This Week in Startups

Today’s show:Jason sits down with Wilson Sonsini partner Chris Paniewski for part two of our Startup Legal Basics series on AI law — this time tackling the question every founder is asking: who owns the output of AI systems?Chris has advised on some of the biggest AI deals in history, and in this episode he helps break down how intellectual property law is colliding with generative AI.Jason and Chris cover:What kinds of IP rights might apply to AI-generated output (copyrights, patents, trade secrets)Why human authorship is central to copyright lawWhether prompts are protectable IPHow GenAI platforms’ terms of service affect ownershipReal-world examples from Star Wars to Wirecutter to WarholWhat startups should document when using AI in developmentHow investors diligence AI companies on IP strategyIf you’re a founder, investor, or operator trying to understand how to responsibly use AI without losing your IP, this conversation is essential.*Timestamps:(0:00) Jason introduces part two of Startup Legal Basics with Chris Paniewski(1:20) Star Wars example: using LLMs to generate existing IP(3:10) Human authorship requirement in copyright law(5:25) Prompts, super-prompts, and the role of creative control(7:45) Photography analogy & the “monkey selfie” case(10:00) Patents, inventorship, and AI-generated inventions(12:05) Startups balancing speed to market vs. protectable IP(14:15) How to layer human creativity on top of AI output(16:20) Fair use, derivative works, and investor diligence*Check Out Wilson Sonsini: https://www.wsgr.comCheck out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics*Follow Chris:LinkedIn: https://www.linkedin.com/in/christopher-paniewski-09331a59/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Follow 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

Today’s show:Hear why Eric Jackson thinks Opendoor is the new Carvana, and how he’s planning to bring Drake on board as an investor (plus Jason’s Bestie Chamath).On a brand-new TWiST, Jason and Alex are chatting with Jackson of EMJ Capital about his hunt for elusive 100 baggers (stocks that return 100-to-1).PLUS we’re chatting with Weave Robotics’ Kaan Doğrusöz about designing practical domestic robots RIGHT NOW, rather than prototypes for 2030. Hear about how they got Isaac to fold laundry like a pro.All that and… how Jason would turn around TechCrunch, why board members should always have skin in the game, that Waymo motorcycle accident, AND Uber and Tesla’s first team-up to haul freight!Timestamps:(0:00) Jason is worried about the next generation facing the end of apprenticeship; here’s his advice for young workers(10:24) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(11:30) Kaan Doğrusöz of Weave Robotics joins to talk about getting his laundry-folding robot, Isaac, into customer’s homes(18:01) Isaac doesn’t have hands; here’s how Weave makes it work with grippers(20:44) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.(21:48) Show Continues…(24:51) Checking out some of Weave’s competitors… how did they settle on Isaac’s design?(30:01) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(31:10) What’s going on with TikTok?(36:15) Jason’s pitch is “BOYA”: Bring Your Own Algorithm(38:54) Eric Jackson of EMJ Capital stops by to talk up $OPEN and why he wants Drake to invest(40:14) Eric’s early YouTube career as an activist Yahoo! Investor(44:42) Lessons Eric learned from Carvana and how that informed his $OPEN bet(01:00:30) Why bringing Keith Rabois back was Eric’s ultimate dream for Opendoor(01:03:02) Why board members should always have “skin in the game” and why $OPEN wants Chamath back(01:07:26) Tesla and Uber are finally working together… They said it was impossible!(01:09:31) A look at YouTube’s new AI podcasting featuresSubscribe 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/jasoncalacanisThank you to our partners:Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.Miro - Help your teams get great done with Miro. Check out miro.com to find out how!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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:On a special edition of TWiST, Alex presents a trio of TWiST 500 interviews.First up, Medium CEO Tony Stubblebine on the company’s new Really Simple Licensing (or RSL) initiative, and how it’s helping to compensate writers for their content.THEN, Human Native CEO Dr. James Smith joins for an even deeper dive on AI licensing, why a writer’s content isn’t just DATA to them, and why the company is pivoting away from its old marketplace model.FINALLY, Jason Marks of TELO Trucks stops by to show off his EV mini-truck, walk us through why people need a powerful but tiny truck, and explain why they’re building trucks right here in the US of A.Timestamps:(0:00) Intro: It’s a trio of TWiST 500 interviews today!(02:57) Alex chats with Medium CEO Tony Stubblebine(04:54) Why Medium’s more worried about HIDING from AI than anything else(10:24) Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.(11:27) Show Continues…(15:02) What is RSL and why aren’t AI companies offering publishers a good value?(19:58) Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.