This episode explores the journey of a high school dropout turned computer scientist who founded a supersonic jet company, Boom, detailing his motivations and strategies. Against the backdrop of his initial struggles with a barcode scanning game startup and subsequent reflection at Groupon, he emphasizes the importance of pursuing ideas aligned with personal passion to overcome inevitable challenges. More significantly, the discussion pivots to Boom's inception, driven by the question of why supersonic flight hadn't progressed since the Concorde, revealing a focus on fuel efficiency and challenging conventional wisdom through first principles thinking. As the conversation unfolds, the founder shares his fundraising hurdles, emphasizing the misalignment between venture capital incentives and long-term hard tech investments, while also recounting securing a pivotal LOI from Virgin after a series of high-agency maneuvers. The episode culminates in a reflection on ambition, the value of trying, and the importance of accountability, drawing parallels with Jeff Bezos' leadership style and the power of asking the most important question, illustrating emerging industry patterns reflected in Boom's pursuit of a seemingly impossible goal.