Ask Jason LIVE!: Unpacking Startup Strategies with Real-Time Q&A | E1921

This Week in Startups is brought to you by… Squarespace. Turn your idea into a new website! Go to https://www.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. 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://www.openphone.com/twist Eppo. Experimentation is how generation-defining companies win. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist * Todays show: Jason kicks off Ask Jason live! Six live guests ask questions on key topics, including prioritizing multiple founders (13:28), advice around moat for a startup (52:42), and whether not focusing on AI in a pitch will affect investment chances (1:02:38). * Timestamps: (0:00) Jason kicks off another Ask Jason with 6 live guests! (1:13) Sean asks about investment firms changing how they invest early on. (11:42) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist (13:28) Pierson of jellypod asks about prioritizing multiple founders for investments or accelerators (22:54) OpenPhone - Get 20% off your first six months at http://www.openphone.com/twist (24:47) Ann asks if they should raise venture capital to grow faster even though it means giving up some company ownership. (32:01) Eppo. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist (39:56) Francis asks how to strike a balance between skepticism and enthusiasm when evaluating a company for investment, given that it's impossible to invest in every company. (52:42) Hosum asks if explaining their startup's moat as current execution and future benefits after reaching product-market fit is enough to convince investors. (1:02:38) Thom asks if not highlighting AI in our funding pitch will hurt our chances of getting investment. * Send us your questions for the next episode of Ask Jason LIVE! http://www.thisweekinstartups.com/askjason * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Thank you to our partners: (11:42) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist (22:54) OpenPhone - Get 20% off your first six months at http://www.openphone.com/twist (32:01) Eppo. Accelerate your experimentation velocity with Eppo. Visit http://www.geteppo.com/twist * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups * Subscribe to the Founder University Podcast: https://www.founder.university/podcast