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This Week in Startups

Jason Calacanis
This Week in Startups
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  • AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211
    AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211Register for Founder University Japan’s Kickoff! https://luma.com/cm0x90mkToday’s show:*Will the arrival of two hotly-anticipated, intensely powerful AI models snap the Doomer cycle?On a new TWiST, Jason and Alex consider the current AI landscape, one where cynicism about insider mega-deals, fear of job displacement, and concerns about bubble bursts seem to rule the day. Will the arrival of two powerful new models — xAI’s Grok 4.1 and Google’s Gemini 3 — help the industry to course-correct? And how do we decide how much these models have improved anyway?PLUS we’re investigating Cloudflare’s recent downtime and their acquisition of Replicate. Are we heading toward a future in which everyone runs their own models, locally? And how worried should founders get if their products or sites go down for a few hours?Finally, if you’re an investor, and want to come to Jason’s Dim Sum Demo Day in San Francisco, here’s the link: http://launch.co/dimsumTimestamps:(2:01) Why the internet got broadly degraded when Cloudflare went down(5:00) How worried should founders become when their sites go offline?(6:44) Downtime aside, what did Cloudflare want with Replicate?(8:12) Why Jason predicts one day we’ll run our own local language models(9:39) Goldbelly - 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.(15:25) How to turn off “Learn From This App” on your iPhone(17:29) Will the arrival of hotly-anticipated new models stop the spread of Doomerism and AI cynicism(20:00) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(23:53) Checking back in with the “Best AI Model” Polymarket… why has ChatGPT dropped so low?(29:43) Zite - 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.(31:14) ANOTHER AI mega-deal? Nvidia and Microsoft are investing in… ANTHROPIC(33:06) Why so many AI deals now include “up to…” language around investments(35:04) What Jason thinks of Dario Amodei’s warning about white collar job displacement(39:39) If we all agree AI job displacement is coming… what can be done?(45:16) All about Jason’s Dim Sum Investor Demo Day in San Francisco!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:(9:39) Goldbelly - 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.(20:00) Every.io - For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit every.io.(29:43) Zite - 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.Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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  • Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210
    *Are we finally reaching Peak eVTOL? Jason and Alex on Joby’s big Abu Dhabi moves and Archer’s purchase of LA’s Hawthorne Airport.On a PACKED Monday TWiST, Jason is BACK from MENA and Tokyo. Hear tales from his whirlwind trips launching new Founder University satellite programs… and find out why construction and fintech are BOOMING across the Middle East.PLUS Ramp raised $300M… here’s why Alex calls the round “pretty baller.” We question why AI companies are growing SO MUCH FOUNDER than their SaaS counterparts. We’re digging into the Problem with Dropbox.AND we’re saying goodbye to KitKat, the beloved SF bodega cat who was reportedly run over by a Waymo. Here’s why Jason’s not too broken up about it (but he’s JUST JOKING!)👉  Register here for Founder University Japan’s kickoff: https://luma.com/cm0x90mkToday’s show:Timestamps:(2:17) Big takeaways from Jason’s MENA Founder University trip(6:54) Why construction and fintech are booming across the Middle East(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(12:35) Everything was very different at Founder University Japan! It’s coming in January.(15:59) Ramp raised $300M at a $32B valuation… why Alex says it’s “pretty baller”(17:15) Ramp says AI agents are making money more intelligent… the heck does that mean?(19:26) We’re building more space for machines than humans now… and why Jason’s not sure this will last(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(23:41) Why AI is growing SO MUCH faster than even top SaaS companies(25:32) The Problem with Dropbox…(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.