Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.
Site
RSS
Spotify
Apple
Data updated on 06/10/2026
Recent rankings
Latest chart positions across Apple Podcasts and Spotify rankings.
Shared links between episodes and podcasts
Links found in episode descriptions and other podcasts that share them.
Jason Mentors The Next Generation + Why AI Is Bad at Teaching (Aristotle Interview) | E2346
Monday, October 5, 2026 • Duration 01:10:31
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 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
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/
Inside The Startup Building Uncensored AI (Abliteration AI) | EP 2345
Saturday, October 3, 2026 • Duration 53:15
This Week In Startups is made possible by:
Every.io: http://every.io/
Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain
Odoo: http://Odoo.com/twist
Plaud: http://Plaud.ai/twist
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:
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/
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344
Thursday, October 1, 2026 • Duration 01:18:04
This Week In Startups is made possible by:
Plaud: http://Plaud.ai/twist CLA: https://claconnect.com/tech Sentry: http://sentry.io/twist Lightfield: http://sentry.io/twist
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:
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/
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Jason’s Put a $5K Bounty on His Dream Chrome Extension | E2338
Monday, September 28, 2026 • Duration 40:46
This Week In Startups is made possible by:
Every.io: http://every.io/
Northwest Registered Agent: www.northwestregisteredagent.com/twistdomain
Sentry: http://sentry.io/twist
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
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.com
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
Follow Lon:
X: https://x.com/lons
Follow Jason:
X: / jason
LinkedIn: / jasoncalacanis
The 5 Companies Apple Must Buy
Monday, September 28, 2026 • Duration 50:20
This Week In Startups is made possible by: PayPal - https://paypal.com/business Northwest Registered Agent - https://www.northwestregisteredagent.com/twistdomain Odoo - https://Odoo.com/twist
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:
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/
Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
A rogue OpenAI agent hacked Australia’s government. Does this matter? | E2342
Friday, September 25, 2026 • Duration 01:25:53
This Week In Startups is made possible by:
https://lightfield.app/
http://getpaper.ai/twist
https://conservationfund.org/
http://Plaud.ai/twist
https://www.athena.com/jcal
Today’s show:
An OpenAI agent breached Australia's Medicare statistics portal in June, and it took 84 days for the Frontier Lab to publicly acknowledge it. Jason and Lon dig into whether this is an important cautionary tale about alignment, or if PM Anthony Albanese looking to join the AI conversation.
Then Bryant Chou of Ploy joins to explain skipping pre-seed and seed entirely to raise $27M, and why he’s taking his time to build his all-in-one agentic solution for running businesses.
Learn why Google is launching four TPUs into orbit for Project Suncatcher. PLUS, how many robots a week is Tesla now shipping with Optimus, and Jensen Huang told Ezra Klein basic math no longer matters. Is he right? Can we forget long division, at last?
Guests:
Bryant Chou on X: https://x.com/bryantchou PloyAI: https://ploy.ai/
Relevant Links:
Ploy raises $27M seed led by First Round Capital and Y Combinator (Founderland) → https://www.founderland.ai/articles/webflow-co-founder-launches-ai-marketing-platform-with-27m-s-mqj8o952
OpenAI's $2M-in-tokens offer to every YC startup(TechCrunch via Yahoo) → https://finance.yahoo.com/sectors/technology/articles/sam-altman-makes-mic-drop-212302858.html
Original Bloomberg report on the a16z probe → https://www.bloomberg.com/news/articles/2026-08-17/andreessen-horowitz-focus-of-doj-probe-over-board-directors
Google: Project Suncatcher's first test launch on SpaceX's Transporter-18 → https://blog.google/innovation-and-ai/models-and-research/google-research/google-project-suncatcher-facts/
ABC News (Australia): full timeline, from the June 18 breach to OpenAI's Sept. 10 email → https://www.abc.net.au/news/2026-09-24/ai-agent-accessed-australian-government-site-pm-says/107189078
Ando emerges from stealth with $20M to take on Slack (TechCrunch) → https://techcrunch.com/2026/09/24/ando-eyes-slack-as-it-builds-team-messaging-platform-for-humans-and-agents-to-work-together/
Google's $900M investment in SpaceX's $1B round, January 2015 (VentureBeat) → https://venturebeat.com/technology/google-confirms-it-put-900m-into-spacexs-1b-round
Tesla ramps Optimus to several hundred robots a week; hands are the bottleneck (Electrek, summarizing The Information) → https://electrek.co/2026/09/25/tesla-optimus-production-ramp-hands-ai-generalization-problems/
Jensen Huang tells Ezra Klein forgetting basic math may not matter, and that he doesn't know his own address (Kotaku) → https://kotaku.com/nvidia-ceo-doesnt-care-that-kids-are-forgetting-basic-math-because-of-ai-i-actually-dont-know-my-address-2000737092
Sydney Sweeney's Novig "Just Sports" ad and the athlete backlash, including Amy Hunt's comment (Yahoo) → https://www.yahoo.com/entertainment/celebrity/articles/sydney-sweeney-novig-ad-controversy-172900515.html
Nike exits the S&P 100 after 18 years (Fortune) → https://fortune.com/2026/09/08/nike-stock-plummets-sp500-market-cap-index/
The Further Mis-Adventures of Cliff Booth trailer: David Fincher directs Tarantino's script; IMAX Nov. 25, Netflix Dec. 23 (Variety) → https://variety.com/2026/film/news/the-further-mis-adventures-cliff-booth-trailer-brad-pitt-1236701901/
Timestamps:
0:00 Whoop fire alarm: Jason's dry-aged steak incident
1:30 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!
