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This Week in Startups

Jason Calacanis
This Week in Startups
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  • This Week in Startups

    Odyssey CEO Oliver Cameron is 90% sure we live in a simulation | E2358

    2026-11-03 | 1 h 24 min.
    This Week In Startups is made possible by:

    Paper: https://getpaper.ai/twist

    G2i: https://G2i.co/twist

    Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain

    Plaud: https://Plaud.ai/twist

    Today’s show:

    Odyssey co-founder and CEO Oliver Cameron builds simulated worlds for a living, so we asked him the obvious question: are we all living in one, right now? He says he’s 90% certain that, yes, we are.

    To help make the case (and show off their world model technology), Oliver’s team dropped a simulated fruit fly brain into an AI world, that’s being rendered and created in real time. So far, on X, 6.2 million people have watched the virtual fly navigate an imaginary world.

    On TWiST, we’re digging into how world models learn about physics, gravity, and causality just by watching videos, what make Odyssey-3 an ideal trainig ground for AI agents, and why a world model only renders the parts of the world that are currently being experienced.

    It’s a peek inside the technology that may, one day, allow us to enslave people in The Matrix and turn them into batteries. Or train self-driving cars more effectively! One of those.

    Plus: SpaceX throttles Grok Bot over unsustainably high costs, but Jason says it’s worth every penny. And will OpenAI’s suggested name change from data centers to “compute campuses,” and Meta’s efforts to improve El Paso, help turn around American attitudes? Or is blasting them into space the only remaining viable option?

    Guest

    Oliver Cameron on X: https://x.com/olivercameron

    Odyssey: https://odyssey.systems/

    Relevant Links

    The fruit fly brain flying inside Odyssey-3 (6.2M views): https://x.com/odysseyml/status/2111589148146749616

    Meet Odyssey-3, Odyssey's foundation world model: https://odyssey.systems/meet-odyssey-3

    FlyWire: https://flywire.ai/

    Nick Bostrom, "Are You Living in a Computer Simulation?”: https://simulation-argument.com/simulation.pdf

    Do we live in a simulation? Chances are about 50-50 (Scientific American): https://www.scientificamerican.com/article/do-we-live-in-a-simulation-chances-are-about-50-50/

    "Beyond Perception: Proposing Our Reality as an ASI Alignment Simulation" (Ali Eslami, IPI Letters): https://ipipublishing.org/index.php/ipil/article/view/350

    The double-slit experiment explained (Royal Institution, Jim Al-Khalili): https://www.youtube.com/watch?v=A9tKncAdlHQ

    “A Glitch in the Matrix” trailer: https://www.youtube.com/watch?v=au8eT79WUJ0

    Elon Musk throttles Grok Bot limits over "unsustainably high" costs (TechCrunch): https://techcrunch.com/2026/11/02/elon-musk-throttles-grok-bot-limits-due-to-unsustainably-high-costs/

    Elon's post: "The cost of serving Grok Bot was unsustainably high relative to revenue”: https://x.com/elonmusk/status/2116992258520064397

    Jason's post: "< $40k a year on tokens… getting $2m+ in value": https://x.com/Jason/status/2117126320962351277

    Grok Bot: https://x.ai/bot

    Plaud Web: https://web.plaud.ai

    Founder University Japan: https://japan.founder.university/

    Most Americans say AI is bad for society and oppose more data centers (ABC/WaPo/Ipsos): https://abc7ny.com/story/most-americans-say-ai-is-bad-society-oppose-more-data-centers-abcpostipsos-poll/19964027/

    Chris Lehane's memo: AI will be the issue in 2028 (TNW): https://thenextweb.com/news/chris-lehane-memo-openai-2028-ai-election

    Meta touts El Paso water and grid pledges as council weighs incentives (KFOX): https://kfoxtv.com/news/local/meta-touts-10b-el-paso-data-center-water-and-grid-pledges-as-council-weighs-incentives

    UT Austin's Texas Advance Commitment (free tuition under $100K): https://admissions.utexas.edu/cost-aid/financial-aid/texas-advance-commitment/

