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 subscribe so you can play next football season.

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