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This Week in Startups

Jason Calacanis
This Week in Startups
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  • Is $MSTR over? Jason takes his victory lap. | E2216
    This Week In Startups is made possible by:Quo - http://quo.com/TWiSTSquarespace - https://www.Squarespace.com/TWISTMiro - http://miro.com/Today’s show: Michael Saylor’s Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new “dollar reserve” the answer?On TWiST, we’re looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly convoluted financial scheme.Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions…PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.Timestamps:(03:04) Why Jason broke his “No Demo Day” rule for the LAUNCH 35 Accelerator(07:08) What we can learn from BitcoinTreasuries.net about the marketplace(07:42) Why Jason remains SO skeptical on $MSTR… and any sufficiently convoluted financial scheme…(7:56) Jason’s Four Red Flags for rogue companies and financial schemes(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST(14:31) When loans go before equity, and how this can dilute your investment!(18:05) Is CNBC giving Michael Saylor a pass? Why Jason thinks he won’t go on “All-In.”(19:30) Checking in with Polymarket’s thoughts on potential MicroStrategy Bitcoin sales(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(22:58) Speaking of complex schemes… why S&P Global downgraded Tether(29:26) Is Tether too good to be true, as an investment?(25:17) Why Jason thinks the US waited too long to pass stablecoin regulations.(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!(36:15) Jason’s reaction to the NYT piece about Bestie David Sacks(43:14) Is there a growing divide within the GOP about how to engage with tech companies?(44:04) What are “Glue Employees” and why are they important?(45:03) How to tell your “Glue Employees” apart from the “union reps” and other rabble rousers…(51:50) Sunday Robotics: another human-ish robot but with WHEELS (and a baseball cap)(56:05) We’re checking out the Matic robot vacuum as well… Should these products be combined?*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/Check out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*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:(9:49) Quo (formerly OpenPhone) gives you a clean, modern way to handle every customer call, text, and thread all in one place. Try it free at http://quo.com/TWiST(20:21) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist(30:24) Miro - Help your teams get great done with Miro. Check out http://miro.com to find out how!Great TWIST interviews: Will Guidarahttps://youtu.be/pvJa2pzuXWQEoghan McCabehttps://youtu.be/9dHN4YFkgv4Steve Huffmanhttps://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424Brian Cheskyhttps://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112
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  • SO MANY THINGS need to go right just so you can watch a TikTok! | E2215
    Register here to join Founder University Japan’s kickoff! 👉🏻 https://luma.com/cm0x90mkToday’s show: On TWiST, Alex is chatting with Neubird CEO Gou Rao about the intricate complexity of IT Ops, and the vast amount of layers and components that have to be delivered very quickly to your phone in order to stream a simple video clip.Neubird has developed Hawkeye, an AI “engineer” that uses “context engineering” to isolate and troubleshoot problems, while still keeping costs down. Loading up a video to show your friends may SOUND straightforward, but it’s actually, as Alex notes, a miracle anything on the internet works at all.PLUS we’ve got Subject AI CEO Michael Vilardo stopping by to tell us how the app uses gamification to keep kids learning and engaged. NOTE TO FOUNDERS: Mike got invited on the show because he sends email updates to his “dream investors,” including Jason. It’s a solid best practice!Finally, we’re flashing back to a remarkably prescient 2019 interview with then-Scale AI chief Alexandr Wang, who tells us why he thinks the AI Doomsday scenarios — AND the elaborate AGI promises — are both way overblown.Timestamps:(3:19) Neubird asks: What if we took AI tools and applied them to IT ops?(5:17) Why does IT ops seem to get so much more complicated over time?(6:14) Gou walks us through all the various components that need to be delivered when you post a simple TikTok video(8:41) Why agentic systems (like Hawkeye) are the ideal tool for monitoring metrics, logs, traces and alerts(10:05) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(11:17) How is IT Ops different from Site Reliability Engineering (SRE)?(12:36) Is Hawkeye an AI Agent or an “Engineer”? How we decide what to call our “co-pilot.”(16:07) How “context engineering” helps Hawkeye isolate problems, and keeps inference costs down(17:27) Is Hawkeye plug and play? Or does it need to be trained on a specific system?