4:45 News: an OpenAI agent breached Australia's Medicare statistics portal
12:48 Scraper or hack? Australia's PM jumps into the AI safety debate
13:31 News: Google launches four TPUs into orbit for Project Suncatcher
18:27 Guest: Bryant Chou of PloyAI
20:07 AD: Paper is the legal backbone for thousands of startup founders and fund managers - including Launch. Use getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta.
21:11 Ploy's thesis: your website as your hardest working employee
27:05 Why a repeat unicorn founder went back to Y Combinator
38:55 The DOJ probe into a16z's Databricks and Fivetran board seats
44:57 "Nobody's thinking about you": Jason's stair story
45:17 Frontier models vs. your own model, and OpenAI's $2M YC token deal
54:04 News: Ando wants to replace Slack with agent-native chat
1:01:08 News: Tesla ramps Optimus to several hundred robots a week
1:04:48 Off-Duty: Jensen Huang tells Ezra Klein basic math may not matter
1:08:31 The MIT "Your Brain on ChatGPT" EEG study
1:09:57 Jason's five-part reset: sleep, diet, exercise, socializing, meditation
1:11:45 Off-Duty: Sydney Sweeney's Novig ad backlash
1:21:07 The Further Mis-Adventures of Cliff Booth trailer
1:23:41 Jason's first car: a 1970 Mustang GrandeSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.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
Subscribe to our Substack Newsletters!
TWiST: https://twistartups.substack.com/
TWiAI: https://www.thisweekinai.ai/
TWiVC: https://thisweekinvc.substack.com/
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
VCs Would Bet on Open-Source AI Over OpenAI and Anthropic | E2341
Wednesday, September 23, 2026 • Duration 01:27:02
This Week In Startups is made possible by:
Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain Odoo: http://Odoo.com/twist Rippling: http://Rippling.ai/twist Plaud: http://Plaud.ai/twist Harmonic: http://harmonic.ai/
Today’s show:
Anthropic and OpenAI released cheaper models on the same day with Claude Opus 5.5 and GPT-6, and these VCs would still bet on open source. Jason brings on Dave McClure of Practical Venture Capital, Jeff Clavier of Uncork Capital, and Jenny Fielding of Everywhere Ventures to discuss the argument for open-weight models over the frontier labs.
Learn why median seed valuations have more than tripled since 2017. Why does Dave say it's a buyer's market for secondaries right now? PLUS, does Meta's Muse leave any room for Instinct, and why are fintech and healthcare suddenly out of favor?
