In our second episode, Biplab sits down with Jake Flomenberg of Wing to discuss the AI investment thesis that helped him build companies like Demisto, Oasis Labs and Radar. Topics include Wing’s mission (1:00 ); how to distinguish good investments from bad investments (1:54 ); approaching AI investment in a crowded marketplace (3:20 ); asking founders ‘why’ over ‘how’ (6:27 );  the importance of a strong vision (12:00 ); the difference between revolutionary vs. evolutionary AI (13:03 ); Jake’s investment decision criteria (16:37 ); prioritizing transparency when a partnership doesn’t go as planned (18:20 ); differentiating optimism from misrepresentation (20:00 ); what investment has surprised Jake most (20:50 ); and his biggest investment regrets (21:56 ).