    Andrej Karpathy's HackerTube post: https://x.com/karpathy/status/2116957135661945283

    Jason's "Unsponsored" Chrome extension for Amazon: https://x.com/Jason/status/2116380861167714594

    Google's first data center satellite is online and writing poetry (TechCrunch): https://techcrunch.com/2026/10/30/googles-first-data-center-satellite-is-online-and-writing-poetry/

    What is low Earth orbit? (Universe Today): https://www.universetoday.com/articles/what-is-low-earth-orbit

    Timestamps:

    0:00 Grok Bot users are at their limit

    3:36 How Jason and LAUNCH get $2M+ in value out of AI

    5:46 Jason’s Grok-made jacket lookbook

    10:35 Paper is the legal backbone for thousands of startup founders and fund managers - including Jason. Use https://getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta.

    14:12 Everything changed in AI over the last 90 days

    20:41 G2i has been recruiting software engineers for over a decade. Go to https://g2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    22:06 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!

    22:37 Wiring our Plaud into our Grok Bot

    23:24 Odyssey’s fruit fly video zooms to 6.2M views

    27:32 All About Simulation Theory

    34:34 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

    38:33 What is the double slit experiment?

    40:47 How to teach a robot about physics

    50:01 OpenAI’s plan to make Americans love data centers

    56:53 Meta’s El Paso data center pitch

    1:02:26 AI companies should overfund local schools

    1:06:27 Karpathy’s HackerTube project

    1:13:02 Google’s first space data center goes online

    1:17:51 How much room is there in low Earth orbit?

    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

    Thank you to our partners:

    Paper is the legal backbone for thousands of startup founders and fund managers - including Jason. Use https://getpaper.ai/twist to get your cap table free for a year - or two years if you're leaving Carta.

    G2i has been recruiting software engineers for over a decade. Go to G2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    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

    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!

    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
  • This Week in Startups

    Binance Hacked $6.3B Stolen, DoorDash Buys Instacart For $17B, Jake Newfield from Hermetiq, + More!

    2026-10-30 | 1 h 10 min.
    This Week In Startups is made possible by:

    Stripe: https://stripe.com/startups

    Rippling: https://rippling.ai/twist

    Northwest Registered Agent: https://www.northwestregisteredagent.com/twistdomain

    Plaud: https://plaud.ai/twist

    Today’s show:

    Binance lost an estimated $6.3 billion in the biggest crypto hack ever, and Jason proposes a radical solution. The entire tech industry should stop shipping new features for one month a year, and do nothing but patch. (Call it No App November?)

    On a busy Friday show, Jason and Lon dig into the. Binance breach and look back at Jason’s prescient 2021 warning about leaving your money in crypto exchanges. (He recommends spreading your wealth around various different banks!) Plus, why he’s giving CZ credit for backstopping customer losses out of his own fortune.

    Plus, DoorDash’s $17B acquisition of Instacart… Did DoorDash overpay? And is this happening now to avoid the harsher regulatory climate should Democrats regain power in the midterms?

    Then we’ve got Hermetiq co-founder and CEO Jake Newfield, who has twice won the LAUNCH Accelerator’s pitch competition. Hear the celebrated two-minute pitch for an AI build engineer, and find out why Jason thinks having a “lighthouse customer” makes such a huge difference.

    Finally, we’re awarding the Grand Prize in our $5K bounty competition to create Jason’s Annotated app, and remembering the legendary film and TV actor Sir Patrick Stewart.