(20:59) Show Continues…(22:03) How Medium calculates its revenue split with writers(26:57) Alex welcomes Human Native CEO/founder Dr. James Smith.(27:34) Writers see their content as their life’s work, but tech co’s just see DATA(30:01) DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.com/twist(31:06) Show Continues…(33:01) Why H.N. is pivoting away from licensing and the marketplace model(47:23) TELO Trucks CEO Jason Marks joins the show(48:25) What is a “mini-truck” and why they’re TELO’s focus(52:28) Why TELO is building their EV trucks right here in the US(54:42) Why towing capacity still matters, even on a mini-truckSubscribe 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/jasoncalacanisThank you to our partners:Nexos.ai. Stop Shadow AI in its tracks with the unified platform for secure AI adoption and productivity. Try it with a free 14-day trial at nexos.ai/twist.Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.DevStats translates complex engineering metrics into a shared language everyone at your company can understand. Get 20% off by going to DevStats.com/twistGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:There are new LAUNCH Accelerator and Founder U cohorts this week, and Jason’s running down some of his favorite new startups.PLUS Alphabet is the latest member of the $3T club, why Eric Schmidt was SO RIGHT about remote work, Robinhood is opening up private companies to more investors, Polymarket adds earnings reports, how Jason wagered on The Emmys this year, and MORE!Timestamps:(0:00) It’s kickoff day for LAUNCH Accelerator 35 AND Founder University!(02:32) Let’s talk about some new companies. Jason runs down the LA35 line-up and why he’s excited about these awesome startups.(10:33) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist(11:57) Show Continues…(19:50) Squarespace - Turn your idea into a beautiful website! Go to http://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.(21:05) Show Continues…(27:43) Lemon.io - Hire pre-vetted remote developers and get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(28:58) Looking back at Jason’s solar energy rematch vs. Energy Sec. Chris Wright.(31:23) Why Jason thinks solar power (+nuclear) is the future.(41:03) Why Alphabet is the latest member of the $3 trillion market cap club.(46:40) Jason says Eric Schmidt was right about work from home culture(48:51) How Robinhood is giving everyday investors access to private companies(51:44) Polymarket introduces prediction markets for corporate earnings.(53:58) Why Jason loves prediction markets… and how he gambled on the Emmys this year.Subscribe 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/jasoncalacanisThank you to our partners:OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twistSquarespace - Turn your idea into a beautiful website! Go to http://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.Lemon.io - Hire pre-vetted remote developers and get 15% off your first 4 weeks of developer time at https://Lemon.io/twistGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:On Friday’s TWiST, Jason, Alex, and Lon look back at some highlights from this week’s big All-In Summit in Los Angeles, including a fiery, no holds barred presentation from Palantir CEO Alex Karp, Elon Musk delving into the key challenges facing Optimus, and Tucker Carlson debating Mark Cuban on Ukraine. PLUS… why schools may start blocking social media apps, the FTC’s new investigation into social chatbots, AND omnidirectional Zoox robotaxis are headed to Las Vegas.Timestamps:Welcome back to TWiST!(1:52) Jason’s thoughts on the killing of Charlie Kirk(10:34) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(10:52) Show Continues …(12:15) Reacting to All-In Summit highlights (Elon Musk, Alex Karp, Tucker Carlson, Mark Cuban)(21:23) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits(22:18) Show Continues …(26:09) Palantir, Alex Karp, and debate dynamics(31:03) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist(32:13) Show Continues …(45:03) How the internet used AI tools to make sense of Charlie Kirk’s death(56:22) Why Jason thinks it’s smart to block social media during school hours(1:03:43) The FTC chatbot investigation leaves out Anthropic’s Claude… here’s why(1:13:27) Zoox robotaxis make their Vegas debut… Here’s how they’re different from Waymo(1:19:38) Are Tesla robotaxis headed for CA soon? Polymarket says… maybe(1:27:21) Closing remarks and banterSubscribe 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/jasoncalacanisThank you to our partners:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTAWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/creditsPublic - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twistGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Jason sits down with Wilson Sonsini partner Chris Paniewski for a special Startup Legal Basics on one of the thorniest questions in tech right now: how copyright law applies to AI training data.Chris has worked on some of the biggest AI deals ever — including Scale AI’s $14B+ partnership with Meta and OpenAI’s $6.5B acquisition of Jony Ive’s design