly excited to invest more in betting market ingestion, mapping, and deep linking, and row in the sameection on data.  Gambly will immediately contribute time from our AI developers to improve processes while also investing new funds to grow the data team.

Unabated has built a reputation among sharp bettors for its analytics and modeling tools. How do you integrate that depth with Gambly’s simplicity without alienating either audience?

It’s simple – we’ll keep both brands focused on what they do best.  Both brands rely on the data ingestion and will benefit from our previously discussed investment  

As AI becomes more embedded in betting workflows, do you believe it levels the playing field for casual bettors, or ultimately makes markets more efficient and harder to beat?

I think most casual bettors bet for fun and entertainment, and that AI tools will make that process more entertaining for them by reducing frustrations with finding or tailing bets.  Professional and aspirational bettors will certainly benefit from AI – I’m shocked by the number of vibe-coded MLB tools, like home run models, popping up around X this week, for example.  Anyone who wants to build complex systems and tools is now fully enabled.

Looking ahead, do you see platforms like Gambly Ventures becoming the primary interface between bettors and sportsbooks, and how do you position the company to own that decision-making layer?

Yes I see AI-driven platforms becoming the primary interface but the sportsbook operators themselves will also innovate there.  We just need to stay ahead and lean into our strengths.  The actual operators will never be able to offer an odds comp, so we’ll always have an upper hand for sophisticated bettors.  As we develop our personalization tools we believe we can build the ideal home page for any bettor – whether he wants the highest edge Tennis bet or the most entertaining 100-1 first basket parlay, we can have it waiting for him on his morning visit.

Thank you for the great interview, readers who wish to learn more should visit Gambly.