When did your entrepreneurial interest in fantasy sports betting first originate?
My entrepreneurial interest in fantasy sports goes all the way back to before daily fantasy sports (DFS) was even conceived. My partner from PocketFives Riley Bryant and I had dabbled in quite a few different things. We had a site called Fantasy Fanatics that tried to rank season-long players just based off their ability to answer sit/start questions. We also had an SEO-focused site called FantasyTeamNames.net. I would say a lot of it was trying to find product market fit after PocketFives in an area we were passionate about.
When DFS became an industry, we very early on started thinking about how to recreate PocketFives in that environment. The games in the early days of 2009 were mainly head-to-head games or winner-takes-all. The formats were very basic and the payouts were very low. We got back to work on building a community around who are the best fantasy sports players. In the process of building that, FanDuel launched and started doing live final tournaments with big payouts, and we were just right there ready for it based on the experience we'd had with PocketFives.
How did your relationship with Jonathan Bales eventually manifest into developing Gambly? Was there any prior experience or was this the first project you two had worked on?
I actually heard of Bales when Peter Jennings sent me a link to his book. We got introduced at a live final when he was just a player and before he started doing his own site. We spoke early about potentially working together; none of the ideas quite worked out, but we always liked each other. We were always very friendly competitors and had a lot of respect for each other. Strangely enough, we both ended up selling our companies to Better Collective, went through a non-compete, and it was during that time we started talking about what we could actually do together.
What separates Gambly from sportsbooks like FanDuel or DraftKings and how does AI innovation factor into its operations?
Gambly is all about getting you from the idea of a bet to a betslip loaded for you on any of those gambling sites. We sent 15 million bet slips during football season. These are deep-linked bets to various sites, but the vast majority of them go to DraftKings and FanDuel given they're almost 90% of the market share. Gambly just helps you quickly get to those betslips. One of our stories was when a friend texted me and said, ‘take this tight end to be the second tight end drafted in the NFL Draft, and I said ‘okay, I get that, I'd love to make that bet with you, but how the hell do I find it?’
Our immediate traction was using AI to read an image of a bet slip
On a single bet, it's not that hard to just find it on the site. But if you're wanting to bet a 10-leg same-game parlay that you see on social media, it could take you 10 minutes to find all of those legs. It's a huge time saver to just take a screenshot of the image, drop it into Gambly and 20 seconds later we've sent you a direct link to go make that bet on whatever site you want.
When did yourself and Jonathan first come to learn of Unabated and how did that lead to the merger which formed Gambly Ventures?
I was an investor in Unabated seed rounds, I've always been familiar with them. I had a no questions asked mentality once I saw who the team was. When it came time for Bales and I to start our project, we wanted to find the right data partner. We're talking about comprehensive gambling market ingestion, and Unabated was particularly well positioned to do that. They're already providing a lot of that data in their paywall service and we spoke with them about expanding that odds ingestion. They've been on our cap table since day one.
As we worked more closely together, our businesses just became more and more intertwined. At one point, their lawyer suggested if we had considered merging, and that conversation got more serious over time and then we pulled the trigger on it. It took us about six months to make it happen, but we are very glad we did because it only makes more sense now as we start to look towards prediction markets and see a whole slew of new markets that we'll need to properly ingest.
What type of opportunities will stem from the merger and how will Gambly Ventures offer the best of both companies?
Both companies are going to remain focused on what they already do. Gambly is going to be very mainstream, just helping remove the friction from betting, whereas Unabated is going to be focused on the top 5% of sports bettors. The data which services both companies is where we're going to make our investment. That's where we'll grow in the same direction.
Are prediction markets an avenue you'll be looking to move forward with following the merger, and how do you plan on navigating the current regulatory landscape?
I have no idea what's going to happen. I try to ask every smart person I can what they think's going to happen, but it's clear that prediction markets are going to be a big focus, so it needs to be a big focus for us. We're already ingesting Kalshi, ProfitX, Novig and Polymarket is on the way. Underdog Predictions is also coming very soon. We are going to first get all of the sports offerings within prediction markets ingested because that needs to be mapped to what we're already doing. Even beyond that, we need to start taking political markets, prediction markets on the weather, whatever it is we need to. That's the goal.
Do you see Gambly Ventures having to follow the same regulatory requirements as Kalshi or Polymarket?
Not at all. From what we've seen, we're not going to have to get any types of licences. We can easily be an affiliate of any of these companies, whether it's a cost per acquisition for a new user or some type of profit share on fees. We have had discussions about being an independent software vendor where we could work with one of these companies, they would do the KYC, the account maintenance and hold the funds, but you could actually trade on Gambly instead of their platform. That doesn't need a licence. We haven't seen anything where we're going to have to go through any regulatory hurdles and we want to work with all of these sites, just like Gambly works with all of the sports betting sites. That'll still be our priority.
As CEO of this new enterprise, what are your strategic goals for the remainder of 2026, whether that be new collaborations or expanding your consumer base?
Getting AI involved in every process of our business and making sure everyone on the team is trying to become superpowered by using agentic processes. In terms of products, expanding what Gambly Chat is capable of, getting into questions about trends, historical odds and hit rates. That'll be a big focus of ours soon.