    Guest

    Jake Newfield on LinkedIn: https://www.linkedin.com/in/jakenewfield/

    Hermetiq: https://www.hermetiq.com/

    Bazel: https://bazel.build

    Apply to the LAUNCH Accelerator: https://www.launch.co/apply

    Relevant Links

    Binance links the $6.3B theft to a compromised DevOps laptop (BleepingComputer): https://www.bleepingcomputer.com/news/security/binance-links-63-billion-crypto-theft-to-compromised-devops-laptop/

    The 1978 Lufthansa heist (History.com): https://www.history.com/articles/1978-lufthansa-heist-jfk-henry-hill-goodfellas

    Trump pardons Binance founder Changpeng Zhao (KWTX/AP): https://www.kwtx.com/2025/10/23/trump-pardons-binance-founder-changpeng-zhao

    CrowdStrike: https://www.crowdstrike.com/en-us/

    Palo Alto Networks: https://www.paloaltonetworks.com/

    Grant Cardone challenges Jason to $1M Bitcoin bet: https://www.thestreet.com/crypto/markets/grant-cardone-challenges-bitcoin-bear-to-1-million-bet

    DoorDash to acquire Instacart for $17B (TechCrunch): https://techcrunch.com/2026/10/29/doordash-to-acquire-instacart-for-17b/

    Economic Liberties calls on the FTC to block the deal: https://www.economicliberties.us/press-release/economic-liberties-calls-on-ftc-to-block-doordash-instacart-merger/

    Central Market, H-E-B's upscale banner, expands home delivery (Supermarket News): https://www.supermarketnews.com/foodservice-retail/central-market-expands-curbside-and-home-delivery

    People are using AI to make their smart TVs dumb again (TechCrunch): https://techcrunch.com/2026/10/19/people-are-using-ai-to-make-their-smart-tvs-dumb-again/

    TWiST $5K Bounties: https://bounty.thisweekinstartups.com/

    Founder University: https://founder.university/

    Founder University x Japan: https://japan.founder.university/

    Inside.com domain auction: https://inside.com/

    Yank Sing: https://yanksing.com/

    Cafe du Monde coffee and chicory: https://shop.cafedumonde.com/product/coffee-beignets/cafe-du-monde-coffee-and-chicory

    Patrick Stewart, "Star Trek" and "X-Men" actor, dead at 86 (CNN): https://www.cnn.com/2026/10/29/entertainment/patrick-stewart-death

    “Time Squared” (Star Trek: TNG S2E13): https://memory-alpha.fandom.com/wiki/Time_Squared_(episode)

    “Green Room” trailer: https://www.youtube.com/watch?v=Q8XSARX3DQg

    “X-Men: Days of Future Past” trailer: https://www.youtube.com/watch?v=pK2zYHWDZKo

    Timestamps:

    0:00 The largest crypto hack or theft in history

    5:45 Jason gives CZ credit for backstopping losses

    7:34 Jason’s cybersecurity proposals

    11:48 Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on https://stripe.com/startups.

    14:49 DoorDash buys Instacart for $17B

    18:48 Is DoorDash overpaying?

    24:28 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.

    26:26 Vibecoding your smart TV

    27:20 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!

    30:04 Jake Newfield (Hermetiq) gives a perfect pitch

    34:13 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

    37:12 Lead with your lighthouse customer

    43:14 The Cafe Du Monde branding lesson

    51:10 The Annotated Bounty finals begin

    1:04:00 Jason announces the grand prize winner

    1:07:34 RIP Sir Patrick Stewart

    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

    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
  • This Week in Startups

    Is AI the new cigarettes? Our VC panel digs into Anthropic’s S-1 | E2356

    2026-10-29 | 1 h 12 min.
    This Week In Startups is made possible by:

    PayPal: https://paypal.com/business

    The Conservation Fund: https://www.conservationfund.org/

    Hostinger: https://hostinger.com/twist

    Plaud: https://plaud.ai/twist

    Today’s show:

    Anthropic’s S-1 is here, and finally, we can start to develop a real understanding for the AI economy and whether the numbers add up. Anthropic shows an operating profit, a mostly non-cash $80.7 billion loss, and customers spending a shocking 9x what they were spending on intelligence just one year ago.

    Is this the greatest business in history? Is AI now as addictive to enterprises as cigarettes once were to impressionable teens?

    On this week’s VC Roundtable, Jason Calacanis is joined by D.A. Wallach (Time BioVentures), Dave McClure (Practical Venture Capital), and Ben Black (Akkadian Ventures / Powerlaw Corp.) to seek some answers.

