This Week in Startups

• Anti-Work Uprising, Copyright Wars & the StreamFog Solution | E2124

  Today’s show: Jason, Lon & Alex are back with a spicy Monday episode of This Week in Startups. Jason goes off on unions vs capitalism, we dig into why fewer seed startups are making it to Series A, and look at OpenAI’s quiet copyright land grab. Plus: YC says Google should be broken up (then kind of walks it back), Perplexity’s wild $14B valuation, and Saudi Arabia wants its own national AI. We wrap with an Office Hours chat with Kevin Bondzio from Streamfog on the future of AR ads in livestreaming.*Timestamps:(2:38) Why Jason’s obsessed with Reddit’s anti-work community(10:30) Coda - Get started for free at https://coda.io/twist(12:21) Seed Stage Graduation rates(20:43) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(26:11) What’s going on with Tech M&A?(30:04) 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(33:50) What’s going on with the Copyright Office?(37:24) Licensing and competitive advantage in the AI era(48:28) AI and the future of subscription-based content(56:42) StreamFog wants to change the way creators advertise(1:14:13) Perplexity’s mega-valuation gets even mega-er(1:19:13) How Saudi Arabia just became an AI startup(1:22:05) Y Combinator pokes it’s nose in the Google antitrust case*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/v19fcp*Links from episode:Check out Streamfog: https://streamfog.com/Check out Peter Walkers post on “Graduating from Seed to Series A” https://x.com/PeterJ_Walker/status/1921288778192200087Learn about the HUMAIN here: https://www.spa.gov.sa/en/N2316474*Follow Kev:X: https://x.com/kevbondzioLinkedIn: https://www.linkedin.com/in/kevin-bondzio/*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(10:30) Coda - Get started for free at https://coda.io/twist(20:43) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(30:04) 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*Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*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*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:30:58
• OpenAI Scoops Instacart’s CEO, AI in the Courtroom & Off-Road Startups | E2123

  Today’s show: Jason, Alex, and Lon break down OpenAI’s latest power move: hiring Instacart CEO Fidji Simo to lead its consumer apps. They also dive into the ethical storm brewing around an AI-generated victim statement used in court — is this the future of legal testimony? Plus, they explore how late-stage funding rounds like a “Series G” don’t automatically spell trouble anymore, and what The Checklist Manifesto can teach startup founders. Stick around for another Office Hours, where WhereToWheel gets a shot at the spotlight.*Timestamps:(0:00) We kick off the show!(2:28) Intro: It's all about having a system...(8:52) Wait, OpenAI STOLE Instacart's CEO?(10:00) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions(18:03) Why Adam Curry is the Podfather(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(22:53) Would you want to be represented in court by an AI Avatar?(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(35:38) What the heck is "Minor M&A"?(48:10) When are we all getting humanoid robots?(53:30) Where2Wheel wants to help you off-roadSubscribe 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/v19fcp*Links from episode:Check out Wheel2Wheel: https://dev.where2wheel.com/*Follow Where2Wheel:X: https://x.com/Where2WheelLinkedin: https://www.linkedin.com/company/where2wheel-llc/*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(10:00) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist*Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*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*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:13:29
• Zoox Crash Fallout, COATUE’s $1B Open Fund, and Office Hours with FusionAds | E2122

  Today’s show: Jason, Lon & Alex discuss the day’s hottest tech and startup news. Zoox’s robotaxi crash and voluntary recall, COATUE’s innovative open-ended venture fund that could democratize private tech investing, the NSO Group's massive $167M fine for spyware abuse, Uber’s record-setting earnings and in-person work push, and a candid AI wake-up call from Fiverr’s CEO urging employees to embrace automation or fall behind. From regulatory shakeups to funding innovation and the rise of AI productivity, this episode captures the chaos and opportunity of tech in 2025.Timestamps:(1:09) Show Intro(2:43) Will Coatue's new low buy-in fund replace or supplement traditional VC investments?(9:55) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at www.openphone.com/⁠twist(13:38) Zoox issues recall: why this might be the best case scenario for self-driving cars.(20:18) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(22:39) Meta wins settlement against NSO: do spyware companies even need to exist?(25:45) Uber bests expectations in Q1! Why their future is looking bright.(29:48) Notion - Try it for free today at https://notion.com/twist(33:10) How scared should we be of AI replacing us? Fiverr's CEO says VERY.(40:57) In Office Hours, Evan from FusionAds wants to know: how to make clients feel more confident in with AI-generated marketing?(50:03) The Founder Friday Tournament's Final Four is now... a FINAL FIVE?!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/v19fcpLinks from episode:Do Things That Don’t Scale: https://paulgraham.com/ds.htmlFusionAds: https://www.fusionos.ai/ai-generative-advertisingFollow Evan:X: https://x.com/EG_FusionLinkedIn: https://www.linkedin.com/in/evangraj/Follow 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:(9:55) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at www.openphone.co(20:18) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(29:48) Notion - Try it for free today at https://notion.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

