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This Week in Startups

Jason Calacanis
This Week in Startups
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  • Jason Unpacks Sequoia’s New Funds"| E2199
    Today’s show:Australia has accused Microsoft of employing a dark pattern… Hear why Jason says these kinds of sneaky tactics aren’t usually worth it.It’s a brand-new Monday TWiST and it’s PACKED with news. In addition to Australia’s allegations against MSFT, we’re looking at Chinese drone fails and wondering how live experiences will change in the age of AI.PLUS has Tesla finally “solved” FSD after years of promises? Does it matter that so much of Mercor’s revenue goes back out to contractors? Do Chinese LLMs have a major advantage when it comes to the stock market over Western counterparts? Why Jason avoids overseas deals when he doesn’t speak the language or know the culture. And much more!Timestamps:(00:03:44) Fall is here! And Jason is already looking ahead to “BFCM” and the holiday season.(00:07:13) We’re bringing back the TWiSTies and a Prediction 2026 show(00:07:33) People are using AI to create fake receipts for fraudulent invoices!(10:00) Pipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.com/twist.(00:14:23) It’s earnings week for Meta AND Alphabet AND Microsoft AND AMAZON!(00:19:55) What happened with the disastrous Chinese drone and fireworks show?(20:00) Monarch - Thanks to our partner, Monarch! Try the app and get 50% off your first year by visiting monarchmoney.com/twist.(00:27:37) Why Jason thinks live experiences are going to get much bigger and more impressive in the age of AI(00:29:34) Why Tesla is training FSD on synthetic data now… Has FSD finally been “solved”?(30:00) AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/credits(00:45:10) What’s going on with these new Sequoia funds? Jason unpacks the strategy…(00:50:50) Jason doesn’t like to invest overseas unless he speaks the language and knows the culture(00:51:11) Jason’s thoughts on the controversy surrounding Sequoia partner Shaun Maguire’s comments(00:58:34) Mercor pays out 60-70% of its toppling revenue to contractors… does this MATTER?(01:06:14) Do Chinese LLMs have a major advantage when it comes to investing? (Humans are now betting on all this on PolyMarket)(01:09:45) Australia alleges that Microsoft is employing a dark pattern… why Jason says that’s a problem.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:AWS Activate - AWS Activate helps startups bring their ideas to life. Apply to AWS Activate today to learn more. Visit https://www.aws.amazon.com/startups/creditsMonarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWISTPipedrive - Bring clarity and control to your sales process with Pipedrive, the #1 CRM for small and medium sized businesses. Supercharge your sales today. Start with a 30-day free trial at pipedrive.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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  • If you’re not working 9-9-6, are you working hard enough? | E2198
    Today’s show:*Working from 9 am to 9 pm, 6 days a week, might seem like TOO INTENSE a commitment for some, but Jason argues that elite performance — and the mega-compensation that goes along with it — sometimes requires personal sacrifice. While 72-hour weeks might lead to burnout for some, it really comes down to individual choice.PLUS Jason and Alex deep dive the NBA gambling scandal and the sketchy reality behind high-stakes home games of poker. PLUS Presh Kumar takes us behind the scenes, to see how AI apps helped him develop and workshop the video for his new wellness startup, Tempo, and what’s with Anthropic buying chips from their AI rivals, Google? It’s a can’t miss This Week in Startups.Timestamps:(00:06:49) Jason and Alex are poker fans… what do they think about this insane NBA gambling scandal?(10:00) 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.(20:00) 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.(00:25:09) Is working “9-9-6” a reasonable goal? A guarantee of success? Why Jason compares it to being an Olympian.(30:00) Every.io - Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.(00:38:00) Our old buddy Presh walks us through the process of making his Tempo launch video(00:42:28) Jason and Alex check out some of Ridley Scott’s famous storyboards(00:48:03) Anthropic is buying TPUs from Google… Are these companies in LIKE with each other?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: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.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.**Every.io -** Running a startup is hard enough. Every takes care of incorporation, banking, payroll, benefits, accounting, taxes and more so that you focus on building, not back-office admin. Visit every.io.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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  • Amazon’s “Age of Efficiency,” LLM distribution, AI wearable worries, and more with Elad Gil | E2197
