From pioneering subscriptions to tackling AI, James C. Heckman architect reshaped digital media for 30 years, consistently building value through every internet wave.
James C. Heckman is a Media Infrastructure Architect who has defined the business models of the commercial internet across every major cycle (Web1 → Web3). With a proven 12-0 founder record, James specializes in scaling high-integrity publishing networks that prioritize deep engagement over clickbait.
From pioneering the digital subscription model at Rivals.com to architecting the $1B Google-Myspace deal, his career has been a continuous effort to maximize the value of premium content. Today, as CEO of Roundtable (NASDAQ: RVYL), he is applying these decades of structural experience to solve the AI crisis for publishers.
His operational footprint extends beyond mere founding roles; James has been a central architect in some of the most significant liquidity events in digital media history. He has successfully navigated three distinct waves of internet evolution, consistently delivering exits to major conglomerates including Yahoo! and News Corp. His 12-0 record is not just a tally of sales, but a testament to a philosophy: building robust, revenue-generating infrastructure that survives market cycles and delivers tangible value to shareholders.
WEB 1.0: AGGREGATION
Rivals.com – Founder & CEO
Recognized that sports fans wanted deep, specific intel, not generic headlines. Pioneered the first large-scale digital subscription network, proving users would pay for high-quality, niche content.
ACQUIRED BY YAHOO!
WEB 1.0: SCALE
Scout.com – Founder & CEO
Scaled the Rivals model using the same engineering core to dominate niche publishing. Built a network of hundreds of independent publishers operating on a shared infrastructure.
ACQUIRED BY FOX INTERACTIVE
WEB 2.0: PLATFORMS
Fox Interactive – Chief Strategy Officer
Led global strategy for one of the world's largest digital media portfolios. Architected the landmark $1B Google–Myspace partnership and contributed to the initial business architecture for Hulu.
WEB 2.0: CONSORTIUMS
5to1.com – Founder & CEO
Created a premium advertising consortium to combat the commoditization of inventory by ad networks. United major publishers to demand fair value for their audiences.
ACQUIRED BY YAHOO!
WEB 3.0: SOVEREIGNTY
Roundtable – Founder & CEO
Building the Unified Media OS to end the "Rented Era." Delivering data ownership, decentralized payments, and identity verification to the world's leading media brands.
NASDAQ LISTED (RVYL)