Betting on product to win in fantasy sports

Executive overview

Jeremy Levine built two successful fantasy sports companies and sold them strategically, then founded Underdog to capture a massive untapped market. The key insight: American sports fans engage differently than global consumers—they're player-focused, game-obsessed, and primed for novel formats that traditional sportsbooks ignore. Underdog succeeded by obsessing over product velocity and design rather than copying competitors.

Core insight: Beating entrenched competitors requires building a fundamentally different game, not a better version of the same one.

The early journey: From sports cards to regulatory battles

• Started collecting sports cards as a kid, dreaming of predicting future value
• Co-founded Star Street (2009) as a sports stock market after discovering similar company One Season
• Bootstrapped with engineers from Craigslist; later entered Techstars
• Pivoted to daily fantasy sports, recognizing early traction in the format
• Navigated existential regulatory risk when 14 state attorneys general declared fantasy illegal (2015–2016)
• Industry united through Fantasy Sports Trade Association to pass clarifying legislation across 20+ states
• New York emergency Senate session at 2 a.m. confirmed legality; tipping point for business viability

Selling strategically and finding the next opportunity

• Sold Star Street to DraftKings (2014) after recognizing they'd outspend any competitor on marketing
• Founded Draft with co-founder Brandon; built Best Ball format (no management required, pure draft skill)
• Sold Draft to Flutter/Paddy Power (2017) at that time the largest fantasy sports exit
• Left Flutter when new CEO changed strategy and forced Draft to merge into FanDuel
• Lesson learned: In M&A, leadership continuity and belief matter more than promises; CEO changes everything

Why Underdog won despite competing against 800-pound gorillas

• Launched Best Ball publicly after Fanduel shut down Draft; saw 1,000+ devastated tweets from fans
• Founding team: 7 people from Draft who knew exactly what to build
• Reached $485M valuation by 2022; now valued at $1.3B with $400M+ revenue (5+ years old)
• Fastest-growing sports gaming company zero-to-five in history
• Hiring for product obsession; every company meeting reiterates: people and product
• Prioritize product velocity above all else, unlike competitors focused on marketing
• Built proprietary tech stack rather than licensing overseas sportsbook software, creating architectural advantage

The American sports consumer is unique

• Over 60M people play fantasy sports; 90M+ do March Madness brackets annually
• Americans invented games to express sports opinions: Survivor pools, Pick'em, Super Bowl Squares, NFTs, fantasy
• Player-focused fandom (LeBron, Giannis) is distinctly American; overseas markets prioritize teams
• Our sports are stop-and-go (football, basketball); most global sports are continuous (soccer, F1)
• Sportsbook products were designed 25 years ago for smoky retail shops, not mobile devices for game-lovers
• Traditional sports betting books treat players as incidental data; Underdog makes players the core

Product wins in the market

• Players can now express player-driven opinions easily on the Underdog app
• Caitlin Clark effect brought 4X growth in WNBA entries; broadening customer demographics
• Marketing focuses on stars in each region (e.g., Luka bump in LA after Lakers trade)
• App design is dead simple—a rarity in sports tech
• Average entry price $13, designed for the fan watching the game, not the gambler
• Launched partnership with Crypto.com for prediction markets—first in category to offer teams legally via federal regulation

Responsible gaming: Building an industry standard

• Created GuardDog fund investing in for-profit responsible gaming tech companies
• Partnered with IDPair to create unified opt-out across fantasy operators (60 days or perpetuity)
• Regular mentorship from ex-regulators and responsible gaming experts
• Philosophy: industry defaults to bare minimum; tech + regulation will keep customers safe
• Transparency on disclaimers and problem gambling resources is table stakes

White space still remaining

• Prediction markets now allow team-picking (unavailable before due to sports betting restrictions)
• Sports betting licenses in additional states will unlock more product offerings
• Regulatory framework now clear after years of uncertainty; can expand offerings at scale