Underdog Fantasy

High-Level Overview

Underdog Fantasy is a fantasy sports and sports betting platform founded in 2020 that builds innovative gaming experiences for sports fans, primarily through Best Ball tournaments, Pick'em contests, and a proprietary sportsbook.[2][3] It serves casual and hardcore enthusiasts across 40 U.S. states, Washington D.C., and Canada, solving the problem of time-intensive traditional fantasy leagues by offering no-management drafts, player prop predictions, and seamless betting integration, with revenue from 10-15% contest fees and projected $500 million in 2025 revenue.[2][3] The company's growth momentum is rapid, fueled by proprietary tech, AI-enhanced support, and expansions like Crypto.com prediction markets in 16 states as of September 2025, earning it #3 U.S. startup ranking by LinkedIn.[2][3][5]

Origin Story

Underdog Fantasy was founded in 2020 by Jeremy Levine, Brandon Stakenborg, and Trevor John, who brought expertise from prior fantasy sports ventures like StarStreet and DRAFT.[2] The idea emerged to reimagine fantasy sports with less time-consuming, more engaging formats amid a market craving alternatives to season-long leagues, quickly achieving product-market fit via flagship Best Ball tournaments that auto-optimize lineups.[2] Pivotal moments include launching a proprietary sportsbook in North Carolina in March 2024, expanding to prediction markets in 2025, and hitting transformative growth despite industry disruption, as noted by CEO Levine.[2][3]

Core Differentiators

Underdog stands out in the crowded sports gaming space through proprietary technology and innovative formats:

• Innovative Products: Flagship Best Ball eliminates weekly management with auto-lineups and massive prizes (e.g., $15M Best Ball Mania pool); Pick'em offers "Higher/Lower" player props combinable like parlays; unique additions like Battle Royale and Crypto.com prediction markets.[1][2]
• Proprietary Tech Stack: Built in-house (not white-label), using cloud infrastructure, JavaScript, Python, TypeScript, Material-UI, Sentry for monitoring, and AI tools like Fin for 80% deflection in customer support during peak events.[1][2][4][5]
• User Experience and Community: Seamless integration across fantasy, betting, and media (e.g., YouTube shows like The Arena); fosters loyalty via social/gaming blends, remote-first culture with "startup energy," and fan-first content with athletes/analysts.[1][3][6]
• Speed and Scalability: Rapid innovation in 40+ markets, state-of-the-art tools like Cloudflare and Braze for engagement, enabling quick adaptation in fast-paced sports tech.[1][3][4]

Role in the Broader Tech Landscape

Underdog rides the wave of sports entertainment digitization, blending fantasy, betting, prediction markets, and media amid U.S. legalization trends and fan demand for interactive, mobile-first experiences.[2][3] Timing is ideal post-2020 expansions in sports gaming, where proprietary tech gives it an edge over white-label competitors in DFS, props, and sportsbooks, while AI scales real-time support for volume spikes.[2][5] Market forces like community-driven retention and niche formats (e.g., no-management play) favor its growth, influencing the ecosystem by setting standards for engagement—e.g., cultivating loyal communities and innovating beyond traditional leagues, as the only top-tier operator on custom tech.[1][3][8]

Quick Take & Future Outlook

Underdog's trajectory points to dominance as the U.S. sports gaming leader, with proprietary tech enabling further products like expanded prediction markets and media networks to capture more fan engagement.[3] Trends in AI personalization, regulatory openings, and social sports gaming will propel it, potentially scaling beyond $500M revenue through international pushes and deeper crypto integrations.[2][3] Its influence may evolve from disruptor to ecosystem shaper, redefining fun, accessible sports play for millions—proving that blending passion, people, and product builds the biggest platforms.[3]