jili tutorial

Matt Bresler Went From Fossils to Parlays, Now Teams With Former DraftKings Data Chief to Lead Odditt

By jili tutorial · August 31, 2026

Matt Bresler Went From Fossils to Parlays, Now Teams With Former DraftKings Data Chief to Lead Odditt

From a Shark Tooth to a Sports Betting Startup

Matt Bresler was on a family vacation in Charleston when he spotted a giant shark tooth for sale at the historic City Market. That moment sparked a deep fascination with fossils, eventually leading to a seven-year career in the international fossil trade. Bresler brokered the sale of complete skeletons to collectors worldwide, saved up enough capital, and used it to bootstrap his next venture: Odditt.

Today, Odditt provides parlay construction and discovery infrastructure for sportsbooks, prediction markets, and daily fantasy sports platforms. Finding that shark tooth was a great start, but meeting Elaine Milardo proved even more valuable. Milardo was the first data hire at DraftKings, where she built the data organization to over 100 engineers and left as VP of Engineering for the data platform. She joined Odditt as co-founder and CTO in 2024.

With Bresler as CEO and co-founder, Odditt has reached critical mass in parlay solutions:

The company recently signed a deal with Amelco, whose platform includes Flutter, Entain, Hard Rock, and Fanatics. Another partnership with Optimove will embed Odditt’s bets into operators’ player messaging. In November last year, Odditt also launched Betflow, a consumer-facing product that lets users discover and place parlay bets in a unique way.

Exclusive Q&A: Matt Bresler on Fossils, Milardo, and the Future of Betting

In an exclusive interview with CasinoBeats from his Las Vegas home, Bresler shared insights on his past, his partnership with Milardo, and his vision for the industry. The conversation has been edited for brevity and clarity.

The First Fossil Sale and Lessons Learned

CasinoBeats: How much did you make on your first fossil sale?

Matt Bresler: I remember selling the first one on eBay for about $10. It blew my mind that I could earn money online doing something I was truly passionate about. Looking back, if I were to run that business again today, I’d take a much more tech-driven approach.

Betflow: Consumer Insights vs. Sportsbook Solutions

CB: What did you learn from running a consumer-facing product like Betflow that you couldn’t learn from selling parlay solutions to sportsbooks?

Bresler: You get direct insight into user behavior—what they scroll past, what they linger on, what they click. Our thesis is that people want parlays, but sportsbooks often suppress parlay volumes. If we create a smooth, frictionless experience, we believe users will place many more parlays. Betflow has confirmed that directly.

CB: How has Betflow grown in its first year? How many users and bets have been explored?

Bresler: Millions of bets have been explored—we’re approaching two million. The user base is still small because our focus has been on technology and product. We’re now partnering with companies that excel at marketing and user acquisition to scale Betflow further.

Competitors and the Status Quo

CB: Who do you consider Odditt’s biggest competitors today?

Bresler: Our biggest competitor is the status quo—manual parlay construction. Doing it manually means you can only offer thin coverage and show the same thing to everyone. Many sportsbooks simulate a good product experience, but users quickly become distrustful when they see only 20 parlays that are identical for everyone, and then find none linked to individual events.

What True Innovation Looks Like

CB: Innovation is often a buzzword. What does it mean to truly innovate in this industry?

Bresler: True innovators ask, “What’s next?” We focus on that because the same basic bet types have existed for a century. The only real advancement has been better algorithms and the ability to combine selections within the same game. We strongly believe that’s not the final frontier.

The Partnership with Elaine Milardo

CB: Tell us about your working relationship with Elaine. She was an OG in data at DraftKings, right?

Bresler: Absolutely. She was the first data hire there and ran the entire data team from inception through post-IPO. Elaine and I work perfectly together—we balance each other out. I push product forward, and she turns ideas into reality. The first three years of Odditt, I was a solo act and couldn’t get much off the ground technically. Now I’m on the front line, and she ensures we execute across technology and operations. It’s an invaluable partnership.

Personalization and Responsible Betting

CB: Any new initiatives or product enhancements you’re working on?

Bresler: Personalization is a big focus. We’ve partnered with Optimove to launch personalized emails with embedded story-driven bets and parlays. We’re also rolling out personalization in our sportsbook widgets.

CB: What does that entail?

Bresler: In the first phase, we deliver high-quality, scalable content that can be placed anywhere—prepackaged parlays on any surface. Users can filter these themselves. In the next phase, when a user opens the widget, they’ll already see content tailored to them.

CB: There’s a fine line between making betting more accessible and more addictive. How do you navigate that?

Bresler: Transparency is key. We show historical data rather than hiding behind probabilities and expected value. At the right scale and with responsibility, this isn’t addictive—it enhances the sports viewing experience. It’s actually healthier because it makes the value clearer. If you enjoy choosing the bet itself, it takes pressure off needing to win.

How Odditt Changed Bresler’s View of Sports

CB: Has building a company around betting data changed how you personally look at sports?

Bresler: When I started, I focused on in-game models, algorithms, and exploiting odds. But I’ve learned that both insiders and outsiders over-index on winning. Of course you want to win, but most people won’t—and that’s okay.

Expanding into New Leagues and Sports

CB: What are Odditt’s newest offerings for leagues, and what’s next?

Bresler: We made a big push around the World Cup, adding about 10 to 15 tournaments including international play. We’ll keep expanding in-play and pre-match offerings. Expect tennis, rugby, and cricket within the next 12 to 18 months.

Five-Year Vision for Sports Betting

CB: Where do you see the industry heading in the next five years?

Bresler: We’re pioneering a shift in how people choose bets. Looking at other gambling forms like casino, the mechanics of selection are about to explode. That’s why we’ve built more gamified, entertaining, frictionless parlays—including a first-of-its-kind emoji-to-parlay converter. The question will change from “What am I betting on?” to “How do I get there?” That’s what the industry isn’t thinking enough about, and that’s where it’s going.