The Gamble & The Glory: S2 E2 - John Levy from theScore

Update: 2025-11-18

Description

The Gamble & The Glory showcases founders that built their companies into category leaders in the betting and gaming industry.

In S2 E2, we speak with John Levy, founder and former CEO of theScore. John shares the remarkable 25+ year journey behind one of Canada’s most iconic sports media and betting brands from its roots in cable television to becoming a digital powerhouse and ultimately exiting for over $2 billion.

Hear him discuss:

The early days of Sportscope and how it evolved into theScore

How selling the TV network unlocked theScore’s digital transformation

Selling the media assets to bet the future of the company on digital media and technology

Why Penn’s acquisition derailed early and what went wrong with the integration

Lessons from scaling a family-run business and defining clear leadership roles

His candid thoughts on ESPN BET, Barstool, Dave Portnoy, and partnership misalignment

How theScore Bet could have continued to grow under an independent model

The future of sports betting across AI, microbetting, and next-gen fan behavior

How theScore was able to punch above its weight, and John's advice to startup founders on how to do the same

Why authenticity, resilience, and focus define long-term winners

What’s next for John Levy, and whether another venture is on the horizon

For more of John's comments on the recent ESPN Bet news, check out his recent podcast with Steve McAllister on Gaming News Canada: https://open.spotify.com/episode/2uocQx14rRzS92YF8wlnqC?si=ce3b2267cfad4a57

Video version of this episode can be viewed here.

Learn more 👇

➡️ theScore website

➡️ John Levy on Linkedin

The Gamble & The Glory is made possible by Segev LLP, a full solutions law firm purpose-built for the gaming and betting industry. To learn more, visit: www.segev.ca.