Mastering Venture Capital and Founder Strategies with Rory O’Driscoll and Mark Suster

This Week in Startups - A podcast by Jason Calacanis

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This Week in Startups is brought to you by… Northwest Registered Agent. Start your business fast and secure with Northwest Registered Agent! In just 10 clicks and 10 minutes, set up your entire business identity—name, address, mail service, phone, email, website, and domain. Everything You Need to Launch Your Business in Minutes! For just $39 plus state fees, Northwest will handle your complete business identity. visit https://www.northwestregisteredagent.com/twist Wistia - The all-in-one video platform for business, with tools that help you create, manage, and measure the impact of your videos. Try Wistia for free at https://www.wistia.com/startups1 HiddenLayer - Generative AI is revolutionizing industries. HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Helping you generate more – by enabling seamless & secure Generative AI. Visit https://www.HiddenLayer.com/TWiST to learn more. * Todays show: Rory O’Driscoll joins guest host Mark Suster to discuss: advice for founders with traction but not yet booming (2:33), thirty years of internet cycles and their impact on venture capital (13:25), the approach to big-picture thinking vs. immediate traction and strategizing exits (36:58), and more! * Timestamps: (0:00) Rory O’Driscoll joins guest host Mark Suster. (2:33) Rory’s advice for founders with traction but not yet booming. (9:09) Aligning incentives between founders and venture; reminding CEOs to be "selfish.” (10:23) Northwest Registered Agent - For just $39 plus state fees, Northwest will handle your complete business identity. Visit https://www.northwestregisteredagent.com/twist today. (13:25) Reflections on thirty years of internet cycles and their impact on venture capital. (18:25) Debating AI: Does it favor the incumbents? (20:07) Wistia - Try Wistia for free at https://www.wistia.com/startups (21:35) What Rory and Scale Venture looks for when investing in AI. (26:20) How OpenAI has changed the landscape (29:18) HiddenLayer - HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://www.HiddenLayer.com/TWiST to learn more. (30:30) Debating “faux-mentum” vs. long-term sustainability in investments. (34:34) Balancing deep passion and business savvy when evaluating founders. (36:58) Rory’s approach to big-picture thinking vs. immediate traction and strategizing exits (44:02) The importance of picking vs. price discipline. (1:00:58) Advice for founders dealing with “busted cap tables.” (1:08:07) Rory’s advice for his younger self. * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Check out Scale Venture Partners: https://www.scalevp.com/ * Follow Rory: X: https://x.com/rodriscoll LinkedIn: https://www.linkedin.com/in/roryodriscoll/ * Follow Mark: X: https://twitter.com/msuster LinkedIn: https://www.linkedin.com/in/marksuster/ * Thank you to our partners: (10:23) Northwest Registered Agent - For just $39 plus state fees, Northwest will handle your complete business identity. Visit https://www.northwestregisteredagent.com/twist today. (20:07) Wistia - Try Wistia for free at https://www.wistia.com/startups (29:18) HiddenLayer - ****HiddenLayer’s AI Detection & Response Solution secures your Generative AI & LLMs from malicious attack. Visit https://www.HiddenLayer.com/TWiST to learn more. * 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

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