(32:39) Jason ate his way across Tokyo… here’s all the deets(33:16) RIP KitKat, beloved SF bodega cat killed by a Waymo(39:03) So who SHOULD get to make decisions about local roads?(44:15) Dario Amodei from Anthropic shares Jason’s concerns about AI job displacement(52:02) What’s going on with crypto prices? Is this vibe-based? Just based on the wider economy?(58:14) Viewer questions: What strategies should founders employ in the current fundraising landscape?(1:02:42) Bezos RETURNS to the C-Suite. What IS “Project Prometheus”?(1:10:24) Jason thinks Bezos still returns to Amazon at some point… or runs for President.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:(9:56) Netsuite. The business landscape is very chaotic right now. That’s why you need NetSuite, by Oracle. Download the CFO’s Guide to AI and Machine Learning for free at https://www.netsuite.com/twist(19:48) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(30:21) DevStats - DevStats integrates your dev work and your business goals into a shared language that everyone can understand. Get 20% off, plus access to their dedicated Slack channel. Just go to https://www.DevStats.com/twist.Check 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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  • Stop ghosting your friends with Nox’s RPLY, plus Alloy Automation and a Shopify flashback | E2209
    👉 Register here to join Founder University Japan’s kickoff: https://luma.com/cm0x90mkToday’s show:Nox’s new app RPLY reminds you to text your friends back, getting you to iMessage inbox zero.On today’s TWiST, we’ve got Molly Cantillon of Nox, telling us how she plans to make lackadaisical texters (like our co-host Alex) more effective, even if it means breaking into Apple’s walled garden. Hear about how RPLY maps your relationships so that it can understand your messages contextually, and help you stay organized.Then, Gregg Mojica of Alloy Automation swings by the show to dispel some common myths about AI agents. For the most part, these little machine learning helps aren’t truly autonomous… Hear how Alloy’s agents decide when it’s time to bring in a human for help. PLUS is AI in a “lull” right now? Hear why Gregg thinks there’s still a LOT of room for these apps to improve.Finally, it’s another TWiST Flashback. We’re jumping back to 2013 for an eye-opening chat between Jason and Shopify founder/CEO Tobi Lutke. Hear some fascinatingly prescient takes on the rise of SaaS, how early Shopify differentiated itself from other ecommerce and website building solutions, AND why Tobi dreamed of making Ottawa a true tech hub.Timestamps:(02:57) Molly Cantillon of Nox is trying to help you get better at texting(04:01) How RPLY gets even chaotic texters like Alex more organized(05:10) The complexities of entering into Apple’s “walled garden”(07:20) Keeping RPLY safe, in case you’re using it for work!(09:24) Miro - Help your teams get great done with Miro. Check out miro.com to find out how!(11:59) How RPLY uses relationship mapping to understand and prioritize your messages(19:23) Perspective AI - Real insights, straight from your customers, and your first two months are on us. Just go to getperspective.ai/twist.(21:08) Why Nox wants its AI to become “the Invisible OS.”(29:30) Pilot - Visit https://www.pilot.com/twist and get $1,200 off your first year.(30:40) We’ve got Gregg Mojica of AI agent makers Alloy Automation(31:42) How the rise of AI agents changed the core of Gregg’s business(34:03) Why most AI agents still aren’t truly autonomous(35:00) How Alloy’s agents decide when to bring in a human for help(37:02) Why the rapid acceleration of AI development has made some enterprises pump the brakes(39:00) Is AI in a “lull” right now? Why Gregg thinks there’s still room to improve.(40:31) How close are we to AI apps going truly mainstream?(43:41) Why Alloy Automation didn’t raise a massive round like so many of its AI peers? (Or are they?!)(46:48) The difficulty of hiring in today’s AI landscape(50:21) In today’s TWiST Flashback, we’re revisiting Tobi Lutke of Shopify’s appearance from way back in 2013!(52:11) Why Shopify switched from selling snowboards to storefronts(59:37) Turning Ottawa into a tech hub, and the “secondary market” theory(1:05:32)The constant tension between growing your global footprint and expanding your features(1:08:52)Who were Shopify’s actual rivals?
