Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, ...
Today’s show: Jason and Alex break down the latest head-scratching SEC ruling on meme coins—did they just legalize pump-and-dumps to protect Trump’s token? Plus, they dive into why venture debt can destroy startups, the rise of AI-driven companies, and how Tesla is gearing up to challenge Waymo in the self-driving car race. Then, Brandon Brown from GRIN joins the show to talk about scaling to 8-figure revenue, surviving brutal market corrections, and why he’s stepping down as CEO after a decade. This one’s packed with insights for founders, investors, and anyone watching the future of crypto, startups, and AI unfold.*Timestamps:(0:00) Jason and Alex kick off the show!(1:39) Palmer Luckey feud, and supporting Trump in Silicon Valley(9:36) AI's impact on startup growth and job displacement(10:11) Paddle. Go to https://www.paddle.com/twist to get started with your exclusive listener fee-free period.(12:20) Product market fit and Salesforce productivity(15:01) Howey Test and its application to cryptocurrencies(20:07) LinkedIn Ads. Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(26:13) Jason's libertarian views on meme coins(31:13) Hubspot for Startups. Get up to 75% off plus 3 months of Perplexity AI for free. Go to https://www.hubspot.com/startups(32:16) Meme coin regulation and political implications(37:22) GRIN's Brandon Brown interview and company evolution(46:10) Leadership changes and challenges at GRIN(53:28) Venture debt risks and business cycle preparedness(59:00) Leadership skills and defining reality(1:04:13) Updates on Waymo and autonomous rides(1:09:06) Tesla and the global autonomous vehicle market*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*Check out GRIN: https://grin.co/Checkout Angel University with Jason Calacanis & Mike Savino: https://www.angel.university/Check out the Founder Friday City Competition: https://www.founderfridays.tech/city-competition*Follow BrandonX: https://x.com/Brandon_BrownLinkedIn: https://www.linkedin.com/in/brandon-brown-0898731/*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:(10:11) Paddle. Go to https://www.paddle.com/twist to get started with your exclusive listener fee-free period.(20:07) LinkedIn Ads. Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups(31:13) Hubspot for Startups. Get up to 75% off plus 3 months of Perplexity AI for free. Go to https://www.hubspot.com/startups*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
--------
1:14:49
The Incredible Double Interview: Superhuman and Robinhood | E2090
Today’s show: Jason interviews Rahul Vohra, CEO and founder of Superhuman, and Vlad Tenev, CEO and co-founder of Robinhood. This is a packed episode featuring founder tips, fun stories about how Superhuman and Robinhood got their start and much more!Timestamps:(0:00) Episode teaser(2:13) Product market fit and founder journeys(3:25) Jason's investment in Superhuman and market positioning(5:14) AI's role and features in Superhuman(10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(14:37) Targeting users and competitive advantages(22:23) Evolution and new features of Superhuman(20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(24:37) Tackling spam with Superhuman's AI(27:05) Custom auto labels and email classification(29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits(32:03) Superhuman's auto reminders and drafts(34:14) Vlad Tenev and the origins of Robinhood(39:31) Product design philosophies of Robinhood and Superhuman(49:29) Scaling design principles and investment decisions(52:31) Subjectivity in product design(55:14) Customer feedback in product development(1:00:00) Superhuman's subscription model and customer acquisition(1:05:11) PR strategies and news hijacking(1:12:06) Investment experiences with Robinhood(1:13:35) Navigating company valuation fluctuations(1:15:03) Influences on Vlad Tenev and new Robinhood desktop product(1:22:02) Company resilience and employee reorganization(1:25:52) Crypto regulation and startup mentality(1:30:05) Investment trends among Robinhood users(1:31:12) Retail benefits for startups and capital raising challenges(1:34:04) Accreditation for private investing and solutionsSubscribe 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 this episode:Check out Superhuman: https://superhuman.com/Check out Superhuman’s blog post that details all of the new features