This Week in Startups

• GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

  Today’s show:Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about.First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair?PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH MUCH MORE.Timestamps:(0:00) Why Jason thinks Apple lacks innovation (plus a look back at his 2019 thoughts)(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(09:54) Show continues…(20:10) 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!(21:18) Is GPT-5 coming for Lovable and Bolt?(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.com/Twist.(30:55) Show continues…(35:05) Ripple buying Rail, and why sometimes regulations are GOOD for companies(43:28) Is Ripple about to become the MicroStrategy of XRP?(47:48) Truth Social AI is perplexing, powered by Perplexity(53:27) Should people be using ChatGPT for therapy? What do you think? How does that make you feel?(01:04:42) Anthropic’s Dario Amodei recalls his greatest haters(01:11:04) Bumble but… for friendship?(01:12:20) DoorDash’s crazy growth, and the guys discuss who should buy AirbnbSubscribe 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:(08:54) Sentry - New users get 3 months free of the Business plan (covers 150k errors). Go to http://sentry.io/twist and use code TWIST(20:10) 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!(29:42) Alphasense - Get deeper insights into your business with the power of AI search and market intelligence. Start with a free trial at AlphaSense.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

  --------  

  1:18:40

  --------

  1:18:40
• Communist coffee hits NYC, RIP Hulu, GPT-5 arrives and more | E2161

  Today’s show:It’s a brand-new PACKED episode of TWiST. Jason and Alex welcome guest Zach Dive of Adam.new, to tell us why he made a deepfake AI ad starring Jason and the All-In besties.PLUS a rundown of the biggest tech and startup news of the day, including Disney’s decision to sunset Hulu, OpenAI’s new open-weight models, the Cloudflare vs. Perplexity feud, Uber’s newly-announced stock buyback, China’s Luckin Coffee coming to Manhattan, and much much more!Timestamps:(0:00) Luckin Coffee hits NYC… along with COMMUNISM?!(09:15) Is China taking on major American brands on PURPOSE?(10:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(11:29) Show Continues…(20:17) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(21:30) Show Continues…(26:02) RIP HULU: Why Disney is sunsetting the iconic app.(28:37) Nostracanis Returns: Jason’s 2017 Disney vs. Netflix predictions came true(30:24) .TECH - Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(31:28) Show Continues…(35:39) Zach Dive of Adam.new joins to tell us about making a viral deepfake ad starring JCal and the Besties(44:10) Zach shares thoughts on AI and copyright, and why it’s a problem for the “big dogs,” not him… yet(48:12) Jason wants to wet his beak… but is there room in the Adam.new seed round?(53:07)OpenAI’s new models are open-WEIGHT; how that’s different from open-source.(58:36) Do Nvidia and Apple devices NEED kill switches and backdoors? Why it’s such a tough question.(01:02:10) GPT-5 arrives TOMORROW?!(01:03:31) Cloudflare vs. Perplexity… let them fight?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:(10:16) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:17) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech(30:24) .TECH - Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain 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.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

  --------  

  1:13:06

  --------

  1:13:06
• Lina Khan’s Figma victory lap, Meta’s Superintelligence Team, BYD mega car-carrier video & MORE | E2160

  Today’s show:Jason and Alex are running down the biggest tech, startup, and business stories of the day on a brand-new Monday TWIST.Which countries are leading the AI race, based on academic papers? Why Jason thinks covert agencies are spying on Meta’s superintelligence team. Lina Khan’s taking a victory lap on the Figma IPO but what did she REALLY accomplish during her Biden administration tenure? PLUS, why we’re bringing Founder University to the MENA region.All that and MORE on a packed episode! Find out why we’re the #1 podcast for startups and founders.Timestamps:(0:00) Why Jason is attending more TV poker tournaments(4:02) Did you know Founder University is headed to MENA? Calling all Riyadh founders.(10:01) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:27) Show Continues…(19:52) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠⁠(21:01) Why Jason doesn’t think Lina Khan deserves her Figma IPO victory lap.(23:17) Jason thinks Figma is overpriced: how quickly could a rival build a competitor?(27:53) For an investor, there’s a huge difference between a home run and a GRAND SLAM.(30:42) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com/TWIST(31:55) Show Continues…(40:59) Why Jason thinks covert agencies are spying on Meta’s global Superintelligence Team…(50:43) Which countries are leading the AI race in terms of research? Producer Claude helps with the answer.(57:12) Fact-checking the viral BYD TikTok: can their self-driving cars really drive themselves off the ship?(59:52) Jason and Alex check out some of their dream carsSubscribe 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:10:01) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:52) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist⁠⁠⁠(30:42) Monarch Money - Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.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