studio — and brings practical, on-the-ground insights from advising leading AI companies.In this episode, Jason and Chris cover:Why AI copyright law is unsettled and will take years to shake outThe difference between training data and output in legal termsHow “fair use” really works (and why it’s a defense, not a permission slip)The risks of scraping vs. licensing, and why open source ≠ free useHow investors are diligencing AI startups around training dataWhy startups must think differently once they’re funded vs. hacking in a dorm roomWhether you’re building an AI product, investing in one, or just trying to understand where the law is headed, this conversation breaks down the real legal risks every founder should know.Timestamps:(0:00) Jason introduces the Startup Legal Basics series & Chris Paniewski(1:25) Why AI copyright law is unsettled(3:40) Training data: scraping vs. licensing(6:05) Open web ≠ open license; pitfalls around terms of service(8:15) Investor diligence & risks around training data(11:00) Open source & Creative Commons: common founder mistakes(13:25) “Fair use” explained: the four-part test(15:45) Why most disputes never make it to case lawCheck Out Wilson Sonsini: https://www.wsgr.comCheck out all of the Startup Basics episodes here: https://thisweekinstartups.com/basicsFollow Chris:LinkedIn: https://www.linkedin.com/in/christopher-paniewski-09331a59/Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisFollow 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

Today’s show:In this founder-focused episode of This Week in Startups, we sit down with Republic’s Kendrick Nguyen to learn more about the company’s efforts to make the private markets accessible to the common investor. Best known for its work in equity crowdfunding, the Valor-backed startup now offers access to secondary shares, tokenized assets, and much more. Following, TWiST spoke with Positron CEO Mitesh Agrawal to learn more about his company’s inference-focused AI compute hardware. Related to fellow TWiST500 company Etched, Positron is building custom chips to take on the computing work required to deliver your AI query results faster and with less power draw than what GPUs can offer. With AI inference compute demand rising, the fellow Valor-backed startup has even more powerful systems coming to market in 2026 that have our hopes up that the AI cost curve can continue to point downward.Timestamps:(0:00) A future with more efficient and accessible intelligence(0:41) the following sponsors are mentioned: AlphaSense, Vanta, and Oracle Cloud Infrastructure(1:26) Introduction to the episode and the two featured companies, Republic and Positron(2:43) The history and purpose of Republic, a financial crowdfunding platform(5:39) Discussion of the current state and growth of equity crowdfunding(9:19) Kendrick Nguyen explains Republic's role as a financial infrastructure company, not a competitor to venture capital firms(11:17) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠ (12:25) Republic's different products, Republic Capital and Republic Venture, are explained(14:00) The challenges and progress of secondary trading for non-accredited investors(20:14) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(21:21)The concept of a unified "e-finance" infrastructure is introduced(25:45) Positron CEO Mitesh Agarwal discusses the future of AI chips and the limitations of current GPUs for inference workloads(31:12) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist(32:22) Discussion on the inefficiency of GPUs for inference and how Positron's Atlas system addresses it(38:30) Positron's strategy of using their Atlas system to prove their technology and generate revenue(42:51) The market shift from AI training to inference and the future of Positron's chips(51:14) The confidence in Positron's capital efficiency and their ability to compete with NVIDIA(52:47) Positron's focus on linear algebra acceleration rather than just transformersSubscribe 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/jasoncalacanisThank you to our partners:(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.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🎥 Watch the full episode here 👇

Today’s show:In this TWiST founder triple-shot, Alex digs into the real-world rollout of AI agents: Paid.ai’s Manny Medina explains agent economics and value-based pricing, iTruckr’s Camilo Ramirez shows agents booking loads and coordinating drivers, and Tenax’s Elise Myrans demos computer vision + drones that score a single home’s wildfire/flood risk for smarter underwriting—plus live office-hours on winning enterprise pilots without getting stuck in PoC purgatory.Timestamps:(00:00) Brainstorming hacks for sales cycles in regulated industries — castles, moats & alligators!