Bill Gurley, Brad Gerstner, and Jason Calacanis discuss the impact of market downturns on startups, AI boom, chatbots' potential, and performance predictions for tech giants in 2024.

Dara Khosrowshahi, Bill Gurley, Brad Gerstner, & Jason Calacanis discuss Uber's growth, future plans, and finding the right CEO. They talk about Uber's early magic, Dara's initial reservations about joining, industry dynamics, the use of secondaries, and the importance of diversifying engineering talent for global growth.

Jason Calacanis, an influential internet entrepreneur and angel investor, discusses the impact of the modern media landscape on public opinion. He examines the transition from traditional journalism to podcasts, reflecting on media integrity and audience trust. The conversation dives into the polarized political climate, touching on immigration policy and political narratives. Calacanis emphasizes the importance of optimism and resilience amid adversity, while cautioning against the negative effects of technology on personal relationships.

Jason Calacanis, an angel investor and early backer of Uber, dives deep into Silicon Valley's political divide. He discusses how tech leaders are reacting to figures like Trump, revealing tensions between self-made entrepreneurs and elite groups. The conversation touches on the significant shifts following January 6th and the growing skepticism around cryptocurrency, emphasizing the need for better regulations. Calacanis also shares insights on the emotional currents influencing the upcoming elections, all while maintaining a light-hearted tone.

Trey Lockerbie chats with Angel Investing legend, Jason Calacanis. Jason is an entrepreneur who sold his second business Weblogs to AOL for $30MM in 2005. Jason then founded multiple other companies and along the way, became an angel investor in companies like Uber, Robinhood, Calm and 300 others give or take.IN THIS EPISODE, YOU'LL LEARN: 01:38 - The advantages of being an outsider. 06:10 - The realities of running a startup. 09:28 -What makes up a star founder and the ingredients for success. 13:32 - Why so many startups fail and how to look for the signs. 37:56 - Startup deal terms and syndicates. 45:31 - Common traits of Jason's many billionaire friends and colleagues. And a whole lot more! *Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. Angel Book. This Week In Startups Podcast. All In Podcast. The Syndicate Website. Inside Newsletter Website. Jason Calacanis Twitter. Trey Lockerbie Twitter. NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts.  SPONSORSSupport our free podcast by supporting our sponsors: River Toyota Range Rover Fundrise AT&T The Bitcoin Way USPS American Express Onramp SimpleMining Public Vacasa Shopify HELP US OUT!Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it!Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fmSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoicesSupport our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

We discuss why it's worth it to start a podcast and how to be a great host.

Again, this is a republishing of my Jason Calacanis interview from the Internet History Podcast.Sponsors:Bloomberg.com/careersSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This Week in Startups is presented by: Squarespace. Turn your idea into a new website! Go to http://squarespace.com/TWIST for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain. Trovata. Starting up is hard. Trovata makes managing cash easy. Start automating your cash management at http://trovata.io/TWIST.Use Code TWIST for 30% off one full year of premium features like AI forecasting. OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at http://openphone.com/twist Today’s show: Jason and Brad speak with Mubadala Capital’s Head of Ventures, Ibrahim Ajami, at Hub71 in the UAE. The three discuss how startups can survive and thrive in an economic downturn (1:02) before diving into the sacrifices that founders must make to create an incredible product. (14:16) They also explain how the AI revolution will affect software, startups, capital allocators, and more! (40:36) Follow Mubadala: https://twitter.com/MubadalaCapital Follow Ibrahim: https://twitter.com/IbrahimAjami Follow Hub71: https://twitter.com/hub71ad Follow Brad: https://twitter.com/altcap Time stamps: (0:00) Nick kicks off the show (1:02) Surviving the downturn (12:46) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST (14:16) Sacrificing to build a great product (26:34)Trovata - Use code TWIST at https://trovata.io/twist for 30% off one year of premium features, like AI forecasting (27:47) Brad’s letter to Mark Zuckerberg and AI creating ultra-efficient startups (39:02) OpenPhone - Get 20% off your first six months at https://openphone.com/twist (40:36) The AI revolution (50:48) The implications of AI on the software industry (55:50) Creating the Silicon Valley culture (59:32) Reflecting on the success of the Launch Accelerator (1:06:23) Building culture within your firm and dealing with failure (1:19:03) Opinions on WFH (1:25:05) Recognizing product velocity (1:29:11) Advice for young founders (1:34:47) Advice for founders in emerging markets Read LAUNCH Fund 4 Deal Memo & Apply for Funding Buy ANGEL Great recent interviews: Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Konstantine Buhler, Ana Marshall, and Jason Calacanis discuss VCs not raising funds, challenges for new fund managers, capital deployment, emerging managers, Cisco's $1B AI fund, AI applications, M&A vs. IPO investments, and Lightning round on latest investments

Exploring India's startup ecosystem, deep dive into Carta's 2018 startup class data, IPOs in the tech industry, analysis of sovereign wealth funds' approach to venture investing, evolving strategies in venture funding, optimizing startup investments for high returns, navigating complexities of VC and tech industry evolution