    They dig into the numbers, including that wild 900% net revenue retention, and consider how retail investors will consider the convertible-note charge behind their $80B loss. Plus they’ll debate whether Anthropic’s founders are really true believers driven by religious fervor, and if so, whether they’re destined to be out-competed by “rabid capitalists.”

    Guests

    D.A. Wallach on X: https://x.com/dawallach

    Time BioVentures: https://www.timebioventures.com/

    Dave McClure on X: https://x.com/davemcclure

    Practical Venture Capital: https://practicalvc.com/

    Trading Places podcast: https://www.youtube.com/@PracticalVentureCapital

    Ben Black on LinkedIn: https://linkedin.com/in/benblack

    Akkadian Ventures: https://akkadian.vc/

    Powerlaw Corp: https://pwrl.com

    Relevant Links

    Anthropic’s S-1, by the numbers (Fortune): https://fortune.com/2026/10/27/anthropic-s1-ipo-filing-financials-profits/

    900% NRR and an $80.7B loss that mostly ins’t (HackerNoon): https://hackernoon.com/anthropics-s-1-shows-163b-in-half-year-revenue-a-900percent-nrr-and-an-807b-loss-that-mostly-isnt

    Tickertrends: https://tickertrends.io/

    Replit makes OpenAI its default (TechCrunch): https://techcrunch.com/2026/10/17/replit-is-no-longer-working-with-anthropic-ceo-says/

    Dario Amodei warns that rivals’ spending could risk bankruptcy (Fortune): https://fortune.com/2026/02/14/anthropic-ceo-dario-amodei-spending-capex-risk-ai-revenue-forecasts-bankruptcy

    Machines of Loving Grace (Dario Amodei): https://www.darioamodei.com/essay/machines-of-loving-grace

    Palantir CTO Shyam Sankar says AI researchers are taking up smoking (Fortune): https://fortune.com/2026/10/13/palantir-cto-shyam-sankar-ai-researchers-smoking-cigarettes-cure-cancer-artificial-general-intelligence-silicon-valley-mass-psychosis-effective-altruism/

    Microsoft offers its first-ever voluntary buyouts (TechSpot): https://www.techspot.com/news/112174-microsoft-offers-voluntary-buyouts-thousands-us-workers-ai.html

    Canva ranks among the top consumer AI apps (SmartCompany): https://www.smartcompany.com.au/artificial-intelligence/canva-new-ai-consumer-web-app-ranking-andreesen-horowitz/

    SpaceX Q3: Musk says it could rent out its AI compute several times over (Constellation Research): https://www.constellationr.com/insights/news/spacexs-q3-musk-says-it-could-rent-out-its-ai-compute-several-times-over

    Jason’s 2026 “Bitcoin is Dead” post: https://x.com/Jason/status/2114956980674605075

    Jason to Michael Saylor: "there are better places to invest your money”: https://x.com/Jason/status/2115274438979756346

    Timestamps:

    0:00 Anthropic files its public S-1

    4:58 Anthropic vs. OpenAI revenue run rates

    9:20 PayPal is built for all businesses. Get started at https://paypal.com/business

    10:02 “The greatest business in the history of capitalism”

    11:58 Is intelligence the new tobacco?

    18:08 The “meat sack constraint”

    20:36 Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/

    22:13 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!

    24:32 The Who Has the Most Subscribers Challenge

    28:08 Is Apple waiting out the AI race on purpose

    30:22 Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday

    34:19 Is Canva an AI company?

    39:08 True Believers who still want to make money

    48:21 The $72.4B convertible-note charge, explained

    51:03 How long does AI compute stay useful?

    58:19 Jason’s monthly “Bitcoin is Dead” post

    1:04:41 Alicorns are unicorns with pegasus wings

    1:09:58 Subscribe to the TWiST Newsletter!

    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:

    PayPal is built for all businesses. Get started at https://paypal.com/business

    The Conservation Fund: Thanks to our partner, The Conservation Fund! Learn more at https://www.conservationfund.org/

    Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to https://hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday

    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!