Guests:
Dave McClure on X: https://x.com/davemcclure?lang=en Practical Venture Capital: https://practicalvc.com/
Jeff Clavier on X: https://x.com/jeff Uncorked Capital: https://uncorkcapital.com/
Jenny Fiedling on X: https://x.com/jefielding Everywhere Ventures: https://www.everywhere.vc/
Relevant Links:
Instinct reportedly seeking $1B at a $10B valuation (report via The Information) → https://cryptobriefing.com/ai-assistant-startup-instinct-targets-10b-valuation-in-new-funding-talks-report/
Meta's Muse, the agent the panel sees as Instinct's biggest threat, now on Mac → https://aiweekly.co/alerts/meta-ships-muse-for-mac-agent-now-acts-in-native-macos-apps
Trump calls Jensen Huang onstage at the All-In Summit → https://thenextweb.com/news/trump-phoned-jensen-huang-onstage-at-the-all-in-summit-to-call-ai-fear-a-hoax
AI-assisted intel error nearly triggered a US intercept of a Chinese ship (CNN via gCaptain) → https://gcaptain.com/ai-error-nearly-triggered-u-s-intercept-of-chinese-ship-cnn-reports/
Bernie Sanders' 50% AI sovereign wealth fund bill + Altman meeting (Fortune) → https://fortune.com/2026/06/18/bernie-sanders-ai-fund-bill-sam-altman-1000-payments/
Stanley Druckenmiller's AI-written WSJ op-ed (Axios) → https://axios.com/2026/08/26/stanley-druckenmiller-ai-writing-wsj-op-ed
Claude Opus 5.5 and GPT-6 Sol/Luna launch the same day with price cuts (SiliconANGLE) → https://siliconangle.com/2026/09/22/anthropic-releases-claude-opus-5-5-and-openai-counters-with-two-cheaper-gpt-6-models/
Zipline: LAUNCH's "miss," later backed through the syndicate → https://www.flyzipline.com/
Micro1 → https://www.micro1.ai/
Founder University → **https://www.founder.university/** [VERIFY]
The Syndicate: angel invest alongside LAUNCH (apply, waitlist) → **https://thesyndicate.com/**
Timestamps:
0:00 What seed rounds looked like then: Fitbit's $2M seed
2:38 Jenny's Techstars NYC years and the two-unicorn mug
6:10 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!
7:51 All-In Summit: Trump calls Jensen Huang onstage. Staged or not?
8:56 P(doom) roundtable + Dave's AI sovereign wealth fund prediction
10:08 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.com/twistdomain
13:35 The AI intel error that nearly triggered a US-China incident
17:44 "McClure's Law": a human with AI is the real risk
19:59 Odoo - The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist
21:37 Stripe + OpenRouter: an anti-fraud play, not a routing play?
23:07 Seed valuations: median $8M (2017) to $28M today
23:58 Instinct: $2.5B to a reported $10B in weeks
29:49 Rippling - Thanks to our partners at Rippling! Head to https://Rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business.
44:01 Opus 5.5 vs. GPT-6 Sol: the same-day price war
46:51 Gun to your head: open-weight models or frontier labs?
51:00 Secondaries: the top 30 names vs. everyone else
52:30 Why fintech and healthcare are unloved (and Jason's Robinhood bet)
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.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
Thank you to our partners:
(0:00) PARTNER - AD BLURB
(0:00) PARTNER - AD BLURB
(0:00) PARTNER - AD BLURB
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
Subscribe to our Substack Newsletters!
TWiST: https://twistartups.substack.com/
TWiAI: https://www.thisweekinai.ai/
TWiVC: https://thisweekinvc.substack.com/
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Elon's New Hyperloop, Trump's AI Rename, and a Model That Won't Talk | E2340
Monday, September 21, 2026 • Duration 01:09:39
This Week In Startups is made possible by:
Vanta: https://www.vanta.com/twist
DigitalOcean: http://do.co/twist
Lightfield: https://lightfield.app/
Plaud: http://Plaud.ai/twist
Today’s show:
Elon revives the Hyperloop, promising a 30-minute commute between Austin and San Antonio. It's the kind of project that could reshape how Texans think about getting between two major cities entirely. Then, Jason and Lon explain why this pitch is different from the other Boring Company tunnels.
Learn why President Trump wants to rename artificial intelligence itself and launch an "AI Force." It's a move that could reshape how the government talks about AI policy going forward. PLUS, a new startup's model refuses to write a single word of text, and it is 5 to 18 times faster with better accuracy. It's a completely different approach to how AI agents make decisions, and it might be a preview of where the industry heads next.