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  1:06:36
• Cursor’s $9B Round, AI-Powered Toys & CloudNuro’s SaaS Fix | E2121

  Today’s show: Cursor’s explosive growth, hitting $200M in ARR and a massive $9B valuation. They also explore the buzz around Magical Toys’ new AI-powered dinosaur, where LLMs meet playtime. The conversation turns to “vibe coding” and how AI dev tools are changing the way product teams build. Plus, Jason shares stories from his Formula 1 poker table, Uber’s latest autonomous vehicle partnerships get analyzed, and we bring you highlights from our Founder Fridays pitch showdown, featuring Kippy from Sydney and MomSub from Chicago. Stick around to hear how Cloud Neuro is tackling SaaS sprawl.*Timestamps:(0:00) Jason kicks off the show!(3:52) Rise in popularity of F1 and Netflix's impact(10:23) Uber stock, partnerships, and self-driving technology(10:47) 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/twisttoday!(13:50) Aurora Innovation's SPAC and Cursor's valuation discussion(19:07) Revenue quality concerns for startups(20:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(21:37) User engagement versus churn in startups(23:06) AnySphere's ARR and impact of faster development on tech(30:29) Fidelity Private Shares℠ - Visit ⁠https://www.fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.(32:11) Anker's portable solar solutions and off-grid living innovations(37:41) Jason's investment insights on Warner Brothers and Disney(38:27) Skype's decline and the rise of Zoom and Microsoft Teams(42:04) Founder Friday bracket final matchup and pitches(51:08) Interview with Fateen Anam Raffid from Magical Toys(59:24) Dino AI toy demonstration and future plans(1:04:20) Interview on CloudNuro's SaaS spend management(1:10:01) SaaS compliance, vendor-customer relationships, and AI spend management(1:16:09) CloudNuro's data-driven foundation and AI governance(1:18:46) Company growth, competitive landscape, and Chicago's entrepreneurial ecosystem*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/v19fcp*Links from episode:Magical Toys: https://www.magicaltoys.comCloudNuro: https://www.cloudnuro.ai/*Follow Fateen:X: https://x.com/Fateen_Anam*Follow Shyam:LinkedIn: https://www.linkedin.com/in/shyam-kumar-7b18524/:*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(10:47) 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/twisttoday!(20:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:29) Fidelity Private Shares℠ - Visit ⁠https://www.fidelityprivateshares.com/ Mention our podcast and receive 20% off your first-year paid subscription.*Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*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*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

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  1:25:51
• Apple’s App Store Loss, AI Persuasion, and an Interview with Tyler Denk of Beehiiv | E2120

  Today’s show: Jason, Lon, and Alex break down a loaded week in tech: Apple’s 27% App Store “link-out” fee gets shut down by a judge—unlocking margin for startups and slashing CAC; AI bots on Reddit’s r/ChangeMyView are now 6x more effective than humans at changing minds, signaling a seismic shift in online discourse; and Beehiiv CEO Tyler Denk joins to discuss building in public, rapid product iteration, and the irony of being critiqued like a market leader for innovating too fast. The big takeaway? AI is evolving fast, gatekeepers are falling, and founders who build through chaos are best positioned to win.Timestamps:(0:00) Episode Teaser(1:20) Introduction and venture capital power law(4:14) Economic data and labor market trends(8:19) Mimicking trades and Dub's Series A funding(10:05) Kyte - TWIST Listeners: Go to https://kyte.com/ and download the Kyte app today. Use code JASON to save 10% on your first rental.(14:48) Apple App Store ruling and startup implications(19:44) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months.(21:44) App store fees and antitrust concerns(27:34) Fivetran's acquisition and Lena Khan's impact on VC(29:58) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(32:02) Venture capital scenarios and M&A future(37:23) Jason’s Starbucks tweet and union perspectives(45:02) Reddit's AI experiment and online discourse(48:16) Interview with Tyler Denk from Beehiiv(49:52) Beehiiv overview and customer base(51:02) Beehiiv's revenue strategy and Boost feature(57:06) Balancing revenue streams and feature quality(1:04:30) MRR growth and founder transparency(1:08:05) Brand marketing impact and staying focused(1:11:44) Hiring challenges and platform comparisons(1:14:01) Twist 500 initiative updateSubscribe 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/v19fcpLinks from episode:Beehiiv: https://www.beehiiv.com/Follow Tyler:X: https://x.com/denk_tweetsFollow 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:(10:05) Kyte - TWIST Listeners: Go to https://kyte.com/ and download the Kyte app today. Use code JASON to save 10% on your first rental.(19:44) Atlassian - Head to https://www.atlassian.com/startups/twist to see if you qualify for 50 free seats for 12 months.(29:58) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartupsGreat 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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  1:14:46

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