Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346

Jason Calacanis opens with an Ask Jason segment, mentoring a Fordham-bound caller on breaking into finance (his advice: read one biography a month) and advising David from NYU on what to do with $500K. The conversation shifts to whether AI doomerism is a dark PR campaign after Lon Harris highlights Anthropic's meeting with religious scholars. Then, Shan Reddy, co-founder and CEO of Aristotle, joins to demo a voice-first AI tutor built to run sessions like a $200-an-hour human tutor. They explore why frontier models are getting worse at teaching, Bloom's Two Sigma Problem on the power of one-on-one tutoring, and the labor-intensive process of building a domain-specific teaching harness.