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This Week in Startups

Jason Calacanis
This Week in Startups
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  • The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik’s founders | E2146
    Today’s show:Grammarly is acquiring the beloved email app Superhuman! In today’s extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why they’re merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly’s 40M+ daily users already rely on email—and why this deal is the key to building the ultimate communication assistant. Don’t miss this deep dive into one of the most exciting AI acquisitions yet!#AI #Startups #Productivity #Grammarly #Superhuman #VentureCapital #MergersAndAcquisitionsTimestamps:(0:00) Introduction to the future of robotics and AI regulation(1:11) Introduction of hosts and overview of today's topics(4:19) Cloudflare's new pay per crawl product(09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(10:41) Polymarket segment on Apple's acquisition prospects(14:29) Grammarly and Superhuman CEOs interviews(19:42) Retool - Visit https://www.retool.com/twist and try it out today.(24:09) AI in productivity tools and email agents discussion(29:23) 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(30:46) Grammarly's AI platform and the acquisition of Superhuman(41:16) Introduction of Manu Sharma from Labelbox(41:47) The role of data labeling in AI and Labelbox's data factory(53:44) Labelbox's market position and capital efficiency post-ChatGPT(1:03:00) Advances in humanoid robotics with Jeff Cardenas from Apptronik(1:07:09) Market readiness and capabilities of Apollo 2 robots(1:13:27) Humanoid robotics: Google DeepMind partnership and international competition(1:20:54) US federal support for R&D in robotics(1:22:10) The evolution of humanoid robotics and Apptronik's growth in AustinSubscribe 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:(09:37) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(19:42) Retool - Visit https://www.retool.com/twist and try it out today.(29:23) 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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  • Rebuilding Civilization from First Principles: Inside Balaji’s Network State Vision | E2145
    Today’s show: Jason sits down with Balaji Srinivasan in Singapore to explore how he's turning years of theory into reality with Network School—the first node of a broader vision for internet-native, decentralized societies. Balaji explains how these “sharp societies” combine education, co-living, and startup culture to create physical communities aligned by values, not geography. From digital nomads to aspiring founders, people are opting into these new systems as an alternative to broken traditional governance. They discuss everything from Starbase and sovereignty to the future of democracy, Bitcoin, and America’s place in a multipolar world.Timestamps:(0:00) Introduction of Balaji Srinivasan and the impact of Bitcoin(1:39) The concept of Network School and Network State, including startup societies(4:05) Benefits and historical context of network effects in communities(7:08) Economic and social benefits of Network School(9:35) Global appeal and diverse motivations of Network School participants(10:22) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(12:30) Media perspectives on new societies and the challenge of self-determination(19:35) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(24:00) Personal experiences with US state migration and critique of California politics(27:11) The right to exit, thousand city system, and the two-party system(29:44) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist(31:09) Choosing a country like choosing a college and impressions of new cities(34:03) America's global reputation, politics, and the decline of empires(39:25) Dollar devaluation, Bitcoin's future, and global currency dynamics(41:26) Global power struggles: China versus the Internet and US demographics(44:01) Trump's tariffs, MAGA, and international trade realities(48:12) China's manufacturing dominance and US diplomatic legacy(54:39) The Internet's counterbalance to China and Bitcoin's future risks(1:00:31) Role of cryptocurrencies, quantum computing, and Bitcoin security(1:02:12) Cryptocurrency challenges and the resilience of Bitcoin(1:03:27) Network school state community and opportunities for investors(1:04:01) Closing remarks and final pitch for Network SchoolSubscribe 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:(10:22) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:35) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(29:44) Vouched - Trust for agents that’s built for builders like you. Check it out at http://vouched.id/twist(0:00)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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  • Travis’ Uber Comeback, AGI’s Stakes, Meta’s $100M AI Hires & Prediction Market Gold Rush | E2144