    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

    Pregame Your Launch Before Your App Exists (w/ Amanda Bradford) | E2355

    2026-10-26 | 56 min.
    This Week In Startups is made possible by:

    Odoo: https://odoo.com/twist

    G2i: https://g2i.co/twist

    Rippling: https://rippling.ai/twist

    Plaud: https://plaud.ai/twist

    Today’s show:

    Amanda Bradford’s “launch party” for her dating app The League actually extended for months.

    She “pre-gamed” the app’s formal launch with months of mixers, boat parties, and free events, where the only ticket required for admission was having the app on your phone.

    By launch day, she had a massive wait list, and still just let in 500 people, who ensure maximum buzz (and FOMO).

    At LAUNCH’s first-ever Tactical & Practical live event from San Francisco, Amanda walks the crowd through how she built a vetted, two-sided dating marketplace as a solo founder, eventually getting prominent enough to attract the attention of Match Group. (She sold The League for ~$30 million in 2020.)

    Hear exclusive tips you won’t get anywhere else, like how Amanda used a “fake paywall” to gauge willingness to pay for subscriptions, and how to time your rate of expansion into new markets.

    Plus, an all-new Flashback segment, featuring Alex and Lon looking back at a classic 2017 interview between Jason and Stripe’s Patrick Collison.

    Guests

    Amanda Bradford on X: https://x.com/amandabradford

    Book a Call with Amanda: https://intro.co/amandabradford

    The League: https://www.theleague.com/

    Patrick Collison on X: https://x.com/patrickc?lang=en

    Stripe: https://stripe.com/

    Relevant Links:

    The League was called "elitist." Its founder says that was never the case (CNBC): https://www.cnbc.com/2023/10/20/founder-of-the-league-on-dating-ambition-and-that-viral-ad-campaign.html

    Alex Wilhelm’s Cautious Optimism: https://www.cautiousoptimism.news/

    TWiST E723: Patrick Collison (2017): https://www.youtube.com/watch?v=P-NepiMQGvY

    Timestamps:

    0:00 Amanda Bradford on building The League

    4:30 Hand-reviewing early applications

    6:40 Building an MVP with a rented co-founder

    8:56 The VIP approach

    13:10 Why Amanda only let in 500 people

    15:44 The “Heavy Hitter” fake paywall test

    16:44 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist

    17:46 Why live events are the real unlock

    21:35 Controversy as a hook

    24:22 Flashback to Patrick Collison in 2017

    25:13 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!

    28:13 Stripe: Then vs. Now

    30:53 G2i has been recruiting software engineers for over a decade. Go to https://g2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    32:17 Why did PayPal stay PayPal?

    37:50 Problem, not a product

    44:33 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.

    45:46 The outage nobody noticed

    51:00 Why persistence beats pivoting

    52:13 What’s left before a Stripe IPO?

    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

    Thank you to our partners:

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

    G2i has been recruiting software engineers for over a decade. Go to G2i.co/twist to find out how G2i vets engineers, and can help you hire them in days, not weeks.

    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.

    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!

    Check out all our partner offers: https://partners.launch.co/
  • This Week in Startups

    OpenAI’s $1.25T Raise, Starlink Mobile & Zuck’s Tax Deal | EP 2354

    2026-10-24 | 1 h 33 min.
    This Week In Startups is made possible by:

    Plaud - https://plaud.ai/twist

    Sentry - https://sentry.io/twist

    Lightfield - https://lightfield.app

    Rippling - https://rippling.ai/twist

    Today’s show:

    Is OpenAI finally priced correctly? Jason argues that the reported $30 billion raise at a $1.25 trillion valuation is finally “right-sized.” He also says that he’d put money in at that price, while walking through the risks that could still sink the investment.

    It’s a Friday all-news episode with Jason and Lon, covering OpenAI’s latest round, SpaceX’s push to become America’s fourth major carrier, Zuck and Meta’s creative move around the proposed California billionaire tax, and some of Lon and Jason’s favorite documentaries.

    Plus we’re asking the timely question: who watches the AI watchdogs?