(03:50) Meet Paid.ai: tracking costs & monetization for AI agents(04:35) Paid.ai’s Manny Medina on the “year of agents” & early enterprise traction(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(11:06) The tough economics of AI agents vs SaaS — margins squeezed by tokens(18:20) How Paid.ai gets granular: tracking signals & agent activity with OpenTelemetry(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(29:16) Enter iTruckr: Camilo Ramirez brings AI dispatch to the freight industry(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(39:02) Scaling from small fleets to mid-sized trucking companies — lessons from AI Trucker(55:59) Tenax ai helps homeowners & insurers manage wildfire, flood & climate riskSubscribe 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/jasoncalacanisThank you to our partners:(09:04) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(21:20) Coda - Empower your startup with Coda’s Team plan for free—get 6 months at https://www.Coda.io/twist(31:43) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:Jason heard Lina Khan on The Bulwark and got a little fired up.Plus Google doesn’t have to invest in Chrome… or basically do much of anything… Atlassian picked up not just any browser company but THE Browser Company… Follow-up thoughts on that MIT “companies aren’t using AI” study… AND Jason’s “two stock markets” theory. It’s a can’t-miss Friday TWiST.Timestamps:(00:00) Sony responds to Kpop Demon Hunters success… but Jason’s not buying it!(10:44) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(11:10) Jason heard Lina Khan on The Bulwark and he has THOUGHTS(12:40) Google doesn’t have to divest Chrome! So what ARE the remedies?(18:31) Atlassian’s buying a browser company? Which one? THE Browser Company.(20:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(21:22) When early DPI is better than NO DPI.(26:58) AI that helps you GET a job?! What a twist!(29:46) Jason and Alex have questions about that MIT AI study…(30:57) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.(32:07) More Browser News! Why Jason’s bullish on Brave.(35:10) Perplexed by “Perplexity”: Jason’s rules for domain names(39:54) The path is cleared for Polymarket’s return to the US(47:06) Jason’s “Two Stock Markets” theory(53:02) Mistral looking to raise 2 billion… euro!(56:08) Jason’s political philosophy: More joy and happiness(59:18) Stripe’s new stablecoin blockchain has no native token! So what’s it for?(01:04:12) Jason’s tips for lowering your churn rate(01:11:56) How to use Reddit to uncover pain pointsSubscribe 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/jasoncalacanisThank you to our partners:(10:44) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(20:57) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(30:57) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the “have” companies — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms.From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for.Whether you’re a founder navigating investor FOMO or a VC competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.*Timestamps:(0:00) Jason welcomes Becki back to Startup Legal Basics(0:32) The “haves” vs. “have-nots” in today’s startup market(1:28) Creative legal structures: the “off-menu” items(4:19) Travis’ Uber favor & modern founder asks(7:05) Rise of secondaries & unusual board structures(11:22) Mandatory follow-on investment clauses in seed rounds?(14:13) Crypto’s resurgence and legal implications(15:55) The decline of proper diligence in hot deals*Check Out Wilson Sonsini: https://www.wsgr.comCheck out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics*Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Follow 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

Today’s show:Jason and Alex are joined by Nuro’s Dave Ferguson to unpack the Lucid–Uber–Nuro deal aiming to launch fully driverless Gravity SUVs on Uber by 2026. They dig into why off-the-shelf sensors and Nvidia’s Thor chip drive costs down, how mapping 150 cities improves safety, and why lidar still matters for night and edge cases. Plus: lessons from Cruise’s collapse, how regulators think about safety multiples, and why autonomy could finally make rides cheaper than owning a car.Timestamps:(00:00) Show intro…(06:23) Uber x Lucid x Nuro: why this 2026 robotaxi deal matters(09:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(11:13) What the self-driving “cost stack” really looks like in 2025(14:08) Road-mapping at scale: Nuro’s 150-city data collection push(15:38) Can AVs handle snow & rain? Weather rollout and Uber Black positioning(20:05) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(21:07) Show Continues…(24:24) Probabilistic vs. deterministic driving models — and the DARPA roots(30:08) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.(31:08) Show Continues…(35:38) Post-Cruise reality check: transparency, regulators & trustSubscribe 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/jasoncalacanisThank you to our partners:(09:57) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:05) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(30:08) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:Find out why it’s important to “get curious,” and more deep founder insights on a new TWiST.Jason and Alex are back with a look at Robot vs. Human violence spilling out into the streets, Elon Musk’s vision for humanoid robots, and a reconsideration of Apple’s open-source AI models. Is the hardware giant not getting enough credit for its smaller-scale innovations?Plus Grok has another hit model, AND a chat with Scale Social founder Runbin Dong about the importance of knowing your worth.Timestamps:(0:00) Robot vs. Human violence in the streets! Is anti-clanker behavior inevitable?