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This Week in Startups

Jason Calacanis
This Week in Startups
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  • AI Copyright & Training Data w/ Chris Paniewski | Wilson Sonsini Startup Legal Basics
    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
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  • Republic opens private markets as Positron takes on GPUs: A TWiST500 doubleheader! | E2176
    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 👇
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  • How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175
    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
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  • The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174
    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
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  • Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics
    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
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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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