This Week in Startups

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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!

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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?

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LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

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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!

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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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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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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!

Today’s show:

Elizabeth Holmes remains in prison for defrauding Theranos investors, even as she stars in the hit Nathan Fielder/Lance Oppenheim documentary “You Can See Everything.” But we’re asking the real question: After all the very public accusations… the hit pieces in the press and the Hulu drama series picking apart the scandal… would tech investors and VCs be willing to back her NEXT startup, if the numbers were right?

On today’s TWiST roundtable, Jason Calacanis is joined by Sam Lessin (Slow Ventures), Paige Finn Doherty (Behind Genius Ventures), and Jenny Fielding (Everywhere Ventures). In addition to reviews of the movie tech insiders can’t stop talking about, they cover why every seed portfolio needs a little bit of fraud, how diligence scales with check size, having trademark rights to your own voice, and the pro rata rights debate that’s still raging over Valar Atomics’ lawsuit with seed investors Day One Ventures.

Guests

Sam Lessin on X: https://x.com/lessin

Slow Ventures: https://slow.co/

Paige Finn Doherty on X: https://x.com/paigefinnn

Behind Genius Ventures: https://www.behindgeniusventures.com/

Jenny Fielding on X: https://x.com/jefielding

Everywhere Ventures: https://www.everywhere.vc/

Relevant Links

OpenSnow: https://opensnow.com/

“You Can See Everything” trailer: https://www.youtube.com/watch?v=HvW_N5p1q44

HBO Max “The Rehearsal” trailer: https://www.youtube.com/watch?v=2fjPFt8cpic

Elizabeth Holmes moves to halfway house in 2027 (ABC7): https://abc7.com/story/elizabeth-holmes-scheduled-move-halfway-house-august-2027/19862832/

Billy Evans’ blood-testing startup Haemanthus (TechCrunch): https://techcrunch.com/2025/05/10/elizabeth-holmes-partner-reportedly-fundraising-for-new-blood-testing-startup/

Polymarket: Oscars 2027 Best Picture: https://polymarket.com/event/oscars-2027-best-picture-winner-20260727173620857

Kalshi: Oscars 2027 Best Documentary: https://kalshi.com/markets/kxoscardocu/event/kxoscardocu-27

Charlie Javice sentenced to 7 years (NBC News): https://www.nbcnews.com/business/business-news/charlie-javice-sentenced-7-years-prison-fraudulent-175m-sale-financial-rcna234536

Trump pardons Nikola founder Trevor Milton (Axios): https://www.axios.com/2025/03/28/trump-pardons-nikola-founder-trevor-milton

Sequoia writes its FTX stake down to zero (Fortune): https://fortune.com/2022/11/10/ftx-sam-bankman-fried-sequoia-writes-down-214-million-investment-to-zero-venture-capital-crypto

Who lost money on Theranos? (Fortune): https://fortune.com/2018/05/04/theranos-investment-lost

“Barbarians at the Gate” on Amazon: https://www.amazon.com/Barbarians-Gate-Fall-RJR-Nabisco/dp/B08YP9MDHX

a16z backs Adam Neumann’s Flow (Commercial Observer): https://commercialobserver.com/2022/08/adam-neumann-350m-backing-andreessen-horowitz/

Martin Shkreli lifetime pharma ban (FTC): https://www.ftc.gov/news-events/news/press-releases/2022/01/statement-chair-lina-m-khan-ruling-judge-denise-l-cote-federal-trade-commission-et-al-v-vyera

Isaia Taylor post announcing Valar suit: https://x.com/isaiah_p_taylor/status/2108679133467414855

Day One Ventures response: https://x.com/mashadrokova/status/2108732979191390528

ElevenLabs Iconic Marketplace: https://elevenlabs.io/iconic-marketplace

Apple Corps vs. Apple Computer, a history (MacTech): https://www.mactech.com/2004/04/09/a-history-of-the-apple-vs-apple-dispute

Cameo for Business: https://www.cameo.com/business

Nox Metals: https://noxmetals.co

Electric Plant Company: https://www.electricplant.co/

Ablieration: https://abliteration.ai/

Timestamps:

0:00 Our new “This Week in VC” newsletter

2:15 Panel intro: Sam Lessin, Paige Doherty, Jenny Fielding

8:09 Why gambling loses appeal for VCs

11:02 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!