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  • Why We Need Ferries and Tugboats in Space w/ Orbital Operations | E2208
    👉 Register here to join the kickoff: https://luma.com/cm0x90mkToday’s show:Just getting our stuff into orbit isn’t enough… Orbital Operations wants to help companies take things HIGHER.In today’s TWiST 500 interview, Alex chats with Ben Schleuniger, whose startup Orbital Operations is solving the complexity of space logistics. The advent of reusable rockets has made it easier and cheaper than ever for us to place objects in Low Earth Orbit (or LEO).But what if we want to reach higher orbits? That’s a much more challenging issue: space is already kind of CROWDED, and not all of our vehicles can carry enough fuel to power them that far out into the cosmos.Orbital’s fix? Cryogenic orbital maneuvering vehicles (or OMVs) like the Astraeus, which uses hyper-efficient propulsion systems, allowing them to travel further and faster speeds, and even potentially get refueled in orbit.Learn more about this fascinating tech PLUS we’re looking back at classic Jason interviews with Greg Brockman of OpenAI and Vlad Tenev of Robinhood, AND checking in with Oliver’s latest This Week in AI demo for Character AI’s blockbuster conversational chatbots.Timestamps:(02:56) Alex opens the show with Ben Schleuniger, co-founder of space tech startup Orbital Operations(03:47) Why is movement within orbit such a challenging problem?(4:28) The key importance of launch vehicle reusability(07:05) How Orbital’s Astreaus vehicle utilizes cryogenic propellants… and why(08:49) The secret to keeping those propellants cool(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(13:57) How Orbital is preparing for their Series A, and how they plan to spend the cash(20:37) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(28:09) TWiST FLASHBACK: Revisiting OpenAI Greg Brockman’s visit from 2018(31:31) 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.(37:57) How GPUs unlocked the AI revolution(35:02) Tackling early concerns about deepfakes(41:17) Looking ahead to the dawn of AGI(50:05) AI DEMO: Oliver stops by to walk us through Character AI’s key features(50:51) Watch as Oliver simulates a chat with former President Barack Obama(53:30) How to use ChatGPT to enhance your Character AI prompts(56:57) TWIST FLASHBACK with Robinhood’s Vlad Tenev from May 2017(57:14) Back then, Robinhood was valued at a mere $1.3 billion!(59:21) How Robinhood made financial transactions SO MUCH FASTER than they used to be(1:00:57) When Robinhood realized they had Product Market Fit… via Hacker News!(1:06:44) The magic of being better, faster, and cheaper(1:08:12) This segment was filmed BEFORE Robinhood offered crypto(1:11: 08) Jason’s Eagle Computer Speech and how to avoid “Taj Mahal Syndrome”Check 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/alexwilhelmThank 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/TWISTNorthwest 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!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.
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  • Inside Harvey AI’s $8 billion AI lawyer app, PLUS How OpenRouter unites the LLMs | E2207
    Register for Founder University Japan’s Kickoff! https://luma.com/cm0x90mkToday’s show:Find out why AI is perfectly suited to legal tasks… despite being too fast for “billable hours”On today’s TWiST, Alex takes a deep dive into LLM Law with Harvey AI co-founder/president Gabe Pereyra. It turns out, much like software development, doing legal work relies on learning specialized language and sifting through a dense and expansive corpus of information… making it an IDEAL use case for LLMs.Buuuuut AI works so fast… the current structure of legal payments (billable hours) no longer applies. Find out how Harvey is working around these challenges — and what they plan to do if OpenAI decides to get into the legal game — in this fascinating interview.THEN, Alex chats with another AI visionary — OpenRouter co-founder and CEO Alex Atallah — who allows developers to plug and play all the major models into their applications. Find out why specialized LLMs trained for “resourcefulness” are coming into fashion… why benchmarks and evals have become so crucial to the industry… AND whether we’ll end up spending as much on AI inference as the human workers it’s replacing… in this essential discussion.PLUS Jason stops by for some more Founder Q’s!Timestamps:(0:00) Welcome back to TWiST!(1:32) Alex kicks off the show with Harvey AI co-founder and President Gabe Pereyra to talk about applying AI to the legal profession(4:52) How major international law firms (and their enterprise clients) fueled Harvey’s mega-growth(6:54) Why LLMs are perfectly suited for legal work(9:24) 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.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.(17:22) Looking ahead: expanding beyond the law.(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist(21:44) The problem: AI can’t charge “billable hours”… it’s too fast!(23:44) Will the major AI players like Google and OpenAI build their own version of this?(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(30:41) Alex welcomes OpenRouter co-founder and CEO Alex Atallah, whose rankings he loves and uses all the time(33:10) Why Alex says we’re seeing more specialized LLMs trained for more “resourcefulness”(36:05) How increased competition and diversification makes things tougher for developers(41:09) Alex suggests that new models are exciting for users, like product launches used to be(42:29) OK, let’s get into it… How does OpenRouter make money?(45:38) Understanding what kinds of training data the AI companies want the MOST(47:47) The important currency of evals and benchmarks(49:13) Why OpenRouter is ramping up its LLM recommendation engine(53:44) Will AI inference spend end up costing as much as the humans it’s replacing?(56:49) Time for a Founder Q! What should founders do about quick vibe-coded competitors?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/alexwilhelmThank you to our partners:(9:24) 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.x and build next. Head to Enterpret.com/twist to book a demo and see it in action.(20:42) Uber AI Solutions - Your trusted partner to get AI to work in the real world. Book a demo with them TODAY at Uber.com/twist(29:53) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
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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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