Rahul went over in the demo: https://blog.superhuman.com/the-next-superhuman-ai/. Check out Robinhood Legend: https://robinhood.com/us/en/legend/Article “How Superhuman Built an Engine to Find Product Market Fit”: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/Check out Rick Rubin’s book: https://www.amazon.ca/Creative-Act-Way-Being/dp/0593652886Article on Bezos and Washington Post: https://www.newsweek.com/bezos-makes-big-change-washington-post-opinion-focus-endorsed-musk-2036618Media Bias Chart: https://www.allsides.com/media-bias/media-bias-chartCheck out “Working Backwards” book about Amazon insights: https://www.amazon.ca/Working-Backwards-Insights-Stories-Secrets/dp/1250267595Check out Rahul’s article on acquisition: https://www.linkedin.com/pulse/rip-mailbox-founders-how-stop-worrying-love-being-acquired-vohra/Follow Rahul:X: https://x.com/rahulvohraLinkedIn: https://www.linkedin.com/in/rahulvohra/Follow Vlad:X: https://x.com/vladtenevLinkedIn: https://www.linkedin.com/in/vlad-tenev-7037591b/Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!(29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits
--------
1:38:42
Apple Drops $500B on AI while Google Gemini Eyes Your iOS Devices! | E2089
Today’s show: Jason and Lon break down the latest trends shaping AI training, the evolving job market, and the shifting landscape of social media. A tribute to Steve Jobs on what would have been his 70th birthday explores his lasting impact, Apple’s massive $500 billion AI investment, and the future of US manufacturing. The conversation dives into Outlier’s role in AI training data, its effects on journalism, and broader job market implications. Jason also shares insights on autonomous vehicles, Apple’s AI strategy, and the latest in crypto—covering meme coins, regulatory battles, and the state of angel investing. Plus, a look at Oscar season and the cultural moments making waves.*Timestamps:(0:00) Jason and Lon kick off the show!(2:59) TikTok discussion and Steve Jobs' 70th birthday tribute(4:36) Jason's history with Steve Jobs and impact of blogging(8:56) Jason's interaction with Steve Jobs about podcast monetization(10:13) 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) Steve Jobs' legacy and Apple's innovation(14:12) Apple's $500 billion investment in AI and TSMC chip manufacturing(20:08) Vanta. Get $1000 off your SOC 2 at https://www.vanta.com/twist(21:18) Geopolitical implications of Apple's US manufacturing investments(24:06) Outlier's role in AI training data and legal risks(27:02) Journalists in AI training and job market implications(30:40) Vapi. Go to https://www.vapi.ai and use code Twist200 to get $200 in credits(32:39) Outlier’s AI training recruitment and global reach(34:14) AI's future in various industries(36:53) Experiences with autonomous vehicles and Waymo(37:23) Hot-swappable LLMs and Apple's AI integrations(41:03) Commercial implications of AI deals for Apple(43:08) Public access to podcast docket and meme coins discussion(47:03) Milei’s meme coin and libertarian views on crypto(52:15) Crypto trader's tragic incident and dangers of investing on margin(58:19) Jason's gambling habits and future of crypto regulation(1:01:05) Angel investing and Oscar season discussion*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*Follow Lon:X: https://x.com/LonsLinkedIn: https://www.linkedin.com/in/lonharris*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(10:13) Squarespace. Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(20:08) Vanta. Get $1000 off your SOC 2 at https://www.vanta.com/twist(30:40) Vapi. Go to https://www.vapi.ai and use code Twist200 to get $200 in credits*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
--------
1:07:57
Castelion Hypersonic Missiles and Crunchbase’s AI Powered Predictions | E2088
