E287 - Jonathan Gruber from Loserball

On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Jonathan Gruber, Founder of Loserball, to discuss a unique twist on fantasy sports where success comes from predicting failure. Hear them discuss: 00:00 – Introduction to Jonathan's background and the concept behind Loserball 01:00 – The “contrarian” fantasy sports model: rooting for everything to go wrong 02:00 – How the game works: categories of futility, weighted questions, and strategy 04:00 – Early product experimentation and why pure chaos didn’t work for most players 06:00 – Finding the right balance between humor, unpredictability, and skill-based play 08:00 – The origins of the idea and how traditional fantasy sports became too complex 11:00 – Why community banter and shared misery can be just as entertaining as winning 14:00 – Lessons learned from building and iterating on a niche sports gaming product 18:00 – Who the ideal Loserball player is and why fantasy players enjoy the twist 23:00 – The future of alternative fantasy formats and opportunities for experimentation in sports gaming Want to play for yourself? Head to Loserball.com to learn more and

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E287 - Jonathan Gruber from Loserball is an episode from Business of Betting Podcast by Business of Betting Podcast.

This episode is 30:00 long.

This episode was published on Apr 16, 2026.

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