This Week in Startups

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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 your SOC 2 at https://www.vanta.com/twist
11:22 Returning caller David: what would you do with $500K?
19:09 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%.
23:56 Bringing an AI protein folding tool into drug discovery
26:35 How to do customer discovery with big companies
29:00 The "dark arts" of market research and corporate intelligence
29:29 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
32:59 Is AI fear a dark PR campaign?
34:17 Anthropic meets with religious scholars
40:01 Are AI labs living through an Oppenheimer moment?
42:06 Why we need to talk about AI's upside in education
43:47 Sean Ready, co-founder and CEO of Aristotle, joins
44:58 Why AI models are getting worse at teaching
47:09 Aristotle demo: a voice AI tutor for AP Calculus
50:29 Predicting the next best teaching action
53:32 Bloom's two sigma problem and one-on-one tutoring
54:38 Aristotle's business model and pricing
57:09 Building a tutoring harness vs. relying on frontier labs
1:00:21 Why dyslexic students love Aristotle
1:01:56 Hand-grading thousands of hours of tutoring sessions
1:04:22 Socialization, classrooms and the future of public education
1:08:32 Where to try Aristotle and open roles

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Today’s show:

What can AI do with the guardrails OFF? Devon Thomas of Abliteration.ai thinks defenders should have access to the same kinds of tools, rather than having one hand tied behind their backs.

Then, on Ask Jason, learn what AI means for the billable hour from a legal-tech founder. PLUS, are AI microdramas a real ecosystem or a fad, and does AI finally make solo founders fundable?

Guests:

Devon Thomas on X: https://x.com/founderengineer Abliteration: https://abliteration.ai/

Relevant Links:

Abliteration.ai on a16z speedrun — the accelerator Jason congratulated Devon on → https://speedrun.a16z.com/companies/abliteration

TechCrunch: "Abliteration.ai is making a business out of removing AI guardrails" — the coverage behind the recent attention → https://techcrunch.com/2026/09/03/abliteration-ai-is-making-a-business-out-of-removing-ai-guardrails/

Abliteration.ai press page → https://abliteration.ai/press

Anthropic Frontier Red Team: "GLM-5.3 and the spread of advanced cyber capabilities" — the blog Devon cited on how capable abliterated GLM-5.3 is → https://www.anthropic.com/research/glm-5-3-and-the-spread-of-advanced-cyber-capabilities

CNBC: Trump's executive order renaming AI "super intelligence," signed the same day → https://www.cnbc.com/2026/09/29/trump-ai-super-intelligence.html

Nextgov/FCW: OpenAI agents accessed Census and SEC data — detail on the dozens of organizations OpenAI notified → https://www.nextgov.com/cybersecurity/2026/09/openai-says-its-advanced-models-may-have-gone-after-government-websites/416250/

Financial Times: "AI wrecking ball fractures billable-hour fee model"

Seedance 2.5 — ByteDance's video model Bruno asked about → https://technode.com/2026/07/31/bytedance-launches-seedance-2-5-video-generation-model/

Pixar / Toy Story — the CGI "Toy Story moment" Jason expects for AI video → https://en.wikipedia.org/wiki/Toy_Story

Practi — Mathew's platform for helping law firms move from hourly billing to subscriptions → https://practi.ai/hello

Timestamps:

0:00 What http://Abliteration.ai does, and who the frontier labs are shutting out

2:44 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!

2:56 Why defenders don't get the attackers' tools

4:16 "Inversion of control": letting customers set their own guardrails

6:47 Who's liable? The hammer analogy and the White House self-regulation pact

10:11 Every: For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io.

13:10 Why AI labs publicize their scariest hacks

18:52 Customers: from cyber startups to Fortune 500 CISOs

19:56 Northwest Registered Agent: Got a new business idea? Northwest Registered Agent helps you bring it to life. Get a free domain, email, phone number, and more - with no purchase required! - Learn more at http://northwestregisteredagent.com/twistdomain

24:41 Chinese image and video models

27:20 Why most businesses still barely use AI

29:02 Ask Jason begins

29:24 Mathew Kerbis (Practi): What does AI do to the billable hour?

30:16 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist

32:45 Will subscriptions replace hourly billing?

37:27 Bruno Vilela: Are AI microdramas an ecosystem or a fad?

39:35 Lon's microdrama pitch to Snapchat and TikTok's PineDrama

48:09 Josh Ezell: Does AI change the bias against solo founders?

