In this engaging conversation, Bill Gurley, general partner at Benchmark, shares over 20 years of venture capital wisdom. He discusses the importance of spotting market outliers and adapting mental models to new realities. Gurley highlights key insights from renowned investors like Jeff Bezos and Howard Marks, stressing the significance of strategic networking and understanding revenue quality. He also emphasizes creating competitive advantages through innovative strategies and challenges listeners to recognize biases in political discourse. A must-listen for aspiring investors!

Bill Gurley, a General Partner at Benchmark with a tech investing background, teams up with Michael Mauboussin, Head of Consilient Research at Counterpoint Global, to explore fundamental investment topics. They delve into the implications of AI and regulatory capture, discussing innovations that disrupt or sustain markets. Their conversation covers venture capital dynamics amid major tech layoffs and highlights the need for a balanced investment mindset. They also reflect on the influence of intellectual giants and the transformative power of teaching and writing.

Join Bill Gurley, a partner at Benchmark, known for his deep expertise in tech investments, and Brad Gerstner, CEO of Altimeter Capital, as they dissect the current state of Series A funding and the challenges unicorns face in navigating the IPO landscape. They delve into the implications of venture capital dry powder and cyclical market dynamics, shedding light on the recent trends in startup valuations. The discussion also addresses the urgent climate crisis reflected in the Maui wildfires, blending insightful analysis with urgent global issues.

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.

In this insightful discussion, Bill Gurley, a general partner at Benchmark Capital known for his sharp investment acumen, delves into the power of network effects in business. He explores how increasing returns reshape traditional investment strategies and highlights the importance of team dynamics in fostering these effects. Gurley also shares his fascination with user-generated content platforms and the evolving landscape of marketplaces, emphasizing their potential for growth and the significance of adapting revenue models in a rapidly changing market.

Bill Gurley, a seasoned venture capitalist from Benchmark, and Brad Gerstner, an experienced investor, dive into the tumultuous market downturn of 2022. They discuss how VCs are adapting to new realities in capital commitments and the strategic shifts needed in investment practices. Gurley shares his thoughts on popular media portrayals of entrepreneurs, while Gerstner offers predictions for the market's future. They emphasize the importance of reevaluating investment strategies amidst inflation and changing consumer behaviors.

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.

Marcelo Claure is an entrepreneur and investor who has founded and led some of the world’s most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world’s largest technology investment company. Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more. Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade. David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more. Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ’s total value. Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more. Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few. David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora. In Today's Episode We Discuss Price Sensitivity: 1.) How do you assess your relationship to price and price sensitivity? 2.) When is the time to pay up and have less price discipline? 3.) When should we remain disciplined and not pay up for a deal and walk away because of price? 4.) Of the deals you have paid up for, did their growth rate justify the high entry price? 5.) Knowing all you know now on price, how do you advise younger investors today?

Bill Gurley and Sunny Madra discuss open-source AI vs proprietary AI, strategic choices between open and closed approaches, and Sunny demos LLaVA, an AI tool. They also explore the rise of open source technology, the behavior of companies like Google and Microsoft, and the implications of Amazon's role in the AI industry.

Emily Chang and Bill Gurley discuss his keys to success over his decades-long career as a venture capitalist, whether the bubble has finally burst, and his favorite places for Texas BBQ. See omnystudio.com/listener for privacy information.