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This Week in Startups

Jason Calacanis
This Week in Startups
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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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  • Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173
    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
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  • Jason’s Tesla Optimus prediction, Anthropic’s latest mega-raise and more | E2172
    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
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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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