This Week in Startups
This Week in Startups

This Week in Startups

Jason Calacanis

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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.

Recent Episodes

Why SpaceX Buying Cursor Changes Everything
JUN 18, 2026
Why SpaceX Buying Cursor Changes Everything
This Week In Startups is made possible by:Deel - deel.com/twistLinkedIn - linkedIn.com/twistNorthwest Registered Agent - northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twistToday’s show:Anthropic stabbed Cursor in the back. Then SpaceX swooped in with $60 billion. Today, TWiST connects the dots on the biggest deal in AI since the Microsoft-OpenAI partnership, and why it's a warning sign for every startup building on top of a frontier model. Jason is joined by Bling Capital’s Ben Ling, Banana Capital’s Turner Novak, and co-host Alex to go deep on the future of coding models, the current golden age of venture liquidity, OpenAI’s financials, and the ‘Four Ds’ of venture investing. The show closes with a tribute to Josh Baer, the founder of Capital Factory.Guest Links:Ben Ling https://x.com/bling0?lang=enBling Capital https://www.blingcap.com/Turner Novak https://x.com/TurnerNovakBanana Capital https://www.bananacapital.vc/Show Links:Hanover Park https://www.hanoverpark.com/SpaceX buys Cursor https://www.cnbc.com/2026/06/16/spacex-spcx-cursor-acquisition-ipo.htmlCursor Composer 2.5 https://cursor.com/blog/composer-2-5OpenAI financials source https://www.wheresyoured.at/exclusive-openai-financials/AMD’s new deskside data center https://www.amd.com/en/products/processors/desktops/ryzen/ryzen-ai-halo.htmlPerplexity Model Council https://www.perplexity.ai/hub/blog/introducing-model-councilTimestamps:0:00 Guest introductions1:15 Guest introductions2:43 SpaceX acquires Cursor for $60B6:13 The golden era of M&A9:13 Northwest Registered Agent: Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist12:04 Cursor's negative gross margins & the compute problem13:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!15:04 Rolling your own model: When does it make sense?19:35 LinkedIn: Thanks to our partners at LinkedIn! Post your job for free at https://linkedIn.com/twist then promote it to get access to LinkedIn Jobs' new AI assistant.22:53 The "headless product" thesis28:31 Deel: Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.34:22 OpenAI financials leaked: $13B revenue, $38.5B net loss40:13 Where does AI value accumulate?45:34 Portfolio Spotlight: Hanover Park48:37 Seed stage graduation rates have fallen from 50% to 25%54:59 The four Ds of venture: Deal flow, Decisions, Doubling down, Distributions1:06:36 How to find 'undiscovered gems'1:30:59 Snap Specs AR glasses: $2,195, and a bit chunky1:39:29 Tribute to Joshua Baer, Capital Factory's founderSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisCheck 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 McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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101 MIN
The Startup Building the First Hotel on the Moon…
JUN 15, 2026
The Startup Building the First Hotel on the Moon…
This Week In Startups is made possible by:Every.io - visit every.ioSentry.io - sentry.io/twistVanta - vanta.com/twistToday’s show:The next SpaceX won't be building rockets; it'll build the first hotel on the Moon. Today on TWiST, GRU Space founder Skyler Chan brings a brick made from lunar soil into the studio and lays out a plan to manufacture on the Moon as early as next year. We get into the science, the business model, and the regulatory land-grab ahead!Then, the US government forces Anthropic to pull Fable 5 and Mythos 5. Jason and Lon unpack what it means when a single AI model can vanish overnight, and the US government's emergency order.Stick around for the winner (or winners?!) of the $5,000 AI podcast-companion bounty!Timestamps:0:00 Knicks playoff run, San Antonio & Texas BBQ (Black's vs. Terry Black's)8:23 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!9:52 Guest intro: Skyler Chan, GRU Space — and the lunar-soil brick10:29 Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io12:14 Why the next SpaceX builds habitats, not rockets15:18 NASA's $20B moon-base signal & the TRL contracting path16:13 Business model: from construction contractor to owning lunar land18:06 Building the hotel robotically + $1M refundable deposits20:00 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 TWIST31:09 Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist39:28 News: US government blocks Anthropic's Fable 5 & Mythos 541:34 The politics: Hegseth, Sacks, Jassy & the "conspiracy" angle1:09:39 Why no single model dependency is safe (multi-model harnesses)1:18:47 Bounty results: MySidecast wins $3,0001:19:07 Honorable mentions: Couchverse (Lemon Slice) & Convalenz1:29:44 Next bounty: the Annotated app🔗 Links & Resources