    Today’s show:*Amazon’s dropping a LOT of employees for AI and robots… are Jason’s darkest predictions coming true?Legendary investor Elad Gil joins Jason and Alex for the full show today! Together, they’re digging into the Amazon news, looking back at Jason’s predictions from just last month, and theorizing about just how many people will lose their jobs to computers, and what we’re going to do about it. (Is it possible the US hasn’t been massively hit by job displacement so far because those gigs already moved overseas?)PLUS… Anthropic’s Dario Amodei responds to criticisms from JCal’s bestie David Sacks, Sesame emerges from stealth to work on AI wearables, and where will people in the future interact with their favorite apps? A headset? Phones? Somewhere else? The great debate continues.Timestamps:(00:04:04) Our guest is iconic angel investor Elad Gil! What’s he working on…(00:04:54) Alexandria AI translates public domain books into all commonly spoken languages… Do people actually prefer AI translations?(00:09:16) Why compute tends to centralize over time… (It’s because of economies of scale!)(00:09:29) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(00:12:49) So are we building TOO MANY datacenters? Will AI apps eventually run on your phone anyway?(00:16:39) Jason says “The Age of Efficiency is upon us.”(00:19:24) When companies trade inference for market share(00:19:27) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(00:21:57) Why one of the main challenges of adopting AI is buy-in and convincing teams to use it.(00:25:47) Elad’s robotics questions: (1) What % of winners will be incumbents?(00:27:50) Jason called the Amazon news last month and we have the receipts!(00:29:36) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first yea(00:45:33) Jason says Adobe and Figma should abandon the UK entirely.(00:45:55) Time for a Polymarket: The sharps say 80% chance Tesla beats their quarterly earnings(00:51:02) What is Sesame? They just emerged from stealth, they raised $250M, and they’re working on AI wearables.(00:53:21) Jason has concerns about AI wearables that are always recording… Does Elad share these concerns?(01:03:17) The crypto industry is now one of the largest purchasers of US government debt… what does that mean? Who owns who?(01:08:53) Anthropic responded to JCal’s Bestie David Sacks… Is Dario Amodei a doomer? Fearmongering?(01:19:12) Why Jason thinks AI companies need to self-regulateSubscribe 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:Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTSentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWISTPilot - Visit https://www.pilot.com/twist and get $1,200 off your first yeaGreat 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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  • Magic School uses AI to help kids learn, not cheat | E2196
    Are AI tools in the classroom just time-savers, or can they have genuine educational value?In a must-watch TWiST 500 interview, Alex chats with Magic School founder (and former principal) Adeel Khan about how AI tools can make teachers more effective, and keep students inspired, without just doing all the work for them. He talks about turning an AI chatbot into a true assistant teacher, that keeps the lessons balanced yet challenging, and particularly empowers classroom novices and non-professionals.THEN… is 6 years too long for employees to wait to vest? Is this just another founder trying to reinvent EVERYTHING, just because they can’t resist? Ramp CEO Eric Glyman joins Jason and Alex to answer pressing founder questions from viewersPLUS there’s a new entrant in our Gamma Pitch Deck competition, and it’s so compelling, Jason can’t wait to invest! Kris Canete of On the Fly Energy tells us about America’s fragile power grid and his elegant solution: flywheel energy storage!Timestamps:0:00 - Welcome to TWiST!02:59 - Former principal Adeel Khan of TWiST 500's Magic School AI tells us why “teachers are magic”09:41 - Goldbelly ships America’s most delicious, iconic foods nationwide! Get 20% off your first order by going to Goldbelly.com and using the promo code TWiST at checkout.10:50 - How AI tools can particularly help out classroom novices and non-pros who are just getting started20:57 - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at Gusto.com/twist.26:58 - How Magic School stays ahead of shifting standards across different states and regions32:57 - Zite is the fastest way to build *business software* with AI. Build apps, forms, websites and portals that connect to the tools you already use. Go to *zite.com/twist* to get started.33:30 - Why the best feedback Adeel ever got came from a teenager36:30 - Making AI a true assistant teacher, that keeps lessons balanced yet challenging38:38 - Is a 6-year vesting schedule too aggressive? Eric Glyman responds.41:00 - When even ambitious founders should sometimes just accept a standard deal.57:33 - What IS flywheel energy storage?01:00:00 - Why Jason loves the Fly Energy Gamma pitch and wants to invest right now.01:34:13 - Gamma Outro*Subscribe to the TWiST500 newsletter: [https://ticker.thisweekinstartups.com](https://ticker.thisweekinstartups.com/)Check out the TWIST500: [https://www.twist500.com](https://twist500.com)Subscribe 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: [⁠  / alexwilhelm  ](  / alexwilhelm  )*Follow Jason:X:   / jason  LinkedIn: [  / jasoncalacanis  ](  / jasoncalacanis  )Great TWIST interviews: [Will Guidara,](   • Lessons in Unreasonable Hospitality with W...  ) [Eoghan McCabe](   • Great Builders & Success First with Interc...  ), [Steve Huffman](https://podcasts.apple.com/us/podcast..., [Brian Chesky](https://podcasts.apple.com/ca/podcast..., [Bob Moesta,](   • Decoding Customer Insights, Trust, and the...  ) [Aaron Levie](https://podcasts.apple.com/ca/podcast..., [Sophia Amoruso](https://podcasts.apple.com/ca/podcast..., [Reid Hoffman](https://podcasts.apple.com/ca/podcast..., [Frank Slootman](https://podcasts.apple.com/ca/podcast..., [Billy McFarland](https://podcasts.apple.com/ca/podcast...)*Check out Jason’s suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter:   / twistartups  YouTube:    / thisweekin  Instagram: [  / thisweekinstartups  ](  / thisweekinstartups  )TikTok:   / thisweekinstartups  Substack: [https://twistartups.substack.com](
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  • Today’s show: *Is the AI bubble going to POP? And if so, how much of our economy is it going to take down with it?On a new TWiST, Jason, Alex, and Lon debate the size and scale of the AI bubble, whether poppage is imminent, and just who we can blame for the last few economic crises. (HINT: Not the tech industry!)PLUS why Jason STILL thinks the current AI cycle will be the biggest in tech history, how this morning’s AWS mega-failure might impact the company’s earnings, the spread of AI fakes in the wake of this weekend’s No Kings march, why LLMs may soon put your broker out of business, and much much more.**Timestamps:** (00:02:26) Is AI a BUBBLE? And if so, how BIG?(00:05:12) Are all the major bubbles and corrections always Wall Street’s fault?(00:08:39) Why Jason thinks this AI will be the biggest cycle in the history of technology(10:00) LinkedIn Ads: Thanks to our partner @LinkedInMktg. Launch your first campaign and get $250 FREE when you spend at least $250. Go to [http://LinkedIn.com/ThisWeekinStartups](https://www.linkedin.com/thisweekinstartups) to claim your credit.(20:00) Thank you to our partner @trustvanta! TWiST listeners automate your SOC2 and get $1,000 off at http://www.vanta.com/twist(00:23:01) Will this morning’s AWS failure impact Amazon’s earnings?(30:00) Thanks to our partner @Openphone! Streamline and scale your customer communications with Quo. Get started free, plus get 20% off your first 6 months, at [http://quo.com/TWiST](http://quo.com/TWiSThttp://quo.com/perks/twist)(00:32:49) People couldn’t spot AI fakes from this weekend’s protests… are we cooked?(00:49:54) Jeremy Strong shows off his Mark Zuckerberg impression… and Jason is impressed*Thank you to our partners:LinkedIn Ads: Thanks to our partner @LinkedInMktg. Launch your first campaign and get $250 FREE when you spend at least $250. Go to [http://LinkedIn.com/ThisWeekinStartups](https://www.linkedin.com/thisweekinstartups) to claim your credit. @trustvanta! TWiST listeners automate your SOC2 and get $1,000 off at http://www.vanta.com/twist@Openphone! Streamline and scale your customer communications with Quo. Get started free, plus get 20% off your first 6 months, at [http://quo.com/TWiST](http://quo.com/TWiSThttp://quo.com/perks/twist)*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/thisweekinstartups](https://www.instagram.com/thisweekinstartups/)TikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: [https://twistartups.substack.com](https://twistartups.substack.com/)*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916All rights for the video shared and linked below belong to the original copyright holder, and we are using the footage under the principle of fair use.Listen here:Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audioMore from us:Twitter: https://twitter.com/twistartupsInstagram: https://www.instagram.com/thisweekinstartupsOfficial site: https://thisweekinstartups.comSubscribe to our YouTube to watch all full episodes:https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1Subscribe to TWiST Clips for all the best moments:https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg?sub_confirmation=1#startups #entrepreneurship #investing #angelinvesting #tech #news #business

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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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