On this episode of the Business of Betting Podcast, Jeff Edelstein sits down with Jonathan Gruber, Founder and CEO of Loserball, to discuss a unique twist on fantasy sports where success comes from predicting failure. Hear them discuss: 00:00 – Introduction to Jonathan Gruber 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 subscribe so you can play next football season. ⚡️ Follow BoB on Twitter/X ⚡️ Watch BoB on Youtube ⚡️ Apply to be a guest here

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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