  --------  

  1:09:00

  --------

  1:09:00
• TWiST 500 interviews with Cortical Labs, Turing, AND Mercor | E2159

  Today’s show:Alex is back with three more awesome interviews with founders on the bleeding edge of innovative tech.Dr. Hon Weng Chong walks us through the basics of biological computing and Cortical Labs’ first-ever commercial computer running on living human cells.Turing founder Jonathan Siddarth unpacks the secrets of LLM benchmarking, and explains why even our most advanced tests need to get much much harder right away.Finally, Mercor founder Brendan Foody on how AI is about to reinvent the hiring process, and marrying the effectiveness of recruiters with the ease of online job boards.It’s three — count ’em, three — can’t miss TWiST interviews guaranteed to make you smarterTimestamps:(0:00) OpenAI’s GPT-5: When is it coming out? Is it going to be TOO smart?(08:06) Cortical Labs’ Hon Weng Chong on the electric connection between neuroscience and machine learning(10:20) 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!(11:27) Show Continues…(15:17) The extreme difficulty of going from the lab to a shippable product(20:00) .TECH: Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(21:05) Show Continues…(28:15) Why data is a factor of time(29:52) 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(31:16) Show Continues…(42:44) Turing CEO Jonathan Siddarth explains why it’s so important to keep benchmarking our LLMs(47:24) What it means when a model “saturates” a test, and why benchmarks need to get HARDER(50:22) What happens with the LLMs can answer all of our smartest questions?(53:44) AI Agents train in gyms? Wait, really?(01:01:33) Coding teaches models how to think, and more training mysteries don’t understand(01:03:11) Brendan Foody from Mercor explains the “matching problem” that makes hiring such a pain(01:07:02) How Mercor combines a job board’s distribution with the value of a recruitment agency(01:10:49) Brendan recalls building his first AI interviewer in his college dorm(01:20:16) Mercor has the opposite of a retention problem and crazy growthSubscribe 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:(10:20) 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!(20:00) .TECH: Say it without saying it. Head to www.get.tech/twist or your favorite registrar to get a clean, sharp .tech domain today.(29:52) 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

  --------  

  1:23:29

  --------

  1:23:29
• All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

  Today’s show:It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more!It’s an essential watch for anyone building or investing in companies in 2025!Timestamps:(0:00) Introducing our amazing investor panel!(03:15) The panel shares their First Fund experiences(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(11:27) Show cont…(12:46) Where we’re at on the investor Greed-Fear Index(13:54) The delicate art of investor discipline(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(21:59) Sophia’s criteria for a follow-on investment(24:17) Founders are going direct on social media(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.(30:49) Show cont…(32:33) Why we’re seeing so many more Series Bs(33:30) So when do you trim a position?(39:35) There are SO MANY COMPANIES! Why surface area matters.(43:25) Durable vs. brittle revenue and how to tell them apart(46:15) When it’s time to angel invest outside your fund(49:04) The panel’s approaches to capital recycling(57:15) The benefits of co-working “jam sessions”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:(10:03) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(20:47) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(29:35) Public - Take your investing to the next level with Public. Build a multi-asset portfolio and earn 4.1% APY on your cash—with no fees or minimums. Start now at public.com/twist.DISCLAIMER*All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.Rate as of 7/18/25. APY is variable and subject to change.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/thisweekinstartups

  --------  

  1:13:43

  --------

  1:13:43

More Technology podcasts

Trending Technology podcasts

About This Week in Startups