49:26 Jason's three-two-one framework and the risks founders must eliminate

Subscribe to our newsletters on Substack:

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Today’s show:

Google once interviewed the entire Justin.tv (now Twitch) team and then walked away from an acquisition deal, saying they weren’t good enough. Seven investors passed on buying 10% of Airbnb for $150,000, a stake pegged at roughly $9.25 billion today.

Lon Harris and Alex Wilhelm revisit classic TWiST interviews with Justin Kan of Twitch and Brian Chesky of Airbnb to find out what those founders understood that the market didn't.

PLUS, how did a box of cereal win over Paul Graham and get Airbnb into Y Combinator?

Flashback Guests:

Justin Kan on X: https://x.com/justinkan Twitch: https://www.twitch.tv/

Justin Kan (@justinkan) on X

Brian Chesky on X: https://x.com/bchesky AirBnB: https://www.airbnb.com/

Relevant Links:

TWiST E900: Justin Kan, co-founder of Justin.tv, Twitch & Atrium (Feb 5, 2019) → https://thisweekinstartups.com/episodes/L3DP8VCE12s

TWiST E1735: Airbnb CEO Brian Chesky on early rejection, customer focus & AI (May 4, 2023) → https://www.youtube.com/watch?v=aZ-BjJZxNoA

Halo 3: the game that flooded Mahalo with traffic → https://en.wikipedia.org/wiki/Halo_3

Weblogs, Inc.: Jason's blog network, home of Engadget → https://en.wikipedia.org/wiki/Weblogs,_Inc.

Instinct: the invite-only personal AI agent from founder Noah Shinn → https://www.instinct.co/

AMD to acquire World Labs for $8.2B in stock; Li becomes AMD chief scientist (Bloomberg) → https://www.bloomberg.com/news/articles/2026-09-28/amd-to-buy-fei-fei-li-s-world-labs-ai-startup-for-8-2-billion

Lovable: where Lon says he'd rebuild a bad app in two hours → https://lovable.dev/

Y Combinator → https://www.ycombinator.com/

Paul Graham on X → https://x.com/paulg

Obama O's and Cap'n McCain's: the cereal that funded Airbnb → https://en.wikipedia.org/wiki/Airbnb#History

Stripe: what Paul Graham suggested they build instead → https://stripe.com/

Timestamps:

0:00 Justin Kan on episode 900 (Feb 2019)

3:44 When Jason and Justin realized people watch gaming

5:52 Mahalo, Halo 3, and betting a company on 3% of its traffic

10:21 CLA: Get started with CLA's CPAs, consultants, and wealth advisors now at https://www.claconnect.com/withyou

11:42 The "zombie startup" years and Google's rejection

17:06 Instinct: the AI agent built for venture capitalists

19:43 Sentry: New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26

28:08 Kozmo.com and the era of "make number go up"

30:06 Lightfield: Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at https://lightfield.app/

32:57 Why AI companies have to monetize faster

34:00 Clip: Justin Kan on knowing yourself as a founder

37:24 An early rejection of "founder mode"?

38:33 Brian Chesky on episode 1735 (May 2023)

39:27 "I hope that's not the only idea you're working on"

43:27 What 10% of Airbnb for $150K is worth today

46:05 Obama O's and the Y Combinator interview

48:15 Why investors fund unkillable, attention-hacking founders

54:37 Clip: Chesky on AI, deepfakes, and authenticity

58:13 Is AI costing jobs or just making them busier?

1:05:04 Did AI create "millions of startups"?

Subscribe to our newsletters on Substack:

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Follow Lon:

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

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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This Week In Startups is made possible by:

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Today’s show:

A product that would have cost $500,000 to build in 2006 now costs less than a used car. Jason put up $5,000 on an idea he'd been sitting on for 20 years, and so far, we’ve received dozens of amazing submissions from vibecode experts.
See how well the Top 3 demos fare, and which app was so good, Jason’s already thinking about spinning it off into a startup.
PLUS, an unhoused founder calls in asking how to raise money for not one but two pre-revenue startups? Hear Jason and Lon’s advice.

Submissions:

Submission 1 — https://annotated.wtf By Robert
Submission 2 — https://annotated.bytetalk.ai/feed By Alan Shiflett
Alan on X: https://x.com/alanshiflett
Submission 3 — https://anotated.com/ By Chirag Asarpota
Chirag on X: https://x.com/ChiragAsarpota

Relevant Links:

annotated.com bounty brief — https://annotated.lovable.app/
All active TWiST bounties — https://www.thisweekinstartups.com/bo...
The other open $5,000 bounty: a sidebar companion app for podcasts — https://www.notion.so/launch1/5K-Boun...

