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

This Week In Startups is made possible by: Vanta: https://www.vanta.com/twist DigitalOcean: https://do.co/twist Sentry: https://sentry.io/twist Plaud: https://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: 00:00:00 Live Ask Jason kicks off 00:00:14 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! 00:00:56 Fordham-bound caller asks how to break into finance in the AI era 00:05:59 Jason's gift: read one biography a month 00:10:06 Vanta: Get $1000 off your SOC 2 at https://www.vanta.com/twist 00:12:06 Returning caller David: what would you do with $500K? 00:19:53 DigitalOcean: Want to see what building on a true AI-native platform looks like? Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today - and cut your AI workload costs by up to 50%. 00:24:40 Bringing an AI protein folding tool into drug discovery 00:27:19 How to do customer discovery with big companies 00:29:44 The "dark arts" of market research and corporate intelligence 00:30:13 Sentry: Your team should be focused on shipping features - not chasing down bugs. New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26 00:33:43 Is AI fear a dark PR campaign? 00:35:01 Anthropic meets with religious scholars 00:40:45 Are AI labs living through an Oppenheimer moment? 00:42:50 Why we need to talk about AI's upside in education 00:44:31 Sean Ready, co-founder and CEO of Aristotle, joins 00:45:42 Why AI models are getting worse at teaching 00:47:53 Aristotle demo: a voice AI tutor for AP Calculus 00:51:13 Predicting the next best teaching action 00:54:16 Bloom's two sigma problem and one-on-one tutoring 00:55:22 Aristotle's business model and pricing 00:57:53 Building a tutoring harness vs. relying on frontier labs 01:01:05 Why dyslexic students love Aristotle 01:02:40 Hand-grading thousands of hours of tutoring sessions 01:05:06 Socialization, classrooms and the future of public education 01:09:16 Where to try Aristotle and open roles Subscribe to our newsletters on Substack: TWiST: https://twistartups.substack.com/ TWiAI: https://www.thisweekinai.ai/ TWiVC: https://thisweekinvc.substack.com/ Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/