Mentioned:Guest & companySkyler Chan: Founder, GRU Space → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-spaceGRU Space (Galactic Resource Utilization): YC startup building lunar-regolith bricks and a robotic Moon hotel → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-spaceGRU Space lunar hotel bookings → https://payloadspace.com/gru-space-opens-bookings-for-planned-lunar-hotel/🎙️ About the Guest:Skyler Chan is the founder of GRU Space (Galactic Resource Utilization), a Y Combinator–backed startup developing a payload factory that manufactures bricks from lunar regolith to build the first robotic hotel on the Moon.Follow GRU Space → https://www.ycombinator.com/companies/galactic-resource-utilization-space-inc-gru-spaceSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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100 MIN
SpaceX IPO Day: What Wall St. and the media missed | E2300
JUN 13, 2026
SpaceX IPO Day: What Wall St. and the media missed | E2300
This Week In Startups is made possible by:Plaud https://Plaud.ai/twistPilot https://pilot.com/twistAgree https://agree.comIM8 Health https://IM8health.com/twistAfter watching Elon build out his rocket (and AI) company over the past 20 years, Jason celebrates the SpaceX IPO on a new TWiST. He explains why some investments are evaluated based on earnings and current numbers, while other stocks are bets on expensive visions for the future, and why SpaceX why likely pay off across multiple time horizons.PLUS Polsia solo founder Ben Cera is back with guidance for founders on creating a “Purple Cow”: a unique experience that makes their brand memorable.Guest:Ben Cera on X: https://x.com/BenceraPolsia: https://polsia.com/Polsia on X: https://x.com/polsiaBen on TWiST E2256 (Feb 2026): https://www.youtube.com/watch?v=QCce8e02IswRelevant Links:SpaceX: https://www.spacex.com/SPCX on Yahoo Finance: https://finance.yahoo.com/quote/SPCX/Starlink: https://www.starlink.com/Planet Labs: https://www.planet.com/Palantir: https://www.palantir.com/Valor Equity Partners: https://www.valorep.com/Seth Godin’s “Purple Cow” on Amazon: https://www.amazon.com/Purple-Cow-New-Transform-Remarkable/dp/1591843170Uber Ice Cream stunt article: https://finance.yahoo.com/news/ubers-brilliant-marketing-stunt-hail-195946535.htmlHillsborough Flintstones House article: https://www.sfgate.com/travel/article/The-Flintstone-House-is-now-for-rent-on-Airbnb-10420107.php“19 Hours Inside the Airbnb X-Mansion” article: https://www.theringer.com/2024/05/29/pop-culture/x-mansion-airbnb-x-men-icons-experienceWas The Pepsi Challenge based on LIES? https://www.historyoasis.com/post/the-pepsi-challengeCloudKitchens: https://cloudkitchens.com/Cluely: https://cluely.com/Timestamps:0:00 SpaceX IPO details2:12 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!7:21 The voting vs. weighing investment framework9:41 Pilot: Focus on your product, let Pilot handle your bookkeeping. Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses. Head to https://pilot.com/twist and get $1,200 off your first year.19:53 Agree - Stop chasing invoices at https://agree.com and tell them Jason sent you to get 50% off for life!22:25 The media's SpaceX criticisms and "hot takes"23:54 Ben Cera of Polsia is back26:53 Why Jason says no to a free tier29:10 IM8 Health: Start feeling like your best self every day. Go to https://IM8health.com/twist and use the code TWiST to get a free welcome kit, five free travel sachets, and 10% off your order.34:27 The wisdom of Seth Godin's "Purple Cow"50:37 The "Pepsi Challenge" model1:05:45 Lon got a dog, Jason got routers1:10:37 The YouTuber to movie theater pipeline1:15:20 Jason's new favorite travel bagSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisCheck 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 McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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79 MIN
Why the most expensive Seed deals are the cheapest | E2299
JUN 10, 2026
Why the most expensive Seed deals are the cheapest | E2299
This Week In Startups is made possible by:NetSuite - Netsuite.com/TWiSTDeel - Deel.com/TWiSTSquarespace - Squarespace.com/TWiSTTwo days before SpaceX launches the largest IPO in history at a flat $135/share, our VC roundtable drops a scorcher: The top 1% of seed deals might actually be underpriced. Plus: the "Sequoia scam" dual-tranche controversy, tokens-for-equity deals, and whether Claude Fable 5 is a true step function.Tomasz Tunguz (Theory Ventures), Michael Downing (Castalia Capital), and Paige Doherty (Behind Genius Ventures) join Alex to go deep on Seed investing, startup economics, AI spend, and the impact of smarter AI on the founder journey.Guest Links:Tomasz Tunguz: https://x.com/ttunguzTheory Ventures: https://theoryvc.com/Michael Downing: https://www.linkedin.com/in/michaeldowning/Castalia Capital: https://castalia.capital/Paige Doherty: https://x.com/paigefinnnBehind Genius Ventures: https://www.behindgeniusventures.comShow Links:Anthropic’s IPO announcement: https://www.anthropic.com/news/confidential-draft-s1-secOpenAI’s IPO announcement: https://openai.com/index/openai-submits-confidential-s-1/Bending Spoons F-1 filing: https://www.sec.gov/Archives/edgar/data/2004711/000110465926071170/tm2613674-7_f1.htmSpaceX IPO filing: https://www.sec.gov/Archives/edgar/data/1181412/000162828026040364/spaceexplorationtechnologib.htmBrendan Foody’s post on Sequoia: https://x.com/BrendanFoody/status/2063470286515683759Claude Fable 5: https://www.anthropic.com/news/claude-fable-5-mythos-5OpenRouter data on Chinese models: https://openrouter.ai/rankings?view=daySaronic: https://www.saronic.com/MotherDuck: https://motherduck.com/Nox Metals: https://noxmetals.co/Timestamps:0:00 Tomasz Tunguz, Michael Downing & Paige Doherty join2:07 The SpaceX IPO and the IPO window4:22 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!6:30 The new bar: 10x growth (not 3x) to raise a great Series A8:46 Net-new AI budgets9:46 Squarespace: Turn your idea into a beautiful website! Go to https://www.squarespace.com/twist for a free trial. When you're ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.11:09 How some founders are outgrowing venture capital11:44 The power pendulum swings back to founders12:46 SpaceX vs. OpenAI vs. Anthropic: Which IPO is most enticing?19:53 Deel - Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, get visas handled fast, and get back to building. Visit https://deel.com/twist to learn more.26:07 Tokens-for-equity, GPU-hours-for-equity & the financialization of compute28:35 Founders airing VC dirty laundry (napping VCs included)29:56 Netsuite - The business landscape is very chaotic right now. That's why you need NetSuite, by Oracle. Get the free business guide Demystifying AI at https://Netsuite.com/TWiST36:38 Claude Fable 5 first impressions: pricing, benchmarks & orchestration45:42 Where value accrues: application layer vs. models vs. private data1:00:06 Nationalization of AI labs: Bernie Sanders, Sam Altman & Trump agree?!1:01:25 Portfolio spotlights: Saronic, MotherDuck, and Nox MetalsSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanis
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68 MIN
The AI Tutor That Makes Kids Actually Think | E2298
JUN 8, 2026
The AI Tutor That Makes Kids Actually Think | E2298
The AI Tutor That Makes Kids Actually Think | E2298This Week In Startups is made possible by:Northwest Registered Agent https://northwestregisteredagent.com/twistLinkedIn Jobs https://LinkedIn.com/twistShopify https://shopify.com/twistPlaud https://Plaud.ai/twistToday’s show:*Schools teach kids to memorize formulas. AI helps them skip thinking entirely. Brilliant founder Sue Khim joins TWiST to tell us how her new AI tutor, Koji, uses the Socratic Method to help students solve complex problems on their own. Find out why she says “People aren’t anti-AI. They’re anti-being replaced and anti-slop.”PLUS Jason’s take on the VC horror stories going around X… and his own anecdote about the tenacity and passion of legendary investor John Doerr.Guest:Sue Khim on X: https://x.com/suekhimBrilliant: https://brilliant.org/Viral Koji launch video: https://x.com/suekhim/status/2060378988606878147Relevant Links:Viral Greg Isenberg post about VCs: https://x.com/gregisenberg/status/2061794787825479818Travis Kalanick’s story: https://x.com/travisk/status/2062224472426365045Matthew Prince’s stories: https://x.com/eastdakota/status/2062860530360959273John Doerr on X: https://x.com/johndoerrRoelof Botha on X: https://x.com/roelofbothaMichael Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/Mohr Davidow Ventures: https://mdv.com/Jason’s book “Angel: How to Invest in Technology Startups”: https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700Timestamps:0:00 Sue Khim's Alltuition origin story1:41 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!4:10 Brilliant: from launch to product market pull10:46 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://northwestregisteredagent.com/twist15:08 Pricing against tutors, not apps19:25 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist21:22 Koji demo24:11 Keeping Brilliant local while expanding30:22 Shopify - Turn those What Ifs into sales with the e-commerce platform powering millions of businesses. Sign up for your $1-per-month trial today at https://shopify.com/twist40:10 Every founder has a VC horror story44:33 John Doerr went the extra mile to hear JCal's pitch52:55 The LAUNCH investment strategySubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisCheck 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 McFarlandCheck out Jason’s suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com
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60 MIN