Timestamps:

0:00 Why Jason bought annotated.com
0:33 The original idea: highlight any sentence on the web and dispute it
1:25 The rules: the code is open source, and Jason can cancel any time
2:06 Submission 1: Robert's annotated.wtf
9:31 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io11:36 Submission 1 Scoring
11:51 Submission 2: Allan Shifflet's take
13:19 What it got right: profiles, follower counts, trending topics
16:03 Submission 3: annotaed.com, and buying the typo domain on purpose
19:43 Northwest Registered Agent - Got a new business idea? Northwest Registered Agent helps you bring it to life. Get a free domain, email, phone number, and more - with no purchase required! Learn more at https://www.northwestregisteredagent....22:49 Final scores, and how to enter round two
24:11 Incubating annotated inside a venture firm
29:09 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST
29:41 Ask Jason: a homeless founder with two startup ideas

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Today’s show:

Timestamps:

0:00 Will Ternus take "massively big swings"?

3:43 Round 1: ElevenLabs

4:46 Round 1: Disney

6:18 Round 2: Sony

8:22 Round 2: Boston Dynamics

9:23 Round 3: Perplexity

10:02 AD: PayPal is built for all business. Get started at https://paypal.com/business

11:52 Round 3: DigitalOcean

13:02 More picks: Etched

14:30 More picks: Lucid

15:58 More picks: Superhuman

16:48 More picks: Higgsfield and more

18:09 Fans make their selections

19:47 AD: Got a new business idea? @northwestagent helps you bring it to life. Get a free domain, email, phone number, and more, with no purchase required! Learn more at www.northwestregisteredagent.com/twistdomain

25:37 Stacy Salvi of The90 joins

29:28 AD: Thanks to our partner, Odoo, the all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist

34:38 How the app calculates your Sunscore

42:12 Building a UV research dataset

45:09 Should The90 make a version for men?

Names & Links

Stacy Salvi - https://www.instagram.com/stacysalvi/

The90 - https://the90.com/

Description

Wall Street suspects new Apple CEO John Ternus may do something predecessor Tim Cook almost never did: writing a huge check.

So Jason and Lon are playing “fantasy draft” with Apple’s balance sheet, choosing five real companies to acquire over five “rounds.” Disney buys them a ton of IP and unlocks theme park synergies. Sony gets them a gaming console and massive anime distribution. Boston Dynamics buys them lots of robots, while Etched nets them cheaper inference. So many options!

Then, we chat with Stacy Salvi of The90. Her wearable pendant tells you exactly how much sun damage you’re accumulating, long before you start to burn.

Guest

The90: https://the90.com/

Stacy Salvi on LinkedIn: https://www.linkedin.com/in/stacysalvi/

Relevant Links

John Ternus becomes Apple CEO: https://www.apple.com/newsroom/2026/04/tim-cook-to-become-apple-executive-chairman-john-ternus-to-become-apple-ceo/

Analyst: Ternus could bring bigger acquisitions: https://9to5mac.com/?p=1065466

“Grok Has Money” meme origin: https://x.com/gmfarcaster/status/2026318035103965414

Sunlight linked with lower COVID-19 deaths: https://www.ed.ac.uk/news/2021/sunlight-linked-with-lower-covid-19-deaths

Reid Hoffman: “If there aren’t any typos in this essay, we launched too late”: https://www.linkedin.com/pulse/arent-any-typos-essay-we-launched-too-late-reid-hoffman/

Draft Picks

ElevenLabs: https://elevenlabs.io/

Disney: https://thewaltdisneycompany.com/

Sony Group: https://www.sony.com/en/

Crunchyroll: https://www.crunchyroll.com/

Boston Dynamics: https://bostondynamics.com/

Perplexity: https://www.perplexity.ai/

DigitalOcean: https://www.digitalocean.com/

Etched: https://www.etched.com/

Rivian: https://rivian.com/

Lucid Motors: https://lucidmotors.com/

Superhuman: https://superhuman.com/

World Labs: https://www.worldlabs.ai/

PrismML: https://prismml.com/

Liquid AI: https://www.liquid.ai/

Kagi: https://kagi.com/

Sonos: https://www.sonos.com/en-us/shop

Whoop: https://www.whoop.com/

Oura: https://ouraring.com/

Peloton: https://www.onepeloton.com/

Subscribe to our newsletters on Substack:

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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/

Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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