(05:13) Producer Claude’s company Anthropic is growing FAST, raising BIG money(09:21) More on why Jason is convinced Tesla’s Optimus robots are the future(10:35) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST(11:50) Show Continues…(20:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(21:19) Show Continues…(23:31) Ask Jason: Should you get a ticket for messing with an autonomous vehicle?(27:04) Is Apple not getting enough credit for its open-source AI models?(30:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(31:55) Show Continues…(38:08) Grok has another hit AI model… how can anyone even keep track of this?!(40:27) Runbin Dong of Scale Social stops by from ICELAND(42:54) How Runbin’s job delivering homemade dumplings inspired his startup(47:05) Why founders need to know their WORTH when pricing their products(59:21) Jason’s advice for companies that are creating their own categorySubscribe 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/jasoncalacanisThank you to our partners:(10:35) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST(20:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(30:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/creditsGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:*“KPop Demon Hunters” is one of the year’s biggest smashes… AFTER Sony sold it off to Netflix for cheap! Hear about what went wrong with one of the year’s worst deals…PLUS Grok is counting on SPEED to help it outpace rivals… How Rep. Ritchie Torres (D-NY) ran into trouble on the podcast circuit… Nvidia’s big earnings report, and why everyone is watching that company in particular SO closely… PLUS a new Polymarket predicting the future of OpenAI!Timestamps:(0:00) How Sony missed out on “Kpop Demon Hunters”(10:15) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(11:20) Show continues…(13:59) Why some politicians struggle so much on podcasts(19:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(20:53) Show continues…(30:24) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist(31:37) Grok is relying on SPEED to outpace rivals… and it’s working(41:23) Are AI companies playing a mega-budget game of chicken?(42:31) Why everyone’s watching Nvidia’s earnings so closely(47:50) Jason says he’ll NEVER go back to a non-AI browser(53:32) Polymarket: Is OpenAI going to release their own browser?Subscribe 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/jasoncalacanisThank you to our partners:(10:15) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(19:30) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit aws.amazon.com/startups/credits(30:24) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twistReady to level up your AI collaborations?Head to www.claude.ai/twistYou can’t do everything we’re doing without a paid plan…But TWiST listeners get 50% off their first three months of Claude Pro.Just go to Claude dot AI Slash TWiST to get started.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what’s happening in today’s startup market. From excess dry powder on the VC side to companies struggling to “grow into” their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today’s more structured environment.Why down rounds and structured deals are becoming more commonHow “pay-to-play” works (and why it’s showing up so often now)The psychology of VCs vs. founders during tough fundraisesWhat the M&A landscape really looks like in 2025Legal provisions investors are using to protect themselves in today’s talent warsWhether you’re a founder preparing for your next round or an investor navigating tougher terms, this conversation will help you understand the new realities of startup fundraising.*Timestamps:(0:00) Becki DeGraw joins Jason for Startup Legal Basics(1:12) The “perfect storm” shaping today’s startup market(4:30) Companies struggling to grow into 2021 valuations(6:31) Why down rounds and structured deals are rising(8:59) Pay-to-play explained: what happens if investors don’t participate(15:43) The mid-market M&A wave vs. big tech acquisitions(20:37) Talent wars, acqui-hires, and protective legal provisions*Check Out Wilson Sonsini: https://www.wsgr.comCheck out all of the Startup Basics episodes here: https://thisweekinstartups.com/basics*Follow Becki:LinkedIn: https://www.linkedin.com/in/rebecca-degraw-639bbb62/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Follow 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