(18:59) How Neubird measures Hawkeye’s overall effectiveness(19:59) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to http://getperspective.ai/twist(21:47) Hawkeye can diagnose and make recommendations, or go in and fix the problem itself, if you like!(24:27) What Gou thinks about the pace of AI innovation: Has it slowed? Are we in a lull?(25:41) LLMs already have a lot of knowledge, but how do we enhance their EQ?(28:58) TIP FOR FOUNDERS: Send updates to your “dream” investors! That’s how Mike got on the show!(30:20) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at https://Uber.com/twist⁠(31:21) The importance of branding… Why Mike pivoted to Subject.ai(33:43) How Subject helps bring teachers and students together for more 1-on-1 interaction(35:48) Mike walks us through how Subject works, and how gamification keeps kids engaged(39:56) Is anything lost when an AI grades a student’s test, rather than a human?(42:09) Subject can serve as a “teacher of record” in classrooms(46:28) Why Mike and Subject AI are back in the office(47:40) TWIST FLASHBACK with Alexandr Wang of Scale AI from November 2019(53:10) Alexandr explains AI to Jason (back when it was still called “Machine Learning”)(1:01:08) How AI will help people focus on “higher-value work”(1:04:48) Why Alexandr thinks apocalyptic AI scenarios are unrealistic(1:13:28) Are the big promises around AGI overblown?*Thank you to our partners:(10:05) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(19:59) Perspective AI: Real insights, straight from your customers, and your first two months are on us. Just go to http://getperspective.ai/twist(30:20) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at https://Uber.com/twist
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  • Even great startups sometimes need to pivot (feat. Francisco Cornejo of Theo) | E2214
    Register here for Founder University Japan’s Kickoff 👉🏻 https://luma.com/cm0x90mkToday’s show:The team from Familify had released a well-reviewed storytelling app for kids and parents… but it just wasn’t growing!Then they noticed that Bible stories and faith-based content was particularly popular. So they decided released a brand new app, Theo, just for these sorts of lessons and stories. And the new product overtook Storybook in just a few weeks!It’s a vital lesson for founders… Even if you succeed, you may be able to succeed EVEN MORE. Remain flexible and open to strong new ideas (especially if, like Francisco, your wife suggests them!)PLUS we’re chatting with Collin from En Vérité about how AI can make do diligence much less painful for investors AND checking out our latest Gamma Pitch Deck competitor. Find out why Jason says Jake Triton from Pitch Prfct might just be closing in on Product Market Fit.Timestamps:(5:20) How Storybook, then Theo was motivated by a children’s mental health crisis(5:46) Despite great reviews, Storybook wasn’t growing! Here’s what they did.(7:13) The Power of Experiments: Theo overtook Storybook in popularity in JUST WEEKS(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:04) Digging in to the decision to flip from all stories to Bible stories(12:34) The difference in how users perceive prayer vs. meditation(14:06) Will they make different Theos for different denominations of Christianity? Other faiths?(14:55) Jason makes the case for the Theo app and its team(19:59) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(21:50) Key lessons for founders from Francisco’s pitch today(26:51) Collin Sebastian from En Vérité joins the show to tell us how En Vérité helps prepare founders for the due diligence process(30:00) Enterpret: Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.(31:03) Jason recalls some diligence horror stories from his past(32:14) Where En Vérité gets their data and how they use it(36:39) What Collin learned from his time at SoftBank(39:44) The Gamma Pitch Deck Competition returns with Jake Triton from PitchPrfct [https://x.com/JakeTriton] @pitchprfctsms(42:29) Why Jason thinks Jake is closing in on Product Market Fit(45:51)How PitchPrfct plans to have AI help build your campaign and workflowSubscribe 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:(10:04) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:59) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(30:00) Enterpret: Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to Enterpret.com/twist to book a demo and see it in action.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/@thisweekinstartups
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  • Jason predicts a “major M&A moment” in the next six months! | E2213
