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

This Week In Startups is made possible by:

Vanta: vanta.com/twist

DigitalOcean: do.co/twist

Sentry: sentry.io/twist

Plaud: 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: x.com/rshanreddy

Aristotle: heyaristotle.com

Relevant Links:

Shoe Dog by Phil Knight → en.wikipedia.org/wiki/Shoe_Dog

Something Like an Autobiography by Akira Kurosawa → en.wikipedia.org/wiki/Something_Like_an_Autobi…

Einstein: His Life and Universe by Walter Isaacson, which Dovid is reading now → en.wikipedia.org/wiki/Einstein:_His_Life_and_U…

Gartner, Jason's example of firms doing research on behalf of corporations → 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 → inquirer.com/news/nation-world/religious-leade…

David Sacks accuses Anthropic of a "regulatory capture strategy based on fear-mongering"; the line Lon references (Bloomberg Law) → news.bloomberglaw.com/artificial-intelligence/…

Aristotle's $5M seed round (PR Newswire) → prnewswire.com/news-releases/aristotle-secures…

"The 2 Sigma Problem" by Benjamin Bloom (1984), original paper → web.mit.edu/5.95/readings/bloom-two-sigma.pdf

Journal record (Educational Researcher / SAGE) → journals.sagepub.com/doi/10.3102/0013189X01300…

NYC's AI moratorium through 8th grade (ABC News) → abcnews.com/Technology/new-york-city-public-sc…

Alpha School → alpha.school

Brilliant's origin story at the LAUNCH Festival (NPR) → npr.org/blogs/alltechconsidered/2013/07/23/203…

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 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 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 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 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: twistartups.substack.com

TWiAI: thisweekinai.ai

TWiVC: thisweekinvc.substack.com

Subscribe to This Week in Startups on Apple: rb.gy/v19fcp

Follow Lon:

X: x.com/lons

Follow Jason:

X: twitter.com/Jason

LinkedIn: linkedin.com/in/jasoncalacanis

Check out all our partner offers: partners.launch.co