    Today’s show:EVs are igniting a global tariff war, and Xiaomi’s shockingly cheap, high-quality electric cars threaten to obliterate Western automakers, sparking fears of a manufacturing wipeout. In today’s brand-new TWiST, Jason and Alex dive into the EV price war, Uber’s rumored plan to team up with Travis Kalanick on a self-driving takeover, and DoorDash’s mega-drones giving us a glimpse of the future of food delivery. Plus, Tesla’s cautious safety driver rollout shows we’re only in the early innings of the autonomous revolution, a consideration of Meta’s talent shopping spree, AND a new edition of Reddit Rapid Response. Don’t miss this deep dive into the future of cars, delivery, and AI.Timestamps:(02:24) Guess who’s BACK at Uber? On the Travis Kalahnik-Pony AI deal.(10:43) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.(17:24) All the huge opportunities for Kalshi, PolyMarket and prediction markets(19:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(25:37) TODAY’S POLYMARKET: How well will Apple’s “F1” do at the box office?(30:03) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.(31:58)What actually IS AGI? And why does it matter for the Microsoft-OpenAI negotiation?(45:57) Inside Meta’s massive Superintelligence shopping spree: maybe it’s not so crazy to pay AI experts $100M?(01:05:15) Reddit Rapid Response: Can you be a great founder if you hate doing cold sales?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:(10:43) Superpower - Visit superpower.com/twist to get $50 off your membership. This offer is only for the first 100 twist listeners who sign up.(19:44) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:03) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.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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  • Multi-Agent AI, Open Protocols & Startup Acceleration with Saurabh Tiwary | AI Basics
    In this episode, Jason dives deep into the future of multi-agent systems with Saurabh Tiwary, VP & GM of Cloud AI at Google. They explore how teams of AI agents—not just single models—can collaborate to solve complex problems, helping startups scale faster with fewer resources.Saurabh introduces Google Cloud’s open frameworks:Agent Development Kit (ADK) for building flexible, debuggable agentsAgent-to-Agent (A2A) Protocol, now part of the Linux FoundationThe emerging Multi-Agent Collaboration Protocol, enabling AI systems to work across platforms and organizationsThey also discuss:Why AI agents are evolving from task-doers to decision-makersHow multimodal inputs (text, image, video, voice) will supercharge agent capabilitiesWhy openness and interoperability will define the next era of AI infrastructure*Timestamps:(0:00) Jason introduces Saurabh Tiwary, VP & GM of Cloud AI at Google, and sets the stage for a deep dive on autonomous agents.(1:09) What is an AI Agent Today?(2:54) When Will Agents Actually Work?l(6:30) Inside Google’s ADK (Agent Development Kit)(8:35l) Agent-to-Agent Protocol & Open AI Standards(11:35 ) Why Human-in-the-Loop Still Matters(13:41) What’s Next: Multimodal Agents & Real Startup Use Cases*Google Cloud Report: “The Future of AI: Perspectives for Startups”Free download → https://goo.gle/futureofaiGoogle Cloud Homepagehttps://cloud.google.com/Google Cloud: Agent Development Kit (ADK)https://developers.googleblog.com/en/agent-development-kit-easy-to-build-multi-agent-applications/https://cloud.google.com/vertex-ai/generative-ai/docs/agent-development-kit/quickstartAgent-to-Agent (A2A) Protocol by Googlehttps://developers.googleblog.com/en/a2a-a-new-era-of-agent-interoperability/Linux Foundation: A2A Protocol Overviewhttps://www.linuxfoundation.org/press/linux-foundation-launches-the-agent2agent-protocol-project-to-enable-secure-intelligent-communication-between-ai-agentsGoogle Research: AI Agents & Multi-Agent Systemshttps://research.google/blog/accelerating-scientific-breakthroughs-with-an-ai-co-scientist/https://cloud.google.com/transform/ai-agents-evolving-with-google-agentspaceGoogle’s Agentspace https://cloud.google.com/products/agentspace?hl=enGoogle’s Vertex AI Agent Builderhttps://cloud.google.com/products/agent-builder?hl=enWatch more AI Basics episodeshttps://thisweekinstartups.com/basics*Follow Saurabh:X: https://x.com/saurktLinkedIn: https://www.linkedin.com/in/saurabh-tiwary/*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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  • VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
    Today’s show:In this powerhouse VC roundtable, @Jason sits down with Sequoia’s Doug Leone and Cyberstarts’ Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders, and how to truly find product-market fit. They break down why big-tech résumés can be misleading, how to structure early teams, and what separates “missionary” talent from mercenaries. Plus, the myth of early ARR, the art of founder-board trust, and how AI is (and isn’t) reshaping startup velocity. Must-watch for founders, VCs, and anyone building from 0 to 1.Timestamps:(03:25) The origins of Wiz and how VCs know when to invest(05:17) What qualities are investors looking for in founders and entrepreneurs?(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(18:40) How to know when you’ve reached true Product Market Fit: the experts sound off(19:20) Notion - Try it for free today at https://notion.com/twist(25:39) The secrets of recruiting top talent(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(39:38) Judging a startup’s revenue quality and “founder vs. salesman” deals(53:38) Is venture capital kind of a SCAM?(55:00) Seed Investing: “Pick them right and early”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:(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(19:20) Notion - Try it for free today at https://notion.com/twist(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/techGreat 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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