    Relevant Links

    OpenAI nears up to $30B round at $1.25T valuation, led by UAE investors (CNBC): https://www.cnbc.com/2026/10/22/openai-funding-round-uae-investors.html

    Anthropic investors eye a $2T IPO (Nasdaq): https://www.nasdaq.com/articles/move-over-spacex-anthropic-targets-2-trillion-valuation

    Uber puts all 30,000 employees on ChatGPT Work (TechCrunch): https://techcrunch.com/2026/10/22/uber-puts-all-30000-employees-on-chatgpt-work/

    Telecom stocks fall as SpaceX eyes 80,000 cell sites (Yahoo Finance): https://finance.yahoo.com/markets/stocks/articles/telecom-stocks-fall-spacex-eyes-134838815.html

    Verizon launches simpler plans and drops activation and upgrade fees (Fox Business): https://foxbusiness.com/markets/verizon-launches-simpler-plans-new-loyalty-program-drops-some-fees

    Amazon Leo's launch slips past early 2026 (ITdaily): https://itdaily.com/news/network/amazon-leo-faces-delays/

    METR and Redwood Research's write-up on red-teaming OpenAI's agent monitoring: https://metr.org/blog/2026-10-22-red-teaming-openai-agent-monitoring/

    Open Philanthropy is now Coefficient Giving: https://coefficientgiving.org/research/the-story-behind-our-new-name/

    Court documents show the alleged FSU shooter's ChatGPT chats (AOL): https://www.aol.com/news/court-documents-show-florida-state-233829466.html

    Meta's 8-K filing on the Founder Alignment Agreement (SEC): https://www.sec.gov/Archives/edgar/data/0001326801/000162828026066700/meta-20261019.htm

    Polymarket: will California's billionaire tax pass?: https://polymarket.com/event/billionaire-one-time-wealth-tax-passes-in-california-election-2026

    Mark Cuban vs. Ro Khanna on the billionaire tax (Fortune): https://fortune.com/2026/08/17/mark-cuban-california-billionaires-tax-wealth-ro-khanna/

    Elizabeth Holmes: The Theranos Deception (60 Minutes archive): https://cbsnews.com/video/elizabeth-holmes-the-theranos-deception-60-minutes-archive

    “The Act of Killing” trailer: https://www.youtube.com/watch?v=Q3FcB1UZHlg

    “Grizzly Man” trailer: https://www.youtube.com/watch?v=uWA7GtDmNFU

    “Hoop Dreams” trailer: https://www.youtube.com/watch?v=uf9Nq2ju0t0

    “The King of Kong” trailer: https://www.youtube.com/watch?v=L5XvArGGIzk

    “A Short Stay in Hell” by Steven L. Peck: https://www.amazon.com/dp/0983748446

    “The Library of Babel” by Jorge Luis Borges [PDF]: https://sites.evergreen.edu/politicalshakespeares/wp-content/uploads/sites/226/2015/12/Borges-The-Library-of-Babel.pdf

    “The Eureka Machine” by Richard Socher: https://www.amazon.com/dp/154170570X

    Timestamps:

    0:00 Jason’s in SF with the LAUNCH Accelerator 37 cohort

    2:40 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!

    6:34 Tactical & Practical talks live at Salesforce Tower

    10:21 Using Claude for brainstorming, not writing

    19:26 Sentry - New users can get $240 in free credits when they go to https://sentry.io/twist and use the code TWIST26

    20:42 OpenAI closing $30B at a $1.25T valuation

    26:04 Why OpenAI could still lose

    30:25 Would you put 30% of your retirement into OpenAI?

    32:34 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

    34:27 Every Tesla becomes a Starlink hotspot

    43:06 What would be the ultimate SpaceX domain name?

    45:00 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.

    46:10 Is METR a fair watchdog for OpenAI?

    54:03 Jason’s “Know Your Customer” plan for AI models

    1:03:34 Meta’s deal to keep Zuckerberg in Cali

    1:14:35 Why Jason would raise the minimum wage

    1:18:42 Does Nathan Fielder give Liz Holmes a pass?

    1:30:59 “A Short Stay in Hell” and “The Eureka Machine”

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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.
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