Relevant Links:
"Elon Musk's latest Boring Company pitch involves a Hyperloop between Austin and San Antonio" → https://techcrunch.com/2026/09/20/elon-musks-latest-boring-company-pitch-involves-a-hyperloop-between-austin-and-san-antonio/
The Boring Company → https://www.boringcompany.com/
Elon Musk's original 2013 Hyperloop white paper → https://www.tesla.com/sites/default/files/blog_images/hyperloop-alpha.pdf
Trump's Truth Social post proposing "Superior/Extreme/Supreme Intelligence" and announcing an AI Force and AI czar → https://www.unite.ai/trump-proposes-renaming-artificial-intelligence-announces-ai-force/
TechCrunch: "Trump says it's time to rebrand AI with a new name — and he's also creating an AI Force" → https://techcrunch.com/2026/09/19/trump-suggests-rebranding-ai-with-a-new-name-says-hes-also-creating-an-ai-force/
Vercel AI Open vs Closed Source Volume Chart → https://vercel.com/ai-gateway/leaderboards/models
TypeSafe AI — makers of Jev, the "System One Model" → https://typesafe.ai/
TypeSafe AI blog: "Introducing System One Models & Jev" → https://typesafe.ai/blog/introducing-system-one-models-and-jev
GeekWire: "Amazon blocks Meta's Muse AI assistant in new standoff over agentic shopping" → https://www.geekwire.com/2026/amazon-blocks-metas-muse-ai-assistant-in-new-standoff-over-agentic-shopping/
Meta's Muse — the AI agent Amazon blocked from shopping on its site → https://www.meta.ai/
"Meta's Dina Powell McCormick: The Case for Data Centers, Backlash, AI Job Boom & Meta's Future" (All-In Podcast, YouTube) — the clip discussed on the show → https://www.youtube.com/watch?v=qp2IbgJ5Z-8
Robocurve's RoboHarm report — the robot-safety benchmark discussed on air → https://robocurve.org/roboharm/
RoboHarm on GitHub (tasks, protocol, and tooling) → https://github.com/robocurve/roboharm
Timestamps:
0:00 Elon Musk revives the Hyperloop: a 30-minute Austin–San Antonio tunnel
1:03 A brief history of Hyperloop and the white paper
8:56 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
16:46 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!
20:32 DigitalOcean - 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%.
21:40 News: Trump proposes an "AI Force," an AI czar, and renaming AI itself
22:49 "Get back to work, nerds"
30:22 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
31:56 TypeSafe's Jev, a "System One" model built to decide, not chat
39:49 Amazon blocks Meta's Muse AI agent
49:57 Dina Powell McCormick's tense All-In Summit exchange with Jason
1:02:38 Off-Duty: Robocurve's RoboHarm benchmark
Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com
Check out the TWIST500: https://www.twist500.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
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Hugging Face Co-Founder on Open-Source, Microduck, and NVIDIA | E2339
Friday, September 18, 2026 • Duration 01:33:39
This Week In Startups is made possible by:
Superhuman: http://superhuman.com/ Paypal: http://paypal.launch.co Odoo: http://Odoo.com/twist Plaud: http://Plaud.ai/twist Harmonic: http://harmonic.ai/
Today’s show:
Hugging Face built a $399 open-source robot duck as a side quest, and sold 16,000 units off a single tweet. Co-founder Thomas Wolf joins Jason and Lon to explain Microduck happened, why storage is the company's real business, and what it felt like to get hacked by OpenAI's agents.
Jason takes apart Gavin Newsom's new AI "kill switch" executive order: if these models are so dangerous, why not start with the same KYC every bank already requires? PLUS, Snap’s new AI-integrated glasses could be a game-changer.
Guests:
Thomas Wolf on X: https://x.com/Thom_Wolf Hugging Face: https://huggingface.co/
Relevant Links:
Hugging Face — https://huggingface.co/
Microduck — https://pollen-robotics.com/microduck/
Pollen Robotics — https://pollen-robotics.com/
OpenAI: the Hugging Face incident and the road ahead — https://openai.com/index/hugging-face-incident-and-the-road-ahead/
Governor Newsom's executive order — https://www.wsj.com/tech/ai/californias-newsom-issues-executive-order-to-weigh-ai-oversight-including-kill-switch-3a98040f
Anthropic Wet Lab — https://www.cnbc.com/2026/09/18/anthropic-quietly-sets-up-biology-lab-as-it-ramps-ai-drug-program-report.html
Lucid and Bolt to deploy 25,000 autonomous EVs across Europe — https://electrek.co/2026/09/17/lucid-bolt-25000-autonomous-evs-europe/
Snap opens pre-orders for Specs at $2,195 — https://www.specs.com/
Ray-Ban Meta Display — the $799 comparison https://www.meta.com/ai-glasses/
Clavicular at All-In Summit — https://x.com/clavicular/status/2099994778616348811?s=20
Physical: 100 (the Korean original) → https://en.wikipedia.org/wiki/Physical:_100
Bad Therapy — https://www.abigailshrier.com/
Full Show Notes and Transcript from Pluad: https://web.plaud.ai/s/pub_194de893-8c55-4d77-81db-a6b278159a44::o9QfImqCq5VS0F_dqm4J93eTeyb-GsIeXCLwqASnvYAmt5f59OLQz5-VN1epnq6DBLoZWFales_7IbgC
Timestamps:
0:00 Guest: Thomas Wolf, co-founder & chief science officer, Hugging Face
1:58 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!