Today’s show:On a brand-new TWiST, Jason and Alex are asking why there are SO MANY note-taking AI apps?Plus another death has been linked to ChatGPT… is it too easy to get past chatbot guardrails? Why Donald Trump Jr. is joining Polymarket…. How the US Navy could catch up with its international rivals… AND should Apple just buy a big AI company to help them catch up?All that PLUS a visit from Colin Russ, whose viral H1B Visa thread might just inspire Jason to reach out to his good friend, Vice President JD Vance. Check out the full episode!Timestamps:(0:00) Intro, Jason’s checking out Notion’s new AI note taking app… is it time to cancel Granola?(06:57) How Google Gemini’s new 2.5 Flash Image tool (formerly known as “nano-banana”) could change advertising(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(11:40) Show Continues…(17:50) Another death linked to ChatGPT… is it too easy to get around AI chatbot guardrails?(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist(20:34) Show Continues…(28:10) Donald Trump Jr. invests in Polymarket and joins the board…(29:45) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(30:49) Show Continues…(33:30) How Jason thinks the US Navy could catch up with China and other rivals, with help from startups(40:01) Do Jason and Alex think Apple might REALLY buy a big, expensive AI company? Would that be admitting defeat?(45:57) Colin Russ (@ThaaatColin) tells us about his viral X thread and why he’s worried about H1B visa fraud(55:32) Jason’s solution for the H1B system, and a message for VP Vance.(01:08:25) Jason responds to Kara Swisher, who accused him sucking up to power(01:19:07) Jason responds to his old pal Sam Harris, who thinks he’s loyal to the wrong peopleSubscribe 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/jasoncalacanisThank you to our partners:(10:28) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(19:26) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist(29:45) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:On an upbeat and optimistic new TWiST, Jason and Alex are debating why any new innovation or technology gets hit with a wave of bitter cynicism.PLUS Jason defends the government taking shares of Intel, explains the importance of interoperability, and predicts how AirBnB’s Joe Gebbia will upgrade the US government’s website design.All that PLUS thoughts on the Netskope IPO, Perplexity offering publishers actual revenue share, a deep dive on the new AI-based PAC, thoughts on open-source LLMs, and much much much more.Timestamps:(0:00) Cynicism vs. Optimism and why Jason thinks cynics go after any interesting new technology(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(11:04) Show Continues…(14:37) Why Jason supports the Intel deal but worries it will become a trend(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.(22:00) Show Continues…(27:02) Is it hypocritical to oppose socialist grocery stores but support the Intel deal? Jason says NO.(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(30:58) What does xAI hope to get out of this OpenAI/Apple lawsuit? Jason and Alex theorize…(39:12) Why Jason thinks interoperability is so important and how App Stores OUGHT to work(41:12) How AirBnB’s Joe Gebbia could potentially upgrade the US government’s websites(49:27) What does Netskope do exactly? SASE?! Producer Claude explains…(58:32) Alex and Jason celebrate Perplexity rev sharing with publishers(01:10:02) Jason’s thoughts on the Leading the Future PAC, and US AI policySubscribe 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/jasoncalacanisThank you to our partners:(10:02) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(20:46) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.(29:41) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:Terra’s collapse, Powell’s pivot, and OpenAI’s explosive growth all collide in this TWiST deep dive.Do Kwon has pled guilty after Terra/Luna’s $60B implosion, Fed Chair Powell hints at a September rate cut, and OpenAI has officially crossed $1B in monthly revenue (on a $12B run rate). Jason and Alex unpack what this means for founders, LPs, and the next wave of AI + crypto.They also cover Canva’s $42B comeback, Anthropic’s doubled $10B fundraise, and the brewing battle between Figma & Canva.Plus: Uber, Nuro & Lucid’s $6B robotaxi push — and why drivers are already protesting in Wuhan & Boston.#Startups #Crypto #AI #VentureCapital #OpenAI #Anthropic #Canva #Figma #ThisWeekInStartupsTimestamps:(0:00) INTRO(01:15) Fed rate cut signals & market reaction(05:36) Jason’s $400K in new fund bets(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(11:30) Show Continues…(16:22) Do Kwon & the Terra/Luna collapse(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.(21:23) Show Continues…(29:43) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twist(30:55) Show Continues…(36:14) OpenAI’s $1B/month revenue run rate(42:13) Anthropic’s $10B round & AI market sizing(51:31) Canva’s $42B valuation & Figma comparisonSubscribe 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/jasoncalacanisThank you to our partners:(10:25) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(20:22) Bolt - Don’t be left behind. Build apps quickly without knowing how to code with Bolt.new. Try it free at https://www.bolt.new/twist.