16:18 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%

17:35 Best moments from “You Can See Everything”

21:42 Unreliable narrators and unknowable situations

24:41 Living in a post-truth moment

30:02 Due diligence horror stories

32:45 Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist

34:50 The VCs remember their fraud investments

38:39 How LAUNCH trains founders to prep for diligence

44:31 How Elizabeth Holmes kept raising money

54:54 Would you invest in an Elizabeth Holmes company?

57:27 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.

1:02:28 Why seed funds need pro rata rights

1:09:02 When “founder friendly” means rolling over

1:16:25 The three investor relationships: team, founders, LPs

1:21:02 ElevenLabs “Archer” voice controversy

1:27:16 How NIL deals reshaped college sports

1:33:54 Cameo for Business and long-tail celeb endorsements

1:35:51 Portfolio company shoutouts

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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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Today’s show:
Jason can’t stop praising Nathan Fielder’s new A24 hybrid documentary about Elizabeth Holmes and Theranos, “You Can See Everything,” and he’s insisting that Lon check it out before the next podcast. Hear his spoiler-free review, how the film upended his expectations based on Fielder’s previous work, and why Lon also recommends Lance Oppenheim’s HBO Max series “Ren Faire.”
Plus, we’re talking to Clone Robotics co-founder and CEO Dhanush Radhakrishnan about why he thinks robots should not just be humanoid but should look and move precisely like humans. We’re digging deep into how his hydraulic myofiber artificial muscle technology alters and even improves on the pulley-based systems being deployed by competitors, why he thinks the models that power domestic helper-bots will be commoditized, and how quickly he thinks he can put a robo-butler in every American home.
Plus we’re comparing the potential impact of Anthropic’s new Public Benefit Fund vs. Elon Musk’s plan to give every baby a share of SpaceX, and re-considering simulation theory after Odyssey dropped an artificial fruit fly brain into an artificial landscape.
Guest
Dhanush Radhakrishnan on X: https://x.com/dhanushisrad
Clone Robotics: https://clonerobotics.com/
Related Links
“You Can See Everything” trailer: https://www.youtube.com/watch?v=HvW_N5p1q44
“You Can See Everything” on Rotten Tomatoes: https://www.rottentomatoes.com/m/you_can_see_everything
John Carreyrou’s Theranos investigation (Wall Street Journal): https://www.wsj.com/articles/theranos-has-struggled-with-blood-tests-1444881901
“Ren Faire” HBO Max trailer: https://www.youtube.com/watch?v=CHZUVTrrexE
“Nathan for You”: Smokers Allowed clip (Comedy Central): https://www.youtube.com/watch?v=HttB2fYAm-8
Anthropic: Investing in the Public Benefit: https://www.anthropic.com/news/public-benefit-fund
Elon Musk SpaceX pledge: https://x.com/elonmusk/status/2112089556615123114
Dell’s $6.25B Invest America commitment: https://www.onedell.com/investamerica/
Odyssey Fly Simulation X post: https://x.com/odysseyml/status/2111589148146749616
Chris Williamson: “The ElevenLabs Situation is Crazy”: https://www.youtube.com/watch?v=lxDNHLgWInU
ElevenLabs’ Legendary Voices marketplace: https://elevenlabs.io/iconic-marketplace
TWiST newsletter on Substack: https://twistartups.substack.com/
LAUNCH Careers page: https://careers.launch.co/
Timestamps:
00:00 Intro
00:10 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!
03:18 Jason's "You Can See Everything" reaction
14:37 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
15:27 What films max out RT's critic and audience scores
20:08 Anthropic commits 5% equity to Public Benefit Fund
24:28 Would equity change how Americans feel about AI?
27:08 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
38:38 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.
39:48 Dhanush from Clone Robotics joins the show
42:43 How hydraulic muscle technology actually works
54:55 When can we have our robot butlers please?
56:55 Where will Clone get its robot brains?
1:12:17 Odyssey trapped a fake fly brain in a simulated environment
1:23:09 Did ElevenLabs steal a podcaster's voice?
1:30:13 Check us out on Substack!
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