Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346
October 5, 2026
AI Summary
5 min readJason Mentors The Next Generation + Why AI Is Bad at Teaching
Jason Calacanis spent much of this episode taking live calls from young people—a high school senior from India headed to Fordham, an NYU student who attended the All-In Summit, and an AI researcher working on protein folding—before interviewing Sean Reddy, CEO of Aristotle, about building an AI tutor that actually teaches rather than just answers.
The Biography Protocol for Young Founders
When Augustya, a soon-to-be Fordham freshman from India, asked for career advice, Calacanis gave him a specific curriculum: read one biography per month, ten per year, and not just business books. "Read Michael Ovitz's CAA biography, then the oral history of CAA, then Bob Iger's biography," he said. "You would understand that entire finance picture and how that business grew from the 50s, 60s, 70s into the 90s." He also recommended Born Standing Up by Steve Martin, Robin Williams's biography, and Stephen King's On Writing.
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What you'll learn
- 1 Timestamped Outline
- 2 (00:00) **Opening & Housekeeping** - Jason introduces the episode and runs through sponsor ads for Plaud, Sentry, DigitalOcean, and Vanta
- 3 (01:51) **Caller 1: Agasta from India, Fordham-bound** - A young student calls in to ask Jason for advice on finance, New York, and dating
- 4 (04:32) **Jason's Advice: Be AI-First + Read Biographies** - The core strategic advice segment for the young caller
- 5 (09:00) **Agasta's Mom Wants a Free Talk** - The caller's mother is Harvard Bangalore club president and asks Jason to speak
- 6 (11:55) **Caller 2: David Returns from All-In Summit** - A returning caller who got into the All-In Summit through a previous show appearance asks about a $500K hypothetical
- 7 (14:00) **Jason's Framework: Four Uses for $500K** - The strategic breakdown of what to do with sudden capital
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
This Week In Startups is made possible by: Vanta: https://www.vanta.com/twist DigitalOcean: https://do.co/twist Sentry: http://sentry.io/twist Plaud: http://Plaud.ai/twist Today’s show: The smarter AI gets, the more it just does the work for you, and the less helpful it becomes as a tutor. Shan Reddy of Aristotle joins Jason to demo a voice-first tutor built to run a session the way a $200-an-hour human tutor would. We also dive into why frontier models are trained to hand you answers rather than build real understanding. PLUS, in Ask Jason, an incoming Fordham student (Jason’s alma mater!) wants to prepare for a career in finance. Plus, David from NYU calls back and wants to discuss what everyone would do with $500K in free money. Then, why does Jason think the Doomerism is coming from inside the AI labs? Guests: Shan Reddy on X: https://x.com/rshanreddy Aristotle: https://www.heyaristotle.com/ Relevant Links: Shoe Dog by Phil Knight → https://en.wikipedia.org/wiki/Shoe_Dog Something Like an Autobiography by Akira Kurosawa → https://en.wikipedia.org/wiki/Something_Like_an_Autobiography Einstein: His Life and Universe by Walter Isaacson, which Dovid is reading now → https://en.wikipedia.org/wiki/Einstein:_His_Life_and_Universe Gartner, Jason's example of firms doing research on behalf of corporations → https://www.gartner.com/ "Religious Scholars Met With Anthropic. What They Heard Stunned Them." by Elizabeth Dias, The New York Times, Sept. 29, 2026; the story Lon brings up → https://www.inquirer.com/news/nation-world/religious-leaders-met-with-anthropic-20260930.html David Sacks accuses Anthropic of a "regulatory capture strategy based on fear-mongering"; the line Lon references (Bloomberg Law) → https://news.bloomberglaw.com/artificial-intelligence/anthropic-is-running-a-strategy-based-on-fear-mongering-sacks Aristotle's $5M seed round (PR Newswire) → https://www.prnewswire.com/news-releases/aristotle-secures-5m-to-replace-the-chatbot-with-high-dosage-ai-tutoring-for-students-302880500.html "The 2 Sigma Problem" by Benjamin Bloom (1984), original paper → https://web.mit.edu/5.95/readings/bloom-two-sigma.pdf Journal record (Educational Researcher / SAGE) → https://journals.sagepub.com/doi/10.3102/0013189X013006004 NYC's AI moratorium through 8th grade (ABC News) → https://abcnews.com/Technology/new-york-city-public-schools-banning-ai-middle/story?id=136134872 Alpha School → https://www.alpha.school Brilliant's origin story at the LAUNCH Festival (NPR) → https://www.npr.org/blogs/alltechconsidered/2013/07/23/203677692/giving-brightest-kids-the-cram-school-experience-online Timestamps: 0:00 Live Ask Jason kicks off 0:14 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin S. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off! 0:56 Fordham-bound caller asks how to break into finance in the AI era 5:15 Jason's gift: read one biography a month 9:22 Vanta: Get $1000 off