This Week in Startups is brought to you by…Squarespace. Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWISTLinkedIn Jobs. Post your first job for free at https://www.linkedin.com/twistAdQuick. Visit https://adquick.com/twist and mention TWIST to get $1000 off your first campaign.Today’s show: Jason interviews Bryon Hargis, CEO of Castelion, about the United State’s hypersonic technology gap with China, how we’re catching up and what it will take to win the hypersonic missile race. Alex interviews Jager McConnell, CEO of Crunchbase, about their newly released, scary accurate, AI powered predictive models.Timestamps:(0:00) Episode teaser(1:14) Introduction of Byron Hargis and Castellion's mission(2:20) Significance of hypersonic munitions(5:55) Impact and challenges of hypersonic systems in defense(7:16) Castellion's development and cost of hypersonic weapons(9:39) Squarespace. Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(12:28) Shift in defense contracting and venture backing(18:25) Sales strategies and founder insights in defense startups(19:38) LinkedIn Jobs. Post your first job for free at https://www.linkedin.com/twist(21:10) China's manufacturing capabilities and defense paradigm shifts(24:37) Role of automation and robots in manufacturing(28:58) AdQuick. Visit https://adquick.com/twist and mention TWIST to get $1000 off your first campaign.(31:37) Crunchbase's transition to predictive insights(38:01) Crunchbase's technology stack and AI models(41:36) Financial implications of AI-first model for Crunchbase(48:43) AI integration challenges and financial performance(52:50) AI-driven predictions and their accuracy(54:24) Future prospects for Crunchbase: Acquisition vs. IPO(55:22) Upcoming guests: Vlad from Robinhood and Raul from SuperhumanSubscribe 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/v19fcpCheckout Castelion:X: https://x.com/CastelionCorpWebsite: castelion.comCheckout Crunchbase:X: https://x.com/crunchbaseWebsite: https://www.crunchbase.com/Follow Bryon:X: https://x.com/hargsbLinkedIn: https://www.linkedin.com/in/cbh/Follow Jager:X: https://x.com/jagermcconnellLinkedIn: https://www.linkedin.com/in/jager/Follow 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) Squarespace. Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:38) LinkedIn Jobs. Post your first job for free at https://www.linkedin.com/twist(28:58) AdQuick. Visit https://adquick.com/twist and mention TWIST to get $1000 off your first campaign.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
--------
55:56
EV Truck Startup Nikola Runs Out of Juice | E2087
This Week in Startups is brought to you by…Gusto. Get three months free when you run your first payroll at http://gusto.com/twist*Gusto pricing shown in ad is based on pricing prior to March 2025Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twistAtlassian. Head to https://www.atlassian.com/software/startups to see if you qualify for 50 free seats for 12 months.Today’s show: Jason and Lon Harris cover Nikola’s Chapter 11 and how founders can avoid the same mistake, Superhuman AI’s new features, Mira Murati’s Thinking Machines and where Sam Altman went wrong holding onto top talent, plus much more!Timestamps:(0:00) Episode teaser(1:26) Introduction to startup news and trends(2:47) Bill Ackman's J trade and Herbalife controversy(5:24) Comparing trading strategies: Jason vs. Pelosi(9:49) Gusto. Get three months free when you run your first payroll at http://gusto.com/twist(11:29) HP's acquisition of Humane and its significance(13:52) Challenges facing the AI industry(20:30) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(21:47) OpenAI veterans launch a new venture(28:09) Chamath's venture into high stakes poker(29:35) Atlassian. Head to https://www.atlassian.com/software/startups to see if you qualify for 50 free seats for 12 months.(36:37) Nikola's Chapter 11 filing and securities fraud(48:10) The upside of failing as a founder in the U.S.(50:24) Superhuman introduces AI-powered email features(51:58) Preview of upcoming guests on the podcast(53:03) Key characteristics of successful founders(56:21) Play-along: Guess the fake startup(1:04:12) Movie trilogy rankings: Superman, Star Wars, TerminatorSubscribe 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/v19fcpCheck out these past Guess The Fake Startups segments:https://www.youtube.com/watch?v=iKP2iiF1oYIhttps://www.youtube.com/watch?v=rhnOXuGnh14https://www.youtube.com/watch?v=ueazpyGOgccFollow Lon:X: https://x.com/alexFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(9:49) Gusto. Get three months free when you run your first payroll at http://gusto.com/twist*Gusto pricing shown in ad is based on pricing prior to March 2025(20:30) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(29:35) Atlassian. Head to https://www.atlassian.com/software/startups to see if you qualify for 50 free seats for 12 months.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
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.
New Zealand