4:17 Two years to build Microduck
8:43 How Hugging Face actually makes money: storage, not tokens
10:16 Superhuman - Superhuman Go is an AI chat that's always there when you need it, already aware of what you're doing, and doesn't ask you to start from zero. Sign up to get the best in AI at https://superhuman.com
17:18 Vibe-coding robotics: "train this new behavior for me"
20:00 PayPal - Pay zero processing fees on your first $100K in eligible PayPal payment volume. Learn more at https://paypal.launch.co
23:20 Thomas Wolf's P-doom and the airplane-safety analogy
25:18 The Nvidia acquisition and what changes for open models
29:57 Odoo - The all-in-one business platform. Your first app is free! Get started today at https://Odoo.com/twist
38:39 Inside the Hugging Face breach: stolen credentials and basic mistakes
43:33 News: Newsom's executive order and the frontier-model "kill switch"
45:04 Jason's counter-proposal: liability, insurance, and KYC for AI
1:00:08 News: Lucid and Bolt to put 25,000 robotaxis on European roads
1:10:01 News: Snap opens pre-orders for $2,195 Specs AR glasses
1:21:43 Off-Duty: Clavicular, the All-In Summit
1:31:01 Off-Duty: Physical 100 goes to Italy and Mexico
Subscribe to TWiST on Substack: https://twistartups.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
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
90% of AI prototypes never reach production (w/ Temporal's Samar Abbas) | AI Basics
Tuesday, September 15, 2026 • Duration 19:22
The TWiST AI Basics series is made possible by Google for Startups!
Build context-aware AI workflows using DeepMind models and orchestration tools with Google for Startups' new Startup technical guide on generative media. Get the guide here: https://goo.gle/technical_guide
Today's show:
The demo works, the vibes are immaculate, but then the app falls apart the second real users touch it. On today's AI Basics, Temporal co-founder and CEO Samar Abbas says the problem isn't with the model at all. You're missing a harness, the layer that keeps an AI agent's work durable, secure, and recoverable if/when something breaks.
Temporal's durable execution platform is used by major companies from OpenAI to Stripe to Netflix, and helps to make their long-running software reliable and interruption-free.
On AI Basics, he explains why so many AI-coded prototypes die in the imagineering stage, before ever hitting production. Plus he walks Jason through Temporal's live dashboard, to show how it gives developers full visibility into what their agents are doing at every step.
Guest and Relevant Links:
Samar Abbas on X: https://x.com/SamarAtTemporal
Temporal: https://temporal.io/
Temporal raises $550M at a $12.55B valuation: https://temporal.io/blog/temporal-raises-usd550m-series-e-at-usd12-55b-valuation-ai
GeekWire: Samar Abbas on the "massive platform shift" in AI: https://www.geekwire.com/2026/temporal-ceo-samar-abbas-on-the-massive-platform-shift-in-ai-fueling-the-startups-5b-valuation/
Temporal expands Google Cloud partnership: https://temporal.io/blog/temporal-expands-google-cloud-partnership-with-pay-as-you-go-pricing
Timestamps:
0:00 Why every startup needs an AI harness
2:12 Why 90% of AI prototypes never reach production
4:16 What happens when an agent crashes mid-task
7:00 A look at Temporal's dashboard
13:02 OK but what is a "harness" exactly?
15:30 When to graduate an agent from laptop to production
17:44 Organizing agents into teams
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
Thank you to our partner!
Build context-aware AI workflows using DeepMind models and orchestration tools with Google for Startups' new Startup technical guide on generative media. Get the guide here:
https://goo.gle/technical_guide
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
Check out our suite of newsletters: https://substack.com/@thisweekininc
Follow TWiST:
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
Instagram: https://www.instagram.com/thisweekinstartups
TikTok: https://www.tiktok.com/@thisweekinstartups
Substack: https://twistartups.substack.com
Read more
Collapse
Related Shows Based on Content Similarities
Discover shows related to This Week in Startups, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