    Register here to join Founder University Japan’s kickoff: https://luma.com/cm0x90mkToday’s show:Google and Meta had their cases dismissed (or received a slap on the wrist)… Despite all the backlash and cynicism, AI companies continue making bank and releasing hot new products… What does it all mean?For Jason Calacanis, the signs are pointing to a “major M&A moment,” with huge opportunities for increased efficiency and consolidation among America’s favorite brands and largest companies?Who will it be? Join Jason and Alex for a round of hot speculation.PLUS why Jason thinks Michael Burry is both right and wrong about GPU depreciation, why NOTHING is certain about these OpenAI mega-deals, Google’s Nano Banana Pro can make infographics and they’re VERY impressive… and much more.Timestamps:(1:54) Jason’s calling in from Vegas… He’s doing a hot lap at F1!(3:18) How restaurants are becoming the new Hot IP(6:50) Founder University is heading to TOKYO!(9:27) Why Jason thinks the future of startups is truly global(10:06) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist(11:39) Nvidia killed it on the numbers… but what are the vibes around AI? Jason sounds off.(13:05) Why nothing is certain when it comes to the Nvidia/OpenAI deal(19:40) Is Google now WINNING consumer adoption of AI? How did it get this close?(19:57) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(26:07) Meanwhile, AI apps are still dominating the iOS Store(27:09) Why Jason and Alex think Michael Burry’s both right and wrong about GPU depreciation(30:13) 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!(37:46) We’re testing out Nano Banana Pro on a BBQ infographic challenge(43:42) What a week for AI models! It doesn’t seem like things are slowing down…(46:12) Kalshi is growing fast, but can it catch Polymarket?(47:50) Is a rate cut coming? Jason and Alex read the tea leaves.(50:13) Why Jason predicts a “major M&A moment” in the next six months(52:09) VIEWER QUESTION: What should a software engineer be working on RIGHT NOW.(54:02) Founder Friday is now… STARTUP SUPPER CLUBSubscribe 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:(10:06) Pipedrive - Bring your entire sales process into one elegant space. Get started with a 30 day free trial at pipedrive.com/twist(19:57) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(30:13) 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.com
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  • Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212
    Today’s show:The race for more compute gets all the headlines, but Mistral AI CEO Arthur Mensch tells us the REAL danger is running out of data!On TWiST, Jason and Alex are chatting with the head of France’s largest foundation AI company, Mistral AI, about how enterprises can get more out of their AI pilots, whether the West is lacking leadership on open-source, why Mistral AI isn’t pursuing every possible kind of AI application, and optimizing your models for performance rather than benchmarks (aka benchmaxxing). Find out what it’s like to run a huge AI company in today’s intense environment!PLUS… why everyone made the wrong call on OpenAI vs. Google… Kraken’s fresh $20 billion valuation… Jason’s urgent message to every company thinking about M&A… and much more!Timestamps:(3:35) Why did everyone get it wrong on Google vs. OpenAI?(10:51) Why Jason thinks drone delivery will make everyone safer(9:52) SQUARESPACE: Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:26) Mistral AI CEO Arthur Mensch joins us! What’s it like to run a foundation model AI company in this intense environment?(14:50) Why enterprises aren’t getting enough value out of AI and how Mistral AI aims to correct this(18:45) Why Mistral AI’s goal is, ultimately, to disappear…(20:19) LinkedIn Ads: Start converting your B2B audience into high quality leads today. Launch your first campaign and get $250 FREE when you spend at least $250. Go to http://linkedin.com/thisweekinstartups to claim your credit.(22:49) Are Europe and the US lacking leadership on open source AI?(24:53) Mistral AI doesn’t need to compete in every category... how big of an advantage is focus?(27:05) The “two bottlenecks” in Machine Learning: Compute and Data(29:01) How Mistral AI works with human experts to annotate their models, and where they source them from(30:06) 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 https://nexos.ai/twist.(34:24) Is optimizing your model for benchmark tests (aka benchmaxxing) like cheating?(40:08) Will we ever be able to run smaller AI models on our phones?(44:21) When does Arthur think we’ll have truly helpful humanoid robots in our lives?(49:42) Suno lawsuits and why Jason says you should NEVER break the rules, ESPECIALLY with the music industry(54:28) Release the Kraken! They’re now worth $20 billion.(56:48) Jason is going to F1… should he take up the offer and do a dry run?(58:30) How Meta beat the FTC and why Jason is so excited about it(1:01:37) Who should buy Crunchbase?
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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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