The Social Radars

Jessica Livingston
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Aug 29, 2025 • 24min

Founder Mode: Jake Heller, Founder & CEO, Casetext

Jake Heller, Founder and CEO of Casetext, shares his journey in transforming legal technology and navigating through multiple pivots over ten years. He reveals how an intensive weekend of experimentation with GPT-4 led to a groundbreaking change in direction for the company. Heller discusses the challenges of steering a well-established team towards innovation, the importance of collaboration with OpenAI, and the emotional milestones tied to a successful exit. The conversation highlights how modern solutions can dramatically improve legal research and client representation.
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49 snips
Aug 22, 2025 • 17min

Founder Mode: Paul Graham, Founder, Y Combinator

Paul Graham, the founder of Y Combinator, dives into the intriguing concept of 'founder mode,' inspired by Brian Chesky's insights. He explores the delicate balance between involvement and micromanagement, emphasizing how collaboration fuels creativity. Graham also introduces 'vibe coding,' a groundbreaking way for anyone to create code using simple English. He celebrates innovative founders like Andy from Stoke, while sharing humorous anecdotes about youthful perceptions and identity mishaps in the startup scene.
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32 snips
Aug 22, 2025 • 10min

Founder Mode: Garry Tan, President & CEO, Y Combinator

Garry Tan, the President & CEO of Y Combinator, dives into the transformative 'Founder Mode' event he organized for YC alumni. He highlights how AI is revolutionizing the startup landscape, enabling founders to thrive with smaller teams and innovative tools. Tan shares insights on the evolving dynamics of startup funding and the significant opportunities it presents. He also reflects on the journey of leadership for founders, emphasizing the balance between hands-on involvement and fostering a positive company culture.
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120 snips
Aug 22, 2025 • 21min

Founder Mode: Brian Chesky, Founder & CEO, Airbnb

In this engaging conversation, Brian Chesky, the visionary founder and CEO of Airbnb, shares insights on navigating leadership in turbulent times. He discusses the concept of 'founder mode', emphasizing the balance between personal vision and operational involvement. Chesky also advocates for direct engagement with teams, challenging traditional CEO practices. He highlights how a founder's unique experiences shape their leadership style and offers valuable strategies for overcoming the distinct challenges faced while scaling a business, especially post-pandemic.
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May 30, 2025 • 2h 27min

Ron Conway, Founder, SV Angel Part 4 (Bonus)

Ron Conway, the legendary investor behind SV Angel, shares riveting insights into the digital music revolution spurred by Napster. He recounts how founders Shawn Fanning and Sean Parker disrupted the industry, paving the way for platforms like Spotify. Stories of intense negotiations, the clash with Metallica over copyright, and the camaraderie among influential players encode the entrepreneurial spirit of Silicon Valley. Conway also highlights the ethical dilemmas faced during company shutdowns, making this an engaging look at the intersection of music and venture capitalism.
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29 snips
Apr 9, 2025 • 1h 17min

Ron Conway, Founder, SV Angel (Part 3)

In this engaging chat, Ron Conway, the founder of SV Angel, shares his journey as a venture capitalist with landmark investments, including Google. He reflects on the early days of Google, highlighting the competitive environment that birthed its success. Ron recounts humorous stories from the startup culture, offers insights into funding strategies, and discusses the emotional dynamics of key tech figures. The conversation also touches on significant moments like Google’s acquisition of YouTube, showcasing the relationships that shaped the tech landscape.
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51 snips
Mar 26, 2025 • 1h 31min

Drew Houston, Founder & CEO, Dropbox

Drew Houston, the founder and CEO of Dropbox, shares his journey from Y Combinator funding to creating a vital tech infrastructure tool. He delves into early entrepreneurial struggles, including a memorable demo mishap that launched Dropbox into the spotlight. Drew discusses the importance of startup culture, the challenges of personal development in leadership, and the innovative creation of Dropbox Dash to streamline workplace searches. His candid reflections on resilience and strategic growth reveal valuable insights for aspiring entrepreneurs.
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244 snips
Mar 12, 2025 • 1h 12min

Sam Altman, CEO of OpenAI

Sam Altman, the Founder and CEO of OpenAI, shares his fascinating journey from Stanford student to a tech giant. He reminisces about his early days at Y Combinator and the intense startup culture that shaped his path. Key discussions include OpenAI's evolution from nonprofit to AI leader, and the importance of safety in AI development. Altman also opens up about challenges during turbulent leadership changes at OpenAI and reflects on lessons learned from the chaos of startup life. Personal anecdotes add humor to his insightful experiences.
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15 snips
Feb 26, 2025 • 1h 4min

Eric Migicovsky, Founder, Pebble & Beeper

Eric Migicovsky, the visionary founder behind Pebble and Beeper, takes us through his groundbreaking foray into smartwatches, highlighting Pebble's incredible Kickstarter success. He shares fascinating anecdotes about the transition from iPhone to BlackBerry and the hurdles faced in the competitive tech landscape. Miguel reflects on the bittersweet rise and fall of Pebble, navigating venture debt pitfalls, and emphasizes the resilience and teamwork needed in startups. He also hints at the motivation behind his latest venture, Beeper.
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60 snips
Feb 12, 2025 • 1h 1min

Alexandr Wang, Founder & CEO of Scale

Alexandr Wang, the founder and CEO of Scale AI, shares his exciting journey from Los Alamos to becoming a leader in the AI data industry. He discusses the critical role of data in AI development, emphasizing its growing importance. Wang also highlights the balance of meritocracy and diversity in hiring, and the evolving challenges as a young CEO. Additionally, he dives into the fascinating human-AI collaboration and the revolutionary impact of technologies like GPT-3, offering unique insights into the future of artificial intelligence.

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