1494 episodes
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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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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!
Check out all our partner offers: https://partners.launch.co/ - This Week In Startups is made possible by:
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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”
Subscribe to our newsletters on Substack:
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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
Follow TWiST:
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Odoo: The all-in-one business platform. Your first app is free! Get started today at https://odoo.com/twist
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
Subscribe to our newsletters on Substack:
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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
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Substack: https://twistartups.substack.com Anthropic Gives Away 5% of Its Shares, Clone’s Muscle Robot, ElevenLabs Steals Podcaster's Voice
20/10/2026 | 1h 34 mins.This Week In Startups is made possible by:
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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!
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:
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Today’s show:
Today’s college grads are showing up to work at Jason’s company unable to write three sentences. He’s asking what Shishir Mehrotra of Superhuman, the company behind Grammarly, can do to fix that.
Shishir delves into Superhuman’s reasons for acquiring GPTZero, the most popular AI detector, and the AI notetaker Fathom, and the spreadsheet startup Rows. Plus, how Shishir responds to accusations that Grammarly helps students cheat in the classroom, why writers should disclose when they’re collaborating with an LLM, and Jason's CEO wish list for fresh Grammarly features.
In the news, Tesla demoed its long-awaited Roadster, which used SpaceX thrusters to do some flips and propel itself over five other Teslas… And OpenAI warned staffers that spies may be trying to seduce them in order to steal company secrets… And the shutdown of Character AI prompts Jason to declare: “AI relationships are evil.”
Guests:
Shishir Mehrotra on X: https://x.com/shishirmehrotra Superhuman: https://superhuman.com
Relevant Links:
Rows, the spreadsheet startup Superhuman bought, announces the deal → https://rows.com/blog/post/rows-is-joining-superhuman
Superhuman to acquire GPTZero (Business Wire) → https://www.businesswire.com/news/home/20260623083788/en/Superhuman-to-Acquire-GPTZero-AI-Authenticity-Platform
Is the Internet AI, GPTZero's live tracker of AI content on Reddit, LinkedIn and X → https://istheinternetai.com
GPTZero AI Vision, the extension that flags AI posts as you browse → https://gptzero.me/ai-vision
Superhuman acquires YC-backed notetaker Fathom (TechCrunch) → https://techcrunch.com/2026/09/14/superhuman-acquires-yc-backed-notetaker-fathom-as-productivity-platforms-push-for-agentic-work/
Grammarly Authorship, which shows how much of your writing came from AI → https://www.grammarly.com/authorship
GPTZero Authorship and Writing Replay → https://gptzero.me/authorship
Stanley Druckenmiller says his WSJ op-ed was written with AI (NOTUS) → https://www.notus.org/media/stanley-druckenmillers-wsj-op-ed-bessent-ai
Superhuman Go, the AI assistant that works wherever you type → https://superhuman.com/go
Tesla reveals its new Roadster with SpaceX thrusters (TechCrunch) → https://techcrunch.com/2026/10/15/tesla-reveals-spacex-powered-roadster-that-flies-and-falls-with-style/
OpenAI employee arrested over a hidden listening device in an executive conference room (NBC News) → https://www.nbcnews.com/tech/tech-news/openai-employee-arrested-hidden-listening-device-company-says-rcna603262
Eight states sue OpenAI over ChatGPT's alleged harm to kids (NBC News) → https://www.nbcnews.com/tech/tech-news/openai-sued-eight-states-alleged-harm-chatgpt-rcna603614
Timestamps:
00:00:00 Intro
00:07:14 GPTZero and the fight over what's human
00:09:27 How much of Reddit, LinkedIn and X is AI
00:10:56 Fathom and the 90% of work that's spoken
00:12:05 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/
00:16:27 Why Jason says every employee should use Grammarly
00:18:04 How to test whether new hires can actually write
00:22:08 Every - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io/.
00:24:22 Grammarly Authorship and proving the work is yours
00:25:53 How accurate are AI detectors
00:30:36 Jason wants AI writing flagged by default
00:32:34 Enforcing Grammarly and Go across a whole team
00:36:45 PayPal - PayPal is built for all businesses. Get started at https://paypal.com/business
00:37:28 Assist, chat and do, three kinds of AI agents
00:41:06 Jason's feedback on the Grammarly keyboard
01:13:27 Tesla demos the Roadster on SpaceX thrusters
01:21:20 OpenAI engineer charged with bugging an executive conference room
01:21:43 Why OpenAI warned employees about foreign spies
01:27:57 Eight states sue OpenAI over harm to kids
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
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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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About This Week in Startups
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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