(29:43) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at https://www.alpha-sense.com/twistGreat 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Today’s show:In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi!First, Chalk’s CEO Marc Freed-Finnegan is tackling one of AI’s biggest bottlenecks—data freshness. Instead of relying on stale batch jobs, Chalk delivers real-time pipelines for inference compute, automatically transpiling Python into C++/Rust so it can run blazing fast in production. Investors are calling it the ‘next Databricks’—and after hearing this convo, you’ll see why.Then, Tollbit’s CEO Toshit Panigrahi returns after raising a $24M Series A and signing up 1,400+ publishers. With RAG traffic exploding and robots.txt losing its teeth, their ‘bot paywall’ could reshape how AI agents pay for the content they consume. Are we heading for a Spotify moment for data licensing?A must-watch if you care about the economics of AI, from data pipelines to publisher monetization.Timestamps:(0:00) Intro + sponsors(1:03) Alex tees up two Twist 500 interviews: Chalk & Tolbert(2:47) Why AI is shifting from training compute to inference compute(4:41) Data freshness & real-time inference explained(10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(12:00) How Chalk transpiles Python into C++/Rust for speed(18:52) Chalk’s business model, margins & $500M valuation(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(21:24) Show Continues…(28:02) Tollbit returns: $24M Series A & the rise of RAG bot traffic(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(31:41) Show Continues…(36:53) Robots.txt losing relevance & the case for bot paywalls(39:19)Publishers, AI agents & the future economics of the webSubscribe 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/jasoncalacanisThank you to our partners:(10:43) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(20:11) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:37) .TECH: Say it without saying it. Head to get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

In this AI Basics episode, Jason sits down with Matt Rouif, Co-founder & CEO of Photoroom — the AI photo editing app with 300M+ downloads and 5B images processed annually.They break down:Why Photoroom built its own specialized AI modelsHow they grew from a scrappy startup to $50M+ in revenueLessons in product-led growth (from eBay sellers to DoorDash & Amazon)Red-teaming, brand safety, and building trust in AI imageryThe future of personalized ads, content, and designThis one is a masterclass for founders, operators, and builders.Timestamps:(0:00) Matt Rouif joins Jason to discuss AI Basics.(0:45) Meet Matt Rouif: Photoroom’s $50M+ AI photo startup(3:15) Live demo: background removal + virtual try-on(7:40) From indie sellers to DoorDash & Amazon(12:20) The “Barbie Movie” API moment(17:05) Red-teaming AI: trust, safety & brand protection(22:10) Running a 100-person AI startup(26:30) The future of personalized ads (put you in the ad?)Explore Further:Google Cloud’s Report: The Future of AIGet insights from 23 leading experts on how startups can leverage AI for real business impact.👉 Read the full reportMore AI Basics EpisodesFounders, operators, and builders — catch up on our full Startup Basics series (Legal, Finance, Growth & AI):👉 thisweekinstartups.com/basicsLinks from episode:Check out Photoroom: https://www.photoroom.com/Check out Google Cloud: https://cloud.google.com/Follow Matt:X: https://x.com/matthieurouifLinkedIn: https://www.linkedin.com/in/matthieurouif/Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisFollow 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

Today’s show:We’re back with two insightful new TWiST founder interviews.First up: Dean Leitersdorf of Decart tells us about squeezing maximum productivity out of your GPUs. But it’s not all talk: he also shows us the incredible open world model that can magically transform live footage.THEN! Jason and Alex chat with Syncere AI founder Aaron Tan about Lume, his robotic lamp device that went viral for folding laundry. Hear why Aaron thinks the future of robotics is not necessarily humanoid, and all about his future plans for the Lume arms.Timestamps:(0:00) Alex introduces our TwiST 500 interviews(02:27) TWiST 500 Interview #1: Dean Leitersdorf, CEO and Founder of Decart(04:37) Setting out to build a “kilo-corn,” a trillion dollar company(06:27) How making AI much faster opens up a world of new opportunities(09:48) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(11:00) Why Dean thinks chatbots are the interface of the future(17:24) How Decart builds and trains its models more efficiently (and for less money)(20:01) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(21:14) Show Continues…(24:36) Interview #2: Aaron Tan of Syncere AI(25:13) Behind-the-scenes of that viral Lume “robot lamp folding laundry” video(30:23) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.(31:25) Moving beyond laundry: what else these Lume robots do?Subscribe 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/jasoncalacanisThank you to our partners:(09:48) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(20:01) Netsuite - Download the ebook CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(30:23) Stripe Startups - Stripe Startups offers early-stage, venture-backed startups access to Stripe fee credits and more. Apply today on stripe.com/startups.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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916